When Customer Confusion Leads to Churn


You can have the best, most feature-rich product out there, but if your customers do not know how to use it, they will churn.

I remember it well.  We had just implemented a massive infrastructure change in my organization years ago, and we were excited to see how it would help us build out convenience across multiple departments.  We rallied, issued training to the power users, and advertised with key stakeholders, and it looked like we had a winner on our hands!  And so, we went live.  

Then, things started running into trouble.  Departments didn’t conform to the processes we put in place, and tried to circumvent them because they didn’t follow their previous processes.  Our team would follow the processes as outlined, yet requests would go missing.  Incidents would get submitted, but not resolved.  The brilliance of our new infrastructure design was showing cracks. Sure, we had great tools, but we struggled with the results.  We needed a change.  Or, better yet, proper training.  

This same scenario has played out for several IT Management platforms I’ve worked on, and each one had similar results:  turn it on and hope that folks will just learn to use it.  Well, it doesn’t work that way, and more often than not, the contract would not get renewed, and we would go through the same process with another product in 3 years.  

The thing is, this could have easily been resolved if we received proper training as part of our Change Management process, which would have resolved our churn, and that of many other clients.  Let’s explore how that would work.  

Tools are Replaceable, and always misused

Until we finally understood the right process and workflow through a platform, that platform was, essentially, just a bunch of tools we could use on the job.  Tools, folks can understand and use, even if they use them incorrectly.  I admit it, I’ve used a crescent wrench as a hammer before, when I couldn’t find my hammer.  Did it work?  Sure.  Was it good for the wrench?  Nope.  I left nicks in the metal.  Still, I used the tool that was handy for the job I wanted to complete.  

This same principle happens when you use your fancy platform as “tools.”  Need to track IT requests?  Incident tickets are tools to do that.  Need to track changes to your infrastructure?  Change tickets will do that just fine.  Don’t quite know how Change Management works, but you need to track a Change request?  It’s tempting to use an Incident if that’s what you know.  Sure, you don’t have the same workflows, but at least you are tracking it, right?  

Eventually, you realize that your methods of doing things aren’t working, and the tools don’t seem to live up to their promises.  Where is the automation?  Where are the approvals?  How does it relate to devices in the CMDB?  So, you start asking yourself, why did we invest in this costly platform if it’s not doing what it promised to do?  So, you start looking for other solutions.  

The Data

In this hypothetical example, I’m using a vague IT Management platform.  You could replace this with any platform and any similar scenarios:  I’ve seen this play out with several digital platforms in the past.  If it’s not used properly, it feels “broken,” and you look for a replacement.  It’s a costly migration, lots of money spent, and yet the same problem will exist.  

The thing is, all this could be properly avoided if your user base were properly trained.  Training would give them the knowledge of how to use the platform, when it should be used, and why it works the way it does.  This means training on the platform and the new processes to as many people as you can.  How do I know this works?  Because I’ve been on the opposite end of it:  I’ve received the necessary training, I’ve delivered the necessary training, and I’ve planned the necessary training when implementing.  So let’s go through the data.  

01

End-User Skills Gap

When evaluating the problem areas in the platform, we often came to the same common issues:  End users were attempting to circumvent the new processes that the platform provided for what they used to do (email requests, no follow-up, no reviewing of the platform, and often ignoring the platform).  Users were struggling to get their requests and incidents addressed because they were reaching out to their “guy” in the department instead of going through the process.  

The Solution

We needed to better understand how customer workflows at the end-user level operated.  We met with customers, ran surveys, and analyzed the user data available to see what worked and what didn’t.  More often than not, the end users would use non-traditional methods to circumvent the new processes established by the platform because it’s “what they always did.”  

This was a clear indicator that end-users needed to be trained on the expected process they would take, and the benefits of the platform as it came to them as part of the Change Management process to the new platform.  This would easily be resolved by creating platform-specific, micro-training videos that walked end-users through how to submit their incidents, monitor progress, request updates, and educate them on the current processes.  

The Results

The results were dramatic.  End-users were more comfortable with the new incident process, which triggered proper requests to go through with monitoring and automations in place.  Incidents were automatically assigned to appropriate departments, and responses were swift as SLA counters and triggers would kick in.  

02

Power-Users and Broken Processes

The next common issue that came up was broken processes that were being built into the platform by power users.  The platform was designed for specific functions with pre-defined automations triggered as specific stages or assignments were made.  The Power Users, on the other hand, knew what their current processes were and built them into the new platform.  Did it work?  Well, as well as previous processes worked.  Was it faster?  How could it be?  Power users were using the same broken processes that would take just as much time as in their previous environment.  No benefit was being seen.  

The Solution

It was clear that power users needed to understand how the platform was designed, where the automations kicked in, what processes were built in for their benefit, and how to customize the process for optimization.  

We started with the research:  looking at what customers were doing and how they were approaching their problems.  Surveys revealed that customers were performing much the same steps within the process, with a lot of additional overhead that could be weeded out.  We then refined processes, workflows, and the platform UI to better support their goals as power users while highlighting the value the platform brought to the table.  

Now, we needed to communicate the new process and results:  This required multi-day power user bootcamp-style training, walking them through the platform, helping them understand how the platform was designed, and where the automations triggered.  We worked through the process steps, where customizations could and should be made, where the default process shone, and how it would apply in their own environment.  The goal was to help them reimagine their broken processes by following one that was already optimized by the platform.  

The Results

The classroom results were dramatic.  Several power users were blown away by the strength of the process that was built in, and understood where their existing processes were broken.  As we worked through each lab, they would stop, take notes, and often ask questions on how they could make this same process work in their own platform.  The change was dramatic:  They saw the platform as a platform, not a set of tools that they should use.  The change in perception made a huge difference, and the adoption of the baseline automations accelerated amongst multiple customers. 

 

Understanding the Solution

This was a mock evaluation loosely based on similar case studies I’ve completed in the past.  The process is pretty much the same for each one:

  • Identify the business outcome you want to achieve
  • Measure your baseline of success
  • Identify the gaps
  • Change those gaps into outcomes:  How do you know your steps you are taking are successful?
  • Deliver the Training and measure the outcomes

This might seem simple at first, but there’s a lot of work that goes into each stage, which is why an L&D leader, like a Fractional Chief Learning Officer, is so valuable.  If you have current issues and would like to talk strategy, let’s chat! 

Intentional, or Accidental?

Early in my career, I worked as the systems administrator for a very early startup, with only 10 of us, many family members of the founder.  It was wild, and we were running on a shoestring.  We brought on some folks to the tech support team.  This was my first introduction to employee enablement:  I developed the training for our tech support.  It was wild, it was ad hoc, barely structured, but it did the job for those who had some basic experience.  Those who did not, they really struggled. We had heavy turnover, with many sticking around for no more than 90 days.  

You see, if you don’t properly train your folks, they will leave as they do not have the adequate resources or experience to succeed.  No one likes feeling like they are failing.  

And yet, in many early startups, one in three employees considers leaving within the first 90 days due to poor onboarding.  Think about that for a minute:  All the cost you put into recruiting, interviewing, finding a good candidate, and getting them started.  All lost, because they didn’t have the tools they needed to do the job.  They didn’t know where to go, what was expected of them, how their success was measured, or how to do key parts of the job.  

Now, once they leave, you have to start all over again, often spending up to 2x of their salary just to get a replacement.  As a startup, you can’t afford that.  You also can’t afford the lost momentum those hires would have brought, the bottlenecks that will result due to unfulfilled roles, and the days, weeks, months, or even quarters where you just can’t find the right person who will do the job without needing onboarding.  Hint:  you can’t.  Everyone needs to be onboarded. 

An image that displays the chaos of multiple LMS systems

You are training your people, whether it’s intended or not.  The only question is, are you intentional, or is it accidental?

The Myth:  “We’ll Figure It Out Later”

But you are a busy guy!  Leading an early start-up, you are busy with Sales crushing deals, evangelizing your product to everyone and anyone that will listen, and looking to build your market share.  It’s why you hire!  You need people to take aspects of the business you don’t have time to do yourself.  So, you figure you can hire experienced folks from other similar companies and they will just “figure it out” as they go along.  So, you step back, take your role under Product or Sales, and just let onboarding happen.  

The belief, or the myth, is that smart people will just figure it out.  They’ve worked in their industries before in similar roles; they can just make that happen.  So, you turn them loose onto your fledgling company with little direction and hope for the best.  The anecdotal evidence that feeds the myth is that, often, people make it work.  They bring their experience from their previous companies, build their own fiefdom with their own policies and operational roles, such as IT and HR just have to figure things out as each department runs on its own rules and policies.  It’s inefficient, often expensive, and feeds silos where collaboration should exist.  

At the employee level, this feeds controlled chaos, areas where people become “indispensable” because they hold all the tribal knowledge for their department.  If they go, the department is thrown into disarray and confusion as co-workers immediately update their LinkedIn profiles and resumes.  Employees become disengaged because they don’t have a firm foundation of policy and procedure: It all comes down to the memory of their co-workers and shadow support processes that develop in response to the vacuum.  How can they make a decision when it’s immediately undermined by a more experienced co-worker? 

Finally, there is a more operational hit.  As teams realize their need for training, they will start training internally, their own training, their own takes on policy and procedure, their own LMS.  I’ve walked into companies that had 5 different learning management systems, and new employees were expected to use every single one of them as part of their onboarding process, as dictated by a wiki page or Word doc that was constantly out of date.  License costs were crazy, and those expenses could have been better applied to hiring new people.  

The Hidden Costs of Poor Onboarding

So, you figure, “well, it’s just the cost of business, right?” And as your teams start to build their own programs, their own policies, their own mini-companies in your company, the one you have poured your heart and soul into, you carry on, hoping things will work out on their own.  So, what exactly are the “costs of doing business” when you come right down to it?

01

Lost Productivity

Poor onboarding means it takes longer for employees to get up to speed.  Most organizations will have a 30-60-90 day plan, which, if you don’t prepare your employees properly, will extend for weeks, months, or even quarters as they “Try to figure it out themselves.”  Eventually, of course, they do, but you have wasted months of productivity while senior staff are constantly pulled in to shadow new employees, dealing with missed KPIs and increased training needs.  It’s inefficient, it’s costly, and it’s leeching momentum from your growth.  

02

Higher Turnover

When there is a lack of clarity, a lack of direction, or a lack of support, employees become continually frustrated.  Many try to contain this frustration internally, which feeds into poor mental, emotional, and physical health.  Eventually, the work of catching up becomes too much, and the calculations start:  How much more frustrating is it to try and meet unknown, vague, and/or inconsistent requirements than to try and find another job?  It may take 90 days, 5 months, or even 1 year, but that calculation is constantly running in your employee’s head.  

Now, you need to hire someone to replace them.  The cost of replacing an employee can run as high as twice the compensation of the employee who left.  It’s like hiring three people to keep one.  Is that efficient?  Is that economical?  Is that good for business?  Now, couple that turnover with the costs of delays, bottlenecks, and stalled growth.  

03

Cultural Drift

When teams are left to fend for themselves, they develop their own culture, policies, processes, and expectations.  If your company doesn’t structure onboarding, it’s happening by accident.  You may be the most employee-first, diversity-minded, and ethically-driven leader, yet your ideals and values are not the ones being perpetrated.  The culture that is perpetuated is dictated by your early employees, or those who remain.  Those who are dealing with their own frustrations, those jaded by their own poor onboarding experience. That will be the culture of your company, that will be your legacy, until you decide to fix it, and fixing a culture is extremely torturous and expensive. 

04

Customer Impact

“Still,” you think, “that’s a problem for another day.  Our customers can’t wait, and I don’t have time to dedicate to proper onboarding right now.”  Imagine for a moment, you walk into a hospital for a routine bypass surgery.  Your doctor finds out that the surgeon slated for your procedure has left, frustrated with the hospital policies that constantly change on a whim.  So, as your doctor, they are asked to do the surgery.  Leadership thinks, “You’ve been to medical school, right?  You can do this.”  The doctor, your family doctor, one who does stitches or the occasional hernia check, is expected to expertly cut into your chest and perform a bypass.  As a patient, would you go back to the hospital?  Would your doctor?  

Customers can tell when their Sales, Customer Success, and Support teams are poorly trained or supported.  They know, because they’ve seen it in their own companies.  Your customers lose trust in the company and are now doing the calculation:  Do you bring enough value to warrant the frustration they get from poorly trained contacts?  Once the calculation has started, it’s difficult to reverse it.  It’s difficult to rebuild trust once it’s lost.  That means churn.

05

Leadership Burnout

“But,” you say to yourself, “I hired leaders to take care of this.  If they can’t do it, I’ll get someone else who can.”  Sure, you can blame your leaders for your lack of dedication to proper onboarding for your company.  So you start to churn through leaders, because they are getting burned out trying to make onboarding happen in a structured way.  Blame is thrown about, and good, talented leaders, left to their own devices, start looking elsewhere.  

I’ve been on both sides:  Leaders leaving because they just can’t get anywhere with senior leadership, and as a leader, struggling to make things work in a culture of vague direction, promises, and poor onboarding.  Onboarding can make or break whole teams.  

An image of a CEO, frustrated that things aren't going according to plan.

Why Early-Stage Startups Are Hit Hardest

When you are just starting, you need every headcount you can get.  You need folks who can hit the ground as quickly as possible, keep on message, and grow the company.  Sales for new logos, Customer Success, Product, and Support for retention.  You need to build a structure quickly and efficiently.  Every weak ramp-up process derails progress and delays growth.  

“Well,” you might think, “Perhaps I just don’t need the headcount.  My team is small, but they can make it happen.”  They can, now.  But can they, when one person is hit by the lottery (because it’s nicer than being hit by a bus)?  Perhaps they leave for a better opportunity elsewhere, or start their own business?  Do you have the redundancy necessary to cover for those who are temporarily or permanently out of the office?  And what about mistakes made by the team, without help?  Newly onboarded employees will make mistakes.  Poorly onboarded employees make serious mistakes.  Mentors can help mitigate the impact, but not if you are short-handed.  

What then does your budget allow?  Frequent turnover is costly, not just in lost sales or lost customers, but in real dollars.  Limited budgets can’t afford high turnover because of poor or non-existent onboarding.  


Small teams are hit worse by less redundancy and more mistakes.

Signs Your Startup Has an Onboarding Problem

“Yeah, sure, what you are saying makes sense,” you are thinking to yourself, “but I don’t have a problem!”  Perhaps, though, you pause.  Then think, “How would I know?”  That’s a much better response:  How do you know you have a problem with onboarding?  What are your indicators?

The first sign would be that your new hires are asking the same questions again and again.  And again.  They ask for a momentary response or solve the immediate problem, and the answer is pushed out by the next crisis.  Answers are not internalized, skills are not developed, and learning isn’t happening.  This is, quite often, the case when you rely too heavily on mentors and on-the-job training.  Don’t get me wrong, both are valuable to the onboarding process!  But your new-hires need a strong foundation of information and skills from which to draw, so the practice can apply. 

This leads to our next indicator:  your teams rely too heavily on shadowing and mentor leadership instead of structured training.  Mentors provide guidance and knowledge checks, but shouldn’t be there to teach.  They don’t have time; they have their own jobs to do!  Structured learning provides that necessary foundation that Mentors can place into context, showing the value of mentorship.  

Next, we have inconsistent performance across hires in the same role.  Some folks do really well in the chaos, quickly acclimatizing themselves and running with it.  Others struggle.  Inconsistency in onboarding is a sign that something is wrong, and it’s not your new hires.  One constant is true with hiring:  Those who are hired generally want the job.  Maybe not because they are motivated by your Mission, or even by the team they are on, but ultimately, they want to work (or they wouldn’t have applied).  Onboarding should provide a baseline of performance from which everyone can work.  Mentorship places the training into context, and everyone should have the same opportunity to succeed.  Even if you follow the standard Bell curve, at least 75% of your team members should meet their KPIs within a reasonable amount of time (generally 1.5 to 2 months).  If you aren’t seeing that baseline result, there is definitely something wrong with your onboarding process.  

Finally, your managers, or you as the founder, need to constantly re-explain “how we do things.”  Culture is critical to a company, but if you constantly have to remind your employees of how things are done, something’s wrong.  Now, I’m not talking about basic compliance training, which is required by law.  I mean explaining your culture:  How the company does business, why people do the things they do, and what’s important for your business outcomes.  This goes beyond compliance; this is the heart and soul of who you are as a company, your brand.  

Employee working from home

The ROI of Getting Onboarding Right

“Okay, okay,” I can hear you say, “but how do I know onboarding is going to be worth it, and not just another expense you are trying to sell me?”  A good question.  Onboarding is much like a service:  If it works, you don’t know it’s there.  When it doesn’t work, everything is in chaos.  Let’s break down the real benefits of good onboarding.  

First, you have a faster ramp-up process for new hires.  They are ready in weeks, not months.  Skills are taught at an accelerated rate because you aren’t relying on the live environment to give you all the experience someone needs:  You have it set up in a controlled, curated setup that covers almost everything.  This translates into real business growth and bandwidth because hiring bottlenecks are removed. 

You have reduced turnover and, therefore, fewer recruiting costs.  Your new hires are more comfortable, more prepared, and feel ready to go faster and without much mentor intervention.  They ask fewer questions, they contribute faster, and the business is better placed to grow.  Without increased recruitment costs and lost experience from high employee turnover.  

Your culture is stronger, the vision of every employee is aligned with the founder’s, and employees feel connected to the company’s purpose.  Employees know what you want, they know what drives you, and they understand why.  

Your onboarding process can scale with your hiring needs.  Onboarding playbooks prepare you for rapid growth, setting well-established processes in place with regular reviews for updates.  It doesn’t have to be complex, it doesn’t have to be all video, and it doesn’t have to be difficult to set up.  You just need to be organized, have an easy method of tracking progress, and measure the success.  


Proper onboarding means real returns on your investment: productivity, time-to-value, and significantly reduced recruiting costs.

Practical Steps for Startups

So where do you start?  Once you know you have a need, you need to get the plan in place.  

Start with a “Day 1–30 Roadmap” for each role.  Your HR team, ideally, should have skill requirements and job analyses for every role.  Chances are, though, the HR team for a startup doesn’t.  It’s a large task, and you likely have a small team that handles onboarding.  Often, this task is delegated to the hiring manager.  Then, build out a 30-day onboarding roadmap that level-sets job requirements and skills, familiarizes the learner with the processes for the role, and sets milestones for success.

You can then document those processes somewhere they’re easily accessible.  Start with docs (Google Docs, SharePoint, Notion, Confluence, etc) and make sure everyone has the access they need.  Create learning paths that are user-specific in your LMS (preferably only one for your org), and assign the learning they need.  This should be role-specific, with knowledge checks.  The training doesn’t have to be complicated or completely built out by hand.  If you have a Large Learning Library (LinkedIn Learning, Skillsoft, etc), then use the training that is available there for generic role skill sets.  Be creative, and you can make it happen with the resources you already have.

Then, assign your onboarding buddies/mentors as guides.  They can track the onboarding process, verify that the learner is meeting their milestones, and provide context for the training.  You can use your training platform as a way to measure progress, communicate milestones, and provide guidance for your managers as they follow up on development.  

Finally, treat your onboarding as a strategic investment, not an afterthought.  The success of your onboarding means success for your new hires.  The success of your new hires means the success of your company as it scales.  

Captain working on his navigation plan.

Poor onboarding drains start-ups, keeping them from scaling successfully.  By investing in onboarding, you are not investing in overhead.  It’s acceleration fuel for scale.  Treat it as the valuable asset it is.  

If your team is growing and you’re concerned about onboarding gaps, a fractional CLO can help design a scalable onboarding framework without the cost of a full-time exec. Let’s talk.

Two versions of the same person representing the two processes of the brain:  Experiential Response and Reasoned Exploration.

 

Owning Your Learning Success in the Age of AI

 

 

Growing up, we spent a lot of time camping. While camping, we would occasionally need to wash clothes, and as it happened, my parents owned a washboard and taught us how to use it when cleaning clothes in the creek. It was very rustic, and a lot of fun for little kids who were learning something new.

Now, I’m sure many of you out there have no idea what a washboard is, since the washing machine has been around for over 100 years. Knowing how to use one isn’t common knowledge. Everyone from CEOs to janitors has gotten along just fine without needing to know how to scrub clothing on the board to get the dirt out. It’s a lost skill, replaced by modern technology, and only picked up as a novelty skill. Much like celestial navigation and sailors, since GPS has become so ubiquitous, or from-scratch cooking since fast food and ready meals are so common. It takes extra, conscious effort to acquire these skills that were replaced by modern technology or conveniences. Now, we have AI.

I’ve been spending a lot of time researching Artificial Intelligence, as I’m sure the rest of you have been as well. I’ve worked through the early Turing days, different Machine Learning models, and spent time learning about LLMs and Agentic AI. Each time I look at what it can bring, I keep thinking about how it will impact Learning.

Perhaps I’m dating myself, but I was there when personal computers in the classroom were a novelty (we had Atari 2600s in my 6th-grade classroom). I saw how computers could help kids engage in learning through gamification. It was supposed to be the next revolution in education, yet we still have instructors in a classroom. I was there when we first started doing remote learning at my local Community College, and even helped provide video discs for learners (because video streaming was murder in dial-up speeds). And I was there when MOOCs were becoming a thing, and Apple was courting Universities to post recorded class sessions to iTunes U (now defunct). At each stage, there was supposed to be a revolution: a change in how we teach, and yet, we still have instructors and teachers in front of classrooms (or on Zoom).

But now. Now, we have AI. We have ChatGPT, Gemini, or Anthropic, which can answer questions for you when asked. They seem to have all the answers and can confidently respond without hesitation (right or wrong). They can rewrite your scribblings into a coherent, structured paper or article. Why practice sentence structure or the art of essay writing when an LLM can do it for you? It seemed so revolutionary that some companies have, reportedly and anecdotally (not confirmed), fired their L&D teams and given every employee a ChatGPT license as their source of learning. The reported results (again, not confirmed) were a disaster. Skill gaps widened instead of narrowing. Why? Why would skill gaps widen when answers were right there?

Well, to address that particular question, I would recommend an excellent video on AI and Learning called Effort is the Algorithm. The video pointed out that there are two processes our brains use: One is fast and uses the available knowledge and experience we already possess. Think of it as the computer hitting RAM for cached information. This process uses all the knowledge and experience you gained from years of learning, trying, failing, trying again, failing, trying again, and finally succeeding. You’ve lived it, you know it, you have put it to the test, and you can confidently respond without having to think too much about the answer.

The other process is slower, more methodical, and used when learning something new. This process is engaged when you are working through a problem, failing, trying again with a new approach, and repeating until you achieve success. This is learning. You listen, you watch, you try, and see results. Your mind engages, building Neuron connections with each practice (the general magical number is 7 for long-term retention), and you have banked a block of knowledge/skill/behaviors that can be utilized by Process 1.

So, what happens when you offload your learning practice to AI? Process 2 is happy to offload anything that takes extra effort/energy/resources, and Process 1 simply regurgitates the short-term information it has and purges that info. This is why skill gaps happen when you rely on AI as your Process 2: you are not building blocks of knowledge/skills/behaviors that you can call upon when pressed. There’s no effort in learning key information points because you are relying on external sources.

Now, is it really a bad thing? The same could be said of that washboard use, right? The general population doesn’t know how to use one; they offloaded that knowledge to the washing machine, and the world still turns just fine. So the question you should be asking yourself is: How important is the information/skill/behavior you are getting from AI to know when doing your activity?

Let’s put this in context. You are in Sales, and you are raving about the benefits of your company’s product or service. AI can give you all the talking points, highlight the key benefits for the customer, and might even be able to give you some customer insight ahead of time. What a great way to prep! Then, you are in the pitch meeting, and someone asks a question about how the product/service works. If you have to stop and ask AI, does that show confidence in your knowledge?

Let me put it another way. You are in the hospital for heart surgery, and your surgeon comes in for your consultation. You have, understandably, some concerns about the surgery procedure and need some clarification. You ask, and the surgeon turns to the computer and asks ChatGPT how the procedure should be performed. Would you keep him as your surgeon?

Now, I’m not saying AI doesn’t have its benefits in learning: It does! You can do amazing things with AI both before and during instruction. But as a learner, you can’t offload the learning process to AI. It doesn’t build your knowledge base, skill sets, and behavior guidance you need to be successful in your job. It’s your responsibility as a learner to put the effort in, try, fail, and keep trying until you succeed. That is learning, that is success, and that is what will ultimately differentiate you in the industry. Make the effort, and you will see amazing results.

 


You can’t offload your learning to AI to be successful.  You need to use AI to learn, try, fail, and try again until you succeed.  That’s learning, that’s succeeding.

 

 

 

 

 

A Compass Gives you Direction.

A Navigation plan Gets you There.

 

I remember, as a young scout, getting my first compass.  I thought it was the coolest thing in the world, and, if Television and Movies were anything to go by, it would always point to where I needed to go.  Quickly, to my confusion, I learned differently.  The compass only points North.  How would I ever find where I needed to go?  

Then we started Orienteering, and I learned how the compass can be used as a tool as part of a wider plan.  A compass, by itself, only lets you know in which direction you are going.  You need other tools, like a map and GPS to understand where you are and how you can get to your destination.

Sailing changed things a bit more, because orientation on water means an understanding of wind, tides, and weather.  Now, instead of navigating around mountains, you are navigating shoals, reefs, storms, and large container ships.  Your navigation plan is essential to navigating to your destination.  

“Knowing where you’re going isn’t enough. You need to know how to get there and what might throw you off course”

 

Teams struggle similarly with their training plans.  They generally know what they want:  Growth, innovation, agility, product adoption, etc., yet they lack the actual plan to get there.  Often they start creating content for a product or service, covering features, shot-gunning capabilities in hopes that the learners will learn and apply what they need.  It’s distracting, confusing, and often falls flat.  

The problem is, the team isn’t directionless, just at a loss of what to do, and how that’s going to be done.  They know where to point their rudder, but need to navigate around islands they get frustrated.  Then, as leadership and/or messaging changes for the new Sales cycle, pressures mount to create content that talks to those new positions.  The storm hits, and the team is just bouncing, trying to do what they can with what they have.  There’s no vision, no plan, no structure to the process.  Some leaders will call this being “agile” but I call it blind panic.  

With a plan, even when the storms hit, you know where to go safely.  If you have a set process and procedures for your training, the Team can afford to be flexible and agile, knowing what to change, how much to change, and how much work it’s going to be.  No more panic, but structured refocus.  

A Navigation Plan Aligns the Team Around Milestones

Sailing with a crew can be amazing, when everyone knows what they are supposed to do, when they should do it, and how it’s done.  When I sail with my family, I have a son manning the port lines, my wife manning the starboard lines, so all I have to do is man the tiller and mainsheet as we navigate.  We know where we are going, how we are going to get there, how many tacks it will take, and how long in each tack we should be.  As everyone does their part, we move well and enjoy the experience. 

If I go out with an inexperienced crew, with no notion of what they need to do, how to do it, or when to do it, I’m left with having to do everything myself, hoping that they will just “get it”.  It impacts the plan, because they don’t know what to do, and I need to compensate.  It’s unnatural, slows things down, and we often ended up turning too far in a tack while I was securing lines.  

When everyone knows what they are doing and how it contributes to the bigger journey, everyone wins.  Not only do they know what they are doing, when to do it, and how, but they can flex as conditions change.  The plan, goals, and milestones remain the same, allowing for execution to flex with need.  Planning means agility, flexibility, and comfort for the team.  No plan means chaos, confusion, frustration, and increased turnover.  

The plan also creates a shared language when communicating issues, solutions, or changes, keeping everyone in the loop.  It also provides accountability and focus:  People know what they should be working on, what they own, to whom they report, and the priority of each task.  

And when the Storms hit, focus can flex using the plan as the guide.  Milestones may shift in timing, but remain.  Responsibilities and accountability is still there, just with new focus.  Priorities may shift, but the overall plan is still helping everyone make their final destination.  

Captain working on his navigation plan.

“It’s not about rigid planning.  It’s about intentional movement with shared awareness.”

Support continuous Learning, not Just one-time Training

I remember my first time out on any body of water.  I was camping with the family by a beaver pond in the mountains, and I gathered some logs together and lashed them into a raft.  My young mind thought of the adventures of Tom Sawyer, and I was going to float on the raft.  Did it work?  Sort of:  I had really wet feet, but I didn’t have to swim.  I wasn’t prepared, I didn’t know what I was really doing, I was just, well, doing.  

If you develop training without a plan, it’s like lashing some logs together and calling it a ship.  Sure, it works for now, but for how long?  What’s the impact?  Can it scale?  Ad hoc training doesn’t scale and means redoing everything from scratch, every time.  

A good navigation plan will weave learning into daily work, leadership coaching, onboarding, and product development.  Stakeholders will all have a voice in the development of training, with clear expectations in the process.  

Navigation Plans Help You Prioritize What Matters

Every time we take the boat out, we have a plan for where to go and how we are going to get there.  I know when we will tack, how long we will spend going in which direction, and when we will be heading back to the slip.  Checkpoints let us know where we are relative to our time:  Do we need to modify the plan to get back on time?  It’s all part of the navigation plan. 

Training is no different.  Clear waypoints, such as product launches, team scaling, onboarding new hires, set the pace of the plan, and we know how to choose the right tools and frameworks at the right time to hit those waypoints on time.  Instead of rushing to getting everything done at once, we hit the right sequence to provide a smooth launch.  

 

Leaders use Navigation Plans to Inspire Trust

When it’s just you, you can just climb aboard and go.  You know what you can do, you know where you are going, and you can build out the waypoints in your head, and you just do it.  Descriptions are not necessary, written or verbal plans are not needed, because it’s just you. 

The crew, on the other hand, need to know what’s going on.  They don’t just need a direction and will take orders barked at them while you go.  This isn’t Mutiny on the Bountyand teams don’t work on blind faith.  They need to trust that you know what you are doing, how you will get there, and what their responsibilities will be. 

The thing is, this could be taken to extremes.  Some leaders jump in and set every step down in meticulous detail, which quickly gets overturned once headwinds change.  It’s not about knowing every wave, just where the shoals are.

 

 

You can’t JUst Wing It Anymore

Your company is growing, your team is growing.  More people are doing more specific tasks that contribute to the overall success of the company.  It’s not you, alone in your dinghy crossing the Bay, you are on a larger ship with a lot of hands.  There’s too much complexity to rely on instinct alone:  You need a plan, and a Fractional CLO can help you build one without full-time headcount costs.

Your clear navigation plan becomes your competitive advantage:  it saves time, reduces friction, resolves frustration, and boosts confidence across the organization.  

It’s time to:

  • Map your key journeys: Onboarding, product adoption, and role transitions
  • Set your clear waypoints: 30/60/90-day goals, enablement outcomes, and promotion criteria
  • Align stakeholders: Co-create the plan with team leads, not just top-down dictation
  • Revisit the map regularly:  Course correction is a feature, not a flaw

 

 

 

 

Training Happens Whether You Know It or Not

We’ve all been there: walking into a company with 3 to 5 learning management processes, three checklists with mostly the same content on each one, and a lot of outdated information that a new hire is expected to update when they find it doesn’t work.  Leaders rely heavily on tribal knowledge, existing documentation, shared knowledge dumps, and the occasional video walking through the product.  

The thing is, each of these methods really does count as training.  This might be a controversial statement to make as a Training leader, but training happens whether you want it or not.  People will share knowledge, best practices, and policies that are developed on the fly to create a cohesive experience for everyone.  

The question you have to ask yourself is, do you want your people trained in this way, with no oversight, no organization, no actual plan?  How long does it take for someone to be up to speed on your processes, vision, direction, or purpose?  How long until they are productive?  

If you don’t design your training process, chaos fills the gap, and poor knowledge transfer means lost productivity, repeated mistakes, uneven performance, and employee frustration.  

Leaders are training teams every day; the only question is whether it’s by design or by accident.  

 

 

Organizational Success Depends on Learning Agility

While working for ServiceNow, I had an amazing mentor who peeled back the business side of training for me.  I saw that our customer training program would grow right along with the company’s growth: maintaining 4% (at the time) of the overall company revenue.  That growth was just as organic as the company, keeping pace and flexing with the company’s direction.  

All other companies for which I’ve worked had struggled with that type of growth:  as Start-ups, they saw training as a secondary thing, something that was the responsibility of the Deployment or Implementation teams.  The results:  struggling adoption and a lot of questions on how to do things on their platforms.  The structure of training wasn’t there, the coherent messaging was missing, and resources to develop training were strained.   They needed something better.  

Early stages of an organization are fast-paced, with quick changes on every pivot.  Products change often, policies are developed on the fly to handle more and more common scenarios, and you need your people to keep pace.  Structured training programs with information capture processes, single-hosted training locations, and predictable session plans will provide the framework that employees will rely on when ramping up on new products, processes, and procedures.  

Having a single vision for knowledge transfer streamlines this experience across the board, standardizing all onboarding, upskilling, enablement, and customer training, keeping pace with the momentum of the company.   Without that vision and direction, without structured learning systems, growth velocity will stall.  

 

 

 

 

Onboarding is a Growth Multiplier

If you don’t have structured onboarding, it can increase your new hires’ time to productivity by 30-50%!  Think about that for a second:  newly hired people, hired because you are growing like crazy, can’t get up to speed as fast as they should.

 How fast is that?  Well, it generally takes between 90-100 days to be fully onboarded and productive for any new role.  New employees will, essentially, suck at their jobs for at least 45-60 days as they ramp up, get trained, and get experience in their new role.  Now, if you don’t train them, you increase the growth period by another 30-50 days.  Half a quarter longer, because they are not properly onboarded. 

Now, Onboarding isn’t just your general compliance training: It’s learning the tasks, proprietary knowledge, and vision that make your company, well, unique.  Don’t sacrifice that because you think it takes too much time. 

 

Playbooks, Not Tribal Knowledge

Too often, leaders will point to a senior member of their team and tell a new hire to “do it the way they do it” and expect to rubber-stamp an employee’s knowledge.  The thing is, it doesn’t work that way.  

Having lived through that more times than I care to count, I can tell you from experience that the senior member of the team is doing their job, and will not have the time to properly train their new co-workers.  Instead, they say, “Do this and let me know if you have any questions.”  The new hire, then, tries and fails, tries and fails, all the time feeling like they just can’t do the job.  

Then, what happens when your senior team member leaves the team?  Where does all that knowledge go?  Not a good situation, because not everyone creates a knowledge base to brain-dump before they leave, like I did. 

Building documented systems early, even when messy, prevents bottlenecks and standardizes knowledge across the team.  A good CLO will help turn your tribal knowledge into repeatable, scalable assets. 

 

 

 

 

Your Team Is More Than Sales

The Sales team is a critical team for the growth of a company, and leaders will pump a lot of funds into their enablement, as they should!  But what happens after you Close/Won an Opportunity?  

While working for a small start-up, we had that problem.  The economic headwinds spooked the Board, and hiring freezes were in place for every team but Sales.  Sales then had a bumper year, outstanding growth, lots of new customers, who couldn’t get onboarded.  We didn’t have the deployment team to support he growth.  Prioritizing Sales brought in a lot of new logos, but they weren’t happy when they were waiting 6 weeks to realize value. 

Enabling Sales is important, but you need to enable the rest of your teams with just as much passion and urgency.  The Customer Success team needs to know what Sales communicates to customers, Professional Services needs to have the knowledge/skill to get those customers launched as quickly as possible, and Support needs to know how to support the customer if something doesn’t work.  

A good CLO will support cross-functional learning so silos don’t slow down execution.  Sales, CS, Product, and Ops all benefit from unified learning leadership. 

 

 

Early Learning Culture means Long-Term Competitive Advantage

My favorite employer experience always came with well-organized training programs.  Proper onboarding, clear expressions of expectations, documented policies and procedures, and good on-the-job training sessions with a dedicated mentor who was dedicated entirely to my onboarding.  I spent more time being productive and building relationships than struggling to find answers, stressing about my performance, and doubting my own skills.  It’s such a pity it happened so rarely in my career.

Organizations that prioritize training early on in their growth develop a strong learning culture, generally democratized and collaborative, that naturally work cross-functionally.  They recovcer quicker from mistakes, adapt faster to the market, and build stronger cultural ties and practices that resonate across every role in the company.  

If you don’t start your learning culture before your Series A funding round, you will forever be playing catch-up.  Instead of greasing your growth engine, you will deal with organically grown, tribally driven training systems that are more wiki-driven, fractional, and disjointed than structured.  

 

 

 

 

 

 

 

Sailboats on San Diego Bay.

Sailing as a Metaphor for Training Systems

I love metaphors, partly because so many different metaphors can be used for any given topic, but mostly because it helps folks relate to a topic by taking a familiar experience and relating it to something new. 

So why sailing?  Because I love sailing.  I’ve been a member of our local sailing club for a while now, and there’s something powerful about getting out on the water.  I’ve talked before about Blue Mind theory, and getting on the water seems to reinforce that theory for me (anecdotally, of course).  I therefore recommend anyone interested to try sailing.  

So, how can sailing relate to training?  There are a lot of ways, and we will explore them below.  


Whether Sailing or Delivering Training, it’s all about preparation, experience, and capacity planning.

Navigating Training Mechanics for Success

My last sailing session was a 4-hour trip around San Diego Bay.  It was a windy day for a small 22-foot keelboat, and even with the mainsail and jib reefed, we were easily moving between 5 to 6 knots in 11-knot winds.  The spray was flying off the bow, the rail was in the water, and my crew, some of whom had never sailed before, were not quite sure of the experience.  And yet, we kept it moving as I tried to single-handedly steer a boat that was built for at least two crew members.  It all came down to the mechanics.  

Upon reflection, I noticed that I could easily relate this experience to starting and running a scrappy, start-up training program:  The speed and size of the boat, the inexperienced crew, and the need for folks to take on multiple roles while the system was in motion:  All these previous experiences I’ve had building training programs at various organizations related to this one sailing trip.  It made me smile as I turned too far, having given the tiller to a crew member while I jumped up to tack the jib and lock it down, often stepping over crew members who, inexperienced as they were, didn’t know what to do.  

Training programs can be the same thing:  Often, when you start a new program, you are creating training content, delivering the training, scheduling sessions, and maintaining the LMS, all with a smile on your face when you see it work out.  It’s not best practice, it’s not efficient, and it’s often not scalable, but it’s working well enough until you can get the program properly staffed and working like a well-oiled machine.  But there are some pitfalls too, which we need to discuss.  So, let’s look at how the mechanics of Training can relate to Sailing, and vice versa. 

01

Prep For The Environment:  KNow Your LImits

This last sailing trip was in heavy winds for a small sailboat, requiring reefed sails for safety.  Could we have sailed under full sail?  Possibly, but if you put too much stress on the rigging from too much sail, you can snap the rigging and the mast, leaving you dead in the water, as best.  Preparing for the environment means knowing when you need to reef your sails to shrink your sail area for safety, and when even just using a mainsail or jib is all you need.  You can’t move as fast, but it’s safer, easier to handle, and doesn’t freak out your crew.  

For training, this means understanding your capacity.  No instructor should have more than 16-20 people in their class if you want your class to be well prepared.  Everyone needs to have the materials (if you provide them), and all lab environments should be prepped days in advance.  

Could you have 30-40 people in class, or 170-500 like lecture halls in college?  Well, let me ask you a question:  in your lecture hall, how many people asked a question of the professor?  Could you?  I’m willing to bet, if your experience was anything like mine, you could not.  The professor just couldn’t manage that type of experience.  No matter how many people are begging, they will not have a good experience if you overload a class.  Period.  If this becomes a regular problem, you probably need to hire more trainers to manage capacity (or start a Partner Training program).   

02

Establish Your Process:  Know Next Steps

Sailing a boat isn’t like motoring a boat:  you need to have momentum from the sail to get going, which means you need to be angled correctly against the wind.  Sometimes this means you need to tack several times to get where you are going, moving back and forth.  This means you need to organize the tiller movement, the filling of the sail, and unlocking/locking your jib (if it’s not self-tacking).  A lot is going on, and if you are not familiar, it can take you some time to get things set up right for successful forward movement.  Knowing your process, your lines, and getting the timing down is key.  

Process and mechanics apply to everything, and most definitely that includes training.  Make sure you follow your established processes, ideally documented, and have everyone on the team follow them.  If you don’t have established processes, but wing it every single time, it will stress everyone out and impact the training experience for learners.  

You need to have a solid registration process and a way to track registration.  Know how to add folks to your lab environment, distribute training materials, and provide meeting links if remotely taught.  A good Training Coordinator is a lifesaver in these scenarios, keeping track of everything, documenting processes, and establishing routines that make training a joy for those delivering.  

03

Short-Handed Struggles:  It Works, but not Well

Is single-handed sailing possible?  Provided the lines are properly set up for single-handed sailing, absolutely!  The sailboat we had put the winches too far forward, making it difficult to keep a hand on the tiller and winch in the jib.  Usually, I have a couple of crew members who take a winch each, which makes it easier, helping the sailing experience and making it more enjoyable with smooth tacks.  Without that help, I’ve got to trust the tiller to the crew who may not have experience, and often sends us too far to one side or the other.  It takes patience and understanding to manage this on your own with bodies in the way.  

Training can be the same, particularly for a scrappy start-up.  Leadership might think that a single manager can create training, deliver it, keep it all up to date, and manage registrations and course prep, all without breaking a sweat.  For really small start-ups, that’s possible if you are delivering training once a month.  Any more than that, you need to get some staff.  

Curriculum developers specialize in building out your content so that it best relates to the needs of the learner while making the training experience enjoyable.  They need to be aware of cognitive load, prerequisites, constructivist learning, and the whole works.  Content isn’t just about slides: it’s about making sure the structure and content support excellent delivery. 

Trainers excel at the delivery arts and performance that is leading training.  They know how to relate to the learners, provide experiences that help learners connect the dots faster, and answer questions from their own experiences.  Some can be excellent curriculum developers; most are not.  They don’t know, or care, about design; they are all about the art of delivery.  

Operations management is a whole different beast.  You need good people to understand who organizes office space for classrooms, links, and Zoom rooms needed for class, registration requirements, and training material logistics.  Could they teach?  Perhaps, but I’d rather they focus on operations and keeping the training engine running smoothly.  A good Operations person and make a successful training program.  

04

Forcing The Passage:  Your Judgement Impacts The System

I wanted my crew members to enjoy the sail:  I wanted them to love it as much as I do.  I talked it up prior to the day, I hinted at the practicality of the experience, I talked about theory, and the joy of just being out on the water.  Then, when we got out there, I worked my tail off to make it as effortless as possible for them.  Did it work?  Well, a lot was missing from the experience because of a lack of knowledge.  The crew wasn’t properly prepared (there wasn’t time), and we went anyway.  If I had it to do all over again, I would have taken some time and trained them on the mechanics of sailing, so they understood what I was doing and why, even if I still did it myself.  

Training experiences are impacted by so many different things:  Environment, content quality, delivery quality, and learners having completed prerequisites.  If one thing is off, you don’t get that sweet spot.  To be honest, when you are short-handedly delivering training, that’s going to happen a lot.  Training sweet spots, like hitting a perfect close-haul on the ocean, require everything to be aligned.  

Sometimes it’s best to put things off, provide more time, so that the experience is better for everyone.  You may think loading down a class or adding folks from that high-profile customer into an advanced class without a basic understanding is good customer service.  It’s not.  It’s the worst thing you can do for your customers, and taints the reputation and quality of your program. 

Sailboats on San Diego Bay.

Learning the Lines

Proper planning, well-prepared teams, and good judgment can make all the difference in your training program.  Prepare well, have a good support system in the back end, and you are looking at some smooth sailing in the sweet spot, tasting the salty spray and feeling the breeze.  

 

Building Your L&D Team

As I become more familiar with the landscape of business organizations, particularly those who are still in start-up mode, I find that Learning and Development is often an afterthought, something that becomes a necessity because 

  • The Support team is getting overwhelmed by customers who have simple requests they, the customer, could do themselves.
  • The Customer Success team has customers that don’t know how their product or service works, or how to utilize it.
  • The Professional Services/Deployment/Implementation teams spend a lot of time giving introductory walkthroughs of the product as “training”
  • Angry CEOs are contacting the CEO of your company to ask why you don’t have training.
  • Industry comparison publications outline the lack of training as a “con” for using your product/service.

Ultimately, for whatever reason, the decision is to build a training program. So leadership with little or no experience in Learning and Development starts to hire folks similar to their teams and use them as “trainers” because their product/service is intuitive, right? Training can’t be that hard. 

Here’s the thing:  Training isn’t Engineering, it’s not Sales, and it’s not PowerPoint slides.  There are whole disciplines dedicated to analyzing, creating, and delivering training.  Advanced degrees are dedicated to best-communicating information in such a way that it sticks.  You need a team that knows how to organize, deploy, and manage all phases of the training organization to be successful.  You need a Learning and Development organization.  So let’s talk about each role within that organization, so there’s a better understanding of how that works.  

For context, I will be talking about the fundamental structure of a Director, Managers, and Independent Contributors in a scaled-down organization expected for a reasonably successful, mature organization.  You could have more directors, more managers, VPs, etc. as your reach expands and the scope of learning expands, all the way up to a Chief Learning Officer who directs the development of internal and external learning.  Though, if you are reading this, you are likely not looking for a CLO, but rather an idea of where to start with your training organization.  So, let’s start with the basics.  


Except that training isn’t PowerPoints, but skills that take skilled professionals.

Image of woman with hat

Curriculum Development

Curriculum development is the process of analyzing the jobs, tasks, subtasks, skills, etc. necessary to be successful and compiling that information in a narrative form that layers skills from foundational to knowledgeable.  Curriculum developers know how to work with Engineering, Product Management, Product Marketing, Marketing, Sales, and Support to do their analysis.  They design the course based on the Jobs, Tasks, Subtasks, Skills, Knowledge, and Approaches necessary to be successful.  They develop the training in the medium(s) necessary for delivery.  They implement by using alpha runs to get a feel of the content, betas to get the feel of the delivery, and then go live and evaluate the results.  

Role KPIs

A good curriculum developer will have the following KPIs:

  • Customer Satisfaction:  Is the learner happy with the content and what they have learned?
  • Net Promoter Score:  Would the learner recommend the course to friends and colleagues? 
  • Course Completion:  Are learners who register to complete the course?
  • Exam Pass Rate:  If there is an associated exam, are people passing the exam At a minimum 70% of the time?
  • Customer Success:  Are learners more confident in their role after taking the training?

A curriculum development team will, ideally, own one product or suite at a time, so they can maintain expertise in that content.  Additional roles that can sub-divide Curriculum Development would be eLearning specialists and media production specialists. 

Image of man with hat

Trainers

Trainers, be they technical or not, deliver the training as created by the curriculum developers, placing the content within the context of the learners.  Their job is to assess the capabilities of their learners and help them best understand the content through related experiences and a certain amount of showmanship (some “dad jokes” thrown in can be helpful, too!).  It’s all about reading the room, getting a sense of the levels of understanding, and helping everyone feel confident in the content they have learned.  Where curriculum developers are writing their curriculum for everyone with a foundational knowledge level, trainers tailor that content to Bob and Charlene in class, helping Bob with some missing foundational knowledge while drawing on Charlene’s advanced experience to help explain more complex concepts.  

Role KPIs

A good trainer will have the following KPIs:

  • Customer Satisfaction:  Is the learner happy with the content and what they have learned?
  • Net Promoter Score:  Would the learner recommend the course to friends and colleagues?
  • Utilization:  How many classes does the trainer deliver in a week/month/quarter?
  • Scope:  How many courses can the trainer deliver?
  • Innovation: In what ways has the delivery of the content gotten better over time?
  • Customer Success: Are learners more confident in their role after taking the training?

The Training team can be further subdivided into varying levels, depending on experience, competency, and increased scope.  

Image of man with glasses drinking coffee

Exam Writers

Exam writers will use their understanding of the job tasks to build exams that test the ability to accomplish a particular job.  While this is somewhat similar to curriculum development, it is a completely different skill.  Curriculum development focuses on teaching the skills necessary to complete a job.  Exams test whether or not someone, at their level of understanding, is capable of completing a job.  Exams can be completely independent of training, and training can be conducted without requiring exams.  

It should also be noted that exams are different than review questions or class assessments (quizzes) to test understanding.  Those two methods are used by Trainers to evaluate how well the course is going and to determine if there needs to be a course correction during the class to make sure all content is fully understood and learned.  Exams, however, focus entirely on whether or not someone has the necessary competence to complete a task or job.  

Role KPIs

A good exam writer would have the following KPIs:

  • Exam Completion:  What percentage of learners completed the exam after starting it?
  • Exam Pass Rate:  How many learners passed the exam, with a pass rate target of around 70%?
  • Writing Errors:  How many errors does the exam contain?
  •  Exam Relevance:  How relevant is the exam to the role against which the exam is testing?

Exam writers can fall within a whole category that works with Operations, depending on how the exams are delivered and results are recorded.  Industry-standard exams need to be legally defensible in court, meaning if any discrepancy in the results due to incorrect answers, overly ambiguous questions or answers, or out-of-date questions that are no longer relevant to the job, companies can be liable.  In some small organizations, the curriculum developer can also be an exam writer, though this is not ideal.  

Group of people working in the office

Training Operations

Training Operations is an umbrella term that includes a lot of different folks, and I place them together because their roles are specialized and are often combined into one or two people.  These roles include 

  • Training Coordinators:  These unsung heroes schedule training, assign instructors, bill learners, and answer all questions learners may have that are not topic-specific, like whether or not a service dog is allowed in class.  Whether or not you have live only, a mix of live and on-demand, or on-demand-only training, you will need someone to manage this part of the business.  It can be the training manager or a coordinator hired specifically for the role. 
  • LMS Admins:  Your Learning Management System administrator is your rock.  Nothing can happen without this person managing the environment through which you schedule and/or deliver your training.  Without your administrator, you would be running all training through Excel and Outlook, which is a recipe for disaster.  If you don’t have a Learning Management system, get one.  If you have one, make sure your admin is well taken care of.  
  • Training Marketing:  Once you have training out there, you need it marketed.  Whether you use the company Marketing team or you have a dedicated team/person in charge of marketing for your courses, if you don’t get the word out, you don’t get sign-ups.  
  • Training Sales:  If you are a P&L (Profit and Loss) department, you need to have dedicated sales teams.  Now, I know what you are thinking, “but I can just have our existing Sales team sell training, and that will work!”  No, it won’t.  This is why:  Training is an “add-on” that main Sales teams will cut in a heartbeat to get a bigger deal through and make it look like a discount.  No remorse, no second thought to the lack of training available for the customer and the inability to an effective implementation of the product/service.  Salesfolks don’t care about the customer’s implementation, they care about the deal and their commission from that deal.  If approvals are required, they will try to get around the approvals.  If Training Management approvals are required, they will go to senior executives.  I’ve seen it time and time again:  Every time a Training Sales team is rolled into the main Sales organization, Training revenues take a nose-dive.  Have dedicated sales teams for your Training, if you are selling training.  Period.  
  • Custom Enablement Training:  Large-scale training courses for user-level training may be required for your product/service if your product/service changes the way people work.  This is part of change management and should be regarded as necessary because it’s very likely that your customer is not going to provide this level of product enablement for their customers. 

There are probably several other roles I could add here, but they all become more valuable as your teams get bigger, and that’s a discussion for another post.  ^_^

Man with beanie

Management LEvel

Management of your training organization depends on the number of people on the team.  You could have one manager/director who is in charge of a few curriculum developers and trainers.  You could have a hierarchy of leadership from the CLO to SVPs to VPs to Senior Directors to Directors to Senior Managers to Managers, each managing several directs that make sense for your command structure.  My leadership design starts with two levels:  The Director, and the Independent Contributor.  

The Director

The L&D Director outlines the direction of the training program and the expectations of each role. If the team is less than 10 people altogether, then the Director can manage everyone effectively, even if they break them up into teams (Curriculum, Training, etc).  The Director can then outline their expectations to the teams, and manage any requirements for that team as necessary.  

The Independent Contributor

Independent Contributors are all the roles above (curriculum, training, etc) that have tasks to do and generally work directly with their customers.  They create the content and scope as directed by the Director, and execute the vision.  

Expanding the Leadership Team: Managers

If the team becomes larger than can be effectively managed (the general threshold is 10 ICs to one Leader), then the Director may want to hire Managers for their ICs.  Managers follow the direction as set by the Director, and manage the needs of their ICs by removing barriers that get in the way of their work.  As their teams grow (again, more than 10 ICs per leader) or different regions require more specialized knowledge, additional Managers can be hired.

Expanding Up:  More Directors

Additional Directors may be needed once the growth of the team becomes so large that each group and vision need to be addressed separately.  This usually happens once a company moves from Mid-sized to Corporate levels, with larger teams.  It also happens when Learning and Development teams start to consolidate around single visions and leaders, (i.e., a Chief Learning Officer), in which case each specialized learning area needs direction and execution (think Sales Enablement vs. New Hire vs. Customer vs. Partner enablement).  At this point, you may have Senior Directors, VPs, Senior VPs, etc. that execute the vision, scope, and direction based on specific needs.  

Now, if you are reading this, you likely are not at this point, so why bring it up?  Because you might be someday, and you want to be ready.  You will want to know how to scale your organization effectively or have someone who can scale it for you, and what that will entail.  

 

Structuring Your First Training Organization

The first step you need to make is to hire a good Director that knows how to build a training organization, because, likely, your existing leadership isn’t aware of how to do that.  They may be excellent Sales folks, know Customer Success well, or know how Engineering works, but they are going to look for Sales, Customer Success, or Engineering leaders.  You need to find someone who knows how Training and Development work, has had experience with the process, and has, ideally, built a training program at one point or another in the past.  

Once you know you have someone who can do the job, you need to let them do the job.  Don’t short-change them on people, resources, software, etc.  Good training can be created in PowerPoint, that’s true, but it limits engagement compared to a strong LMS, excellent social learning platforms, and AI-driven learning paths.  Don’t break the budget, but make sure you have the key roles in place for the scope of your need: 

  • One curriculum developer for each product/service family
  • One trainer per 4 training days a week
  • A coordinator to maintain a lot of the operational stuff
  • An LMS Admin (could be the Director/Manager) to keep the lights on.

Additional roles can be added, negotiated, etc. as necessary.  

Common Pitfall

Now, the common pitfall I see small companies make when they want to start training but don’t want to invest too much is to hire one person to do everything.  There’s the problem with it: 

  • Direction then has to come from people who don’t understand training or how it’s developed:  they don’t have the experience, and they fail to understand why the training team just doesn’t “create a PowerPoint” for training.  
  • Curriculum Development is time-consuming:  With full analysis time, it takes 40 hours of development time per 1 hour of delivery.  One full week to have content ready for one hours-worth of training.  Even if you have analysis taken care of, it can take one day to create the content for one hour.  That means the curriculum developer isn’t able to deliver the training while they are developing the next course.  They will get behind in their development, and the courses will quickly become outdated. 
  • Burnout:  That one person will burn out very quickly if they have to run everything because they can’t scale.  Even with on-demand training, there’s no way to scale the content creation, maintenance, delivery, and exam writing necessary to make a successful training program.  You have crippled your training program before it’s had a chance to grow.  

Take it from someone who has been in this position as their peers were released for various reasons and I became the last man standing:  It doesn’t work, and it makes the training guy look like an idiot that can’t do the work, regardless of their credentials.  It’s poor management, so don’t be caught in that trap.  

Final Comments

Designing a good, solid training program that can scale can be daunting if you don’t have the experience, so hopefully this guide has given you an idea of what that structure should look like. If you have any questions or are looking for help in building out your training program, don’t hesitate to reach out so we can help! 

2.6x More Productive

Employees who trust their leaders are 2.6 times more productive on tasks, bringing more value to the team!


41% Lower Absenteeism

Employees who trust their leaders are more likely to show up, be engaged, and stay engaged.  


50% Less Likely to shop for another job

Employees who trust their leadership are more likely to stay where they are and grow in their roles, rather than shop around for other positions or companies. 


Safety Motivation: 

Does your Team trust You?

Why You Need To Build Trust

We have all been there at one point or another in our careers.  A leader comes into a new position, starts making changes, and the layoffs start.  I’ve seen this happen to other teams, and to my own team.  The results are painful to watch.  The remaining team members just keep their heads down, doing what they are told.  Feedback isn’t taken, feedback isn’t wanted, and no one wants to give the new boss a reason to let them go before they are ready.  Resumes are flying, and soon the team starts to lose members all over the place. 

In the case of really good, quality organizations, leaders that cause this type of disruption for the sake of disruption are let go (I’ve seen this happen twice).  For those organizations that are not quality, they let their best people go, hire new people, and start a cycle of high turnover.  It’s not pretty, and it could all be avoided if leadership took the time to build trust.  

Trust Makes Good Teams

Trusting employees are 260% more motivated to work, have 41% lower rates of absenteeism, and are 50% less likely to look for another job (Reichheld & Dunlop, 2023).  Teams that are able to trust their leadership build better relationships, and are free to create a social structure that is strong, inclusive, and supportive of each other.  Trust satisfies the Safety need in Maslow’s hierarchy of needs, and is itself a foundational need only superseded by the need for survival.  Without it, all other motivational methods are rendered useless.

Distrust Is More Rampant Than You Think

The numbers are grim: roughly 1 in 4 workers don’t trust their employer. At the same time, most employers overestimate their workforce’s trust level by almost 40% (Reichheld & Dunlop, 2023).  That’s right; in most organizations a full quarter of your workforce doesn’t trust you as leadership.  What’s more, you likely overestimate the amount of trust you have because, as an untrusting body, your employees are not going to tell you they don’t trust you for fear of retribution.  

Build Your Trust Now

It’s often been said, you build trust in drops, lose trust in buckets.  If you have a team that doesn’t trust you or your leadership, you have a long row to hoe.  You can either say a lot of words and hope they will believe you (spoiler alert:  they won’t), or you can get to work.  Here’s how you build trust. 

  • Be Empathetic: Know your team and listen to understand.  Your team is going to say things, even if they don’t trust you.  They will tell you there are problems, even if you don’t want to hear them.  Actively listen and try to understand the problem.  Don’t dismiss concerns, listen.  Don’t try to fix anything, listen.  Don’t try to second-guess their problem and come with a solution, LISTEN.  Once you fully understand the concern, circle back around with the team and discuss solutions AND GET THEIR INPUT.  
  • Be Compassionate:  Actively advocate for your team and alleviate their challenges.  Trust that people are basically good, and when given the chance will do all they can to be the best at what they do.  Work to remove obstacles, work round them, or build solutions with the team to make things better.
  • Be Honest:  Transparency and honesty are respected, even if the team doesn’t hear what they want to hear.  There will be bad times.  There may be some folks that will need to leave because of performance issues or attitude issues.  There may be lay-offs that are necessary because projects vary, come to an end, or economics mean demand has gone down.  Show that you understand their concerns, be straight-up honest about why people are being let go (when legally possible), and explain how a decision was trickled down to them.  
  • Be Honorable:  If you say you are going do to something, do it.  If you tell people that there will be no lay-offs, keep your word.  If you promise training and career development options, don’t exclude anyone.  The minute you break your word, you are no longer trustworthy.  

“A full quarter of your employees doesn’t trust you as leadership.”

  • Be Empathetic: Know your team and listen to understand
  • Be Compassionate:  Actively advocate for your team and alleviate their challenges
  • Be Honest:  Transparency and honesty are respected
  • Be Honorable:  If you say you are going do to something, do it

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Everyone is talking about AI, though they generally mean Generative AI.  While GenAI will likely have a huge impact on Learning and Development, I’d like to explore the impacts of Analytical, or Behavioral, AI.  Behavioral AI is the sleeping giant of Narrow AI applications, and will likely have a larger impact on our lives and business than Generative AI.  But how will it impact training?