Month: August 2025

Building An Engaging Learning Program

  • Strategic Alignment & Needs Assessment
  • Design for Impact & Engagement
  • Implementation & Support
  • Measurement, Evaluation & Evolution

 

 

Beyond Training – Towards Transformation

We’ve all been there; we’ve sat in those classes.  Training for training’s sake, little was gained, but boxes are checked, and we return to the daily grind without applying anything.  This is an all-too-common scenario in many employee enablement attempts.  Disengaged learners, burnt-out instructors, or “trainers” who think reading from the PowerPoint is sufficient.  

The thing is, it doesn’t have to be this way.  Training is a skill multiplier when applied correctly through an effective learning program.  Learners want to attend training because they know what they are getting: skills to help them succeed.  Trainers who deliver the content are engaged because it’s not the PowerPoint that motivates them; it’s the message.  They sell it because they believe it.  Proper training and well-designed learning plans drive real, measurable change.  

What’s more, it’s not that hard to have effective learning programs.  Start with

  • Strategic Alignment & Needs Assessment
  • Design for Impact & Engagement
  • Implement & Support your Plan
  • Measure, Evaluate, and Evolve 

Let’s explore each one.  

Strategic Alignment & Needs Assessment

You are probably thinking, “Well, yeah, of course we should be strategically aligned!” And you would be right!  But “should be” and “are” is a journey that isn’t always so clear to navigate.  So let’s map it out and clear the process up. 

Define “Moving the Needle”

What does it mean to “Move the Needle?”  It means that, whatever your training plans are, they should tie directly to measurable business objectives.  You may want to train more people to use a particular aspect of your product.  Why?  Because, in using that aspect of your product, they are more tied to the product itself, and less likely to churn.  You want people to follow a specific process while using the product.  Why?  Because it reduces the number of support tickets that come in, which then means better customer satisfaction.  Training can directly impact the business when it’s tied to business outcomes.

Identify Performance Gaps

Now that you know what you need to change and how training is going to create an impact, you need to know what needs to be taught.  This means conducting a thorough needs assessment.  Conduct interviews, run surveys, look at performance data, and analyze for obvious gaps.  You want to know what needs to be taught to meet your business objectives.  

Once complete, you need to organize the content to distinguish between skills, knowledge, and motivational issues.  When I build out my analysis data, I organize it by 

  • Job:  The job contains several tasks that need to be performed.
    • Tasks: The tasks that are needed for the successful completion of the job.  Each Task has several subtasks.
      • Subtasks:  Subtasks are the tasks needed to complete a Task, and are, themselves, made up of several components. 
        • Skills:  The job skill is executed to a degree of accuracy that completes a subtask.
        • Knowledge: Knowledge is the information needed to implement a skill accurately.
        • Motivation: The approach to applying knowledge and executing the skill.  Often this is called Attitudes, or Mindset.  

This logical breakdown serves two purposes: 

  1. Building a database of skill sets needed for every class that can be written up and easily transferred
  2. Logically structuring the content for delivery 
    1. Job: The Course
    2. Tasks: Modules
    3. Subtasks: Sections
    4. SKM: Paragraphs

BONUS Benefit:  HR now has clear skill sets for job requisitions and onboarding.  

Target Audience Analysis

Now that you know what needs to be taught, you need to understand who needs to learn.  Target audience analysis helps you identify your personas, the level of skill needed for a particular job, and the depth of knowledge needed to complete the job.  

  • Are you addressing Leadership and business outcomes, or Engineers and processes?  
  • Do you need to position the skill for new learners that need more detailed walkthroughs and explanations, or for more advanced learners who need to see context, connections, and cross-functional applications?  
  • Do your learners learn best through lectures, games, and challenges, or tactile labs and milestones?  
  • Can your learners dedicate a full week off the job to training, or do you need to break up your training into 1-hour sessions spread across 8-12 weeks?  

How your learners can engage will determine how well they engage in your delivery. 

Finally, you need to understand your learner’s motivations.  Do they want to learn new skills, or are they being made to learn new skills?  This can heavily impact the success of the training. 

Design for Impact & Engagement

Outcome-Based Curriculum Design

Too often, when training needs to be built, we start with a workflow and focus on features.  For large products that apply to many different industries, this might work, but even then, you have a desired outcome for the course.  Designing your course from the desired results and behaviors first, then working on the content to support it, keeps the training on course.  The outcome is always in sight; it’s woven into the content delivery, instructions, and processes presented.  

There should also be a focus on application, rather than memorization.  25% of all lecture content is retained short-term, while only 7-9% is retained in long-term memory. That’s not a lot!  Your training should be focused on applying skills, not memorizing steps or facts.  

  • For technical training, this means doing labs.  
  • For onboarding, this would mean simulating your experience.  
  • For Leadership, this would mean a cohort training session where skills are applied during the weekly course, and then “homework” is assigned where skills are exercised in real scenarios to be reported on later.  

Engage through applying skills, connecting skills to similar life experiences, and showing how the result is relevant to their needs.

Diverse Learning Modalities

There is no one right way to build and deliver training, so use them all!  Utilize microlearning, workshops, coaching sessions, experiential learning, and self-paced learning to cater to a wide array of learning needs.  Encourage engagement by meeting your learners where they are most comfortable.  Do they need a live class to stay on task?  Offer one!  Are they more comfortable with self-paced learning? Make it available!  Are they too busy to attend a single bootcamp?  Design a cohort track spread over several weeks!  Are they neurodivergent and in need of options to better support their comfort levels?  How can you say no?  Some topics and content lend themselves to one delivery methodology better than others, but never use just one.  

Engaging Content & Delivery

Engaging content contains real examples from real scenarios and is designed to be interactive.  When building your workflows, build them off of examples that your learners will experience in the field.  Then, create an interactive component.  If it’s technical learning, have them build it out in the platform.  If it’s leadership, run role-play scenarios and assign tasks to apply while working.  Looking to build or enhance skill sets for your struggling employees?  Run employee cohort sessions where best practices can be applied immediately after a session, and then reported on the next time you meet.  The closer to real-world experiences you can give your learners, the more they will retain.  

Every training should tell a story:  The story of the workflow (Why are we doing what we are doing?), the story of the examples (why would someone do this?), and the story of the outcome (who benefits and why?).  Stories with relatable examples encourage learners to build on their existing experience, helping them connect the dots to the existing processes.  

Clear, concise communication is critical to success.  This, personally, is a challenge for me:  I tend to be very verbose in writing and while teaching.  Industry acronyms, jargon, or buzzwords are tempting, but ultimately undermine your training.  Avoid anything that would get in the way of your learners quickly absorbing and applying the concepts you are teaching.  Remember, cognitive load is a very real thing:  Don’t add to it unnecessarily!  

A sample of what training programs can be created.

Virtual Presence Robots in the Classroom
Virtual Presence Robots in the Classroom

Implementation & Support

Pilot & Iterate

Now you have your plan, you’ve laid the keel, and you built the course.  You are ready to get it out in the wild and see what she can do.  You are ready to implement.  

Implementation is, just like with anything else, a phased process.  You want to start with your Alpha run:  teaching internally and to a select few outsiders so you can get the feel of the course.  Ask some key questions: 

  • Did the course hit all the right notes? 
  • How did it flow?  Does it make sense as you move from one concept to another?
  • Are there any gaps or barriers in the delivery or content that was an irritation or a frustration to the overall course? 

The Alpha run is very much a chance to shake down the course.  You want to work out any bugs before you place your content before your customers. 

The next step would be to run a Beta.  Unlike the Alpha, which is generally run with a near (but not complete) course, the Beta is a run with a course that is, essentially, complete.  You are now training your key instructors and partners on how to deliver the course, and they see it in action.  Sometimes key customers will be included if you need feedback from a customer standpoint, and is often recommended when you have strong customers that are willing and eager to contribute to the success of your platform.  And, of course, you iterate with each delivery: Work out what landed well and what doesn’t.  

Leadership Buy-in & Support

Now that you have a course that’s ready for prime-time, you need executive buy-in and support.  For internal training, this means Leadership needs to be on board with the message and skills being delivered, know what behaviors are expected after training is delivered, and reinforce those behaviors in the wild.  If leadership doesn’t support, or outright dismisses, your training, it will not have the impact for which it was designed.    

Create a Supportive Learning Environment

Learning is the practice of failing, and trying again.  If you don’t feel safe in failing, you can never truly learn.  Every training should provide a safe space for practice and failure.  Learners will get frustrated, learners will find they are behind.  They need to know that they will not be judged for the pace at which they learn.  

This also applies to learning methodologies and preferences.  Some learners will prefer self-paced over in-class, because they can take their time and/or they don’t have others waiting on them to complete the process.  There’s a level of psychological safety in being able to learn in your particular learning style and preferred methodology.  

Measurement, Evaluation & Evolution

Kirkpatrick’s Levels of Evaluation (Simplified)

I’m a big fan of having key measurements for success:  It’s easier to reference when you are looking for success in a training platform, and it provides foundational references to the value training is bringing to the table.  The thing is, you can’t comprehensively measure the success of training during class:  You can’t scan the learner’s brain and identify the skills they acquired.  You need to work with other teams to identify how training has made an impact.  

Fortunately, Kirkpatrick’s 4 Levels of Evaluation make things easy.  

  • Reaction: Did learners like it? Do they see the value in what you are learning?  These questions you can ask with your closing survey.  Be cautious though:  Don’t just look at the responses you got, look at the number of responses you didn’t get.  Ideally, you should be aiming for a 60% response rate for your closing course survey.  Anything lower than that, I would be suspicious on the accuracy of the satisfaction scores.
  • Learning: Did they gain knowledge/skills? Depending on your course design, you can use quizzes, assessments, or reviews to evaluate if they have learned something during the class.  This will test their short-term memory, in which at least 25% of a lecture will be captured.  Long-term memory usually hovers around 7-9%, and will require some additional study and practice to ingrain behaviors into habits.  An excellent long-term learning measurement would be certification exams.  
  • Behavior: Did their behavior change on the job? When creating internal training, this is an easy measurement point:  Are learners performing better against their KPIs?  Are they performing faster, more accurately, or correctly in their tasks?  Managers can easily measure this result and report back on the results.  Customers, on the other hand, go back to their jobs and behavior is much more difficult to measure.  If you do not have a direct way to measure, you can use conversations with your key Customer contacts and the Customer Success team to determine if behaviors changed with those who attended.  
  • Results: Did it impact business outcomes? Internally, this is an easy metric.  Are KPIs improving?  Do we see reduced waste and increased performance?  Managers are already measuring job performance through KPIs, and those KPIs should be directly tied to ROI. Better KPI performance should increase ROI of the training program.  Customers, on the other hand, require interaction with the CSMs, though their general Account Health will be the determining factor:  Did training customers increase customer loyalty and dependence on your product?  

Data-Driven Decisions

Now that you can measure your success, look at the data.  Identify what works, and what doesn’t.  Customer Satisfaction of the course will let you know if the course flows well and answers the questions the learners had.  Course quizzes, exams, and lab completion scores will indicate if the learner is, well, learning and retaining key concepts short-term.  Improved performance and task completion will identify that behavior is changing, and increased KPI results and better account health will indicate the results are promising.  Watch these metrics, tweak when necessary, and watch again.  All course development should be iterative.  

Communicate Success

If things are going well, communicate it out!  Let Leadership know what CSAT scores are being generated, learner comments, and measured behavioral changes and results.  Let your Stakeholders know how their input has made a material difference in the learner, the organization, and the company.  

The Continuous Journey of Learning Excellence

We’ve made quite the journey on this process, navigating key points that help you move the needle when developing your training platform. By starting with Strategic Alignment & Needs Assessment, you have a superstructure of training that meets the needs of the learner and ties back to key business objectives and desired outcomes.  When youDesign for Impact & Engagement, you are building a course that will engage your learners throughout the process, tie back to their previous experiences when necessary, and show them the value of the content and outcomes desired. Then, with Implementation & Support, you are taking your course live through it’s iterative process, evaluating and adjusting as necessary for success.  Finally, with Measurement, Evaluation & Evolution, you track the value being added through training.  Each phase is a valuable port of call as you navigate your learning program. 

 

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 Bounty, and 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.