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7 Ways to Make Leadership Training Stick

Talent is everything. Any leader can tell you that.

According to DDI’s Global Leadership Forecast for 2021, three of the four top CEO challenges for 2021 are talent related.

Yet according to that same study, bench strength is at an all-time low. Only 11% of heads of HR departments say they have a strong bench to fill leadership roles compared to (an already dismal) 18% in 2011. (And don't even get me started on the fact that 26% of CEOs say they can't find a compelling purpose for their organization. Yikes!)

In the past decade, there has been a dramatic increase in the volatility of both markets and the external environment. There’s more pressure to innovate. More pressure to re-prioritize. More pressure to operate in conditions of complexity, uncertainty and ambiguity.

What’s a leader to do? Well, train their leaders of course!

That’s why global spending on employee training was estimated to be $370 billion in 2019.

Yet despite this expenditure, most companies don’t see long-term benefit at either the individual or organization levels. In other words, there’s little to no ROI on training and education. Harvard researchers Michael Beer, Magnus Finstrom and Derek Schrader call this phenomenon The Great Training Robbery, which is in my opinion, the greatest title for an academic paper ever conceived.

Companies spend all that money, and yet nothing sticks. It sucks up time and in the worst cases, succeeds only in increasing organizational cynicism. Not the result we’re looking for.

What’s to be done? Lots of things.

I’ve identified seven key factors that ensure that leadership training sticks:

1. Get Senior Leadership Buy-in

A few years ago, as a part of the Unstuck Project, I interviewed 42 graduates of Seth Godin’s excellent altMBA program. I learned that within a year of completing the course, nearly half of them were looking for a new job.


Because their new Godin-shaped values and knowledge were no longer in alignment with the organizations they worked for. Talk about poor ROI for the companies that paid the very expensive altMBA tuition.

This is why leaders absolutely must be a part of the solution, and not simply outsource it to an outside person, even if that person is the very impressive Seth Godin.

In the world of systems leadership theory, this outsourcing of training responsibility is called “Shifting the Burden”. It’s a terrible trap to fall into because it’s based on the faulty assumption that organizations function as the sum of the various talents of the individuals working within them. Just train enough people, and their collective skills and knowledge will add up to organizational success. In reality though, training doesn’t just add up. It’s affected by the complex system of humans, resources, processes and interactions that make up any organization. These systems are bigger than any individual, no matter how well trained or inspired they are.

That’s why training only succeeds when senior leaders “show up” for the change they’re seeking.

Training must be embedded in a highly visible, senior team-led, system-wide change effort. Before I commit to working with an organization, I seek to confirm that the concepts I explore in the training are consistent with the desired state senior leadership envisions and is working toward achieving.

Before training begins, I reach out to each participant’s boss. I offer to hop on a call to explain the training and answer any questions they might have. I also ask them to tell me about the employees who will be in session with me – their strengths, areas for development and anything else they should know.

2. Prime the Pump for Trust

How many times have you stepped into a real or virtual training room without any knowledge of who the trainer is, much less any sort of understanding of their personality or how they intend to interact with you and the rest of the trainee group?

When this happens, the trainer begins with a massive deficit. There’s not only a lack of trust, but probably a hint of distrust because to the trainees, this person will have no understanding of who they are, what they do, or how their organization operates.

So, what does the trainer do? You guessed it - twenty minutes of round the table introductions usually followed by some kind of ice-breaker question.


What a waste of time.

And, what a waste of an opportunity to build trust.

My training programs begin long before the first formal session. I send an introductory email a week or two in advance in which I introduce myself and outline what we will be doing together over the weeks to come. Then I ask each participant to tell me about the things they’d like to achieve, learn or explore during our time together. I ask them to tell me about their employees and their strengths and weaknesses. I ask them to complete a six human needs scorecard. And I ask for their home address so I can send them a copy of my book, The Unstuck Leader.

When they send back their responses, I reply with validation, encouragement and additional resources they might find useful. Sometimes, I’ll give them a question to mull over. If they respond, I’ll keep the conversation going.

By the time we enter the training room, it feels like we’re, if not old friends, then at least mutually interested and respectful acquaintances. They know I know a little about them and the challenges they’re facing. And they know I’m a pleasant, friendly kind of person with a taste for silly puns.

And guess what that leads to?


And that means our first formal session will be more open and relaxed. The trainees will be more likely to speak out when I ask questions or interrupt me with questions of their own (which I love and encourage whole heartedly).

No time is wasted. We get straight to the good stuff.

3. Make it Relevant and Personal

Training that isn’t relevant and personal is dull and boring. It washes over a trainee with very little actual processing of information.

I aim to keep the content fun and engaging. I deliver new frameworks and methodology. They haven’t read my content in a book, or on HBR. It’s novel. And novelty triggers a dopamine hit to the brain that increases retention and creates a desire for more learning. It becomes very relevant.

As the course progresses, I continue my one-on-one relationship with each of the trainees. They submit bi-weekly homework assignments in which they reflect on themselves, their employees and the things they need to do to grow into expansive leaders. They receive a detailed response with me including suggestions for additional reading, videos or exercises.

Each participant also receives two or more hours of individual coaching with me. This enables us to dig deeply into leadership issues they may be facing, and to work toward solutions in real time.

4. Allow for Practice and Mistakes

How about this: you pretend you’re someone called Bob and I’ll pretend I’m someone called Dawn and you’ll have a difficult conversation with me about my nefarious workplace behaviour. We’ll feel deeply uncomfortable as we’re pretending and will either dissolve into giggles or will perfunctorily push through it so we can be done with this torture as soon as possible.


Role playing is silly. There. I said it.

It’s not the kind of practice that derives lasting learning, it’s often infantilizing, and it makes introverts want to crawl out of their skin.

Enough with the role playing. Let's talk about the real world.

My trainees are expected to come to class prepared to discuss a real life management issue they are struggling with. They receive coaching from me and over the duration of the course, they learn to coach each other. This collaborative in-class approach deepens the learnings for everyone in the session and creates bonds that will last for years to come.

5. Make it Symmetric

Have you ever been to an exciting conference or training program only to come back to the office brimming with new and enlightened ideas only to have them met with blank stares? I call it “I’ve been to a conference syndrome” and it’s not fun for the trainee or their colleagues. At its worst, it causes a frustrating disconnect that often increases cynicism on both sides.

Training is only effective if everyone gets it. It has to be symmetric.

In my training programs, symmetry is where the magic really happens. Each session, trainees are assigned a new accountability partner who they will support and be supported by for the next two weeks. Often, the partners have not met and would not work together outside of the training room. These new and non-traditional connections create a cross-divisional network of like-minded leaders.

Everyone goes through the same training. Everyone receives one-on-one coaching.

They begin to share a common leadership vocabulary. They become a true team. And they reinforce their new learnings in each other.

It’s a powerful thing.

6. Build it for Long-term Transformation

The truth is, even with the best instructors and the most engaged students, most learning happens outside the training room.

And that’s because there’s knowledge and there’s knowing.

Knowledge is gained in the classroom. Knowing occurs as we re-wire our brains, through the creation of new synaptic connections through reflection and practice. This allows us to “unwire” old neural pathways and create new ones so that when we’re stressed, we don’t fall back into old, non-productive habits.

By spacing the sessions to every other week, I create a rhythm of learning, reflection and practice that allows these new neural pathways to form.

7. Train Humans for Real Life, not Employees for Competency Frameworks

My programs begin with the premise that leadership isn’t simply about doing the things that great leaders do, but rather about becoming the kind of person who does the things that great leaders do.

Trainees develop a heightened self-awareness and personal courage. They gain the ability to understand those around them, practice the art and science of influence, and are introduced to co-creation and systems thinking methodologies. Finally, they learn how to develop a personal leadership practice that will enable them to lead consistently.

The result of all this is a team of connected, mutually supportive and highly effective leaders who are deeply engaged and committed for the long-term.

In other words, the training sticks.

P.S. If you'd like to learn more about Expansive Leadership training, check out The Center for Expansive Leadership.


The Unstuck Leader book is now available.
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