http://www.ajackedexperience.com/

A Jacked Experience, Toronto, ON (2026)

08/25/2026

LEADERSHIP GAP: We’re experiencing a lot. But are we learning from it?

I was out cycling today and realized how much of my thinking happens when I’m doing something physical.

Walking the dog.
Lifting weights.
Cycling.
Getting outside.

It gives my brain space to process.

It made me think about a conversation I had with a client recently.

At the end of our session, I asked:

“What was most helpful for you today?”

Their answer?

“The realization that I need to take more time to reflect.”

Not more information.

Not another strategy.

Reflection.

And I think this is a bigger leadership gap than we talk about.

We experience SO much as leaders.

Difficult conversations.
Missed expectations.
Conflict.
Feedback.
Wins.
Decisions that didn’t go as planned.

But how often do we actually stop and ask:

What just happened here?

What was my role in it?

What did I assume?

What did I avoid?

What did I notice?

What might I do differently next time?

What did I learn about myself?

Because here’s the thing:

Experience alone doesn’t necessarily make us better leaders.

Processed experience does.

And I think this is especially important for newer leaders who may not yet have developed the habit of stepping outside the situation and observing themselves in it.

But experienced leaders can fall into the same trap.

We have so much experience that we can become very quick to interpret.

“I’ve seen this before.”

“I know what’s happening.”

“They just need…”

And sometimes experience becomes a shortcut around curiosity and reflection.

The irony?

The busier and more senior we become, the more important reflection becomes.

Our teams need answers.

Our organizations need decisions.

There’s always another meeting.

Another deadline.

Another problem to solve.

So who is asking the leader the questions?

“What are you noticing about yourself?”

“What might you be missing?”

“What is this situation teaching you?”

Because without reflection, we can spend years accumulating experience without necessarily evolving from it.

Sometimes stepping away from the doing is where the real learning happens.

Where do you do your best thinking?

08/18/2026

I was working with a senior executive today who wanted to inspire their team to take more ownership.

More accountability for their performance.

More commitment to the collective outcome.

More of that feeling of we're in this together.

We talked about incentives. Accountability. Goals. Team structure.

And then we kept coming back to something much simpler:

How well do you actually know these people?

Not their roles.

Not their strengths.

Not what you've observed about them over the years.

Them.

What matters to them right now?

What motivates them?

What's getting in the way?

What are they seeing that you aren't?

What would make the bigger picture matter more to them?

It got me thinking about a leadership gap I see often, particularly as people become more senior.

Curiosity.

We build our careers on knowing.

Knowing the business.
Knowing the answer.
Knowing what good looks like.
Knowing our people.

And eventually, we can become so used to knowing that we stop asking.

We start filling in the blanks with assumptions.

But knowing someone isn't the same as understanding them.

And the more senior you become, the less you can rely on your ability to know and the more you need to rely on your ability to understand.

People don't necessarily need another motivational speech.

Sometimes they need to feel seen.

Heard.

Understood.

And when people feel understood, something shifts.

They're more willing to understand.

To engage.

To take ownership.

To contribute.

Not because you figured out how to motivate them.

Because you took the time to know them.

Maybe inspiration isn't something you give people.

Maybe it's something that happens when people feel genuinely connected to the person, the purpose, and the work.

Worth thinking about.

08/12/2026

**The Leadership Gap: When your definition of success no longer fits.**

Three executives have come to me recently with essentially the same goal:

*Help me figure out how to leave.*

Different organizations. Different circumstances. Different careers.

But all three had reached a point where something wasn’t working anymore.

At first, leaving seemed like the answer.

But once we slowed down and started exploring what was actually underneath the dissatisfaction, something interesting happened.

In each case, it became apparent that leaving wasn’t necessarily what they wanted or needed to do.

They needed to recalibrate.

The definition of success they had been operating under no longer quite fit who they were or what mattered to them now.

And this can happen to any of us, at any point, in any role.

Our priorities shift with the seasons of our lives.

What motivated us five years ago may not motivate us today.

The next title may not feel as exciting.

More responsibility may not feel like the obvious answer.

And what once looked like ambition can start to feel like obligation.

Sometimes we mistake that feeling for a sign that we need a new job.

Sometimes we do.

But sometimes the more important question is:

**What if the problem isn’t the job? What if your definition of success is outdated?**

The definition that got you here was built at a different point in your life and career.

It made sense then.

It may not make sense now.

So before making a major career decision, get curious.

What does success actually mean to you today?

What do you want more of?

What are you no longer willing to trade for achievement?

What matters now that didn’t matter five or ten years ago?

And what would it look like to approach your current role through that new definition?

Sometimes that clarity changes your relationship with the work you’re already doing.

And sometimes it confirms that it’s time to move on.

Either way, you’re making the decision from clarity rather than frustration.

Because growth doesn’t always mean finding the next thing.

Sometimes it means redefining what meaningful, fulfilling and successful look like at the level you’re at now.

08/05/2026

Leadership Gap #5: The Evidence Gap

One of the biggest mistakes I see leaders make isn't choosing the wrong leadership approach.

It's abandoning the right one too soon.

I recently worked with a senior executive who had relocated internationally into a new organization, a new culture and a very different way of working.

As the pressure mounted, she began questioning everything.

Instead of leading the way she always had, she felt she needed to become a completely different leader to succeed.

It's a trap many of us fall into.

When we're uncomfortable, our minds become incredibly good at creating stories:

"Maybe I'm not being direct enough."

"Maybe I need to be more involved."

"Maybe I need to push harder."

"Maybe this leadership style just doesn't work here."

The challenge is that leadership isn't an experiment you can evaluate after one conversation or one week.

Trust takes time.

Ownership takes time.

Confidence takes time.

People need consistency before they believe your leadership is genuine.

Together, we worked on something that sounds simple, but is often incredibly difficult: staying aligned with the leader she had already worked so hard to become.

Rather than abandoning her values, she committed to leading with them consistently.

Slowly, things began to shift.

Her team took greater ownership.

People became more accountable for their work and their development.

She stopped feeling like she needed to hold everyone's hand, freeing herself from the burnout that had been quietly building.

Most importantly, she finally had the space to focus on the strategic leadership her organization needed from her.

Here's what struck me most.

Nothing changed overnight.

What changed was that she stayed with the right behaviours long enough to gather the evidence that they were working.

That's the Leadership Gap.

Too many leaders change direction before they've given the right approach enough time to produce results.

They flip-flop between leadership styles, priorities and expectations.

The result?

Teams become confused.

Trust weakens.

Relationships become inconsistent.

And leaders mistakenly conclude that the approach didn't work.

Often, it wasn't the approach.

It was the lack of consistency.

Leadership isn't about chasing the next technique.

It's about having the patience and discipline to stay aligned with your values long enough for your people to experience consistency—and for you to experience the results.

Sometimes the greatest value of coaching isn't introducing a new way to lead.

It's helping leaders stay the course long enough to discover they were on the right path all along.

Where have you seen The Evidence Gap show up—in yourself or in leaders you've worked with?

07/30/2026

Bridging the Leadership Gap #4: When Being Involved Feels Like Leadership

One of the hardest transitions leaders face is recognizing that the work that made them successful is not always the work that will make them successful at the next level.

This week, I was coaching a leader who felt strongly that they needed to be involved in almost everything their team was working on.

Not because they didn't trust their people.

Not because their team wasn't capable.

But because they believed being close to every conversation was the best way to stay informed.

Their concern was valid:

"If I'm not in those meetings, how will I know what's happening when senior leaders ask questions?"

It sounds responsible.

And yet, it uncovered a leadership gap I see often.

We can confuse being involved with being effective.

Many leaders unintentionally create a false sense of control by staying connected to every detail, every decision, and every conversation.

The challenge is that the more time we spend inside work our teams are capable of owning, the less time we have available for the work only leaders can do.

Creating vision.

Thinking strategically.

Building relationships.

Developing people.

Removing obstacles.

Preparing the organization for what is ahead.

And this is often where leaders find themselves stuck.

They want more time to lead, but they are still holding onto responsibilities that no longer belong at their level.

The question I often ask is:

What are you holding onto that is preventing you from leading at the level your role now requires?

This isn't simply a delegation issue.

It's an identity shift.

Many leaders are promoted because they are exceptional at getting things done.

They solve problems.

They have expertise.

They are dependable.

Those qualities matter.

But leadership requires a new definition of value.

It moves from:

"How much can I accomplish?"

to:

"How much can I enable others to accomplish?"

The strongest leaders don't become the centre of every decision.

They create clarity instead of dependency.

They build trust instead of requiring constant visibility.

They create systems that keep them informed without requiring them to be everywhere.

As technology continues to make information more accessible than ever, leadership value will not come from personally knowing every detail.

It will come from creating environments where people can think, decide, and lead with confidence.

Because leadership doesn't scale when everything depends on you.

It scales when your people are empowered because of you.

A question worth reflecting on:

What is one thing you could step back from this week that would create space for you to lead more intentionally?

07/23/2026

This morning I headed out on my road bike with something I rarely have. Time.

No meetings to rush back for.
No schedule to beat.
Just the freedom to ride.

So I chose a route I hadn't ridden in a while.

Halfway through, I discovered much of it had been torn up by construction.

Loose gravel.
Heavy equipment.
Roads that simply weren't meant for a road bike.

I had a choice.

Turn around and retrace every kilometre.

Or let go of the route I'd planned and find another way home.

I chose the second.

It wasn't the ride I'd envisioned.

I spent more time on rough roads than I expected. My speed dropped. My average power wasn't where it normally is.

At first, I found myself frustrated.

Then I caught myself.

I was still measuring success against the ride I'd planned instead of the ride I was actually having.

So I reset.

Instead of chasing speed, I focused on distance, enjoying the ride, and getting home safely with my bike intact.

The ride didn't become worse.

It simply required a different definition of success.

It reminded me of conversations I have with senior leaders every week.

A leader hires me because they're convinced they need to leave their organization.

Through coaching, they discover they don't actually need a new job.

They need a new perspective.

Another leader becomes deeply committed to a strategy, a sales target, or a plan that made perfect sense six months ago. The market changes. The team changes. New information emerges.

Yet they keep pushing in the same direction.

Not because it's still the best path.

Because they've become attached to the original plan.

There's an important distinction.

This is a leadership gap I see more often than people realize.

Commitment is a leadership strength.

Attachment can become a leadership blind spot.

Many high performers have built successful careers by following through on what they say they'll do. Perseverance matters.

But somewhere along the way, some begin to believe that changing course means they've failed.

It doesn't.

The strongest leaders I've coached know that changing direction isn't the opposite of commitment.

Sometimes it's the highest expression of it.

They gather new information.

They challenge their own assumptions.

They adapt without losing sight of the outcome they're trying to achieve.

Sometimes your values evolve.

Sometimes your business evolves.

Sometimes you simply learn something you couldn't have known when you first set the goal.

Changing your approach isn't giving up.

It's making a better decision with better information.

One of the biggest leadership gaps I see isn't a lack of commitment.

It's being so attached to the original path that you stop seeing better ones.

Are you still committed to the outcome, or have you become attached to the path you originally chose to get there?

Leadership Gap #3 -Confusing commitment with attachment.

Great leadership isn't about sticking to the original plan, it's knowing when the plan should change.

07/14/2026

The Relationship Gap Leaders Don't Realize: You don't have the relationship you think you have.

"Tell me about the relationships you have with your team." A question that almost inevitably comes up when coaching people leaders.

Almost every leader answers the same way.

"They're good."

And most of the time, they're right.

They get along well. There isn't much conflict. They enjoy working together.

But over the past few months, I've noticed something interesting.

As we continue coaching and start peeling back the layers, many of those same leaders realize their relationships aren't as strong as they first believed.

Recently, I was working with a senior executive who was struggling to move an important cross-functional project forward. On the surface, the challenge appeared to be about communication, priorities and competing demands.

Then I asked a different question.

"Tell me about your relationship with the executive you're relying on."

The answer came quickly.

"It's good."

So we explored it.

How often do you talk outside of the immediate task?

What motivates them?

What pressures are they carrying right now?

When you disagree, do you have the kind of relationship where both of you can challenge each other openly?

What does success look like from their perspective?

As we worked through those questions, something shifted.

The challenge wasn't the project.

It was the relationship.

More accurately, it was the assumption that the relationship was stronger than it actually was.

I see this often.

As leaders, we tend to define relationships by how they feel.

We get along.

We respect one another.

We enjoy working together.

But leadership asks more of us than simply being liked.

Strong leadership relationships are built on trust, curiosity and understanding. They're built by knowing what matters to the other person, creating enough psychological safety to have difficult conversations, and caring enough to understand their perspective before asking for their commitment.

Those things don't happen by accident.

They're built intentionally.

This is why I believe the future of leadership belongs to those who intentionally develop the human skills technology cannot replace.

Relationships aren't a soft skill.

They're a leadership skill.

Because when relationships deepen, everything else becomes easier.

Conversations become more honest.

Feedback becomes easier to receive.

Collaboration becomes less transactional.

Trust grows.

Performance follows.

One of the greatest gifts coaching gives leaders is awareness.

Not because it teaches them something entirely new.

Because it helps them recognize the assumptions they didn't know they were making.

Here's one question worth reflecting on:

Are your relationships built on familiarity...or are they run deep enough to carry the weight of honest conversations, meaningful collaboration and real accountability?

07/07/2026

The Leadership Skill Most Leaders Don't Realize They're Missing

I recently coached a senior executive who was frustrated with his team.

Month after month, he struggled to get the information he needed from his direct reports to complete his own reporting. The same deadlines were missed, and the same frustration resurfaced.

His conclusion?

"My team just isn't following through."

I asked him to walk me through exactly what he was saying to his team.

He reminded them the reports would be helpful. He mentioned he'd need the information soon. He thanked them in advance for their support.

Then he looked at me and asked, "So why isn't anything changing?"

I smiled.

"You haven't actually asked for what you want."

From his perspective, he had been clear.

From his team's perspective, the request was polite, flexible and, most importantly, negotiable.

They didn't understand how to prioritize it, why it mattered, or how their contribution affected the bigger picture.

This is a pattern I'm seeing more and more.

Not with struggling leaders.

With good leaders.

The ones who genuinely care about their people.

Many soften their message because they don't want to sound controlling, demanding or like they're micromanaging.

So they imply instead of asking.

They suggest instead of expecting.

They hope instead of clarifying.

Then they're disappointed when people don't deliver what they never clearly requested.

Here's the shift:

Direct communication isn't about control. It's about clarity.

Clarity isn't harsh.

It isn't arrogance.

It isn't a lack of empathy.

It's one of the greatest gifts a leader can give.

When expectations are vague, people fill in the gaps with assumptions.

When expectations are clear, people can focus on delivering.

Instead of:

"It would be great if we could move this along."

Try:

"I need this by Thursday at 3:00 p.m. because it's required for Friday's executive report. If something will prevent that, let me know today."

Same respect.

Far greater clarity.

I've learned that many leaders confuse being nice with being clear.

But ambiguity doesn't protect relationships.

It creates frustration, disappointment and unnecessary tension—for everyone involved.

Leadership isn't measured by how carefully you avoid uncomfortable conversations.

It's measured by how effectively you help people succeed.

Where in your leadership might you be assuming you're being clear when you're actually being indirect?

06/23/2026

One leader changed the trajectory of my career.

Not because she taught me everything.

Because she believed in me before I believed in myself.

On my first day after university, I expected a conversation about performance.

Instead, my leader spent time helping me understand how we would work together, what decisions I could make, when to ask for help, and how she would support me.

Years later, I asked why she hired me when I had so little experience.

Her answer stayed with me:

"You had the skills that mattered. The experience would come."

She trusted me to figure it out.

And because she believed in me, I became deeply committed to becoming the best version of myself I could be.

I've also experienced the opposite.

Leaders who made me feel like I needed to prove my worth before I deserved support.

The difference was profound.

One built confidence.

The other created doubt.

Looking back, the greatest leaders in my life didn't tell me who to become.

They helped me discover it for myself.

That's a lesson that has shaped every leadership role I've held and every coaching conversation I've had since.

People don't become their best because we control them.

They become their best when we help them see what they're capable of.

Have you ever had a leader who believed in you before you believed in yourself?

06/16/2026

The leaders who need development the most are often the ones least likely to ask for it.

Not because they don't care.

Because they're carrying too much.

I worked with a leader who genuinely wanted to grow, develop his team, and create better results.

But every time we scheduled a coaching session, something else took priority.

A deadline.

A fire to put out.

A problem that needed his attention.

When we finally got enough consistency to step back and look at what was happening, the real issue became clear:

He wasn't struggling because he lacked capability.

He was struggling because he believed leadership meant carrying everything himself.

The decisions.

The problems.

The pressure.

The responsibility.

And if we're honest, many leaders have been rewarded for exactly that behavior throughout their careers.

Be the expert.

Have the answers.

Step in when things go wrong.

Own the outcome.

Until one day they find themselves leading a team and discover that what made them successful is now limiting everyone around them.

Including themselves.

The fear usually sounds like this:

"If I let go, standards will drop."

"If I'm not involved, things will get missed."

"If I don't know everything, I'll lose credibility."

So they work harder.

Get more involved.

Take on more responsibility.

And unintentionally create bottlenecks, dependency, and disengagement.

Not because they don't trust their people.

Because they don't yet trust a different way of leading.

The breakthrough came when he realized he didn't need to know everything.

He needed a system that kept him informed without keeping him involved in every detail.

Everything changed.

The team stepped up.

Ownership increased.

Engagement improved.

Performance grew.

And for the first time in a long time, he could focus on leading instead of constantly reacting.

This is one of the most important leadership shifts organizations need to make right now.

The future will not be won by leaders who can carry the most.

It will be won by leaders who can create the most capability around them.

Because leadership isn't measured by how much you can do yourself.

It's measured by what your team can accomplish because of you.

A Jacked Experience

08/25/2026

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