Leading your people

Leadership

Leadership isn’t just a role you inherit or a title printed on a business card. It’s a living, breathing responsibility.

Something you choose to embody every day in how you show up, set expectations, and carry yourself when things are smooth and when they’re messy. Today we’re talking about our leadership style, lessons we’ve learned, and how you can apply it to yourself.

Agenda:

⏳ Estimated Read Time: 8 minutes

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Leadership principals

Clarity is a gift.

If I had to break it down, leadership is a ladder. And the first rung is always the same: setting clear expectations.

Whether you’re running a startup, leading a team, or coaching your kids’ soccer practice, people can’t hit a target they can’t see.

That’s why the first job of any leader is defining what success looks like and what’s required to get there.

Without this, teams spin their wheels, and frustration builds. With it, people know exactly where they stand and what’s expected. That makes every other step in leadership easier.

Once expectations are clear, people start looking to you to see if you actually live them. Your energy, your enthusiasm, your work ethic; you set the tone.

If you’re showing up late, disengaged, or underperforming, your credibility erodes.

But when you’re visibly committed and delivering results, it’s contagious. People follow leaders who perform and who have skin in the game, whether that’s financial, reputational, or both.

One of the biggest lessons I’ve learned is that leadership isn’t one-size-fits-all.

The best leaders adapt their style to the moment.

In stable, prosperous times, collaborative leadership often works well. You bring people into the conversation, encourage ideas, and build consensus. But in times of crisis or uncertainty, collaboration can stall progress and create unease. That’s when top-down leadership can be more effective. In difficult moments, people often respond better to clarity, decisiveness, and direction.

Great leaders can switch between the two. They know when to invite more voices in, and when to step up and make the call.

I’ve always believe that leadership is most powerful when it happens one-on-one. Public praise is great, but hard feedback should be private.

I often use the simple sandwich method, start with something the person is doing well, address the issue directly, then finish with support and a plan forward.

It’s not about softening the truth; it’s about delivering it in a way that keeps the relationship intact while still driving accountability.

A good leader is never “too busy” to listen. Accessibility isn’t just a reality, it’s a perception. If your team thinks you’re unavailable, they’ll stop bringing you ideas, concerns, or problems until it’s too late.

When people know they can get your ear, even for a few minutes, it builds trust. And trust fuels buy-in.

Early in my career, I didn’t fully understand how to motivate someone who didn’t have equity in the company. I let underperformance drag on for too long because I liked the person and avoided the hard conversations.

Acting sooner is better for both sides. If someone isn’t thriving in their role, you’re not doing them a favour by keeping them there.

Ending things quickly can open the door for them to find work they’re better suited for, and it frees you to find someone who’s the right fit.

Three fundamentals for any leader:

Leadership isn’t static. It’s a mix of performance, adaptability, trust, and accountability.It’s earned every single day.

If you’re not leading the way you want your team to act, the buy-in will wear out. When you model the behaviour, effort, and commitment you want to see, you won’t have to push people nearly as hard. They’ll already be following your example.

Updates and Opportunities

We launched our new Instagram, building off the great community of Kitsch Wines. If you haven’t followed you should, we’re slowly releasing some great speaking videos you’re going to want to check out.

Founder’s Hike – Weekly

📆 Every Tuesday | 6:25 am – 7:25 am PDT
📍 Knox Mountain, Kelowna, BC – 580 Knox Mountain Dr, V1Y 7M7

I’ve been attending Tuesday hikes up Knox with Dan Martell and the crew. They’ve been one of the best parts of my summer. There’s something special about kicking off the morning with that climb — the lake waking up below, the sun spilling over the hills, and founders swapping stories between breaths. It’s been a mix of fresh air, great people, and conversations that stick with you long after the hike ends. Open invite. Bring water, good shoes, and a curious mind.

If you’re in the area get up and go!

At Gather Round, we wrapped up with something simple but powerful: a smoothie blended in the Magic Bullet. It was a reminder that fueling your body doesn’t have to be complicated—just intentional.

Here’s the recipe and its also how I have started almost every day for the last 3 years:

A few minutes, a handful of ingredients, and you’ve got a blend that covers energy, recovery, and growth. Exactly the kind of fuel we needed after good conversations and a hike up Knox.