I was scared of my own executives (until I did this):

I used to be scared of my own executives.

When we passed $10M revenue, I started hiring C-level folks from top tech companies. Atlassian, Okta, Redfin & more.

I was younger than the executives I hired. And I had far less experience, even as their CEO.

What could I teach them about sales, marketing, operations, and technology that they didn’t already know?

How was I supposed to manage their performance?

How could I get them to buy-into our culture, while still pushing it forward?

I was struggling to even lead my team meetings. So I went to one of my closest advisors about it. He said something I still remember today:

“Don’t forget, you’re in this role for a reason”.

“Your execs are a bunch of talented individuals, but they’re not a team. It’s your job to make them one.”

This changed everything.

My job wasn’t to have all the answers.

My job was to get these highly skilled individuals working together like a championship team.

To create cohesion.
To create accountability.
To create mutual respect.

To create the conditions for the team to succeed. Together.

⁂

So how did I actually do turn it around?

Five key things…

1. ALIGNED THEM UNDER A NORTHSTAR:
   Your execs can’t lead their teams the way you want if they don’t have clarity on three things. Why are we here (your purpose). Where are we going (your direction). How are we doing (your progress). That’s your company’s Northstar. Every exec had to align and contribute to it. Zero exceptions. This is a line you must hold as CEO, or your execs will fill in the blanks for themselves. I finally got the balls to do it.

2. CREATED P2P ACCOUNTABILITY:
   Peer-to-peer accountability is far stronger than anything you can do yourself. It finally clicked for me – great leaders don’t want to let down their team. But first, I had to reframe who their team actually was. I’d say on repeat: “The leadership team is your first team.” Not the team you lead individually. It’s these people in the room who represent the company’s leadership. Because I don’t care if one function wins and the rest of the company fails. There are no individual awards at this level. Only team championships.

3. GOT THEM IN SYNCH:
   Execs don’t have time for scheduling bullshit. If you’re wasting their time in meetings and rescheduling things all the time, they’ll instantly lose trust. Execs need reliability, so they can build their own schedule around it. That means creating an operating rhythm at the leadership level that they fully understand and can depend on. What’s your philosophy and cadence for leadership meetings? 1×1s? All-hands? Off-sites? QBRs? What’s the purpose of each, the format, and what’s expected of them? Lay this out and they’ll start to see it as helpful, not hurtful..

4. ALIGNED THEIR INCENTIVES:
   You can call them a first team, but if they’re paid like rivals, they’ll act like rivals. Compensation drives behavior. Don’t fool yourself otherwise. I put my execs on the same bonus plan structure. They got paid 50% for the team hitting its annual goals, and 50% for their function achieving its annual goals. Here’s the the exact bonus plan I used.

5. CREATED OPPORTUNITIES FOR COHESION:
   Cohesion doesn’t happen with meetings alone. They need to be well designed and run. Leadership meetings matter most for collaboration and problem solving. But off-sites may be the most important for building lasting bonds between your executives. I treat my off-sites like event, thinking through every second of the day, from programming to dinner. All of it should reinforce your Northstar and bring the team closer together. Make it an experience they won’t forget.

⁂

This worked for me scaling my own company. But is any of this relevant anymore?

Block CEO and Twitter founder Jack Dorsey wants everyone in the company working for him directly:

“In the most ideal case, you know, there is no layer,” Dorsey said. “Everyone in the company reports to me, and that would be all 6,000 of the company.”

His argument is that AI makes this possible now. So does that mean the executive team is going the way of the dinosaurs?

Not so fast.

I’m going to dissect his new essay on the future of management in the coming weeks.

Till next time,

Never say die 🏴‍☠️

Scot

→ scotchisholm.com
→ highlandacademy.com