How to manage leaders (without looking dumb):

“What the f*ck do you know?”

Two of my executives were going at it. Again.

Tension was think. Everyone awkward as hell. I needed to step in.

But I didn’t.

They were experienced executives after all. I was a 30-year-old first-time-founder. What did I know?

Bad decision. The rift left a scar across the leadership team that took months to heal.

And it was the first time I realized: If your leadership team’s a mess, so is your company.

I needed to do better. Much better.

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“You’re in this role for a reason”

I used to be intimidated by my own executives. Their experience dwarfed mine – at least that’s the image I created in my head.

They were VERY experienced. Top execs from Okta, Atlassian, Redfin, Glassdoor and more. I practically needed a translator for 1 on 1s with my CTO.

My leadership team before.

How was I supposed to lead a group of all-stars like this? Never mind coaching them and managing their performance.

Then one of my closest advisors said something that stuck with me forever:

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

“Each exec is talented, but they’re not a team yet. That’s your job.”

This changed everything.

I stopped thinking: how do I compare?
And started thinking: how can I help?

I needed to transform this group of talented individuals into an A+ team.

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How to manage any leadership team

Managing executives is hard. No way around it.

But the answer isn’t: “hire great executives and get out of their way”. Do that and they’ll take the company in their own direction. Not from spite, but from lack of direction.

“A manager’s output is the output of the organizational units under his or her supervision.”

– Andy Grove, former CEO of Intel

You must step up as the leader. Get command of your team. Don’t let impostor syndrome win.

Here’s how in seven steps:

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I. Limit the # of team members

• Large leadership teams aren’t effective
• Keep yours to 5-to-10 people max
• Include the #1 person in each function
• Avoid exceptions, it’s a slippery slope
• Don’t worry about “hurting people’s feelings”

II. Provide clarity & context

• Make sure every person on the team understands:
• Why are we here? (your purpose)
• Where are we going? (your direction)
• How are we doing? (your progress)
• Only then can they perform at their highest level.

Highland Northstar Framework

III. Set a team rhythm

• Establish a recurring leadership team meeting.
• Weekly or every-other-week is usually best.
• Be reliable. Same day and same time.
• Don’t move things around and cancel all the time.
• Your team will lose faith in you and the process.

IV. Nail your leadership team meeting

• So many leaders waste this precious time with the team!
• Avoid long status updates from each person.
• Push people to problem solve & get goals back on track.
• CEO ensures the most pressing issues are discussed.
• This meeting is your #1 tool for keeping the team aligned.

V. Create p2p accountability

• Peer-to-peer accountability is stronger than top-down
• Great leaders don’t want to let their team down
• Create situations where the group reviews each other
• Set standards together, review goals, review work
• Everyone holds the line together, not just you

VI. Create formal checkpoints

• Checkpoints ensure leaders stay on track through year
• Your leadership team meeting sets the foundation…
• But most CEOs do some combo of the following:
• 1 on 1 meetings for coaching & calibration
• Quarterly Business Reviews (QBRs) for deep reviews

VII. Maximize the value of offsites

• Offsites are a secret weapon for building trust & alignment.
• The connection can last months, or years!
• Physical is always better than virtual.
• Do at least two per year. 2 days long per offsite.
• Yes, you do have time for this. It’s beyond worth it.

As a free bonus to this newsletter, I wrote an article about how to run the perfect leadership team meeting. I hope its helpful to you and your team. Feel free to reply to this email with any questions! 💪

Scot