CEO cliff notes

My successor at Shogun asked me to include advice for a first time CEO in my transition docs. Here’s what helped me keep my head on straight in a role that could at times feel disorienting:

On Leadership

Be transparent, genuine, and vulnerable with people. Go off script. Most people at startups find “executive presence” to be performative and disingenuous.
Quantify (ie. define with a number) what success looks like for everyone. For any goal or initiative; make it very clear who is accountable, and when things are due.
Keep initiatives on a 2 week cycle and goals on a 1 month cycle. Minimize meetings, and use the saved time to get hands on with the most imperative work.
Team input is necessary, but there are always good reasons to do a thing or not do a thing. Startups are not democracies; at the end of the day the CEO makes a call and everyone gets onboard with that.
When you see organizational politics start forming; make it clear there’s no place for it. Terminate people who don’t understand this.
Track and promptly recognize top talent that go above and beyond. Promotions and raises should come slightly before they realize they deserve it. Otherwise it feels “owed”, and no longer creates a magic moment.

On Strategy

Stay so close to the customer and the product that your IC skillset doesn’t get rust on it. This way, you’ll actually know what’s going on. If nothing else, do this.
Job of the CEO is balancing (1) optimization of current business/revenue lines with (2) investment in an uncertain future to combat obsolescence. This is hard.
Strategy tends to boil down to a mix of product investments and GTM strategies that seem like sure bets and others that seem like wild cards. The ratio of the two will probably vacillate wildly based on how well or poorly business performance is.
If you’re not actively growing revenue month over month- you probably shouldn’t be burning. Profitability gives optionality.

On People Management

For weekly 1:1s: have a system of record, create agendas (using a template as a base), take notes, and most importantly: expect the same of all your reports.
Normalize feedback. Give it and ask for it in every 1:1. Listen, and change your behavior if it’s not serving you or the team well.
If you think there’s an issue with someone; there probably is! Give feedback early and often. Use the Situation Behavior Impact (SBI) framework. Put it in writing.
Escalate promptly with underperformers: informal verbal warning, informal written warning,, formal verbal and written follow up, PIP, terminate.
Document everything. Expect everyone else with direct reports to do the same.

On Investor Relations

With all respect to investors: spend the least amount of time here.
Templatize the BOD meeting and deck and don’t overthink it. The focus will always be on growth and addressed in organic discussion or during the closed session.
If you have major news or a big decision: hold 1:1 meetings with the board members before the meeting. Send the deck in advance. Board meetings should be boring. No surprises.
Send a monthly investor update to all investors. It’s good hygiene, and transparency wards off issues. Use a template, and don’t overthink it; you’ll be lucky to get 1 reply.
Keep in mind that it’s easy to be a critic, and it’s hard to be in the CEO seat. Good board members and investors remember that.

Ultimately, everyone has their own leadership philosophy. I found that consistency counts for a lot. Whatever your methodology is; systematize it and stick to it. If you find that you’re struggling in the role; remember that leadership is hard, and it’s only made easier by revenue growth.