How do you CEO? / Benjamin Humphrey @ Dovetail
A learning journey of how startup CEOs work.
Over the past 6 six months, I've interviewed 10 CEOs to learn how to do my job better.
It was one of the best things I’ve ever done for my own professional development and I hated the idea of keeping all the insights to myself. They all kindly agreed to share our candid conversations so that we can all learn from each other.
I’ll be posting the conversations every Monday and a summary of my own insights at the end of the series.
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#1 Benjamin Humphrey / CEO @ Dovetail
How do you CEO?
My style is to try and delegate accountability downwards to take pressure off and get myself out of a job. As much as you can, you want to distribute responsibility to your team.
I’m a big fan of building trust with my team.
One of the ways is getting to know my direct reports on a personal level. A lot of CEOs want to retain control. I’m the opposite. Ideally, I can just go away and everything is handled.
Day to day the company runs itself. Even our updates like all hands, monthly founder email, and board deck the team writes that. All logistics are handled and the content is written by the leadership and functional teams.
But when the team is stuck making a decision, I have the authority to just make a call. My key levers are firing, deprioritising and defunding and I still do that. Where I add a lot is a sense of urgency.
When I hire senior leaders, I don’t just look for hard skills—another important factor is whether they can manage stress and accountability. Part of that is holding themselves accountable, even in their personal lives - look after themselves, sleep, diet.
Some of our early employees couldn’t control their emotions. They were experts at their craft and had all the context but they weren’t functioning leadership team members.
How do you set strategy?
We communicate our strategy through asynchronous internal blogging, all on Notion, and fortnightly company all-hands meetings.
The most important is the monthly founder updates which are fairly long written updates.
We use that to drive strategy.
Our blog covers all sorts of things—how we hire, how people management should work, firing, how we’re scaling, our hiring challenges, founder vision, and high-level strategic stuff.
We write about what we are doing as founders:
Why did we start the company?
What’s the point?
What are the ambition levels?
Where are we in our lives?
What new things do we want to do in life?
How we want to create real value for people
What can we do locally - these things keep us at Dovetail
We are very open in our written comms and all-hands updates. The beauty of it is that you can refine written communication well. It’s also an asset that people can go back to.
We run the big pieces past the leadership team first.
We use both verbal and written communication—after each all-hands we publish a blog with more detail.
How do you set goals?
We’re terrible at goal setting and hitting quantitative goals. We used to have a company-wide goal framework which had 3 focus areas for the year. They were simply:
Build the best team
Make go to market amazing
We then picked projects to ladder up to one or more of those.
This worked pretty well.
We tried OKRs but they are dog shit.
We found people spent more time on wording the right OKR than the actual project to do it—it created work about the work. The numbers people set were usually pretty arbitrary as well. Like ‘ship three features’.
Now we have company focus areas.
We make them jazzy and memorable.
It is more about setting the right incentives and encouraging the right behaviour rather than the numbers. Focus areas successfully communicate what we’re focused on strategically. Each team sets their own performance goals. Accurate quantitative product goals are really hard. Operations is much easier as it is more naturally quantitative, e.g. budgets. Marketing & Sales you can measure and track and functional leaders drive accountability to a number, so that’s easier.
Overall, I try not to worry about specific goals. It is about themes and focus areas. Drive towards those things. If you make all the right plays on the field, the score takes care of itself. So focus on making the right plays.
How do you manage sensitive communication?
Tackle it head-on. We had to let someone go after the retreat for bad behaviour. They hadn’t even started yet, so had to leave before they had their official first day. Our leadership team posted a really good post on the internal blog about it. When a person is leaving you have to control the narrative rather than them.
We had a period where a lot of people weren’t passing the probation period. People were thinking “if this person got fired during the probation period, am I gonna get fired too?” We addressed that in a blog post, by simply saying if you are off track, you will know.