As a CEO, is it better to be a bit aloof from the team — or work super closely with them, hands-on?

I think about this quite a bit, and noted the new CEO of Starbucks is building his own office in Newport Beach. Not moving to Seattle to work out of the HQ.

That may well work well. But I’d call it aloof. He won’t be close to the troops on a daily basis.  Starbucks is a pretty big company, but still, interesting.

I also remember in the earlier days of Box, visiting their HQ. And Aaron Levie was literally sitting in the middle of all of engineering.  Right in the middle of a big open group of devs.  That’s as anti-aloof as you get 😉

When I was a first-time founder, I was mostly aloof.   Very hands-on with the customers and my cofounders, but a bit aloof with the rest of the team.  I checked in on everyone every day at the end of the day, so I connected with them. But mostly, on day-to-day work — I stayed a bit apart. I gave people space, and I maintained, frankly, some seeming authority by being a bit aloof. My co-founder was more hands-on and bridged the gap here (bless her).

The second time, I was even more aloof — this time, intentionally. I spend lots of time with my VPs, but almost no time with any individual sales reps, or almost any of the individual engineers. I thanked them, brought them lunch, cheered them at all-hands. But I intentionally stayed a bit distant beyond that.

SaaStr itself is tiny and maybe isn’t a perfect case study. But it was the first time I tried to be less “aloof”. I tried to work closely with everyone on the team, full-time, part-time, junior or senior, external and a leader. I treated everyone as an owner and a leader.

I think my learning is that’s too much :). I think most folks want some distance from the CEO. They start thinking things and seeing things that aren’t there. It borders on too much transparency and honesty. A line you can accidentally cross.

I’ve walked it back now a bit. I’m still there for you, for everyone, past or present. But trying to be a bit more aloof for those that don’t want … that direct interaction.

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