Thread by @ryan_caldbeck

1/Something I have struggled with for years as a CEO.
I pride myself in being responsive. This means responding to emails and doing it in a timely manner. It signals I value the emailer. It helps unlock things for others.

2/ I also value in-person meetings and think a lot can be communicated face-to-face that is lost over email. Being at a meeting signals it is a good use of my time. As CEO, people notice when I’m there and engaged.

3/ I feel frustrated and stuck when I have to say no to something. Yet it is also my job to say no- a lot. I have to say no to conversations, people, opportunities that look really important but just don’t fit the schedule or someone else should lead.

4/ If I turn down the meeting, I miss the opportunity to celebrate progress, give input, or signal value. Perhaps I also miss the chance to provide input.

5/ If I skip an email, the emailer doesn't get unlocked and might feel hurt or insulted.

6/ Solution: have meetings during the day and email at night. Wait... that can't be the answer. How about balance, family, exercise, boundaries? And think of what signal that sends to the rest of the team about hour expectations if I’m doing all the emailing at night?

7/ So delegate more, right? But there are things that a CEO is uniquely positioned to do and times I'm expected to be in two places at once. The CPO hire and the huge investor want to meet at same time as a long-time teammate is transitioning out? Hard to delegate one of those.

8/ Something has got to give. I don't have a perfect answer but I do know that there are some non-negotiables. Anyway - it is a fairly tricky part of the job even with an amazing team.

9/ Setting clear goals (whether through OKRs or another format) & priorities helps, having a great team helps, saying no upfront but with empathy helps. But the difficult tradeoffs still happen all the time and it is a struggle.