My friend Lara Hogan published an email I had sent to her way back (“Advice for a new executive“) and it turned out to be super-helpful to a lot of people based on the engagement with her tweet about it. In a similar spirit, I’m publishing a previously-private email I sent to a startup CEO who was asking me for tactical guidance on how to dig out from a jammed calendar that he felt was preventing him from thinking strategically and focusing on bigger things. I was asked for similar advice multiple times since then so time to publish. I think this advice is generally useful to managers at all levels. Below is what I wrote, with only minor edits.

First, make sure you are prioritizing your core CEO duties first. I think Fred does a good job of articulating what those are in this post. In short, 1) keeping everyone on the same page with vision and strategy, 2) recruiting, and 3) making sure you have enough money in the bank (fundraising and revenue activities).

Some questions to ask:

1. Are there meetings where you feel like you’re doing someone else’s job that isn’t filled? (example: you’re doing the work of VP of Engineering in addition to your CEO duties) If that’s the case, focus on filling that role. Start with the one that will give you the most leverage and save you the most time. The difficult part is that it is MORE work to fill a role than to “just do it” sometimes but waiting only means your life will suck longer.
2. Are you holding meetings to compensate for the weakness of someone on your team? (example: you attend sales-related meetings that really should be run by VP of Sales but you don’t trust that person to do the meeting the way you want, so you attend). Apply appropriate pressure on your VP of Sales to do the job (and I’m specifically referring to the “feel pressure / apply pressure” concept that Ben Horowitz has written about). If you don’t feel confident in that approach, it’s probably time to put a plan together to replace that person ASAP.
3. Are there meetings you attend that you can delegate fully to someone else? Are there any high-performance people on your team who could take on more responsibility? Make that happen.
4. Are you having any 1-on-1’s that aren’t essential? Everyone will want to spend time with you but make sure any 1-on-1’s are a good use of time for YOU. Kill the ones that aren’t a good use of your time.
5. Are the meetings you have useful with clear agendas and followup items? (Nothing wastes time like useless meetings) This HBR article (“How to Design an Agenda for an Effective Meeting“) is a useful framework to evaluate whatever you are doing now. It outlines an overall approach and includes a sample agenda. Also see Ken Norton’s post “Meetings that don’t suck.”
6. Do you have any recurring meetings that have outlived their usefulness? Kill them.
7. Are there projects/initiatives that are low-value but take up a lot of your time? Consider killing them.
8. Are you leveraging your executive assistant to the fullest? Do you have the right EA? It’s a bit of work but I suggest the “quarterly time analysis” that Matt Blumberg talks about in this post about how he works with his EA. The post overall is useful. Over time, you can teach your EA a rule set to enforce the way you want to spend your time.

Sometimes you’re just in a period where things are going to suck and you’ll be working a lot of hours for some period. You want to minimize the length of those periods but sometimes it’s unavoidable to have a packed schedule. In those cases, the best you can do is try to get a good night’s sleep every night, eat well, and exercise. Good luck!