UPDATE: The FREE accompanying 30-60-90 day roadmap is now available for download on Notion! Go here to download it. Happy Checklisting!
Projects Galore, and Avoiding Overwhelm
The more successful your Exec and startup are, the more they're going to be pinged. Everyone is going to want something from them, and that means everyone wants something from you as the Chief of Staff. And pretty soon, it can be difficult to discern what is actually urgent and important, and what is not. It is your job, therefore, to help your Exec filter the signal from the noise.
These requests tend to fall into these buckets:
- Which pings are urgent and important
- Which pings are untapped opportunities with huge potential
- Which pings are irrelevant / time-wasters
👉 As previously discussed in other writings, a CoS's main responsibility is to become an extension of their Exec. This means learning how to think like them, make decisions like them, and prioritize for them. In terms of the startup, your brain essentially becomes a clone of your Exec's.
When I first started working for Matt, I knew I was in the presence of someone who was smart and ambitious. Like many founders, Matt had (and still has) huge undertakings and goals — and because it's impossible for one human to do it all on their own, he hired a Chief of Staff (hello 👋)
Within a few months of joining Matt, I realized I was getting pulled in a million different directions. There were many priorities that fell on Matt's plate that now fell on mine. My day-to-day as an early CoS meant juggling everything from his Inbox (which had hundreds of unread emails with no response), to becoming the catch-all for all internal questions related to Operations, HR, and People, to scheduling his many coachees in an impossibly full calendar.
And to make matters more complicated, just as I was hitting my groove, Kate Clark put out a wonderful article on Matt's coaching. So...for all my Inbox Zero efforts, Matt's inbox became flooded overnight. 😬
If Matt was busy before, now he was slammed: everyone wanted Matt to coach them, were seeking advice, or had an "interesting + can't miss" project they wanted him to be a part of. (/s intended.)
Simultaneously thrilled for Matt's well-deserved press while throwing myself a mini pity party, I pulled it together. I had to figure out how to help Matt pay attention to the right things (which meant how to make me prioritize the right things.)
Up until then, my main focus was on improving the Mochary Method software and helping Matt guide the company (along with everything else listed above.) And now, just like that, we were focused on freeing up Matt's already-insane schedule. We also had to jump into action quickly and create group coaching sessions to accommodate the even-bigger demand.
And that's all the reactionary, "catch-everything-before-it-falls" stuff. When Matt is on a roll, he's really on a roll ... and so, on top of all this, Matt's ideas continued pouring in on how he was going to turn Mochary Method into a full-fledged, hundred-billion-dollar empire. I felt myself being excited and overwhelmed at the same time.
A good friend of mine, Kaveh Hosseini, once gave me this powerful advice: "Do not react: respond instead."
The key difference between reacting and responding is simple:
Reacting means you're attending to the thing that is loudest. You're not giving it much thought beyond the hysterical voice in your head screaming at you that you're going to die if you don't take care of it right then and there. You go in order of whichever voice shrieks the loudest in your mind.
Responding means you insert a mindful pause in your actions. Pausing isn't doing nothing. You're pausing. That's doing something. But you're creating the space you need in order to calmly figure out whether it's actually an urgent priority, or if your amygdala is just screaming at you.
Once you've given it some thought, you can choose to respond by either:
- Doing it immediately
- Doing it later
- Delegating it to someone else
- Not doing it at all
If you take care of it right away, it's because you gave it some thought and realized it is, in fact, urgent and important.
If you end up placing it on the back burner, it's because after some thought, you realized it's not urgent at all.
If you ask someone else to do it, it's because it's not the best use of your time to do it (or you're not the best person to do it), but there's someone else whose time it will be well worth. You may ask your EA to help with scheduling, for example, instead of you doing it yourself.
If you don't do it, it's because it isn't important. If you know the person who made the ask and rang the bell of urgency, make sure to close the loop with them so you don't leave them hanging and potentially sour the relationship.
💡 Regina's Resource: I recommend using the CoS Roadmap Template to plan your projects and priorities.
💡 Friendly reminder: you don't owe responses to people you don't know. Your time is no longer your own when you're working. Your time is your Exec's time. And that means every second you spend with someone who is wasting your time, you're actually wasting your Exec's time. Think of that when it comes to prioritization.
Your Ultimate Goal
A few months into working with Matt, he said something to me that I'll never forget. And the reason I won't ever forget it is because it was so impactful, I wrote it on a sticky note:
It might depend on your Exec's definition of "Superhuman," but it's pretty clear in my relationship with Matt: I have to enable him to do all the things he cares about.
Every time I prioritize my time, I ask myself: what are the things that Matt wants to achieve? To help me understand what I should be spending my time on, I frequently reference the goals Matt has set for himself. I created my own Goal Tracker for Matt and frequently reference it (see picture.) *(In fact, my dear friend Jeff Bargmann refers to me as the "*Project Manager to Matt Mochary's life - the dream." I like that, actually.)
By defining Matt's goals, I can now figure out what would make him feel like a Superhuman by tracking all my actions back to his goals. As a Chief of Staff, Matt's goals are my goals.
Additionally, because Matt has gone through an Energy Audit, I understand the tasks that absolutely drain him - things like operations, admin tasks, ordering things, and pretty much anything that doesn't involve creating meaningful connection with other human beings.
Knowing this, I can now take those tasks off Matt's plate and either outsource admin tasks to my EA, outsource tasks to other members on the team who are frankly better at them and enjoy them more than Matt, or handle them myself.
So, if you're unsure where to start with priorities, first align yourself with your Exec. What do they care about? What are their goals that will lead towards building a successful company? And finally, how can you enable them to feel absolutely unstoppable? Because that's the guaranteed way to make them feel like a Superhuman.
That's how you can help them prioritize their work. Let me know what you do to help your execs prioritize. :)
The Coach Behind the Coinbase and Robinhood CEOs, by Kate Clark (The Information)
Chief of Staff writeup, by Matt Mochary
Video of Matt describing the Chief of Staff role (6 min), by Matt Mochary
Chief of Staff Roadmap Template, by Regina Gerbeaux
Energy Audit, by Matt Mochary
Thank you to Matt Mochary, Jeff Bargmann, and Lucas Gerbeaux for reading initial copies of this write-up and for contributing your thoughts. I am grateful!
The FREE accompanying 30-60-90 day roadmap is now available for download on Notion! Go here to download it. Happy Checklisting!