Note: while this write-up is geared specifically for Chiefs of Staff, it can be applied to any hire who is onboarding through Matt Mochary's shadowing process. To learn more about the shadowing process from the CEO perspective, please click here.
If you're reading this post, you've probably just landed a job as a Chief of Staff. Congratulations on this achievement!
While it's normal to create a 30-60-90 day plan with your CEO, the first thirty days in particular are especially critical. This is because as you start out, the first thirty days are the most precious time you have to begin the mind-melding process with your CEO and create deep trust between the two of you.
If I had to break it down into several steps, I'd say criteria for success looks something like this:
- Days 1-30: Become an extension of the way your CEO thinks
- Days 31-60: Become an extension of the way your CEO behaves
- Days 61-90: Become an extension of the way your CEO makes decisions
Depending on the company you've joined, your criteria may be slightly different from what I've outlined above, but there shouldn't be too much variation. This is because the Chief of Staff role is one where you are an extension of your CEO.
That means if, for example, the CEO was to suddenly take a leave of absence, you become the directly responsible individual (DRI) in knowing how they think, act, and make decisions.
This might seem like a tall order. Luckily, there's a very easy way to start the mind-melding process. Let's jump right in.
How do I onboard myself?
Start by shadowing your CEO for thirty days.
Matt writes extensively about this process from the CEO's point-of-view here. Below is how I think of the process from the CoS's point-of-view.
During the first thirty days, do the following...
1. Ask any and all questions.
Your CEO should be not only encouraging, but expecting you to ask questions. The more questions you ask, the better context you'll have on how they think. The best questions usually start with "why."
Here's a fun activity: see if you and your CEO can make a bet on whether you can make them get sick of hearing your "why" questions. My guess is you won't get there. In fact, I'd bet that the CEO would become hyper-aware of your desire to get up to speed quickly, and they'll gain more trust in you.
2. Watch how they write.
This one is such low-hanging fruit for incredibly high-leverage learnings. In the beginning, watching your CEO Inbox Zero might seem like a death sentence of boredom for you, especially if you're a GTD, go-go-go kind of person. However, it is crucial you treat this time as study time.
✨ Personal anecdote: When I started working with Matt, I studied the way he wrote his emails and Curriculum write-ups, everything down to the smallest detail. For example, Matt adds double-spaces at the end of each sentence.* He also adds spaces between ellipses. You don't have to be as hyper-vigilent as me, but you'll find this practice is extremely helpful if you end up becoming the DRI for inbox zero-ing them and drafting memos, pitch decks, and more for them in the future.
*Fun fact about the double-space example above: because of this peculiar quirk, when I write now, I find that my writing voice occasionally comes across more as Matt's writing voice than my own just by implementing a double-space.
3. See if you can start predicting the way they'll respond to questions, comments, and concerns.
- The quicker you can pick up how they prioritize things, the more effective you'll be as a Chief of Staff. This one can be tricky, because it's part-IQ and part-EQ.
- On one hand, you'll want to understand the way the CEO thinks about problems involving product. How do they think about OKRs? GTM strategy? Sprints? Feature prioritization?
- Simultaneously, you'll need to know how they think about problems involving people. How do they see the teams and individual department performance today? Which people do they have close relationships with? How do they view company culture? Do they have favorites that have caused them blindspots? Do they have an issue with someone on the team that is causing them to jump to uninformed conclusions about that person?
- As you go through this discovery process, do make note of where you may agree or disagree. Chances are, your CEO has blindspots — everyone does. Your job as a Chief of Staff is to have a visceral understanding of how the CEO thinks, and to be able to have hard conversations with them on what you think they might be missing.
4. Document processes as you learn them.
When you start, your CEO will offload a ton on your plate. Some of these tasks will be permanently yours as the Chief of Staff. But many are tasks that they've been simply handling up until this point because, well, no one else was doing it. Your job past the 30-60-90 day mark will be to hire and train people to do those tasks. And it will save you a world of hurt if you've diligently written things down as you go.
✨ Personal anecdote: When I started as a Chief of Staff, Matt insisted I do all tasks one time to know how to do them, before I outsource it to someone else. I already knew I wanted to hire an assistant to take care of things like phone calls, scheduling appointments, and other administrative tasks. Therefore, I created a database in our Notion wiki of "how-tos" for the future assistant.*
*Helpful tip: I will include a more-detailed writeup on this hopefully in the future, but the two best tools I can recommend to you are Loom (to record yourself doing the tasks once), and Tango (to track all steps as you move your mouse around and click on things and complete the task.) These two tools probably saved me literally hundreds of hours of onboarding and training that I would've otherwise had to do when my assistant joined a month later (which would create even more work on my plate.)
5. Understand what fear, anger, or sadness look like in your CEO.
Let's be very real for a second here: the CEO to CoS relationship is a very personal one. There will likely not be many other people in the CEO's professional career who know their innermost work-thoughts better than you do. (And, if it gets there, you'll likely know their innermost personal-thoughts too, as personal and work life are so intertwined for CEOs.) The only other people who might know the CEO's thoughts just as well are co-founders. But even then, there are some times when CEOs don't feel like they can confide their deepest fears with their co-founders.
However, you as the Chief of Staff are the confidant and sounding board. You will know your CEO's greatest sources of joy, their deepest fears and shame, and the things that piss them off the most.
It's your job to understand what their triggers are.
You must know the telltale signs of when your CEO is triggered.
And — this is the hardest part — you must know how to get the CEO out of their triggered emotion.
✨ Personal anecdote: I got lucky. Matt was already hyper-aware that anger is his triggered emotion. He shared this with me, even during the interview process. And he made it super easy: he gave me the phrase that gets him out of that anger. Now, when I see him shifting towards anger, I have to say, "Matt, I perceive you to be in anger." There have been times I've had to say that phrase to Matt, and as soon as I do, he completely stops talking and just sits there. He may get up and walk away. But he doesn't say a word until he's finally shifted out of that anger.
At some point in your first thirty days, have a raw, honest conversation with your CEO about their primary amygdala-driven emotion. Is it fear, anger, or sadness? And then share with them yours: what is your primary amygdala-driven emotion? What gets both of you out of that state?Note: I highly recommend the Truity Enneagram Test to literally everyone I know. Aside from being an incredibly useful introspection tool, the Enneagram teaches us what our primary emotions are: Body Types (8, 9, and 1) are driven by anger; Head Types (2, 3, and 4) are governed by sadness; and Heart Types (5, 6, and 7) are driven by fear. Take the test and discuss it together.
Conclusion
I hope you find these onboarding tips helpful. When in doubt, I believe that radical candor and vulnerability can dissipate most concerns. Remember that you were hired by your CEO for a reason: they felt a connection to you, saw you are an amazing operator and do-er, and they're ready to begin trusting you.
Big thanks to Matt Mochary for reading through initial drafts of this write-up, and to both Frances Tran (CoS at FreeWorld) and Cullin McGrath (Program Manager at On Deck Scale) for the nudge to write this in the first place.
