Start by shadowing your CEO for thirty days. During the first thirty days, do the following...
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. In fact, your CEO would become hyper-aware of your desire to get up to speed quickly, and they'll gain more trust in you.
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.
The quicker you can pick up how they prioritize things, the more effective you'll be as a COO. 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.
<aside> <img src="/icons/new-alert_purple.svg" alt="/icons/new-alert_purple.svg" width="40px" /> Tip: Make sure you do all tasks one time to know how to do them, before you outsource it to someone else.
Document each tasks as you learn them, that way, in the future when you hire an assistant to take care of things like phone calls, scheduling appointments, and other administrative tasks, you already have a database in your Notion wiki of "how-tos" for them.
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When you start, your CEO will offload a ton on your plate.
Some of these tasks will be permanently yours as the COO. 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.
The two best tools we can recommend to you are:
<aside> <img src="/icons/new-alert_purple.svg" alt="/icons/new-alert_purple.svg" width="40px" /> Tip: Take the Truity Enneagram Test and discuss it together.
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Aside from being an incredibly useful introspection tool, the Enneagram teaches us what our primary emotions are:
Let's be very real for a second here: the CEO to COO’s 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 COO 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.
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?
Hopefully, you’ll find these onboarding tips helpful.
When in doubt, 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.