In the Shadow of a CEO

Years ago, I was assigned to a CEO’s pet project — one doomed to fail. But while the project struggled, the real value came from simply being in the room.

While the project itself was doomed to failure, what I got out of it was invaluable.

For months, I worked in a university teacher’s office, stationed at a small desk behind my boss — the co-founder of an up-and-coming startup. I could see their screen from my desk and was encouraged to listen in on their meetings — while pretending not to — as I multitasked on my real work. I was learning the business slowly by osmosis. Like I mentioned, the project I was assigned to was a dead-end pet project from the CEO, meant to optimize one aspect of their workflow. It was time-consuming and lacked direction. Being new to the job and the industry — straight out of university — I did what I was told.

Listen and Learn

The key point is I took the opportunity, listened and learned. After some meetings, when there wasn’t a fire to extinguish on our multiple projects, we would debrief together:

• Do you think this is a good project for us?
• How did you perceive the client’s interest?
• How can we deal with this particular feature?

By then, I had broad experience managing student projects — at least on the technical side. Those are the best to learn because if something is to go wrong, it will. When you don’t know enough to ask the right questions, you end up troubleshooting for hours. But once you find a solution, it sticks with you forever. Maybe it’s also because I’m stubborn and I wanted to find solutions myself; that’s possible, too.

One thing that fell far beyond my comfort zone, though, was negotiating budgets and speaking with clients. I used to be scared of taking a phone call, so high-stakes meetings were a lot to take in. Naturally introverted, I preferred emails and instant messages (or finding solutions on my own).

The Art of Taking Notes

One key point in meetings is, of course, retaining information. I used to take meeting notes on my side, and the CEO would do the same. I would be tasked to combine them afterwards, therefore I had clear insight into their thinking — what was important, what wasn’t, and how to structure well-written notes for future reference.

Before you ask — of course, the notes weren’t taken on paper. Unless I had to sketch something, I much preferred being behind a keyboard. We were on Google Docs and eventually switched to Confluence, collaborating in real-time.

My Secret Note-Taking Trick

At this point, I’d like to do a small detour from the main topic and point out a skill that will be useful all of your life if ever you gain it. A skill you can learn on your own that will make your life much easier. Learn to type while not looking at your keyboard as soon as you can.

Type with your hands not your eyes.

The main advantage of typing without looking? You can maintain eye contact with the camera while noting every key piece of information. Let’s face it: meetings are mostly remote, so this skill will come in handy. You don’t need perfect technique, but in my case, I can tell if I make a mistake and correct it while writing without ever looking at the text I’m writing nor the keyboard. Your hands know. I’m sure there are articles out there on how to do it, I didn’t learn any, I just practiced typing slowly while looking, then gradually stopped.

Bonus Secret

You can have a quick template for your meeting notes, with headings such as Milestones, Objectives, Blockers and Others. You should prepare a list of questions. Most of them can be useful across meetings:

• Did your milestones change?
• Are you foreseeing any blockers?
• Busy week, right? (Small talk is sometimes necessary)

Others are specific to the project, things you think you should know but don’t yet.

Back to our story.

Flow of a Discussion

Early on, I knew I couldn’t emulate the CEO’s delivery, but I picked up on their pacing, learned to sense tension, and understood how to diffuse it. Maybe their jokes or vocabulary seemed cringe and/or outdated to me, but they always fit logically into the conversation.

It’s all about the conversation flow.

Free Meeting Trick

If you pay attention, you learn useful tricks, too. Here‘s a free one just for you.

No need to admit ignorance.

So CEOs are busy and can’t always prepare for meetings. Therefore, instead of them admitting they don’t know the milestones of an ongoing project, they might ask their interlocutor to go through their milestone plan to make sure it didn’t change. Brilliant, right? But only if done subtly.

Climbing the Ladder

After weeks of shadowing, I organically started to participate in the meetings, at first silently next to them and slowly answering technical questions. From this, I started to take client meetings alone slowly, never forgetting that if I don’t know something, I can always say something like: let me get back to you on this, I need to verify a few things on my side.

It slowly built my confidence and set me on a track to take more responsibility until I got to be project manager and the main point of contact for most clients, freeing up time for the CEO to build business relationships and develop other parts of the company while operations were in good hands.

Conclusion

The project itself was never the point. It was just tasks running in the background — what truly mattered was what I absorbed from being in the room.

Leadership starts with paying attention.

Not everyone will have the chance to shadow a CEO but always look for the why behind the flow of meetings. Pay attention to what’s said — and what isn’t. Be present, be observant, and learn from every interaction. After all, there are many paths to project management, but they all require your full attention. Watch, listen, and step forward — because leadership starts with paying attention.