What It's Like to Report to CEO and Founders

Reading Time: 5 minutes | April 12, 2020

I’ve reported to 3 CEOs over the course of 2 years. All three are Founders. All three are male.

I’m proud to have worked with intelligent men. I’ve learned a lot from them over the course of my early career. I’d like to share some of the learnings with you.

Learnings on Meetings

  1. If there are talks around booking a follow up meeting, do it. Don’t expect a calendar invite coming from them. Be proactive and send them a calendar invite with crucial information such as meeting location, agenda topics and details, and any additional resources they should read to prepare for the meeting.

  2. Take notes. Whether on paper or in a shared document, take notes. Sometimes, the conversation will go into a monologue of their vision for the company and high level strategy that could be useful for how you prioritize your team/work. Jot it all down somewhere because the average brain forgets over time, no matter how good you think you are at remembering.

  3. You’ll want 1:1 meetings like every regular employee. You should always have topics to discuss though expect that some (or many) of them won’t be discussed in the time you have. Prioritize them.

  4. Know that your 1:1s won’t always be about your career goals. In fact, it shouldn’t. It’s not all about you. It’s about how can we do better, together.

  5. They often don’t have a lunch hour because it may be booked up by countless other people. I’ve had meetings where I’d book a lunch meeting and indicate on the invite that this is an eat-and-chat meeting. I’d also allot time for us to both go somewhere to get food. This gives them time to catch up on food while we meet. They’re human and need to eat too!

Learnings on Time Management

  1. What’s the bottom-line? What do you want to say? The more succinct you are, the better conversations will go. Cut out the fluff because they can catch bullshit before you even walked in the door. Just get to the point.

  2. They may not always have an executive / administrative assistant. If they do, they may still want to organize their own calendar or sort their own emails. If that’s the case, think of ways to help them get organized by making as many things extremely simple as possible. e.g. appropriately named files or emails with appropriate titles.

  3. They like organized team members because they’re counting on you to advise them. Meanwhile, they’re trying to juggle a million and one items. They don’t have time to help YOU organize your life. Get your shit together.

  4. Sometimes, there will be spontaneous chats and chats may diverge to topics that are philosophical. In other words, it’s beyond the scope of focus for the time being. Absorb the big picture so you can discuss it later though gently steer them back to current priorities.

Learnings on Decision Making

  1. They undergo massive context change throughout the day. This prevents them from attending to minuscule details you are waiting on. When you start a topic, start with a brief reminder of what was spoken about last time. Or, explain the context again.

  2. A CEO is a jack of all trades, they have all sorts of departments reporting into them. Put yourself in their shoes for a moment. They might make decisions others don’t like. We have to remember that they have discussions which we aren’t privy to which gives them a lot more context to make decisions. Trust them to do their job just like they trust you to do yours.

  3. Prioritize what you need from them, and then send a reminder. Give them enough information and a possible recommendation so they can ask more questions and eventually make a decision. You don’t have to solve everything. Getting it started is the idea.

  4. They don’t always know what they are doing either. It’s true. Often times, they’re experiencing things for the first time too, even though they may have worked on their product/craft for the last decade.

  5. If there is a potential major problem, escalate early. The last thing they want to know is that something has been on fire for the last 2 weeks and no one has updated them on it.

  6. They’ll come with problems already solved. They’ll give you the ‘answers’ to some problems because they think it’s the right way to go based on their ‘experience’. It’s good to probe and understand if their way is truly the right way to go. Sometimes, it’s not.

  7. When the financials look grim, it can be rough news to hear you are laid off. Though, having watched Founders grapple with good news and bad news, I can tell you that making the decision to lay off someone is not easy.

Learnings on Feedback

  1. Often times, employees are afraid to give CEOs or Founders feedback because their livelihoods depend on it. On the contrary, employees should give more feedback. You were hired to have a voice. When you do give feedback, make sure it is truly feedback and not gossip nor complaint.

  2. They are likely exhausted by the end of the day. Check in on them and ask something along the lines of ‘how are you doing, really?‘ Be genuine, sincere, and curious. It’s okay to remind them to take a breather and thank them for their efforts in running our company. Maybe, share a small win you saw/heard from the team today.

  3. Occasionally, they might say things that will “hurt your feelings”. There is not much time for a compliment sandwich. This is where you need to learn to build layers of thick skin. At the beginning, you might go home and cry about it. Over time, you’ll laugh at it. How do I know? Oh, I’ve been there.

Learnings on Product

  1. Their product (aka company) is their baby. Yes, they will be (very) protective of it.

  2. You wouldn’t want someone calling your baby ugly. So, don’t call their baby ugly. Appreciate the work others have done to get the product to where it is now. It likely has an epic story, and you weren’t always there for it.

  3. Sometimes, they already have a ‘roadmap of features’ laid out in their head. We need to extract that from their head. While we were hired to make things happen, though that doesn’t mean one should action on everything the CEO says, blindly. Remember to think critically!!!

These men have taught me plenty. They are very capable, brilliant, and experienced. Perhaps one day, I’ll have an opportunity to work for a female CEO or lead a team where I am the female CEO.