Do You Know Where You Stand With Your CEO? Here’s How to Tell

Editor’s note: This is an excerpt from Dan Slagen’s new book, Understanding Startup CEOs. Dan is a four-time startup executive specializing in scaling global go-to-market functions from early stage to $100M+ in ARR. With experience in both B2B and B2C at companies such as HubSpot and Wayfair, Dan has built teams across marketing, growth, sales, customer success, business development, and founded and sold a video tech startup of his own.

One of the most common things I hear from friends and colleagues reporting to a startup CEO is that they never really know where they stand from month to month.

Are they doing well? Should they worry about anything? What does their CEO think of them and their team?

Those types of self-perpetuating questions can lead you down a dark path mentally. If you’re not careful, you’ll start fearing every one-on-one meeting your CEO schedules without a description of the purpose. You can spend days and nights wondering what the meeting is about and looking for signs that it’s not about firing you. You’ll start thinking about things a few weeks or months ahead that your CEO wants you to be a part of, and then you figure your job is safe.


But wait. What if something has changed? Why won’t this feeling in your gut go away? Should you start looking for new jobs? If you get fired after just six months with this startup, what will people think?

Leaving your big, comfortable company wasn’t worth the risk. Your former colleagues are probably having a grand time in their roles while you’re trying desperately to tell if your CEO even likes you.

See how dark it can get?

It can happen in a hurry. Borderline paranoia.

The truth is that startups are a lonely number. They’re a mental battle of epic proportions, and you have to get your head together to endure. You can’t spend every day wondering if your last day is around the corner because then it will be. You’ll lose the focus, passion, attitude and drive that the company originally hired you for.

Remember that your CEO was elated to originally hire you to the team, the person full of confidence, empathy and creativity. You might think that you lost your confidence, empathy and any creative ideas.

No. You stopped caring.

You let self-doubt creep in, and you sought daily affirmation that everything would be okay. Your CEO won’t give you that. If you let internal behavior knock you out, you won’t succeed. This doesn’t mean you can’t have impostor syndrome or feel you’re in over your head sometimes. That’s normal.

But you need to focus on moving the business forward, not fretting about your future with the startup. If you consistently put in the work, try to learn new ways, make yourself better and keep driving the company forward, your confidence will increase.

Is trying to gauge how you’re doing hopeless? No, not at all.

Here are a few things you can do to get constructive feedback and read through the lines of communication.

Start by scheduling meetings once a month. If your CEO hates recurring meetings, just send a new invitation on a monthly basis. Center the meetings around getting feedback with the desired outcome of identifying ways for the company and team to move faster and be more efficient. In each meeting ask what your CEO has seen from your organization within the past 30 days and would like to see more of.

You can send the topics you’d like to discuss to your CEO the day before the meeting, depending on whether you want thoughtful reactions or knee-jerk responses. Both types can be telling. Either way, get reactions to three areas, including:

  • Projects: This can be a sprint, campaign or goal that you and your team worked on
  • Behaviors: How efficiently people collaborated and how well they interacted with each other
  • Performance: The output based on how you and your team spent the time

After you hear what your CEO would like to see more of across these three areas, ask about what they would like to see less of and what’s worrisome about specific actions or behaviors.

You can ask the “What keeps you up at night?” question, but that usually won’t get specific feedback for your department. You also should understand what your CEO would like to see more or less of across these areas in other departments because there may be opportunities for you to indirectly or directly help your peers.

The beauty of startups is they’re flexible and happening in real time, so you can get clarification on something right away when you need it instead of waiting for your next scheduled meeting. Don’t make this a daily habit, but do know it’s there for you when needed.

The important part of these discussions is to listen intently. Asking for feedback this way avoids the “How am I doing?” issue, which most CEOs don’t want to talk about every week.

Yes, you’re important, as is your mental and physical health, and the best CEOs will be there to help you. However, your CEO’s main job is to grow the business and focus on how to drive it forward. Phrasing your questions in a more objective way allows your CEO to comment more on the actions, behaviors and outcomes and to get excited about how the collective company could be improving.

Listening closely also will tell you everything you need to know. When your CEO says something like, I wish we had outlined and agreed upon the details of our growth tests at the beginning of the month instead of doing it more on the fly, there are two things you should take away:

  1. The next time you plan your growth tests for the month, you should outline the details better.
  2. There’s an underlying message: You should improve your planning and execution. Go think about those things, put a framework in place, and apply it to every other aspect of your role.

There are always two discussions happening when you’re talking to your CEO—one out loud and one unspoken. Try to hear what your CEO is telling you beyond the specific subject. Is a bigger trend being illuminated? Is a behavioral pattern forming for better or worse? If you can get on that feedback wavelength, then you’ll have all the information to continually

improve in your role.

This shouldn’t sound like a stealthy game of guess and check with your CEO. Trust is the most essential factor in a sustainable relationship. If you don’t have trust, you won’t succeed and certainly won’t enjoy your time.

In an ideal world, you would meet with your CEO and get direct feedback about how you’re doing based on agreed-upon goals, where you’re doing well, and where you can improve. But management styles and circumstances are different at every startup.

What you can control is being focused and driven, finding constructive ways to operate outside of your self-interest, and still getting the feedback you need. If you can do those things, your emotions and fears will calm down naturally, and you’ll be much happier and more productive.

Learn more about Understanding Startup CEOs.

Dan Slagen
Dan Slagen
CEO & Co-Founder

Currently CMO at ClimaCell, Dan Slagen is a four-time startup executive specializing in scaling global go-to-market functions from early stage to $100M+ in ARR. With experience in both B2B and B2C at companies such as HubSpot and Wayfair, Dan has built teams across marketing, growth, sales, customer success, business development and also founded and sold his own video tech startup. A frequent contributor and advisor to the startup community, Dan has spoken at more than 50 conferences and has been featured in The New York Times, The Wall Street Journal, Forbes, CNBC, TechCrunch, and Bloomberg TV amongst others. Above all else, Dan believes in creativity, drive, and a people first mentality. Learn more about Dan Slagen:
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