How to Understand What Your CEO is Thinking Without Losing Your Mind

Editor’s note: This article is by Dan Slagen, 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. His new book, Understanding Startup CEOs, is out today.

When people ask me about my startup experience, I always give the same three-word answer: Startups are hard.

It doesn’t mean that they aren’t enjoyable or rewarding in awesome ways, but it does mean that they’re far more difficult and quite different from traditional executive roles:

• The pressure is heavier from mental and physical standpoints
• The stakes are higher
• There’s less time
• There’s less money and fewer resources, especially early on
• Everything is changing constantly
• More is expected of you

As if these factors aren’t plenty for you to manage, they compound when you’re reporting directly to the CEO for the first time. 

Successfully working with the CEO of a growing startup requires that you perform at a level you might not be used to from past positions, company cultures or expectations. Plus, expect your relationship with the CEO to present both unique career-building opportunities as well as daunting and overwhelming challenges at times. 

Above all else though, remember that one of your CEO’s core functions is to make sure the right people are in the right positions at all times—which means your boss will be looking at you more times than you might think and asking whether you’re still the right fit given the needs of the company.

Launching a book right now

While this week was an odd moment to launch a book, it was also a timely one. In a matter of weeks, the startup world flipped on its head from being the best startup employee market possibly ever, to a highly selective employer market with free reign access to waves of top-level job seeking talent for the first time since I can recall. 

This means a few things for startup executives. The ones fortunate to keep their job now find themselves under a brighter spotlight to perform and lead, while others who are currently interviewing for new roles or beginning new roles find themselves with new pressures and unique expectations. 

In either scenario, at the top of any of these startups is the CEO, who is fixated on making sure the right people are in the right place. 

And that’s why this week was the right time to launch Understanding Startup CEOs and the mindset you need to successfully work for one. 

State and history

For the startup executives out there, we’ll start with the good news. Startup CEOs are often some of the smartest, most caring and unique folks you’ll encounter in your life. You’ll always look back and be grateful for the time you spent together. 

Now here’s the bad news: Startup CEOs are also some of the hardest people to understand as your manager, especially if you’ve never reported to one before. For them, their life and the startup are intertwined in ways you might never imagine—and if you don’t understand how they think, you’ll never be successful working with one.

The genesis of the book stems from double-digit years in the startup world interacting with hundreds of CEOs, including working for some, advising for others and the list goes on. Over the course of my career I’ve advised a bunch of startups, including CEOs and executive teams, and what I’ve seen more than anything else is executives struggling to be comfortable working with their CEOs. 

While this includes things like planning and forecasting, expectation setting, execution and organizational leadership, it’s the relationship between executives and their CEOs that often determine success more than the tactics. And it all boils down to understanding each other, which is a tremendous and often overlooked challenge. 

Throughout my experiences, I’ve also heard similar frustrations from CEOs saying how they can’t quite get their management teams humming and in sync the way they often envision, and they feel like they aren’t communicating well. 

After one particular week of advisory meetings with two different startup executives, both of which felt like they were struggling to get on the same page with their CEO, I ended up sending them both the exact same advice. 

They both responded with, “This should be a book.” And so here we are. 

From what I found, the number one issue between startup executives and their CEO is a lack of understanding each other, and ignoring the fact that in order to succeed in working for a startup CEO you need to have a dedicated mindset, consistent game plan and framework around that common understanding.

Understanding each other 

In order for startup executives to be successful, they need to put consistent focus into three core areas: 

1. Understanding the mindset of your CEO
2. Your performance outputs
3. Managing yourself

Understanding the mindset of your CEO

“What’s going through the mind of my CEO?” That’s what all of us working in startups want to know and understand—especially those reporting directly to the CEO.

• Are they satisfied or disappointed, happy or unhappy?
• What are they thinking in general, and what are they thinking specifically about me and my team?

These are perfectly normal thoughts to have running through your head, and you should know most leaders have them. Don’t freak out—just acknowledge that this is your reality and embrace the opportunity. 

Coming in each day and reporting to a startup CEO for the first time (and almost every time after that) is a transformational process for most. Working directly for someone whose life is as connected to the success of the business as the CEO’s is to some degree a crazy task to have accepted. 

Your CEO is obsessed with winning and will avoid losing at all costs. Think about it: If the role as CEO doesn’t work out, what’s your boss going to do next? Can you imagine most startup CEOs stepping down to work for someone else? It can happen and sometimes does, but for the most part, CEOs aren’t interested in any role except running and growing a startup. 

Startups are what they truly have a passion for as individuals. Additionally, if this startup doesn’t work out, everything else for them as a future CEO will be more difficult—raising capital, driving influence with the board, recruiting top talent—the list of things on their mind never ends. 

And here’s another thing to think about: Even when those thoughts are racing through their mind, what do most startup CEOs do? Do they come in each day wearing their emotions on their sleeve and letting their direct reports know these kinds of pressures are building up? 

Not usually. Most days they come in and focus on moving the business forward, and you’re none the wiser. It’s an impressive character trait and one you should be alert to as a direct report. 

The truth is, being a startup CEO is a lonely job. Having a little compassion for your CEO can improve your working relationship. 

To quickly review:

• A startup CEO’s life is completely intertwined with the startup
• It’s normal to wonder what your CEO is thinking about you. Don’t freak out.
• Have compassion for your CEO—there’s always more going on than you think

Odds are you’ll never fully penetrate the mind of your startup CEO. They’re a rare breed of people and uniquely built to withstand pressure. Although you shouldn’t stress yourself out trying to figure out what they’re thinking, there are things you should know and can do to make your CEO’s life and your own life easier, including (all of which are covered in the book) understanding:

• They’re betting their life
• They reject no as an answer
• They find loyalty in early hires
• They know it’s broken
• They remember everything
• They hear everything

Performance outputs

As a startup executive reporting to the CEO, you need to perform. And your team needs to perform. 

Your CEO needs to look at your performance at the end of each week, month, quarter and year to get a crystal-clear understanding of your impact on the business. You need to be comfortable reporting on numbers and outcomes. You need to align your input directly with the strategic growth of the business in order to maximize the outputs of your efforts. 

You also need to have a crystal-clear communication plan with your CEO and not shy away from the hard discussions. Your role is to manage your CEO much more than it is the CEO’s job to manage you. If your CEO is telling you what your department should be doing next, then something is wrong. 

It’s your job to bring them along for the development and growth of your department and team in accordance with the overall vision for the company. Share what your vision is for your area of ownership, how it aligns with the company vision, how it syncs with the other departments and how you’re going to get there. 

Do the legwork, but allow room for your CEO to add value. Show plans 80% baked so the CEO can provide input and debate key points. Most important, stay one step ahead and continually connect and build the pieces to advance your department. To maximize your performance outputs, do the following:

• Show customer empathy
• Tell me a story
• Keep a moonshot log
• Share the knowledge
• Be a DAU (daily active user)
• Help others
• Know it’s not fixed
• Phase planning
• Wake up
• Anticipate
• Raise the bar

Managing yourself

Your CEO will provide as much guidance and vision as possible, but you must be an owner. You need to:

• Stay focused
• Help your CEO
• Learn new ways to help
• Keep yourself motivated and energized
• Stay aware of your efforts and impact on the business

Ultimately, you must hold yourself accountable for putting forth the best possible effort to help the business succeed. Your CEO often will be distracted, and you’ll be left to manage yourself and your team. 

Don’t be surprised when they cancel or move one-on-one meetings, and don’t worry if they don’t talk to you for a few weeks during some stretches of business. CEOs aren’t great managers. 

You might have trouble navigating the turbulence, but the strategies that will help you succeed include:

• Don’t lose steam
• Understanding it will be mentally tough
• Be open to change
• Don’t ignore your life
• GSD (Get stuff done)
• Ask for help
• Believe in the mission
• Show up and compete

Putting a plan in action

As I think back on all the time I’ve spent in startup land and all the experiences I’ve had, there’s no single principle that’s the silver bullet to success. 

The key is being able to identify the core strategic principles you’re going to focus on, then remember to focus on them consistently each week. That’s the magic. 

You could adhere to any number of principles, perhaps ranging from three to 20, but make sure you have an implementation and sustainability plan for them. Write them all down. Go through each one every week and ask yourself what you’re doing to advance it. Ask yourself how you should be working best, and keep your CEO informed on each principle.

The only difference between great startup executives and others is that the great ones grasp their core principles and stick to them day in and day out. While that set of principles may vary by startup or CEO, take the time to establish the right ones for your unique role and commit yourself to them. 

That behavior will increase your likelihood of success more than anything else throughout your journey. 

Learn more about Understanding Startup CEOs.