10 Traps First-Time CEOs Fall Into (and How to Avoid Them)
The TL;DR - The path to first-time CEO success is littered with landmines. I’ve stepped on most of them so you don’t have to.
Here are the 10 biggest traps I've seen first-time CEOs fall into, and how to avoid them.
- Pretending you have it all figured out.
- Being blind to your blind spots.
- Focusing too heavily on the short term.
- Failing to focus on what’s most important.
- Sitting on important decisions too long.
- Failing to puncture the CEO bubble.
- Overrelying on authority to lead.
- Forgetting that people are watching.
- Failing to ally with your board.
- Failing to align your team and org.
Below, I'll drill into each one—and most importantly, share actionable ways to avoid getting caught in it.
So, you just got the nod as CEO. The top dog. The head honcho. The big cheese.
Way to go!
I'm sure you have dreamed of this—and put in the hard work to boot.
Get’s me thinking about my first time at the helm...
In the early 2010s, I declared a new 5-year goal on my career plan: to become a PE-backed CEO. And I attacked that goal with vigor.
I read everything I could. I took on new job assignments that would help me stretch, grow, and build new leadership muscle. I meticulously observed the CEOs in our portfolio companies. I created a vision board (true story).
Flash forward to 2016. A portfolio company I was on the board of was sputtering. So it was time to call my own number and get things back on track. Despite being unqualified by most conventional standards, this was my chance... and I wasn't going to waste it.
If you’re anything like me when I first found myself in the chair, you really want to be a kick-ass CEO. You haven't gotten this far in your career by aiming for average. And that isn't going to change now.
You want to seize the opportunity. (Cue the Hamilton soundtrack. "I'm not giving away my shot!")
And in order to rock it in this new role, you recognize that you will need to build and use new muscles:
→ Allocating capital.
→ Setting a clear vision.
→ Partnering with a board.
→ Setting the organizational culture
→ Building and leading a high-performing executive team.
The buck now stops with you on key, high-stakes decisions. You’re up for the challenge, but it is a lot... and you feel the weight of it.
But here's the real problem...
The unfortunate reality is: most CEO roles don't come with an instruction manual. I dunno about yours, but mine didn't. Sure would have be a lot easier if it did.
Instead, you are enrolled in the "sink or swim" School of CEOship.
If you're lucky, you have a helpful board, a trusted group of mentors, and an awesome team to lean on. But despite the support, each new day seems to present a new type of challenge that you haven't encountered before.
The stakes are high, and all eyes are on you.
No pressure. 👍
But here’s the good news: you don’t have to feel your way through the sometimes cold, dark wilderness of first-time CEOhood alone.
Plenty of others have walked the same path before, including yours truly and the dozens of first-time CEOs we appointed at my last private equity firm (famous for the first-of-its-kind CEO in Training program we created).
So learn from my mistakes.
Learn from the challenges other first-timers I've hired and worked with have faced... and how they've navigated them.
Stand on the shoulders of those who have come before you.
I wrote this post to help.
The path to first-time CEO success is littered with landmines. And I’ve stepped on most of them so you don’t have to.
Here are the 10 biggest traps first-time CEOs fall into, and how to avoid them.
10 First-Time CEO Traps... and How to Avoid Them
Trap #1: Pretending you have it all figured out.
It's natural to feel in over your head. But you don't have to "fake it till you make it."
Feeling like an imposter is among the most common, yet most insidious issues first-timers face. And its symptoms can feel downright icky—anxiety, insecurity, even guilt.
When we are stricken with Imposter Syndrome, it feels like a nasty little creature —which we'll call the Imposter Gremlin—is permanently perched on our shoulder. “It’s just a matter of time before everyone will learn you’re a phony,” the Imposter Gremlin tricks us into believing. It causes us to doubt our abilities and feel like we don’t belong in the role.
This sets off a nasty chain reaction.
You overcompensate by trying extra hard to project competence and confidence.
But this makes you come off as a know-it-all. And no one wants to work for a know-it-all. So this starts to eat into your approval ratings from your new employees.
You sense this, and realize you’re losing the locker room.
So you start to question yourself even more. You become overridden with fear of failure.
This impairs your decision-making, causes you to avoid taking risks, and makes you reluctant to delegate and empower others.
Things spiral. And pretty soon, you’ve lost control. All because of your irrational fear of being exposed as a fraud—despite being put into the CEO role for a reason.
What to do about it?
Eat a slice of humble pie. Humility is an attractive and important leadership quality. The most effective CEOs I know masterfully manage the tension between humility and confidence. They understand and acknowledge their limitations, but maintain confidence in their ability to learn, grow, and figure things out.
The best way to get the Imposter Gremlin off your back: acknowledge your weaknesses, blind spots, and insecurities with your team at the outset.
It makes you human. It starves your Imposter Gremlin of oxygen.
Then enlist your team's help: "I'm going to need a lot of your help in those areas."
But (and here’s where the confidence part comes in), reiterate your commitment to winning: "...Even though there are aspects of the role that are new to me and I’ll need your help to navigate them, you should know one thing: I'm going to bring every ounce of what I've got to help us succeed together."
Trap #2: Being blind to your blind spots
According to a study by Green Peak and Cornell University, the strongest overall predictor of executive success is self-awareness.
Leaders who have a clear view of their greatest talents and skills–and their deficiencies and blindspots–have been shown to be more promotable, better influencers, and ultimately, more effective leaders.
Self-aware leaders know who they are. And they know who they aren't.
They are more aware of their limitations and weaknesses, and therefore able to hire people who complement them
They aren't afraid to ask for help or seek perspective.
They have a better understanding of how they impact people—employees, investors, etc.
These are all good things, and it's easy to understand how these things help improve the overall odds of CEO success.
But here’s the thing: thanks to a cognitive bias called the Dunning-Kruger Effect, the truth is that most executives are less self-aware than they think.
Dunning and Kruger, researchers at Cornell University, investigated peoples’ perceptions of their own competency. Their main conclusion was that people with a lack of skills in any area also lack the competency to realize their lack of skills. In other words: it can cause us to overestimate our own competence, and makes us blind to our blind spots.
Unless you're that unicornish breed of all-arounder super-CEO... chances are: there are things you’re not good at. And because of the Dunning-Kruger Effect, it stands to reason that you may not be fully self-aware of these things.
This may prevent you from seeking the support you need. It could prevent you from surrounding yourself with people who complement you. It could cause you to try to take on everything yourself.
What to do about it?
Find people who know you well and can help you deepen your own self-understanding.
Having a coach help you do a formal 360 is a great way to approach this. But you can also do it the ol’ fashioned way. Ping 5 people you’ve worked with before. Ask them out for coffee. Sit them down and ask them: "When have you seen me at my best? And what made me so effective then? Where have you seen me struggle?"
Take this intel, find the themes, and internalize them. Then use this to (1) lean into the things you naturally do well, and (2) surround yourself with people who can complement you in the areas that aren't your forte. Find the Bens to your Jerry. The Mulders to your Sculley.
Trap #3: Focusing too heavily on the short-term
Our human brains are wired to favor near-term reward (or the avoidance of near-term pain) over long-term reward.
Because of this, our default mode as humans is to overweight the short term in our decision-making. This tendency can cause leaders to overly fixate on what’s right in front of us. On the fires you need to fight in your business today. On delivering this quarter's bacon.
Surely, CEOs can't neglect the short-term. If you want to keep your job, is important to hit this year’s targets.
And furthermore, you probably recognize how the short-term and the long-term are interrelated. An atrociously bad quarter that drains cash reserves could, in fact, jeopardize long-term prospects. You need to put points on the board today in order to be alive tomorrow.
However, we also know that making long-term decisions is important to long-term success. Research from McKinsey shows that firms who tend to make decisions predominantly focused on the long-term delivered considerably greater long-term growth than their short-termist peers.
So, for CEOs and their companies to experience the benefits of long-termism, we need to overcome our genetic predisposition to short-termism. We need to wear bifocals and develop the habit of looking at our business through short and long-term lenses.
What to do about it?
Embrace a "both/and" mindset. Create and cast a bold and purposeful long-term vision for your business (the long-term part). And use this long-term vision to make decisions about what you’ll focus on this year and this quarter to move the business in that direction (the short-term part).
This helps you ensure that near-term decisions—about where to focus this month, what to prioritize this quarter, etc.—are being made with the long-term in mind.
Trap #4: Failing to focus on what’s most important
Dave Packard, the legendary founder of Hewlett Packard, has a great quote I sticky-noted to my computer monitor as a CEO: "More companies die from indigestion than from starvation."
A common first-timer mistake is to take on too much.
You want to prove yourself. You want to make your mark. You’re eager to make a splash. So you develop an addiction to more. More products. More speed. More work. More partnerships. More meetings.
But by and large, the more things we try to do, the less we tend to accomplish.
So what if the key to accomplishing more as a CEO was to do less and obsess?
One of the most important muscles to build as a new CEO is the ability to discern between "the vital few" and "the trivial many," as Greg McKeown puts it in his book Essentialism.
It’s always better to identify the 3 - 5 most important things and move them a mile, than move 100 things (the “trivial many”) an inch.
What to do about it?
Create a stop doing list.
Steve Jobs said, "[Achieving] focus is about saying no." So create a stop-doing list.
As you’re establishing the short list of priorities your team is going to focus on this year or quarter, and being explicit about what you're not going to do.
A “stop doing list” defines the things that you are explicitly saying "no" to. That way, when one of those shiny objects glimmers in the distance and your team feels the urge to go pick it up, they have clear marching orders to leave it be.
Trap #5: Sitting on important decisions too long
At its core, the role of a leader can be reduced to making and acting on decisions.
Big ones. Smaller ones. Many per day. Lots of 'em.
For this reason, decisiveness and resoluteness are among the most important traits to CEO success (The CEO Genome Project).
The most successful CEOs don't necessarily stand out because they make great decisions all the time, but because they tend to be more decisive—making decisions earlier, faster, and with greater conviction.
In fact, according to research from the awesome book The CEO Next Door, decisive CEOs are a whopping 12x more likely to be high performers!
But despite the importance of making speedy decisions, we don't live in a world with perfect information. The info needed to make decisions fast isn't always knowable.
What’s more: many first-time CEOs face some amount of underlying fear of failure. This is your first CEO role. It is your opportunity for a breakout performance. So you don’t want to make the big mistake.
This can create excessive caution on the part of some new CEOs, and cause first-timers to sit on important decisions for too long.
It can also cause CEOs to get involved in too many decisions in the org.
What to do about it?
Follow "The Bezos Rule." Get comfortable making decisions with imperfect information.
"Most decisions should probably be made with somewhere around 70% of the information you wish you had."
Make fewer decisions. Decision fatigue is real, and contributes to slow decision-making. So delegate decision-making authority, and entrust your people to make the call.
Learn to distinguish between 1-way and 2-way doors. Reversible decisions are what Jeff Bezos calls “2-way doors.” 2-way doors allow you to move faster and change course as needed. But 1-way doors deserve greater diligence and decision confidence.
Trap #6: Failing to puncture the CEO bubble
Dutch leadership scholar Manfred Kets De Vries famously quipped:
"Leaders are surrounded by walls, mirrors, and liars."
There isn't a role for which this is more fitting than CEO.
As CEO, people will tell you what you want to hear, and will be fearful of telling you things they believe you don't.
This can trap you in what Nandan Nilekani, co-founder of Infosys, called "the good-news cocoon." I’ve referred to this as The CEO Bubble.
How does The CEO Bubble form?
Thanks to generations and generations of social conditioning, peoples’ subconscious brains have been wired to think, "Challenging the person in authority, and risking our standing with them, is dangerous and should be avoided."
Because ofr this, for as long as people in authority have existed, there have been people who sought to appease them. Anyone who has watched Game of Thrones will get this.
But getting trapped inside the CEO bubble can be a big issue.
First-timers who are stuck in the CEO bubble lose touch with reality.
They miss out on hearing important perspectives and insights.
Their glasses can become rose-colored.
What to do about it?
Create the conditions that allow for transparency.
Don’t kid yourself: if you think that just by telling your people "I want to hear what you really think!" the floodgates will open on the truth... think again.
CEOs need to actively create the conditions that deflate The CEO Bubble.
Recondition your team to develop greater comfort with speaking their mind.
To do this, proactively solicit—and reward—disagreement. Project an open, approachable attitude. Silence your own opinions until you've solicited your teammates’. Ask for people to take the other side of the argument as you. Avoid penalizing respectful disagreement.
Trap #7: Over-relying on authority to lead
As CEO, you are the most powerful person within the organization.
But over-relying on that power–let alone wielding that power as a weapon (whether intentionally or not)—can become a real problem.
Surely, there is a time and place for more authoritative leadership, like crisis situations. In certain situations, you will have to make the call, and do so quickly and sometimes without input.
But it is when this becomes a CEO’s default mode that it becomes a problem.
Using your power to issue orders, unilaterally make decisions, or coerce people into compliance with you is a bad idea with big consequences.
Giving orders can cause resentment, erode trust and confidence, and undermine your results.
According to the Harvard Business Review, two out of five new chief executives fail in their first 18 months on the job, which in many cases, "has nothing to do with competence, knowledge, or experience; but rather, with hubris and ego and a leadership style out of touch with modern times."
Gone are the days when the old industrial command-and-control style of leadership was effective and accepted by employees.
In order to succeed in the modern era, CEOs need to learn to make room for and work through others.
They need to help build, and then lean on, the judgment of their team.
They need to empower others to make and own decisions.
They need to hire good people, cede responsibility to them, and let them run.
What to do about it?
Silence yourself. To create room for others to make and own decisions, silence yourself.
Because of your position of power, your people are likely to perceive your opinions and viewpoints as gospel. Even the most half-baked idea offered by a CEO can be interpreted as a direct order.
So except in cases where it feels appropriate to lead from the front, get in the habit of offering your opinion last (if at all). Consider your primary job to elicit the best thinking from your team.
Remember that your job is to build up the team's capacity to make decisions themselves, not make them dependent on you.
Trap #8: Forgetting that people are watching
First-time CEOs need to recognize something very important:
As the CEO, you're always on stage, and your microphone is always on (metaphorically).
Whether you know it or not, people are watching your every move, and taking their cues from you on what's expected, acceptable, and encouraged.
What you say, how you act, and what you project (sometimes unknowingly) can end up getting amplified throughout the organization.
This can feel like a lot of pressure.
But effective CEOs recognize that despite the potentially problematic aspects of this reality, it creates an opportunity.
What to do about it?
Use the platform to model the behaviors you expect of others. Establish clear team values and expectations. Model them. Ask your team to hold you accountable for living into them, and maintaining a high do/say ratio.
Early in his time at the helm of Ford, Alan Mullaly, who is credited with leading one of the most epic turnaround in the modern era, laid out 16 expected behaviors for Ford employees. Things like "ensure process discipline," "Have a 'can do, find a way' attitude," and "Set high expectations and inspire others." He printed them on a laminated card, gave them to his team, and created accountability for living into them. He also asked his team to hold him accountable for living them.
Trap #9: Failing to ally with your board.
For many first-timers, one of the most unfamiliar parts of the job description is partnering with a board.
Although CEOs sit atop the org structure, most still report to a board. And that board has the power to fire them, set their compensation, make or overturn strategic decisions, approve budgets and capital expenditures, and so on.
If you’re interested in keeping your job (*hands raise*), it is therefore pretty darn important that a CEO develop a rock-solid partnership and a strong sense of alignment with their board.
The best CEO-board relationships are the ones where:
- everyone is on the same team
- the CEO and board partner to take shared responsibility for growth, solving challenges and mistakes, and celebrating successes
- the CEO and board are aligned on how they will work together, what they can expect of one another, and what role the board will (and won't) play.
But partnering with a board in this way is trickier than the type of managing-upwards that many first-time CEOs are used to from prior toles.
Instead of having one boss as you have been accustomed, you now have a handful. And they'll each have different personalities, interests, and sensitivities.
What to do about it?
Develop a simple board charter.
Take the lead on creating a simple charter with your board—nothing fancy—that establishes the expectations and rules of engagement.
How/when will we communicate?
What do you expect from me?
What should I expect from you?
What types of issues can I call on you to help me think through?
What types of issues do you want to be made aware of?
This doesn’t have to be overly formal, but talking through this upfront—and writing down your agreements—can save you from big misalignment issues down the road.
Trap #10: Failing to align your team
Have you ever tried to drive a car when the alignment is out of whack? When all of the tires are pulling in different directions.
Sometimes leading a business can feel a bit like this.
When the people on your leadership team are on different pages—when one person is pulling in this direction, and another is pulling in that direction—is can make it really difficult to go fast in the short-run, and far in the long-run.
And like a car with wheel alignment issues, best case scenario, a misaligned team requires a lot of the leaders effort to keep the thing on the road. But worst case scenario, a misaligned team can end up running their business into a ditch.
When leadership teams are out of sync in this way: it can be really costly to a business.
Wasted time. Missed opportunities. Plummeting morale.
And these things inevitably translate into real performance challenges.
And the alarming reality is: too many organizations aren’t, in fact, pulling in the same direction. A 2017 study by Modern Survey on “The State of Employee Engagement” shed light on this.
Only 37% of employees polled said they have a clear understanding of what their organization is trying to achieve and why. Only 20% of workers said they have a clear “line of sight” between their tasks and their team’s organizational goals.
Author Steven Covey compared similar results from a 2004 study by Harris Interactive to a soccer team: If the same reality existed on the soccer field as in the workplace, then only four of the eleven players on the field would know which goal was theirs. Only two of the eleven would know what position they played and what exactly they were supposed to be doing.
Misalignment of this sort can be problematic—at worst, disastrous. It is a surefire way to jeopardize your success as a CEO.
What to do about it?
Slow down and get aligned. Take the time to get your leadership team–and then broader organization–onto the same page on 6 simple, but essential questions: Why do we exist? (purpose) // How do we roll? (values) // Where are we going? (vision) // How will we get there? (strategy) // What needs to happen next? (plan) // Who do we need aboard? (people)