Asshole Founders: How to Work With One (And How to Not Be One)
Some of the most successful business leaders are also world-renowned assholes. Here’s how to work with and transform potentially toxic leadership qualities—in yourself and in others.
We’ve all met one or worked with one, become friends with one, or perhaps even been one ourselves. It’s the asshole founder—most often a male CEO who is full of alpha energy, strength, drive, killer instinct, hyper-masculinity, ‘ballsiness’, and a willingness to assert themselves and say what’s uncomfortable. It goes without saying that this type of leader exists outside the startup world (and it’s not always exclusive to men).
In my many years of founding and leading companies, I’ve seen this energy a lot in male leaders at high levels of business. It’s the arrogant jerk who created a billion-dollar company. The domineering jerk at the top who’s built one successful startup after another. The CEO that many employees secretly loathe. Look no further than Steve Jobs, Larry Ellison, and Travis Kalanick, who harnessed this energy to drive massive amounts of value creation. I also highly recommend you watch the recently released movie Blackberry on the founding of Research in Motion, Jim Balsillie’s character personifies this energy to a T.
While these traits are still the ones that are designed to often win in our current system, in 2023, we no longer tolerate this kind of behavior. We recognize it as the patriarch, the rogue capitalist, the colonizer. It’s the ‘conquering’ and ‘taking’ energy that has fucked over the planet. By now, we’ve come to agree that unchecked win-at-all-costs leadership is a dangerous and destructive force in society.
It’s easy (and valid) to criticize this asshole founder type. But as someone who devotes a great deal of time and energy to helping people cultivate self-awareness and become better leaders, I have a somewhat different approach to this—one that doesn’t reject or seek to eliminate these leadership qualities. Whether we like it or not, many of these people are currently occupying seats near or at the top of many large companies. So instead of discussing the ethics of this, I’m more interested in how we can work with these energies and transform them into a force for good.
As a coach, I want to both challenge and humanize this type of leader, so that we can learn how to skillfully work with this energy when it shows up in ourselves and in others. My goal is to explore how we can utilize these traits with awareness in service of positive ends while mitigating their unconscious expression, which inevitably causes harm.
So how does this work? What can you do if you’re aware of this energy in yourself? And what do you do if you’re dealing with this with someone you’re working with?
Traits Are Tools
The first thing to know is that any energy or personality trait is a tool that can have both positive and negative effects.
The positive side of aggressive leadership traits is that they tend to drive results. Being able to say the hard thing, being obsessed with your company/product/industry, and having a strong sense of where the market is going all contribute to business success. Many of the most successful leaders are respected but not well-liked, and assholes don’t care an ounce about being liked.
The downside? They often damage relationships, erode trust, and reinforce existing inequities along the way.
I have known many asshole founders intimately and I’ve seen firsthand their take-no-prisoners approach lead to incredible results, value creation, job creation, and important innovations. But I also observed how their behavior made people dislike and distrust them. It caused employees to hate working for their companies. It eroded trust with partners and investors. Left unchecked, it was clear that this energy had the potential to create significant problems for the individuals themselves, their companies, their employees, their stakeholders, and the planet.
Let’s put ethical questions aside for today and think of these asshole qualities—assertiveness, aggression, ego-centricity, a desire to win at all costs, domineering tendencies, killer instincts, etc—as tools. They can be used for good (making the world a better place) and for bad (wars, conquering, etc.). Rather than seeking to eliminate these traits, let’s explore how to harness them for good.
With this in mind, let’s start by discussing what to do if you’re working with this energy in someone else.
How Do You Work Skillfully With An Asshole Founder?
If this is showing up in someone you’re working with, the first step is to build enough trust with the person that you feel comfortable turning on feedback and honesty between the two of you, and ideally also with the rest of the team.
You could potentially begin by soliciting feedback from this person about how you can do better. Turning on this kind of feedback will ideally create willingness from this person to receive feedback themselves and create greater 360-degree awareness of how they’re showing up. I’ve seen that when someone gets enough evidence from enough credible sources that they are behaving asshole-ish and that it’s not serving their mission, they meet a fork in the road where they have a great opportunity to make real change.
Awareness is the first step to any change, and there are thoughtful ways to support someone in becoming aware that the way they’re relating and communicating isn’t working.
One of my favorite tools for this is the 360 Review, where a group of the closest people in one’s company and life (spouse included) give direct and honest feedback about how they are showing up across many different situations. This gives the person a very clear snapshot of their own behavior. It’s been a powerful tool for helping some of my clients make shifts and see where they're acting in ways that are not productive or conducive to their relationships and larger goals.
Another thing I encourage (and will speak to in greater detail below) is a leadership team-wide Enneagram assessment. This assessment will begin to provide a clear and compassionate context for how people are behaving in different situations. It also provides potential paths for growth and a manual for integrating these harmful behaviors and turning them into something more healthy.
To be clear: you more or less can’t change another person. Galileo once said “You cannot teach humans anything. You can only help them discover it within themselves.”
What you can do is help this person begin to generate awareness of how they’re showing up and the impact they’re having on others. You accomplish this by relaying honest and direct feedback. Then it’s on them to cultivate the willingness to change and make a choice to take action. With a direct and honest approach, you can be a positive influence on someone whose asshole tendencies are running the show—and help them to harness this energy as a force for good.
What’s The Playbook If You’re Aware Of These Qualities In Yourself?
Let’s start by meeting these traits with awareness and positive intent. If you recognize this energy in yourself, there is a great opportunity for you in this lifetime to harness your drive and assertiveness in service of the greater good and significant potential upside for most stakeholders involved. Your work is to cultivate a certain level of emotional intelligence so that the generative aspects of this energy can be heightened while the potentially harmful aspects can be dialed down.
Sounds great—so how does this work? How do you keep your edge and effectiveness without trampling others in the process? How can you un-asshole yourself and still win?
Start With A Self-Evaluation
Integrating any unhealthy pattern starts with self-awareness. Make this your mantra: awareness is the first step to any lasting change. You can start cultivating awareness with some honest self-evaluation: What feedback have you received lately? How do you know this is a problem with your team? How do you perceive you behave as a leader? If you’re honest with yourself, have you noticed that you’re behaving in ways that are not productive or conducive to your larger goals or key relationships?
If your evaluation reveals that you need to make adjustments, it doesn’t mean that you are truly an asshole at your core and are destined to be the antagonist for the rest of your life. It doesn’t mean that it’s ‘just who you are.’ I believe that you (like everyone else) is inherently good. You just have some unproductive patterns and tendencies that stem from your own wounds, past traumas, and cultural conditioning—and that’s something we can work with.
The good news about patterns is that they’re not your core identity and they can be worked with and shifted so long as there’s a willingness on your part. In my experience, most people have some kernel of willingness to change. If this is present, then change is possible.
360 Review & Enneagram Assessment
As I’ve mentioned earlier, my go-to is a 360 Review and an Enneagram assessment to get a clear upfront map of how you’re showing up.
Let’s talk about the Enneagram in a bit more detail. Most asshole founders will score relatively high with a Type 8, The Challenger. This type is known for being self-confident, strong, and assertive, but also ego-driven and domineering. (In the early days of the Enneagram, this type was actually called The Leader, if you can believe it.)
When someone is unaware that they have Challenger qualities, their behavior is what I would consider unintegrated—meaning that it’s showing up in unconscious and unhealthy ways rather than being harnessed appropriately. In the unintegrated state, the person being aggressive is unaware of their emotional impact and how intense they come off to others, and they tend to be oblivious to the negative consequences of their words and actions. They actually think that how they have been showing up is normal or self-evident given the circumstances. By simply bringing awareness to how damaging an unintegrated Type 8 behavior can be, we can open up an opportunity to start working with these patterns in a way that is skillful and ultimately leads to greater communication, collaboration, and success.
The Enneagram model has some excellent guidelines for integrating this type and working with its energy. There are several doorways to explore like letting down your defenses, getting more in touch with your emotions, and relinquishing the belief that you must always be in control—see what resonates most for you and start there.
This evaluation process will help you to interrogate the belief that aggression and dominance are necessary to drive the results you desire. This is often a big part of the problem. If you can begin to see that there may be a better strategy to drive success and high performance, you’ll have a new motivation to change.
Advertise What You’re Working On Like Satya Nadella
Openly share with your team what you know to be true about how you behave and convey the aspects you are actively working on and committed to improving. Furthermore, invite your team to hold you accountable and offer their support whenever you deviate from your desired path. By including your team in this journey, you will receive invaluable support and guidance from those closest to you, enabling a smoother transition toward your desired destination.
When Satya Nadella took over as CEO of Microsoft in 2014, he made it a point to communicate his ongoing journey of self-improvement to his team. He emphasized the significance of continuous learning and admitted to his own areas of growth. He actively sought feedback from employees at all levels and encouraged open dialogue. By demonstrating vulnerability and a willingness to learn, Nadella created a culture where employees felt comfortable sharing their own challenges and aspirations. This transparency and collective commitment to growth enabled Microsoft to undergo a successful cultural transformation and drive innovation within the organization. Nine years later, it’s safe to say that they have been doing great work during his tenure.
Practice Nonviolent Communication
Once you’re open to considering that there may be more effective communication strategies to achieve your goals, then we can start to experiment.
One experiment I often use with my clients is challenging them to have several difficult conversations using Nonviolent Communication. This is often met with skepticism, as it requires a radical shift in their communication style. On the surface, it appears like a much ‘softer’ way to communicate. However, time and again, my clients are surprised and often blown away by the effectiveness and strength of NVC. It is really supportive in saying the hard thing while still being good to the person you’re speaking to.
Hire For Your Gaps Like Steve Jobs
Behind closed doors, it was an open secret that Steve Jobs exhibited certain abrasive tendencies. Now, this revelation may not come as a shock to most of you. However, what truly distinguished Jobs was his remarkable approach to dealing with this aspect of his personality.
He displayed great self-awareness, acknowledging his shortcomings, yet opting not to alter what he perceived as his fundamental nature. Instead, he assembled a group of individuals whose strengths compensated for his own weaknesses, ensuring comprehensive coverage across the team. In essence, Jobs strategically hired individuals who could fill the gaps created by his brusque nature, thus optimizing the dynamics of his team.
Release The Shackles Of Control Like Howard Schultz
One of the most prominent traits exhibited by individuals with an asshole reputation is an overwhelming desire for control. They tend to dominate conversations, paying little attention to the perspectives of others. It is essential to take a step back and evaluate the areas in which you seek control. If there are ten such areas, perhaps we can identify a handful of them that are really contributing to your asshole-ness, and if we relinquish control of those particular areas, then perhaps you and your team will get along with much greater ease. Admittedly, there may be one to three aspects of your business that require a firm grasp from you, and we respect that you may choose to retain control over them. However, there are likely other matters where your tightness is negatively contributing to the team, and it would be beneficial to loosen the reins at least a little bit.
In 2000, after a period of rapid expansion, Howard Schultz decided to step down as CEO, becoming their Chief Global Strategist. Personally, I was surprised to learn that he did this during a time when I would imagine he would have been right in the thick of it, given all the growth Starbucks achieved post-2000. Schultz was synonymous with the company's success and was known for his strong vision and hands-on approach. However, he realized that in order for Starbucks to continue thriving and scaling globally, he needed to empower others and allow them to take on leadership roles. He understood that his intense need for control could hinder the growth and development of talented individuals within the organization. This allowed him to concentrate on what he was great at—strategic direction, brand development, and fostering innovation. Over the next couple of decades, he did periodically come back to the role of CEO, however always handing it over when he felt it wasn’t necessary anymore.
The decision paid off, Starbucks continued to expand and maintain its position as a leading global coffee company. It serves as a reminder that even highly successful and influential leaders can benefit from trusting their team, delegating responsibilities, and embracing a more collaborative approach to leadership.
Looking Forward
Making a shift here will require some ongoing inner work. Enlisting the support of a coach or therapist can help tremendously in the process of letting down your defenses and becoming more emotionally intelligent.
If you have the self-awareness to recognize this energy in yourself—kudos. You can apply the above tools for yourself and seek out feedback, greater self-awareness, mentorship, and coaching to turn these powerful patterns from your Achilles heel into your greatest leadership assets. When integrated, dominance and assertiveness can become healthy traits driving outcomes that benefit not only you but your collaborators, stakeholders, and the world at large.