Most of my clients are founder/CEOs, and many of them have one or more co-founders. Most of these co-founders are outstanding colleagues and company builders, but a pattern I see in my practice is the co-founder who's viewed as "difficult" in some way and who poses a special challenge to the CEO. (This isn't to say that CEOs are easy to work with. See below.)
"Difficult" co-founders come in a variety of types, and below are five that I've observed, in descending order of frequency and ascending order of difficulty:
1. The Buccaneer
As Reid Hoffmann has noted, startup founders are like pirates: "They both lack formal processes, and are willing to question and even break rules to 'steal' from incumbents (market share and booty respectively)… They act quickly and decisively, and are willing to take risks because they know that the default outcome is failure and the death of the company." [1] But piracy doesn't scale--there's no such thing as a pirate fleet. This isn't to say that startups should become "naval bureaucracies," but a degree of discipline is necessary to support consistent growth. [2]
Some co-founders find it difficult to navigate this transition. The Buccaneer wanted to start a company because they prize autonomy, challenge established norms, and resist formal processes. And these are all necessary qualities in a startup, until they begin to prevent the routinization of operations across product lines, market segments, or time zones. Then the Buccaneer becomes an obstacle to progress, or even an agent of chaos, with the CEO following them around trying to rein them in or clean up after them.
How to work with a Buccaneer:
- Honor their contributions. The company couldn't have launched without them, and this can be overlooked at scale.
- Harness their energy. Their disruptive impact can be a force for good when directed at pockets of stagnation or emerging bureaucracy.
- Clarify their motivation. Some Buccaneers are strictly "zero-to-one" pirates, but many can change when they realize that they're impeding the company's growth.
2. The Olympian
Co-founders generally have exacting standards and set a high bar for excellence. This is one of the reasons they're part of the founding team. Their discernment allows them to make keen judgments on subjects from product and design to hiring and culture, and their determination to be the best can prevent a company from making expedient decisions that are shortcuts to mediocrity.
These qualities are superpowers, but, as I've written before, every superpower has a shadow side, a flaw that accompanies the gift. [3] The Olympian pursues excellence in such a way that it becomes an impediment to long-term success. All decisions must emerge from first principles, every hire must be world-class, no compromises are ever acceptable. While a CEO values the Olympian's exactitude, when applied indiscriminately it becomes a drag on productivity. Rigor has its place, but it's necessary to employ it judiciously and make appropriate tradeoffs.
How to work with an Olympian:
- Understand them. Learn more about the source of their rigor and why it matters so much to them.
- Deploy them deliberately. Focus their discernment on efforts where it will make a meaningful difference.
- Demonstrate your own commitment to excellence. Prove to them that you won't lower standards whenever it's convenient.
3. The Soloist
Many startup disciplines require a capacity for introspection and the ability to work independently, occasionally for long stretches of time. Some people are drawn to these disciplines for this very reason, perhaps because they find interpersonal relationships taxing or perplexing. In a startup's earliest stages, these qualities can be assets on a founding team, enabling members to cover a range of activities independently and maximizing the team's overall productivity.
But eventually the co-founders' collective efforts are insufficient, and gaps emerge. Additional people are needed to augment the co-founders' capacity and expertise. [4] But here the Soloist struggles, unable or unwilling to collaborate or delegate. They insist that workstreams flow through them, and they become a critical bottleneck, operating in isolation while others wait for the results.
How to work with a Soloist:
- Educate them. Show them that their preferred way of working is holding the company back and that interpersonal and collaboration skills can be learned.
- Channel them. Redefine their role so that they can function in a leadership capacity with a narrower scope.
- If necessary, level them. [5] Convert them into an individual contributor so that their working style doesn't impede the leadership team.
4. The Hot Mess
Startup founders sometimes live colorful lives. They can be free spirits who value novelty and spontaneity and who feel comfortable with risk, and these qualities have likely played a meaningful role in their decision to pursue a startup. This is by no means a bad thing, as illustrated in one of Apple's most famous campaigns: "Here's to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently." [6]
Yet these qualities may not be limited to a co-founder's professional life, and they can be taken to extremes. The Hot Mess has a personal life that is sufficiently complicated and disorderly that it impairs their ability to fulfill their responsibilities as co-founder. Sometimes this is evident from the start, and the CEO and others make a calculated gamble that the pros will outweigh the cons, but those odds can shift. And sometimes this is a new development, a function of unanticipated changes resulting in behavior that's destabilizing and unsustainable.
How to work with a Hot Mess:
- Empathize with them. They're likely struggling to regain control over their lives, and a little encouragement can go a long way.
- Get support. Ensure that they're engaging qualified experts and that they're following through with recommended interventions or treatment.
- Set limits. They're undoubtedly likeable and even charming, but ultimately you must hold them accountable should their actions threaten the company.
5. The Rival
Sometimes on a co-founding team it's obvious who should be the CEO. They may have come up with the idea and recruited the other co-founders, or they may be uniquely qualified on the basis of their prior experience. But even when this decision is made amicably, it's typical that as a company succeeds the CEO becomes a far more visible figure both internally and externally, and the other co-founders may eventually feel overshadowed and unappreciated.
In other cases it's not at all clear who should be CEO, and one or more co-founders may feel that they have a rightful claim to the position. Outright antagonism is rare--that tends to break teams apart at this stage--but power struggles are common, and the person who emerges as CEO won that contest. [7] The other co-founders may have begrudgingly agreed to this arrangement, but the seeds of discontent have been sown. Whatever the origins of this attitude, the Rival resents the CEO's prominence and may feel that they're more qualified for the job.
How to work with a Rival:
- Assess the rivalry. Making an underappreciated co-founder feel more significant and valued may be all that's needed.
- Be candid and direct. Resentment usually manifests in counterproductive behavior that merits direct feedback (and ask for feedback as well.) [8]
- Be prepared to escalate if necessary. Sometimes Rivals can't be reasoned with and have to be removed. [9]
Postscript: Who's "Difficult"?
While I'm sympathetic to the difficulties CEOs face, I coach enough co-founders, executives, and investors to know that CEOs themselves are often extremely difficult. This is a function of a number of factors. Power exerts a disinhibiting effect on behavior, and CEOs can act heedlessly without being aware of it. [10] Leaders typically have a high need for control, and CEOs can act in ways that others perceive as excessively directive or forceful. [11] And people rarely offer direct feedback to authority figures, contributing to a CEO's blind spot. [12]
So if you're a CEO dealing with a "difficult" co-founder, consider how you might be contributing to the difficulty. All behavior is adaptive, and when you encounter someone whose behavior you find problematic, you have to understand what they're adapting to. It might be you.
Footnotes
[1] Uber Needs to Transition from "Pirate" to "Navy" (Reid Hoffman, LinkedIn, 2017)
[3] Superpowers and Shadow Sides
[4] Capacity, Methodology, Innovation (On Hiring)
[6] The Crazy Ones (TBWA/Chiat/Day, 1997)
[7] Power Struggles Among Nice People
[8] For more on feedback:
[9] On Firing a Senior Team Member
[10] On the disinhibition of power:
- Power is not only an aphrodisiac, it does weird things to some of us (Vicky Haddock, SFGate, 2006)
- "Disinhibition is the very root of power," said Stanford Professor Deborah Gruenfeld, a social psychologist who focuses on the study of power. "For most people, what we think of as 'power plays' aren't calculated and Machiavellian--they happen at the subconscious level. Many of those internal regulators that hold most of us back from bold or bad behavior diminish or disappear. When people feel powerful, they stop trying to 'control themselves.'"
- Powerful People Take More Risks (Haas News, 2006)
[11] The Effects of Desire for Control on Attributions and Task Performance (Jerry Burger, Basic and Applied Social Psychology, 1987). Also see Authority and Control in Organizational Life.
[12] Watch That Next Step (CEO Problems)
Photo by Tony Harrison.