Dealing with Crazy Startup Leaders: A Quick Guide

Startups are an important part of the tech world, often serving as the first employers for software developers, architects, engineers and the like. Unlike established firms, they’re often led by untested founders. More than half will fail in their first five years, according to the website Small Business Trends; of those, 46 percent will close their doors because of incompetence, and 30 percent because of an imperfect management team.

That means founders and investors work under considerable pressure, and it’s inevitable that some will behave in unreasonable ways. Startup veterans tell stories of hair-trigger tempers, unrealistic deadlines and impulsive decisions that led to tanking morale, if not business disaster. Yet they often hang on.

“You get to this point where you’re at the craps table and you’re just saying, ‘one more throw,’” said Adam Mosston, who spent nearly 10 years working for a video-technology startup in Boston. “And you’re saying, ‘I’m in so deep now, I’ve got to keep going.’ And you’re consuming more of your life and your time and your effort and your fear—all because you believe in the damned thing.”

The Art of Positive Confrontation

Startups usually don’t have a function in place for working through conflict, observed Alice Ain Rich, a career counselor based outside of Boston. At first glance, that leaves employees with few options, such as putting up with bad behavior, confronting the founder, or quitting. However, Rich doesn’t believe the situation is that cut-and-dried. There’s confrontation, she explains, and then there’s confrontation.

“My advice to people is to create what I call a ‘a positivity sandwich,’” she said. Rather than go toe-to-toe with the founder at the outset, begin the conversation on a positive note. For example, she describes one company whose founder publicly humiliated anyone who dared to offer a constructive critique, even when he asked them to.

In a case like that, “tell them you love the company’s mission and really like making a difference,” Rich said. “Then explain that one thing getting in the way of your ability to perform is that you feel you can’t be honest with feedback. That’s making me feel very anxious.” Once you’ve put that on the table, say you want a discussion that will allow you to continue contributing to the founder’s vision, “so we can continue to work well and achieve a lot more together.”

Such an approach—starting on a positive note, stating the issue, then ending with a constructive desire to solve the problem—is far more effective than “just hammering someone with what’s bothering you,” Rich said.

Opening with a positive statement or a compliment allows your boss to relax in their body language, listen differently, and be more open to what you have to say. “If you end with a positive, that’s what the person will take away with them,” Rich said. “You’ll get more accomplished.”

Play the Startup Game Well

In many cases, however, the direct method may not be the best approach. After all, even a carefully planned confrontation has its risks. It’s the same for senior leaders and founders themselves, who often have to deal with an unpleasantly willful board chairs or investors.

“To me, it’s when a manager or VP or CEO behaves erratically and I can’t predict it,” said Marty Fahey, a serial entrepreneur in Boston who now works as a troubleshooter for investors with challenging organizations on their hands.

“Some people are just rude and have bad social skills. They don’t deal with people well, they’re just not nice people,” Fahey said. “Then there’s another set: They’re erratic, it’s hard to follow their chain of thought, and it’s even hard to understand the direction you just got.” In Fahey’s experience, such people aren’t simply mean, “they’re so illogical and irrational that you come to question their sanity at some point.”

Fahey recalled an investor and board chair of one company who arrived at his first meeting, sat down, pounded his fist on the table and ordered, “Marty. Coffee.”

“It’s one of those situations where you think, ‘I would never do that to somebody,’” he said. “But now that you’re there, and this is an important person in your business life, you have to ask how to start this relationship in a way that will work.”

Faced with the trade-off between getting coffee or “wasting time” on a more confrontational approach that could have ended badly, Fahey got the coffee. But over time, he began managing his board chair in a way that benefitted the business’s long-term objectives.

“One of the things you have to decide early on is that you’re never going to change their personality,” he said. “And if you don’t get that into your head and deal with it, you’ll be forever frustrated.”

In that case, Fahey’s solution was to determine where the board chair could be helpful, and avoid situations where “he’s going to do something that you know will piss you off.” His first move was simple: Have coffee ready before the man arrived. But more important, he stayed in touch with other CEOs in the investor’s portfolio. That way, Fahey was always prepared for what topics had him “all hot and bothered that week.”

One time, Fahey learned the investor was harping at his CEOs about channel distribution. “So when he walked into our board meeting, I said in my presentation, ‘You know, we’ve thought a lot about it and we really need to do channels.’ And all of a sudden, instead of beating me up, he goes, ‘You’re exactly right.’”

The lesson, Fahey said, is “if someone’s not going away, and they’re never going to change, you have to play the game the best you can.”

Such dynamics can apply throughout the startup. A programmer, for instance, might find themselves in a similar situation with their startup’s founder. “You’ve got to realize that he’s never going to change and his boss is never going to change,” Fahey stressed. Then you’ve got to decide whether you can learn to deal with it or not.

“You don’t want to ultimately get into a situation where you’re so frustrated you go to commiserate with other people in the company about how crazy your boss is,” Fahey said. “You’ll become one of those people that are spreading bad news and you’re building relationships with people about why your boss is so crazy.” That dynamic, he added, can be detrimental to both your time at the startup and your long-term career.

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