Five Tips on Avoiding ‘Terminal Niceness’: Former Red Hat CEO Jim Whitehurst

As the chief operating officer responsible for leading Delta Airlines through bankruptcy in 2005, Jim Whitehurst worked closely with bankers and lawyers who specialized in helping distressed companies. He learned that those bankruptcy advisers used the expression terminally nice to describe clients whose cultures avoided difficult but necessary discussions. “Cultures that are terminally nice,” Whitehurst observed, “are so nice that you never have the hard conversations — and you never make the hard changes until you go into bankruptcy.”

When Whitehurst joined open-source software pioneer Red Hat as CEO in 2007, he encountered a culture that prized vigorous debate. In his second week with the company, when the CTO and the engineering team were briefing him on the technology strategy, an engineer interrupted to say that the stated strategy was short-sighted, betting on the wrong technology, and doomed to fail, sparking a massive argument among the team. At Delta, Whitehurst recalled, the engineer would have been fired for publicly contradicting senior management, but at Red Hat, the CTO thanked him for raising the concerns.

And it turns out that the engineer was right, and the debate — painful though it was at the time — allowed Red Hat to course-correct. Following IBM’s acquisition of Red Hat in 2019, Whitehurst served as president of IBM and again found himself in a culture where the cost of disagreeing — especially with your boss — was high. “You tell people it’s OK to have a frank discussion,” Whitehurst said. “Most people are too nice. They don’t want to have hard discussions. So how do you actually get people to go have the hard discussions?”

Vigorous debate is critical for any organization that is attempting to innovate or respond to changing market conditions. When people are willing to question authority and let the sparks fly in discussions, this helps organizations tackle novel problems head-on, view ambiguous situations from different perspectives, and surface the best ideas, regardless of where they come from. Terminal niceness, in contrast, can end in bankruptcy. We recently talked with Whitehurst, who currently serves as executive chair at Unity Technologies and as a managing director at Silver Lake. He shared some practical tips to help leaders stimulate candid discussion in organizations that typically avoid it.

1. Create space for open discussion.

When he joined IBM, Whitehurst noted that the agendas for staff meetings were jam-packed with report-outs, leaving no time for open dialogue. “One of my observations early on,” Whitehurst observed, “was when you tell people, ‘Hey, if you have something, bring it up; let’s talk about it,’ … if they have to actually go schedule time with their boss to bring it up, you’ve created a hurdle that makes that hard.”

Whitehurst mandated that leaders leave 30 minutes at the end of their staff meetings for open dialogue. Employees told him that they were grateful to have the chance to discuss emerging issues or opportunities during regular meeting times, especially in a rapidly changing environment, where it became crucial to have a dedicated space for questioning the effectiveness of current strategies and exploring new ideas. Many teams allocated even more time for open conversations.

2. Publicly thank people for providing tough feedback.

Leaders can lower the cost of disagreement by clearly signaling that they value and appreciate feedback, especially when it’s critical feedback. In meetings at IBM, Whitehurst went out of his way to celebrate colleagues who were willing to speak up and thank them for giving tough feedback, even when the feedback was difficult to hear in the moment.

He told the story of “walking down the hall [one] day, when someone pulled me aside to [raise a concern]. … I was hurrying on to meetings, so I kept walking, but I really reflected on it and how insightful that was, and it changed the way I thought.” Whitehurst recounted the story at one of his all-hands meetings, with tens of thousands of people on the call, and took the opportunity to thank his colleague for taking the initiative to raise a concern.

3. Role-model respectful debate.

As CEO of Red Hat, Whitehurst thought of himself as the company’s head debater: He was engaging in candid discussions on important topics and making sure others did the same. He recalled that IBM was different: “I’d walk in a meeting at IBM … and everybody tried to say, ‘OK, what kind of mood is he in?’ And then it’s like they wanted to structure things around what I wanted to hear.”

To counterbalance employees’ desire to agree with the boss, Whitehurst would sometimes argue the opposite side of what he believed. Once team members realized that he was using that tactic, they felt more comfortable sharing their candid opinions. Whitehurst and his second-in-command made a conscious effort to model the kind of open debate they expected from the team. When IBM employees saw two leaders who respected each other engaging in heated exchanges but walking out of the room as friends, they realized that respectful disagreements were not just acceptable but encouraged.

4. Provide basic skills training on critical conversations.

Encouraging constant debate helps organizations navigate uncertainty, but it can be hard on leaders: They must listen to a constant stream of critiques, manage emotional debates that can boil over, and avoid taking negative feedback personally. To help build these leadership skills, Whitehurst’s team at IBM introduced a framework to help structure and lead difficult discussions, and they required all people managers to receive training on using it.

Reframing feedback can be a particularly powerful way to help leaders have critical discussions, Whitehurst said. He broadcast his view that “if you say something and people just kind of nod or don’t argue with you, that’s the biggest insult. It means they didn’t think it was worth arguing with you about. And there’s no way you’re going to say something that people are going to say, ‘That’s perfect.’ That just doesn’t happen. So the worst you can do is not garner [some] kind of criticism, pushback, or some degree of debate, … [and] you should feel good about pushing back because you’re actually complimenting somebody saying, ‘This is worthy of my time to kind of criticize and debate.’”

5. Demand progress, not perfection.

When someone is trying to build any new leadership capability, including candid discussions, it’s important not to let perfection be the enemy of progress. Learning to lead and engage in vigorous debate takes time. Whitehurst framed stimulating and managing debate as a behavior that leaders exhibited on their best days to emphasize that the capability was aspirational and acknowledge that everyone can have off days.

“If somebody’s off 20% of the time,” Whitehurst noted, it’s OK because “we don’t always have our best days. The problem is, as soon as somebody has 80% of not-best days, it gets tougher because people look at who gets promoted [and infer] the values that a company cares about.” If leaders fail to improve, even after receiving coaching and support, it’s important to tackle the issue head-on. Otherwise, employees will conclude that fostering debate is optional and not really a core element of the culture, he added.

Want to hear more advice from Whitehurst? Watch this conversation and the entire series on the CultureX YouTube channel, on Spotify, or Apple.

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