Kim Scott & Dick Costolo Explore the Fallout of Poor Promotion Practices

Promotions. Feedback. Team morale. These aren’t just management buzzwords—they’re the thorny management dilemmas that can make or break a leader’s reputation.

Few know this better than Kim Scott, author and co-founder of Radical Candor, and Dick Costolo, managing partner at 01 Advisors and former CEO of Twitter.

Together, they unpacked the pitfalls of poor management practices and shared their hard-won insights on how leaders can rise to the occasion.

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Management Dilemmas: The Pancake Problem

  Imagine being told, “Nobody wants you to have this pancake more than me,” only to watch someone else devour it. That’s the management metaphor Costolo used to highlight a common leadership misstep: making empty promises to avoid tough conversations.

“Managers hate having hard conversations,” Costolo said. “But why take a role where that’s a big part of the job? Avoidance doesn’t just delay discomfort—it creates long-term misery.”

Take the case of an employee promised a promotion. Their manager assured them they were “sitting on their hands” waiting for budget approval. But then the manager left, and the promotion went to someone else. The new leadership was caught off guard, with no knowledge of the prior promise. Cue confusion, resentment, and a sense of betrayal.

“That first manager set the employee up to fail,” Scott said. “They made a promise they couldn’t keep, then left someone else to clean up the mess.”

When Feedback Feels Like a Smokescreen

  As if being passed over wasn’t bad enough, the employee then faced a bizarre meeting with their boss’s boss. It went something like this: “I didn’t know you wanted a promotion, but even if I had, I wouldn’t have chosen you. Also, I’ve heard you’re saying negative things—though I haven’t personally seen it.”

“That’s leadership malpractice,” Costolo said. “It’s like, ‘People are saying bad things about you, but not me!’ That’s not feedback; it’s hearsay and demoralizing nonsense.”

Scott agreed. “Feedback should be based on observable behaviors. If you don’t have facts, don’t pretend you do. Leaders need to be candid and clear, even if it’s uncomfortable.”

Why Promotions Shouldn’t Be a Popularity Contest

  One of the biggest traps in management? Treating promotions like ad hoc rewards to placate unhappy employees. Costolo didn’t mince words:

“Promotions shouldn’t be given off-cycle because someone complained. That creates a system where those who speak up get rewarded, and those quietly excelling are sidelined.”

Instead, both Scott and Costolo advocate for transparent, predictable promotion processes. “At startups, an annual promotion cycle is often enough,” Scott said. “It ensures fairness and avoids the chaos of arbitrary decisions.”

Costolo added, “When promotions lack structure, word spreads. Employees compare notes, and suddenly everyone’s frustrated because they realize their manager is just telling them what they want to hear.”

What Employees Can Do

    For employees stuck in unclear promotion paths, Costolo offered a strategy: take control.

“Go to your manager and say, ‘Let’s clarify the metrics I’m being evaluated on. I want to crush those metrics and understand what that means for my growth,’” he said.

Scott chimed in with a warning: watch out for leaders who use words to confuse or avoid responsibility.

“When someone’s language feels like a fog meant to push you away, don’t waste your energy trying to decode it,” she said. “Focus instead on what you can control: your performance and clear communication.”

Leadership Lessons

  Ultimately, the messiness of management dilemmas boils down to one thing: the courage to lead with integrity. “A manager’s job isn’t to make people feel good in the moment,” Costolo said. “It’s to build trust and alignment for the long term. Being forthright might feel uncomfortable now, but it prevents chaos and resentment later.”

Scott agreed. “Radical Candor is about being both caring and direct. It’s not about sugarcoating or dodging hard truths. It’s about showing respect for your team by being honest, even when it’s tough.”

Management isn’t easy, and dilemmas like these can feel like walking a tightrope. But with a commitment to fairness, transparency, and honest communication, leaders can turn tricky situations into opportunities for growth—for themselves and their teams.