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3 Steps for Offering Radical Candor to Executives

3 Steps for Offering Radical Candor to Executives

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DILEMMA: Providing criticism to senior executives can be a daunting undertaking. How do you practice Radical Candor with executives, especially if you know they haven’t been receptive to criticism in the past?

We received this question from one of our readers:

How do you solve the problem of senior executives who tend to shut down and adopt an Obnoxious Aggressive position when faced with criticism?

I’ve found that the Obnoxious Aggressive ones are often challenged internally by feelings of embarrassment and/or shame. Over the course of their career, they have been incredibly successful.

And then they finally meet a situation that forces them into a place of realizing they have little or no skills and experience to solve an interpersonal management problem.

All too often they bury the problem, and then they bury the fact that they have buried the problem making it really hard to bring to the surface without a total nuclear blow-up.

What can make this harder is if there is a corporate culture of behaviors designed to avoid shame and embarrassment. T

These behaviors take the form of policies or actions that prevent individuals, groups, and organizations from experiencing embarrassment or threat.

Moreover, as I mentioned above, these defensive routines are “self-sealing.” Because if an action that helps to reduce embarrassment is made public, it would be ineffective. Therefore, it must also be hidden.

For an individual executive do you just put on your body armor and just do it? Or do you have another way? When it’s systemically a part of the corporate culture, what then?

—L

This is a GREAT question and a hard one. Here are my thoughts.

Step 1: Tread with caution

Somebody recently tweeted at me “Tried Radical Candor with my boss. Got fired.” I offered to help the person get a new job, but he had already found one, happily. But when I say it’s not just your job but your moral obligation to offer Radical Candor, I’m speaking to people who are the boss, or who are in a position of authority. When it comes to being Radically Candid with your boss, it’s OK to proceed with a little more caution.

Step 2: Build a culture of self-criticism on your team, with your direct reports

It's a lot easier to lead by example than it is to change other people’s behavior. Here are some specific things you can do to achieve this:

  • Criticize yourself publicly.i-was-wrong-trophyI once bought a 3-foot tall “you were right, I was wrong” statue and gave it to somebody each week. If that’s too corny for you, find some other way to show people when you know you’re wrong and that you appreciate being told so.
  • Explain to your team why you are criticizing yourself. To help explain why being open to one’s own mistakes is so vital for long-term success, one of the executives at Apple whom I worked with bought a copy of Carol Dweck’s book Mindset for all 3,000 people on his team. Maybe do the same for your team?
  • Make it easier and safer for the people on your team to admit to mistakes.I have used a simple technique, “Whoops-a-Daisy,” to do this. Basically, I just bought a stuffed daisy and put it in front of me at every all-hands meeting. I asked people to nominate themselves for “Whoops.” In exchange for confessing to some mistake, they would be granted instant forgiveness and help prevent others on the team from making the same mistake. I would always come prepared with my own story. And for the first few weeks, I had to put $20 on Whoops’s head to get others to share their stories. It wasn’t really that they wanted the money, but the cash gave them “plausible deniability” for playing along. Tom Tunguz, who was on the AdSense team I led, wrote a post describing why he felt this technique was effective.

Step 3: Describe what you’re doing to your boss and to your peers

Show the executive why being open to criticism works better than shutting it down. In an environment that is culturally unaccepting of criticism, people will probably think you’re crazy when you criticize yourself publicly, so be prepared.

  • Tell some stories that show leaders who admit it when they are wrong are STRONGER than those who don’t. Too many execs fail to see how petty bullying makes them look ridiculous. Somehow, they think they are supposed to shut down criticism instead of being open to it. Take some of the stories out of Carol Dweck’s book Mindset. Or, take a look at Steve Jobs’s reaction to antennagate. You could argue that the song at the beginning was maybe a little Obnoxiously Aggressive or defensive, but it was just so funny I’ll give it a pass. But, when he starts talking, the first thing he says is “We’re not perfect.” Another example is CEO James Burke’s handling of the Tylenol poisonings.
  • To demonstrate the benefits of being open to criticism from your own team, come in with some stories of what happened when you started driving a culture of self-criticism on your own team.

And, as you say, keep your body armor on!

I hope this helps. I wish you the very best in your efforts to change the culture and am here any time for follow-up questions. Do let me know how it’s going.

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Key Questions Covered

How do I offer Radical Candor to a senior executive who shuts down when criticized?

The post recommends proceeding with caution when giving upward feedback, especially to executives with a history of Obnoxious Aggressive reactions. Rather than confronting the executive head-on, focus on what you can control: build a culture of self-criticism on your own team first, then use those results as evidence when talking to your boss. Leading by example is far more effective than trying to directly change a defensive executive's behavior.

What is the 'Whoops-a-Daisy' technique and how does it work?

Whoops-a-Daisy is a simple team ritual where a stuffed daisy is placed at the front of all-hands meetings. Team members nominate themselves to share a mistake they made. In exchange, they receive instant forgiveness and help the team avoid the same error. Kim Scott would always come prepared with her own story and, early on, offered $20 to give people 'plausible deniability' for participating. The goal is to normalize admitting mistakes and make it psychologically safe to do so.

Why do senior executives become defensive or Obnoxiously Aggressive when faced with criticism?

According to the post, many executives feel internal embarrassment or shame when confronted with problems they lack the skills to solve — especially interpersonal or management challenges. After years of success, being exposed to a weakness feels threatening. To protect themselves, they bury the problem and hide the fact that they've buried it, creating self-sealing defensive routines that are very difficult to surface without a major blowup.

Is it safe to practice Radical Candor with your boss?

The post is candid about the risks: someone once tweeted at Kim Scott, 'Tried Radical Candor with my boss. Got fired.' The moral obligation to offer Radical Candor applies most strongly when you're the one in authority. When giving feedback upward, it's entirely reasonable to proceed with more caution, read the environment carefully, and build credibility first by modeling the behavior on your own team before challenging those above you.

How can I convince an executive that being open to criticism is a sign of strength?

The post suggests sharing concrete stories of leaders who became stronger by admitting mistakes — for example, Steve Jobs openly saying 'We're not perfect' during the iPhone 4 Antennagate crisis, or CEO James Burke's praised handling of the Tylenol poisonings. You can also draw on Carol Dweck's book Mindset, which shows how a growth mindset leads to better long-term outcomes. Pairing those stories with results from your own team's culture of self-criticism makes the case tangible.

What role does corporate culture play in making upward feedback harder?

When an entire organization is built around avoiding embarrassment, defensive behaviors become systemic rather than individual. The post describes these as 'self-sealing' routines — actions taken to reduce shame that must themselves stay hidden to remain effective. This makes upward feedback extremely difficult because the culture actively suppresses it. In these environments, the best starting point is your own team: demonstrate that openness to criticism produces better results, then use that evidence to make the case upward.

Keep going.

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