Every single executive onboarding into a new leadership role fails. So much is situationally new, different and variable that they cannot possibly get everything right all the time. Then, 40% end up getting fired, forced out or quit within 18 months. Stay out of that group by making your inevitable early failures small and intelligent as you ratchet up your current best thinking together with your new colleagues on the way to successful onboarding.

This is a mash-up of insights from Harvard Business School Professor Amy Edmondson’s wonderful new, prize-winning book, “Right Kind of Wrong: The Science of Failing Well” with our executive onboarding frameworks.

The science of failing well

The core premise of Right Kind of Wrong is that there are good failures and bad failures.

That thinking is rooted in Edmondson’s studies of psychological safety, which is required for people to ask questions, admit their own weaknesses or mistakes, offer ideas, and challenge the status quo.

She builds on that by discussing the advantages of pausing to consider how to respond to stimuli, often framing or re-framing the problem or opportunity. This requires:

  • Self-awareness, especially of your own biases – including whether you have a fixed or growth mindset.
  • Situational-awareness, particularly of its consistency, novelty, or variability, and whether it’s high or low stakes.
  • Systemic-awareness, including the linking or “coupling” of interactions across components.

She lays out three types of failures (defined as outcomes that deviate from desired results):

  • Intelligent failures: Good failures necessary for progress. Involve careful thinking. Take place in novel territory. Opportunity driven. Informed by prior knowledge. As small as possible to generate useful learning that advances our knowledge.
  • Basic failures: Stupid ones caused by mistakes and slips. Can be avoided with care and access to relevant knowledge. Known/consistent territory; but didn’t use our knowledge because of mistakes of inattention, neglect, overconfidence, or faulty assumptions.
  • Complex failures: Have not one, but multiple causes, and often include a pinch of bad luck in a variable situation. Potentially catastrophic. Often preceded by subtle warnings.

Application to executive onboarding

Our fundamental executive onboarding premise is that new leaders must converge into organizations and teams before trying to evolve them.

Converge with the humility and vulnerability to learn from other

You are paddling down a river for the first time and you see a little white water. Is it caused by wind? Fish? Rocks? There’s no way you can know – just like there’s no way you can decipher the inevitable surprises in a new organization or team. It’s not a sign of weakness. In Edmondson’s terms, the situation is novel and variable, “inherently and definitionally new.”

Wind? Fish? Rocks? getty

Thus, adopt a growth mindset, viewing the challenges of your early days in a new role as opportunities to learn and grow. Do this with careful experimentation around how to work with others in the organization, iterating through small, intelligent failures to minimize risk. In line with my article on How to Handle Good and Bad Mistakes, these should be intentional failures with minor impact.

“No one should be ashamed to admit they were wrong, which is but saying, in other words, that they are wiser today than they were yesterday.” – Alexander Pope

But, per Edmondson’s Ted Talk on Teaming, you can’t do this on your own. You need the self-confidence and “situational humility” to ask others for help. People are more willing to embrace you if you’re asking for help than if you are telling them what to do. And they’ll forgive your inevitable early intelligent failures – especially if you do this with real humility (freedom from pride or arrogance) and vulnerability (emotional exposure.)


Pause to accelerate, leveraging the Fuzzy Front End between acceptance and Day One to get a head start on building critical relationships and developing going-in hypotheses.

Then, keep converging into the organization in your early days in the role, learning and earning the right to lead.

Evolve the team with both psychological safety and motivating accountability

Pivot from converging to evolving with a workshop to co-create the imperative with your team. Doing this well requires Edmondson’s culture of psychological safety and challenging, motivating accountability. Adopt what she described to me as a “joint problem-solving orientation, seeing problems as shared, and solutions necessarily produced collaboratively.” Tap into team members’ different perspectives to understand the unintended consequences of your choices across the system.

Follow up by implementing a milestone management program, tracking what’s getting done by whom when. Have people share wins, learning, and where they need help. The way they flag projects as green (on track), yellow (need help), or red (off track) is strong evidence about how the team is doing in terms of psychological safety and motivational accountability.

Many teams start with things mostly green until they flip directly to red because individuals are afraid to look incompetent. As Edmondson told me, “You’ll be happier if you’re seeing only green.” But you have to train yourself to be happy seeing yellow. If there’s no yellow, “there’s no way you can be better as a team tomorrow than you are today.” Yellow flags increase as teams move into “learning zones” with individuals asking for and getting help with milestones at risk.

Milestone Management Bradt

Then, over invest to help the team deliver early wins to build their confidence in themselves. Do a role sort to get the right people in the right roles. And keep communicating and learning and adjusting on an ongoing basis – both as an individual leader and as a team, making the intelligent, good failures necessary for progress – and successful onboarding.

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