As a leadership coach, I see a recurring theme among emerging leaders: the desire to prove themselves by showing certainty and confidence—even when the world around is anything but. In moments of ambiguity, it’s natural to want to cling tightly to what things we know (certainty)— the data, your analysis, your conclusions. What I find is, the tighter my clients cling to their ideas – the more stress they experience because the battle often becomes more about defending their ideas (enter ineffective defensive leadership behaviors) rather than more thorough exploration of their decision. Why is this a problem? Because when it becomes a defence of their ideas, it then often leads to perceptions that those asking probing questions are challenging to their competence.
In order to be most successful, leaders need to get used to the poking and prodding, otherwise known as “organized skepticism” to ensure they are constantly growing their decision-making skills.
Organized skepticism
In her book Thinking in Bets, Annie Duke describes organized skepticism as a way of approaching decisions through structured doubt. It’s about asking, “What if I’m wrong?” before the world forces you to find out the hard way.
“Skepticism is about approaching the world by asking why things may NOT be true, rather than why they may be true.” — Annie Duke
This isn’t about being negative. It’s about being thorough. When done well, organized skepticism isn’t confrontational—it’s collaborative. It’s a team practice that strengthens ideas instead of attacking them.
But to truly adopt this mindset, leaders must also confront a deeper bias: our tendency to judge the quality of decisions based on outcomes.
“We’ve been trained to equate the quality of a decision with the quality of its outcome. That’s a problem. Outcomes are influenced by many things—most of which are outside our control.”…”We need to stop thinking in black-and-white terms: wrong or right, smart or dumb, success or failure. Good decisions can have bad outcomes, and vice versa.” - Annie Duke
So, when a past decision led to a good result, it’s tempting to assume it was “right.” But it may have been lucky. And when someone challenges your current thinking, that tension may not be about your ability—but about improving your process (i.e. growing the edges of your decision-making skills).
So, how do you lead with this mindset—and encourage it in your team?
1. Shift from “being right” to “getting it right.” Let go of needing to defend every decision. Instead, aim to make decisions that can withstand scrutiny and evolve with new information.
2. Ask better questions. Try: “What am I missing?” or “Where could this break down?” These questions turn feedback into a team sport rather than a personal critique.
3. Model non-defensiveness.
When someone questions your assumptions, try: “That’s an interesting angle—let’s explore it.” Curiosity disarms defensiveness.
4. Normalize dissent.
Make it clear that respectful disagreement is not just accepted—it’s expected. This takes practice but once teams get the hang of it and feel safe about challenging ideas (even those brought up by leadership), that’s when truly innovative work can happen.
5. Reward thoughtful challenge.
Recognize team members who spot risk, question assumptions, or flag blind spots. When you celebrate accuracy over certainty, you build wiser teams.
What can you try now?
In fast-moving, high-stakes environments, certainty is seductive—but dangerous. Good leaders will have answers, but great leaders will ask better questions.
Leaders who invite organized skepticism create smarter, more resilient teams. They trade ego for accuracy, and personal validation for collective learning. The decision-making process for the entire team improves.
The next time someone questions your analysis, I would challenge you to NOT take it personally. Take it seriously. It might be the most valuable feedback you get all week.
What’s one idea or assumption you’ve been holding onto—maybe too tightly?
This week, invite a trusted peer to poke holes in one of your upcoming potential decisions. Then listen without defending.
Reference:
Annie Duke (2018). Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts. Portfolio (Penguin Random House).
If you are looking for a more customized leadership development experience, leadership coaching may be the better option to get you to your professional development goals faster. Book a complimentary “Discovery Call” to discuss your goals and see if working with a leadership coach might be the way to go.