In my work of leading and mentoring ambitious data teams as well as non-analysts, I often saw bright minds hesitate to ask questions on topics they felt they “should” know - what they felt might be “stupid questions”. The competitive energy that drives excellence also creates silence around knowledge gaps, undermining the very problem-solving curiosity we need. This is especially common in fields like data science where technical complexity, rapid evolution and high competition make people hesitant to reveal knowledge gaps.
However, as anybody with teaching experience will tell you, there’s no such thing as a stupid question (provided people are being sincere), and often such brave questions help others in the room. People with teaching experience will also tell you that employing bravery in asking questions is a contagious trait - hear someone ask a question, and it becomes slightly easier for others to follow. And, lastly, people with teaching experience will add that you cannot rely on this bravery alone to weed out hesitation from your entire audience.
And so, how does one ensure psychological safety in ambitious, high-performing groups where technical complexity, rapid evolution and competition make people hesitant to reveal knowledge gaps? This question prompted my exploration into ways to create psychological safety in ambitious, high-performing groups such as mine. Here’s what I’ve learnt so far.
Good leadership involves modeling vulnerability
The most powerful signal comes from leaders openly acknowledging their own knowledge gaps. When I said “I don’t understand how this algorithm works—can someone walk me through it?” or “I haven’t worked with this tool before,” I was liberating others from the fear of negative consequences to acknowledge their own knowledge gaps. This has been especially effective in fields like data science that are too vast for any one person/group to know everything. My advice is to do this authentically, not performatively - ask about things you don’t know, not things you secretly do know.
Normalize learning publicly
Create explicit moments where learning happens out loud. This might look like:
- Learning sessions where someone presents a concept they’re currently learning (not mastering)
- Rotating explain-like-I’m-5 presentations where people practice making complex topics accessible
- A team channel for celebrating knowledge discovery rather than prior knowledge
- Code reviews framed as collaborative learning rather than gatekeeping
Reframe questions as contributions
Help your team see that asking questions actually adds value to the group. Someone asking “why did we choose this approach?” might surface an assumption that needs re-examination. Someone asking “what does this metric actually measure?” might reveal ambiguity that would have caused problems downstream. You can actively thank people for questions that made you think differently or caught something important.
Create low-stakes inquiry spaces
Separate high-pressure decision-making from exploratory discussions. This might mean:
- ‘Office hours’ where any question is welcome without meeting pressure
- Pair-programming or pair-analysis time where the explicit goal is mutual learning
- Pre-mortems where the team actively tries to find flaws and gaps in their own thinking
- ‘Stupid questions’ slack threads (rebranding the negative framing can work since owning it removes its power.)
Address competence peacocking directly
In ambitious groups, people often compete to appear most knowledgeable. You might need to explicitly discuss how this dynamic undermines the team. Frame it as: “We’re trying to solve hard problems, which means we need everyone’s actual understanding, not everyone’s performance of understanding.” Some teams even establish a norm where if someone uses jargon without defining it, anyone can call a ‘jargon flag’ without judgment.
Distinguish between different types of knowledge gaps
Help people recognize that there are legitimate reasons for knowledge gaps:
- The field changed (previous approaches are now outdated)
- It’s specialized (knowing deep learning doesn’t mean knowing time series)
- Context differs (your previous company used different tools)
- It’s genuinely new (emerging techniques)
When someone asks a question, occasionally name which category it falls into: “That’s a great question - this is a newer approach that wasn’t common a year ago.”
Build question-asking skills
Some people struggle with not only whether to ask questions but also how to ask these. Coach on:
- Framing questions as collaborative problem-solving (“I’m trying to understand X so I can do Y”)
- Being specific about what they do/don’t understand (“I follow the first two steps but lose the thread at…”)
- Asking questions that advance the discussion (“If we went with approach A instead, would that address…?”)
Create accountability for psychological safety
Make it a team responsibility, not only yours. When someone responds dismissively to a question, address it directly (privately if necessary). When someone says “you should already know this,” that’s a team culture violation worth discussing. Conversely, recognize people who are particularly good at making space for questions.
Use retrospectives strategically
Periodically ask: “What questions didn’t we ask in this project that we should have?” This helps people see that unasked questions have consequences, and it identifies patterns in what people feel they can’t ask about.
3 Core Insights
Psychological safety isn’t about downplaying true competence. It is about building an environment that enables people of all personality types to take risks, voice opinions, sharpen their competence, share knowledge without fear of negative consequences.
- It comes from redirecting competitive energy from individual status protection toward problem-solving. Address competence peacocking directly & build accountability within your team.
- No one shoe fits all. Try a few methods & involve your team in the feedback + improvement cycle.
- Psychological safety is like a muscle that needs regular exercise. Periodically reassess & refine your strategies to safeguard this safety.
When a team identity shifts from “we each show our worth” to “we figure things out together”, questions transform from vulnerabilities into essential tools for driving meaningful progress.
Additional Resources
- This HBR article offers a concise primer on the subject. For those who want a quick intro.
- Hyper Island has a collection of tools & activities to inspire further action, like, ‘Appreciative Inquiry’, ‘Team Retrospective’. (Free after login)
- The Fearless Organization Scan offers tailored plans to build psychological safety for self & within organizations. (Free for self, paid for groups)
- Psych Safety hosts templates, tools & other resources from across the web. (Huge collection of free resources + paid consultation)