The Most Underrated Leadership Skill Is Also the Simplest
A beautiful castle somewhere in Germany. Senior strategy consultants from a global firm, gathered for a three-day training. My job: teach them how to ask open questions.
I started with one: "What brings you here today?"
The confusion was immediate. Visible. Almost physical. Did I not know that I was supposed to train them? They were sent here to learn. So teach us. Give us the framework. Show us the model.
It got worse when I established the rule for the next three days: You have to ask two open questions before you can make a statement.
You should have seen the faces.
These were people who had built careers on having the best answer in the room. They had spent years learning to analyze, synthesize, and present — to walk into a boardroom with a 47-slide deck and a recommendation on slide 3. And now someone was telling them that their most important skill for the next phase of their career was not knowing — and being genuinely curious about what the person across from them was thinking.
The Hardest Simple Thing
Open questions — questions that start with what, how, where, when, who — are absurdly simple in theory. A five-year-old asks them naturally. "What's that?" "How does it work?" "Where are we going?"
Then we spend twenty years in education and professional life being trained out of it. We learn to advocate, assert, and advise. We learn that the person with the answer wins. Edgar Schein, the late MIT professor who spent fifty years studying organizational culture, called this the "culture of tell" — a world where knowing things and telling others what we know is valued above almost everything else.
In his book Humble Inquiry, Schein defined the alternative as "the fine art of drawing someone out, of asking questions to which you do not already know the answer, of building a relationship based on curiosity and interest in the other person." He argued this was not a soft skill. It was a safety-critical leadership practice. His research in high-hazard industries showed that subordinates routinely withhold information that could prevent accidents and failures — not because they don't know, but because their leaders never ask.
The only cure, Schein concluded, is for the leader to change their behavior. To go to the team member and say: "I'm genuinely interested in what you see. And I'm listening."
Why Leaders Need This More Than Coaches Do
Open questioning is a core coaching competency — the ICF lists it under "Evokes Awareness" — and we built the Asking Open Questions scenario on RolePlays.ai specifically for coaches in training. But watching the data from 19 practice sessions taught us something broader: the failure pattern isn't unique to coaching. It's a universal leadership problem.
The most common failure we observed? People default to consulting. They give advice. They offer solutions disguised as questions ("How could you bring more of X into Y?" is not an open question — it's a suggestion with a question mark). They make statements instead of asking. They teach models when they should be listening.
This is exactly what leaders do in team meetings, performance conversations, and strategy sessions. They walk in with the answer and ask rhetorical questions to get the team to arrive at it. The team knows what's happening. They play along. And the solution is worse than it needed to be — because nobody was actually invited to think.
When leaders ask genuinely open questions, something different happens. Team members start exploring options they hadn't considered. They bring their own suggestions forward — tentatively at first, then with conviction when they realize someone is actually listening. The collective solution becomes significantly better than anything the leader would have produced alone. Not because the leader lacked intelligence, but because they lacked information that only emerges through genuine inquiry.
The Consultant Paradox
This brings me back to that castle in Germany. Senior strategy consultants are the hardest audience for this training — and also the most rewarding. Because the shift from expert to trusted advisor, in David Maister's framework, is precisely the shift from telling to asking.
Maister's The Trusted Advisor describes the progression every professional goes through: from subject-matter expert, to valued resource, to trusted advisor. Junior consultants deliver analysis, research, and recommendations. They are paid to have answers. But senior consultants who want to reach partner level need something different: the ability to earn a client's trust deeply enough that the client shares their real problems — not just the ones in the brief.
And you don't get there by being the smartest person in the room. You get there by being the most curious.
The rule I imposed — two open questions before any statement — was deliberately uncomfortable. Three days of watching brilliant analysts struggle to suppress the urge to solve, to frame, to advise. Three days of noticing that when they did ask a genuine question, the person across from them opened up in ways that no PowerPoint deck could have predicted.
Months later, the emails came. These senior consultants had started using open questions with their clients. They had shifted from delivering recommendations to facilitating the client's own thinking. Not only did they enjoy it enormously — it also secured their path to partner. Because clients don't promote the consultant who has the best slides. They promote the one they trust.
The Gap Between Knowing and Doing
Here's the uncomfortable truth that Schein identified and our data confirms: most people know they should ask more and tell less. They've read the books. They've sat through the trainings. And then they walk into the next meeting and default to telling — because that's what the culture rewards, that's what feels productive, and that's what twenty years of professional conditioning has trained them to do.
Reading about open questions changes nothing. You have to practice it. Not once, in a workshop exercise, but repeatedly — under realistic pressure, with personas who respond differently depending on the quality of your questions.
That's why we built the scenario. Five AI personas, each bringing a real human problem. You don't know what they want to talk about. Your only tools are genuine curiosity and open questions. No advice. No "why?" No leading. Just pure inquiry.
What happens is revealing. The easy persona gives you depth only if you earn it with quality questions. The moderate persona pushes for advice — can you resist? The challenging persona matches her openness precisely to your coaching quality: surface questions get surface answers. And the very challenging persona fills every silence with anxiety and demands you tell him what to do.
You find out very quickly whether you can actually ask instead of tell. Most people can't. Not yet.
Read the Concept. Then Practice It.
Schein wrote that humble inquiry "becomes more challenging as power and status increase." The more senior you are — as a leader, a consultant, a coach — the harder it is to ask rather than tell. And the more critical it becomes.
Asking Open Questions is free on RolePlays.ai through March 2026. Twenty minutes per persona. No preparation needed. Just show up and ask.
The gap between knowing you should ask open questions and actually doing it under pressure — that's where the real learning lives.
Bernhard Kerres is the founder of RolePlays.ai and works with business schools, corporate L&D teams, and executive programmes to build AI-powered practice environments for the conversations that matter most.
References
Costello, T. H., Pennycook, G., & Rand, D. G. (2024). Durably reducing conspiracy beliefs through dialogues with AI. Science, 385(6714), eadn2401. https://doi.org/10.1126/science.adn2401
Maister, D. H., Green, C. H., & Galford, R. M. (2021). The trusted advisor (20th anniversary ed.). Free Press.
Schein, E. H., & Schein, P. A. (2021). Humble inquiry: The gentle art of asking instead of telling (2nd ed.). Berrett-Koehler Publishers.