SHRM26 Debrief · Leadership & Development · #2501

The Art and Science of Asking Transformative Questions

with Jay Caputo

▶ Watch on the SHRM portal ~79 min, distilled

coachingtransformational leadershiptransactional leadership

"There's a difference between telling and asking. It's a fundamental difference between the two types of leadership."

What it was about

Effective leadership hinges on the interplay between listening and asking questions. By understanding the five qualities that shape any question (open/closed, time, emotional tone, scope, and being/doing/having), leaders can deliberately craft more transformative questions instead of defaulting to transactional ones.

By the numbers

90%

the speaker's estimate that in his manager-coaching role-play exercises, 90% of what managers communicate — even when phrased as a question — is actually disguised advice

108

the total number of distinct question types possible from multiplying the five qualities: 2 (open/closed) x 3 (time) x 3 (emotional tone) x 2 (scope) x 3 (being/doing/having)

Key notes

Practice giving back what you hear ("What I'm hearing you say is...") instead of asking "Do you understand?" to force genuine listening and check understanding.
Evaluate every question against five qualities — open vs. closed, time orientation (past/present/future), emotional tone (negative/neutral/positive), scope (general/specific), and being/doing/having. and deliberately aim for the combination of open, present-to-future, neutral-to-positive, and specific questions.
Purposefully design 'being' questions (about values, feelings, mindset) rather than only 'doing' or 'having' questions (about actions and results), since being is harder to measure and gets taken for granted.

The contrarian takeClosed, past-focused, and general questions are not inherently bad or something to eliminate. The goal isn't to always ask open, future-focused, specific questions, but to use closed, past, or general questions intentionally, for example to set up a better open question, rather than defaulting to them unconsciously. The problem is habitual overuse, not the question type itself.

Take this back Monday

Do this for your team

In your next 1:1, swap 'Do you understand?' for 'What I'm hearing you say is...' and ask one 'being' question about values or mindset.

Say this in your next leadership meeting

Great coaching isn't advice in disguise — it's asking open, future-focused questions that show you trust people to find their own answers.

Watch out for

Asking a string of closed, interrogation-style questions (e.g., repeatedly nailing down deadlines) instead of using closed questions intentionally to set up open ones.
Defaulting to advice-giving ('telling') because it feels good and validating, rather than asking questions the other person can answer themselves.
Over-relying on past-focused questions because the past is 'safer' (known) than the future, which limits transformative, forward-looking conversation.

Fun fact · Jay Caputo

Jay Caputo has logged over 10,000 hours of professional coaching and once served as a certified District Court Mediator in Washington, D.C.

If this landed, see these

↳ Go deeperPersuasion in the Age of AI for HR ProfessionalsTurns deliberate question-craft into a full influence toolkit: reciprocity, liking, social proof, and more.⇄ The counterpointThe Secret Superpower of High Functioning Leaders: How Process Intelligence Creates Aligned, Accountable TeamsGreat questions build one-to-one trust, but this session says that doesn't scale without process behind it.✦ The unexpected oneAre You Okay? Fight Burnout Using PlayThe same shift from transactional to transformative, but through play and curiosity instead of question design.