The Questions Leaders Ask – Field Guide

I’ve spent over three years collecting high-level questions I use across an array of leadership and business contexts. It’s been extremely helpful and a resource I get asked about often. These questions are research-backed, personally tested, and free for you to use and keep forever.

I’ve lost count of the hours spent researching and curating this list. I care about questions because they make me better, specifically a better leader, manager, husband, and friend. The company I founded, Kestryl Edge LLC, has a mission to Build Better Leaders. So, if you find my trove valuable, like it, send it to someone else, or bookmark it for future reference. Any action you deem appropriate for the value you received.

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In this article we will:

1. Introduce asking questions as a core component of active listening.
2. Review literature sources on why we care about asking questions and active listening.
3. Review the basic rules for respecting boundaries and privacy.
4. Illuminate the core research findings I’ve found over the years while compiling this resource.
5. Provide all of the best high-value questions I’ve collected organized by use-context.

Sound useful? Let’s get after it.

Fishing for Better Responses

Do you ever pass someone in the hallways and ask, “Hey, how’s it going?” and they give a boilerplate water-cooler response like, “Oh you know, living the dream!” and then you say, “Yep, I hear you there,” and that’s it? Or maybe you get one of these:

• “Can’t complain!”
• “Hanging in there.”
• “Ready for the weekend already.”

These make me chuckle every time. They are so shallow and tell you absolutely nothing. I hear, “I have nothing to share with you. Don’t talk to me.” Today we’re establishing how we fish for better responses.

Lately, I’ve been writing on trust and how critical it is to healthy culture. One theme that keeps coming up in the literature is that we can build trust by active listening. Where do we start? How do we have better conversations and actively listen? Take a guess.

Survey says: WE ASK BETTER QUESTIONS. It’s just that simple, folks. It turns out, having better conversations with people isn’t about you talking at all. It’s about you not talking. When you do talk, it’s to ask another great question so your conversation partner keeps talking. Then you listen. You listen well.

This is widely proven in the literature. I’ve selected a few of my favorite sources that illustrate this and a few other notes that serve as groundwork here. Facts first, then actionable advice for the prudent student.

The Facts

• People who ask follow-up questions are more liked by their conversation partner (Huang et al., 2017). Huang et al. published an interesting paper out of Harvard that looked at hundreds of speed-dating conversations. They found dates who asked follow-up questions were more liked by their partners and got more dates. More follow-up questions, more dates.
• High-quality listening is shown to boost the speakers’ self-confidence, autonomy, and self-esteem in difficult conversations (Itzchakov & Weinstein, 2021). Across two experiments, they found that when people discussed their own prejudiced attitudes with a listener who was attentive, empathic, and nonjudgmental, they experienced greater autonomy and relatedness during the conversation and reported higher state self-esteem afterward. The boost was largely explained by speakers feeling freer in expressing and exploring their views.
• Skillful listening can function as a psychological stabilizer in difficult conversations (Reis, Clark, & Holmes, 2004). Perceived responsiveness is a core mechanism of feeling understood, validated, and cared for. Authors propose that intimacy grows primarily from perceived partner responsiveness: the feeling that someone truly understands, values, and cares for core aspects of who we are. Perception fosters closeness and well-being because it makes people feel accepted and safe in revealing themselves.
• Active listening increases conversational satisfaction and perceived understanding (Weger Jr. et al., 2014). This study experimentally compared active listening to other response styles and found that active listening made people feel more understood than other strategies. Although advice-giving and active listening led to similar levels of liking and enjoyment, both were better than minimal acknowledgements.
• High-quality listening lowers prejudice (Itzchakov et al., 2020). High-quality listening predicts lower prejudiced attitudes via increased self-insight. Experiencing attentive listening led speakers to develop greater self-insight during conversations about prejudice, which in turn predicted reductions in their prejudiced attitudes. Being truly heard can reshape not only what people choose to share, but also how they reflect on and revise their own beliefs.
• You have to open up first to get people to open up to you (Dianiska et al., 2023). Open-ended and mutual self-disclosure rapport methods increase the amount of detail reported compared to closed-ended rapport. When interviewers used open-ended questions and shared a small amount about themselves to build rapport, teens provided longer and more detailed accounts than when interviewers relied on closed-ended questions.

Boundaries

I believe in boundaries. Join me in letting people self-select the level of disclosure they are comfortable with. I do not advocate for broad and unhindered interrogation of your team. I also do not recommend asking continuous follow-ups to people who aren’t interested in disclosing aspects of themselves.

This is similar to the article I posted reviewing authentic leadership. For atypical leaders, requests for authenticity provoke unreasonable, and sometimes unsafe, disclosure. If you have someone who is eager to get the job done and doesn’t want to talk shop, don’t force it. This is like trying to gain friendship with Shadowheart in Baldur’s Gate 3. Respecting privacy is a cool thing to do.

Core Research Findings

Across all the references compiled here, the research converges on a few principles:

1. Questions are a tool for surfacing assumptions, not confirming them. Remember, our job is not to interrogate in search of the truth. We need to remember the blame cycle. If we promote openness, the truth will surface on its own.
2. Psychological safety determines answer quality (Edmondson, 1999). If people feel safe to do so, they will raise risks, concerns, and mistakes. Low psychological safety equals low-fidelity answers.
3. Specificity builds accountability without shame. If we are specific about our questions, we avoid abstract praise, weird character judgements, and generalized criticism. We encourage specific behaviors and defined, time-bound outcomes.
4. Structure protects dignity in high-stakes conversations. High-stakes conversations go smoother and easier when we apply coaching frameworks. Active listening is behavioral.

The core framework here is:

• Reflect

“So what I’m hearing is…”

“So you’re saying…”

• Summarize

“In summary, you think X, Y, and Z? And the core issue we need to solve is ABC?”

“Pulling this all together, you’re making an argument for X and you need me to do Y?”

• Validate

“Yep, that is a tough situation. I get why you’re here with me.”

“I can see how you’d feel like that given all the context.”

“If I was you, I’d feel the same way.”

• Clarify

“What did I get wrong there?”

“Is my understanding accurate?”

“And when you say ‘lack of support,’ what would you say is missing?”

“When you say they aren’t treating you well, what actions make you perceive that?”

Question Archives

Meeting Questions

From research on inclusive decision-making, inviting creativity, critical thinking, and psychological safety. (Brooks & John, 2018; Coleman, 2022; Edmondson, 1999; Brodrick, 2024)

• What would make this meeting a win for us?
• What are we deciding now, and what’s explicitly still open?
• Do we have everyone in the room needed to make the decision at hand? (Note: I like to postpone meetings until I have all stakeholders).
• What problem are we solving today, in one sentence?
• What facts do we already know, and what are we assuming?
• What’s the most important constraint we have to respect?
• Whose perspective could we be missing that would improve this decision?
• What would change our mind or update our view on this?
• Can you walk us through your reasoning and the trade-offs you see?
• Let me reflect what I’m hearing, what did I get right, and what did I miss?

1:1 Questions

From research on best practices for effective one-on-one meetings, coaching methodology, upward feedback, and humble inquiry. (Austin, 2016; Bungay Stanier, 2016; Schein, 2013; Scott, 2017; Edmondson, 1999)

• What would make this 1:1 most useful for you today?
• What are your top priorities this week, and which one feels most fragile?
• Where are you getting stuck, and what have you tried so far?
• What’s taking more time or energy than it should?
• What do you need from me to be successful over the next two weeks?
• Where do you want more autonomy, and where do you want more direction?
• What’s one risk you’re seeing that I might not be seeing?
• What feedback do you have for me as your manager right now?
• What would you like to be different by our next 1:1?

Email and Async Channel Questions

From research on question framing, clarity of intent, active listening, goal alignment, and virtual team effectiveness. (Brooks & John, 2018; Coleman, 2022; Gallo, 2024; Google re:Work, n.d.; CIPD, 2026; Brodrick, 2024)

• What outcome are you aiming for?
• How urgent is this, and what deadline are you working against?
• What context would be most helpful for me to understand first?
• What do you want from me: a decision, input, or simply awareness?
• What constraints should I assume (time, budget, policy, dependencies)?
• What options have you considered, and what are the trade-offs as you see them?
• If I summarize my understanding as X, is that accurate?
• Who else should be looped in, and who just needs an FYI?
• What does “done” look like here, and how will we measure it?

Performance and Review Questions

From research on performance management guidance, developmental feedback frameworks, and critical thinking applied to goal setting. (CIPD, 2026; Center for Creative Leadership, 2025; Coleman, 2022; Austin, 2016)

• What accomplishments from this period are you most proud of, and why?
• Where did you create the most impact, and how do you know?
• What was harder than it needed to be, and what would have helped?
• Which strengths do you want to lean on more next cycle, and where?
• Which skill or behavior would most increase your effectiveness next cycle?
• What feedback patterns have you heard repeatedly, and what do you make of them?
• What goals feel most meaningful, and what trade-offs do they require?
• What support, resources, or clarity do you need from me to hit those goals?
• Looking ahead, what kind of work do you want more of, and less of?

Coaching and Transformation Questions

From research on structured coaching methodology, humble inquiry principles, and transformational leadership. (Bungay Stanier, 2016; Schein, 2013)

• What’s on your mind?
• And what else?
• What’s the real challenge here for you?
• What do you want?
• How can I help?
• If you’re saying yes to this, what are you saying no to?
• What was most useful for you?
• What would you try if you knew you couldn’t fail?
• What does a first small step look like in the next 48 hours?

Project Aligning Questions

From research on premortem methodology, team effectiveness, psychological safety, and structured critical thinking. (Klein, 2007; Google re:Work, n.d.; Edmondson, 1999; Coleman, 2022)

• What problem are we solving, and for whom?
• What does success look like, and what is explicitly out of scope?
• What are the biggest unknowns, and how will we test them early?
• Imagine it’s six months from now and this project failed: what are the most plausible reasons?
• What are the key dependencies, and who owns each one?
• What decisions must be made, and who is the DRI for each?
• What communication cadence will keep us aligned without creating noise?
• Where do you expect cross-team friction, and how should we handle it fast?
• What would make you lose confidence in this plan, and what would restore it?

Retrospective and Continuous Improvement Questions

From research including the U.S. Army After Action Review framework and learning acceleration methods. (U.S. Department of the Army, 2021; Klein, 2007)

• What was supposed to happen?
• What actually happened?
• Why was there a difference?
• What should we sustain next time?
• What should we change or improve next time?
• What signals did we miss or discount, and why?
• Where did we get lucky, and how do we make that repeatable?
• What’s the most valuable learning here, and how will we bake it into the process?
• What’s one experiment we’ll run next cycle to reduce risk or increase speed?

Difficult Conversations and Trust Repair Questions

From research on psychological safety, active listening, humble inquiry, and intent versus impact feedback models. (Edmondson, 1999; Gallo, 2024; Schein, 2013; Center for Creative Leadership, 2025)

• Can we agree on the outcome we both want from this conversation?
• What feels most important for you to be understood about your perspective?
• What do you think I might be misunderstanding right now?
• When did this start feeling hard, and what was happening around that time?
• What do you need from me in this moment: a fix, support, or simply to be heard?
• When X happened, I observed Y, and the impact was Z. What was your intent?
• What would make it easier or safer to raise concerns earlier next time?
• What would repairing trust look like in specific behaviors on both sides?
• What follow-up would feel fair, and how will we know things are improving?

Setting Expectations With a Low Performer

From evidence-based guidance on performance management, clarifying expectations, and behavior-specific feedback conversations. (CIPD, 2026; Fernandez, 2024; Gentry, 2025; Segal, 2016)

• What does “meeting expectations” look like in this role over the next 2–4 weeks, in specific, observable terms?
• When you look at the expectations, what feels hardest to execute consistently, and why?
• In a recent situation, I observed a behavior. What was your intent, and what got in the way?
• What support would make the biggest difference right now: clearer priorities, skill-building, tools, time, or faster feedback?
• What improvement plan can we both commit to, and how will we review progress and adjust?

Asking About Your Performance

From research on active listening, psychological safety, and techniques for eliciting upward feedback. (Gallo, 2024; Brodrick, 2024; Edmondson, 1999; Scott et al., 2023; Schein, 2013)

• What’s one thing I should start doing that would help you do your best work?
• What’s one thing I should stop doing because it creates friction or slows you down?
• When have you seen me at my best as a leader, and what did I do that you want more of?
• Where do you want more clarity from me, and where do you want more autonomy from me?
• What feedback have you hesitated to share with me, and what would make it easier or safer to share?

Repairing Broken Trust

From research on rebuilding workplace trust, navigating difficult conversations, and listening in a way that restores reliability and psychological safety. (Lyons, 2025; Harvard Business School Online, n.d.; Stone, Patton, & Heen, 2010; Gallo, 2024; Edmondson, 1999)

• From your perspective, what moment or pattern caused trust to drop?
• What impact did that have on you and on the work?
• What would rebuilding trust look like in specific behaviors from me over the next few weeks?
• What do you need from me now: acknowledgement, apology, explanation, changed behavior, or a concrete plan?
• How should we handle it if something like this happens again so we catch it early?

Negotiating Scope and Boundaries

From research on interest-based negotiation and technical boundaries with practical guidance on saying “no” while preserving relationships. (Fisher, Ury, & Patton, 2011; Wilding, 2022; CIPD, 2026; Watkins, 2013)

• What outcome matters most here, and what constraints are truly fixed?
• If we can’t do everything, what would you cut first while still meeting the real need?
• If I say yes to this, what should I de-prioritize or pause so quality doesn’t drop?
• What does “done” mean, and what are the must-have acceptance criteria?
• What decision rights do I have, and when do you want checkpoints versus full autonomy?

Managing Up

From research and guidance about managing up, aligning with leaders, and building open information flow. (Rousmaniere, 2015; Wood, 2023; Schein, 2013; Gallo, 2024; Edmondson, 1999)

• What are your top priorities right now, and how do you define success for my role?
• How do you prefer updates: cadence, format, and level of detail?
• Which decisions do you want me to make independently, and which should I bring with options and a recommendation?
• What pressures or constraints are you balancing that would help me make better trade-offs?
• If I disagree or see risk, what’s the best way to raise it, and what evidence do you want?

Succession Planning Conversations

From research and guidance on promotion conversations, readiness framing, and succession planning. (Knight, 2018; Velasquez, 2023; Harrell, 2016; CIPD, 2026; Watkins, 2013)

• What kind of growth are you aiming for, and what’s motivating it now?
• What criteria does this organization use for promotion at that level, and where do you think you are today?
• What would be compelling evidence that you’re ready, and what examples can we build over the next 3–6 months?
• What stretch assignments or visibility would be the best proving ground for those criteria?
• If the answer is ‘not yet’ or ‘not now,’ what would make this feel transparent and fair, and what’s our plan from here?

Addressing Behavior Issues in a High Performer

From research and guidance about the organizational costs of toxic behavior and using intent-and-impact feedback to correct behavior. (Purushothaman & Stromberg, 2022; Housman & Minor, 2015; Cliffe, 2001; Gentry, 2025; CIPD, 2026)

• How do you think your working style is landing with teammates and partners right now?
• In a specific situation, I observed a behavior and the impact was noted. What was your intent?
• What do you need to deliver results without negative spillover on the team?
• What specific agreements can we make about collaboration and communication going forward?
• How will we measure improvement in both results and behaviors, and when should we review progress?

Mediating Conflict Between Two Team Members

From research-informed conflict typologies, mediation techniques, and active listening practices. (Peterson et al., 2024; PON Staff, 2025; Brodrick, 2024; Gallo, 2024; Patterson et al., 2021)

• What is each of you trying to accomplish, and where do your goals overlap?
• What assumptions are you making about the other person’s intent, and what facts do we have?
• What does each of you need to feel respected and able to do your work?
• What new working agreements would prevent this from recurring?
• What small experiment will you both try for the next two weeks, and how will we debrief it?

Change Management and Ambiguity

From research and guidance for leading through uncertainty and quickly getting aligned on priorities. (Peshkam, 2026; Edmondson, 1999; Watkins, 2013)

• What do we know for sure, what is changing, and what is still unknown?
• What outcome are we trying to achieve with this change, and how will we know it’s working?
• What risks or unintended consequences worry you most?
• What would help you move forward right now: context, clearer priorities, training, or decision-making authority?
• What feedback loop will we use to learn fast and adjust?

Compensation and Equity Conversations

From evidence-informed reward guidance and research on the effects of pay transparency. (CIPD, 2025; CIPD, 2024; Obloj & Zenger, 2023; Fisher, Ury, & Patton, 2011)

• When you say ‘fair pay,’ what comparison are you making, and what data would be most helpful?
• What aspects of your role have changed that you believe should be reflected in compensation?
• What about our pay-setting process is unclear, and what transparency would be most useful to you?
• What matters most to you right now: base, bonus, equity, flexibility, development, title, or something else?
• What next step can we agree on today, and how will we follow up?

Setting Personal Expectations in a New Role

From research-informed onboarding and transition practices. (Watkins, 2013; CIPD, 2026; Schein, 2013; Edmondson, 1999)

• What are the three outcomes you’ll judge my success on in the first 30, 60, and 90 days?
• Which stakeholders matter most, and what does each care about from this role?
• What are the unwritten rules here: what gets rewarded, what gets penalized, and what pitfalls should I avoid?
• Where do you want me to move fast and decide, and where do you want alignment first?
• How should we handle surprises: how do you want risks raised, and how often should we recalibrate priorities?

Questions for Saying “No” With Class

From practical guidance on declining work while preserving trust. (Wilding, 2022; Fisher, Ury, & Patton, 2011; Schein, 2013; CIPD, 2026)

• What problem are you trying to solve with this request?
• What’s the deadline, and what happens if it slips?
• Which part is the highest value we can deliver first, and what can be deferred?
• If I take this on, what should I stop or delay so we don’t create hidden overload?
• What alternative would work: different owner, reduced scope, or a different timeline?

Discussing Burnout and Personal Struggles

From guidance on burnout as an occupational phenomenon and support conversations. (WHO, 2019; Ferrazzi & Jimenez, 2022; Gallo, 2024; Brodrick, 2024; Edmondson, 1999)

• How are you holding up right now, and what’s taking the biggest toll?
• Which parts of your workload are most draining versus most energizing?
• What would make the next two weeks feel more sustainable: fewer priorities, clearer deadlines, more help, or time off?
• What support from me would help most: protecting focus time, removing blockers, or adjusting expectations?
• How would you like me to check in, and what early signs should we watch for that you’re overloaded?

Exit and Retention Conversations

From research-informed retention guidance that emphasizes proactive “stay” conversations. (Nawaz, 2022; Tupper & Ellis, 2022; Gallo, 2024; Edmondson, 1999)

• What makes you want to stay here, and what makes you question it?
• What would need to change for you to see a strong future here over the next year?
• What skills or experiences do you want next, and how could we build a path to them here?
• Where do you feel underused or overused, and what would you like to do more or less of?
• If you ever decided to leave, what would likely be the reason, and is there anything we could address now?

Calibrating Personal Autonomy

From research and guidance about delegation and building psychological safety. (Fisher, Amabile, & Pillemer, 2021; Johnson, 2025; Edmondson, 1999; Gallo, 2024; CIPD, 2026)

• For this work, what kind of support helps you most, and what starts to feel like micromanagement?
• What checkpoints would be valuable, and what decisions do you want to own end-to-end?
• What does ‘good’ look like for quality and pace, and how should we define success together?
• What signals should trigger you to escalate or ask for help?
• How can I support you in a way that increases your autonomy over time?

Culture and Value Misalignment

From research-informed approaches to ethical voice and values-based action. (Gallo, 2015; Gentile, 2010; Edmondson, 1999; PON Staff, 2025)

• Which company value or norm feels at risk in this situation, and what specifically makes you say that?
• What outcome are you hoping for: correction, transparency, learning, or escalation?
• What risks do you see in speaking up, and what support would make it safer?
• What options would align with our values while still meeting the business need?
• What would you like me to do next, and what documentation or channels should we use?

Call to Action

Be great. Ask questions. Listen like you mean it. I believe leadership writing needs to be actionable. If you have a need for a category of questions that I am missing in my research, please reach out and I would be happy to update this reference list for you.

The most important step is always the next one.

-Dan

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References

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