Curiosity Questions Library
Questions that shift you from judgment to discovery. The best question is one you genuinely want to know the answer to.
Invites the person to share their preferences rather than assuming you know what they need. Different generations have very different feedback expectations.
Instead of:
“You need to get better at this.”
Try:
“I've noticed X and I'm curious about your perspective on it.”
This is a key onboarding question that reveals both feedback and learning preferences in one question.
Opens the door for insight you may be missing about their process or perspective. Creates space for honest input.
Instead of:
“This is how we do things here.”
Try:
“Here is our approach—and the reasons behind it. What questions does it raise for you?”
Draws on their positive experiences and helps you understand what effective feedback looks like to them specifically.
Validates that concerns are legitimate and creates space for honest conversation. Change skepticism often comes from past experiences, not resistance.
Instead of:
“This is just how it is going to be.”
Try:
“Here is the direction we're heading. What questions or concerns do you have?”
Surfaces what they're protecting—often something that made sense 'on their planet.' Understanding this shifts you from judgment to curiosity.
Instead of:
“Why won't they just conform to how we do it here?”
Try:
“What assumptions might be different for them given when and how they grew up?”
Focuses on their needs rather than pushing compliance. Different generations need different supports for change.
Draws on their experience and shows respect for their history of navigating transitions. They've survived changes before.
Shows genuine curiosity and signals that you want to understand, not just be understood. A core 'visitor' question.
Instead of:
“You are being difficult about this.”
Try:
“We see this differently. Help me understand what matters most to you here.”
Moves from positions to interests and opens collaborative problem-solving. Fairness means different things to different generations.
Demonstrates humility and willingness to learn from the disagreement. Models the curiosity you want to receive.
Cuts to the core of their perspective and shows you genuinely want to understand their 'planet.'
Growth means different things to different people and generations. Some want ladder, some want lattice, some want skill depth.
Instead of:
“You need to pay your dues first.”
Try:
“Let's talk about what growth looks like from where you are now.”
Shows investment in their future and opens dialogue about development. Time-bounded makes it actionable.
Especially important for younger generations who often seek purpose and visible contribution to something meaningful.
Positions you as a partner in their success rather than a gatekeeper. Shows coaching mindset over evaluating mindset.
Different people need different types of support. This asks rather than assumes. Older hires may need context, younger may need structure.
Instead of:
“Just figure it out.”
Try:
“What questions do you have that you haven't felt comfortable asking?”
Uncovers gaps between expectations and reality that may be causing friction. Surprises reveal where your 'planet' differs from theirs.
Learning preferences vary by person and generation. Gen Z often prefers interactive and visual; older workers may prefer depth and documentation.
Invites them to contribute to improving the process while surfacing what's not working for them specifically.
Communication preferences vary dramatically: email vs. chat vs. video vs. meetings. Acknowledging this shows respect.
Instead of:
“Just send me an email.”
Try:
“How do you prefer we communicate on this? Let's find what works for both of us.”
Directly addresses one of the biggest generational friction points. Boomers often prefer email/meetings; Gen Z often prefers chat/video.
Shows respect for their working style and opens dialogue about team norms without assuming one way is right.
Identifies barriers you can help remove rather than assuming you know the problem. Often reveals generational blind spots.
A core 'visit another planet' question that reveals formative experiences. Economic conditions when someone started work shape lasting expectations.
Leadership expectations are deeply generational. Understanding their 'good boss' model helps you bridge to it.
Immediately undermines over-generalization and opens authentic conversation. Shows you see them as an individual.
Safety means different things based on formative experiences. Recession survivors, pandemic survivors, and those who saw layoffs have different needs.
Replaces 'When I was your age, we...' with genuine curiosity about their current reality. A powerful reframe.
Instead of:
“When I was your age, we...”
Try:
“What's the world like at your age right now?”
Remember: Your job is not to fix other planets, but to become a respectful visitor and guide. Lead with lived stories, then check them against the data.