230+ Impactful Questions for (Almost) Every Work Scenario

My Ever-Growing Master List of Questions for Both Sides of the Table

“The stupidity of people comes from having an answer for everything. The wisdom of the novel comes from having a question for everything.” Milan Kundera, The Book of Laughter and Forgetting

I believe in asking questions. In fact, it’s my most strongly held belief.

All good content, relationships, and solutions start with good questions. I am lucky to have discovered this early.

As a five year-old, my favorite game to play was the question-asking game. I would ask my Mom to ask me questions on rides to school, and then I would ask those same questions in return. 

Over time I accumulated so much information about her that twenty years later I can complete virtually any of her sentences.

When I made it to college, question-asking helped me finish dozens of enormous papers on time. I would structure outlines as questions, rather than definitive answers.

The search for those answers would surface new probing questions that would change the directions of the papers, while still keeping me focused. This process always led towards a deeper understanding of my subject, giving the work a clear purpose without limiting me.

Cut to now, and I have conducted over 300 interviews as a journalist and writer, and close to that number on both sides of the hiring process.

I have collected questions along the way to help me sharpen my craft. Some of them are mine; many come from great leaders, interviewers, and innovators like Tim Ferriss, Gary Vaynerchuck, Debbie Millman, Seth Godin, and many others.

I am excited to share my collection — as well as advice for using it — with you.

My Framework for Asking “Good Questions”

Good questions are made up of more than carefully chosen words. They are stirring conversation-starters that help spark discussion, uncover truth, and establish relationships.

Words can help achieve these bigger goals, but ultimately what makes them successful is why they are asked, how they are asked (both sequentially and in their delivery), and who is answering them.

In Kevin Kelly’s The Inevitable, he shares a comprehensive definition of a good question, which among other things, “is not concerned with a correct answer, cannot be answered immediately, challenges existing answers, is one you badly want answered once you hear it, but had no inkling you cared before it was asked” and is a “probe, a what-if scenario” that “skirts on the edge of what is known and not known” and “cannot be predicted.”

While Kevin Kelly focuses on the question itself, Tim Ferriss thinks about the sequencing of questions. In Tribe of Mentors, he suggests that the order in which questions are asked is just as important as the questions themselves. Starting with easier questions helps the answerer respond with more confidence and think more deeply, leading to better answers.

In my experience, the best questions can be used over and over, so long as they are contextualized, personalized, and recombined according to the answerer’s unique experiences and relationship to you.

1. Contextualization

A good question starts with a motivation, which is then contextualized for the answerer. Before I ask my question, I explain why the answer is relevant.

For example, my motivation during an interview with a startup founder may be to give my audience a high-level understanding of the industry that founder is disrupting. To contextualize my question, I will share who my readers are and why understanding the industry or market conditions is important to them. I may even take it as far as sharing with that founder why providing this information will drive personal, professional, or even company-wide benefits.

Context applies not only to what information you give before a question, but also to how the question is constructed.

The best questions only ask one question at a time.

I struggle with this practice all the time. However, your question contains the context, so the more you add in, the more you muddle. Ask more than one question at a time and you risk not getting anything answered and confusing the answerer.

2. Personalization

Questions should also feel personalized — unique to the individual answerer. You may ask every friend, mentor, and colleague the same question, but it shouldn’t feel like a stock question.

An easy way to make questions feel personalized is to change a question like “What do you value most?” to “What do you value most, Kevin?” Directly addressing your answerer draws in their focus and makes them feel like you are fully present.

Bringing in anecdotal information or tying the question back to the conversation also makes it feel more personalized.

Instead of pivoting into “What do you value most and why?” without any build up, try integrating the question into a natural flow. Otherwise, you will come off as if you’re reading from a list, which will result in much more mechanical, surface-level answers.

“Kevin, it’s so interesting that you still remember how hard your high school basketball coach was on you. It seems like even though it hurt you then, his feedback really helped you push yourself to be a better founder today. Would you say radical honestly is one of the things you value most? What else do you really value?”

In this situation, Kevin now has an anecdote to help anchor him in the question. He can reflect on the experience and extract answers if they aren’t readily available, and he should feel like you are in a meaningful conversation centered on him.

3. Recombination

Finally, the way you recombine questions can lead to strikingly different results, as well as make conversations more natural.

Reading from a list of questions is fine so long as you give yourself room to change their delivery, reorder them, and spread them out.

Before you start asking questions, write five to seven of them down with the goal of only asking three to four during your conversation. This will help you frame out what you want to learn and what direction the conversation will go in, while also giving you a base of questions to use as the answerer reveals more.

Don’t focus on asking the questions perfectly in order, but on using them as stepping stones, transition points, or probes.

This may seem more applicable to formal interviews, but it works in every situation. If you plan on having a meaningful conversation with a friend or partner, thinking about what you’d like to know or connect about before will help you unearth things you never knew and establish a deeper bond.

The Golden Rule

With questions, there are frameworks, processes, and models to use, but for the most part, there are no formal rules.

Kara Swisher of Recode is known for asking boundary-pushing questions that seem like bona fide rule-breakers. She asks people who are dying why and how, powerful people how they are bringing their companies down, and the brightest minds why they make stupid mistakes. And all the while, she is respected as a journalist and interviewer.

Still, there is one informal rule every question-asker should live by: be curious.

Curiosity should spur you to ask more questions, lean into uncomfortable truths, and even get closer to understanding yourself. 

Don’t be afraid to let curiosity lead you away from a rigid path, so long as you know why you want to stray.

A Note About Favorite Questions

This is my last interlude before I get into my very long list of questions.

I have taken care to bold the questions I find most useful, link back to original askers for more ideas and backgrounds, and eliminate questions that seem repetitive.

I hope you will go through this list and find new favorite questions to try in every situation. My own favorites are the first two questions on the list:

· What questions do you ask yourself on a regular basis?

· What didn’t I ask that I should have?

In addition to serving as my favorite questions, these two also double as questions to you.

I am giving you my master list of questions in the hope that we can grow and refine it together. I hope it is as useful to you as it has been to me.

General

For multi-purpose use across categories

· What questions do you ask yourself on a regular basis?

· What didn’t I ask that I should have?

· What do you value most and why?

· What are your non-negotiable values?

· What would failing on your own terms mean to you?

· What happened today? (Larry King)

· If you could move to a place where history is being made right now, where would you go? (Craig Wortmann)

· What evidence can you offer that you can really make the story come true? (Craig Wortmann)

· What do people never ask you that you wish you did? (Tim Ferriss, The Tim Ferriss Show)

· What is something true that almost nobody agrees with you on? (Tim Ferriss, The Tim Ferriss Show)

· What would this look like if it were easy? (Tim Ferriss)

Leadership

For cultivating one’s own development, as well as the development of others

Self-Reflection

· Are my goals my own or what others expect from me?

· What does achievement feel like to me?

· What am I most afraid of losing? Of gaining?

· Who is leading better than I am and why?

· If I could assemble an all-star team of top-performing leaders to guide me, who would I choose? Why?

· Is what I’m doing moving me toward the things that most matter to me? (Carolyn Coughlin, “Cultivating Leadership”)

· What do I feel and what’s possible for me as a result of being able to own my feelings? (Carolyn Coughlin, “Cultivating Leadership”)

· In the last five years, what new belief, behavior, or habit has most improved my life? (Tim Ferriss, Tribe of Mentors)

· How much of life have I missed from underplanning or overplanning? (Tim Ferriss, Tribe of Mentors)

Developing Talent

· What are the three things you need in work to achieve purpose? What can I do to help you get them?

· Who do you aspire to be as a person?

· What do you aspire to do as a person?

· What is holding you back?

· What is pushing you forward?

· How do you celebrate your victories?

· What does leadership mean to you?

· What are you doing that’s difficult? (Seth Godin)

· What size company do you imagine working for? (Russ Laraway)

· What industry do you want to be in? (Russ Laraway)

· Do you want to be in a very senior individual contributor type role or very senior management type role? (Russ Laraway)

· Do you have what you need to invest in your people with the same focus and fervor you want them to give your company? (Russ Laraway)

Firing

· Do I trust this person?

· Could this person change my mind about termination? What would this person have to do?

· Does the blame lie with this person, or with processes, technologies, or some other non-human factor?

· Am I clear this person’s poor performance is affecting the rest of the team? (Kim Scott, Radical Candor)

· Who can I speak with who will listen carefully as I talk through what I need to do? (Kim Scott, Radical Candor)

· Am I certain I have given radically candid guidance? Have I shown this employee that I care personally about her work and life and that I have been crystal clear about challenging her to improve? (Kim Scott, Radical Candor)

Entrepreneurship

For deciding whether to start a business, what business to start, and how to fund it

Jumping In

· What is the worst that could happen?

· What is the best that could happen?

· What does the end look like? Are you happy with that end?

· Are you willing to put your own skin in the game?

· What is one of the best or most worthwhile investments you’ve ever made? Could be an investment of money, time, energy, etc. (Tim Ferriss, Tribe of Mentors)

· Does going after this dream make you feel like you’re making progress? Like you’re growing? Like you’re moving forward? (Danielle LaPorte)

· What is the smallest action you could take today to have the biggest impact? (Craig Wortmann)

Ideation

· What problem do you encounter every day that you could solve with technology?

· What would you pay for right now that you can’t find?

· If you failed at solving this problem, would it be painful enough that you would help a competitor do it?

· Do the people who experience this problem have the power to make decisions?

· How many other people experience this problem?

· Will this market exist in 6 months?

· Will this problem matter in 5 years?

· Do you care enough about this idea that you would be willing to build your life around it?

· What are you willing to give up to fix this problem?

· What do you spend a silly amount of money on? How might you scratch your own itch? (Tim Ferriss)

· If you could only work 2 hours per week on your business, what would you do? (Tim Ferriss)

Fundraising

· What matters to you more: money or control?

· Are there other ways for you to finance your company?

· If you can’t raise outside investment, what will happen?

· Have you found product-market fit?

· Who are your power users and are they enough to grow your company?

· What does your growth trajectory look like?

· What patterns in the market apply to your company, good or bad?

· Can you hit the expected milestones to earn your next round of capital?

· Why wouldn’t you take outside investment?

· Are you building a company that will produce a 10x return for investors?

· How much capital do you need to grow in the next 12 to 24 months?

· What will your investors bring to the table beyond monetary investment?

· Do you want to work with these investors for the next 8 to 10 years?

By Specialization or Function

For generating ideas, refining processes, and creating change within a specialization, function, department, etc.

General

· Before I start, what is my desired outcome?

· What is the “best” advice I should ignore?

· What shouldn’t I do?

· What are bad recommendations in this area? How do I avoid them?

· Does this path clearly create more opportunities?

· Does saying no to things so you can pursue this goal ultimately make you feel lighter? (Danielle LaPorte)

· Is this going to help me get the results that I’m aiming for? (Danielle LaPorte)

Branding and Content Development

· What can you be best or second best at?

· What are you known for? Is it good or bad?

· Why do you want to change?

· Why don’t you want to change?

· If resources were not a limitation, what would be the first thing you would change?

· How strong is your reputation among your key stakeholders?

· What do you want your audience to feel?

· How can you make your audience feel “special”?

· What are the brand’s core values?

· Do your messages align with the values?

· What unique insights or data do you have to share?

· What questions do your stakeholders have that you have the answers to?

· What questions do you have that others could answer for you?

Engineering

· What can you automate?

· What shouldn’t you automate?

· What new technologies do you need to prepare for?

· What do you need to learn to prepare for the future?

· Where are you understaffed? Overstaffed?

· Why would your systems fail?

· What measures have you put in place to prevent failure?

· Which engineers do you admire? What are they doing differently?

· Which engineering teams do you admire? What are they doing differently?

· If resources were not a limitation, what would you change?

Selling (Improving Sales)

· Who is your current best customer? What makes them the “best”?

· Who is your ideal customer?

· What is your ideal customer profile?

· Why would you buy the competitor’s solution?

· Why would your customers leave?

· Which sales teams do you admire? What are they doing right?

· Who is the best salesperson you know? What differentiates this person?

Selling (Qualifying and Closing Leads)

· What does success look like for you?

· What does failure look like for you?

· What about your current solution isn’t working? How does that impact you personally?

· If you could focus more resources on one problem your company is facing, what would it be? (Craig Wortmann)

· What one or two metrics are the most important — ones you track religiously? Why? (Craig Wortmann)

· If you were able to make this happen, what would it mean for you personally? (Craig Wortmann)

Hiring

For determining whether to add roles, how to create them, and how to hire for them

Before Hiring

· Where is there scarcity?

· Is this scarcity working for you or against you?

· Where is there surplus?

· Can the surplus and scarcity be balanced with lateral moves or reorganization?

· Do these roles and responsibilities amount to a full role?

· Is there room to grow new people?

· Do you have the resources to run a successful search?

· If you couldn’t add this role, what would you do? What other options exist?

· Why are you adding this role? (Jennifer Rettig)

· What direction do you hope this role will take the company? (Jennifer Rettig)

· How will the person in this role interact with existing leadership? (Jennifer Rettig)

General Interviewing

· Why us?

· Why not you?

· If you had a magic wand and could transform this role into anything in the world, what would it be?

· What is your life story up until today?

· If you had to boil down your life story to one word or theme, what would it be?

· What is your work philosophy?

· What do you value most in work?

· What do you want most in work?

· What don’t you want in work?

· What do you dislike most in work?

· When did you fail hardest and why?

· What experience do you regret most until now?

· Who are your role models and how do you model yourself after them?

· What is your life philosophy?

· If you were offered this job on the spot, what one factor would make you turn it down?

· What do you want to be when you grow up? (Gary Vaynerchuk)

· Why are you leaving your current job? (Jack Welch)

· What would someone who doesn’t like you say about you? (General Stanley McChrystal)

· What do people say when they talk about you? (Seth Godin)

· What is a childhood dream you knew you would never realize? (Tim Urban, Tribe of Mentors)

Interviewing Prospective Candidates for Curiosity

· What is the hardest skill you ever taught yourself and why did you do it?

· How would you teach me something new right now?

· If we were in a library, which section would you gravitate to and why?

· What is your life motto?

· How do you react when team members challenge your ideas?

· How have you contributed to your own personal development?

· If you could uncover any single fact about my company, what would it be?

· What is something you could genuinely give a TED Talk about? Give me the 2-minute version.

*These questions were previously featured in Here’s Why Soft Skills Are More Important Than Technical Skills.

Interviewing Prospective Candidates for Emotional Intelligence

· Describe yourself in three words. Why did you choose them?

· What are your core desired feelings?

· How do you build bridges?

· When do you tear bridges down?

· What do you protect most intensely in your life?

· How do you say no to team members?

· What is your style of delivering feedback?

· What type of feedback helps you grow?

· What are the core values that guide your life?

· What are the core values that guide your work?

· What energizes you?

· What drains you?

· What, if anything, is too serious to be joked about? (Arthur Aron)

· For what in your life do you feel most grateful? (Arthur Aron)

· How is what you think is right informed by, but not the same as, what others say is right? (Carolyn Coughlin, “Cultivating Leadership”)

Interviewing Prospective Candidates for Expertise

· Who in our industry do you think is leading the way? How can we learn from that company or person?

· What is the biggest problem our industry is facing today? How would you fix it?

· What is the biggest opportunity our industry is facing today? How would you seize it?

· What ideas do you have to transform this organization?

· What is a “bad idea” you think could bring this organization to the next level?

· What are we doing right?

· What are we doing wrong?

· How would you solve this problem with your specific skills?

· How would you fix this problem with a specific technology platform or solution?

· How would you fix this problem with a new process?

· What tools or resources would you need to create business value for the company?

Interviewing for Jobs

For determining what jobs to pursue, how to get them, and how to determine if they are a match for you

Career Planning

· What do I want in work?

· What am I not willing to give up? Could be location, money, hours, autonomy, etc.

· What am I willing to give up? Could be location, money, hours, autonomy, etc.

· What career would I be proud to tell my grandchildren about?

· Which leaders embody the values I aspire to represent? Are they hiring?

· Which companies embody the values I aspire to represent? Are they hiring?

· Who could help me find my dream job?

· Who could I meet with to learn more about the companies I want to work for?

· Do I know people who have left the companies I want to work with? Why did they leave?

· Do I know people who have stayed at the companies I want to work with? Why did they stay?

· How am I getting in my own way?

· Am I spending enough time on looking for, finding, and working toward winning a great job? (Debbie Millman, Tribe of Mentors)

· Am I constantly refining and improving my skills? What can I continue to get better and more competitive at? (Debbie Millman, Tribe of Mentors)

· What are the people who are competing with me doing that I am not doing? (Debbie Millman, Tribe of Mentors)

Interviewing Prospective Employers for Business Health

· What is the future of this company? What do you envision it will look like in three years versus today?

· What’s holding your company back from reaching its goals?

· How do you measure success? What are you tracking on that scale now?

· How do you measure individual success? Do you have performance metrics in place?

· What is the biggest business win you’ve had this year?

· What is the biggest departmental win you’ve had this year?

· When has the company fallen short or missed a milestone? What happened?

· If the company were to unexpectedly close, what do you predict the source would be?

· What challenges do you foresee in the future?

· What opportunities do you foresee in the future?

· What characterizes your best customer?

· Who are your customers and what is their buying behavior?

· Who are your raving fans?

· Who drives decisions at this company?

· Who is the company accountable to?

· Who is your competition?

· Who are your investors and what value do they bring?

· How do you view the competition? What are they doing well?

· What are you doing that people believe only you can do? (Seth Godin)

· Would we miss your work if you stopped making it? (Seth Godin)

Interviewing Prospective Employers for Culture

· What kind of people succeed here?

· What are the CEO’s defining personality traits?

· How does leadership work together?

· When do people go home?

· When do people come in?

· How long do people stay here? Why do they stay?

· When people leave, what reasons do they give?

· From a culture standpoint, what could you improve?

· Are there opportunities for employees to improve culture? How have they done so in the past?

· When things go wrong, what do you do?

· Can you give me an example of a time an employee went through a hard time and the team rallied around them?

· What quirky or unusual practice is the company known for?

· Do employees become friends with one another? How does the company view office friendships?

· How do you build teams? Who decides on the composition of those teams?

· How do you promote diversity of thought and opinion?

· How do you promote diversity of background and experience?

· What characterizes the best employee you have ever had? What did they do differently?

· What do you stand for? (Seth Godin)

Parting Words

This list of questions, though long, is by no means complete. There are so many more questions to be asked in so many different contexts, configurations, and frames.

That’s why I want to know what questions you ask. Share them in the responses, and they may get added into this list!