By Ondrej David in advice — 22 Jul 2025

Talking to People

Collection of questions and revelations on how to talk to anyone you'd like to work with.

My ever-growing list of lessons in what works and doesn't work when talking to people. Lessons and concrete questions I like to remember and share with all that ask. Whether it's an interview for a job you are conducting or partaking on either side. Whether it's a conversation you are to have with a new collaborator or a co-founder. Whether it's just a date in a newly begat relationship. I've always found the separation of professional and personal overly absent of the reality: we are all just people talking to other people.

Lessons

Tell a story.

People exchange stories. People remember other people for the stories. Think to yourself and your closest friends and family. You remember them for the experiences you've had together, not (just for) who they are. Through the stories you gather attention to express who you are, what is it that you are talking about, without ever having to go through the background story, or reciting a listicle.

You are on a clock.

Unless you are the evening attraction assume that your audience is riddled with impatience. They want to be on their phone, watching a movie, reading that book they've been neglecting for so long, go back to their project or work. When someone makes the time for you, appreciate every second of it and give back the most you can as fast as you can.

Hook the listener in.

Your story can be well said, but still boring. Know your audience and take your best bet at what will grasp their attention and strengthen the story. Boring stories leave people disappointed and never wanting to listen to you. Start with understanding the point of your story and how to get to it really quickly. Then work backwards with details in a linear arc of beginning and an end, hero overcoming obstacles, and whatever else fits the occasion.

Leave them wanting more.

Once you learn to tell when someone is hooked, leave them wanting more. This is especially useful in negotiations where you are sure of your power. Just as well in courtship and makes up large portion of the flirtation.

Be concrete and avoid platitudes.

This is the best tell how much lived versus book experience someone has and how well they were able to synthesize the two by answering your questions with practical answers. Anyone sounds wise when repeating the wisdom of the old (and there's truth in it). Use the platitude as a hook followed by a specific example from your life and relate it to how it applies to the conversation.

Put people on the defense.

People under pressure tend to stand up for their ideals. Play the devil's advocate to see how they react to someone you personally think is outrages and see where it takes the conversation. Be mindful of play: people can get hurt, so try to keep the damage to the minimum. In reverse situation be ready to be put on defense by others. Know what you stand for, your principles and especially when to have an emotional and when an intellectual response.

People lie.

Everyone lies. To themselves, to you, and to others. Some by intention, and some by laziness, some to help others. Most lie to get what they want, to be interesting, to exaggerate, and to avoid uncomfortable situations. Choose your own lies carefully and be aware of them. When others speak your lies you'll be able to spot them. Learn what others lie about by digging deep, instead of wide. The softer the skills and more trust you are willing to put in and reliance you are looking to have the harder the search and harder should be your questions.

Skills are hard to assess without the skills.

Say your water pump breaks and you know nothing about how it works. When you call in the water pump guy he tells you a story, quotes you an amount and puts you a mercy of trusting him. In this conundrum you are unable to assess whether you should blindly trust this man. Same goes for doctors, taxi drivers, pilots who we rely on with our lives. Don't trust blindly (as people lie) and gain the basic understanding of the solution first - ask and put the people on the defense to win your trust.

Interviews are not one-size fits all.

Some people have hard time interviewing, just as much as they have hard time talking to people. Maybe their work and other people can speak for them better than they can for themselves. Where the output of the work matters more than what they have to say look at the work.

Questions

Talking to Anyone

What do you like to do?
What do you not like to do?
Tell me something that's truth that nobody agrees with you on.
What was the last thing you learned about yourself? > How did this learning came to you? > How do you apply this in your life?
What are you afraid off when you join a new social/work group?
What makes you come to work?
What is easy?
What challenges you?
How do you learn?
What are you most proud of in your life? > How about in your career?
What has been your biggest loss? > What was your biggest failure? > What is the biggest failure you have been a part of?
What kinds of people do you want to meet right now? > What's something you want to receive from the group? > And, what's something you can give to the group? > If you could meet anyone you wanted to who would it be?
What problems interest you? > What problems are you looking to solve? > In here (were we to hire you)? > In your life?
What problems do you have?
What do you want to have happen to the business? (Useful for executive hires.)
What has been a meaningful thing that happened to you in the past year?

Talking to Co-Founder

Setting up expectations with people you'll have to be tight like criminals in a shared cell.

Why do you want to do this startup?
What are your personal goals here, both financial and non-financial?
What are your long-term goals in life?
What is your overall life plan and how does this startup fit into it?
Are there pressures in your life that you’re dealing with now?
Who would you pick to start the company with if you could pick anyone in the world?
What makes you most excited about working with me?
What makes you concerned about working with me?
What’s the best way for me to give you feedback?
When you feel stressed, do you tend to want to talk about what’s going on or avoid talking about it?
What environment do you work best in?
What can we do to help you create it?
How will we divide responsibilities?
Who will be CEO?
What will our roles and titles be?
We should have a plan for what you’ll each work on for the first 6-12 months.
How will we split up equity?
Where will the company be based?
Where will we each live?
Will we work together in-person or remotely?
How do we pick the idea to work on? > If that idea doesn’t work out, are you willing to change the idea?
Are you only interested in working on ideas in certain areas?
What needs to happen for each of us to go full-time (quit other jobs or school commitments)? ie: We’d have to raise at least $xx from investors, we’d need to validate the idea with a paying customer
What is your personal financial situation? > Are you willing to work for free and live on your savings? > For how long?
If you'll need a salary to work on this full-time (either now or at some point), how much do you need to feel comfortable?
Will either of us put money into the company?
What will our typical working schedule be?
Are there any things outside of work that are important to you to make time for?
What is important to you when building a team? > building an in-person vs remote company > having certain cultural values > having a particular approach to hiring or managing people
What will we do if we’re having trouble agreeing on an important decision? > What will happen if we decide we don’t want to work together anymore?
How would your friends or colleagues describe your strengths and weaknesses? > Do reference calls on each other. / Meet in person > Do a trial project > Meet friends / partner
What are you proud of having accomplished (can be work-related or not)?
What do you do with your free time? > What are your hobbies and interests? One of the surprising things about successful co-founders is how consistently they have overlapping outside-of-work interests.
What are companies, founders, or products you really admire? > Are there any you want to model this company after?
What were your experiences like at your past jobs or past startups? > What did you like and not like about how the companies were run? > What lessons did you take away? > Have you worked with a co-founder previously? What was that experience like?
How have your experiences shaped your values?
What kind of work is so fun for you it doesn’t feel like work?
What kind of work do you avoid doing?

Talking about Other People

When doing due diligence. Apply before starting a business relationship. The higher the position, the more trust you need to have.

How does this person compare to the best you’ve ever seen in the role?
What is something that [candidate] is better at than anyone else you've worked with in this role
How many people have you worked with in [candidate’s] role/level?
How would you rank [candidate] among their peers?
What is something that [candidate] is better at than anyone else you've worked with in this role?
What type of advice would you go to [candidate] for?
On a scale of 1 - 5 (where 5 is absolutely perfect), how would you rank this person? > how do you rate XYZ on [specific trait or ability]? > What is the reason you did not rate XYZ (insert a number that is 1-2 points higher/lower)?
Can you tell me about a project that would have failed without [candidate]?
What is your most memorable experience working with this candidate? > How about when not working? > Tell me something about CANDIDATE that might not be listed on their resume or LinkedIn.
Would you rehire this person? (Look for enthusiasm when they talk about the candidate more than the answer itself.) > Would you rehire them for the same role? For a different role?
Would you invest your own personal money in this person? Why or why not?
What was the context of why you stopped working together?
Can you share an experience where [candidate] really blew your mind?
What is the candidate’s superpower?
What was an experience where you saw the candidate grow? > What might still be the candidate's growth areas? > If you were to design an ideal role for this person, what would it be?
Do you have any examples of times when the candidate demonstrated grit? Not giving up?
Explain the role at length and what success looks like in the first year. > Do you think that [candidate] will thrive in that position?
Tell me about a time when you saw this leader build a new team. > They said they did it at the company. Can you tell me what you observed? > What was something unique about this candidate's team versus other teams?
Does [candidate] thrive as a team player or a lone wolf?
In which kinds of projects or work is [candidate] most effective? > Which situations are more challenging? / What causes the candidate stress or friction?
What environments do they thrive in, and where would they be less effective?
What "special treatment" helps [candidate] do their best work?
Can you tell me about a time that the candidate missed a deadline?
How does the candidate deal with giving and receiving criticism?
How does this person deal with differences in opinion?
Can you share someone who maybe doesn’t necessarily get along with [candidate] as well as you do? Why do you think they don’t mesh well?
What was [candidate’s] reputation within the organization or department? > Among customers?
How do you think I can best support this person to make sure they thrive here? > How do you build trust with this person? > How would I know when [candidate] is unhappy?
What motivates this candidate?

Talking about Real Estate

Finding a new place to live. Renting or buying, you want to ask a few questions of the owner or the current tenants.

Why are you moving out?
How noisy does it get around here?
What is and what isn't included in the price? > Utilities, which utilities > Application fees, move in fees
Any plans for construction?
What's the neighborhood like?
What policies do you have? > Guest / Subleasing / Thrash / Smoking / Pet
How do I pay you?

References

My lessons and questions come from all kinds of places. I do my best to keep a running list here.