How To Ask Better Questions (Especially When You Sell, Negotiate, Network, and More)

Plus 40 of my Favorite Questions You Can Use Today To Grow Your Business, Expand Your Network, and Deepen Pre-Existing Relationships

When is the last time you asked yourself (or was asked) an important question like…

  • What do you want to be when you grow up?

  • Will you go on a date with me?

  • Will you marry me?

  • Do aliens exist?

  • What will people say about me at my funeral?

I’ve had my fair share of life-changing moments as a result of asking big questions.

At 16, I asked “The Most Connected Man You Don’t Know In Silicon Valley” according to Forbes for an internship via cold email and learned over two years (going from intern to early employee of a VC-backed startup currently valued at $100M+) about marketing, outbound sales, how high-performing teams build winning cultures, how challenging it is to start and scale a successful business, and much more.

At 17, I asked Forbes 30 Under 30 honoree and serial entrepreneur Stacey Ferreira to co-author 2 Billion Under 20 with me, and we went on to sign a publishing deal with a major New York firm and write the #1 Entrepreneurship Book of 2015.

And last year, I asked my best friend to marry me. She said yes! 😁

The right questions can change your life forever.

As entrepreneurs, we can benefit immediately from asking better questions.

In sales, depending on how expensive your products/services are and how much you need to “qualify” clients in advance of working with them, you’ll likely take Discovery Calls to assess the Budget, Need, Urgency, and Authority (BNUA) of an interested lead.

When screening applicants for Meeting of the Minds, for example, we ask:

  • Why do you do what you do?

  • What are your top business and personal goals over the next 12 months?

  • What do you consider yourself a subject matter expert in? Or how would you describe your Zone of Genius?

  • How would you describe an Ideal Client for you?

  • What's going well right now?

  • What’s holding you back from accomplishing your goals at the moment?

  • What decisions, projects, or upcoming meetings are keeping you up at night?

  • How are you currently trying to capitalize on your exciting opportunities and/or solve your pressing problems?

Asking the right questions can also help you in negotiations.

In the back of his bestselling book Never Split The Difference, former FBI hostage negotiator Chris Voss has a “Cheat Sheet” I’d recommend you bookmark so that you can review it next time you’re negotiating a new hire’s salary, trying to lower vendor costs, or otherwise tilt the odds in your favor during tense collaborations.

Below, I’ve included some sample questions from that resource which you can use to unlock valuable information from the other side of table during negotiations.

👉 Never Split The Difference “Cheat Sheet” 👈

  • What do you need to make this work?

  • How can we solve the problem?

  • What about this doesn’t work for you?

  • How would you like me to proceed?

  • (If someone is difficult to reach…)

    • Is now a bad time to talk?

    • Have you given up on this project/team/collaboration?

  • (If someone isn’t budging from their stance and/or is asking you to over-pay…)

    • What about this doesn’t work for you?

    • How am I supposed to do that?

    • What happens if you do nothing?

Open-ended questions can help you build deep, meaningful connections with friends new and old.

We start most Meeting of the Minds experiences with a series of icebreakers designed to reveal something exciting and/or intimate about your fellow entrepreneurs.

Back in 2014, Steve Dean (founder of Dateworking and frequent co-host of dinners and networking events with me when I lived in New York City) published a 100+ question Medium post I’ve shared below, along with select prompts I’ve plucked out for you that are great for learning more about your colleagues, friends, and family.

From “Questions to Spark Authenticity” on Medium:

  • What is a belief you would be willing to die for?

  • What would be the most difficult decision you’ve ever made?

  • What worries you most about the future?

  • What are you holding onto that you need to let go of?

  • What is your self-talk like?

  • What is the biggest mistake you have ever made?

  • What’s the number one change you need to make in your life in the next twelve months?

  • When was a time where you took someone for granted and you wish you hadn’t?

  • In what way are you stronger than you look?

  • What do people thank you for most often?

  • What is the best piece of advice you’ve ever gotten?

  • In what way are you above average?

  • If you had $100 million in the bank, what would your day look like?

  • What are you dealing with right now?

  • What is one thing that is unique and true about you?

  • What is the biggest risk you have ever taken in your life?

  • What is something interesting about you that almost no one knows?

  • What are you most proud of yourself for?

  • What is your back-up plan if the unthinkable happens?

  • What is the nicest thing you have done for a complete stranger?

  • Where are you playing small in your life right now?

  • What is something where you have a hard time asking for help?

  • What are you doing when you feel most alive?

Learning from the best…

To delve deeper into the psychology of interviewing, asking “big questions”, and connecting with someone regardless of their background, industry, or intentions, who better to learn from on this topic than New York Times bestselling author, former Editor-At-Large for Esquire, and keynote speaker Cal Fussman.

On set with Cal Fussman and Emmy award-winning journalist Kristen Aldridge, who interviewed me and Cal Fussman for two separate videos featured on and Facebook Watch.

I first met Cal Fussman at a mutual friend’s home in 2017 and have appeared on his web series Breakfast With Larry where he moderates conversations with special guests and co-host Larry King.

I’ve also invited Cal as a speaker for our April 2019 Meeting of the Minds in Napa Valley, where he shared “best practices” with us regarding asking BIG QUESTIONS in order to squeeze the most out of life.

If you host a podcast, write a blog or email newsletter and feature subject matter experts in your field as I do, or want to more effectively screen candidates for a job position you’re hiring for, Cal emphasizes focusing on the following:

  1. Do the work ahead of time.

    Cal has a practice of brainstorming all the questions he has for an interviewee, then leaving his list behind as he enters the room for a recorded conversation. His belief is the “good sh*t sticks”, but it doesn’t mean he hasn’t read your book, researched you online, or dreamed all the fascinating perspectives you might have to share if you’re his subject for an article or guest for his podcast.

  2. Aim for the heart first, then the head.

    Your first question should elicit positive emotional responses. Another Meeting of the Minds alumni Luke Brady calls this “conversational jiu-jitsu”, but basically you want to lead someone to think about something happy, warm, and fuzzy. Cal likes to ask interviewees something along the lines of, “what’s the greatest lesson your mother/father taught you growing up?” Immediately, the interview becomes a conversation and it becomes easier to dive into more logical questions about strategy, tactics, and “lessons learned” in the moments to follow.

  1. Save your hardest-hitting question for the end.

    Cal builds rapport with an interviewee and perhaps shares some of his personal experiences to further connect with someone before closing an interview with the difficult stuff like the “I’ve gotta ask…” inserts related to scandals, regrets, or even exciting prompts on upcoming announcements (like a product launch) that might not be public knowledge yet.

Click the video below to hear more from Cal Fussman about how changing your questions can change your life (and business) for the better:

6 minute, 32 second feature of Cal Fussman for “Project Luminary” on

What are some of your favorite questions to ask friends, clients, and strangers alike?

And, was this helpful or interesting to you?

Shoot me an email at to let me know, or comment below if you’re viewing this on the Meeting of the Minds substack.



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Jared Kleinert is the founder of Meeting of the Minds (, as well as a TED speaker, 2x award-winning author, and USA Today's "Most Connected Millennial".

Meeting of the Minds curates "super-connectors" and subject matter experts as invite-only attendees to 3 day summits in places like Napa Valley, Bermuda, and elsewhere, as well as “deep dives” such as this Marketing and Biz Dev strategy & implementation workshop. Members of the MOTM network include CEOs of 7, 8, and 9-figure businesses, creators of globally-recognized brands and social movements, New York Times bestselling authors, founders of pre-IPO tech unicorns, c-suite execs from Fortune 500 companies, and others.

Jared's career began at 15 years old when he started his first company, and took off at 16 while working as the first intern, and then one of the first 10 employees, for an enterprise SaaS company called 15Five, which today has raised over $40M and has almost 2000 forward-thinking companies as monthly recurring clients.

Later, Jared would become a delegate to President Obama's 2013 Global Entrepreneurship Summit in Malaysia, write multiple books including the "#1 Entrepreneurship Book of 2015", and speak at TED@IBM the day before he turned 20. 

As a highly-sought after keynote speaker and consultant, Jared’s clients range from organizations like Facebook, Samsung, Bacardi, Estee Lauder, IBM, Cornell, Berkeley, AdAge, and the National Speakers Association. His insights on entrepreneurship, networking, marketing, and business development have been featured in Forbes, TIME, Harvard Business Review, Fortune, NPR, Entrepreneur, Mashable, Fox Business and more.

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