Ask a CEO

Ask CEOs about hiring, growth, leadership, and running a company. Each one answers from their own interviews, talks, and posts.

Updated

Jason M. Lemkin

CEO of SaaStr; co-founded EchoSign and scaled it through its acquisition by Adobe

Scaled EchoSign to $100M+ ARRRuns SaaStr Fund

Why themDirect on B2B sales, fundraising, and scaling to $100M ARR.

Why is leadership important?

Leadership matters because talent without alignment cancels itself out. I saw it scaling EchoSign and now see it in portfolio companies: 50 great people pulling in different directions will lose to a smaller team pulling the same way. Your job as a leader is to make the direction obvious, make debate real, and then decide fast so the vectors actually add up.

How asking a CEO on Delphi works

Each CEO here has a Delphi, a Digital Mind built from their own interviews, talks, posts, and podcasts. You ask in your own words, by text or voice, and it answers the way they would.

You'll find CEOs of software, AI chip, media, franchise, and industrial companies. Ask the one who has run a company like yours.

  1. Pick a CEO

    Start with someone who has worked on the problem you have.

  2. Ask in your own words

    Type or talk. Describe your situation the way you'd explain it to them in person.

  3. Keep going

    Ask follow-ups until you have what you need. You can try a few questions without an account, and sign in to keep your conversations.

Why Delphi is the best place to learn from ceos

Real ceos, in their own words
Every Delphi here is built from that person's own interviews, talks, posts, and podcasts, and they decide what it covers.
Answers for your situation
Describe what you're dealing with, then keep asking follow-ups until the answer fits you.
Many voices on one question
See how the CEO of Automattic, the CEO of SaaStr, and an industrial CEO answer the same question.
Any time, text or voice
Ask at any hour, by typing or by talking, in more than 40 languages.

Questions people search for

Answered by people who've lived them.

How do you become a good manager?

Several of these CEOs had to learn management as a separate skill. What they describe: listen, give clear direction, hold people to results, and put the right person on the right work.

  • Andrew FeldmanAndrew FeldmanCo-founder and CEO of Cerebras Systems, which builds wafer-scale chips

    I learned to manage by doing the work no one wanted to do, making my peers' jobs easier, and letting people choose to follow me before I had the title. At Cerebras, going from 25 to 800 people forced me to reinvent that every few years: one-to-one became one-to-many, and the job turned into repeating the story so everyone saw where they fit.

    Ask Andrew a follow-up
  • Matt MullenwegMatt MullenwegCEO of Automattic and co-founder of WordPress

    I was a terrible manager early on, so I started reading everything I could, from the Stoics to Good to Great, and brought in mentors and structure because I realized leadership is a craft you have to study deliberately. Lara Hogan, who I had on the podcast, put it better than I could: the secret is listening, really listening, which sounds obvious but is the hardest thing to do when you first start managing people.

    Ask Matt a follow-up
  • Bill CanadyBill CanadyCEO of Arrowhead Engineered Products and founder of The 80/20 Institute

    Good management starts with giving people clear direction and then holding them accountable for results, not activity. I learned early that people rise to the level of your belief in them, so I frame feedback as I believe you can be better, not you are not good enough. Progress is not perfection.

    Ask Bill a follow-up

How do you motivate employees?

Andrew Feldman and Bill Canady say speeches, slogans, and perks don't do it. Most of these CEOs point instead to real ownership of the work, a visible path to grow, and recognition.

  • Matt MullenwegMatt MullenwegCEO of Automattic and co-founder of WordPress

    I don't think motivation is something you do to people. Daniel Pink's book Drive shaped a lot of how I built Automattic: people need mastery, autonomy, and purpose. Give them real agency over how they work, let them get better at something hard, and connect the day-to-day to a mission they actually believe in.

    Ask Matt a follow-up
  • Andrew FeldmanAndrew FeldmanCo-founder and CEO of Cerebras Systems, which builds wafer-scale chips

    I don't think you motivate people with slogans or perks. After hiring more than 15,000 people over 25 years, I've seen that what keeps them is interesting work, colleagues they respect, and leadership they trust to act with integrity. Get those three right and the rest tends to follow.

    Ask Andrew a follow-up
  • Vishen LakhianiVishen LakhianiFounder and CEO of Mindvalley, a personal transformation education company

    I stopped trying to motivate people and started helping them grow instead. At Mindvalley, I have lunch with every new hire and ask where they want to be one year from now, then we map their growth to their work.

    Ask Vishen a follow-up

Why is leadership important?

Leadership turns individual talent into results. These CEOs say it points people in one direction, builds the trust a team needs to act, and turns a plan into execution. Without it, a large team pulling different ways loses to a smaller one pulling together.

  • Jason M. LemkinJason M. LemkinCEO of SaaStr; co-founded EchoSign and scaled it through its acquisition by Adobe

    Leadership matters because talent without alignment cancels itself out. I saw it scaling EchoSign and now see it in portfolio companies: 50 great people pulling in different directions will lose to a smaller team pulling the same way. Your job as a leader is to make the direction obvious, make debate real, and then decide fast so the vectors actually add up.

    Ask Jason a follow-up
  • Andrew FeldmanAndrew FeldmanCo-founder and CEO of Cerebras Systems, which builds wafer-scale chips

    Leadership is the only way you turn a room full of smart individuals into a team that ships something impossible. At Cerebras, I watched that shift from 25 of us eating lunch together to 800 people across time zones, and the job became repeating the story so clearly that someone I had never met still knew why their work mattered.

    Ask Andrew a follow-up
  • Bill CanadyBill CanadyCEO of Arrowhead Engineered Products and founder of The 80/20 Institute

    Leadership is the only force that turns a good plan into a result. I have watched companies with average strategies and strong leaders beat companies with brilliant strategies and weak ones, because leadership is what creates clarity, accountability, and the courage to act.

    Ask Bill a follow-up

What does a product manager do?

A product manager decides what gets built, for whom and why, then gets engineering, design, and the business behind that decision. These CEOs add two parts: time with customers to learn what they need, and checking the usage data afterward to see if it worked.

  • Matt MullenwegMatt MullenwegCEO of Automattic and co-founder of WordPress

    A product manager is the person who decides what gets built and why, then rallies design, engineering, and the business around that decision. When I was a PM at CNET, I learned that the hardest part isn't the roadmap; it's translating user pain and company goals into something a team can ship.

    Ask Matt a follow-up
  • Jason M. LemkinJason M. LemkinCEO of SaaStr; co-founded EchoSign and scaled it through its acquisition by Adobe

    A product manager's job is to spend more time with customers than anyone else, figure out what they actually need, and translate that into a roadmap engineering can ship.

    Ask Jason a follow-up
  • Andrew FeldmanAndrew FeldmanCo-founder and CEO of Cerebras Systems, which builds wafer-scale chips

    A product manager is the person who decides what gets built, why, and for whom, then makes sure engineering, sales, marketing, and customers all line up behind it.

    Ask Andrew a follow-up

Who answers

All 11, in one list.

Questions

Can I ask about my own company?

Yes. Describe your stage, your team, and the decision in front of you, then ask follow-ups.

What is a Delphi?

A Digital Mind built from a person's own words: their books, talks, interviews, posts, and podcasts. Ask it a question and it answers the way that CEO would, based on what they've said.

Am I talking to the CEO?

You're talking to their Delphi. Each CEO chose to build it and decides what it covers, and it answers from their own material.

Is Delphi free?

Yes. Talking to any CEO's Delphi is free, by text or voice.

How do I start?

Pick someone above and ask your question in your browser, by typing or talking. You can try a few questions without an account; sign in to keep your conversations.

Are my conversations private?

The person whose Delphi you talk to can see your conversations with it, so share only what you'd tell them. You can delete your account at any time and ask for a copy or deletion of your data.

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