In this episode: Building on Season 1’s first two episodes, Jon Peyton asks how to test for the entrepreneur’s mindset in yourself and in the people you hire. He walks through four traits, confronting self-doubt, accountability, resilience and a willingness to experiment, and explains which three you should hire for.
Key insights
- MasterClass describes four traits of an entrepreneurial mindset: confronting self-doubt, accountability, resilience and a willingness to experiment.
- People who can confront self-doubt keep solving problems instead of spiraling.
- Accountability starts with yourself. If you can’t keep commitments to yourself, it’s hard to keep them to others.
- Resilience means learning from failure and continuing to push forward.
- Hire for the first three traits. Give risk-takers clear limits, because they’re experimenting with your money.
Episode timeline
- 0:00 Testing for the entrepreneur’s mindset
- 0:45 What the entrepreneur’s mindset is
- 2:02 Trait one: confronting self-doubt
- 5:01 Interview questions that reveal it
- 6:44 Trait two: accountability
- 11:20 How to test for accountability
- 13:24 Trait three: resilience
- 16:08 The value of persistence
- 17:39 Trait four: a willingness to experiment
- 22:06 Setting limits on risk
- 24:11 Which traits to hire for
The episode in brief
Defining the mindset. MasterClass describes the entrepreneurial mindset as the way of thinking that helps you create, develop and run your own business, and names four traits: the ability to confront self-doubt, accountability, resilience and a willingness to experiment. Jon looks at each one and asks whether you should hire for it.
Confronting self-doubt. When you’re solving a problem nobody has solved, there’s no manual. You don’t know if you’re on track until a process starts producing results you can repeat, and self-doubt fills the space in between. People who can acknowledge that failure is part of learning, trust the process and pivot are good problem-solvers. To test for it, ask how a candidate handles feedback, or how they’d react if they spent 20 minutes stuck on the first puzzle in an escape room.
Accountability. Think of New Year’s resolutions: life gets in the way, and the goal slips. Accountability means staying with the process, and when you get off track, getting back on rather than starting over. No one is perfect, but being consistent most of the time still moves you forward. People who aren’t accountable to themselves tend to make excuses with others. Ask candidates about a recent challenge, the biggest goal they set and reached, and how they course-corrected along the way.
Resilience. New paths take time, energy and patience, and the first path is rarely the final one. Success often comes after many attempts, and Thomas Edison’s long search for a working light bulb is the classic example. People who bounce off adversity struggle when they hear “no.” Coach them, and make sure they know their team and their leaders will help them solve problems.
A willingness to experiment. This is what separates the entrepreneur from the employee. Executives may experiment within paths they’ve walked before. A true entrepreneur is solving a new problem without a map. That’s essential for you as the founder, but be careful hiring for it: risk-takers are experimenting with your time, money and customers. Define the limits. For example, give a marketing lead $50,000 of a larger budget to test a new channel, not the entire year’s budget.
Hire for three. People who can confront self-doubt, stay accountable and stay resilient will problem-solve their way over, around or through walls. Test yourself for all four traits, and build the first three into your hiring process for leaders and frontline staff.
Key action items
- Score yourself. Rate yourself on each of the four traits and note where you struggle.
- Add mindset questions to interviews. Ask about feedback, setbacks, goals reached and how candidates course-corrected.
- Build an accountability process. Set up a simple way to get back on track when you or your team slip.
- Coach resilience. Make it clear that failure is part of the process and that help is available.
- Cap the experiments. Give risk-takers a defined budget and timeline so a failed test can’t sink the business.
Listen next: Episode 41: The Entrepreneur’s Rocky Roadmap
This episode is educational and isn’t legal, tax or financial advice. Speak with your own attorney and advisers about your situation.