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Karin And David’s Leadership Articles

How to Develop Entrepreneurial Thinking on Your Team

Back in her Verizon days, one of Karin’s favorite questions to ask a team member whom she was encouraging to think like an entrepreneur was:

“If this was your company, would you  _______ (make this decision, hold this meeting, spend money in this matter, invest in this project)?”

As you can imagine, the answer was often. “Errr, well, no, but …”

The conversation after that “but” is at the heart of teaching your team how to think and act like an entrepreneur.

5 Ways to Help Your Team Think Like Entrepreneurs

Entrepreneurship is a chance to trade a solution to someone who has a problem that needs solving. Solve more problems, solve bigger problems, solve problems more widely, and you’re an entrepreneur. It’s tempting to industrialize this work, to make it something with rules and bosses and processes. But that’s not the heart of it. The work is to solve problems in a way that you’re proud of.” 

– Seth Godin

1. Hire problem solvers.

It’s going to be hard to teach your team to think like entrepreneurs if they’ve always been a “just tell me what to do-er.”

It’s much easier to encourage someone to think like an entrepreneur if they have a track record of innovation and problem-solving.

If you want to hire people with the capacity to think like an entrepreneur, ask about their experience.

  • What’s the best idea you’ve ever had to improve the business? Tell me about the idea. What did you do with it and what happened as a result?
  • Tell me about a time that you strongly disagreed with your manager. What was the issue? How did you work to resolve the conflict?
  • Describe the most difficult problem you’ve ever faced at work. How did you work to overcome it? What are you most proud of about your approach and what would you do differently the next time?
  • What’s the biggest mistake you’ve ever made at work? What did you learn?

Hire for courage and innovation and be clear from the very first day of new-hire orientation that you really want your new employees to share ideas.

2. Create clarity around where you need great ideas.

Don’t just tell your team you want them to “think out of the box,” Or that you have “an open door” for them to bring you new ideas. Be sure they clearly understand your strategic direction and what success looks like.

One of the biggest challenges we hear from our fast-growing start-up clients is that it gets more and more difficult to keep everyone aligned on what matters most as the business scales.

Be sure your town hall meetings talk more than EBITDA, with a clear message of “What I need from ya.”  And that you’re communicating your strategic priorities and what matters most at least five times, five different ways. 

3. Make information accessible.

It’s impossible to connect dots you cannot see. When a manager is struggling to think like an entrepreneur, it’s often that they don’t have access to the information they need to be resourceful.

4. Give them a piece of the business to own.

One of the most meaningful leadership conversations David had in his first executive role was informing the middle level and front line leaders that “This is your company.” They were used to a visionary leader calling all the shots, so it took some time for them to get used to the idea that they were responsible for their team and together, shared responsibility for the business.

You don’t need to give someone full P&L responsibility to help them act like an owner of their part of the business. If you want a manager to think like an entrepreneur, find ways to give them both influence and authority. (In general, try never to give responsibility without authority.) This could be a project, a market, and group of customers, or even a group of emerging leaders to develop.

Our strategic empowerment worksheet can help you work with the manager you’re looking to empower, to understand what decisions they can make and which they need to run by you.

5. Reward risk-taking and scaffold failure.

A big difference we see in our fast-growing start-up clients is that risk-taking is not only encouraged, but rewarded. Even when things don’t turn out as planned.

One way to build risk-taking muscles is to encourage and reward the act of taking the risk—especially before everyone knows the results. If you only reward successful efforts, that doesn’t encourage risk-taking—it only encourages “sure bets.” So scaffold your risk-takers with support so they know where to play and not blow up the business, and then reward the attempts.

Another way to do this is to turn your post-mortem meetings into post-meeting celebrations—where you celebrate the learning, the successes, and the “What we can do next times?”

Your Turn

Let’s start a conversation. If you’re part of a large organization, what advice do the big guys have for the start-ups? And the startups have for the big guys?

See Also: 5 Ways to Become an Intrapreneur in Your Organization

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Karin Hurt and David Dye

Karin Hurt and David Dye help human-centered leaders find clarity in uncertainty, drive innovation, and achieve breakthrough results. As CEO and President of Let’s Grow Leaders, they are known for practical tools and leadership development programs that stick. Karin and David are the award-winning authors of five books including, Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Powerful Phrases for Dealing with Workplace Conflict. A former Verizon Wireless executive, Karin was named to Inc. Magazine’s list of great leadership speakers. David Dye is a former executive and elected official. Karin and David are committed to their philanthropic initiative, Winning Wells – building clean water wells for the people of Cambodia.

Be More Daring


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7 Practical Ways to be a Bit More Daring

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7 Practical Ways to be a Bit More Daring

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