Using Questions to Develop an Entrepreneurial Leadership Mindset in Others


August 2017 | By: By Babson Executive Education

Estimated reading time: Estimated reading time: 4.5 minutes

Key Takeaways


  1. Effective managers can use thoughtful questioning to bring out the best in their teams.
  2. There is an art and science to questioning so that it’s not an interrogation, but rather a productive conversation that sparks new ideas and insights. Ask questions of everyone: customers, direct reports, managers, project stakeholders, personal networks, and beyond.
  3. Often, the most precious resource is time. Don’t squander it—take action quickly, learn, and try again!


It’s not enough to develop an entrepreneurial leadership mindset in yourself, to get your organization to act entrepreneurially you need to develop this mindset in others. One of the best ways to coach and help grow this skill in your team is by asking questions as you meet with your leaders to get updates, solve problems, and plan future activities.

Here are a set of potential questions for different scenarios. Pick a few that seem appropriate for the situation, or are appropriate for the kind of thinking you want to promote in your managers.

Taking Stock: Using the Resources at Hand to Act Quickly

Entrepreneurial leadership is about using the resources you have to quickly brainstorm, develop, and evaluate the potential of new ideas or opportunities. Most people tend to underutilize their resources and end up relying too much on their own thinking and effort, which limits creativity and progress. Smart questions can help people reflect on their current and potential use of available resources.

Quickly Engaging Customers and Key Stakeholders

For most initiatives, the key to rapid learning and development is to engage customers and key stakeholders as quickly as possible to generate, evaluate, and refine ideas, technologies, and processes. Early customer engagement can help eliminate bad ideas quickly, rapidly confirm the potential of good ideas, and uncover hidden customer needs, critical design variables, unexpected issues, or unintended consequences. Ensure leaders are using their personal network (and their team’s networks) to reach out to existing or potential customers and key stakeholders.

Managing Risk through Affordable Loss

Contrary to popular opinion, successful entrepreneurs are actually somewhat risk-averse. Instead of trying to predict and manage risk, they only risk what they can afford to lose at the moment. Entrepreneurial leaders rarely make big bets. Instead, they break their efforts down into a series of thoughtful little bets that help them evaluate and improve ideas before risking more time, effort, resources, and reputation. While budgets and reputations are important, the one thing that leaders can often least afford to lose is time. A little bet strategy helps avoid spending too much time on bad ideas. Effective coaching in this area helps leaders find ways to manage risk with a series of little bets.

Reducing Barriers to Entrepreneurial Action and Rapid Learning

As a manager and coach, your role is to identify, remove, or reduce any organizational barriers preventing individuals and groups from leading entrepreneurially. Lots of things can derail entrepreneurial action, for example incompatible reward systems, byzantine approval processes, and complicated, time-consuming reporting. These norms and systems are often taken for granted in that individuals and groups may not even recognize them as elements that stymie learning.

Providing Help Beyond Coaching

You may be in a position to provide support that goes beyond coaching. This is especially true if you are the leader’s boss, or control many of the people and resources they need to move the project forward. The next time you’re unsure about exactly how to help, instead of looking for the answer, look for the question.

Try asking a few of these questions the next time you’re coaching an entrepreneurial leader:

Take stock of your resources and act quickly

  • What can you do quickly with the people, equipment, and resources you have now?
  • Are you using all the resources you have now to move this project forward quickly?
  • What skills, knowledge, and connections do you personally bring to the project?
  • How can you use them to move this project forward quickly?
  • Do your strengths, interests, and personal network suggest a particular approach or first step?

Quickly engage customers and key stakeholders

  • Have you talked to customers about this idea? What have they said? Are there any patterns or consistencies to their reactions? Could they help you improve this idea?
  • Would talking with a few customers right away help you figure out which direction to take?
  • Is there anyone else you could talk to right away to help you quickly develop this idea?

Manage risk through affordable loss

  • What would we lose if we tried this idea and it didn’t work? How much time, effort, and money are at risk here? Can we afford it?
  • Should we take a smaller step that risks less time, money, and effort, but might help us more quickly decide if this is a good idea?
  • What would you lose if this initiative failed? How do you feel about that?

Reduce barriers to action and rapid learning

  • Is there anything I’m asking for that is slowing you down? Not helping you learn quickly?
  • Is anyone else doing things to slow you down? Are there things that you are doing that you don’t think are helping you learn quickly?
  • What can we adjust, simplify, or remove from our organizational processes to help you learn and develop things more quickly?

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