9 questions to move you from do-er to thinker

Melissa Rosenthal
3 min readApr 9, 2021
Photo by Riccardo Annandale on Unsplash

For me, it’s hard to talk about leadership without talking about value. I challenge my clients to consider the extent to which they are maximizing the value they create— for each of their team members and their company. In a fast-growth scenario, assessing optimal value contribution is an ever-changing feast, requiring both deep reflection and agility from leaders.

Typically, when I ask this question, the conversation moves quickly to the tension between thinking and doing. The expectation that as their team grows, leaders will “step up” and shift to thinking more broadly about what is best for the business. And consider how to create meaningful opportunities for their team members to step up with them.

Clients reflect on the challenge of transitioning from creating value by doing to thinking. They describe a sense of loss. The loss of an ongoing sense of busyness where they would end the day exhausted but exhilarated by what they have “checked off their list”. That feeling is (at least) initially replaced by a sense of confusion or uncertainty. Sometimes they simply don’t know what to do. Other times the confusion relates to what they have achieved during the day, week or month. Over time that uncertainty chips away at self-belief and ability to successfully lead a team.

It’s no wonder. Defining your success in terms of thinking can be tough. Especially if you consider yourself to be someone who “gets shit done” (sound familiar?).

It often starts with a very daunting white sheet of paper.

A pre-prepared set of questions can help by creating structure and focus for your thinking.

Questions about the business, for example…

  • What are the most important problems for us to solve? Today? Over the next 12 months? Over the next 3 years?
  • Who are the people we need to help us solve these problems? When do we need them?
  • What data or other resources will we need access to?

Questions about how effort is allocated…

  • What time frame is appropriate for each member of the team? Who should be focusing on today, next quarter, next year and beyond?
  • How well understood is our decision-making process and authority? Are decisions being made by the right people at the right time?
  • How will we evaluate and prioritise new opportunities?

And questions about how to lead yourself and your team…

  • What will you stop doing to create opportunities for members of your team to grow?
  • How will you set clear, safe expectations for your team as you challenge them to step up? How will you support them as they do? What different types of feedback will you need to give them?
  • What will be your milestones and personal measures of success as you step up further into the thinking space?

This is not intended to be an exhaustive list. Rather, I hope it provokes thought and sparks ideas for you and your team. If you’ve got other questions that are working well that you’re happy to share, send them to me and I’ll add them to the list.

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