How to Turn Cautious Teammates into Visionary Thinkers

Visionary thinking typically receives quick turndowns from cautious leaders. People start thinking small and safe.

Everyone dreams small when cautious judgmental leaders control decisions.


Traditional management culture encourages everyone to lower expectations and ask for less.

How to Turn Cautious Teammates into Visionary Leaders

#1. Establish direction.

Don’t ask for any visionary idea.

  1. Explain what matters now.
  2. Limit focus. We’re not working on….
  3. Seek suggestions for specific objectives, new initiatives, or important projects.
  4. Seek ideas that make work better for large numbers of people, not just one.

#2. Explain purpose.

Explain why you want to improve inter-departmental communication, for example. Are you working to create efficiencies, lower conflict, or prevent mistakes?

Purpose clarifies direction, fuels passion, and establishes boundaries for thinking.

#3. Narrow timeframes.

Make daring decisions that connect to near-term objectives.

  1. Over the next six months we’re working to improve cross-department communication.
  2. Our focus for January is lowering customer complaints by X%.
  3. During the first quarter, we’re working to build a work environment that makes co-workers and colleagues feel useful and valued.

#4. Ask for the big ask:

  1. What’s your big ask? The next time you want a visionary idea, explore options and then ask for the big ask.
  2. If you knew I was going to say ‘yes,’ what would you say?
  3. What’s the biggest improvement you can imagine?
  4. What are the three most daring things you could hope to achieve?
  5. If you were in charge, what would you try to accomplish?

#5. Determine a step in the right direction and take it.

  1. Establish a low cost pilot program.
  2. Invest in research. Survey customers, for example.
  3. Explain that this small ask is part of a big ask.
  4. Take a step. Evaluate. Adapt. Take the next step.

Cautious leaders drain creativity and boldness from teams.

How might leaders turn cautious teammates into visionary leaders?

This post is inspired by, “Why Are There Snowblowers in Miami,” by Steven D. Goldstein. (See chapter 4)