Three Questions Future-Ready Leaders Need to Ask Themselves

Cheryl Cran

August 09, 2018

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Future-ready leaders question the status quo by challenging assumptions and asking better questions.

In the past, leaders didn't question the rules, they followed them, and they didn't challenge the status quo; they did what he or she was told.

Image Source: 123RF

Today, following the rules can lead to extinction (think the leaders of Kodak who followed the rules sticking with print photos and not pursuing digital even though they had the technology before anyone else).

Or Blockbuster and how they stuck to the rules of VHS and DVD, but could have easily been market leaders in digital downloaded programming before Netflix came along.

The need for critical thinking and better questions is crucial for leaders to keep an edge for opportunities and to innovate before becoming extinct.

Three Questions Future-Ready Leaders Need to Ask Themselves:

  • What if what we feared the most in our business were to actually happen?
  • What am I most afraid of with the direction our business is heading?
  • What would a future look like if the things we dreaded were to come to be?

These questions may seem negative. However, what they do is help leaders be truthful about the future, rather than avoid the things they fear the most.

When a leader is willing to face the future with the lens of truth, there is boldness and a candidness that leads to better questions for the team.

Once you, as a leader, ask yourself the above questions, then you can bring bigger and more expansive questions to your teams.


  • Can we imagine a future, in our industry, where all jobs will be replaced by robots? What would that look like?
  • Does our business solve big-world problems, such as poverty or injustice?
  • How can we serve a bigger ‘why'?

The future demands that all leaders ask different and challenging questions to get to new levels of innovation as we lead towards the future of work.

This article was originally published on NextMapping.

Cheryl Cran is a future of work expert and the founder of, a future of work research and consulting firm that helps leaders, teams, and entrepreneurs be future-ready. She is the author of six books, including her new one due out at the end of 2018 titled, "NextMapping—How Great Leaders Inspire People to Create the Future of Work."

Opinions expressed by the author are not necessarily those of WITI.

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