The importance of asking challenging questions

Do you feel comfortable challenging the status quo at work? It’s important because to be successful we must be asking purposeful questions: Why are we pursuing this initiative? Why are we hiring this person? Why are we following this strategy?

Nigel Travis, executive chairman and former CEO of Dunkin’ Donuts and Baskin Robbins, has 40 years’ experience as a leader in large and successful organisations. In his book The Challenge Culture, Nigel argues that asking these tough questions is key to a company’s survival in today’s chaotic world. So, to help you get started, here are some questions you might ask about your culture and whether it encourages questioning, dialogue, and challenge.

A Checklist for Creating a Challenge Culture

  1. Do people in your company fear they will be fired if they challenge the status quo or question ideas or plans too forcefully or too often? Do you live in a you’re-fired or confrontational culture?
  2. What defines a culture that is not what you want yours to be?
  3. What are the constituencies that influence your business and how do they define success? Can these differences be aligned? Do they need to be?
  4. Have you defined and distributed the ground rules for civil dialogue in your organization?
  5. What qualitative skills are most important to your culture and business? How do you foster and encourage them (e.g., questioning, listening, debate, challenge, being interviewed, public speaking)?
  6. Do you value listening? Do you practice listening skills? Do you take notes during dialogues?
  7. Have you established channels and venues that provide regular opportunities for people to pose questions and make challenges to others at every level, including their bosses?
  8. Are your people able to challenge their peers and colleagues? How?
  9. Does the core management team consist of people who will challenge and question each other? Do they have a diversity of viewpoints and backgrounds?
  10. Do you have an emotional consigliere? A sparring partner?
  11. What role does HR play in your organization? Does it help create the challenge culture?
  12. Do you, and the members of your team, personally live and model the characteristics of the challenge culture?
  13. What have you learned about your culture from other industries, organizations, or activities?
  14. Have you anticipated your organisation’s potential demise?

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