7 No-Nonsense Questions that Challenge People without Being a Jerk-Hole

Successful leaders challenge people. Jerk-holes are just pushy. But the opposite of pushy – being a push-over – isn’t an option for leaders.

Woman jumping across a valley.

The goal of challenging people is for people to challenge themselves.

7 fundamentals of assertive challenge:

  1. Rushing to challenge is pushy.
  2. Talent enjoys healthy challenge. Healthy challenge brings energy, growth, and confidence.
  3. Too much challenge crushes the spirit. Too little challenge insults talent.
  4. Avoid challenging all the time. Don’t 10X everything.
  5. Don’t bludgeon people with their success by constantly pressing for more with less.
  6. The goal of challenging others is for people to challenge themselves. Help people to set their own stretch goals.
  7. Challenge in ways that strengthen relationships.

7 questions to ask before you challenge people:

  1. What do you want for yourself? If you achieved that, what would be true for you?
  2. What are you good at? What makes you say that?
  3. Why did we hire you?
  4. Where would you like to be next year at this time? Why is that important to you?
  5. When you’re working, what gives you energy? How might that energy take you to the next level?
  6. On a scale of 1 to 10, how challenging is this new opportunity? (1 = not at all. 10 = off the charts.)
  7. If they choose 7 on the above challenge scale, ask how might you make it an 8?

7 no-nonsense questions that challenge people:

  1. What would make your goal a little more challenging?
  2. How might you reach a little higher?
  3. What’s preventing you from taking on this new opportunity? How might you remove that obstacle?
  4. What if you’re selling yourself short?
  5. If you reached higher, what might you try?
  6. What if you have more in you?
  7. What’s the bravest thing you can do?

“Keep away from people who try to belittle your ambitions. Small people always do that, but the really great make you feel that you, too, can become great.” Mark Twain

How are you balancing challenge and support?

What challenge techniques work best for you?