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.
7 fundamentals of assertive challenge:
- Rushing to challenge is pushy.
- Talent enjoys healthy challenge. Healthy challenge brings energy, growth, and confidence.
- Too much challenge crushes the spirit. Too little challenge insults talent.
- Avoid challenging all the time. Don’t 10X everything.
- Don’t bludgeon people with their success by constantly pressing for more with less.
- The goal of challenging others is for people to challenge themselves. Help people to set their own stretch goals.
- Challenge in ways that strengthen relationships.
7 questions to ask before you challenge people:
- What do you want for yourself? If you achieved that, what would be true for you?
- What are you good at? What makes you say that?
- Why did we hire you?
- Where would you like to be next year at this time? Why is that important to you?
- When you’re working, what gives you energy? How might that energy take you to the next level?
- On a scale of 1 to 10, how challenging is this new opportunity? (1 = not at all. 10 = off the charts.)
- If they choose 7 on the above challenge scale, ask how might you make it an 8?
7 no-nonsense questions that challenge people:
- What would make your goal a little more challenging?
- How might you reach a little higher?
- What’s preventing you from taking on this new opportunity? How might you remove that obstacle?
- What if you’re selling yourself short?
- If you reached higher, what might you try?
- What if you have more in you?
- 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?

Thank you for this beautiful piece. It is important for a leader to see the potential in a person and challenge them to do more, better, and try different things to develop new skills. It becomes hard when that person does not see their own potential and is not willing to grow. At that time my thought is “it is a waste of human potential. How can I connect or reach this person? This is usually my challenge. Of course, over the years I was able to coach and support the growth of many young people. Should I just accept that I will not win a person all the time or continue to encourage and challenge in different ways?
The underlying concept here is that if you see more in the person than they see in themselves, you are challenging them, not being pushy. And it is important to help them see what you see in them so they can be successful.
Don’t let the push become the shove. Surely we need to connect with them on an equal level and then entice them with the I’m sure you can do this as you hvae done similar before. Encouagement can go a long ways, adding the flavor if your not comfortable I will come out and work with you. Granted not always the case, when you chose to support go the extra mile to accomplish the tasks.
I always liked the question—What can we (or you) do that’s never been done before?
Thanks for this piece, Dan. Very useful and smart. I’ll be sharing with a team of young managers who I advise.