Dear Dan: How Do I Challenge People
Dear Dan,
I’ve certainly been guilty of using pressure tactics in the past to get results out of my team members.
I’m curious, how should I express to a team member that I’m deliberately challenging for the sake of their growth, that they are being pressured for a specific reason?
Sincerely,
Conrad
Dear Conrad,
Thank you for your transparency and curiosity. These qualities fuel authentic leadership.
The third quality you display is most important. You seek the best interest of others. Your challenge is finding ways to advantage others that elevate and energize them.
How to Challenge People
Pressure tactics work, but they cost. Adopt a people-centered approach to challenge.
Challenge done TO people? That’s pressure.
Challenge done WITH people? That’s growth.
Reject pressure. Hire aspirational people and coach them to challenge themselves.
Challenge People to Challenge Themselves
Instead of saying, “This is a stretch assignment,” ask:
- “What level of challenge brings out your best? Where does this opportunity fit?”
- “How does this challenge serve your aspirational future?”
- “What strengths will this challenge help you develop?”
- “What support would make this challenge energizing instead of intimidating?”
- “How will you know you’ve succeeded?”
- “What’s the first small step?”
Coaching Principles for Challenging People
1. Share Ownership: Turn challenges into shared goals.
2. Connect to Purpose: Show how the challenge serves the team and the person.
3. Offer Choices: Choices make people feel powerful.
4. Calibrate Support: Ask what support would bolster their confidence. Stay available but intervene reluctantly.
5. Celebrate Progress: Progress fuels courage for the next challenge.
Don’t chase compliance.
Start thinking “How do we get stronger?”
What is the difference between challenging people and pressuring people?
How can leaders challenge people in ways that energize.
24 Ways to Challenge People Without being a Jerk-Hole
Building a Culture Where Employees Feel Free to Speak Up HBR






Challenging people means stretching them beyond their comfort zone while showing confidence in their ability to succeed. Pressuring, on the other hand, focuses on the negative consequences of failure.
I’ve found the best challenges are those tied to areas where people already have a genuine interest.
In this sense, challenge is a personal thing. The skill is aligning personal interest and organizational objectives.
I cannot begin to tell you how timely this question and response are. Thank you Conrad and thank you, Dan!
I wish you success. Thanks for stopping in.
I have sometimes told people that I am the lifeguard on the side of the pool. If they need me, I am ready to jump in. I may jump in because they call for help. I may jump in because I can see they need help. But I am not going to jump in just because they are splashing around.
Let people splash around! Love it.