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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:

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

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