I’m Not Sure I’m Up to the Task

Comfortable jobs equal drifting employees. Everyone in your organization needs to feel stretched in some area.

Successful leaders help others step into uncomfortable – stretching – challenges and opportunities. Eventually, you’ll hear, “I’m not sure I’m up to the task.”

Helping people grow
means making them uncomfortable.

It doesn’t matter if you think they are ready. The issue is exploring the challenge from their point of view. Use this series of questions to guide your conversation.

Long version:

Clarify the challenge:

Describe the project or initiative in your own words. What are you doing?

What are the deliverables?

What is a win?

How do organizational values connect with this activity?

How does this activity express organizational mission?

Explore skills:

On a scale of 1-10, how important are the following skills to the success of your project?

  1. Organization and planning. ____
  2. Budgeting. ____
  3. Inter-departmental communication ____
  4. Organizational communication ____
  5. Public communication. ____
  6. Technical. ____
  7. Relationship building. ____
  8. Initiative. ____
  9. Follow through. ____
  10. Reporting. ____
  11. Collaboration or acting independently. ____
  12. Initiate and sustain teamwork. ____
  13. Problem solving. ____
  14. Decision making. ____
  15. Creativity, openness, and innovation. ____
  16. Adaptability. ____
  17. Supporting/developing others. ____
  18. Motivation and inspiration. ____
  19. Risk taking. ____
  20. Strategic planning. ____
  21. Listening. ____
  22. Delegation. ____
  23. Giving feedback. ____
  24. Integrating new people. ____
  25. Research. ____

Personal discussion:

Why are the high ranking skills important?

Which high ranking skills reflect your strengths?

Which high ranking skills reflect your weaknesses?

How stretched does this project make you feel? ____ (1-10)

What most stretches you?

How important to your career path is developing in the stretch areas? ____ (1-10)

How could you leverage the strengths of your teammates?

What support is important? (describe and discuss)

Would you like to move forward or should I find someone else?

Short version:

I’d like you to step into this new challenge. What do you need to succeed?


Use the long version with timid teammates.

How would you develop or change this structure?

How do you help people step into new challenges?