Magic Questions

Looking for a calibration tool to understand how your people are doing?

I've watched leaders transform their relationships with their teams by asking these five simple questions on a regular cadence. By including personal life, you manage the whole person, not just their work. This encourages transparency and builds trust.

Start with an audacious vision

What is your five-year career vision?

Invite them to imagine themselves five years in the future. Where do they live? What does their relationship look like? What kind of energizing, inspiring work are they doing? Who do they work with? What’s their financial situation?

Push them to get creative and ambitious. Anything is possible.

You only need to ask this the first time. It anchors everything that follows.

Ask these questions quarterly

5 = couldn't be any better
3 = meeting expectations
1 = couldn't be any worse

Rate each question 1–5:

1. Is what you are doing now at work leading toward your career vision, 1-5?

2. How are you feeling about your life at work, 1-5?

3. How are you feeling about your personal life, 1-5?

4. How are we performing as a company, 1-5?

5. What is it like to work with your peers, 1-5?

Choose the lowest score and unpack it by answering,

What would get this to the next level?

If it's a 2, what would get it to a 3? Commit to a next action with a date.

Going deeper on personal life

When someone rates their personal life lowest, you can unpack it further. Ask them to rate these dimensions:

• Relationship, 1-5?

• Home, 1-5?

• Money, 1-5?

• Time with friends and family, 1-5?

• Fun and entertainment, 1-5?

• Physical health, 1-5?

• Mind and soul, 1-5?

Again, choose the lowest score and answer, what would get it to the next level?

Templates

• Google Docs

• Notion