35 Impactful Questions Managers Should Ask Themselves Regularly

We asked top startup leaders to share the questions they ask themselves to become better managers and assembled their answers into a can't-miss checklist.

QUESTIONS FOR GAUGING TEAM MORALE

1. Who haven’t I heard from?

Often managers won’t hear much from their highest performers, who are heads-down building and cranking out results. It's vital to remain attentive to those individuals who might be quietly working through challenges.

Not everyone is going to be a squeaky wheel. As a manager, you need to be listening for what you’re not hearing as well.

2. How well do I know my team members? How well do they know each other?

It's paramount that you know your team personally. Understanding their backgrounds and aspirations is crucial for building a sense of belonging and enhancing performance.

3. Have I made a difference to each member of my team this week?

Regular check-ins can help ensure that each team member feels valued and supported.

4. Have I expressed gratitude to every single person on my team recently?

Recognizing contributions fosters a positive work environment and reinforces team cohesion.

5. Is anyone a flight risk?

Regularly assess team morale and look for signs that anyone may be disengaged or overwhelmed.

QUESTIONS FOR TRACKING TEAM PERFORMANCE

6. Is each member on the team overperforming, on track, or underperforming?

Understanding the performance levels of your team members helps tailor support and development accordingly.

7. What resource recommendation can I send someone this month?

Encouraging continuous learning and development can greatly benefit team growth.

8. Does my team know what success looks like for their role?

It's vital to ensure that team members fully understand their goals and expectations.

9. Does my vision for the team member’s trajectory line up with their vision for their own career trajectory?

Regular discussions on career paths can align both managerial and employee aspirations.

10. In the last six months, has each member of the team grown in noticeable ways?

Reflect on individual growth and development to identify areas for further support.

11. If I could just wave a magic wand and have a new candidate replace this position, would I want to do it?

This can reveal the necessity of tough conversations regarding performance.

12. Does my team know what their superpowers are?

Recognizing each team member's strengths is essential for job satisfaction and effectiveness.

13. What are the challenges ahead of our team?

Identifying challenges helps in setting clear priorities and strategies.

QUESTIONS FOR MEASURING YOUR EFFECTIVENESS AS A MANAGER

14. Does the team know what the strategy is (not just our tactics)?

Ensure your team understands the broader goals beyond day-to-day tasks.

15. Is anyone on the team just cranking out work without context?

Provide context for tasks to motivate team members effectively.

16. What more can I say no to?

Clarifying priorities is crucial for effective management.

17. Could my team function without me?

Encouraging team independence strengthens their capabilities.

18. What’s one thing on my plate that I can delegate to my team?

Delegation empowers your team and allows you to focus on higher-impact tasks.

19. When was the last time I asked for feedback?

Open channels for feedback strengthen relationships within the team.

20. How many times did I ask questions versus give answers this week?

Encourage critical thinking by asking more questions instead of providing direct answers.

QUESTIONS FOR BETTER DECISION-MAKING

21. How sure am I?

Regularly reflecting on your decision-making confidence is essential for effective leadership.

22. Am I operating from a place of security or panic?

Be mindful of your mindset during decision-making.

23. What would be a completely different approach to this answer, project, or problem?

Challenging assumptions can lead to creative solutions.

24. Am I hearing the group’s problems?

Listening deeply can reveal underlying issues that need to be addressed.

QUESTIONS FOR MANAGING UP & SIDEWAYS

25. Do I know what’s important to my boss right now?

Alignment with your manager's priorities is crucial for effective collaboration.

26. What is my team being paid to do?

Reflect on the value your team brings to the organization to maintain focus.

27. If the business were a person, would they significantly benefit from my organization’s priorities and efforts?

This reflection helps highlight potential disconnects between actions and outcomes.

28. What have I been hesitating to share, create, or take action on?

Overcoming hesitance can enhance team progress.

29. What does the person on the other end need to know?

Keeping communication clear and concise prevents misunderstandings.

30. How can I drive conversation across teams?

Promoting inter-team dialogue fosters collaboration.

QUESTIONS FOR FOCUSING ON YOUR PERSONAL WELL-BEING

31. What energized me today?

Regular self-reflection on energy levels can guide your daily actions.

32. Am I being kind to myself?

Practice self-compassion to maintain emotional fitness.

33. What can I learn from this?

Adopt a learning mindset to foster growth opportunities.

34. Was I busy or productive today?

Evaluate productivity to manage time more effectively.

35. What do I want to practice?

Focus on continuous improvement by setting personal development targets.