Top Questions to Engage Employees & Spur Strategic Thinking

Ask questions until you get the answers you want, and ask better questions with these examples taken from our resources and TeamStrength members. Engage with Skip-Step Meetings, review with Stay & Exit Interviews, and evolve with questions to jumpstart strategic thinking.

Questions for Skip-Step Meetings:

Skip-step meetings are 1-1 meetings held with employees by the manager two levels up. These create  opportunities for feedback and growth and skip-step can be an approach for Stay/Exit Interviews.

  1. Why did you decide to join our company? What were you most excited about?
  2. Are you happy with your career progress here? Why/why not?
  3. What have you accomplished lately that you’re most proud of? Since you’ve been here?
  4. What are your biggest concerns about [recent change]?
  5. What tweaks would you make to [change] to help you and your teammates?
  6. How do you measure success in your role?
  7. What’s blocking you from being more successful than you already are?
  8. What would you do differently if you were in the role of your team lead? Why?
  9. What are your professional goals during the next year here? The next 3 years?
  10. What do you think the current goals of the company are?
  11. How do you feel your role contributes to those goals?
  12. What ideas do you have for innovation in your team? In the company?
  13. What is one thing we need to START doing right away to be more successful?
  14. What is one thing we need to STOP doing right away to be more successful?
  15. What is one thing we need to make sure we CONTINUE to do in order to be successful?

Stay & Exit Interviews

Our HR Leaders shared insights on the power of the Stay Interview, and to a lesser degree Exit Interviews, to gain insights that can help with retention. Our HR Leaders find the quality and impact of Stay Interviews typically much higher than Exit Interviews.

Top Questions for Stay Interviews:

  1. When you travel to work each day, what things do you look forward to?
  2. When was the last time you thought about leaving our team? What prompted it?
  3. What can I do to make your experience at work better for you?
  4. The last time you said, “I had a great day, I love my job,” what had happened that day?
  5. The last time you said, “That’s it, I can’t take it anymore,” what had happened that day?
  6. What is really different here that makes you proud to be an employee?
  7. What talents are not being used in your current role?
  8. Do you have clear goals you are working towards currently?
  9. What is your ideal job, and how can we help your progress towards it?
  10. What are your daily frustrations/challenges?

Top Questions for the Exit Interview:

  1. When was the first time you thought about leaving our company?
  2. Were you satisfied with your progress at this company? If not, why?
  3. What do you value/dislike about the company?
  4. Did you have clear goals and know what was expected of you in your job?

Questions to Spur Strategic Thinking

Getting employee buy-in on goals and initiatives starts with engaging them in strategic thinking. Use these questions below to help engage employees on the bigger picture, sampled from 9 Lenses.

  1. How often do you asses your team/department’s strengths, weaknesses, opportunities, and threats? How do you use this information?
  2. If you were in charge of strategic planning for the organization as a whole, what changes would you make?
  3. How efficient is your team from an operational standpoint?
  4. How well does your department utilize its people as an asset to help it improve, stay competitive, and strategically meet goals? Are people used efficiently or is talent wasted due to lack of effective strategy?
  5. How often do you analyze the competition in order to understand competitive advantages and disadvantages as well as identify areas for investment or needs for improvement?
  6. Do you understand how your organization’s strategy on differentiation and what we do best?
  7. What are the long-term goals of your department/the company? Do you short-term priorities line up with these goals? How?
  8. Is your organization pursuing growth and new business/market development with as much passion as it does operational efficiency?
  9. How effective is your organization’s strategic vision?
  10. When developing and implementing strategy, does your organization effectively balance short and long-term priorities?
  11. How efficient and organized is your organization’s plan for how to improve and evolve the strategic objectives over time?
  12. How many established connections does your organization have with consistent and dependable customers?
  13. How effective is your organization’s delivery model (service, product, value, etc.)? Is it clearly recognizable and understood by your ideal customers?
  14. To what degree are your offerings clearly differentiated in their market?
  15. Based on your knowledge of current efforts to promote your services, what are the major internal barriers to selling your services to clients?
  16. How well does your organization maximize existing resources in order to deliver the product offering?
  17. How well do the organization’s products solve the customers’ problems and meet their expectations?
  18. How frequently does your organization deliver new value-adding ideas to your customers to keep them engaged?
  19. Considering factors such as competition and timing of discounts, does your organization provide the right amount of discounts and at the right price?
  20. How often are your organization’s web strategies updated in order align with current organization news and capabilities?
  21. How effective is your organization at ensuring loyalty of current customers by extending various incentives for loyalty to your offerings?

PDF Link