Welcome to the Box of Questions

Great people managers know that it is usually more about asking the right questions than giving the answers. The best leaders help their team to be more agile, innovative, productive and responsive – to deliver their best work. Asking your team members the right questions can help you do that.

Each card gives you a list of questions that will help you:

  1. Recruit the right people
  2. Coach your team to better performance
  3. Keep your team engaged
  4. Keep your best talent
  5. Guide your team’s careers
  6. Support your team’s health and well-being

All of the questions are based on the latest trends in people management and what we have seen work well in the most progressive and successful organisations around the world.

We know when you recruit you are not just looking for the technical skills but someone who will be a good fit with your organisation’s culture and values. Remember candidates can still share your values but have different backgrounds, experiences and styles!

Here are a few questions you can ask face to face or ideally in a pre-screen Zoom call:

Motivation for working in your organisation

  1. What attracted you to the role?
  2. Why are you looking to leave your current role?
  3. What would be your ideal next move and why?
  4. What are your future aspirations?
  5. What other roles are you currently considering?
  6. Let me tell you more about the role and our culture here..

Relevant Experience

Culture fit

  1. Tell me the one thing that is the most important to you in making your next career move? Is it money, flexibility, challenge, stability etc.
  2. Describe the management style that brings out the best in you? Can you give an example of a manager that didn’t bring out the best in you and why?
  3. If one of your co-workers had a “this is how we’ve always done it” attitude to something new, how would you try to convince them to try a different approach?
  4. What kind of culture do you enjoy working in?
  5. You have been working on a project for a while, when your manager informs you that the project’s requirements changed suddenly. What would you do?
  6. What do/did you love most about your previous/current job?
  7. What are the negative aspects of your previous/current job?
  8. Tell me about a time you had to work with a colleague you didn’t get along with?
  9. What learning and development have you done recently?
  10. What’s been the toughest criticism you received so far in your career? What did you do with it?
  11. Tell us about your biggest failure? What went wrong? How did you recover?
  12. What big decision did you make recently? How did you go about it?
  13. What trends do you see impacting our industry?

Coaching someone helps them to unlock their potential and improve their performance. It is about helping them to learn, rather than teaching them. To be a great coach you need to listen more than you talk and as tempting as it might be, not to jump to the answer – but ask questions so that they come up with the answer themselves. Coaching is about giving them the opportunities to put what they’ve learnt into action, have their back if they get it wrong and give ‘in the moment’ feedback on how they’re doing.

Here are some coaching questions you can ask at your next check-in: 

  1. What are you working on at the moment and how can I help?
  2. What else would you like to discuss today?
  3. This is what I’ve noticed that’s gone really well recently and why. What do you think?
  4. I really appreciate you for …. and just wanted to say thank you.
  5. Do you feel you’re able to use your strengths every day?
  6. What do you think hasn’t gone well over the last few weeks?    
  7. If you could start all over again how would you have done it differently?
  8. What do you want to achieve over the next couple of weeks?
  9. What would the benefits be if you achieved this goal?
  10. What do we think should be the priority?
  11. What do you think could wait while you get this done?
  12. What support do you need from me to really help you achieve success?
  13. What are you going to do next to achieve your goal?
  14. How can you use your strengths in this goal?
  15. What is working well right now?
  16. Is there something that’s not going so well at the moment? Why do you think that is? How could I help you change this?
  17. Are you getting a sense of accomplishment with what you’re working on? Why?
  18. Do you have the opportunity to do challenging things at work?
  19. Are you getting the freedom you need to control your work?
  20. Why haven’t you reached that goal already? What do you think is stopping you? What do you think was really happening?
  21. Do you know other people who have achieved that goal? What is it that they did that you could learn from?
  22. How could you turn this around this time? What are your options?
  23. What do you think you need to do next?
  24. What do you think you need to do to get a better result (or closer to your goal)?
  25. Who else might be able to help?
  26. Have a think about what you want to cover in our next check-in?

A culture of asking for employee feedback and opinions creates happier, more engaged and better performing employees. So why then do we wait to make this an annual exercise? Asking your employees for their feedback more frequently will give you quick and real-time insights that will help you develop meaningful interventions. We’ve put together some questions you can consider asking based on the four key drivers of engagement, 1) Trust me and give me flexibility, 2) Care about me and help me with my career, 3) Ensure what I do matters, 4) Give me a great line manager

Measure engagement at the job level:

  1. What is the most interesting part of your job?
  2. Do you feel excited about the work you do every day? What would make you feel more engaged in your job?
  3. In what way does your job provide you with meaning and purpose?
  4. What motivates your individual contributions?
  5. What are your strategies for achieving beyond the KPIs you have been set?
  6. Do you have the right resources to do your work?
  7. In your day-to-day work, do you feel like you are gaining valuable skills and experience that will help you in your future career? How else would you want to be developed?
  8. Do you feel appropriately recognised for a job well done? What else could we do?
  9. What’s the best thing that happened to you at work this month?
  10. Do you have a good work life balance? When do you feel like your work responsibilities interfere with your life outside work? Is there anything we can do to change this?
  11. What is one thing about your work experience that is really positive?
  12. What is one thing about your work experience that needs significant improvement?
  13. Is there anything else you would like to share that you find important to your employee experience here?

Measure engagement at the managerial level:

  1. How does your manager bring out the best in you and your team? What can they do differently to support you?
  2. Do you feel comfortable reaching out to your manager when you need their help or support? Do you feel listened to?
  3. How does your manager show an interest in your well-being? What more can they do?
  4. Do you feel like you have the freedom to choose how to best perform your job? In what ways does autonomy from your manager play into your everyday workflow?
  5. Does your manager communicate clear performance expectations of you and your team? Is there anything else we could do to help clarify your goals and outputs?
  6. Are opportunities for your growth and development discussed often with you? What else can we do to help you own your development? What role would you like your manager to play in advancing your career at our company?
  7. Are you well informed about what is happening in the organisation? How would you prefer your manager cascades company information to you?

Measure engagement at the team level:

  1. Does everyone on the team have clarity on each person’s roles and responsibilities?
  2. What do you like about working with your team?
  3. What motivates you to share your opinion at a team or office meeting? Do you feel comfortable sharing your opinion?
  4. How do you connect with other employees?
  5. How do you and your co-workers exchange learnings, experiences and challenges?
  6. How would you describe the team dynamic within your department?
  7. What motivates your team contributions and collaboration opportunities?
  8. What strategies does your team use to collaborate and maintain engagement to meet and exceed goals?
  9. How can your team help you work better?
  10. How do your team members handle opinions that are different than their own?

Measure engagement at the organisational level:

  1. How do you feel your work aligns with the goals of the company?
  2. Do you feel inspired and motivated by the vision and values of the company?
  3. Does the organisation’s mission and values consistently inspire you to do your best?
  4. What was the primary reason you accepted an offer at our organisation?
  5. Do you feel proud to work for us? Would you recommend us to a friend or relative? How would you describe us to them?
  6. What helps you to feel like you belong in here?
  7. Describe how your job explicitly connects to customer needs.
  8. In what way does leadership energise you to come to work?
  9. Name one way in which company communication could improve?
  10. Do you feel like the company celebrates accomplishments and learnings?
  11. Our organisation attracts, develops, and retains people with diverse backgrounds. Why do you agree or disagree with this statement?
  12. How would you describe working at our company in three words?
  13. What practices do we need to change or improve upon? Which rules or policies get in the way of you doing your best work?
  14. What three words or phrases best describe our organisation’s culture?

We often think about retention when someone has just resigned. Over half of all employees who are leaving, say their manager or organisation could have done something to keep them. Rather than waiting till it’s too late, there are useful questions we can ask our people to help us retain our key talent. Just sitting down with them and posing a number of key questions can help you work out whether someone is at risk of leaving, and what you can do to help them stay.

Try some of these questions when someone has been with you a short while, say three or six months. Or just cover a few of them at your next check-in.

Identify factors that make the employee want to stay such as:

(Note: this is the No. 1 key retention factor for top performers)

(Note: this is the No.2 key retention factor for top performers.)

Identify actions that might increase loyalty and commitment

  1. If you “managed yourself,” what would you do differently that I don’t currently do?
  2. Can you make a list of the elements or motivation factors in your current role that you like best and that you would like “more of”?
  3. What factors would you miss most if we transferred you to a completely different job? What things do you really miss from your last job at the company?
  4. Can you also make a list of the less-desirable elements or frustrations in your current role that you would like to do “less of”?
  5. Are there any frustration factors that keep you up at night, that enter your mind while driving to work, or that cause you to dread having to come to work at all?
  6. If you were given the opportunity to redesign your current role, can you make a list of the key factors that you would include in your “dream job”?
  7. Can you help us understand your career progression expectations and let us know where you would like to be in the organisation two years from now?
  8. Can you list for us the most challenging but exciting aspects of your current job situation? Are there actions that we can take to further challenge you?
  9. Can you highlight any recent recognition and acknowledgment that you have received that increased your commitment and loyalty? Are there actions that we can take to further recognise you?
  10. Can you highlight for me your positive experiences in the area of learning, development, and growth? And are there ways where we could increase that growth?

Identify “triggers” that may cause employees to leave

Triggers are occurrences or events that drive loyal employees to at least begin considering looking for new job.

  1. If you were to ever begin to consider leaving … help me understand what kind of “triggers” or negative factors that might cause you to consider leaving? Please include both job and company trigger factors.
  2. Think back to a time in the last 12 months when you have been at least slightly frustrated or anxious about your current role. Can you list for me the frustration factor or factors that most contributed to that anxiety? Can you also help me understand what eventually happened to lower that frustration level?
  3. If you’ve had conversations with other employees who have considered leaving or who have actually left our company, did any of the reasons that they provided for leaving cause you to at least partially nod in agreement? If so, can you list those factors and tell me why they seemed to be at least partially justifiable as a reason for leaving to you?
  4. What are the prime factors that caused you to leave your last two jobs? Are there factors from your previous jobs that you hope you will never have to experience again at our company?

Today’s flatter structures mean it’s not always possible to move up the career ladder. But that doesn’t mean everyone needs to stay in the same place. Career development today is about making the most of your team members’ strengths, giving them the chance to learn new skills and opening doors for them.

Here are some career questions coaching questions you can ask at your next check-in:

  1. How do you feel about your role right now?
  2. What do you like most about your role now?
  3. What do you need more of in your role?
  4. What would you like to be really good at?
  5. How can we take advantage of opportunities in your current position to learn new skills?
  6. Tell me about your aspirations – short and longer term?
  7. What are you going to do to reach your future aspirations?
  8. Is there anything in particular you want to accomplish in the next few months?
  9. What additional responsibilities would you be willing to take on?
  10. What stretch goal could we set you that would help you learn/develop?
  11. How can you get even better at what you’re doing now?
  12. What’s been your work highlight this month?
  13. What do you think is your biggest strength?
  14. What have you done that’s made you step out of your comfort zone?
  15. What new skills have you developed in the last month?
  16. Is there someone you would like to shadow?
  17. What makes you stay here and what would make you want to leave?
  18. I think a sideways move to … would be great for you right now. What do you think?
  19. Let’s discuss some ideas about how you might get that development.
  20. Is there anyone I can introduce you to who could help you?

Managers caring about employees’ health and wellbeing is a key engagement driver. This is not about spoon-feeding your team but making sure you create an inclusive environment where they feel they can bring their whole selves to work and feel supported to manage their own health and wellbeing.

Here are some questions you can try at one of your check-ins:

  1. Do you feel our team demonstrates a commitment to the health and wellbeing of employees? What could we do more of?
  2. Do you feel you have the freedom to adjust your work schedule to fit with your personal life? What stops you?
  3. Is there anything that I am doing/the team is doing that prevents you from doing your best work? What would you change?
  4. Do you think I encourage a balance between work and family life? What more could I do?
  5. Do you feel the demands of your workload are manageable?
  6. Do you feel that you can live a physically healthy lifestyle? What would help?
  7. When you feel stressed, what happens and how do you deal with it/how can I help?
  8. Have you got the support available at work to get help when that happens? What else could we do?
  9. Do you have somewhere you can go during the day where you can relax?
  10. You know I’m always here to listen not judge?
  11. When’s your next holiday/time off –how could we help to make it stress free?
  12. Do you prefer to completely switch off in your own time or keep in contact? How can I/the team support that?
  13. Does your physical work environment help contribute positively to your work? What could make it better?
  14. Do you find it easy to start up conversations and collaborate with others?  What would make it better?
  15. What frustrates you at work/makes you stressed? What could we do to prevent that?  
  16. Do you feel as a team we welcome different views and opinions? What could we do differently?