20 questions to ask your valued colleagues

The best new year gift to people you work closely with is a candid, courageous conversation.


Does your return to work have to signal the end of the season of goodwill? Or can the efforts you have just made to create peace and harmony at home be extended to your working relationships? Unless your business leaders have consciously reduced growth targets year-on-year or decided to take a margin holiday, your working environment is likely to be highly charged, and relationships between team members put under considerable strain.

You could be forgiven for choosing to keep your head down and keep your own counsel. You may be tempted to smooth over disagreements to keep the peace. In so doing, unintentionally, you could be contributing to a toxic culture in which relationships lack authenticity, things that need to be said are left unsaid, and ambiguity prevails.  Worse is to follow in the form of decision paralysis, resentment and disengagement.

So make it a priority at the start of this new year to improve your working relationship with at least one close colleague – perhaps even the one you find most challenging. I have come up with 20 questions to put to them. This isn’t a challenge for the faint-hearted. Some of the questions may even make you cringe as you ask them or wince when you listen attentively to their answers. Embrace this exercise, act on what emerges and it will set both of you up for a more fulfilling and successful 2020. 

The questions assume a stereotypical relationship between a line manager and a direct report As I discovered when researching my book Consiglieri: Leading from the Shadows, relationships among colleagues are contextual.  Enlightened managers are more like coaches and many direct reports contribute to their line manager’s leadership. So adapt this guide to suit the quality of relationship that you already have, whether line manager to direct report, coach to player, or peer-to-peer.  

In the conversation, commit to give each other your undivided attention. No sudden ringtones, no wrist vibrations alerting you to stand up or breathe deeply, no filling the pauses that might follow your searching questions. Yell with your silence. Be present. Show a genuine curiosity to unearth what your colleague truly cares about. Sprinkle the conversation with open questions and language that will drive more insight: ‘tell me more’, ‘why is that?’, ‘have I understood correctly that…?’.

The first three questions encourage the person to share how they feel about the year that’s just ended. Questions 4 and 5 explore your respective purposes – what you do, why you do what you do, and the values that guide your choices, actions and interactions. Questions 6 to 10 are about how you collaborate. Questions 11 to 16 are about how you communicate and create. Question 17 is about growth and development, and questions 17 to 20 wrap up and let you end on a positive note.


  1. What was the highlight of 2019 for you personally? Tell me more… (If your colleague signals some reluctance to answer this question, take it as a signal that they value their privacy, or that they do not wish to reveal too much about themselves until you get to know them better)
  2. What was the highlight for you professionally? Why? (Follow up: A - Interesting. That is exactly the highlight I identified about you. Or B - Interesting. I had identified a different highlight which is….). 
  3. What, specifically, did the business do last year that made you most proud?
  4.  What did I do last year to help you advance your personal purpose?(If they have never shared this with you, now might be a good time to probe what your colleague’s hopes and aspirations are, not just for the year, but for the next three years. If you’re talking with your direct report and they are unclear about their purpose, encourage them to reflect more deeply and to take responsibility for their own happiness and wellbeing. If you’re talking with your manager, explain to them that you wish to support and contribute to that which is most important to them, knowing that your own advancement will be tied to the strategic value you provide the business and your leader’s own contribution to it.)
  5. Inspired by your personal purpose, and knowing what matters to our business (if you have not shared the priorities of the business, now is the time), what choices have you made/can you make about how to spend your time and energy this year? (To your manager, you might want to add: and where would you therefore wish me to focus my time and energy?)
  6. What might I have done last year to hinder your progress? When, for example, did you return home squeaking about an injustice I had committed, an offence I had caused, a moment I had missed? Which of my idiocies or idiosyncrasies could you not wait to offload on your partner?
  7. What could we do this year to ensure that the next time I do not live up to the expectations you have of me, or the commitments we have made to each other, you feel okay to tell it to me straight instead of having to bottle it up or offload on your partner?
  8. On a scale of 0-10, where 0 is ‘we are hopelessly dysfunctional’ and 10 is, ‘we are beautifully in sync’, how well do you feel we are working together?
  9. So, what would it take from me to help get us to the perfect 10?
  10. 2020 is a movie about us at work. What is the movie called and why? If you are to be my Best Supporting Actor, who should we cast? Who would you cast as me so that we both win an Oscar for our respective roles?
  11. Is there anything in the way I communicate with you that, specifically, you find helpful or that really frustrates you? What existing or new routine would you find it helpful for us to maintain or create to drive the most effective communication between us?
  12.  For the good of my performance and the business, I hope we disagree often this year. How can we use these disagreements to our advantage and resolve those that may inhibit our progress? If you’re talking with your manager, you can say you know they are allergic to sycophants, so you really want to know how they prefer to hear, ‘no’
  13.   When might I have killed a great idea you had or inhibited your creativity? How can I help foster the environment in which you can develop   your most audacious thinking? As the direct report, you might ask, ‘when did I fail to spot the genius of an idea you had, or failed to implement it with enough enthusiasm?’
  14.  What aspect of your performance would you most like to develop and improve this year? And, if you want clear direction from your line manager, ‘What aspect of my performance do you think I would benefit from improving this year?’
  15. As the line manager, you could follow up with, ’how would you like me to support you in that development, or is there another aspect of your performance you would like me to help you with? As the direct report, your way into development could be, ‘If you were in my shoes, how much room for improvement is there and what support might you be prepared to give me to achieve that improvement?’
  16. What, concretely, can I do to foster your potential to perform at peak consistently? The direct report may wish to push further: ‘what, concretely, can I do – or stop doing – to foster your own desire to perform at peak consistently?
  17. What new experience or opportunity would you value next? What project or initiative do you have your eye on? If it can be arranged, where in the company and on what kind of work would you most like to spend time? Can you think of a colleague in a different function who would value a swap over a short period of time? (As the direct report, you should be thinking about stretching yourself with a new experience or opportunity and asking your manager to explore that possibility together: ‘What would you need me to do to make you feel rock solid secure that, if we can land that project/opportunity/experience in a timely fashion, you continue to get the 100% support and commitment on the priorities that matter most to you?’
  18. If you have one piece of advice to give me that will ensure I can be the best version of me at work in 2020, what would it be?
  19. What have we left unsaid that we really should have brought to each other’s attention?
  20. It’s December 23, 2020. As you leave the office for Christmas, what accomplishment will you reflect on?

Finally, don’t wait until next year to gift a candid, courageous conversation to more valued colleagues. This guide can be the gift that keeps on giving.

Richard Hytner SLN 2002/3, Adjunct Professor of Marketing, teaches on SEP, Strategic Branding and Market Driving Strategies Programmes at London Business School where he also runs an elective on Creativity in Business; and is the founder and CEO of beta baboon.

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