Mini Conversation Guide – Career Development for Your Team


Imagine this… You might have 5 people reporting to you. You might have 3 or 2 or just one. Your team performs reasonably well. You have one person who you can always count on, works themselves to the bone. Although you are concerned about them burning out. You have another team member who is very, very clever. They could be doing anything they wanted. The problem is application – is their heart really in this role or somewhere else? There are lots of different varieties of people, each of us is incredibly complex. But one thing stands out as a common factor for all of us in any team working in an organisation – we all need some idea of the future. Therefore, if you manage people, you need to think very carefully about the aspirations and ability of the people in your team. If you can provide a way for people to talk about their future in a safe way, and you help people to realise at least part of that future in your organisation, you’ll be amazed at the results. The starting point is a good conversation. What you need:

  • Trust
  • A quiet and private place where there’ll be no distractions
  • A strong desire and the ability to continue supporting your team member reach their goals

Some questions that may help the conversation:

Why are we here? Make sure you are both clear on the purpose of the conversation. If you don’t believe it, neither will they. So dwell on this question – why are you bothering to do this? If you don’t have a good answer – DON’T DO IT!

What gives you the most energy in this role? What gives you the least? Now a lot of people will say – don’t ask that, they’ll complain about things they HAVE to do and you won’t be able to do anything about it! There are always things we have to do in our roles that we don’t like. I once had a job where I was essentially managing a small office – from processing accounts, to the website, answering the phone and booking appointments. Some of it was awful, some of it I was surprised that I enjoyed. The idea here is that you are trying to help someone be “In Flow” for as much time as possible in their role: where they are doing work that they enjoy and are challenged by (that’s not the definition of In Flow by the way – I’m paraphrasing because true “flow” can seem a bit unrealistic at work – but it’s a helpful model to help someone understand the work they enjoy in their current role).

What is your career purpose? In other words, why are you working? What’s the point? For many people this is for material reasons, for others it is about supporting other people e.g. “to help support my family”. It could be focused on career advancement in their profession, “to be the best teacher I can be”. Or it might be about broader, more esoteric objectives e.g. “to help build a strong community”. It is a revealing question – a lot of us can’t actually articulate it! Which is why having you – their manager – ask them might be just about the best thing that’s happened in their career all year. What can we do together to help you achieve your goals?

  • Hopefully, if you make some progress on “purpose” then there will be some idea of goals. In my view, goal-setting needs to be approached with extreme caution, particularly when it comes to careers. Sure, plenty of concrete, achievable things can be worthwhile goals, but a person’s career pathway can change so quickly that goals can become redundant and an irritation rather than the impetus to achieve things (which is what they’re for).
  • One way to approach this is to say “Look, these are your goals and your goals only. Even with the best intentions, some goals can become less important and new ones arise. I’d be happy to revisit any or all of these with you as we go along.” And don’t bother holding someone to account for their own goals either – they’re not your goals and you aren’t assigning them as work to do. This is about individual development in the context of work in your organisation. Don’t take all the enjoyment away by insisting they be completed. Few adults will thank you for doing that.
  • *And don’t get sucked in by “I want you (my manager) to tell me what to do” either – this might solve a few short term problems but challenging people to take responsibility for their own development is what this is all about.

Some final things to think about: What if I get an answer from my team member that I don’t like e.g. “well, I don’t actually want to be here”? If that happens, it is a good thing. Why? Because the team member you have probably been concerned about is finally opening up and telling you the truth. Now, if that conversation hadn’t happened “the truth” may have come out by that team member resigning suddenly over a holiday break, never to be seen again. You’ve now got the chance to talk about why. What’s going on for them? What can be adjusted to help take some of the pressure off (anything?). It may be a lost cause, but at least you’ll have the opportunity to learn a new perspective from a team member. A skill all leaders must cultivate!

*You might be interested in our other posts on career development across a range of topics including: