Leadership – How to Discuss the Future with Your Team

work colleagues in discussion in team meeting
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Employees are keen to engage in dialogue about their future as most people want some sense of direction. But while team members want these conversations, often their leaders are dreading them. Here are some guidelines to help frame the discussion.


People are craving better conversations about the future and line managers need to be ready to engage in these conversations.

In volatile times, they may want reassurance about their employability, information to help them to make decisions and to understand what options may be open to them. In the broadest sense, they want to know what career opportunities may emerge and what they can do to be ready for these openings. It isn’t just ‘high potentials’ who want this dialogue about their future – most people want some sense of direction. But while team members are wanting these conversations, often their leaders are dreading them

Why do leaders find these conversations difficult?

Many things can get in the way. For example, what happens if you tell someone you can’t meet their aspirations – surely, they will leave? What if their aspirations are way beyond their capability, how can you tell them but keep them motivated? How can you talk about long term development when all of the focus is on achieving your short-term business imperatives? How can you engage in a much more personal conversation when you normally just discuss business or technical matters? These are genuine concerns, but as a leader you can’t afford not to have these conversations. If you don’t talk with people about their future most will assume there are no opportunities for them – and become disenchanted and leave.

So, how can you start this type of conversation? How can you take the initiative and control the conversation so you don’t get caught off-guard? A generic ‘what do you want from the future?’ doesn’t really work as many people are quite confused and inarticulate about this – they need help to develop a sense of what they want. Our research shows that great conversations are a combination of exploring and informing. Exploring the individual’s hopes, aspirations and wishes, helping them to develop greater clarity, combined with informing them of likely business changes and needs. Armed with these insights you can be a ‘broker’, finding the common ground which meets the needs of both the individual and the organisation.

Here are some questions that we find helpful when exploring what someone wants:

  • What do you find most exciting in your current role – the bits that really energise you?
  • And what do you find most dull?
  • Thinking forward, what would you like to be doing more of or less of over the next few years?
  • What strengths do you have that could be better used in your role?
  • What would you like to get better at or to excel at?
  • What does career success mean to you in terms of status, job interest, contribution, team…?
  • What holds you back from making the moves you want to make?

And here are some things you can discuss when informing about possible business needs and changes:

  • Possible changes in the business over the next few years (markets, skill requirements, technology, customer needs…)
  • The skills and experiences likely to be most important in the industry/function
  • Ways in which this person’s skills could be used in different parts of the business
  • Ways the current role may evolve

This information can lead to great insights:

  • What are the short and long-term options to match personal aspirations and business needs?
  • How can you work together to move this forward?

People really value these conversations. It shows that you care. It shows that you’re interested and committed to helping them. It is hugely motivational and for many it will keep them working with you.

You can have this type of conversation with your team on a regular basis - it doesn’t need to be part of a formal company-wide process, it’s just part of great leadership.