Three Challenges for Managers Leading Career Conversations

Managers can find talking about career opportunities with their direct report colleagues remarkably challenging.

Three concerns come up repeatedly.

1. I don’t want to lose this person from my team

It can be very hard to see a great team member move on.  However much you know it is the right thing for them, it often leaves you with a problem – you are a person down, and the average performance of the team overall has probably dropped.     If your colleague has an opportunity to move on within the organisation, you may also feel ‘left behind’ in some way.  You still have to manage the same old problems, while they move into some new opportunities and challenges.    If this situation resonates for you, try focusing on the success you have had in developing your team member.

Make sure you manager knows that your colleague could move on because they are growing and developing, and you have had a hand in that.   Successfully growing team members is a skill that you will need throughout a management career, and the higher you climb the more successful you will need your team to be.   Reframe your perspectives so that you don’t see the move as a ‘loss’ for you, but as a mark of your management capability.  Other good people will want to come and work for you if they see that you will help them grow and develop.

2.  How can I advise someone that the only career option at this point is to move to another organisation?

Unless you are working in huge teams, or in an organisation with tens of thousands of employees, there will come a point where the only way for a person to move up is to move organisations.  This is especially true for people working in smaller functions, with flat hierarchies.   It can feel very disloyal to encourage a colleague to apply for roles elsewhere, but if you think that is the right solution for them, then you should support them.

In my book, The Performance Management Playbook, I share a story of a café manager whose staff were all looking for better roles with more career prospects.  Initially the manager found this difficult to cope with.  After a few months she changed her approach, and encouraged her staff to talk about the roles they were applying for and the careers they wanted to develop.  She was supportive when anyone got a job interview, and celebrated when a new career took off.  The result was a very happy work culture, with cheerful staff who felt valued, and didn’t have to hide their individual ambitions at work.  The café became one of the most popular to work for, in a town with numerous cafes, so she found it easier than most to recruit.    The moral of the tale is, act with integrity.  If you are genuinely unable to offer more development or opportunities to grow within your organisation, do not feel bad about encouraging a colleague to look for the next step elsewhere.

3. ‘I’m worried about demotivating this person because I don’t think they are ready to move on yet’

Some people arrive one day, want your job the next, and Chief Exec role the day after.   The best way to support this person is to make clear what skills and experience are required for the role they desire next, and help them reflect on the gap between what is needed and where they are.  If you keep the conversation focused on specifics, rather than de-motivating them, you can engage and enthuse them with a plan to help them move on (even if it will take several years).

Even if your personal opinion is that they will never be able to move up in the way they want, that isn’t relevant to the conversation, and you don’t need to share that opinion.  After all, it probably won’t be you interviewing them for whatever role they apply for next.  So, focus on specific development requirements for them.  You can also indicate that though at some point they may be skilled enough to move up, there is always competition for roles, so you cannot guarantee anything.


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