Retain team members - or not

Disclaimer: This is not a how-to on how to retain team members by giving them free coffee or other gimmicks like that. It’s not even about retaining at all cost.

Many years ago I worked for a small company that was bought by Microsoft.
One day we had an employee survey - one of the questions on it was “Do you intend to work for Microsoft until you retire”. Most of our newly-bought business said no and, predictably, we had a report back from corp that highlighted this as a potential morale problem in our area. I, and most of the team, disagreed. In our minds, having most of the team saying that, yes, they do want to stay in the same company until they retire would have been a serious concern that something was wrong.

The relationship between an employee and their manager is in part a human-to-human relationship and a lot of the same emotions go into it as in any other such relationship, including feelings of loyalty, expectations, betrayal and so much more.
For most employees, it can be emotionally hard to actually hand in their resignation (no matter whether they like their manager or not) and for most managers it feels like a body blow to receive a resignation letter.

Whether you hate each other or have a great working relationship, it still feels like leaving a partner with all the emotional baggage that comes with that. On top of that, from the managers point of view, there are all the additional concerns, such as losing the skills of the team member, having to recruit and worrying about what their manager will think of them for “losing” an employee.

It shouldn’t be like that.

Another way to think about it

We are all part of each other’s journeys.

When someone works for me, I think of it as a time-limited, mutually beneficial relationship. While that person is working for me, I’ll expect them grow and learn, developing both themselves and their career. My job as a manager is to support that growth and that journey whilst making sure the company benefit from what that person brings. There is a balance to be achieved there; companies are not charities and need to get value from the people who work for them. At the same time, though, helping a person grow helps retain them (at least for now), helps them add more value and - crucially - helps attract new talent to the organisation.

Eventually, that person will want to take their career in a different direction - or there may simply not be an opportunity for them to continue to grow in my organisation. There can be many reasons for this, all dependent on the team member’ s abilities and aspirations as well as my company’s particular situation and needs. At that point, it doesn’t suit either me or the team member for them to stay; they’ll be unhappy that they are not doing what they really want and I will be perpetually worried about losing them as well as constantly having to deal with them being unhappy.

When you get to that point, it is much better to agree that it’s time to move on and work on it together. For me, it’s always gut-wrenching to lose a team member, but I am also always very happy to watch them succeed in other places, especially when I feel I had some role in helping them on their journey.

The horrible situations are the ones where you can provide the journey the person is seeking but they didn’t realise. Then you lose a valuable team member for no reason - and they miss out on the opportunity to keep growing, quite possibly faster, in an environment they already know.

What we should do

I’ll be the first to say that I am not great at applying this consistently - this is what I aspire to do. As a teacher once said to me; Do what I say, not what I do ;)

  • Make sure it’s understood in your organisation that you can have unemotional conversations about career development, including conversations about moving on, without fear.
  • Have clear and regular conversations with each team member about what their aspirations are and how you can help them get there. Or explain why you don’t think they can get there, whether that’s to do with their abilities or the constraints of the organisation.
  • Put measurable, actionable plans in place; This is where I fail most often. It’s relatively easy to have the conversation but converting it into a plan with dates and milestones that you can hold each other accountable to is hard work.
  • If someone does resign unexpectedly (or you are afraid they might) - have the conversation about aspirations and options. If there is room for accommodating their journey within your organisation and it fits - work really hard to retain them. If, on the other hand, you can’t see a meaningful journey for them, just end it there; It’s counterproductive to make them stay just to avoid a short-term problem.
  • Don’t ever let yourself fall prey to “I can’t afford to lose that person from that role so I won’t move them to some other role”. If you do that, you just ensure they’ll leave your organisation altogether.

A place for “just doing my job”?

My whole argument here is based on the idea that everyone has to continually grow and change throughout their career. But what if you just want to continue doing the same job until you retire? Honestly, I am biased because in the industry I work in, both individuals and organisations have to continually renew themselves. 10-year old skills are rarely marketable in this industry (with some notable and extremely valuable skills - but even those are not what you want to build your retirement plan on).

Do those jobs still exist in other organisations? Maybe… I think the world is now changing so fast that very few jobs can be expected to stay the same over any 10 year period. I do think this will be the cause of considerably social anxiety and disruption, but that’s a discussion for another day.


It’s a shame that it is so hard to have these conversations in practice. Thinking about leaving a job is uncomfortably like thinking about leaving your partner. You probably wouldn’t have a chat with your spouse about whether it would be best to split up unless you are already pretty sure that it is. But working relationships are not marriages. You should explicitly expect them to end at some point.

You are part of each others journey for a while, both sides benefiting from the relationship both in terms of money/work and in terms of personal/organisational growth.
If we can separate personal relationship and the feelings of personal loyalty and betrayal from the conversations, then I think we would all be better of.