Letting People Go
Learning to let go is an essential skill as you scale and grow.
I used to feel a real sense of hurt when people left our team or community.
I remember when members used to leave ICE it would feel like that was it. Once one had left it would be the watershed moment and everyone would go.
It was even worse if someone decided to leave our team.
The very idea that they could thrive in another environment felt like a comment on how bad ours must be.
Learning to let people go was a skill I didn’t realise I had to develop.
Failed leadership
This old feeling was one of failure. That I’d not seen it coming, that we were not an essential part of their lives.
How can a leader trying to create a welcoming environment for coworkers and a great team for colleagues fail to see why people would want to leave and be helpless to do anything about it?
In time, I’ve been able to see a new perspective on this, which means I get less stressed out but also that feels more reflective of the truth.
Is it definitely true?
Firstly, there’s simple mental health check-in trick that I’ve used time and time again and which helps here.
Whenever anything is feeling overwhelming, all encompassing or invasive as a thought or idea can often do (for some of us), I ask myself a couple of questions:
Firstly, I ask is it true. To which my mental response is “of course it bloody is otherwise why would I be worrying?”
Then, the second question: “Is it definitely true?”
That’s a harder question to answer, and when being honest there’s often a bit of: “well, no, I don’t know that it is definitely true”.
That’s where the light gets in.
Anyway, that’s how I started to rethink my relationship with people leaving and why I now think it is important to let people go and see it as a positive step.
Letting People Go
This new feeling has a couple of elements:
People outgrowing you
People needing to go
People coming back
And the worst case scenario
Next steps
If you are focused on growing people then you can take joy in them being ready to move to the next level.
When someone outgrows you it should be a moment of celebration.
I’ve written previously about the old cliché:
“What if we train them and they leave?”
“What if we don’t and they stay?”
There’s something validating in giving someone a platform and seeing them get the recognition they deserve.
This is especially true for me when we have someone who has joined us either from a totally unrelated industry and who has now made a name for themselves, or someone who was feeling rudderless before they joined.
It is hard to not feel the feelings of abandonment and questioning loyalty, but those are fleeting feelings, and not true.
It is something to take pride in, developing people to the next stage. And if they have a good reputation with a new potential employer then it would suggest they’ve done a good job for you too.
In our industry especially this has been hard given that we’re rarely hiring people who have done the job before, and chances are they’re not going to do the exact same job after they’ve moved on.
I personally feel it’s a civic duty to create opportunities for people to shine, but I recognise that varies based on your world view.
There’s a sense of momentum to some of this stuff. When you have a couple of folks leave all at once you panic that people will think it’s rats leaving a sinking ship, but more often than not it’s just bad timing.
Of course, the momentum can get out of hand, but this is again where that previous mental health exercise comes in handy.
When it feels like you’re in the darkest moment it often means dawn is around the corner. Don’t assume that to be the case though, life doesn’t always honour metaphors no matter how snappy they are.
Perspective helps, and when one person moves on it can create an opportunity for someone else to step up, or for new ideas and experience to join the team.
People needing to go
Sometimes people need to go, and sometimes that rests on your shoulders to make it happen.
I’ve struggled with this over the years, but recently Dan Kieran’s excellent Do Start put it in the specific context that I needed to make peace with this challenge.
Radiators and drains are two ways to describe employees. The radiators create the warmth, they’re optimistic, loyal, and willing to do what it takes.
The drains suck the energy out of the room, they’re not shy to tell anyone who will listen what’s wrong and rarely take the positive side.
You want to help the drains, or at least I always feel I do. It feels like a challenge to take on to turn them around or help them to develop.
It’s even worse when they were once one of your best radiators, and then the magic goes. You know that person has to be in there somewhere, but one day you have to accept they’re not coming back.
We had an incident recently which had a big dollop of sunk cost fallacy in it too. After committing so much to that one person you want to see it come good in order to validate your decision to go with them.
Sometimes you have to be honest when it isn’t working and realise how beneficial it is to everyone if you give them the opportunity to move on.
That’s the important conclusion to this in Dan’s book. It isn’t the person who is the radiator or drain but the situation. A drain is just the wrong person in the wrong job, company, team, or moment.
You can help them by moving them on, because chances are they know they’re not happy or fitting right, and by freeing them to a new opportunity they can gain a lot more joy in their life.
Where this goes wrong is if you don’t deal with the drains quickly enough, and then you lose good radiators who don’t stand for it and are very welcome elsewhere.
If you get this right, you can ensure that you’re not leaving on bad terms, and also realise that you can’t get those wasted months or years back.
Work takes up too much of our yearly lives, don’t let it waste away in this way.
People coming back
In time you start to see the boomerangs, the ones who needed to leave before coming back.
We had this a lot with members who didn’t necessarily recognise all the intangible value of being in the space until it had gone.
There’s a similar situation for team members though, and leaving the door ajar for a future comeback.
It’s essential to always part on good terms. Make peace, don’t take it personally. And in my opinion never attempt to mediate after the event.
If you can leave things open then you have the opportunity to bring someone back with a lot of embedded operational expertise at a time that you might really need it in the future.
A lot of people don’t believe in going back, but I think that’s often a load of rubbish (I might be slightly biased here by seeing Thierry Henry score in an Arsenal shirt in 2012 on his return).
Steve Jobs is the best example of how sometimes you need distance and a change in order to gain perspective and come back stronger.
There is a slippery slope here to creating a closed shop to trusted friends only, but when trust is such a vital quality in a team it’s easy to see why nepotism persists.
And the worst case scenario
Sometimes people leave for the saddest reasons sometimes for the happiest. We’ve had our fair share of both of those.
This month, we’ve had one of the hardest things happen that I’ve ever had to deal with in what I thought was already quite a comprehensive decade of running our business.
One of our team members passed away unexpectedly and it hit hard.
The challenge as a leader is you feel an obligation to do all the expectation management around capacity and everything like that, but it all pales in comparison.
Especially when you’re trying to build a team of people you like and whose company you enjoy.
I’ve mentioned before about the resilience of people, especially when they’re going through unimaginable suffering in their personal lives.
When writing things like compassionate leave policies it can be impossibly hard to strike the balance between fair and firm. It isn’t financially sustainable for a business to give everything, but it isn’t emotionally sustainable to rush people back.
Sometimes the things that happen in people’s lives change their ability to be in your team. Some things are positive and some are negative, like having new childcare responsibilities or caring for a loved-one who has just had bad health news.
You don’t want to put people in a place where they resent the work because it is taking them away from more serious responsibilities.
One thing I’ve learned as we’ve scaled is that keeping the whole business on the right track as junctions emerge, wheels fall off, and you’re running out of fuel becomes a much bigger part of the job, but it’s also so much more satisfying when you get those decisions right and - maybe stretching the metaphor - reattach a new wheel without losing pace.
A lot of this comes down to trying to lead with empathy, but there are lots of folks who will tell you that you need to draw a line somewhere.
As a leader of a business, your one job is to ensure that the company perpetuates.
Whatever your experience is when the time comes to let people go, don’t take it personally.
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