One late start isn’t a problem.
One missed deadline isn’t a problem.
Giving someone a bit of leeway because they’re having a crap week isn’t a problem.
The Nice Boss Problem starts when temporary exceptions slide into becoming the normal way things work because nobody ever resets the expectation.
And that can look like:
Letting lateness slide because you know they’ve got a lot going on.
Quietly fixing someone’s work instead of telling them it wasn’t good enough.
Moving a deadline because they didn’t get it done.
…then moving the next one too.
Not mentioning the thing that annoyed you because you don’t want to make a fuss.
Giving someone “one more chance” without actually telling them it is one more chance.
Avoiding a conversation because they’re having a difficult time personally.
Allowing one person to work differently to everybody else without ever explaining why.
Taking work back because it’s easier than asking them to do it properly.
Letting the loudest person in the room dictate what happens because challenging them feels exhausting.
Saying “it’s fine” when it isn’t.
Saying “they know” when you have never actually told them.
Hoping they’ll notice.
Hoping they’ll improve.
Hoping someone else will say something first.
None of these things makes you a terrible manager. I’m not calling you out on any of this.
Most of them probably come from a decent place because you’re a nice person.
But enough small exceptions left hanging around for long enough start to create a completely different set of rules from the ones you think you have.
The trouble is, everyone else can see them and that’s usually where the trouble really starts.
The person who always turns up on time starts wondering why they bother.
The person who does their work properly gets fed up of picking up someone else’s mess.
The manager gets more and more irritated, while continuing to say absolutely nothing useful about what’s actually bothering them (at least until they get home and then let all that steam off onto their significant other!).
And the person at the centre of it all carries on as normal because, from their point of view, nobody has told them there’s a problem.
That’s the bit I think nice bosses often miss.
The small thing itself usually isn’t the issue.
The issue is what happens when you let it become the pattern.
At some point, somebody has to reset the expectation and the longer it’s left, the harder this becomes.
You don’t need to turn into a raging dictator.
You don’t need a formal warning every time somebody is five minutes late.
But you do however, have to be willing to say, “Hang on, this was meant to be temporary.”
Or, “This keeps happening.”
Maybe “This is what I need from you.”
Perhaps “This isn’t working.”
That’s management.
And this is not you being difficult, or mean.
Because avoiding it usually makes things harder for everyone.
I’ve been thinking a lot about this lately and I’ve started calling it The Nice Boss Problem.
I’m also starting to wonder whether there’s something useful I could build around it.
If any of this feels horribly familiar and you’d be interested in hearing what I come up with, you can add your name here.