Something came up in a coaching conversation recently that I think will be familiar to quite a few business owners.
We were talking about a piece of work that had become more difficult than expected.
That in itself wasn't really the issue.
These things happen.
Projects change, assumptions turn out to be wrong, customers move the goalposts and sometimes something simply takes longer than you thought it would.
The problem was when it had become clear.
Or, more accurately, when it had been communicated.
By the time the difficulty was properly on the table, the deadline was close enough that there weren't many options left.
And I think there's quite an important distinction there.
I can deal with bad news.
What I find much harder to deal with is bad news that arrives too late to do anything useful about it.
If you tell me three weeks out that something is slipping, we can have a conversation.
Perhaps we need more resource.
Perhaps the deadline needs to move.
Perhaps the scope needs to change.
Perhaps somebody else needs to get involved.
I don't necessarily know what the answer is yet, but at least we have choices.
Tell me the day before the deadline and most of those choices have disappeared.
The conversation then becomes less about solving the underlying problem and more about managing the immediate consequences.
I've seen this happen in lots of businesses, and I don't think it's usually because somebody has deliberately hidden something.
Quite often, they genuinely think they're going to sort it.
They don't want to bother the boss with a problem they might be able to resolve themselves.
Another day passes and they think they're nearly there.
Then another.
Eventually the point at which they could have asked for help has passed and the problem has become much bigger than it needed to be.
Which made me think about the owner's role in all of this as well.
It's easy to say, "Why didn't you tell me?"
But perhaps there's another question worth asking.
Why didn't they feel they could tell me?
Maybe nobody has ever made it clear when something should be escalated.
Maybe the culture rewards people for sorting things themselves but doesn't make enough distinction between taking ownership and struggling silently.
Or perhaps people have learned that bringing a problem to the owner isn't a particularly enjoyable experience.
That's an uncomfortable one, but it's worth considering.
If every time somebody tells you something has gone wrong your immediate reaction is frustration, interrogation or jumping in and taking over, you can't be too surprised if people start waiting until they're absolutely certain they need to tell you.
You can accidentally create exactly the behaviour you're complaining about.
I think good management needs to make room for people to say, "This isn't going the way we expected" before they necessarily have the answer.
That doesn't mean escalating every minor difficulty. You don't want a team that brings every problem straight back to you without thinking through the solutions either.
It's about knowing the difference between something they should own and something the business needs visibility of.
And that probably needs a conversation before the problem happens, rather than afterwards.
What are you happy for people to resolve themselves?
At what point do you want to know?
What would make something worth escalating?
If everyone has a different answer to those questions, you'll eventually get a surprise.
So perhaps the next time somebody brings you bad news later than you would have liked, don't just ask why they didn't tell you sooner.
Ask yourself whether you've created a business where telling you sooner is actually the normal thing to do.
Because problems are inevitable.
Surprises at the deadline don't have to be.
If this has you wondering whether your business has the right systems, people and accountability in place to spot problems before they become emergencies, let’s have a conversation.
Book a FREE Growth Strategy Session and let’s look at where your business could be working better.
P.S. If you're curious about your own business strengths and where there might be some blind spots, take our Business Superpowers Scorecard. It takes just a few minutes and might highlight something you hadn't considered.
