What if you weren't here tomorrow? The uncomfortable conversation every business owner needs to have.

It's not a comfortable thought, and I understand if you would rather skip past it. But it is the question that stayed with me long after our board meeting last week, and I have decided it's worth sitting with rather than avoiding.

None of us are planning to go anywhere. That's not the point. The point is that most of us, if we are really honest, have never properly dealt with the “what if". We're too busy running the business to stop and imagine it running without us.

So let me ask you the same question I have been asking myself: if you weren't here tomorrow, what would happen to your business and to the people who depend on it?

What if you weren't here tomorrow?

The business side

Start with the most basic question of all. Who would drive the business forward? And just as importantly, do they know they are the one?

It is easy to assume someone would step up. A partner, a senior manager, or a family member could be the one. But an assumption is not a plan. Have you actually had the conversation? Are they willing to take it on? Are they capable, and do they have the skill? Being trusted and being ready are two very different things.

Then there are the practical realities that bring a business to a standstill faster than anything else:

• Who has access to the business bank account?

• Do they know where you keep the contracts, agreements and important documents?

• Do they understand your systems and processes well enough to keep things moving?

• How would your staff, your clients and your suppliers hear the news, and who would tell them?

That last one matters more than we tend to think. The way something like this is communicated, and how quickly, can be the difference between a team that holds together and one that quietly falls apart. Your clients and suppliers are affected too, and how they are handled in those first few days shapes whether the business they built with you survives the shock.

What if you weren't here tomorrow?

The personal side

The personal matters are just as heavy and often even more neglected.

• Is your will up to date, or is it a document you signed years ago and haven't looked at since?

• Who holds power of attorney?

• Is your insurance actually enough to protect the people you love, or is it a policy you took out long ago and never revisited?

And then the small, ordinary things that turn out to be enormous: Do the people who would need to step in even know where your passwords and key information live?

So much of modern business and modern life is locked behind a login that only you can access.

Start a “life file”

I've started thinking of the answer as a “life file.” One place, kept up to date, that holds everything someone would need to either keep things running or wind them down properly, if you couldn't be there to do it yourself.

Your will and estate details. Your insurance. Your passwords and access information. Where the contracts and documents are stored. Who has authority to act, and who you'd want to succeed you? Your wishes, written down, so the people left behind aren't forced to guess at them in the middle of their grief.

It also includes the conversations. A life file on a shelf is only half of it. The person you are counting on to lead needs to know they are being counted on and needs to have agreed to it, while you are still here to talk it through with them.

Why we avoid it, and why we shouldn't

None of us want to think about this. That's exactly why so few of us have. It feels morbid, it feels premature, and there is always something more urgent demanding our attention today.

But avoiding the conversation doesn't make the risk go away. It just leaves the people who depend on us, our families, our teams, our clients, to face the hardest possible moment while also scrambling to work out how anything functions. We owe them better than a scramble.

As business owners, we spend so much energy protecting what we have built. This is simply the part of that protection we tend to leave out.

So here's my honest question

If it happened tomorrow, would your business and your loved ones be okay?

If that question makes you even a little uneasy, take it as the nudge it's meant to be. You don't have to solve it all at once. You just have to start the file and start the conversation.

This week feels like a good week to begin.