If You Won Your Biggest Deal Tomorrow, What Would Break First?

I found myself asking almost the same question in three completely different businesses last month, and it wasn't how they were going to win more work. It was what would happen to the business if they did.

That sounds like a nice problem to have, and in many ways it is. But the more I've thought about it, the more I think a lot of growth plans have a gap in the middle of them. We spend a great deal of time working out where the revenue will come from, which markets, which contracts, which customers, and much less time working out what the organisation needs to look like to deliver it.

The first conversation was with a leader whose business has the chance of winning a game-changing contract. Naturally, most of the energy had gone into how to win it. What we ended up talking about was what the team would need to look like if they did, where those people would come from and what capability needed developing before the work arrived. Once a contract like that is awarded, there usually isn't much time before the work starts, and certainly not enough to build a team from a standing start. The thinking has to happen now, while it still feels a little premature.

The second was a leadership team session, and they arrived at the same place on their own. The business has a clear growth strategy and a pipeline that's building nicely, but as we talked, it became obvious that the people strategy hadn't kept up. Several senior people were regularly stepping down to do work that belongs to the roles beneath them, because the people in those roles weren't yet able to make the decisions the job requires.

What struck me was how neatly that problem protects itself. The leaders don't have time to build a people strategy because they're busy doing work below their level, and they're doing that work because there isn't a people strategy. Breaking that loop starts with someone protecting the time to plan, even when the day job is full on.

I asked them, if the business didn't exist and you were setting it up from scratch today, how would you structure it? That led to something I didn't expect. The team realised that with the right people in the right roles, they might not need to recruit as many people as they had assumed, which is a very different conversation from simply adding headcount.

These were very different businesses, but the conversations were circling the same issue. Growth strategy tends to be exciting, so it gets the attention, while the organisational consequences feel much less interesting until they suddenly become urgent.

Jim Collins made a version of this point years ago with his idea of "first who, then what", the argument that great companies get the right people in place before deciding exactly where they're going. In the SME world I'd put it slightly more practically. If your people planning is falling behind your growth plan, you'll end up recruiting in a hurry, promoting people before they're ready or asking your most senior people to carry the gap themselves, and none of those is a great place to grow from.

There's also a reason to be thinking about this now. From 1 January 2027, the qualifying period for ordinary unfair dismissal falls from two years to six months. Anyone who already has six months' service at that point will gain that protection immediately, so for employers recruiting now, the window for finding out whether someone is really right for a role is becoming considerably shorter.

So what does running ahead of growth actually look like? I'd start by working backwards. Picture the business when the pipeline lands, decide what the team needs to look like to deliver it, and compare that with where it is today. Then ask three questions. Who is ready now? Who could get there with the right development? And where will you need capability you don't currently have? That third question is the one that opens things up, because the answer might be recruitment, but it might equally be restructuring, technology, changing who is responsible for what or developing someone in a different direction.

It's also worth asking what would break if things went better than planned. In another business I work with, we spent time on where a new product launch would break if it went wrong, and then on where it would break if it went too well, which turned out to be just as revealing. A pre-mortem is a simple way to do this as a leadership team, and it tends to surface the capability gaps nobody has raised yet.

None of this means slowing down the growth plan. It means giving the people side of it the same seriousness you'd give a major contract, because in the end the people are the ones who'll deliver it.

If you won the biggest opportunity in your pipeline tomorrow, what would break first?

If you'd like to think this through for your own business, you can find out more about how I work with CEOs and leadership teams.

Nicola Gunstone is an executive coach working with CEOs and MDs of growing businesses. If this struck a chord, you can connect with her and follow the conversation on LinkedIn.