"Things Are Going Okay," Said the CEO Whose Business Was Flying

"How are things going?"

"It's going okay."

That was how one of my coaching sessions started recently, and with this particular business owner I'd learnt to be a little suspicious of that answer, because they have a habit of landing on the cautious read even when things are good.

As we talked it through, the picture was considerably better than okay. The business had made some bold calls that were now clearly paying off, it was growing, and some significant opportunities were starting to come its way as a result of years of hard work. By the end of the session it was obvious that things weren't going okay at all. They were going really well, even if it didn't feel that way from the inside, and I told them so.

I see a version of this more often than you might expect, particularly among ambitious leaders.

In another business, the numbers are objectively strong. It's profitable, ahead of where it expected to be and close to hitting a stretching new business target with time to spare. The CEO walked me through those results and, almost in the same breath, moved straight on to everything that still needed fixing. Delivery wasn't where it should be and quality was under pressure.

All of those things were real and worth addressing. But they were also the consequence of the business being busier than it had ever been, which is a very different story from something going wrong.

I understand why high-performing leaders do this. The ability to see the gap between where things are and where they could be is often exactly what made them successful in the first place. If you're the person who always spots what's missing, you probably built a better business because of it.

What interests me is what happens when every achievement is immediately absorbed into the new baseline.

For the leader, the finish line keeps moving. Marshall Goldsmith calls this the great Western disease, the belief that we'll be happy when we reach the next goal, and of course when we get there, a new goal has already taken its place. If your definition of success moves every time you reach it, you never actually get to feel successful, however well things are going.

For the team, the effect can be even more significant. If the CEO barely registers a good result before moving on to the next problem, people learn that doing well simply earns them more to do. Over time, success starts to feel like the absence of criticism rather than something worth recognising. Teresa Amabile and Steven Kramer's research on the power of small wins found that a sense of making progress in meaningful work is one of the strongest drivers of motivation, and that managers often underestimate their influence over it. If people rarely hear that progress has been noticed, it's easy to see how motivation can start to suffer. I've written before about the team that never drops a ball being the one nobody thinks to save, and this is closely related.

I'm not talking about a "remember to celebrate your wins" moment here. Strong leaders should keep seeing what needs to improve, and complacency is a genuine risk in any business that's doing well. The real skill is holding both pieces of information at the same time, accurately: this is going extremely well, and there are still things we need to fix.

So what helps? The simplest thing I've found is to make yourself describe the business as an outsider would, using the facts rather than the feeling. What would a board member, an investor or a competitor say if they looked at the last twelve months? Then make sure your team hears that version too, before you move on to what's next. I'm a great believer in noticing our own patterns, which is easier said than done, and I've written about my own tendency to catastrophise for exactly that reason.

None of this will make you less ambitious. If anything, it makes the ambition more sustainable, for you and for the people working alongside you.

If someone asked you today how the business is doing, would your answer survive a look at the numbers?

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.