Have you become the chief worry officer?

Back in the early days, even making payroll was merely a common stress that you didn’t have time to worry about; you simply found a way to get through. But once your business reaches a point of stability, it’s easy to find yourself worrying about more distant threats: Does my team treat customers the same way I did when we first started? Are my salespeople looking hard enough for customers? Do we really need to make those technology investments my CTO keeps bugging me about?

Congratulations. Worrying about these things means your business finally has a future to worry about. And since most founders have their net worth wrapped up in their business, you should be worried. But beware, this is often the stage in which the company loses its chief executive officer and gains a chief worry officer. You can try to hide it, but it’s written all over your face, and your team talks about it when you aren’t around.

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How can you tell if you are the CWO? You start running your company differently, playing “not to lose” rather than playing “to win.” There are subtle shifts — delaying key hires because you don’t want to disrupt the team dynamic; foregoing important investments because you don’t want to spend the money; caring more about the annual cash distributions than the value of the company. You won’t see any negative effects in the short term, but this is when most companies start to plateau, only to start rapidly losing value in the years that follow.

How can entrepreneurs break out of the CWO funk? Over my career investing with founders, I’ve discovered that you need to revisit four things if you find yourself in this common slump.

Tone. A key factor in any company’s success is the tone established from the top; if you’ve slipped into the CWO role, refreshing your tone is more important than ever. I’m not suggesting that you get a personality transplant, but your team has to feel renewed passion, see your willingness to take (calculated) risks, have the approval to spend a little money testing a few new ideas, and feel confident in your ability to handle some failures along the way. It doesn’t take much. Even small changes in tone can have a huge impact on your team’s motivation and, soon enough, people will be excited to be on the winning team again.

Touch. When was the last time you visited customers in their offices? When was the last time you manned the booth at a trade show? How about meeting with the CEOs of your competitors? You need to get out there and touch the market again. If you haven’t sat onsite with customers and quietly observed how they use your products, start doing that regularly. Call the CEOs at your competitors and ask them to dinner. You’ll be surprised how much they worry about all the same things as you do. And one final exercise: Find a few companies you admire, call their CEOs, tell them what you are worried about, and ask if you can spend a day at their company learning about how they run their business. I guarantee they will say yes, and I know you will come back with some great ideas.

Team. After you change your tone and get back out in the market, you need to take stock back at headquarters. Is the team that helped you get where you are today the same team that can get you where you need to go? The answer is probably “yes and no.” Or maybe even “I don’t know.” For this exercise, I suggest that you do two things:

Get some help

Find an outside consultant or advisor who conducts executive assessment, team dynamic, and leadership development services. Starting with yourself, assess the skills you have on the management team to determine what gaps exist that will stop you from reaching the next company milestone. Be ready to fill the gaps by changing roles or adding missing skills. Then sort out how your team works together and where personalities might get in the way of collaboration. Be prepared to not only give more responsibility to those who are ready, but also to remove the cynics and change reporting structures to get conflict out of the system.

Give some help

Now you need to invest some money to develop your people so their skills align with the goals. For all their hard work, your team deserves this investment. You’ll be rewarded when you see your team take on responsibility and fill leadership roles. Unfortunately, not everyone on the team is going to fill the roles you need; so you’ll have to make hard choices.

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Tech. There is seemingly no end to the number of IT projects that could improve your business. Many founders delay the big ones because things seem “good enough” from where they sit. But the technology bill comes due sooner or later. Sooner when you have an event that disrupts operations, or later when you start losing out to competitors who slowly catch up and pass you.

Don’t know where to start? I suggest you discuss this during your day visiting the companies you admire. They can show you the technology they use. Plenty of technologies exist that can provide a big impact with relatively small investments for businesses that commit the resources and time. You need to find out what the best ones are for your company and commit to getting them done.

Devin Mathews is a managing partner at Chicago Growth Partners. A version of this post originally appeared on
www.pefuncast.com
.