Have You Become the Chief Worry Officer?

Somewhere along the bootstrapping journey, the worries that consume successful company founders start to change. Back in the early days, making payroll provided enough stress. You didn’t have time to worry about the consequences; you just found a way to get through. But once your business is stable enough, allowing you to pause and catch your breath, you often find yourself starting to worry about more distant threats:

  • Does my team treat our customers the same way I did when we first started?

  • Are my salespeople looking hard enough for that next big deal?

  • Do we really need to make those investments my Chief Technology Officer keeps bugging me about?

Congratulations. Worrying over these things means your business will still be around after the next payroll cycle and you have time to worry about the future. And with most or of your net worth wrapped up in the company, 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 your new role, but your team can see it on your face and hear it in your voice and you can bet they talk about it when you aren’t in the office.

This new role usually takes shape after a company has achieved some success, when founders worry less about losing everything and more about just keeping what they’ve got. I stole this title from a founder I’ve known for a few years. When we started getting to know each other, I asked him why he was selling his business. He said, “I’m no longer the CEO, I’m the CWO.” He explained that for the last couple years, he just started saying “no” to everything. With several million in cash flow and a nice, stable business, as he told me that day, he had stopped “playing to win,” and had started “playing not to lose.” It takes a pretty self-aware CEO to be that reflective, and while he wanted to see his team succeed in the business, he didn’t want to take the personal risks required to achieve the next level of success because of all the hard work it took just to get to his current, comfortable position. This reminded me of the old football cliché about the “prevent defense” – the only thing it prevents you from doing is winning!

How can entrepreneurs break out of the CWO funk and get back in the CEO seat? What can they do to get back to playing to win again? Over my career investing with founders, I’ve discovered that you need to revisit four things if you find yourself in this common slump – let’s call them the “Four Ts” so we can all remember them.


This is the easy one. 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 the renewed passion, see the 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.


This is the fun one. When was the last time you visited customers in their office? 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 read George Day’s The Market Driven Organization, go out and get a copy. If you haven’t sat onsite with customers and quietly observed how they use your product, go do that a dozen times. 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 for your team to implement.


This is the hard one. After you change your tone and after you get back out in the market, now you need to take stock back at headquarters. Is the team that got you 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 (make sure you get references because you need someone you can really trust). Starting with yourself, assess the skills you have on the 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 and for the value they’ve created for you, your team deserves the investment in their development. You’ll be richly rewarded when you see your team take on responsibility and fill leadership roles. Unfortunately, not everyone on the team is going fill the roles you need; so you’ll have to make hard choices. This process will likely expose some critical gaps; so you might have to reach outside the organization to find some necessary skills. Though, in my experience I have fond that when you combine raising expectations with team development people accept change more easily, because they see that you believe in them and understand you want the best for the business.


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

There are only two kinds of IT projects – hard and difficult. The hard, but obvious, projects require spending money on new products or features. With these projects it’s easy to imagine the revenue that will flow in when the project is complete and the team is out in the market selling. Every company has a few obvious product investments that will quickly make customers happy; so start with those.

The difficult projects lack the obvious potential payback and require the most change in how the business operates. These projects involve harnessing technology to run the business better – things like customer relationship management, marketing automation, data analytics and virtualization.

Don’t know where to start? I suggest this as a topic of conversation when you spend a day inside the companies you admire. They can help by showing you the technology they use to help run their businesses. 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.

If you find yourself becoming the Chief Worry Officer for your company, snap out of it by following the Four Ts above.

Good luck and let me know how it goes.