By Jack Cumming

Is “to CEO” even a verb? It should be. Do you aspire to CEO? If not, why not? Perhaps you are well-qualified and just doubt yourself. Instead of letting fear limit your life, lift your sights.

We’ll get back to corporate CEOing, but for you self-doubters, join the community organizations near you. Think creatively — it might be Rotary, the Chamber of Commerce, or Toastmasters. Learn to believe in yourself. Remember, you are CEO of your own destiny, choosing whether to advance and grow or to settle and drift.

Prepare for Opportunity

My personal growth preference is Toastmasters, which helps cure the fear of public speaking. For your speaking commitments (Toastmasters requires a series of talks), choose topics that focus on what you see in business that limits the success of the company where you work. That way you gain confidence, learn to speak with poise, and develop a personal business philosophy committed to success.

But, now, start imagining yourself as CEO. You can hone your leadership by helping others grow on the job where you work. But, while you’re dreaming, picture that moment. The board has just met and approved you as the successor CEO. What runs through your mind as the board members surround you with congratulations and, perhaps, a celebratory toast? Is this moment the pinnacle of ambition, or the next step in leadership?

The Alternative

Not everyone, though, is chosen as CEO. The alternative is that you grow impatient with waiting to be chosen. Perhaps, someone who lacks your talent, but who is good at schmoozing the board is advanced before you. Perhaps, there’s someone ahead of you, who still has decades to go, while the business drifts toward complacency. The alternative celebration is the dream day you found your own company.

If you follow the second path, the likelihood is that you’ve been honing your thinking into a business plan over many months. You may be thinking of surpassing the business of your stagnating employer by bringing to the market the imaginative future that your employer ignores.

You’ve take into account noncompete constraints; you have capital financing sufficient to bridge you to sustainable cash flow; you’ve thought of the risks and know how to manage them. The day you make the jump is a day you’ll never forget. The day you land your first paying customer is another.

Two Paths

Two paths to CEO, one more comfortable than the other. Both paths, though, require deep-dive business planning. If you have trouble seeing the opportunities, and the challenges they entail, then you’re probably not ready to CEO. If you just want to administer the operation you’ve inherited, but you’re already CEO, then you may want to look for a merger for the sake of the business. It’s never wise to put self before results.

If your path to CEO is the second, startup path, then you have to pitch in as master of all trades while assembling the team that you need to move quickly toward positive cash and positive earnings. The longer it takes, the more capital you will burn through, and the harder it will be to succeed. Speed and performance matter.

If your path to CEO is by board anointment, either as the inside or the outside candidate, you have to be fleet of foot to avoid losing the going-business you’ve inherited. If you’re the outsider, chances are you’re leading a troubled business. You have to ask why there was no inside talent ready to step up. As the outsider, you may know if the board expects you to turn things around, or you may need to lead change even if the board wasn’t explicit. Let’s be clear. This isn’t omniscience. It’s common sense.

Taking Charge

Now we can jump forward. If you were the crown prince now elevated to the top post, you have to the hit the ground running. Some of your colleagues who were passed over for the job may not be happy. Be sure to maintain performance across the organization even if that means facing some difficult realities. You are now responsible for the business’s success or failure, and responsibility can’t be delegated nor should it be deflected. You own it.

If you are that rare start-up CEO who gets past all the high-risk capital tranches, to be leading a stable sustainable business, you are one of a select few. Still, here you are. You’ve made it! Wow, doesn’t that feel good? Stay modest, you’re on full display now, and not everyone is your friend, and not everyone is happy for your success. In business, you have to earn your stripes every day.

It’s tempting to believe that as CEO you’re now the boss. That seldom ends well. First, you report to the board, and some members may be listening to inside dissidents. Second, unless you’re a genius in a class with Elon Musk, you’re not likely to be the smartest one in the room. You want those smarter, more talented folks to feel valued and loved so they give you the benefit of their talent. That’s a tough call. An eye for talent, and how to attract and keep them, is the attribute most essential for a CEO.


Then, there’s the task of managing. Of course, if people come to you for decisions, you can ask, “What do you recommend, and why?” so you can see how their thinking aligns with yours. If they’ve thought of something you didn’t, give credit where credit is due. That sense of self-confident credit sharing is what distinguishes great CEOs from the rest of the crowd.

Then, there are two managerial tools that may help you to uncover and unleash the opportunities that lurk within the organization. The first is an “accountability meeting.” Forget structure, and bring together all of those at whatever organizational position who have end-of-the-line responsibility for project or functional performance.

Each attendee reports: 1) actual progress/performance relative to what was promised and 2) actual expense relative to expected. Group accountability allows peer pressure to encourage people to their best results. It also allows peers to help others for the benefit of the whole. Those who stand out move up. Others move out.

The other tool is a “CEO briefing.” Like the “accountability meeting,” the briefing focuses the CEO spotlight on those who have end-of-the-line responsibility. Forget corporate position. You’re looking for talent. These are the same people as in the accountability meeting, only here they present one-to-one. It’s a chance for the CEO to coordinate facets of the business to ensure that rivalries aren’t retarding performance and that the future is seen clearly.

Loyalty Is Contagious

A governing principle for successful leadership is that loyalty to people – employees, customers, investors, suppliers, and others — is more important than loyalty to business aggrandizement. Too often this is misunderstood, destroying the bonds of integrity and trust that are crucial to business credibility.

Finally, even if you aren’t now CEO of an enterprise, you are the CEO of your own destiny. Think of yourself as a business. You, as an individual, sell your capabilities, perhaps to an employer, or if you work gigs, to your clients. Value yourself.

Maximize your value to your employer, but if that value isn’t recognized, it’s time for a strategic reassessment, just as would be appropriate for an underperforming business, and you need to fashion a new path that allows you to optimize your life, your worth, and the respect that you deserve. Never let rivals diminish you. Look for friends and collaborators to help you reach your dreams.