CEO Coaching: Can You Transform From Entrepreneur to Real Leader?

Because I typically travel to work with the executives I coach, I found myself with extra time during COVID. I work with midmarket CEOs and their teams, but for some reason I was getting calls from small business owners. It wasn’t right to turn them away, so I helped some for free or a very reduced rate. I’m glad I did, because I helped them think differently and, of course, learned from them as well.

I noticed, however, that there were some consistent, and frankly unprofessional characteristics with this entrepreneurial crowd that could prevent them from leading larger organizations. I have great respect for entrepreneurs, but if I can reach one or two of you, I hope I can prevent your early demise.

It’s wonderful that you started (or perhaps inherited) a business that profitably addresses a market need — you found the launch pad! But the fact that you had a good, maybe even great, idea doesn’t mean you understand organizational behavior; you know, all that “people” stuff. Don’t assume that intelligence, risk-taking and resilience (which most successful entrepreneurs have in spades!) mean you can run an organization any more than you can fly an airplane. Confidence and instincts won’t make up for no training and experience. Get some help!

Learn how to use a calendar. It’s one of the most important tools for helping ensure success as you grow. It reflects your priorities, keeps you from doing silly things, allows you to maintain relationships, and creates credibility by not missing appointments and deadlines. I’m writing this blog during the time one of my entrepreneurial clients was supposed to call for a standing coaching appointment (a somewhat typical event). My clients pay in advance, so I’m whole, but I’d rather they get the benefit they pay for. My clients who’ve had a longer run in a larger organization rarely miss an appointment. 

Your job, as you grow, is no longer to be the chief salesperson, chief financial officer, production manager and decider of all things. You cannot move forward unless you let go. If you keep doing what you’ve always done, you’ll probably keep getting what you always got. If that’s what you want, good for you, but don’t profess a desire to learn how to be a real leader and then refuse to get out of the weeds. If you want to lose weight, you can’t keep eating the same crap!

Early-stage companies and many smaller, long-lived companies may not need detailed plans. They need faster response times. Larger companies with professional leaders need both. Plans aren’t the enemy! They allow your people to do their work and you to align your team and budget effectively (perhaps so that you can count on your distributions!). They’re more freeing than constricting. Take a long vacation and don’t plan a thing, but if you refuse to think about the future and how you’ll succeed in your business, you’re bowling in the dark!

Embrace effective process. Weekly meetings with your senior team; performance reviews; and a real product development process (e.g., stage-gate) vs. pen and napkin at lunch aren’t a waste of time (as long as you learn how to do them effectively!) — they’re an investment! Too much bureaucracy and process too early can suffocate a small company, but you need “age-appropriate” behavior as you grow. The pilot flying that airplane I mentioned earlier isn’t “winging” it, and you shouldn’t either!

Learn how to share. Share the responsibilities (with talented managers you bring in, not your brother-in-law who needed a job!), share the wealth, share your joy and share your fear. Share the obligation to chart your future path with your senior team — no more Lone Ranger stuff! You aren’t Superman/Superwoman, and you don’t have all the answers. If you believe you do, you’re heading for a wall at some point.

The world needs entrepreneurs to birth new ideas and companies. The characteristics that make you a successful entrepreneur often don’t lend themselves to leading a large organization. Either learn the skills required or sell your company and start another! However, two of those characteristics — resilience and determination — might lead you to become a real leader! Lean on those and get some help!

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