I get that everyone wants to be the boss. But the truth is that very few people have the necessary set of emotional, technical, and intellectual talents, skills, and tools that it takes to succeed in building a new business. This becomes even more of an issue as your company starts to gain traction and you seek financing. Sure, you can try to hurry out there and hire some grown-ups to help, but if you've got the wrong person in the driver's seat (i.e., you), you're never going to get the business to the next level.

The tricky thing is, sometimes you're the only one who knows that you're the wrong person for the job.

The list of what it takes to succeed is a long one: You've got to walk that thin line between pushing the envelope and being somewhat patient (don’t get too far out over your skis); you've got to be demanding but also delicate (getting the most out of your people isn't the same as getting the best from them); you've got to have a thick skin to ward off all the naysayers and know-it-alls, but also an open mind (there are many well-meaning and smart people who can tell you what you're doing wrong, and how to fix it).

Are You Doing What You Do Best?

Leadership is an ongoing performance art--and you're never offstage. It's an all-consuming, constant juggling act, and it never slows down or gets easier. And because there are always so many different things going on, it's very easy to get spread a mile wide and an inch deep, to keep jumping from one crisis to another without taking a breath. Amid all that it's very hard to find the time to do whatever it is that you do best. And no one does everything well, but don't expect anyone to go out of their way to tell you that, or to tell you to take it easy. It's all pedal-to-the-metal and balls-to-the-wall. They've all got their own agendas and going slow isn't anyone's idea of how to get ahead today.  

And that's the really bad news: Spending the lion's share of your time trying to be all things to all people and trying to do a little bit of everything that needs to get done may not be your highest and best use, or the way that you can make the greatest contribution to the ultimate success of the business.

But it's never easy to admit to yourself (or anyone else) that you may not be up to the job you're in, and it's especially difficult for any entrepreneur to acknowledge that maybe they're not the best person for the top job.

Not only is the Peter Principle alive and well, but it becomes particularly complicated when the person who's the problem is the founder or co-founder of the business. I call it the Founder's Fallacy: the idea that every talented engineer or coder either comes equipped with the skills it takes (or even the deep-down interest or desire) to lead the business, or will automatically grow those abilities as time passes. It's a foolish fantasy.

Often the entrepreneur is the first person to realize this, but admitting it to yourself and acting on it are very different things. But, when corrective action is required, if you don't initiate the process and try to guide it you can expect one of two outcomes: (a) the business will start to go sideways, stall out, and eventually fail; or (b) the investors will finally work up their courage (and overcome their own fears and reluctance) and they will come for your head. It's much, much better to get ahead of the wave than to get pulled under and washed out.

There isn't one approach or formula that fits every case, but there are three basic ground rules that govern this process. You need to work through them and see where you and your business stand.

1. Be Honest with Yourself

We each have our own strengths and weaknesses. We need to play to them and not ignore them. But, even more important, each of us has things that we love to do and other things that we abhor and do poorly. The trick is to find the highest position possible where you still love doing what you're getting paid to do.

Ask yourself if you really enjoy coming to work every day or if you're increasingly frustrated because a million inconsequential things keep getting in the way of the things that you--and probably you alone--need to get done. If you're honest about it, you'll think about getting someone else in there pronto so you can get back to taking care of the real business.

I'm watching this scenario play out in at least three young businesses right now, and every case is remarkably similar: You've got a guy who's great at analysis and data acquisition trying to deal with the banks and accounts payable, or a fabulous salesman trying to supervise day-to-day operations (from the airport as he jets off to see a big new prospect), or a guy who loves machines but hates people now worrying about HR matters. The bottom line is that in each case they need to quickly get real and make a better plan, before their businesses fall apart or they get tossed out.

2. Be Honest with Your Backers

Your board and your investors won't even pretend to be happy to hear that you want to hire your own replacement, even though they may be secretly relieved that they didn't have to force the issue. After all, this is really one of the only two things ( overall strategy being the other) that they should be concerned with, even though they generally spend way too much time in your shorts and in the weeds of the business.

But even if they're expecting it (or fervently hoping for it), this is still a complicated conversation that you need to handle exactly right. First, you have to get over your own feelings of failure and inadequacy, because they can quickly poison the discussion if you're not careful. Focus on the fact that you brought the idea to life and got the ball rolling; now it's time to hand the reins over to someone else so that you can return to doing what you do best.

Second, don't get angry at your investors (or the world in general) for not appreciating you enough, or not giving you the unlimited time and funds you need, or not having your back. You have to put this stuff behind you, because you need these guys on your side as much going forward as you did getting to this point.

You also have to deal with the loss of control. Entrepreneurs are all about authority and control, so it's understandably very hard to let your baby go, even a little bit. But everyone who's been through the process knows how quickly problems arise if there's not a clean and complete handoff. You can't have two CEOs, and you can't create a situation where your key people start to shop for the answers or decisions they're looking for.

And then there is the fear of being forgotten. Entrepreneurs very quickly get used to the spotlight, the strokes, and the applause, and it's hard to walk away. They don't want to be forgotten or regarded as no longer essential to the company's success. Sometimes ex-bosses act in ways that sabotage the business, perhaps to enjoy a jolt of satisfaction from proving that the new guy didn't have all the answers after all. The Germans may have invented the idea of schadenfreude, but it’s alive and well in every C-suite in this country.

The bottom line is that you have to be up front and very clear with the board and the investors that you're 100 percent on board with the transition plan and willing to do whatever it takes to make it work. One of the leader's most important jobs is to create the next generation of leaders.

3. Be Honest with Your Buddies

The people who are going to be the most concerned and anxious about your decision are the ones you are closest to and most dependent on. They're gonna feel abandoned, disappointed, and more than a little angry that you're leaving them in the lurch--even if you're not. Sometimes the hardest part of being the boss and making the tough calls isn't fighting off your competitors, it's having to deal with the hurt feelings of your friends. But those feelings can't keep you from doing the right things for the business.

Startups are a lot like circuses and political campaigns: intensely high-energy and high stakes exercises carried on in incredibly compressed timeframes, with most of the hard work and tough decisions taking place out of sight or after the excitement has passed.

The bottom line, amid all the tears and hard feelings that will most assuredly be part of the process, is to be honest with everyone and to lay out the circumstances and your choices as simply as possible. And then to remember that you can explain things to people, but you can't understand those things for them.

Published on: Sep 17, 2014