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 over time in building a new business. This is even more of an issue when you’re trying to finance and grow a startup in the critical period when it begins to gain some traction and starts to scale. 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, you’re never going to get the business to the next level. And sometimes, you’re the only one who honestly knows that you’re the wrong guy or girl for the job.
The list of what it takes to succeed is a long one and I’ve written about these various attributes before and how challenging it is to have to balance so many competing considerations at the same time. You’ve got to walk that thin line between pushing the envelope and being somewhat patient so that you don’t get too far out over your skis and crash. You’ve got to be demanding and also delicate – getting the most out of your people isn’t the same as getting the best from them. Making room for people is all about different strokes for many different folks. You’ve got to have a thick skin to ward off all the naysayers and know-it-alls so you can keep going and an open mind so that you can not only hear, but also listen to and learn from, well-meaning and smart people when they tell you what you’re doing wrong and how things will need to change in order for the business to grow.
And all the while, you’ve got to keep your head up high and not let anyone see you sweat or worry. 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 - and it’s very hard to find the time to do what it is that you do best which isn’t everything for anyone. But no one’s gonna 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, running around like crazy, 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 isn’t ever easy to admit to yourself or anyone else that you may not be up to the job you’re in. And it’s even harder to share the truth with the other people who also need to hear it. It’s never easy to say what nobody wants to hear. And it’s especially difficult and more than a little scary for any entrepreneur to acknowledge that maybe they’re not the best person for the top job.
The Peter Principle is still alive and well – it’s just slightly different and more complicated when the person who’s the problem is also the founder or co-founder of the business rather than someone pushed or promoted into a position that’s over his or her head. I’d call this problem the Founder’s Fallacy. The idea that every talented engineer or coder comes equipped with the skills it takes (or even the deep-down interest or desire) to lead the business or that he or she will automatically grow those abilities as time passes is a foolish fantasy.
And oftentimes it’s actually the entrepreneur who figures these things out first. But knowing what should be done, admitting it to yourself and getting it done 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 and 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 importantly, 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. Nothing is all fun and games (that’s why they call it “work”), but the more time you can spend doing what you want to do, enjoy doing, and are really good at doing; the better the results for the business.
You need to ask yourself honestly if you’re really enjoying coming to work every day or if you’re increasingly frustrated because a million inconsequential things keep getting in the way of you getting the things done that you – and probably you alone – need to get done. If you’re honest about it, you’ll start thinking 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 – you’ve got a fabulous salesman trying to supervise day-to-day operations while he’s standing on one foot at the airport waiting for his next flight to see a big new prospect – and you’ve got a guy who loves machines and hates people worrying about HR matters. It turns out – he’s slowly learning - that even the smartest machines demand a lot less of you than people do. It’s not a good thing that he hates people, but – for sure – dealing with people is not something he’s good at.
The bottom line is that they need to quickly get real and make a better plan and they need to do it before their businesses fall apart or they get tossed out.
(2) Be Honest with Your Backers
Your Board and your investors won’t pretend to be even slightly happy to hear that you want to hire your own replacement even though they may well 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. Any leadership transition is challenging even when the ship is steady and it’s even more risky and perilous when the company is in the midst of a growth spurt. So expect everyone to be somewhat on edge including, of course, you.
To start out on the right foot, you’re gonna have to get over your own feelings of failure and inadequacy which can quickly poison the discussion if you’re not careful. You brought the idea to life; you got the ball rolling and now it’s time to hand the reins over to someone else so that you can return to doing what you do best.
Be careful here that you don’t get angry at the investors (or the world in general) for not appreciating you enough, not giving you the unlimited time and funds you needed to realize your dream, and/or not having your back and being disloyal to you (after all the sacrifices you’ve made for them) when the chips were down. I’m sure these sentiments are already familiar to you and that I’m not telling you anything new. But you have to put this stuff behind you. You need these guys on your side as much going forward as you did getting to this point.
You also have to deal with two additional emotional concerns and you need to convince the Board and the investors that you can successfully handle these feelings as well.
The first is 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 – and everyone who’s been through the process knows how quickly problems can arise if there’s not a clean and complete handoff. You can’t have two CEOs and you can’t set up a situation where your key people – for whatever reasons – start to shop for the answers/decisions that they’re looking for from whichever one of you seems the likeliest to agree.
The second 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 no longer regarded as essential to the company’s success. Sometimes this can turn into a serious problem where the prior boss acts in ways that sabotage the business. You would think that everyone involved was working in the same direction for the company’s success, but human beings are a little more complicated than that. It’s just a little satisfying to know that the guy stepping in to fill your big shoes isn’t finding things quite as easy to pull off or as straightforward as they looked when you were running the show. The Germans may have invented the idea of schadenfreude, but it’s alive and well in every C suite in this country as well.
The bottom line here is that you have to be out front and very clear with the Board and the investors that you’re 100% 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 going to be 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. While the circus is set up and all over town; it’s all bright lights, excitement and superstars. Once they strike the tents and move on down the road; it’s an empty arena, some broken dreams and sawdust all around. Once a startup reaches a certain size and level of maturity, some of the early dreams and hopes (or delusions) also die and some of the people who got you there can’t take you any further.
Political campaigns are even worse. You drive yourself and your team crazy trying to beat the other guys and then – when you win – the difficulties really begin because now you’ve got to make a series of impossible people choices and position selections and everyone in the running is someone who’s been there from the start and helped you make it all happen. There are no simple answers and all the decisions are hard. But it’s just another part of a job that no one ever said was gonna be easy.
The bottom line here – amid all the tears and hard feelings that will most assuredly be part of the process - is to be honest and to set 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.
PS: “You Get What You Work for, Not What You Wish for”
