Founders Dilemma: Making the Leap to Growth

A business coach friend of mine was trying to help a promising little company grow.

They had an amazing founder: He was smart, hard working, and had a compelling vision for his company. It was a niche media company, and while his content was unique in the Seattle market, there were other similar companies in other regions who had successfully scaled up. That gave him proof of concept and several different models for growth. He had people who wanted to help him—advocates who were inspired by his vision and impressed by his skills. They wanted to help fund him, help build infrastructure, to make introductions.

But he didn’t have time. He didn’t have time for anything related to growth because all his time was spent on maintaining. Like many uber-competent people, he was managing finance and social media and vendors and partners and product planning and building and execution and buying printer paper. He told himself, and everyone else, that it was “easier” for him to do it. He was the grand marshal of the parade; he was also every member of the marching band, the driver of every float, and the guy who sweeps up the rose petals at the end.

It’s not that he didn’t understand the problem. He absolutely did. But at the same time, he was not able to let go of any of the day-to-day tasks of running the business. He and his business coach went around and around on this issue, highlighting the need, brainstorming solutions.

He eventually stopped returning the coach’s calls. There was no where to go.

There are so many bad business ideas. So many people who only want to make money, to half-ass on quality, to cash in and then close. When you see a company that is really special, with a strong mission and a needed product, it’s painful to watch the founder chose to spend their time ordering office supplies.

“It’ll only take a minute…” is what he told himself, and what we’ve all told ourselves at one point or another. But those minute-long tasks can eat up a morning, a day, a life.

There’s nothing wrong with a, intentional, strategic decision to stay small. Many people make that choice because they know scaling up might mean losing control over the product, or maybe it would just take the fun out of it. I like working in teams, but I also like being a solo communication shop because I like all aspects of my work, and I like to go deep. Scaling up would mean having more of my time go to management and oversight, and less time to doing the actual work. Many skilled craftspeople make the same decision, to hand-make 5 units a month instead of manufacture and distribute 5,000 a month. Obviously, the world is richer with both.

The heartbreak I’m talking about is when the founder wants to grow, but can’t let go of controlling every aspect of development, production, sales, etc. You can’t have both things. I know. It sucks. But sometimes you have to decide.

There is a American narrative that the workplace is an emotion-free zone. We leave feelings at home when we come to work, where we commence to make rational decisions. Also, rational decisions are more correct than emotional decisions.

Insert eyeroll emoji. Also maybe forehead-slap emoji.

We have this idea that 1) emotion and rationality are opposite, 2) that a human can be unemotional, and 3) that unemotional (rational) decisions are some how better than other decisions. If we see decisions only in terms of some sort of rational cost-benefit, we are choosing to ignore a huge dynamic that is still very much in play.

Maybe our founder was right, that it was easier for him to do every single business task, instead of delegating. But might it also be true that it was emotionally hard for him to give up control? He didn’t want to train, he didn’t want to trust, he didn’t want to let go, he was scared the company would fail, if he wasn’t personally holding every piece in place.

He may also have been intimidated by the need to shift from a highly competent doer to a less-competent leader, which is a huge transition in self-identity.

So what to do, when you realize that what got you here will not get you there? Whether you’re growing a company, or just thinking of your personal career development, we all come to the point when we realize we’ve maxed out our current abilities, and the next step up is going to require a whole new toolkit.

Think also of how it feels for a kid to leave the cocoon of elementary school and enter the wild world middle school. Or how different it is, to be the parent of a small child, compared to the parent of a high schooler. Those big changes don’t stop in school. When I was working in newspapers, they’d often take the best reporter and “promote” them– into being the least experienced editor. Both are fundamentally jobs for journalists, but they are very different skillsets, and the evolution requires letting go of a lot of habits and mentalities. Company founders have to go on the same journey, away from being a top musician and toward being an inexperienced conductor.

Evolution isn’t a smooth process of small changes. Evolution is herky-jerky: Big, fast changes in the environment kill off some adaptations and allow others to flourish. But it can be managed.

The first thing to acknowledge is that growth means change, and change is hard. Leading a company through growth is HARD. It takes new skills, new knowledge and a stomach for risk. When we found a company (or start a career or learn a sport or have a child), we are deeply, deeply invested in that project. We care more than any one else, we watch more, we touch more, we think more, we fret more. It is our day dream and night dream and our identity and the focus of our lives. This one-man-band stage can go on for years and honestly, there is something nice about that. It’s comforting to know where everything is. If you work with a partner, it’s a time of shared dreams and synergy that in the future, will always trigger some nostalgia.

The fact remains, however, that any kind of growth is going to mean a move away from that level of intimacy with the product. We have to let go of tasks, we have to let go of what we’re good at, and spend more time doing what we’re less good at. If we fail to acknowledge the emotional difficulty of that change, we risk sabotaging ourselves by holding onto control over small things that don’t matter in the long run.

Good news/bad news. It’s going to involve other people. There is no growth without other people.  You have to let people in, you have to give them control over parts of you baby, and you even have to let them fail. It is scary to trust other people. You will make hiring mistakes. Other people might lose you money. They don’t know as much about the business as you do, and might not want to. They absolutely, positively will not care about the business as much as you do. You will be mystified by their lack of passion about the company that is the center of your identity.

On the other hand, you won’t be alone any more. And you’ll also make great hiring decisions, which will broaden the number of eyes and hands available to solve problems and seize opportunities. The “new people” won’t be as passionate as you, but on the other hand, they’ll be more objective. You’ll end up hiring people who are better than you, which could be awesome, depressing, or both. And if you get the flu, or COVID, or break a leg, the business can continue to make money while you rest. Imagine that.

It’s possible to kick the junk-time habit. Junk time is like junk food: it meets an immediate need with little effort. Like cleaning your room instead of working on a term paper, junk time gives you a little buzz of productivity without the pain of hard work. But just as it’s possible to be obese and have malnutrition, you can complete all the tasks on your list, feel really good about yourself, and not make any real progress at all. That was where our founder was. He was doing all the tasks, felt busy and productive, but wasn’t making any progress on his growth goals. Empty calories, empty productivity. The quantity of our time is set by the clock, but we can manage quality. He didn’t need more time so much as he needed to spend his time in higher quality ways.

The analogy to parenting and other personal projects is hard to miss. You can do tasks for your kids all day long, but that’s not the real purpose of parenting. The real purpose of parenting is to grow healthy and good adults. Yes, you have to wipe their butts and make their sandwiches, but that’s just maintenance. It’s not growth.

So whether you do a formal time audit, or just have a hard talk with yourself, the first step is to realize to what degree small maintenance tasks are in the way of big growth. It’s a constant battle, but once you realize the problem, you can start breaking down the barriers, step by step.

Change is hard. So is letting go. This Forbes article does a nice job of describing four stages of growth, and how the CEOs role changes at each level. It’s obviously extremely difficult for the same person to lead an organization at each stage. I worked with a woman at a nonprofit who was an outstanding visionary and entrepreneur. She was great at starting things: she knew trends, she knew how to exploit gaps in the marketplace, she was agile, she could excite funders and staff.

She was, however, unfuckingstable. Her priorities changed every day, and staff got whiplash from trying to predict which way the wind was going to blow. Because she was unable or unwilling to communicate a consistent vision, she had to micromanage everything. Progress was impossible. Once she left and her division was handed to someone with less personal ownership, they were able to stabilize and grow. But the second leader could not have EVER been the first. We need the Prometheuses, the fire-bringers of the world. We also need fire departments.

A company or service line simply cannot grow if the leader has their hands on all the levers. Growth requires letting go, and making room for many, many other people, with their diversity of skills, abilities, perspectives and motives.

Conclusion

That little media company isn’t growing right now, but that could absolutely be fine. It’s highly possible that while the founder originally had plans to grow, once he saw the path and the tradeoffs required, he made a conscious choice to stay the course. I hope the founder made a choice to stay small and is enjoying the hell out of running his business. Making conscious choices is central to our wellbeing, both as leaders and as people. And I personally love being in an economy with individual craftspeople, small businesses, mid-size and large companies, all doing different work in different ways.

What I don’t love is people feeling stuck and not understanding why, or what to do about it. There are so many ways of breaking problems down and solving them, and the main barrier is that we are unwilling to ask for help. (Stupid humans.) Once we do invite people into our problems, we can develop a menu of solutions, build an army of helpers and start to really build.

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