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Intelligently letting go of functional areas

Welcome Entrepreneurs, I'm so glad you're here. 

Many of my clients have been wrestling with what it means to let go of their company as it grows, and how to do so intelligently without inviting undue risk. Like a parent letting go of her child, allowing her to make mistakes en route to her own development, so must a leader let go of the parts of her business that gave her identity in the early days, to allow them to expand beyond her.

But that shit is scary. And complicated. And it’s ok to wrestle with it.

For those of you wrestling, this week’s essay is about a simple reframe that can help you see where you’re still holding onto what your business was, and intentionally and safely let go and allow it to grow up.

If this resonates, or you have similar experiences, let me know.

When you first launch your company, you succeed by solving all types of problems, and rallying employees and investors to follow you. Your force of will is a superpower, and no problem is too big or too small.

But the more you use this superpower, the more dependent your company becomes on you. Each time you swoop in and solve the unsolvable, you put yourself at the center of your company’s ability to problem solve, and you make yourself a bottleneck to growth. 

To evolve from a force-of-nature founder to a world-class CEO, you must learn which problems to focus on, and which to leave alone. This means letting go of What problems and replacing them with Who problems.

A more nuanced approach to superpowers

I’ve written before about how leadership maps to the six types of problems. Listed in ascending order of leverage these are: When, How, What, Who, Where, and Why. 

When leaders begin to delegate, most start with When and How problems because these are the easiest problems to give away. For every new initiative, once everyone knows what needs doing and why, it’s easy to ask your team to come up with their own deadlines and tactics.

What problems are a different story. Founders tend to hold onto What for far too long. And once the team realizes that the founder is great at solving What problems (read: once the team realizes that the founder is particularly attached to his own ideas, and that no initiative will be green-lit without his buy-in), the team learns to bring all the hairy What problems to the founder. 

  • Complicated customer issue? 

    • Ask Richard. He will know what he wants to do. 

  • Debating marketing strategies? 

    • Ask Richard. He’ll have an opinion. 

  • This feature or that one? 

    • Richard. 

Before long, even talented operators learn it’s most efficient if they don’t think for themselves. Poor Richard is inundated with problems of all types every day. He feels like he’s doing his job with every problem he solves, even as he positions himself as an existential risk to his company’s growing up.

The reframe to increase your leverage as a leader

As challenging as this transition can be, overcoming it is simple: reframe all What problems as Who problems. 

As an example, an employee might say: “An important account is upset, and we need to figure out how to make them happy without setting a bad precedent. What should we do?” 

You may have an instinct to solve this complex What problem. Don’t. 

Instead, reframe it as a Who problem: “Who is responsible for handling customer issues? They need to make the call.”

If the answer to this question is clear, solving this Who problem is as simple as redirecting your team to the appropriate resource. 

If the answer is unclear, then solving this Who problem means empowering a particular person to own customer issues, and ensuring they’re sufficiently informed and aligned to deal well with the ambiguity of such calls. Afterward, they’ll solve the next What problem without you ever having to hear about it.

If the answer is clear and you’re hesitating (“it’s so small I don’t want to bother them,” or “it’s so complex I should just solve it,” etc), know that that is what it sounds like when a leader unintentionally stifles the growth of their company. Even if they choose differently than you would have, if someone is accountable for a given functional area and properly informed and aligned, you must let this person make the call and live with the consequences, or you must change that person.

Building a startup is solving problems. But not all problems are created equal.

I get it. What problems are appealing. They’re satisfying, and they feel like the nuts and bolts of running a company. We justify solving them with sayings like “removing obstacles” and “unsticking our direct reports.” But the road to mediocrity is paved with such sayings. 

For your company to grow, you need to shift your focus from What problems to Who problems, because the job of a scaling leader is not to remove obstacles from his team, no matter how productive it feels. The job of a scaling leader is to hire and empower the people who can unstick themselves.


Things I read this week

One: How some organizations have effectively rolled out Values (twitter)

Values can be either the lifeblood of your culture, or a colossal waste of energy. What's the difference? There are diamonds in this thread about how successful companies have leveraged values. 

LINK >>

Two: Five practices to transform a founder to a CEO (I-O)

The largest reason folks fail at working with values isn't because of the values. It's because the leader isn't ready to embody them. Good news is that it's possible, through practices like the ones I wrote about once before, to intentional ready yourself to be the leader your company needs. 

LINK >>

Three: A must read for dads (The Hoarse Whisperer)

"I had a moment with my son last night that I will probably long remember. We were sitting in a restaurant drifting in and out of watching the basketball game when he said 'Can I tell you something? I think I am the only one of my friends who has a good relationship with their dad.' Oof. So much in that one sentence."

Amazing story that gave me the feels.

LINK >>

Four: Something's off with how we talk about psychedelics (The Rubesletter)

Psychedelics are going mainstream by appealing to the medical establishment. Treating PTSD and so on. On balance this is amazing. But Matt Ruby has a point in saying that these medicines are important for the "betterment of well people," too.

LINK >>

Five: Fig Trees (The Overstory)

I'm reading "The Overstory" right now (which is fantastic btw), and inside I learned that a single fig tree can have hundreds of trunks. A single seed can take up acres of space. And then I learned that a dismembered fig branch, planted, can grow a whole new root system. 

Good thing I've given up thinking I know anything about the world. 

LINK >>


Want to dive deeper?

If you liked this, check out this list of my top posts, read and shared by thousands of entrepreneurs.

Here are a few of my favorites:


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I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency supporting founders to rapidly scale themselves as leaders, so they can thrive professionally and personally as their company changes the world. Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.

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