Category: Team

I met up with some entrepreneur friends, Keith and Adam, to play a board game last weekend. Keith has been grinding to get a new SaaS product released that is an extension of his highly successful core SaaS product. After we finished gaming, we hung out in his kitchen and talked about the journey.

Keith said that he’s spending most of his time writing code, but to scale to his ideal exit point he needs to figure out enterprise sales.

Adam asked, “Why don’t you just hire a developer?”

“No one’s good enough to work on this problem,” he replied.

“What are the things in the business only you can do?” Adam asked.

“Product management, figuring out the strategic direction, what to build next,” Keith said.

I asked, “What’s the function in the business that is foundational to everything else? That must be accomplished and enables everything else?”

Keith thought for a moment and then said, “Sales.”

This is a challenge that many of us come to as owner operators.

What interested me in martial arts as a child was that skill gave you almost a super hero level of invulnerability. In the movies, the expert martial artist would fight groups of people and come out on top. As an adult training in the martial arts, the better and better I became, the more I realized that this was a fantasy. In a real fight, even someone exceptionally skilled has the odds heavily stacked against them as soon as another opponent appears.

To make a math comparison, a normal person’s threat in a live environment is a 1. An excellent martial artist might raise their threat to 1.5. Once another person comes in, the odds are now 2 : 1.5, add another opponent and they’re 2 : 1.

A lesson that I return to again and again is that whenever I step in to solve a problem, I’m robbing someone on our team of the opportunity to grow.

When I was a teenager, my dad told me that you train people how to treat you. The same thing happens in a team with how you respond to challenges. If there’s a challenge in the business and you always hop on your horse and lead the charge, you’re going to train your team to look to you whenever a problem appears. You will advance your capabilities while they stagnate.

This isn’t to say that you nurture growth by tossing people into the deep end and yelling, “Swim or drown!” Rather, it’s that if you’re going to develop your team, you need to restrain the impulse to fix everything and reign in what you contribute.

Start with:

“What are your ideas?”

“What do you suggest?”

“What are the obstacles?”

Featured image is a Moroccan with his Arabian horse along the Barbary coast. By Eugène Delacroix. Used under public domain.

We tend to perceive information as static and think in abstractions. However, our experience is passing through time. What something means and how it works is different depending on that passage. For example, if I asked you how to build a campfire, you might reply, “Build a tipi with tinder, kindling, and wood ascending outward in layers.” That’s generally accurate. But if I asked you how to build a campfire in February, when everything is sopping wet, you would have a different answer filled with consideration.

Similarly, though there is much advice on who to hire and how to hire, I haven’t come across much concerning when to hire. The answer to that question depends on how quickly you’re growing.

Imagine a circus performer juggling three balls. They could do this in their sleep while composing haiku in their dreams. As the business grows, you’re going to throw them another ball. Four is a little more challenging, but they adapt. The business makes a little more progress and you throw them another ball. Five is their very limit. Their hands are a blur and sweat drips down their face. They can do this for a couple of minutes at the most. But you toss them another ball anyways. They drop a ball. You toss them another. They drop that too. After a few minutes they drop a couple of more balls and are back at three and having difficulty with that. Suddenly they stop juggling and start throwing the balls at you and then storm out of the circus tent to have a cigarette.

I spent a significant amount of time doing operational work the first two months of this year. I’ve been providing digital strategy for client projects and augmenting our project manager. It’s an issue because my goal has always been to be a business owner and not an owner operator. The challenge of the situation is that, like many owner operators, I fill several gaps in capability in the business. The gaps I bridge are high risk areas where skill and care are required. Because of this, hiring someone isn’t as clear as if I were replacing an existing employee.

In considering this challenge, I asked one of my friends for advice. Specifically, I asked who he would hire next?

I read Stephen Covey’s book, 7 Habits of Highly Effective People, when I was a teenager. One of the habits that I return to again and again is to, “begin with the end in mind.” This perspective puts a lens over activity that encourages selection. It improves our ability to make decisions that support intentional change.

There are many ways this habit supports business growth, but to focus on a single example, do you know who should be on your team? Not for today, but for tomorrow. At your next stage of growth, what are the functions, roles, and people?

We tend to react to the environment and problem solve current situations. You hire or contract a sales role to drum up more business because your team is under capacity.

This isn’t inherently wrong, but you’re dependent on environmental cues that will shape your business. They will determine the shape, size, and kind of business you run.

It’s like only sailing in the direction of the wind.

But if you know where you’re going, you can make choices to bring sailors onboard that will aid in navigating to your desired destination.

Featured image is Dort or Dordrecht: The Dort packet-boat from Rotterdam becalmed, 1818. By JMW Turner. Used under public domain.