How to delegate
Welcome entrepreneurs. I’m so glad you’re here.
Today we’re going to tackle a topic near and dear to every scale-up founder’s heart: Delegation.
To scale a company, you have to learn to delegate. Full stop.
“Learn to delegate?” you might be thinking. “Isn’t that just telling other people what to do?”
Sure, at first. But if that’s as far as you take the discipline of delegation, your company will hit a wall around 15-25 people, and you’ll find yourself at the center of a wheel, in which every single spoke needs you for every little thing. It’s exhausting, unsustainable, and completely preventable.
How do you prevent that fate? Or, if you already find yourself there, how do you get out?
You shift from delegating solutions to delegating problems.
Let’s dive in.
How to delegate effectively as you scale
When you first start your company, you have to do everything. You’re marketing, sales, product, operations, customer support all rolled into one. And because you carry a vision of the big picture in your mind, and you care so much, even if those things aren’t your skill-sets, you develop ways of doing them that are effective. Then, when it’s time to backfill, you simply give the new person the SOP, and send them on their way.
This is what is called “delegating a solution.” You’ve done the work to figure out the best way to do something, and you tell your employee exactly what must be done, how, and any benchmarks that must be met. All that’s left for your employee to do is execute.
I’ve written before about the six types of decisions, and how you can plot the maturity of a leader and her company by the types of decisions she finds herself making most often. Briefly, here are the stages, listed in order of decreasing leverage:
Why (mission)
Where (vision, objective)
Who (responsible party)
What (what needs to be built)
How (how to build it)
When (by when)
When building a company, at first you make all the decisions. But, as you begin to develop a team, you progressively let go of decisions, starting at the bottom. Letting go of how to accomplish a given task and by when is typically relatively easy, but early on in the development of your team (say up to 20 people or so, for most founders), you are often the only person who understands the big picture, so it’s up to you to own at least the top four of the six types of decisions.
At this stage, as long as the employee’s work is well understood and static, they can be successful. But the minute accomplishing their work involves a change of scope, any ambiguity, or something you didn’t discuss, they must come back to you to see how you want it done. This is because when you control the What decisions, you constrain your employees to only thinking at the level of How. They focus their attention on figuring out the best way to give you what you want.
Never mind the fact that you can’t possibly know everything that you really want, and the fact that you need your team to help you see the best solutions. If you’ve ever grown a company, you know that these “do you want it this way or that way?” questions coming from your employees can keep you trapped working In the business, rather than On it.
Gaining leverage by letting go of the “What”
The way out of this quicksand is to consciously let go of What decisions. The method to doing that is to stop delegating solutions, and instead, look for the problem your solution is solving, and delegate that instead.
By way of example, a client of mine had hired an interim COO, and was frustrated that she wasn’t performing the way he wanted.
“I get it,” he said. “She only has so many hours in the day. I’m only paying her for part time, so I can’t ask her for full time work. But the problem is there is so much stuff to do. We agree on the role, and what a COO should do, but then she can’t get it done because she doesn’t have enough time. So then I end up doing the shit, and I can’t keep doing that. Do I need to hire a new, full-time person?”
“Maybe,” I said. “But maybe not for the reason you think. Remember our conversation about delegating problems vs solutions? Take a look at what’s happening here. Which do you think you’re doing?
He considered. “I am delegating a problem,” he said confidently. “Every one of the things I’m delegating to her, they don’t have solutions yet. She needs to figure out the solutions. And she’s good at that! That’s the frustrating part. If she just had more hours it’d be fine.”
“Can I share what I’m seeing?” I asked, making sure he was open to a different perspective. He nodded. “I think you’re delegating a solution here.”
He screwed up his face in confusion.
“What’s the problem you’re solving here?” I asked. “Not the specific areas you’re asking her to focus on. What’s the real problem, the one that we’re talking about?”
“Well,” he paused, considering. “She doesn’t have enough time, and I have to do too much of the operation stuff that I’m paying her for.”
“Exactly,” I said. “That’s the one I’m looking at, too. And who is solving that problem, given that we’re here having this conversation?”
“Shit, I am,” he said, getting more animated as he continued. “I’m telling her what needs to get done, she’s saying she can’t in that amount of time, and handing a problem right back to me. And I’m just accepting it and prioritizing for her.”
“And what would it look like to delegate that as a problem, rather than its solution?” I could feel him settle, as he thought about my question.
“I’d tell her that I need ten pounds of shit to fit in a five pound bag,” he began, colorful as always. “And I’d ask her to figure out how to make it fit. We do need all of it done, so that’s really the problem. I’d have it be up to her to figure out how to move pieces around, allocate the resources she has, or systematize things. Whatever she has to do to make it work. But ultimately, making it all work is the problem I’d delegate to her.”
“Sounds like a COO’s job to me.” I agreed.
Once he had delegated the What decision to his COO, he was free to move up the chain to the level of Who, and consider whether this COO was the right person for the job. At senior levels, this is what it looks like to gain leverage.
Why this is so hard for founders
This is challenging for anyone, but especially for founders.
From the minute you start your company, you are solving problems. And the faster and more accurately you solve those problems, the more successful you become. It’s the ultimate feedback loop, training you to become a super problem solver, and then providing positive feedback every single time you do.
Living inside this environment for a long time, it’s only natural to develop a belief that “work = solving problems,” and an identity that is built on a superhuman ability to do so.
That identity is like spinach to Popeye in the early days of a company. But as the company scales, it becomes closer to kryptonite.
To move away from solving the tactical problems of the early days (operating at the What level) and instead to hiring great people (operating at the Who level) and delegating problems to them, you must go in the opposite direction of your identity and belief structure as a founder/builder: instead of solving problems like a banshee and feeling uber productive in the process, you must let go of deciding what you’re building, and demand that your people figure it out. Your role becomes defining the outcome and the constraints (budgetary, branding, resource, etc) within which your people can operate, so they can successfully make those calls within the context of the greater organization.
To many founders, this shift from IC work to leadership feels like asking their employees to do their work for them. As such, developing the ability to lead well, and naturally, requires a founder to redefine productivity for themselves, and fundamentally shift their professional identity.
It’s a transition that takes time. And practice. In my work with CEOs, it’s often a process that takes months.
But it is also a process with a definitive finish line. You just have to have the guts to get started.
A note about people
Not all people are capable of solving What problems themselves. In fact, most people are best suited to solving How problems, and having someone else figure out the what, where, and why (the primary distinction between early startup employees who scale with the company and those who don’t is the ability to make this shift).
So before delegating a problem to an employee who has only ever executed defined solutions, consider whether they’re equipped to succeed at that task. Some aren’t. The best way to suss this out in my experience is to give them small problems to solve, ones for which failure is not catastrophic, and see how they do. If they do well, increase the scope of their problems.
But if you find yourself delegating solutions across the board, and feeling a vague resistance to giving that up to most people on your team, either you’ve got a team issue and must make some serious changes, or you are yourself holding onto an old personal definition of what good work, done well, looks like. It’s much cheaper to do the work on your identity first, before making one-way personnel decisions.
An exercise to get started
Here is a simple process to start extracting yourself from the quicksand of solving everyone’s problems for them:
Choose an area of your business that you’d like to delegate, but one on which it has been difficult for you to make progress
To start, choose an area of your business with which you’re willing to experiment. Something that, if it isn’t done perfectly, isn’t going to sink the company.
Consider if you are delegating that area as a solution (ie here’s what I need you to do) or a problem (ie here’s the problem I’m trying to solve, it’s now yours)
One signal that can be helpful is to check to see whether you have a strong opinion on what that person needs to do, and what it looks like when it’s done “right.” If so, you’re likely delegating a solution.
If you’re delegating a solution, consider what problem your solution is intended to solve.
For example, if you’re asking someone to write copy for you, you may be delegating a solution to the problem “I need more leads.”
Experiment with delegating the problem instead. Include both the problem you’re solving, and any constraints they must take into account when solving it.
Example: “I need to figure out how to get more leads (problem), but I need it to fit within a budget of $5k/mo, and they must be qualified to an extent that the sales team can close 25% of them (constraints).”
Expect some resistance to come up, and potentially some fear. Push through that, and allow the results of the first experiment to steer your next experiment.
If it works, continue and expand. If it doesn’t work, explore whether the issue was with the approach or with the person you chose to delegate to.
Want to dive deeper?
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