How to delegate effortlessly—and scale faster
“If you want to build a ship, don’t drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”
― Antoine de Saint-Exupéry
What happens when you assign work to one of your people?
Do you tell them what needs to be done and when you need it? Once you’ve done that, can you put that piece of work out of your mind, trusting that your people will deliver? And do you get back what you expected, on time, and without a lot of follow-ups and reminders?
If that’s how it works for you, that’s great. If that’s how it works for every leader in your company, that’s spectacular. You’re going to execute flawlessly, scale effortlessly, and grow your company beyond your wildest dreams.
That’s not what I see most of the time. If you’re like most leaders in the early stages, you default to doing things yourself because it takes longer for you to explain them than to just do them. You have to follow up with people constantly on critical pieces of work. People miss deadlines and miss the mark with what they give you. You’re working longer hours with less to show for it. You’re on your people’s last nerve. It’s burning you out, and it’s entirely avoidable.
You’re bad at delegating.
Relax—you’re not alone. Almost everyone struggles with this—but almost no one talks about it. Among the people I work with (primarily founders of early stage companies that are tilting from building to scaling), problems with delegation are one of the biggest friction points on the growth curve. They slow you down and they keep you smaller than you could be.
They’re also much easier to solve than you might think. You can work much less at this and get much better results—effortless performance. Here’s what that could look like:
This is how simple delegation can be
Dave was a master at delegating.
I had started working at a consulting firm early in my career—early enough that I knew a lot of technical things but largely missed the nuances of culture and politics. Dave was later in his career and had worked at some really impressive companies in really powerful roles. Working for Dave was a great education in the game of business beyond its obvious rules. This was especially true of achieving more through a team.
When we had a deliverable or a challenge with a client, Dave would welcome me to his office, mention the situation, and ask what I thought we should do. Then he listened.
This was a little disorienting to me. Dave had had plenty of success and responsibility in a career that spanned decades. He had worked for and with business giants whose names you would know. I was a handful of years into my career and could barely manage a coffeemaker.
As Dave would listen, I learned to describe what the situation was (in facts rather than opinions), where there were problems, and what I thought needed to happen. This would usually culminate in a description of what a good outcome looked like.
When I had described the situation, Dave might ask a couple of questions about what would happen as a result of this outcome or make a suggestion here or there, but he expected me to come to the meeting with a fully baked understanding of problem and solution.
Once we had that, Dave would ask when that outcome needed to happen. I would suggest a deadline and discuss anything that could change that deadline. Dave might ask a “what about…” question or two, and we would agree on a due date.
With the outcome and due date agreed, Dave would ask, “what help do you need for this?” I would either decline help or ask for a specific resource or resources. Dave would nod.
At this point (usually no more than 5-10 minutes into the conversation), Dave would restate the outcome, the due date, and help needed precisely as we had discussed them. Then he would smile and say, “We’ll look forward to seeing (outcome) on (due date). Let us know if you need anything to make that happen. We’re all counting on you.”
And I’d leave to get to work. Meetings with Dave never lasted more than 15 minutes. People rarely missed deadlines (and never more than once). Our work was high quality, and it almost always led to repeat business. Dave was never stressed, and people worked their butts off to deliver for him. We didn’t keep our commitments out of fear of Dave.
We didn’t want to let him down.
How Dave did it
Can you imagine what it would be like if your people delivered every time because they didn’t want to let you down? I’ll explain in a moment how Dave did that, but first let’s take a look at what he did:
He invited me to describe the situation and what needed to happen.
He asked me what date to put against that outcome.
He asked me to clarify any help I might need.
He confirmed in my words what we had agreed.
He said, “We are counting on you.”
This is dead simple. It’s also deceptively clever.
Dave was the leader, but he asked me to describe what we were doing, why, when, and with whom. I learned to show up prepared to address those questions. I knew he would ask, and I knew he wouldn’t answer them for me. In effect, Dave delegated by getting me to manage myself. He knew an important point about motivation:
People support what they help to create.
He also knew something else: if I sign on to the outcomes and timing of a piece of work, I’m invested in it. I’m far more likely to do what I’ve decided to do rather than what someone else decided for me. When he was restating what we had agreed, he was actually confirming and validating my decision.
There’s one last essential piece: “We are counting on you.” My thinking and decisions were mine (with light shaping from Dave), but my commitment wasn’t just to myself or even to Dave. There was a whole team that needed me to keep my commitments, which were actually our commitments. The thinking was mine, but the accountability was ours.
What Dave did here is what I teach leaders to do: delegate effortlessly and effectively without appearing to do a damn thing.
Dave got results. The firm grew, clients were happy, we won new business and repeat business, and when people pulled long hours, they did so enthusiastically. If you didn’t understand what Dave was doing, though, you might miss how simple and brilliant it was.
How you can delegate better and scale faster
“The best executive is the one who has sense enough to pick good men to do what he wants done, and self-restraint to keep from meddling while they do it.”
– Theodore Roosevelt
Here’s where you’re causing yourself work and worry: you’re trying too hard.
Almost every leader I work with tends to try to have all the answers, give people clear instructions, and spend countless cycles trying to keep track of what’s been assigned and what’s due. You don’t have to work that hard.
The real magic in delegation is that it works better when you work less.
Strong leaders are secure enough to trust both the process and their people. You picked the people around you because of their dedication and their savvy. When you ask them to bring the thinking, you let them shine. When you give them a structure for proposing how they organize their work, you help them come to the best answers. When you let them know the team’s counting on them, you open the door for them to be leaders.
This is hard for some of us. If we’re not being seen to be creative, hard-charging, and… you know… “leaderly”, then what’s our real value? As a leader, though, that’s the point: you are the conductor, not a member of the orchestra. If you’re the smartest person in the room, you’re in the wrong room. To paraphrase a wise observation, real leaders don’t create followers—they create more leaders.
When you do that, you remove a huge barrier to growth: you. You stop making yourself a bottleneck. Instead of making yourself essential, you focus the team on the work. Leaders who can’t do this hit growth limits beyond a couple dozen people. You see this when you see the pattern of “I’ll just do it myself” or “I can do it faster than I can tell them how to do it.” That’s toxic and limiting.
Leaders who get themselves out of the way see more of their vision become real without having to do the doing part. This is magical, and it is powerful. It’s one of the things I see in the best and fastest growing teams.
This simple tool will change your leadership and your company. It’ll unleash the genius in your team—but it only works if you can give up the need to tell people what to do and “hold them accountable”. Let them tell you what they’re going to do, and let them hold themselves accountable. They’ll almost always surprise you with what they can do.
And when they don’t? That’s where it’s your turn to shine as a leader.
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