As we grow in our careers, we first become individual contributors, then managers of individuals, and then managers of managers. That transition is a tough one, and one that comes very quickly in startups. A bit flips and a leader must begin to delegate. Delegation is the only way a leader of a team or company develops leverage in the organization.

A good friend told me about a Vanity Fair interview with former President Obama.

When asked about the stress of his days, he replied:

But if you happen to be president just now, what you are faced with, mainly, is not a public-relations problem but an endless string of decisions. Putting it the way George W. Bush did sounded silly but he was right: the president is a decider.

Many if not most of his decisions are thrust upon the president, out of the blue, by events beyond his control: oil spills, financial panics, pandemics, earthquakes, fires, coups, invasions, underwear bombers, movie-theater shooters, and on and on and on. They don’t order themselves neatly for his consideration but come in waves, jumbled on top of each other.

“Nothing comes to my desk that is perfectly solvable,” Obama said at one point. “Otherwise, someone else would have solved it.

So you wind up dealing with probabilities. Any given decision you make you’ll wind up with a 30 to 40 percent chance that it isn’t going to work. You have to own that and feel comfortable with the way you made the decision. You can’t be paralyzed by the fact that it might not work out.”

On top of all of this, after you have made your decision, you need to feign total certainty about it. People being led do not want to think probabilistically.

That’s effective delegation. He’s focused only on the work he is uniquely positioned to complete and exceptionally good at.

I wish I had been taught how to delegate effectively. I’m not sure why this part of management wasn’t a component of the business school curriculum, but it should be. Here’s why:

The management team of a company is a decision-making and productivity chokepoint. Critical decisions flow through them. If the management team ruminates on most decisions, the company’s progress stalls. In a 100 person startup, five slow-to-decide executives limit the productivity of 95 employees. In a 1000 person startup, the ratio might be 10:990. There’s enormous leverage in a hierarchical organization if the leadership moves quickly. The converse is equally true. Sluggish decision-making halts all progress. link

There are a few good resources on delegation. Peter Drucker argued good decisions have four parts.

1. The name of the directly responsible individual, or DRI; something Apple did well
2. A clear deadline
3. A list of people who would be involved, and communication plan
4. A list of people who would be affected, and communication plan

That’s the first step. Deciding what to do and who to do it.

The second part is refraining from deciding how to do it.

Define the what but delegate the how. Great delegators decentralize decision making. John Boyd talks about the importance of decentralized decisions in Certain to Win. They key concept is the OODA loop (Observe, Orient, Decide and Act). There are lots of benefits to this. Speed is the most obvious. This management style engenders trust by creating space for others to be creative and grow. It opens up the solution space to novel ideas.

The last part is measuring success and creating a culture of transparency and honesty. Any number of frameworks will work including OKRs or weekly stand-ups. The critical part is only getting involved at a deeper level if the team isn’t executing.

Delegation is a critical skill for every leader. Without it, leaders become bottlenecks and slow down everyone in the business, limiting the success. With it, leaders empower people and develop tremendous leverage from the organization, and the company becomes much more than the sum of its parts.

Photo by Maksym Gryshchenko on Unsplash