Here’s something I’ve learned over the last 30 years working with entrepreneurs and being one myself: People who start businesses tend to have dominant personalities. And dominant people like being in control.

So what?

Well, here’s the problem: At some point, that do-it-all person will have to stop doing and start delegating. At the very least, they’ll have to shift what they’re doing and delegate the things they used to do. Otherwise, they’ll begin to feel like they’re on a hamster wheel — doing what they’ve always done but suddenly getting nowhere.

Making that shift is challenging. In fact, it’s one of the most difficult transitions that I’ve seen founders go through. It’s also one of the most important.

Effective delegation

When people talk about delegation, they’re often referring to the simple act of assigning a task to someone else. Perhaps you can imagine a staff meeting where the boss says something like, “Mary, you contact all the vendors about their set-up needs. Bruce, you keep track of ticket sales.”

In truth, effective delegation covers more than that.

When you delegate, you take your accountability and authority and give it to someone else. If you hand over the task without handing over the accountability to complete that task and the authority to make decisions regarding it, the delegation will be useless and perhaps even destructive.

If Mary contacts the vendors but can’t make any decisions about the use of the space, has she saved the company any time? If Bruce keeps track of ticket sales but doesn’t feel any responsibility for whether they’re high or low, are the company’s goals being advanced?

If they both know that, in the end, the boss will monitor everything and make decisions about how to proceed, how attentively will they complete their tasks? Struggling bosses tend to discount people and rescue them.

A 2017 Harvard Business Review article on delegating explained it this way:

“You need to be more essential and less involved. When you justify your hold on work, you’re confusing being involved with being essential.

[Being more essential and less involved] means shaping the thoughts and ideas of others instead of dictating their plans, having a sought-after perspective but not being a required pass-through, and seeing your own priorities come to life through the inspired actions of others.”

So what does it take to effectively hand over your accountability and authority?

First, you need someone to delegate to.

Second, you need to know what you’ll do with all that time you get back.

See: 7 Characteristics of Effective Leaders

Who do you delegate to?

Delegating to the wrong person is a common mistake, especially for first-time CEOs.

An employee’s ability to handle one type of responsibility isn’t always indicative of their ability to handle a different type of responsibility. Yet that’s often how organizations work. “You were an excellent engineer, so you’ll definitely be good at managing the team of engineers.”

Plus, leaders often delegate many projects in one fell swoop with a big promotion. A leader gets completely overwhelmed with all the things they have going on, and hands over a huge load to a promoted employee. If they’re not the right person for the job, the costs of failure are high.

Instead, finding the right person should involve a long-term plan and a continuous focus on professional development for your team.

When I used to bring on a new coach, I had a three-step plan for getting them started. First, they observe me coach. Second, we coach together. Third, I observe them coach. We discuss and address questions and concerns throughout.

If I brought on a new coach and just handed them a client, the risk of potential problems would be much higher. By allowing time for a measured, joint process, we see small issues before they turn into big ones.

How do you let go?

While people sometimes make mistakes and delegate to the wrong person, the hardest part of delegating actually comes next.

The piece that really stumps people is accepting that the person you’re delegating to may not do things the way you did. True delegating means letting them do the work any way they decide to do it.

Let’s say you’re delegating for a customer service role. You’ve agreed on two major goals: moving to a two-hour response time for customer service requests and achieving a net promoter score of at least 20.

Now they’re responsible for figuring out how to make that happen — without a bunch of backseat driving from their leader.

It goes without saying (but I’m going to say it anyway) that you’ve already provided clarity about your broader goals and how you make decisions (core values) within the organization. When leaders aren’t clearly communicating their values and goals, they often end up trying to exert subliminal control over projects they’ve “delegated.”

An ineffective leader delegates tasks and then micromanages them. They may mask opinions by asking questions. “Did you consider creating a team of five instead of a team of three?” That’s not a question. That’s a leader trying to take back authority for how a project gets handled.

They may position themselves as a pass-through authority on even small decisions. For instance, a manager may delegate a large project but require authorization of any spending over $1,000.

And let’s be clear: entrepreneurs, especially scrappy ones, do a lot of things that aren’t exactly in their wheelhouse. Delegating to someone else could mean getting something done better than how you would’ve done it.

See: Is Your Company Culture Undermining Your Success?

Delegation as succession planning

I often talk about delegation as succession planning because that gets at the real reason behind delegation. You don’t delegate just to say you’ve done it. You delegate to your successor. You delegate so that you can move out of, up, and into other roles within or outside your organization.

In my time at CDNOW, which I wrote about here, I moved from VP of Engineering to CEO of a $150M company in three years. I was able to do that largely because I was delegating from the very beginning. When the company leadership came in and asked me to take over another department, I had trained someone to be ready to take over my existing responsibilities. When it happened again, I’d already created a leadership team that could take over as I moved up.

Had I not delegated early on, I wouldn’t have had those opportunities. And on a broader scale, without my participation in that growth, the company may not have traveled the same path.

I’ve said for years that working yourself “out of a job” is the best thing you can do for your career or your business. You’re preparing from the beginning for the evolution of your role.

See: The Best Growth Strategy is to Make Yourself Dispensable

When you need to delegate

When I start coaching a business owner, I ask them what they want from their personal life. For an entrepreneur, personal life is always intertwined with business life, so I want to help them align and integrate their goals.

Often their goals are associated with freedom — of time, of money, of choice. We figure out the specific elements of their personal vision, and then we align the company around it. If they only want to spend 25 hours a week in their business, or put $10M in the bank, or they want to retire in 5 years, they need to plan for that goal.

Delegation is what allows a business owner the freedom to work part time, to exit their company, to grow bigger, to give back to the community, etc. Entrepreneurs and business owners that aren’t delegating end up being operationally focused, “stuck in the trenches” as we call it.

And if that’s the case, then who’s being strategic? Who’s looking at the market, the customers, the partners, the investors? In order to have a bigger, broader perspective — an outside-in perspective — they have to pull themselves out of the trenches.

So the time to start delegating is immediately. At the very beginning, entrepreneurs and business owners need to think about how to architect that freedom into the structure of their business.

Final thoughts

Do you have time for all the big-picture strategy thinking and planning you want to do in your business? Do you have time for your family? Do you have time for a vacation?

If you answered no to any of these, congratulations! You are in a great position to start delegating. If you haven’t been thinking about it since Day One of your business, you may have some catching up to do. But the longer you put it off, the worse things will get.

Start delegating (or at least planning to delegate) yourself out of a job today, and you’ll be putting yourself on a path towards more growth and a better experience.

Reach out to us. We’ve helped dozens of entrepreneurs create more freedom by learning to delegate.