How to Delegate the Right Way

Think of everything you could get done if your team operated on a higher level.

Imagine being able to delegate some of your daily responsibilities so you could focus on more important priorities and strategic goals. How less stressful would your workday be if you didn’t have to tell people what to do all day?

As CEOs, when we’re feeling stressed or overwhelmed and things aren’t getting done, our natural reaction is to step in and take control.

This makes us feel better and can be effective in the short term. But what ends up happening long-term is your team continually looks to you for direction. They don’t own the projects – you do! This stifles growth, profitability and keeps you from doing what you’re supposed to be doing as CEO.

So what’s the solution? How do you get out of this self-sabotaging routine?

Start delegating some routine tasks that are keeping you from doing more high value work.

Now, I realize some of you may be thinking, “Sure, sounds great. But my team’s barely able to keep up as it is. There’s no way they’re going to be able to take on any more responsibility. I just don’t have enough “A” players.”


But you may have more “A” players than you think. Maybe you just haven’t given them a chance to prove themselves.

If you start delegating the way I recommend, you may find you have some hidden gems on your team who are just waiting for the opportunity to prove themselves.

On the other hand, you may be trying to delegate but you still aren’t getting the results you’re looking for.

If so, are you delegating projects in such a way that allows you to be strategic with your activities and priorities? If not, perhaps your approach to delegating could use some polishing.

Delegating vs. Telling People What To Do

I see many CEOs who don’t really understand what it means to delegate effectively. It’s a learned skill that can take some trial and error to master.

But like most business skills that have to do with people, having proper mentoring can make all the difference. I know in my case, learning the ropes in the corporate world, I was exposed to a variety of leadership styles, some of which were much more effective than others. But if you’ve grown up in a family business, this may not have been the case for you.

Either way, there’s a difference between delegating and telling people what to do.

When you’re telling people what to do, you’re still at the center of the project with people coming to you for decisions and directions pretty much every step of the way.

Delegating the right way means trusting people to do what they’re supposed to do – including solving problems and overcoming challenges along the way. It doesn’t mean they won’t ask questions or want your opinion, just that your response isn’t about “doing,” it’s about guiding and teaching.

Here’s my approach to delegating more effectively:

  1. Trust comes first.
  2. Start delegating slowly, but make it something meaningful.
  3. Check in to gauge progress.
  4. When people fail – and they will fail – don’t overreact.
  5. Turn failures into teaching moments.
  6. Over time, assign projects of greater importance.

Let’s take a look at each one for some key points to remember:

Trust comes first:

Trust that your people want what you want – to successfully complete a project and do their job to the best of their ability. Trust that it’s not their intention to let you down. Trust that they want your trust and confidence in their work.

Start delegating slowly, but make it something meaningful:

By that I mean, hand off something that is taking up a significant portion of your time or takes a lot of coordination – things that keep you from doing other, more important work.

Think of routine tasks that don’t necessarily need to be done by you – just someone who is capable. For example, putting a timeline together to manage a critical project or coordinating the expectations of a vendor presentation.

NOTE: When you’re delegating any project, make sure your expectations are clear regarding cost, scope and deadlines. Make sure the person understands what you want the final result to look like. For example, it’s important to explain if you want a spreadsheet with certain information laid out in a particular way.

After you’re sure the person understands what you’re looking for, set milestones and deadlines for future check-in meetings. But let them determine the best course of action. How they get there is not your issue. As long as it’s legal, ethical and in line with the values of the organization, let them do their job.

Check in to gauge progress:

Meet with the person on a regular basis (about every two to three weeks) to determine how well he or she is doing at each milestone. Be sure to review any specific elements to make sure they’re on the right path.

NOTE: Most of all, be supportive and encouraging. Provide the tools and resources they need and an environment where they can be successful, but resist your natural inclination to take charge. Let them run the project. Let them spread their wings.

When people fail – and they will fail – don’t overreact:

It’s important to keep your anger and frustration in check when people miss the mark.

Yes, I know, there will be issues and, especially in the beginning, everything will take more of your time than if you had just done it yourself. But I promise you that any time you spend helping your team members grow will pay off in spades down the road – for everyone involved.

NOTE: People will make mistakes – just like you did when you were learning the job. You need to be OK with that as a leader. I’m not talking about incompetence. Occasional failures are fine, as long as people are learning from their mistakes.

Be patient. It’s a bit of a learning process for everyone; in fact, one of my clients going through this process recently told me, “This is really hard, but it feels so good to not be involved in every little thing.”

Turn failures into teaching moments:

This kind of mentoring is part of what you should be doing as CEO. Never correct or demean someone in front of others. When things go wrong, meet with the executive privately and discuss what happened.

NOTE: The most important question you can ask when someone fails is: “What would you do differently next time? 

Then, sit back and listen. Offer helpful suggestions and give feedback only when the person is finished. Teach, don’t scold or belittle the person. They already feel bad enough as it is that they let you down.

Observe how the person handles failure and how resilient they are in the face of obstacles. You want people who can think critically and learn from their mistakes.

Over time, assign projects of greater importance:

After the person has successfully completed the first task, assign another project that’s more of a stretch and repeat the process. Observe how they manage this more challenging project. Once again, don’t try to micromanage the process. Give them a goal, be clear about expectations and let them determine the best way to get there.

NOTE: Let people know you believe in them, that you know they can handle it. This will work wonders for their confidence and performance.

As your team gains experience

Go through this process with each of your direct reports and you’ll be amazed at how most people will rise to the occasion. The quality of your conversations will completely change, everyone will be operating at a much higher level and you’ll have much more time to devote to higher value work.

And for those few who aren’t able to step up?

Make a change and find them a role they’re better suited to – better for the both of you and the rest of your team as well.

The bottom line:

Leaders need to lead. Being involved in all the daily activities of your business takes you away from what your role really is as CEO. Delegating effectively frees up your valuable time, builds up your team and allows you to do more of what you should be doing as the leader.

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