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Why do I struggle with delegation?

Discover six common ways leaders sabotage their team’s productivity – and what to do instead.

Delegation is a key skill for any leader. 

Whether you’re a solopreneur, CEO, corporate manager, or small business owner, you have to be able to transfer ownership of a task to someone else.

Why is good delegation so important? 

Well, it’s the secret to leveraging the most precious commodity you have – your time. It’s how you find the freedom to focus on work that creates higher value for your organization and more satisfaction for you.

Of course, that all sounds great on paper.

But in the real world, lots of leaders struggle to delegate. You might…

  • Believe it’s faster and easier just to take care of something yourself
  • Not fully trust someone else’s judgment or skill level
  • Feel guilty about assigning tasks to already-busy team members 

All of these things are normal – but it’s also critical that you work through these issues.

Until you learn how to delegate, it’s almost impossible to grow as a leader.

You’ll get bogged down in tasks that don’t really move the needle for your organization. And worse, you’ll eliminate key opportunities for others to take on new responsibilities and grow. 

My friend Larry Bossidy, the former CEO of Honeywell, has the perfect way of expressing the risk of not being a good delegator. He says, “If you take the joy of the decision away, you take the joy of the job away.”

I don’t want that to happen to you and your team! 

So to help, I’m going to outline the six most common reasons people struggle to delegate – and then share what you can do to improve. 

Keep reading and see how you can free up both yourself AND your team to get big things done together.

Mistake #1: You’re operating with the wrong mindset.

Like so much in leadership, successful delegation starts with the right mindset. 

One of the most important shifts you can make as a leader is to stop using a “boss” mindset and start using a “coach” mindset.

Bosses tell you what you're supposed to do. But a great coach helps you figure out what you're supposed to do.

Imagine if Steve Kerr, the head coach of the Golden State Warriors, saw a player miss a shot and decided to run onto the court to take his place in the lineup. That’s a ridiculous notion, of course – and that’s because coaches understand that their place is on the sideline. 

So if you tend to struggle with micromanaging or not letting go of a task, a coaching mindset will help you resist the urge to hover and instead trust your team to execute.

On the other hand, let’s say you tend to turn people loose on a task without much preparation. A coaching mindset will help you, too. 

After all, no coach would tell their team to go out and play a game without first providing them with the right equipment and training! 

Make the shift from “boss” to “coach” in your mindset and you’ll have a whole new way to approach delegation.

Mistake #2: You’re delegating the wrong tasks.

You can't delegate effectively if you don't understand your own strengths and weaknesses. 

First, take some time to reflect on what you’re good at and what you struggle with. What tasks bring you joy? What skills do you lack that others on your team already have (or want to develop)?

Next, consider your role in the organization. What tasks can you do that no one else can? How do you create the most value and impact?

When you understand your own strengths and high-value tasks, you’ll have a clear understanding of which tasks you can successfully delegate and which ones you need to keep doing yourself.

Mistake #3: You’re not providing clear direction.

Once you have identified tasks to delegate, now it’s time to give your team members clear direction for those tasks.

Be specific about what you want them to do. They need to know the expectations, deadlines, and any constraints or limitations. Don’t assume they’ll know what to do or how to do it. 

Then, help them understand how the assignment ties into the overall organizational goals. What larger context can you provide to show why this assignment matters? 

I love how Lauren Hobart, the President & CEO of Dick’s Sporting Goods, applies this big idea. She calls it “commander’s intent.” 

Here’s the idea:

When you delegate, you don’t simply lay out the tasks. You also share the reason behind them. 

“If you paint the vision,” she explains,” [the tasks] may not work out exactly the way we planned – and they never do! But if you know what the vision is, the smart people on the ground can adapt.” 

Have your prior delegation efforts crashed and burned with poor results, miscommunication, or delays? If so, pay attention to this part of the process. Make sure you give your team members clear direction – both for the task at hand and for how it fits into the overall strategy.

> Catch my whole conversation with Lauren Hobart on this episode of my podcast, How Leaders Lead, and don’t forget to subscribe!

Mistake #4: You aren’t equipping your team. 

Delegation also means giving your team members whatever they need to do the job. Do they need access to certain tools or software, permission to make decisions, or the authority to spend money? 

Consider their skillset, too, and proactively equip your team members with whatever additional training they need to succeed.

If team members don’t have the resources they need to do their job, they will become frustrated. 

Plus, they’re less likely to succeed at the task you’ve given them, which will create more frustration for you, too.

Too often, over-eager delegators make the mistake of skipping this step. Don’t wait for your team members to ask for what they need. Be intentional and equip them well, right from the start.

Mistake #5: You’re micromanaging.

Think about what it really means to delegate. You’re not asking someone to do the task for you.

You’re asking someone to own that task themselves.

When you delegate a task, that’s a vote of confidence in the team member you’ve assigned it to. You’re communicating to them that you trust them and believe in them. 

And that’s why nothing will derail your delegation efforts faster than micromanaging. 

If you constantly check in with them and review every detail of their work, you’re undermining that “trust” with your actions. 

This creates a culture where people don’t feel like they’re trusted to do their jobs effectively. It stifles creativity and can lead to burnout as people feel overwhelmed by the scrutiny. 

Be mindful of circumstances where you’re more likely to micromanage or struggle to fully let go of a task. It’s often the places where we’re most concerned about quality or have more experience ourselves.

Mistake #6: You’re not creating accountability.

Clearly, nobody wants to be a micromanager. And perhaps that’s why so many leaders make this sixth and final mistake.

To avoid coming across as overbearing, they neglect to create any kind of oversight or boundaries at all.

But you can’t have successful delegation without having accountability, too.

Start by creating clear metrics and goals, so your team members know what success looks like and how to measure it.

Then, create a clear process for accountability toward those goals. 

Stephen M.R. Covey calls this “smart trust.”

When you extend trust as a leader, you don’t do it blindly or without judgment. Instead, you create clear expectations and a process for accountability.

“You don't have to hover over and micromanage them,” Stephen says. “They come to you, saying, ‘I'm going to be accountable. Let me tell you how I'm doing against the expectations we agreed upon.’” 

Make it easy for your team members to be transparent about their actions, decisions, and outcomes. Create a plan for regular communication, so they have a clear channel to account for their progress.

This ensures your team members are on track and that they understand what is expected of them. And, if they aren’t meeting those expectations, you’ve got an open line of communication to support them and help them improve.

> For more on this concept of “smart trust,” listen to my full podcast episode with Stephen M.R. Covey, on How Leaders Lead.

When you eliminate common delegation mistakes from your leadership game, you’ll not only free up your own time. You’ll also unleash everyone else on your team to grow and develop.

In fact, the best leaders consider the development of other leaders as one of their primary responsibilities. 

They know that the best way to grow their businesses is to create an organization full of great people who know how to make big things happen. 

And that’s exactly what being a successful delegator will help you do.

What tips and tricks can you share from your experience delegating? Drop a comment and bring your wisdom to the conversation.