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How to Delegate Like a CEO: 5 Mistakes That Are Keeping You Stuck – The Fail To Win Podcast Episode 277
Home » Blog » How to Delegate Like a CEO: 5 Mistakes That Are Keeping You Stuck – The Fail To Win Podcast Episode 277

How to Delegate Like a CEO: 5 Mistakes That Are Keeping You Stuck – The Fail To Win Podcast Episode 277

March 4, 2025 By fastforwardamy Leave a Comment

Delegation is one of the most difficult skills for entrepreneurs to master. You’ve built your business from scratch, so you know how to to business by yourself… but not how to do it together with others. Hence, letting go of control can feel impossible. But if you’re constantly fixing mistakes, micromanaging, or feeling like no one can do things as well as you, you’re not actually leading—you’re just creating a longer to-do list for yourself.

In this blog, I’m sharing the 5 biggest delegation mistakes entrepreneurs make (and I’ve definitely been guilty of these!) and how to fix them so you can build a team that supports your growth instead of holding you back.

Mistake #1: Fixing Mistakes Instead of Coaching

Your copywriter sends in an email draft, and instead of coaching them through improvements, you just rewrite it yourself. Sound familiar? This habit might feel like the fastest way to get things done, but in reality, it’s keeping your team dependent on you.

✅ The Fix: Instead of taking over, give clear feedback. Use a tool like Loom to walk them through what needs improvement, explain what the result is you’re trying to accomplish and let them improve it themselves. This way, they learn and improve over time, reducing your workload in the long run.

Mistake #2: Delegating Tasks Instead of Results

Many entrepreneurs hand out tasks but never communicate the bigger picture. This leads to confusion, inefficiency, and frustration because your team doesn’t understand the end goal.

✅ The Fix: Instead of giving a list of tasks, delegate outcomes. Make sure your team understands why they’re working on something and what success looks like. When they know the end goal, they’ll start taking initiative and producing better ideas and results.

Mistake #3: Expecting Instant Perfection

You’ve spent years learning your business inside and out, so expecting a new hire to be just as good as you from day one is unrealistic. Many entrepreneurs make the mistake of dumping too much on a new team member and expecting them to figure it all out immediately.

✅ The Fix: Narrow the role when onboarding new hires. Instead of expecting them to handle everything, give them one clear area to focus on. Provide training, feedback, and time to adjust. Over time, they’ll become a strong asset to your business.

Mistake #4: Punishing Initiative

When a team member takes the initiative on something that doesn’t go perfectly, do you criticize them or pull back their responsibilities? If so, you’re discouraging innovation and making them afraid to take action without your approval.

✅ The Fix: Encourage action, even if it’s not perfect. When someone takes initiative, recognize the effort and provide constructive feedback rather than shutting them down. A proactive team is a powerful team.

Mistake #5: Failing to Communicate Clearly

If you find yourself constantly frustrated with your team’s work, ask yourself: Have I actually communicated what I expect? Lack of clarity leads to mistakes, frustration, and inefficiency.

✅ The Fix: Clearly communicate your expectations. Use tools like SOPs (Standard Operating Procedures), checklists, and quality control to ensure that your team understands what ‘success’ looks like.

Final Thoughts: Build a Team That Works With You, Not For You

Delegation isn’t about offloading tasks—it’s about building a high-performing team that supports your vision. When done right, it allows you to step out of daily operations and focus on growth.

🚀 Do you want to learn how to structure your business for growth as you grow to a 7-figure organization? I’ve written down 6 steps that helped me get unstuck in my own business and format my organization for more efficient growth.

Filed Under: Blog, Business, Podcast

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