Why Most Entrepreneurs Fail at Delegation (and How to Fix It Fast)
- Layne Martin
- Sep 29
- 2 min read
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Delegation is one of those skills every entrepreneur knows they should master… yet most fail at it. If you’ve ever found yourself thinking, “If I want it done right, I’ll do it myself,” you’re not alone.
I’ve been there. Early in my leadership at Sourceress, I swallowed that familiar idea hook, line, and sinker. I barely delegated anything—unless I absolutely had to. When I did, I swung between extremes:
Throwing people in the deep end with minimal guidance, then panicking when the results weren’t up to par.
Micromanaging every step, giving instructions so detailed that I might as well have done the work myself.
It was exhausting and completely unsustainable.
A 2015 Gallup study underscores that many entrepreneurs struggle with delegation due to a reluctance to relinquish control, leading to micromanagement and unclear expectations. This often frustrates employees and hinders business growth. By setting clear expectations and fostering psychological ownership, entrepreneurs can improve delegation outcomes.
The turning point for me came when I stopped focusing on “how I would do it” and started focusing on who was on my team and what they were good at. I learned to:
Identify strengths – Every team member has natural superpowers. Find them and lean in.
Elevate high-potential individuals quickly – Invest time in coaching the people who can grow fast (and are ready to do so); they’ll return it tenfold.
Iterate and collaborate – Instead of perfect instructions, I worked alongside my team to refine results, letting them take ownership while I guided the process with regular input.
It should feel like teamwork, not like you're trying (and failing) to get other people to do it exactly how you would've.
Once I found this sweet spot, delegation stopped being a chore. Projects ran smoother, my team felt empowered, and I had the bandwidth to focus on the work only I could do.
A study published in 2024 examines the relationship between delegation and leadership in software management. The findings suggest that effective delegation, coupled with transformational leadership styles, can improve workflow, enhance team motivation and productivity, and ultimately lead to successful project outcomes.
Quick Wins for Better Delegation Today:
Stop giving exact instructions; start giving outcomes and context.
Play to your team’s strengths, not your comfort zone.
Check in early and iterate—don’t wait until the final product to see results.
Invest in coaching high-potential individuals—they’ll multiply your impact.
Delegation isn’t just a leadership skill—it’s a business multiplier. Stop doing everything yourself, and watch your team—and your results—soar.
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