Troubleshooting Your First Delegation: How to Learn, Adjust, and Try Again
In our last post, Putting Clarity Into Practice, we walked through how to take your first step toward delegation, moving from sorting and prioritizing to actually handing off a task. If things didn’t go perfectly, you’re not alone. This post will help you troubleshoot, adjust, and build confidence for your next attempt.
You took the leap and delegated (or automated) a task, but maybe it didn’t go as planned. That’s more common than you think, especially for business owners and leaders used to doing it all. The good news: every imperfect attempt is a chance to build real delegation skills, and we’re here to help you troubleshoot, adjust, and delegate with confidence.
Why First Attempts Are Rarely Flawless
Letting go of a task, even a small one, can feel awkward or frustrating. Maybe you picked something you weren’t ready to hand off, or the results didn’t meet your expectations. That’s normal. Delegation is a skill, not a one-time event, and getting it right takes practice and honest feedback.
Real-World Example: Delegating Calendar Management
Let’s say you asked your assistant to “handle your calendar.” You expected a smoother week, but instead, you found your days overbooked and some urgent meetings clashing with less important ones.
What happened?
You didn’t specify which meetings were high-priority or which ones could be rescheduled.
Your assistant did their best, but without clear direction, treated all events as equally important.
There wasn’t a system for flagging urgent vs. flexible appointments.
This is a common scenario, not a failure of ability, but a gap in expectations and communication.
Troubleshooting Checklist
Review:What exactly didn’t work? Be specific; was it timing, details, communication?
Feedback:Have a direct conversation with your assistant. Ask what was unclear or challenging from their side.
Clarify:Rewrite your instructions to be step-by-step. Use examples: “Schedule client calls before noon. Block Fridays for admin. Mark board meetings as ‘must keep’ and networking calls as flexible.”
Choose again:If calendar management was too big, start with delegating only one type of meeting or a daily task.
Set a check-in:Schedule a 10-minute review after the first week to discuss what’s working and what needs to change.
Practical Tips for Stronger Delegation
Start small, then expand:Pick a low-stakes, repeatable task before handing off bigger responsibilities.
Document your preferences:Create a quick reference guide or checklist for the task.
Encourage questions:Make it clear you want your assistant to double-check rather than guess.
Give feedback early and often:The first few handoffs are learning opportunities for both of you.
Celebrate small improvements:Acknowledge progress, even if it’s not perfect yet.
How to Confidently Try Again
Don’t give up if your first attempt wasn’t perfect. Use what you learned to delegate a similar or smaller task, or revisit the original with clearer instructions. The more you practice the easier and more effective delegation becomes.
You Don’t Have to Do It Alone
Delegation is a skill that grows with every attempt, and even imperfect steps move you forward. If you have questions, need support, or want to share your experience, leave a comment or reach out. We’re here to help you delegate with clarity and confidence every step of the way.
