204: "How To Coach Through The Delegation Mess" ft. Alli Murphy

Delegation doesn’t go wrong because you delegated. It goes wrong because something underneath was already broken, and now you can see it. The real work for a senior leader is to respond in a way that protects trust while helping your people solve the problem on their side of the table.

🧭 Conversation Highlights

• Delegation often reveals process, skill, or expectation breakdowns that were already present, especially when you assign “new-to-them” work.
• Don’t confuse urgency with control: jumping in too aggressively can damage trust and make people afraid to take the next opportunity.
• Use a conversation to coach: get curious, ask open-ended questions, clarify success, and help them build their own repeatable approach.
• In high-pressure moments, you may need to help or provide options, but preserve agency so the person learns and owns the outcome.

💡 Key Takeaways

• Treat delegation failures as “visibility,” not proof of incompetence. The flashlight was just overdue.
• Protect trust while solving the problem. If the person feels vulnerable, your response can either build safety or shut it down.
• Your goal is repeatability, not just getting the current project finished. Empower the person to solve it again in the future.
• When you must intervene for timeline or stakes, do it in a way that still keeps the person in charge of choices and next steps.

❓ Questions That Mattered

• What “rats or spiders” are showing up when delegation isn’t working, and what breakdown is actually underneath it?
• What does success look like to you, and where do we meet versus where do we miss?
• How do we enhance trust so the person can ask for help and learn instead of hiding mistakes?
• When urgency forces you to step in, how can you still preserve the person’s control and ownership?

🗣️ Notable Quotes

• Delegation is just finally revealing that those things were going wrong the whole time.
• The problems were already there, and now you can finally fix them.
• If you can remember that the person you're leading in this situation is vulnerable, and if you insert yourself aggressively back into it, you will tear to shreds whatever trust you might have been b u
• The next time you delegate, you'll have a lot more confidence because you went through that with them.

🔗 Links & Resources

• Listen To Other Episodes Co-Hosted With Alli
• Check out Alli's Skool Community