The Delegation Feedback Loop

Delegation's value isn't only in task completion — it's when your assistant is able to anticipate needs and nails the output. Getting there requires a system for candid, consistent feedback paired with ruthless iteration.

A tight feedback loop is the only way to transform your assistant from a task-taker to a true extension of yourself.

Here's how it plays out:

• Beginner delegators say "Thanks, everything looks good" or “Change XYZ” with no further explanation.
• Intermediate delegators say “Thanks for drafting those emails. The main points are clear, but we need to work on making the tone warmer. Try reading it aloud — does it sound like something I'd say in person?”
• Advanced delegators say “Great start on the investor email. I've created a decision tree in Notion for investor queries—please use it to revise these drafts. Then, create a 'Quarterly Investor Comms Playbook' with templates, key metrics, and guidelines for common scenarios. We'll refine together to create a repeatable process for future investor comms.”

To make this more tactical:

1. Highlight specific wins: "Your handling of the client's concerns in the second paragraph was very tactful. You addressed the issue without being defensive. That matches my voice perfectly.”
2. When providing critical feedback, define what A+ would look like instead: "Instead of restating my executive summary from the last board deck, an A+ investor update draft has the same overview structure but incorporates the most updated data we have at the time of writing. For example, when we open with key metrics (ARR, Retention)—they need to be from our most recent dash from the lead PM.”
3. Transform one-time feedback into a repeatable standard way of operating when possible: “The email drafts are a great start. I've annotated them with comments — and recorded a Loom walking through my thoughts line-by-line. I'd like you to create a 'tone and style guide' based on these notes and your observations of my communication. Once we refine the guide, we'll use it as a living doc to improve our ongoing email drafting process.”
4. Set up feedback triggers: "Let's have a quick feedback chat every day at 4 PM about one task you completed. For example, after you've scheduled a series of meetings or compiled a report. Also, ping me for a 10-minute debrief right after you handle any client calls or finish drafting important emails so we can refine our process in real-time.”

Remember: Feedback is compound interest on your delegation investment. The more consistently you contribute to the relationship, the greater your returns.