There are three pieces to this built on top of one another:

1. A recurring cadence

2. AI-generated notes to prep your exec ahead of the performance check-in

3. A self-assessment prompt sent to each direct report ahead of time

Let me walk through each one.

Part 1: Set the cadence, and make it automatic

The single biggest reason performance feedback doesn't happen is that nobody blocks time for it.

This is because it falls squarely into Quadrant 2 of the Eisenhower Matrix: it’s important, but not urgent.

When something is important but not urgent, it’s always, “This is something I should do at some point, and it’ll be valuable, but we have more important things.”

As a result, we spend so little time on Second Quadrant work, even though this is the work that makes the most difference in our performance. (I’ll probably write another newsletter issue about this someday - it deserves its own write-up!)

Here’s what to do:

1. Set up a recurring calendar event every 6 to 8 weeks. I like 6 weeks for newer teams or teams going through a lot of change, and 8 weeks for more established teams where things are relatively stable.

2. The calendar invite should go to the CEO or manager, not to the direct reports.

3. This is their reminder to kick off the process, NOT the check-in meeting itself.

If you're an operator setting this up for your exec, you can also use an AI assistant like Claude Cowork to track:

1. When the last round of check-ins happened

2. Flag when it's time for the next one

Set it up with a Scheduled Task that recurs on your chosen timeline.

When it runs, it should notify the Exec and the Operator that supports the exec (a CoS or EA) that it’s time to perform reviews.

It should also reference the last time reviews were done, and tell you how many weeks ago it happened.

That way, even if the calendar invite gets snoozed or moved, someone (or something) is keeping track.

Part 2: AI-powered prep notes

When it's time for check-ins, the exec needs to walk into each conversation with actual, specific observations about that person's performance.

The frustrating part of performance reviews is that execs usually know what they want to say to their teams, but:

1. They need help organizing that information, and

2. A lot of that information slips out of mind by the time you’re ready to do performance reviews

We can solve this problem by using AI.

Here's how to set that up:

1. Pull up every meeting transcript between the exec and their direct report from the last 6 to 8 weeks.

   1. If you're using a tool like Granola (or whatever AI notetaker you have running in your meetings), those transcripts are sitting there waiting to be used.

2. Then, ask your AI assistant to review those transcripts and pull out two things:

   1. What's going well. Specific moments where the person showed strong judgment, delivered something great, or stepped up in a way that mattered.

   2. Opportunities for growth. Patterns where they could be doing more, areas where they seemed stuck, or things the exec has had to repeat more than once.

3. Ask AI to assemble all of that into a clean list and send it to the exec on Slack (or whatever messaging platform you use).

4. Ask the exec to:

   1. review it

   2. make edits

   3. add a 1 to 5 rating for each person, where 3 means "meets expectations." (More on the rating scale in a minute!)

The whole point is that your exec shouldn't have to sit down and try to remember six weeks of interactions from memory.

The transcripts already captured it. Let the AI do the heavy lifting of synthesis so the human can focus on the actual conversation.

Part 3: The self-assessment prompt

In addition to what the Exec has to say about their Direct Report, they should be given the opportunity (and prompt) to self-reflect.

Again, you can automate this with an AI agent (Claude Cowork can do this, or you can set it up as a simple scheduled message in Slack or email).

The message looks something like this:

There are two things I love about this framework:

1. It forces calibration.

   1. When you ask someone to rate themselves on a 1 to 5 scale and then ask what would move the number up, you bypass the vague "things are fine" response.

   2. People have to get specific. And more often than you'd expect, people are harder on themselves than their manager would be, which opens up a really productive conversation.

2. It makes feedback bidirectional from the start.

   1. You're not just evaluating them. You're asking them to evaluate you.

   2. That changes the entire dynamic of the conversation.

   3. It signals that you actually want to get better too, and that this isn't a one-way judgment call.

The best way to teach your team that feedback is a gift is by demonstrating that you view it as a gift, too.

Want more operational content?

Check out Coaching Founder for downloadable Notion templates and write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner, daughter, and dog, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.