The Progress Loop: The One Email That Helps Founders Work With Advisors
The 6-Part Structure That Replaced All My Advisory Zoom Calls
When I became an advisor for the first time, I told the founder to call me whenever he needed anything.
He took me literally.
For the first 6 months I heard nothing. Then one Sunday night my phone rang at 10pm. He was in a cash crisis and needed a connection to a lender by morning. I helped him, but I kept thinking: I could have seen this coming 3 weeks ago if I had known what was actually happening.
That is when I understood how most founders think about their advisors. They only reach out when they need something. And the rest of the time they do not want anyone to see how stressed they actually are. Projecting calm is part of the job, but it means your advisors are flying blind, and the moments they could have helped you avoid become the Sunday night phone calls instead.
The fix is something I now call the Progress Loop.
It is a short update email you send every 2 weeks to your advisors, your investors, or anyone who is genuinely in your corner. Write it weekly for yourself. Send it every other week to them.
Write it weekly because the business moves fast and the reflection keeps you sharp. Send it every other week because unless your advisors have a meaningful equity stake, weekly starts to feel like a chore for everyone.
The Progress Loop does 3 things a quarterly Zoom call never will:
It creates a paper trail of your own thinking over time.
It shows your advisors you are doing the work, not just reporting on it.
It forces you to get honest with yourself before you have to get honest with anyone else.
The Structure of the Progress Loop
I have worked and reworked this format for 10+ years. Here is exactly how it works. (You can feed this into Ai and it will just do it for you)
1. Activities
Write down what you actually did, not what was on your roadmap.
If you spent 3 weeks in enterprise sales conversations and your stated strategy is product-led growth, a good advisor will spot that gap. You probably will not, because you are living inside it.
2. Wins
Show your progress.
Wins give advisors something to reference in future conversations and build an archive you will want when you are fundraising and someone asks what you have built.
3. Learnings
Your job as a CEO is to systematically reduce risk in your business.
The format that works:
We used to think X was true.
By doing Y, we found out X was wrong.
What is actually true for our business is Z.
For example: We used to think that getting a meeting with the VP of Sales meant we were close to a deal. By running 12 of those calls, we found out the VP almost never owns budget in companies under $50M. The actual decision maker is the CFO, and we had never spoken to one.
4. Stuck
Stuck does not mean things are hard.
Most founders skip this section because writing it feels like admitting they are failing. As an advisor, this is the first section I read, because helping remove 1 real blocker is worth more than 10 strategy conversations.
Write it as questions you are trying to answer:
How do we hire the VP of Sales we actually want when we cannot afford his base comp?
How do we produce quality content without building a full media team?
How do we find out if the new product roadmap is something clients will actually pay for?
Specific questions get specific help.
5. Focus for the Next 2 Weeks
Write down what needs to be true for you to have a good 2 weeks. Meaning, what are you going to get done before the next update?
When people you respect know what you have committed to, you organize your week differently. You do not want to show up to the next Progress Loop and explain why you did not do what you said you would.
6. Help Us With
Every Progress Loop is a small sales pitch.
Your ask has to connect directly to something already in the update. If what you are asking for has nothing to do with what you have been working on, what you learned, or what you are stuck on, it is probably not your real priority right now.
The full Progress Loop format:
Activities: what you actually worked on
Wins: proof of progress
Learnings: what changed about how you see the business
Stuck: the constraint
Focus: what needs to be true in the next 2 weeks
Help us with: a specific ask that connects to the above 5
Here is how to start:
Write the Progress Loop this week.
Send it every other week.
State the facts. Tell the truth.
If you know a founder, business owner, or entrepreneur send this to them. They will thank you for it.
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