Read Time: 5 minutes.
If you’re a manager with 3+ years of experience and want better systems so you can level up as a leader, the last cohort of our MGMT Accelerator for 2026 starts Tuesday, October 6 at 11 AM ET.
Three years ago, Issue 1 of this newsletter shipped a free expectations template.
Thousands of you downloaded it. We teach it in every live cohort. And I can tell you exactly what happens next, because I've watched it hundreds of times.
The first attempt to fill out this template takes over an hour.
What’s the right level of responsibilities?
What if I don't have a metric for this?
How much detail is too much?
The template isn’t the problem. It’s 5 columns you’ll understand immediately.
The problem is applying the new skill you just leaned. It felt clear when you read about it, but actually performing the trick is hard. That difficulty creates friction. And friction is what causes good intentions to fall back on old habits.
“I’ll come back to that later” you think.
You won’t.
So in class, I don't hand people the template and walk away. I ask questions.
What does this person actually own?
When you’re frustrated with someone doing this role, why is that?
What number tells you if they’re succeeding?
After 10-15 minutes they get it. But that doesn’t scale. I can’t spend that time with thousands of readers.
Which means every playbook you've ever learned has the same gap. You left with the idea. You did not leave with the coach, the partner who can help ensure you put it into action.
Now you can.
If you’re a leader looking to level up your skills, you’d be crazy not to embrace this process.
Step 1. Find your source.
Find an article, blogpost, podcast transcript, anything that gives a clear articulation of the skill you’re trying to build.
If you're stuck, use one of mine. Expectations is the first thing we teach in the Accelerator because everything downstream depends on it: feedback, 1:1s, reviews, promotions. The template from Issue 1 is still free. Open it.
Step 2. Load it up.
Open Claude Cowork. Drop in the sources and any relevant content you have on the first case. For our expectations example, I’d include things like: the job description, last quarter's review, their own draft if they wrote one, even a personality test.
Then paste this:
I'm setting expectations for [name], who [role] on my team. Attached are the template and what I have on the role. Before you draft anything, interview me the way a good coach would. Ask one question at a time: what this person truly owns, what below the bar and above the bar look like by [date], which number I'd actually check, and where I'm unsure. Ask follow-on questions if my answers are vague. When you have enough, draft the full card in the template's format. Flag any row where you had to guess.Use voice mode to answer if you can. It’s three times faster than typing and you'll say things you'd never type.
Why this matters: you just did the hard part of applying the skill the way you'd do it with me in the room. Except it took twelve minutes and AI produced an 80% draft for you.
Step 3. Coach it up.
Eighty percent is not done. It's a first draft from a new hire.
There are two ways:
Iterate in the chat. Don't open a new chat. Correct it in place. "Row 2 is too soft, she owns the number, not the process." "Collapse rows 4 and 5." "The Above column reads like a stretch goal from a deck. Make it something I'd notice."
Edit the drafted document. Make your changes directly. Then load the finished version of the template back into the chat. Have it compare your final version to the draft and extract lessons from the differences.
You’ve done two things. Applied this new skill to the first case. But more importantly, started training AI on the rules it should use to apply the skill on your behalf.
Step 4. Package it.
This is the step that makes it 10x. Most people stop at step 3, close the chat, and start from blank again in April.
Don't save the output. Save the method. Same rule as onboarding any new hire.
Paste this:
Turn what we just did into a reusable skill called Set Expectations. Before you write it, play back the spec in my words: the trigger, the inputs, the interview questions to help me draft it, the corrections I made and why, and the output format. Ask me anything you're unsure about. Then save it so I can run it for anyone on my team. Every run must ask before it assumes. If the output ever feels generic, tell me what input is missing instead of filling the gap.In Cowork, that saves as a skill you can call by name. You would type forward slash / and the name, in this case Set-Expectations.
In Chat, save it as a project instruction. Either way, the questions I'd ask you in class now live in your AI.
Why this matters: the corrections you made in step 3 mirror your judgment. It’s how the baseline skill I taught you becomes your new leadership skill. And how you start from that skill level the next time you set expectations as opposed to starting from scratch.
Step 5. Compound it.
Next hire. Next quarter.
"Run Set Expectations for Priya." You load the inputs. Or better yet, you’ve setup connectors so it finds the input for your. It asks the questions. You answer. You get a draft. You decide.
Every iteration comes closer to matching your intentions.
Learning a playbook gives you 2x return. Running it is how we get to 10x, 50x, even 100x. Our MGMT Accelerator is four weeks of live coaching helping you learn and apply proven playbooks. Join us. The last cohort for 2026 starts Tuesday, October 6 at 11 AM ET.
Bonus. Grade it.
Most leadership skills result in an interaction.
The feedback.
The coaching.
The decision.
In this case, you set expectations. The template was just the method for aligning on the information. The real goal is a contract between you and your team member. Record these conversations. Have you skill evaluate the transcript and make adjustments so they land better next time.
Expectations is the example. Any playbook works.
Try it on the one you've been meaning to run: 1:1 prep, delegation briefs, the quarterly review, the feedback you owe someone.
The test is the same.
Did it give you 80% of what you would have created? Then it's working.
Did it hand you something way off or too generic? Give it that feedback so it can give you what you need.
Most leaders collect playbooks. The ones keeping up with today’s growing demands are building them with AI for unprecedented leverage.
Give it a shot this weekend, and let me know how it goes.
Lead on,
Dave & Mar
PS - The MGMT Accelerator starts Monday, October 6 at 11 AM ET. Twelve hours live over four weeks, with templates for everything we build in class and coaching on your single biggest management problem. You leave with clear profile and expectations for every person on your team, so you’re never telling them to "be more strategic."
More than 1,500 leaders have graduated and said it was worth 25x what they paid.
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