Before we get started…
On Tuesday, November 10th at 1 p.m. CT, I'm hosting a free live webinar called Chaos to Clarity by Christmas.
In 90 minutes, we'll map your entire 2027 on one page, pick the 3 to 5 January projects that actually matter, and set the rhythm that lets your team run the plan without you (including the plan you're about to hand over to an AI and ask it to destroy…more on that in a minute)...
…so you can actually step away over the holidays.
Ok, onto this week's article…
"2027 is going to be OUR year!!!"
Look, I get it…
You want 2027 to be a BIG year. We all do.
And if you’re anything like me, at some point in the next few weeks, you're going to sit down with your team and build "The Plan" that gets you there.
But here's the problem:
Annual planning is New Year's resolutions for entrepreneurs.
They're fun to make and they feel great in the moment, but they're usually abandoned by the second week in January.
And not because the plan is stupid or bad. It’s because nobody pressure-tested it while there was still time to make a change.
(It's just too much fun to talk about all the things that could go right, so nobody wants to be the "jerk" bringing up all the things that could go wrong.)
So this year, we're adding an extra step to our planning process…
It's called the Pre-Mortem Protocol, and it's an AI prompt that tells you exactly how your plan is going to fail before you ever execute it.
Here's the copy-and-paste prompt:
Here's the plan I'm about to roll out to my team:
[Paste your plan: the targets, the initiatives, who owns each one, and the assumptions underneath them. The more specific you are about your numbers and your constraints, the harder this works.]
It is 12 months from today. The plan failed. Your job is to tell me why it failed.
Do not hedge. Do not give me a balanced view. Do not give me a list of risks. Write the story of the failure three separate times, once for each of the three ways a plan dies.
FAILURE 1, EFFORT. The plan was sound, but nobody ran it hard enough or long enough. Write the post-mortem of a year where the work happened at a fraction of the intensity the plan assumed, or got abandoned before it had time to produce anything. Name the initiative that lost its hours first and what took them. Say which dial failed: intensity or duration.
FAILURE 2, EXECUTION. The plan was sound, but one or more critical resources was missing. Write the post-mortem of a year where the team did the work and still failed because something procurable was never procured: a hire, a tool, an integration, a budget line. Name the missing ingredient and the month it became obvious. If you cannot name something specific and buyable, say so instead of guessing.
FAILURE 3, ASSUMPTION. The plan itself was wrong. Write the post-mortem of a year where the team did everything right and it failed anyway, because something underneath the plan turned out not to be true. Say which kind it was: a belief that was already false the day we wrote it, or one the world made false afterward. Name the assumption, name what it actually became, and name every downstream number it broke.
Each failure gets its own section, 150 words max, written in past tense as though it already happened. Specific names, specific months, specific numbers from my plan.
THEN, RANK THEM. Which of the three is most likely, given what you can see in my plan? Cite the evidence from the plan itself: how many initiatives there are, how they're spread across owners, which assumptions I stated and which ones I left silent. One paragraph.
THEN, THE EARLY WARNING. For the failure you ranked first, name the one metric that would show it in the first 90 days, and the number on that metric that means it's happening. Not a vague indicator. A number I could put on a scorecard this week.
THEN, THE CHANGE. Name the changes we should make to this plan before I present it to my team. Tell me what to cut, move, reassign or rewrite, and what it protects, in order of importance based on the potential negative impact and the ease of the fix.
Don't soften any of it. If the plan looks fine to you, tell me which part you couldn't find evidence for and ask me for it.
Here's why it works…
It Argues With Your Plan, Not a Generic One
If you give AI a generic goal like, "We want to do $12M next year…"
…you’ll get a generic (and generally unhelpful) reply.
So give it the whole plan, including:
Your metrics targets (with the actual numbers)
The initiatives you plan to greenlight
Who owns each one (by name)
The assumptions underneath the targets (i.e. what you believe about project timelines, team capacity, hiring goals, and key metrics like cost per lead, close rate, churn, etc.)
That last bullet (assumptions) is the one everybody skips, but it's also the one that gives you the best feedback and insights. DON'T SKIP IT!
SIDE NOTE: Here's an article I wrote on our strategic planning process if you want to see how we do it.
It Only Allows Three Answers
If you ask AI "what could go wrong," you'll get a dozen bullet points and zero decisions.
So the Pre-Mortem Protocol forces it into the only three ways a plan ever actually dies. (By the way, I broke these down in the Mid-Year Reset issue back in July.)
Failure of Effort. The plan is right, but nobody worked the plan hard enough (intensity) or long enough (duration). If the plan was never fully set in motion, you have an effort problem… not a planning problem.
Failure of Execution. The plan is right, but one or more critical ingredients was missing. The test is whether you can finish this sentence: "This would be working if we had ____." If the blank is a person, a tool, an integration, a budget line, something you could go buy, then the plan was never the problem… you simply couldn't execute it.
Failure of Assumption. Everybody did everything they were supposed to do, but the plan still failed. Maybe you assumed last year's cost-per-lead number would hold into this year, but ad costs skyrocketed and threw things off. Or maybe you assumed you'd be able to buy raw materials at one price, but then new tariffs made that price jump by over 50%. Whatever the cause, the team did everything they could, and the scorecard still says they lost. This is the one that stings the most, but it happens… and it's important to call it what it is. The failure wasn't with effort or even execution… the failure was in the assumption. Because sometimes crap just happens.
Three failures, three different responses.
Effort means double down without touching the plan.
Execution means keep the plan and find the missing piece.
Assumption means the plan itself has to change…
…which is why the ranking matters more than the list.
It Has to Pick One
AI is a world-class fence-sitter…
It'll give you a laundry list of things that could go wrong, wish you luck, and call it analysis.
That's why the Pre-Mortem Protocol has to rank its suggestions and show its work using your own plan as the evidence.
It Lets the Robot Be the “Jerk”
Nobody on your leadership team wants to be the Negative Nelly who says, "Here's how this falls apart…”
…so let the AI say it instead. No politics, no career protection, and no group think.
Then make the change while there’s still time to do it… before ego and sunk cost bias have reared their ugly heads.
⚡️ Action Step: Before you present your 2027 plan to your team, paste it into the Pre-Mortem Protocol and discuss the proposed changes it gives you. If you haven't built the plan yet, save this email and make it a part of this year’s planning ritual.
Give it a shot and let me know how it goes…
-Ryan
Ryan Deiss
Co-Founder and CEO, The Scalable Company
P.S. The Pre-Mortem Protocol tells you where your plan breaks, but Chaos to Clarity by Christmas is where you work out which 3 to 5 projects to run in January instead.
That's what we're building on Tuesday: your entire 2027 on one page, the January projects that actually matter, and the rhythm that keeps your team running the plan without you.
It's free, it's 90 minutes, and everyone who registers gets the replay.
Quick Hits
The best of what I read, watched, and clicked this week…
📈 Growth
One company had 80% of its marketing budget in radio and no idea what it was buying (Owned and Operated)
A Dallas guy still collects checks for dishwasher repair videos he filmed a decade ago (Girdley's Letter)
27 years of marketing, boiled down to 5 books (Instagram)
One $14 baby food ebook, 99 more just like it, and $250K a year (LinkedIn)
Your sales manager just gave you an ultimatum (YouTube)
💰 Money
He lost $1 million on the deal his own lawyer told him to walk away from (Built to Sell Radio)
5 bank accounts, 1 schedule, and a fat check to the owners every 90 days (LinkedIn)
The gap between a $5M and a $20M business often comes down to one dashboard (Instagram)
⚙️ Systems & Ops
Annual plans are too long to predict and too short to matter. Here is the 3 year, 90 day fix (YouTube)
He paid $1.4M for a one man garage business and became the one man (Acquiring Minds)
Count your real work days before you plan the quarter (I only had 16) (Business Lunch)
The 2007 article that invented the pre-mortem, and why nobody speaks up in planning meetings (Harvard Business Review)
🛠️ Tools & AI
Set the 3 year number, then work backward 12 quarters (12Q Planning Canvas)
The decision criteria that stop your team asking you for every answer (Clarity Compass)
Give the AI your Slack, Gmail and CRM and let it do the follow up (Lindy)
