The Rule of Threes

Most sales follow-ups dies in week two.

You send the proposal. You call on Tuesday. You chase up on Friday. Maybe a third time the following Wednesday, with a slightly wounded "just circling back" tone. Then nothing. The prospect goes quiet, you get busy, and the deal quietly slides into your pile of dead deals with the others that nobody touches...

The other failure mode is the opposite. You follow up so rarely that when you finally do, the buyer genuinely can't remember you. "Sorry, which proposal was this?" is not the reply you were hoping for.

Neither works. And both are incredibly common, including in MSPs that are otherwise very disciplined about process.

Real deals take longer than your patience

Here's the uncomfortable bit. Big deals have long sales cycles. Not six weeks. Not a quarter. Sometimes years.

The buyer isn't ignoring you because they don't care. They're ignoring you because their contract with the incumbent has 14 months left to run. Or the CFO just put a hold on any discretionary spend. Or the person who championed you went on parental leave. Life happened to the deal, not you.

The sellers who win those deals aren't the loudest. They're the ones still politely, quietly present when the timing finally lines up.

A while back I was helping one of our team coach a business owner who'd stopped following up on proposals altogether. Not because he was lazy. Because he didn't want to be "that pushy salesperson."

I get it. But I'll put it to you the way I put it to him. That prospect gave up their time. They sat through the discovery meeting, told you their problems, and waited while you built a proposal. Following up isn't you chasing a sale. It's you respecting the time you both invested. And if you go quiet, the buyer doesn't think you're polite. They think they were too small to matter.

The cadence I use came out of years of working with sales teams, on deals where the cycle genuinely ran two to three years. That's why "once a year for three years" isn't a typo or exaggeration. One of those teams closed a $500,000 deal by sticking to it. If they hadn't, we'd have lost it. Not to a competitor. To silence.

That's the whole argument for the Rule of Threes.

The cadence

It's simple enough to remember without writing down, which is half the point:

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Once a week for three weeks. Once a month for three months. Once a quarter for three quarters. Once a year for three years.

Twelve touches. Roughly four years. It ramps down naturally, so you're present when interest is fresh and still around when it's not.

Early on, the gaps are short because the proposal is top of mind and there are usually real questions to answer. Then the gaps stretch. By the quarterly stage you're not chasing a decision, you're maintaining a relationship. By the yearly stage you're the person who remembered them, which is rarer than it should be.

It keeps you in front of the buyer without being the salesperson they mute.

How to actually run it

The cadence is the easy part. Running it is where it falls over. Four rules make the difference.

1. Schedule the whole thing the day the proposal goes out.

Not "I'll remember." You won't. Nobody does. The same afternoon you send the proposal, load all twelve touches into your CRM as tasks with dates. If it's not in the system, it doesn't exist.

This is also why the rule works for teams, not just individuals. When a BDM leaves, the cadence doesn't leave with them.

2. Every touch needs a different reason.

"Just checking in" twelve times is not a cadence. It's a slow-motion nag.

Each touch should give the buyer something. A new insight. A case study from a similar business. A relevant article. A genuine check-in. An anniversary of the original conversation. Something that makes opening your email worth their 20 seconds.

3. If they say "talk to me in six months", honour it exactly.

Set the reminder for six months and one day. Not five months because you're keen. Not seven because you forgot.

Hitting that date precisely tells the buyer something important: you listened, and you're reliable. That's the exact quality they're buying from an MSP in the first place.

4. Keep it short.

Two sentences and a question. That's plenty.

Nobody wants a four-paragraph "touching base" essay. Short messages get read. Short messages with a question get replied to.

How AI helps takes the pain out of it

Here's where it gets practical for anyone reading this newsletter.

The hard part of the Rule of Threes has never been the maths. It's rule two. Coming up with twelve genuinely different, genuinely useful reasons to get in touch with one prospect is tedious. Across a pipeline of 30 open proposals, it's 360 messages. That's why people default to "just circling back."

This is exactly the kind of work AI is good at.

When a proposal goes out, I give Claude the context: who the client is, what they care about, what we proposed, any objections from the meeting (straight from the Fireflies transcript if I've got one). Then I ask it to draft the full twelve-touch sequence, each with a different angle, each two sentences and a question.

What comes back isn't perfect. It's a first draft. But it's a first draft of twelve messages in about a minute, each with a distinct reason to exist. I tweak the voice, swap in a real case study where it's suggested a generic one, and load them into the CRM tasks. The whole cadence is built before I've finished my coffee.

A few things I've learnt doing this:

• Give it the transcript, not your summary. The buyer's own words about their problems produce much better follow-up angles than your recollection does.

• Ask for variety explicitly. Tell it you want a mix of insight, proof, check-in and anniversary touches. Otherwise it drifts towards twelve polite versions of the same email.

• Draft the later touches later. The weekly and monthly messages can be written on day one. The yearly ones should be refreshed closer to the date, because the world (and their business) will have moved on.

• You still hit send. The AI drafts. You adjust it and make it yours. You own the relationship. A human who knows the client reads every touch before it goes.

  
  

The result is consistency without the grind. Which is the whole reason most follow-up fails in the first place.

The quiet advantage

Most of your competitors will stop following up somewhere around week three. That's not a guess, it's what happens in nearly every MSP pipeline I look at.

Which means by month four, you're often the only one still there. By year two, you're definitely the only one still there. When the incumbent finally drops the ball, or the contract comes up, or the new IT manager starts asking around, guess whose name is in their inbox from last quarter.

Persistence isn't glamorous. It doesn't need to be. It just needs to be scheduled. Sales for MSPs is a long game, you don't win, if you don't play...

One thing to do this week

Pick the most recent proposal you sent that's gone quiet. Today, load the full Rule of Threes cadence into your CRM for it, all twelve touches, with dates. Then ask your AI tool of choice to draft the first three.

That's it. One proposal. Twelve tasks. Fifteen minutes.

Then see who replies in month four.