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Opinion

The Follow-Up Most Reps Never Send

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Photo: Kelsy Gagnebin / Unsplash

Most reps follow up diligently right up until the point it stops feeling comfortable. Three emails after a good discovery call, no problem. One email after the prospect has gone silent for six weeks and you've quietly marked the deal Closed Lost in your head — almost nobody sends that one. Which is a shame, because it's the most useful email in the whole sequence.

Here's the argument: a lost deal is a qualified prospect who has already told you their problem, sat through your pitch, and knows what you cost. That is a warmer contact than anything on your prospecting list. The only thing wrong with them is timing, and timing changes.

What the email actually looks like

It is short, it makes no ask, and it does not pretend the deal is still alive. That last part matters. The reason reps avoid this email is that they try to write it as a rescue attempt, it reads as desperate, and they bin it. Write it as a full stop instead:

Subject: Closing this off

Hi Rachel,

I'm going to stop chasing you on this — I don't think the timing is right and I'd rather not clutter your inbox.

If the reporting problem you mentioned in June comes back up, I'm easy to find. And if it turns out you solved it another way, I'd genuinely be interested to hear how. It'd help me give better advice to the next person in your position.

All the best,

Tom

Two things happen with this email that don't happen with a fourth "any update?". The first is that people reply to it. Removing the ask removes the pressure, and a decent number of prospects will tell you exactly what went wrong: they went with someone else, the budget got pulled, the sponsor left. That's free competitive intelligence you'd never get otherwise.

The second is that you've left the door propped open rather than slammed. Six months later, when the workaround they cobbled together stops working, you are the person they remember as reasonable rather than the person who sent eleven emails.

Then put a date on it

The email on its own isn't a strategy. The habit that makes it work is setting a reminder at the same time you send it — three months, six months, aligned to whatever their budget cycle looked like. When it fires, you're not reopening a dead deal, you're contacting someone whose circumstances have probably changed.

That second touch should also be short, and it should carry something other than your own hopes:

Hi Rachel — you mentioned in the spring that this was parked until the new finance year. That's now started, so thought I'd check whether it's back on the list. If not, no problem, I'll leave it another six months.

Note the explicit offer to go away again. It's not a tactic, it's just honest, and people respond to it better than they respond to enthusiasm.

The fair counter-argument

Someone will point out that this is effort spent on prospects who have already said no, and that the same hour spent on building a better prospect list would generate more new conversations. In a given week, that's probably right — the break-up email is a slow-return activity and it will not save your quarter.

But it compounds. A rep who has been doing this for two years has a list of a few hundred people who know who they are and have no particular reason to dislike them. A rep who hasn't is starting from cold every single Monday. The trick is not to treat it as a rescue mission — if you're doing this because you can't accept the deal is dead, you're not closing the file, you're just hiding from a deal that was never going to close.

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