How to follow up with your deals

I’ve been reviewing follow-up emails from founders this week.

Most of them are not helping move the deal forward. Instead, they’re coming across as pesky or desperate.

Which is not what you want.

So in this newsletter, I’m going to dive deep into how to send good follow-up emails to your deals for different scenarios.

Table of Contents

• What’s the point of a follow-up?

• Follow-up frameworks

  • Follow-up after a meeting

  • Professional accountability

  • Multi-threaded follow-ups

  • Follow-up after negotiation

  • Procurement Steps

  • Deal gone dark

• Deals get done in follow-ups

What’s the point of a follow-up?

Most founders send stuff like “just checking in.” Or “how are things going?” Or “Do you have any questions?”

Stop doing this. It doesn’t help you, and it annoys the shit out of prospects.

The point of follow-ups is to move the deal forward. Period. There’s no other reason to follow up.

So if your follow-up doesn’t help move the deal forward, don’t do it.

Follow-up frameworks

The reason why follow-ups end up being pesky is that most folks haven’t learned a proper follow-up framework before.

Just like your discovery and demo, you can’t wing this part of the sales process.

And yes, there are better ways to follow up. Here are the general frameworks - we’ll dive deeper into each:

• Follow-up after a meeting

• Professional accountability follow-up

• Multi-threaded follow-ups

• Follow-up after negotiation

• Procurement Steps email

• Deal gone dark follow-up

Let’s get into it.

Follow-up after a meeting

Lots of information gets shared in a meeting. Your job, after a call, is to take a snapshot of all the important information and send it to the prospect.

When you write this email, pretend you are writing it for the people who weren’t in the room. This way it makes it easy for your champion to forward it around. Or later on, you might need to forward it around to someone.

The follow-up emails are much easier to write if you use a discovery framework like FOUNDER. You can learn it from this ebook (use coupon 30OFFMAIL to get 30% off).

The follow-up email must cover:

• The facts you collected about their workflows

• Their objectives and pain

• The impact on the business

• Any negative consequences

• How you help

• Next steps and action items

Here’s a sample email:

[Subject] SalesMVP: Call + Next Steps

Hey ((First_name)), appreciate the time today. Was interesting learning more about ((company_name)).

Here's the summary, did I get it right?

• You run a B2B sales process. Targeting real estate, development, architects, etc. Trying to get one building, then their entire portfolio.

• You want to increase deal flow. You have a VA who scrapes real estate publications to identify accounts. You cold email via lemlist + zappier/airtable. You got Attio as your CRM for opps.

• You're starting to hammer the phones. Trying to do 20 hours a week on sales (last year averaging about 5hrs a week).

• Did 500k in revenue last year (from 2023 efforts). You said you got lucky, didn't run a lot of sales/prospecting.

• You've recently hired folks to handle the production stuff, freeing up a lot of your time for sales.

• You need help with workflows and how to best organize those 20 hours of prospecting. You don't have a proper flow yet.

• Without a structured sales process, you can’t forecast more than $250k in revenue this year. You want more predictability so you can grow.

• Through 1:1 coaching, we'd work through some of this. Typically, we go through areas where you're struggling, try to figure out why stuffs not working, then come up with a plan. Sometimes we'll practice (like cold calling scripts, DMs/messaging teardowns, etc). You take what you learn and go apply it, then we troubleshoot what's working vs not.

Couple ways to get started - we could look at twice a month or weekly coaching, depends on how fast you want to move and what's your budget. You're swamped with onboarding right now, but March could be a good time to start if you're interested.

I'll ping you in a couple weeks to see if you're ready.

Talk soon,

Dan

This summarizes the conversation we had, and the next steps we discussed. Also gives ammo for how to follow-up next.

Professional accountability

After you’ve sent a summary email, your next follow-ups should be about holding the prospect professionally accountable to what they said they would do.

This is how you avoid the “just checking in” scenario. And ends up being way more impactful to you and the prospect.

The way you do this is you ask them a question they could only answer if they actually did the thing they said they would do.

There’s different ways you can do this.

Let’s say the prospect said they need to “talk to the team” after a demo - this scenario happens a lot. How would you follow-up with this?

I’ve seen folks send all sorts of annoying stuff to try to get this unlocked.

But what they don’t send is a what/how/when question, which is powerful for moving the deal forward.

So if you have “we need to talk to the team.” The logical follow up would be “what concerns did the team have when you talked to them?”

This does a few things:

• It holds them professionally accountable to what they said they would do. You’re still checking in on it, but in a better way.

• They could only give you an answer if the meeting actually happened. So this prompts them to go talk to the team.

• The “what concerns” invites trouble, which is a good thing. There are always concerns about vendors. Knowing what they are helps you navigate them. So go find trouble.

• If they say they haven’t talked to the team yet, then you can say “when is that meeting scheduled?” There’s a logical path to keeping them professionally accountable. If they had the meeting, they’ll answer you, which you then use the info to ask your next question to help move the deal forward.

Never check in again - it does nothing. Always ask questions that hold them accountable to things they said.

P.S. only ask one question at a time. Keep it really simple. Whatever question is most likely to help move things forward or uncover trouble, ask it. Nothing else.

Multi-threaded follow-ups

In the event that you had a meeting with multiple people, you need to send two sets of follow-ups.

The first is your meeting summary, which goes to everyone. Do not ask clarifying/probing questions to a group. Nobody will answer. Just send the summary as a snapshot so everyone has the same information.

Then the second set of follow-ups is sending 1:1 emails to each of the participants, with something relevant to them specifically.

The reason you want to do this is that B2B sales cycles are complex, and usually have 5-7 people involved in a decision. Everyone needs to agree on the same problem, a viable solution, then you as the best solution. That’s a lot of consensus building that needs to happen.

The more threads you have within the deal, the higher likelihood of closing. When I was VP Sales at Proposify, we used Gong to analyze our sales cycles. Our win rate when we had 1 thread in a deal was 16%. Our win rate when we had 3+ threads in a deal was 43%. Significant difference.

So the way you do this - first send the summary email to everyone.

Then, pick out the key people from the call. Who are the important folks who will make a decision. And who are the skeptics. Those are the folks that need extra attention from you.

Then send something that was relevant to them, their role, or something they said on a call.

If someone found a specific workflow in your demo really compelling, send them an email with a couple other use cases for the workflow.

If someone was a bit skeptical or confused about your reporting, then send them a quick video explaining how the reporting works and ask any clarifying questions.

If someone’s in charge of implementation/integration, send them your docs and ask about how they’ve implemented similar things in the past.

The point is here, everyone has a specific role in making the decision. You can make this a lot easier on them by having 1:1 communication threads specific to their requirements.

The plus side - if your champion suddenly leaves, you don’t have to restart the deal. You have other folks who were involved.

Or if someone goes dark on you, then you can pick it up with whoever is answering you the most.

The more threads you have, the better.

Follow-up after negotiation

Let’s say you’re pretty far into a sales cycle. You’ve gotten confirmation from them to move forward. They’ve agreed on price and terms.

There’s a specific email you need to send at this point with all the key terms of the deal.

This is separate from a meeting summary email, so both might happen at the same time. But send them in two different emails to make it clean.

Here’s an example of what to send:

Subject: ((product)) proposal

((First_Name)),

Please find attached a link to the proposal. As agreed, it is for ((solution/product/bundle)) at ((amount)) and it offers a ((%%)) price adjustment if we receive the paperwork by ((date)). If not, the adjustment will be ((new price/adjustment)).

I’m available at ((your phone number)) if you have questions. If I don’t hear back from you by ((date)), I’ll give you a call. In the meantime, I’ll send along relevant info.

Thanks,

((My.first_name))

This sets everything that needs to happen in one short email. The champion can forward this around to whoever needs to sign the deal. All of the terms should be outlined here.

Procurement Steps

For a lot of B2B cycles, there’s going to be a bit of project management to do after the demo.

A “steps” email can be super helpful to help the deal move along.

Again, send this as a separate email from the meeting summaries.

What this email does it outlines all of the stuff that needs to happen on your side and their side to get the deal done.

Best way to do this is to figure out their go-live date - when do they want to be up and running. Then reverse engineer the different steps that need to happen from today until that date. Include stuff like kickoff call, onboarding timelines, contract signature date, legal review, budget approvals, security, etc. Outline all of it, and add tentative dates.

Then send it to your prospect and ask if it’s reasonable to get this done on those timelines. They might say yes or no. If no, then it gives you a chance to adjust, add whatever’s missing, and reset your expectations. If yes, then it gives you and your champion a plan of action.

Here’s what an email could look like:

(Subject) Acme go-live timeline

Hey Tracy, I put this schedule of events together to keep both of us on tract.

Does it seem reasonable to you?

• Go-live date May 20

• Kickoff date April 20 (need 1 month for onboarding and training)

• Contract signature date April 15

• Legal review April 13

• Security review April 11

• Budget approval April 8

Is there anything missing from this that you’d add?

Talk soon,

(My_firstname)

This type of email helps create a plan to keep the deal moving forward.

Deal gone dark

The most important type of follow-up email you can send is the summary after the call. And make sure you have details on the pain in there.

Because those emails create a snapshot of your understanding. And ideally the prospect confirms that everything is right.

So when the deal suddenly goes dark, you have a way to bring it back to life.

And you do this by replying to the summary email, and asking a simple question.

“Hey Tracy, are you still on track to hit your goals?”

This framing has gotten 100s of deals unstuck for myself, my sales reps, and founders I’ve coached over the years.

The key to getting a deal that’s gone dark to move forward is to make it all about them, and what they said they wanted to do.

Again, coming back to professional accountability.

Are YOU still on track - that’s about them.

To hit YOUR goals - that’s about them.

The deal will never get done for your reasons, on your timeline, as a founder. It will only get done on their reason, and their timelines.

So the best way to get them unstuck is to remind them of what they said.

And that’s why you have to send a detailed follow-up after every meeting. Because at any point, the prospect can go silent on you.

Deals get done in follow-ups

When I was analyzing deals as VP Sales at Proposify, we noticed that the more interaction we had via email, the higher likelihood the deal would close.

When prospects confirmed we got our email summaries right. When they got back to us on accountability questions. When we multi-threaded. When we sent procurement steps/timelines and asked if it was reasonable.

Those were all signals that the deal was progressing.

When my sales reps forgot to send follow-ups. Or their follow-ups were random instead of rooted in a framework, deals stalled.

And when the prospects didn’t engage at all with our follow-ups, it was a pretty clear indication that the deal wasn’t going to happen.

So don’t discredit those simple emails - they’re way more powerful than you think.

Let me know what you think of the newsletter, or what topics you’d like me to cover. Always appreciate hearing from you :)

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