Hello {{First name|Predictable Revenue community}},

Community update: our next Revenue Roundtable is May 8th (next Friday) at 930am PT, we have a 2 more spots. Hit me back if you’re interested in joining.

Next newsletter: I was at a conference/trade show this week trying to connect with future customers for ReplyLoop - let me know if it’d be interesting to hear about my approach to booking meetings before the show, what I did at the show to meet folks, and how I’m handling my follow ups.

Onto the newsletter…

Most founders ask for a sleepover on the first date.

I had a call last week with a founder I've been advising. He's brilliant, builds great product, has real customers, and writes terrible emails. Being transparent, he doesn’t write many because he doesn’t send many… yet. We were going through his nurture pipeline together, looking at people he'd talked to over the last year that hadn't converted. He wanted to reach back out so I asked him to draft an email.

The draft was fine, until the last line. "If this is interesting, do you have time for a call?"

That's where most founders blow it.

Asking for a meeting is the email equivalent of asking someone to come back to your place. It's the biggest commitment in the conversation. You don't lead with it. You don't tack it onto the first message after a long silence. You build to it. And most people reach for the meeting ask because it's the only one they know how to write.

There's an entire range of asks between "hey" and "got 30 minutes this week?" Most founders just don't know it exists.

Before we even get to the asks themselves, the bigger reframe is this: not every nurture email needs a CTA at all.

I wrote about why your nurture list is your future revenue a while back, and the most important point in that piece is that nurture isn't a single ask sent at the right moment. It's compounding presence. Each touch is a brand impression. If you happen to send one while the prospect is in the middle of thinking about the problem you solve, they'll opt in on their own.

So the lowest-effort, highest-leverage nurture email is the one with no ask at all. You saw an article, you thought of them, you sent it. That's the whole email.

Hey [name], saw this piece on how AI is changing top-of-funnel for B2B SaaS. Made me think of our conversation last spring. Hope all is well.

No calendar ask. No "let me know if you want to chat." Nothing for them to push back on. Just a small reminder that you exist and that you remember what they cared about. Send enough of those and one day a reply comes in that says, "Funny you sent this. We just started looking at this again."

That's the email that turns into a deal. Not the one with the CTA.

When you do have something to ask for, the question is how hard to push for it.

A hard ask goes straight for the meeting. "Got 15 minutes Thursday?" It works great when you're confident the answer is yes. Someone inbounded to you. They just told you they're ready to buy. You had a great conversation last week and they asked you to follow up. In those cases, anything softer wastes their time and yours. Just book the meeting.

A soft ask is what you reach for when you're not sure. You haven't talked to them in a year. They went quiet on you. You're reaching back out cold. In those situations, going straight for the meeting is asking the other person to make a commitment before they've decided they care. So you ask for something smaller instead. An opinion. A reaction. Confirmation that the topic is still relevant. Something they can answer in a sentence without opening their calendar.

The mistake most founders make is sending hard asks when they should be sending soft ones. They reach for the meeting because that's the only move they know. And then they wonder why their reply rates are so bad.

Match the ask to your confidence in the yes. When the timing is right, push hard. When it isn't, push soft and let the conversation tell you when to escalate.

The softest version doesn't ask for a meeting at all. It asks if the topic is even relevant:

Hey [name], I'm taking on a couple more GTM advisory clients this quarter. Is finding more pipeline top of mind for you right now?

(Yes, I know you see what's happening here. I'm using a newsletter about email writing to write an email to you. The cheek of it. Stay with me.)

There's no calendar invite, no "got 15 minutes," nothing for them to schedule. You're just checking if the topic is alive in their head. If they say yes, you've opened a door. If they say no, you've saved yourself the awkward follow-up.

A step up from that is asking for an opinion:

Hey [name], I'm working on something new in the GTM advisory space and I'd love your feedback on it. Worth a quick chat?

You're asking for time, but you're framing it as a feedback ask, not a sales ask. The subtext is, "I respect your judgment, not your wallet." People love giving opinions. They're much more likely to take a meeting where they get to be the expert than one where they're getting pitched.

The hard ask is the one most founders default to:

Hey [name], I have one open slot for GTM advisory. Past clients have used it to build their first outbound motion or hire their first AE. Want to grab 15 minutes to see if it's a fit?

That email says, "I'm selling something, you know I'm selling something, here's what it is, want to talk?" Nothing wrong with it when the timing is right. But it only works when the person already knows you, already trusts you, and has probably already had some version of this conversation with you before.

The other lever you have, separate from how hard you're pushing, is how much context you're working with.

A high-context follow-up is one where you know something specific about their situation. They told you they were going to raise a round before they'd consider buying. Or they needed to close one more customer first. Or they were waiting on a hire. You don't need to invent an excuse to follow up. You just ask how that specific thing is progressing.

A low-context follow-up is the opposite. You don't have anything specific to anchor to, so you're reaching for "just checking in" energy.

I covered this at length in How to Master the Next Action, so I won't rehash it here. The short version: high-context follow-ups convert at five to ten times the rate of low-context ones, and the only way to send them is to capture the right detail at the end of every conversation. Always end with: "What needs to change for this to become a priority? When should I check back?"

If you don't have that detail, that's fine. Send a content share. Don't fake context you don't have.

One more tactical thing. Your subject line should summarize the intent of the email.

If a subject says "interview request," there had better be an interview request inside. If it says "quick question," it had better be a quick question. The subject line is a contract. Break it and the reader marks you as a spammer in their head, even if they don't unsubscribe.

When in doubt, "quick question" is the safest subject line ever written. Specific enough to feel personal, vague enough to fit almost anything, and it lowers the perceived effort of opening the email.

The reason this matters isn't that founders are bad at writing emails. It's that founders who didn't come up through sales only have one move. The hard ask. They reach for it because they don't know other moves exist.

If you're not a natural salesperson, the answer isn't to get better at the hard ask. It's to learn to push softer when you're not sure of the yes, send the no-ask emails ten times more often than you think you need to, and let the conversations come to you.

Most of the people you've talked to in the last twelve months are not ready to buy from you today. But a lot of them would happily read an article you sent. And those touches compound.

So go look at your inbox. Pull up the last twelve months of conversations that didn't close. Send three of them an article. Ask one of them if the topic is still on their mind. See what comes back.

And if your opinion happens to be that you could use some help with your GTM motion, I have one slot open. You know where to find me.

Collin

PS - Thanks for putting up with the cheeky ad for my service throughout this one. I try and keep it light and not too pushy, let me know how I did.