Good Morning. Anthropic built Claude, which we all know can write a speech in seconds. But now they’re trying to hire a human writer for up to $345,000 a year. Apparently, even Anthropic is getting tired of AI writing. And if you’re keeping score, Anthropic is hiring sales reps, too. Turns out, even the biggest AI company needs humans to write and sell for them. Now, let’s get into today’s Follow Up. (:

Sponsor The Follow Up | Subscribe

Harry Stebbings says it took 53 attempts to get Marc Benioff on his podcast.

At some point, you have to wonder whether you’re getting a yes or a call from his security team.

Harry got the interview.

But if you send 53 emails to someone who has no use for what you’re selling (or asking for), you’re probably getting blocked well before the 53rd email.

So how do you know when to keep going, give someone space, or move on?

Let’s break down how to make that call...

Before you send another email, you have to answer a very simple question: could there be a real opportunity?

Following up with someone who genuinely has no use for your product is like trying to sell a lawn mower to someone in a fifth-floor apartment.

You can be extremely persuasive. But they still don’t have a lawn.

And there’s a difference between a prospect acknowledging a problem and you deciding they have one.

If they’ve explained their situation and your product can’t help, don’t waste your time.

Someone who has a need for your product but lacks buying authority might still be worth your time, though. They could introduce you to their boss or help make the case internally.

A prospect who forgot to reply and a prospect waiting for next quarter’s budget have different problems.

A reminder follow up will help the first person. But the second person needs something to change.

Asking about budget every day is like opening the oven every minute to see if dinner’s ready. You can check as often as you want, but it still needs time to cook.

So find out what they’re waiting for. A budget meeting? A new hire? Their current contract to expire? A campaign to launch?

Then time your follow up around that event.

And find ways to help move things along. Offer to prepare the business case before the budget meeting or help them work out what implementation would involve.

That gives you a concrete reason to reconnect.

And if they say, “Let’s talk after our planning meeting on the 15th,” put the 16th on your calendar. You have enough information to avoid sending “Any updates?” on the 9th.

Ryan Serhant tells a story about following up with a prospect who went silent for 5 years. 5 friggin years.

He kept sending new info like market news and comparable sales, with an occasional ask.

According to Serhant, that prospect eventually bought a $16 million property.

That’s a long time to stay in someone’s inbox. But useful information gives them a reason to keep you top of mind while their circumstances change.

Think of the friend who sends you an apartment listing because they remember you’re looking. You’re probably happy to hear from them.

Now imagine that friend texting “Have you moved yet?” every morning. It’s the same subject, but it gives you a very different feeling.

This applies to getting a sales job, too. Following up consistently with a hiring manager shows how much you want the role. It also gives them a preview of how you might go after a deal once you’re on the team.

And as a sales manager, you want passionate reps who keep pursuing an opportunity when the first email goes unanswered. Someone who follows up until they get a yes or no.

Harry followed up 53 times and got Benioff on his podcast.

Clearly a ton of follow up can pay off. That doesn’t mean the guy who might buy three $30 software licenses deserves the same treatment.

You’ve got other people to call.

And every hour you spend chasing someone who probably won’t buy is an hour you could spend finding someone who will.

Now, if landing this one customer would make your entire year? Sure, you should be ruthless about following up. Just make sure you have a reason to think it could happen beyond “Man, that commission would be nice.”

If they’re interested but busy, keep at it. If they need help getting their boss on board, help them. If they’ve told you to stop, you should probably stop.

And if they’re waiting on January’s budget, put a reminder in your calendar.

Today’s newsletter was written by Nic Conley