Good Morning. Good morning. Today is National Plan for a Vacation Day, which sounds great until you remember that your quota doesn't take a vacation with you. We like to celebrate this day by opening the calendar, staring at it for five minutes, then closing it again because there's never a good time to be out when we’ve got deals to close. At least we can all bond over the shared fantasy of being unreachable for a week. Now, let's get into today's Follow Up. (:

  • How to deal with prospects wanting a pilot 🤝

  • Not every complaint deserves your attention 🧭

  • 10 gifts that reps are sending prospects 🎁

  • Sales jobs & a meme 😂

Sales Tip of The Day 💡

When a buyer asks for a pilot, define success before agreeing.

“Sure, let’s run a pilot.”
“We’d be happy to. But before we do that, what needs to happen during the pilot for this to earn a full rollout?”

Pilots without success criteria turn into free trials with no owner.

Figure out what turns the pilot into a deal before it starts.

Make sure every rep follows the playbook that actually hits quota.

You’re on a live call.

A tough question comes up. A competitor is mentioned. An objection you didn’t expect.

Sales OS is an in-call AI assistant that guides reps during live conversations. It helps them stay aligned with the approved playbook, handle objections correctly, and know what to say next without breaking the flow of the call.

Instead of thinking “I should’ve said that” after the call ends, Sales OS supports reps in the moment while the deal is still alive.

If playbook adherence and in-call execution matter to your team, Sales OS was built for you.

The Customer Is Always Right (Until They Aren’t)

Let's talk about the customer you secretly wish would just... go away.

You know the one. Every email from them makes your stomach drop. Every "quick question" turns into a 3-hour ordeal. Every issue somehow becomes YOUR emergency.

And yet, you keep bending over backwards because someone once told you "the customer is always right."

As your sales bestie, I’m here to tell you… They lied to you.

While you're busy firefighting for one nightmare account, you're probably bleeding opportunities with ten good ones.

Your quota doesn't care that Karen needs 47 emails to understand basic features and your commission check doesn't reflect the emotional labor of being someone's punching bag.

If you’ve ever felt this pain, here’s what to do about it:

How to Diagnose The Type of Complainer

Before deciding whether to keep accommodating the customer or step back, you need to understand the root of the frustration.

Most complaints come from one of two places.

1) An ‘engaged’ customer

These customers complain because they are heavy users of your product or service.

Your product matters to their job or well being, so the friction they are experiencing is real to them.

You'll notice a pattern with these accounts.

The complaints cluster around the same features, and they want to help you make your product better because they are heavily invested in the outcome..

2) The customer is misaligned

These customers complain because your product was never intended to serve them.

The product doesn't match what they actually need, so they're constantly trying to force it into a shape it was never designed to be.

I’m going to tell you how to spot one of these customers, but first, we need to talk about when the customer is actually ‘right’.

When Difficult Customers Are Your Best Ones

Some of your loudest customers are also your most committed ones.

They care enough to push. They notice friction because they rely on the product, and they are trying to get more value (not just vent).

Your most valuable customers are often loyal and vocal.

We see this with Apple customers every day…

When Apple Maps launched in 2012 it had major issues and customers complained loudly because they depended on it daily. Apple took the criticism seriously and rebuilt the product.

It wasn't a fit problem for them. It was an execution problem.

Signs a customer’s complaints are worth prioritizing:

  • They fit your ideal customer profile (ICP)

  • They use the product as intended

  • Feedback is specific and actionable

  • Issues connect to business outcomes

  • Fixes would benefit other customers

These customers usually have genuine feedback and can become your strongest advocates.

When Complaints Mean It’s Just Not A Fit

Now let’s talk about the other side.

Some customers complain for a good reason, but that reason has nothing to do with execution.

The product simply was not built for them.

Imagine you sell a CRM designed specifically for pool builders. It’s built around how they run jobs. Tracking installs. Managing permits. Coordinating crews around weather and timelines.

Then a pest control company signs up.

They struggle with reporting because a pool construction job is totally different from a pest control job. So they ask for features that pest control companies need, but don’t align with your core customers’ needs.

Their frustration is real.

But that doesn’t mean you should reshape your product to fit them.

You’ll know it’s a fit problem when:

  • They sit outside your ICP

  • Core features go unused

  • Requests only apply to their business

  • Every solution requires custom work

  • The account consumes more time than it is worth

Trying to accommodate these customers creates more damage than trust.

The right move is honesty.

Be clear about who the product is built for. Set boundaries around what will and won't change. Help them find a better fit if one exists.

That protects your product, your future customers, and your sanity.

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