Good Morning. Good morning. It’s officially Thanksgiving week, which means starting tomorrow, your inbox will be flooded with OOO replies from prospects who were already checked out last Thursday. And if you happen to be traveling for the holiday… well, I wish you luck. A record 81.8 million people are expected to travel between now and Dec. 1st. Translation: the only thing moving slower than your pipeline this week will be airport security lines. Now, let’s get into today’s Follow Up.
Triggers > dates ❓
Selling to people without pain 😨
Closing $1M with AI SDRs. 🤑
Sales jobs & a meme 😂
Sales Tip of The Day 💡
When a buyer says, “We’ll circle back on this later,” get a commitment around the trigger instead of the date.
❌ “Sounds good. When should I follow up?”
✅ “Makes sense. What would need to happen internally for this to become a priority?”
This helps you uncover what actually creates urgency and if there’s anything you can do to speed things up.
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How to Sell to People Who Don't Feel the Pain (Yet)
Here's the thing about sales... Most people only buy what they need when they finally realize they need it.
They wait until the pain hits. The regret kicks in. The fear of missing out becomes unbearable.
Obviously, we don't want our buyers to suffer. We want them to get solutions that prevent pain well in advance.
So how do you sell to someone who doesn't feel any pain yet? Someone you know will be hurting later, but can't see what's coming.
They're comfortable. And comfort is one of your biggest competitors.
Why Pain Is the Only Currency That Matters
Here's the thing about human psychology that a lot of salespeople miss.
People don't take aspirin before they get a headache. They don't buy umbrellas when it's sunny. They don't fix problems that aren't causing them obvious pain right now.
This can drive logical people insane.
You can see exactly what's going to happen to these prospects. You know they'll be in serious trouble in six months. But they can't see it, so they won't act.
Without pain, there's no urgency. Without urgency, there's no decision.
So you're trying to create motion in perfectly still water.
Why They Don't Feel the Pain (And What That Means for You)
I've identified four types of prospects who don't feel pain they should definitely be feeling.
The Boiled Frog: They've been in pain so long they don't even realize it anymore. "This is just how we've always done things." They don’t even know that there’s a different way of doing things.
The Revenue Drunk. Money keeps flowing in, so they don't care that they're hemorrhaging cash on inefficient processes. Why optimize when it seems like it’s working?
The Crisis Addict. They're so busy putting out fires that they can't focus on preventing them. Your product is so far down their list that they can’t even find the time to think about it.
The One-Vendor Prisoner. They've only ever worked with one supplier or system. They have no frame of reference for what "better" looks like, and making a switch doesn’t feel like an option.
Each type requires a completely different approach if you’re going to sell them.
How to Wake People Up Without Being a Jerk
Talk cold, hard numbers. Get specific about exactly how much they're losing every month. These losses might not show up on invoices, so break down time, money, energy, and efficiency costs in detail.
Project their future like a movie. Don't just tell them what could go wrong. Paint a vivid, specific picture of their world in 12 months if nothing changes. Make them feel what that failure will be like and use real examples from other companies that dealt with the problem they’ll face.
Show them what they're missing. FOMO is incredibly real. Nothing creates urgency like realizing you're losing. Let them know what their competitors are already doing and how it's benefiting those competitors. "Every month you wait is another month you fall behind."
Let them convince themselves. Ask them to predict their own future. "If we're having this same conversation next year and nothing has changed, what will that mean for your business?" Then shut up and let them connect the dots.
The goal isn't to create fake pain. The goal is to help them see the real pain that's already heading their way.
Because comfortable people don't buy anything, but people who can see disaster approaching will pay almost anything to avoid it.
What's the hardest part about selling to prospects who don't know they have pain?
