Andrew Penny, June 23 2026

What sets Off Your 'Squirrel-Alarm'?

I stopped into a local bagel shop recently for a coffee and breakfast bagel after my morning swim. I’d been there a few months earlier and hadn’t had a great experience, but I gave them the benefit of the doubt. Everyone has an off day. Surely they’d have sorted things out by now.

Nope - The place felt a bit dirty and untidy. The counter staff weren’t exactly rude, but they weren’t welcoming either. No greeting. No thank you. No direction on where to find the coffee fixings — the little things that make the transaction feel easy.

The coffee was decent. The bagel was good. The price was reasonable. So transactionally, it worked.  Experientially, I’m not going back.

Which brings me to squirrels. Yes, squirrels.

If you’ve ever tried to feed one, you know the routine. You crouch down, hold out a peanut, and wait. The squirrel sees the peanut. It wants the peanut. But it doesn’t run straight toward it.

It freezes.  It looks around. Sniffs the air. Takes two tiny steps. Stops again. Checks for danger. Takes another step. Maybe it grabs the peanut. Maybe it bolts.

The squirrel is interested in the prize, but it is far more focused on not making a fatal mistake. 

Your buyers are the same. They may like what you offer. They may need what you sell. They may even have budget. But they are still looking for reasons not to buy.

Retailers and restaurants often use Secret Shoppers to evaluate the customer experience. Smart ones want to know what actually happens when a real person walks in, places an order, asks a question, gets confused, waits, pays, leaves, and decides whether to come back. 

B2B companies can do the same. A B2B 'secret shopper' looks at the entire buyer journey: outreach emails, website, social media, inbound response time, sales calls, proposals, contracts, onboarding, invoicing, delivery, support, and follow-up.

Most companies are pretty good transactionally.  The product works. The service is delivered. The invoice gets sent. But the experience often creates friction. Slow replies. Confusing messaging. Generic proposals. Awkward handoffs. A website that doesn’t answer obvious questions. A sales process that makes the buyer work too hard.

Each one sets off a little squirrel alarm. And once enough alarms go off, the buyer runs.

The opportunity here is huge. You don’t always need a better product, a lower price, or a bigger sales team. Sometimes you just need to remove the small moments of doubt to help the customer take the next step in the journey.

Even a small improvement in conversion rates, or repeat purchases, can have a big impact on revenue — and will lower your cost of sale at the same time.

So, the next time you walk into a shop, restaurant, hotel, or showroom, think like a secret shopper. What made you feel welcome? What made you hesitate? What felt easy? What felt off?

Then ask yourself the more uncomfortable question: If a secret shopper went through your sales process, what would set off their squirrel alarms?

Would they buy? Would they come back? Or would they grab the peanut and run?


See you next time,

Andrew


PS – We have been inside hundreds of B2B companies. We know how they sell and we know how they buy. We know how buyer journeys are supposed to work and what can go wrong.

Written by

Andrew Penny

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