How’s My Driving

When it’s better someone else talks to your customers.

You’ve seen the sticker on the backs of cars and trucks of all size a thousand times driving down the highway.

To state the obvious: when you call the number on the bumper sticker, it’s not the driver of the truck that picks up, it’s some disinterested person behind a desk.

Whether this person spends all day answering these calls or just part of their day, it doesn’t matter. They jot down your report on how their brand is presenting in the real world – good, bad, indifferent. They’re appreciative and maybe they apologize. Either way, it’s far more constructive for both parties than if the driver was directly involved.

Maybe the driver does receive the report. More likely it gets aggregated into a pool of all the other reports, patterns, and trend lines. Maybe this report shows things are getting better, maybe it shows something still isn’t working.

Last year, I was on the receiving end of 65 similar conversations on behalf of my clients. From PE-backed companies generating $50M a year to emerging education providers hoping to break $2M. No matter the size or industry, all of them know the strategic value of having a disinterested third party conduct frank, ground-truth, conversations with their customers about price, value, and success.


2 years ago, a CEO of a $50M company proudly told me he’d talked with customers extensively…when he bought the company 5 years prior. He had. Since then, the market has shifted pretty hard (that’s why we were talking). We skimmed through a few recent deals. Sure, the customers he talked to were still customers, just no longer the majority segment, or the growing segment. The mental image of his customers was outdated.

He was replaced as CEO 18 months later.


Founders and CEOs should absolutely talk to customers and regularly. A call from the CEO is a fantastic way to show a customer they’re highly valued. But, no matter how disciplined, executives are regularly are hampered by two things in their customer conversations:

  1. A customer mentions something that isn’t quite working, and the CEO responds. Not defensively. Just helpfully. “Oh, we’re working on that”. Suddenly, the interview becomes a support call and then support call becomes a sales pitch with promises made – however inadvertently. The customer leaves reassured. However, the CEO learned nothing new and ever so subtly put the spotlight back on themselves and took it off their customer.
  2. The second is quieter. Your customers agreed to this conversation because they want you to succeed (we talked about this in For Starters #61) and their goodwill is exactly what makes the conversation delicate. They’re not being evasive — they don’t want to offend or cause drama. The persistent frustration they cursed under their breath last week comes out as “it’s mostly fine, a few rough spots.”

These aren’t failures of effort. They’re the physics of the relationship – and one reason why the truck driver isn’t answering the “How’s My Driving” call (the other is safety).


Every round I’ve facilitated has turned up at least one outcome customers are actively buying that my client has never named, never packaged, never valued, and never priced.

“I was the first person in 25 years to pass an audit with zero findings.” – A customer that saved his employer a pile of money, frustration, and paperwork.

The customer considered eliminating the audit stress the entire reason for buying the software. My client’s pricing hadn’t factored it in. Their customer would have paid specifically for it – especially now.

Without regular customer conversations like these, you’ll never get these success stories, and never learn all the unpriced value you’re providing your customers.


“Prices have gone up 25-30% in the past two years, but it’s not a problem — we’re getting substantial value.” – An actual customer, in an actual interview about my clients’ product.

My client had no idea. They gave me a list of clients, expecting every one of them to be significantly challenging (why they hired me to have them) and some of them were. But not all. Not even most. Not even the customer arriving with 34 complaints. A solid chunk of them, like the customer above, were price-insensitive and my client was leaving money on the table.

“I don’t even know how many pricing tiers they have. Are we on the top one? Second to top one? Is there one that fits us better?” – Another real customer quote, they’re not price-sensitive, they just want confidence they’re getting the best deal.

These aren’t things customers say to you. 

They’re things customers say to someone who isn’t you.


“I have no problem aside from the cost. It’s very expensive for what we’re using it for, and I know we’re underutilizing it.” – A customer that’ll probably churn shortly anyway.

In every round of these conversations we find a segment of customers you should probably just stop serving – or at least no longer target. They’ve quietly shopping for an alternative and haven’t yet told you. 

At the end of a round, we know how to differentiate them from the price-insensitive ones.


“I now see my untapped growth opportunity – not by adding new – but by focusing on what’s working.” – an energized client after walking through the customer interview findings.

Talk to your customers – absolutely.

But know, there are things they won’t say to you, things you won’t think to ask, and sometimes having a neutral third party answer the phone identifies the competitive advantage we didn’t know was there.


Enter my “How’s My Driving?” offering. Four weeks. Ten customer conversations. One specific, testable, pricing move.

If you’re running a B2B SaaS or professional services company and want to find out which customers are open to paying more – let’s talk.

Give me a call to get started