Hey Niepodam,

A few weeks ago, I took an early Uber to a client workshop.

Barely awake. Coffee in hand.

I get in, and this guy driving, middle-aged, soft-spoken, starts chatting.

But not in a “so… how’s your day?” kind of way.

It was subtle.

“Busy day ahead?”
“What kind of work do you do?”
“Oh yeah? What’s that actually look like day-to-day?”

Fifteen minutes later… I’d basically given him my resume, career arc, and outlook on B2B sales in 2025.

When I stepped out, I realized: That guy just ran a better discovery than half the reps I’ve coached.

Why? Because he did 3 things most reps don’t:

1. He eased in sideways

No “what’s keeping you up at night” nonsense.
Just: “Busy day ahead?”

Low-friction. Natural. Disarming.

Cold calls and early discovery should feel the same.
Start small. Get permission to go deeper.

2. He made it about me, not the script

He followed my answers, not a checklist.

If I said “heading to a workshop,” he’d say:

“Nice. You leading it or attending?”

Most reps are too busy planning their next question to listen.

3. He laddered the questions

Surface → Context → Impact.

I said “sales.” He said “Ah, tough gig. What kind of sales?”

I said “consulting.” He said “So companies bring you in when reps aren’t hitting?”

Boom, we’re in the pain.

That’s the ladder. Don’t jump it. Climb it.

Try this structure on your next call:

Start soft: “What made you take this call today?”

Follow the thread: “Sounds like X is a priority—why now?”

Dig one layer deeper: “If that doesn’t get fixed this quarter, what happens?”

Don’t force it.
Don’t fake it.

Just… be curious.

Like you’re an Uber driver with a long ride and nothing to sell.

Takeaway:

Most reps rush discovery. But the best ones ease in, follow curiosity, and ladder their way to truth.

That Uber ride wasn’t a conversation.

It was a masterclass.

You just have to listen.

Alan "Modern Seller" Ruchtein.

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