5 Questions That Double Your Win Rate

Look, I'm going to be straight with you.

Most sales reps freestyle their discovery calls. They wing it. They ask surface-level questions, get polite answers, and then wonder why their deal stalled at 60% probability for the next six months.

I've been there. Early in my career, I thought being "relationship-driven" meant avoiding the hard questions. I thought if I was nice enough, deals would close themselves.

Spoiler alert: They don't.

After scaling companies from zero to $100M+ valuations, leading enterprise sales teams, and working with some of the biggest fleets in the world, I've learned something critical:

The questions you ask in discovery determine whether you win or lose.

Not your demo. Not your pricing. Not your "relationship." Your questions.

Here are the 5 questions that changed everything for me - and will double your win rate if you actually use them.

Question 1: "What Happens If You Do Nothing?"

This is the most underrated question in B2B sales.

Most reps ask, "What are your pain points?" or "What keeps you up at night?" Those questions suck. They're vague. Everyone asks them. And they don't create urgency.

Instead, I ask:

"Walk me through what happens if you don't solve this problem in the next 6-12 months. What does that cost you - in dollars, time, or risk?"

Why this works:

Forces them to quantify the problem
Creates urgency (the cost of inaction)
Reveals whether this is a nice-to-have or a must-have

Real example:

Me: "What happens if you don't solve your inspection process in the next year?"

Fleet Director: "We'll probably get hit with another DOT audit. Last one cost us $80K in fines and we had to ground 15 trucks. And honestly, I'm worried someone's going to get hurt because we're missing critical defects."

That's a real problem. That's a deal that closes.

If they can't articulate the cost of doing nothing, you don't have a qualified opportunity.

Question 2: "Who Else Loses Sleep Over This?"

This question uncovers your real buying committee.

Most deals die because you sold to the wrong person. Or you sold to the right person but didn't involve everyone who had veto power.

I learned this the hard way at Whip Around. I'd get a fleet manager excited, run a killer demo, get verbal commitment... and then radio silence.

Why? Because the CFO, IT, and Safety Director weren't in the loop. And they all had concerns we never addressed.

Now I ask early:

"Who else in your organization loses sleep over this issue? Who has to approve this? Who's going to complain if we don't involve them?"

Then I say:

"Let's get them on the next call. I'd rather answer their concerns now than have this die in committee later."

This does two things:

Identifies all stakeholders upfront
Positions you as someone who respects their process

Multi-threading isn't optional. It's survival.

Question 3: "What Does Success Look Like in 90 Days?"

This question separates tire-kickers from buyers.

If they can't tell you what success looks like in a specific timeframe, they're not ready to buy. They're just shopping.

I ask:

"Let's say we implement this. It's 90 days from now. What does success look like? What metrics improved? What changed?"

Why 90 days?

Short enough to be real
Long enough to show results
Creates a tangible outcome you can sell to

Question 4: "What's Your Process for Making a Decision Like This?"

This is how you control the sales process instead of getting controlled by it.

Most reps ask, "When are you looking to make a decision?" That's weak. It lets them dictate the timeline with zero accountability.

Instead, I ask:

"Walk me through your process for making a decision like this. Who needs to sign off? What needs to happen? What's your timeline, and is that flexible or locked?"

Then I shut up and listen.

This tells me:

If there's a real timeline (or if they're just browsing)
Who the real decision-maker is
What obstacles are coming
Whether I'm in a competitive bake-off

And here's the key: I hold them accountable to their own timeline.

Question 5: "Why Are You Evaluating Solutions Right Now?"

This is the question that separates real opportunities from time-wasters.

If someone's looking at software, there's a reason. Something changed. Something broke. Someone got yelled at.

I need to know what that trigger was.

"What happened that made you start looking at solutions right now? Why not six months ago? Why not six months from now?"

The answer tells me everything:

"We just failed an audit" → High urgency, real pain
"My boss told me to look at options" → Low urgency, probably no budget
"We're growing fast and our old system can't handle it" → Perfect timing
"Just exploring what's out there" → Not a real opportunity

If there's no triggering event, there's no urgency. And if there's no urgency, you're going to chase this deal for nine months while they "evaluate options."

Don't chase deals that aren't real.

My Challenge to You

Pick your next 5 discovery calls.

Use these 5 questions. Word for word if you have to.

And track your results:

How many deals stayed qualified after discovery?
How many had real urgency?
How many progressed to the next stage?

I'm betting your win rate goes up. Way up.