Very early in my business, after I had left the security blanket of corporate life, I had what I believed was a life-changing (at the time) deal for long-term training with a client that had multiple locations…

"In the bag."

The biggest number I had ever asked for.

(I had to double-check the agreement before I sent it because I still had a hard time believing I was actually going to get paid that much.)

And like a lot of salespeople do…

I started mentally spending the profit before the ink was dry.

I remember thinking about the check the way people do when they dream about how they would spend their lottery winnings when buying a ticket.

Visualizing cooking steaks on that new, expensive grill for the deck.

Paying off the credit card and no longer worrying about the mounting interest charges.

Finally getting a bit of a cushion in the business bank account.

In my mind?

This was a done deal. Rock solid.

I had asked all the questions…

Built the value…

Even mapped out dates and locations for the training…

And my primary contact was completely on board.

But then… after the agreement was sent and I didn't get anything back after the agreed-upon time…

The dreaded unease crept in.

My decision maker didn't return a couple of calls, after being totally responsive before. 

(This was before email. I know… hard to imagine, right?)

I finally got him on the phone late on a Friday afternoon.

He sounded apologetic.

(That's never a good sign.)

He told me the project was dead.

Not delayed.

Not waiting for one last sign-off.

Dead.

And the reason blindsided me.

It wasn't him.

It wasn't a competitor.

It was someone inside the organization I didn't even know existed.

An auditor in the Finance department who advised cutting "discretionary" expenses.

WTH?

Training your salespeople… the producers who actually bring in the revenue… is a discretionary expense?

Well… to this person, (whose income was provided by those he was depriving training) it was.

A stakeholder who had never been in our conversations.

Someone with veto power who stepped in late and shut the whole thing down with the stroke of a pen.

But here's the part that really stung…

I thought I had already covered that base.

I had asked about decision makers.

Or at least…

I thought I had.

And that's when I learned one of the most expensive lessons of my young career:

Asking who else is involved…

Is not the same as uncovering all the landmines that could kill your deal.

Because deals don’t just fall apart over the things you know about.

They also fall apart over the things you never realized were in play.

And that…

Is today's Big Lesson.

So here's what that little financial faceplant taught me:

A deal is never "in the bag" just because someone says yes.

I know. You know that too.

But we still do it.

We hear the verbal agreement and something in our brain goes, "Alright… this one's done."

We relax a little. We mentally move it into the "closed" column.

Some of us even start mentally spending the commission.

Apparently I was an overachiever in that department.

Hidden stakeholders. Budget shifts. Procurement getting involved. Executive vetoes. Internal politics. Stakeholders who suddenly appear late in the game like surprise guests at a party you didn't plan.

And none of that shows up unless you go looking for it.

You've been there. I know you have.

Most of us ask, "Who else is involved in this decision?"

And we get an answer. But that answer is almost always incomplete.

Not because your contact is lying. They may not know who's going to weigh in.

They may underestimate someone's influence. They may assume approval is routine.

Or, and this is the one that gets me, they may not want to admit the decision isn't fully theirs.

So you move forward thinking you're clear.

And then the deal gets torpedoed by someone you never knew existed. Like an auditor in Finance who thinks sales training is "discretionary."

Ask me how I know.

Which is why you have to go beyond just asking who's involved and start pressure-testing the deal itself.

The Landmine Question

There is one question I started using after that deal blew up that has saved me more grief than I can count. Here it is.

Simple. But very few people ask it. And it works for a few reasons.

First, it assumes forward movement. You are not asking if. You are planning when.

Second, it frames obstacles as external. You are not challenging their authority or questioning their commitment. You are asking them to help you look around corners.

And third, it forces them to think about things they have not mentioned yet.

Bosses. Budget approvals. Legal reviews. Internal resistance. The stuff that never shows up in standard discovery.

Their answer usually gives you one of two things.

-Clarity on what could derail the deal.

-Or confirmation that the path is actually clear.

Either way, you are operating from reality instead of hope.

And hope is not a forecasting strategy. I learned that one personally.

You do not need 20 questions. Just a few that pressure-test the deal from different angles. Here are the ones I keep coming back to.

The Veto Check "Is there anyone who could say 'no' to this, even if everyone else says 'yes'?" This surfaces silent power players fast. CFOs. Compliance. Executive committees. The person with the red pen who nobody mentioned in your first three calls.

The Process Map "Walk me through what happens internally after we agree to move forward." You will often uncover steps and people you never knew existed. Procurement. Legal. IT security reviews. Three-signature approval chains that somehow didn't come up until week six.

The History Check "The last time you made a decision like this, what surprised you about the process?" Past landmines love repeat performances. If it delayed them last time, it will probably delay you this time.

The Change Factor "Between now and implementation, what could change internally that might affect this priority?" Budgets shift. Leaders change. Initiatives get reshuffled. Good deals get caught in the crossfire. All manageable if you see them coming.

The Missing Person "Is there anyone who should be part of these conversations who isn't yet?" This one alone has saved me more deals than I can count. End users. Department heads. Influencers without titles. Sometimes the deal killer is not the buyer. It is the person who has to live with the decision afterward.

By the way, If you like questions like these, I’ve got an entire vault of them we use in training, including discovery, resistance handling, and decision-process mapping questions. Check out the Smart Calling College, and the Smart Calling Coaching and Training App for B2B Professionals.

Most deals do not die because you didn't do the sales things you’re supposed to do.

They die because you didn't see everything else in play.

Buying committees are bigger than they used to be.

Budgets are scrutinized harder.

Risk tolerance is lower.

People are worried more than ever about covering their butt.

And more deals die from unseen variables than from overt objections.

Nobody calls you to say they went another direction because of a procurement delay.

They just stop returning your calls.

You know this. You've lived it.

That deal you were sure about that just... vanished.

The one where you couldn't even get a straight answer about what happened.

Yeah. That one probably had a landmine you never found.

Look at the deal in your pipeline you feel best about right now. The one you are quietly confident about.

(Maybe you have already picked out the grill you are buying with the commission.)

Call your contact. Do not "check in." Do not ask for an update. Ask this instead.

"To prepare for the unforeseen, is there anything that could hold this up?"

Then be quiet. Let them think. Let them answer fully.

Because what they say next might save you from counting revenue you were never actually going to see.

Force the unforeseen out into the light now, while you still have time to handle it. Not after, when you are staring at a forecast that just went up in smoke.

Before you forecast that next "sure thing." Before you mentally spend the commission. Before you buy the grill…

Ask the landmine question. Get the risks out in the open. Give yourself the chance to pre-empt surprises instead of reacting to them after you got blindsided.

You cannot eliminate every risk in a deal. But you can spot the landmines before you step on them.

And that is the difference between forecasting and guessing.

Between being surprised and being prepared.

Men’s Health once printed a list of phrases everyone should stop saying.

One jumped out at me because I hear it in sales all the time:

“I meant to…”

As in:
“I meant to send you that information.”
“I meant to get back to you.”
“I meant to follow up.”

The translation?

“I thought about you… and then did something else.”

Not exactly the message you want to send a prospect.

Professionals don’t mean to.

They do.

If you say you’ll send something, send it.
If you say you’ll call, call.

Reliability is not a personality trait. It’s a behavior.

And prospects decide whether to trust you based on the little things, not the big promises.

Reliability and follow-through are actually a couple of the identity traits we dive deep on inside the Ultimate Sales Professional course. Because prospects judge professionalism long before they judge your solution

Here’s a quick language upgrade that instantly improves how prospects hear you.

Minimize “I” statements.

“I want to tell you about…”
“I think you should…”
“I’d like to show you…”

They don’t care what you want.

They care what it means for them.

Shift the focus:

“You’ll find…”
“You’ll notice…”
“What this does for you is…”
“You’ll see…”
“What you get is…”

Same message. Completely different impact.

One is about you.
The other is about their world.

And prospects always listen harder when they hear themselves in the conversation.

I always shake my head when I see those generic “best times to call” charts.

Usually from some content creator who was told to put out some stuff today.

“Engineers — 9:00 a.m.”
“Executives — 4:30 p.m.”

Based on what? Astrology?

The best time to call someone is when you can actually reach them. And that can’t be generalized.

So build your own data.

Create a field in your CRM or notes labeled Best Time to Reach.

Every time you connect with someone, log the day and time.

If they call you, log that too.

Patterns show up fast.

And when you start calling people when they naturally answer…

You waste less time dialing, and spend more time selling.

One more thing: the actual best time to call: always.

That's it for this week.

If that intro story hit a nerve, good. It was supposed to. I wrote it because I don't want you standing in the same spot I was, staring at a forecast with a hole in it, wondering what happened.

Pick one deal this week. Ask the landmine question. See what comes back. Then let me know what you found. I'm serious. Hit reply and tell me. I read every one.

And if you're sitting there thinking "I know someone who needs to hear this"... you probably do. Forward this to them. They can subscribe at SmartCallingReport.com. They'll thank you for it. Probably not as much as I will, but still.

One more thing. Some of you have told me your teams are using these issues as weekly training. If you're doing that, I'd love to hear how it's going.

And if you haven't tried it yet, this week's issue is a good one to start with. Hand it to your team and ask them: "What deal are you most confident about right now... and have you asked the landmine question?"

That alone could be worth an hour of training.

Go make it your best week ever!