Mission ImPossible: 4 Steps to Finding the Truth in Your Pipeline


Mission ImPossible: 4 Steps to Finding the Truth in Your Pipeline

Let me know if this scenario sounds familiar…

You’ve got a sales team (of some sort). You’re invested in marketing. You’ve got some sales leader or a group of them who are responsible for “driving revenue.”

And you’ve got goals for growing your company this quarter, and next, and next… to infinity and beyond.

But it’s not happening like you know it should.

You’re missing the number.

60% of those deals listed at 60% likelihood to close aren’t closing. Maybe 30%. Which makes you wonder if they understand percentages.

Yet you don’t come from a sales background. Maybe product, or marketing, or engineering, or ops. Or even finance.

So what do you do if you want to know what’s real and what’s fairy tale?

I’m going to make this as simple as possible for you. Give me a few hundred words to see if we can do that.

And guess what? Industry doesn’t matter. If it’s a B2B sale, and involves more than 1 meeting, this fits.

Most pipeline reviews are an expensive waste of time. We get a bunch of six figure earners in a room to tell stories for a while. The result is a forecast that came from a magic 8 ball.

“Doesn’t look likely,” is all you should hear.

Here’s when you know you’re hearing stories in a review. It sounds something like…

  • ________ is on vacation, but plans to get back to us the Monday she returns.
  • _________ is taking this to the CFO for approval.
  • __________ really likes us, but needs a discount to get this done.
  • We need to negotiate price to get ___________________.
  • I feel good about _______________.
  • It seems like _________________.
  • I think _____________________.

Just discount your likelihood of close by 30% for everyone one of those you hear. And yes, I know your pipeline will be negative when that’s done. It’s ok. At least we’re dealing in reality.

Your team may as be saying to you, “You see, what had happened was, uh, you know…”

Let’s look at how you, dear Executive, can get the truth.


There are scorecards and predictive tools we can give you. But you’re not ready for them if management isn’t, well, managing deals and the people selling them.

So let’s start with how YOU can run your pipeline meetings.

This is going to be so simple you’re going to think it won’t work. Still, give it a go. For four weeks.

Note: I’ve modified the below after a conversation with friend and erstwhile mentor, Jeff Johnson.

Here’s what you need to pull out of pipeline meetings, for every opportunity.

Find what’s at stake for the prospect. You should ask the rep, “What’s the buying motivation from someone who counts? Not your contact who can’t write a check.” Another way to ask this is,

  • Why do they want this?
  • What’s the most compelling reason they gave you that they want something?
  • What happens to them if they don’t get this in place?
  • What impact does this problem have on their ownership or hitting annual goals?


(Let’s inspect that pipeline.)

Every answer for every prospect should be unique. Otherwise, why have salespeople? They should also be specific and compelling.

Quick question to ask yourself and the rep: “Would you put $5,000 of your own money on them solving this problem? And with us?” There’s a litmus test.

Too often, you’re getting something like, “They’re interested in our user interface,” or some other nonsense.

It’s a waste of time.

What’s the highest level you’re engaged with?

Should be self-explanatory, but let me clarify.

A lot of reps are trying to get lots of deals in the pipeline. They do this by talking to people THEY are COMFORTABLE talking to.

These usually aren’t people who sign checks.

One of the lessons I learned long ago is that it’s easier to sell someone up high, but more challenging to get your head in the game to talk to them.

It’s simpler to envision talking to manager, but really hard to get them to carry the ball.

When looking at opportunities, ask, “Who is the highest person we are ACTIVELY talking to?”

Follow up with, “What have they SAID their biggest pain is? And what have they SAID is the impact if the problem isn’t solved?”

If you’re dealing with managers, your close rate won’t go above 20%. If it’s with directors, it won’t go above 45%. If you’re dealing with VPs, you probably have a cap at 55-60%.

The C-level? Well, what do you think?












(Are you close to anyone who can write a big check?)

Where’d you get that close date?

Let’s be honest – most close dates are what the rep wants to be true, and largely driven by your EOQ date. Most have nothing to do with the buyer’s timeline or goals.

So simply ask, “Why’d you put that date?” “Did the prospect agree to that date?” “Does the prospect know that you are committing to this date?”

As I often say, if the prospect didn’t say it, it doesn’t exist.

What’s the Next Step?

Ask this, and you’ll usually hear,

  • I need to ________
  • I’ll follow up __________
  • I am supposed to send ______________

What you WANT to hear is:

  • They agree to do X and I have agreed to do Y

But sadly, most people are chasing Amy. There’s no reciprocity. The rep is working really hard for the prospect without the prospect doing something for the rep.

Want even more truth? Ask the rep,

  • What’s the plan to get to someone who can write a check?
  • Is your contact going to help with that?

Get these answered and you’ll know where you stand.

These questions are so basic, you’d think they wouldn’t need to be answered.

However, many people, when selling, are afraid to ask the really hard questions. They either believe these questions are offensive and will kill deals, or they don’t believe it’s right/ok/appropriate to ask such questions.

My friend and partner in our Exec Sales Program, Chris Schaum, is GREAT at this sort of question. He literally asks things like, “What does this put in your pocket?” Or “What’s the path to a contract?”

Because he wants to know.

And so should you. So ask your people. Eventually they’ll begin asking your potential customers.






Adam Boyd