Why Sales Sucks: What to Say
How to run the option and tip the odds in your favor
Note: This is part IV in my Why Sales Sucks series. If you’d like to read the whole thing from the beginning, just click here.
There is No One Pitch
When I started my sales career more than a decade ago, the job was a war of scripted attrition. You made the calls, read your lines, and took your lumps. Every few dozen rejections, someone would agree to a meeting. And eventually, some of those meetings would turn into new customers. You just had to give it time.
But looking back, my static, single-track, “one size fits all” sales script wasn’t only ineffective, it was exhausting. It felt bad. You could sense what the unlucky person was experiencing on the other side of your canned, stale pitch.
I am being sold to, they were thinking. And I do not like it.
That feeling —when you can tell the prospect isn’t so much listening as waiting for you to finish — sucks. Noticing your inability to connect with that person sucks.
Not knowing what to say next or how to fill that awkward, begrudging silence really sucks.
Thankfully, through trial and error, I figured it out. I learned to tailor my pitch to who I was speaking to and to what they cared about. I learned to build trust by showing empathy and proving that I understood what my prospects were actually working on, trying to fix, and suffering through.
A CRO friend of mine likes to say, “Prescription without diagnosis is malpractice.” Eventually, I ceased my malpractice. Eventually, I focused less on blindly prescribing my product and more on diagnosing where I could help.
And guess what? That change in mindset — from selling to diagnosing — worked. It made the job more fun, and it made me more money. It still works — no matter what you’re selling.
There is no one sales script. Every customer is different. Every conversation is too. Context matters. You can’t steamroll someone into buying from you — especially if what you’re selling is expensive, complex, or unfamiliar. You need to learn what this other person is struggling with and how they’re solving their problem today before you can show them a better way.
You need to diagnose before you prescribe.
You need to read, then react.
How to Run the Option in Sales
When I train B2B sales teams, I teach a kind of “option offense for sales”, made up of three techniques. These techniques work for nearly any stage of a sales process, but they’re especially useful when you’re meeting someone for the first time and feeling out if and how you can help.
A quick disclaimer: What follows is not a rote framework. This isn’t paint-by-numbers. As I said before, there’s no one sales pitch. I don’t have a magical unlock to share with you. (Anybody who claims they do is lying.) My goal is to share a few principles that seem to improve things for most sellers. Rather than suggest a new framework to adopt, I just want you to (i) be aware of the moments that matter most in conversations like these, and (ii) to give you some techniques to play with and make your own during those moments.
I encourage you to keep, consider, and try what seems useful, and then discard the rest. Your mileage may vary.
Technique 1— Create a Give-to-Get
The best salespeople are empathetic. They recognize that buying something for a business is extra work. Hell, it’s kind of a whole extra job. An extra job that (i) pays nothing and (ii) comes with uncertainty, stress, to-do’s, and questions that need answering. Good salespeople don’t forget this. I know how confusing and annoying this whole purchasing process can be, they say. I get what you’re going through, and I’m here to help.
This empathy needs to come through in the first 30 seconds of every sales conversation you have, especially if you’re talking to a prospect for the first time. It should take the form of an agreement: a sort of contract that creates a good trade for both sides. A give-to-get.
Here’s an example of what this can sound like on a cold-call. This is me talking to someone I’ve never spoken to before. Someone I dialed out of the blue.
“John, this is Paul from TechCo. I know you didn’t expect my call this morning — how does this sound: Give me 45 seconds to tell you who I am and why I phoned you, and you can decide whether it’s worth a 5-minute conversation or not. Fair?”
What did I just do? Assuming John says yes, I just created a contract.
What does John get? Time-boxed certainty about what he’s going to hear next, explicit permission to hit the eject button if the conversation isn’t clear or interesting enough, and a powerful signal of empathy and respect that comes from asking his permission.
What do I get? Assuming he says yes, I get a mutually agreed-upon window to make my pitch. I don’t have to kick John’s door down, because he invites me in.
This is the opening you’re looking to create. This is an equal give-to-get. This is a good trade.
I won’t get into all of the different ways you can create a contract during a sales call. There are too many to cover in one article. Just remember this: It pays to be a little paranoid. Great salespeople possess an always-on radar about how much mutual agreement is in the air around them. They’re mindful about continually seeking consent. They’re constantly thinking about the next few steps in a conversation, architecting where they want to nudge things, and creating a give-to-get by asking permission before they move forward.
By doing this, the salesperson leads the prospect, hand-over-hand, into a more trusting, exploratory dialogue — one where where they earn the right to share stories, challenge assumptions, and probe at the gaps their prospect is trying to address.
None of that happens without mutual agreement. It’s the unlock for everything that follows.
Technique 2 — The Sorting Question
In football, an option quarterback reads the defense before they make their decision to run or pass. The more the defense reveals, the more information the QB has to work with, and the greater their probability of making the correct read + gaining as many yards as possible. The option offense is built on a basic principle of sports strategy: You’re more likely to score points when you know what the other team is about to do.
Sales conversations are no different. You’re always guessing and sensing whether this person you’re talking to has a problem you can solve, how they’ve tried to solve it in the past, how open they are to listening to you, and whether they’ll actually commit resources to do something about it. The more data you can gather about them, the more you can get a sense of things before you try to convince them of anything, the more you can shape the conversation in a way that serves you both.
But here’s the challenge. No one is going to sit there (especially in a first meeting) and let you endlessly grill them. You need to earn the right to learn. And to do that, a delicate balancing act needs to be performed. You need to send a signal of credibility while you gather the minimum effective dose of information you need to make your pitch — all without being obnoxious.
One way to do this is to ask what I call a “sorting question.” Here’s an example of how it might sound on a call:
“Let me ask you just one question so I can tailor our conversation appropriately: Most banking customers we speak with are of one of two minds about automating their back-office — (A) some are already automating a few things with basic tools, and (B) some don’t have any automation in place at all (they’re thinking about it, but haven’t gotten around to it yet). Which of those buckets would you put yourself in?
What did I just do?
First, I sent a signal of credibility. I let them know that I’m familiar with their world and have a framework for how I think about it. There are basically two types of people out there, I say. There’s people out there who are doing something to solve their problem, and those that know they should — but just haven’t gotten around to it yet. I present the two types non-judgmentally. Neither type is better or worse, I’m implying. I see both in my work all the time.
Then, I asked for some information. “Which one of those types would you say is more like you?” In doing so, I just created a non-threatening space they can step into. A space to fill with the information I need about them.
Why do sorting questions work? They makes you seem like you understand their business. They buy you time. They force you to listen — always a good thing. But most importantly, they give you a clue of which track you want to direct the conversation down. It tells you what flavor of your pitch is likely to resonate.
They give you the read you need to react appropriately.
Part III — Hit Them Where it Hurts
Once someone admits that they’re more of a (A) or a (B), what then? This is where too many salespeople lose patience. They can’t help themselves. This is when they make it all about them. “Great, our proprietary cloud-based machine-learning model uses AI to increase your revenue by X% and decrease your costs by Y%.”
No no no no no. Stop it.
This is what you sound like.
“Here’s what we sell here’s how it works please buy some please please please?”
Chill. Take a breath.
I promise, you’ll get to talk about the super-cool product you’re selling in the minute. But not yet. Be patient. This is still about them.
This is the point where you react and dig in. Not on the details of your product. Not on how superior your technology is. This is where you dig in on what sucks about their job. Remember that quote from earlier:
“Prescription without diagnosis is malpractice.”
This is when we diagnose. This is when, like any good physician, we ask them to “point to where it hurts.”
Nobody wakes up thinking about buying software. They wake up thinking about how to have a good day at work. They wake up thinking about how to avoid or fix the thing that threatens that good day. They wake up thinking about how to avoid pain.
That's what you should ask them about next. Their pain.
When done well, asking about pain sounds like a bit of guessing game.
When done well, it sounds something like this — a sort of pain-finding mad lib:
“You’re in good company. When I talk to people in similar situations, the narrative usually goes something like this: Despite trying [1], most people in your role still can’t do [2], which leaves them exhausted with [3] and anxious about [4]. Any of that happening over there?”
Those placeholder letters deserve some explanation.
[1] is what they’ve already tried to solve the problem. Maybe they’re using spreadsheets, or throwing bodies at the problem, or using a competitor's inferior product, or using outside consultants. Very few people are doing nothing to solve their problem. And knowing what people are using when they aren't using you is an absolute must.
[2] is the promised land. It's the seemingly-reasonable result that's still just out-of-reach. (This is also where you subtly throw shade at the prospect's current state and your competitors without being too overt, arrogant, or threatening.)
[3] and [4] are your emotional pain statements. They’re the negative, nagging, personal feelings that accompany the gap between this person’s current state and the promised land. These are the emotions that arise from knowing that they’re falling short. More on that in a second.
How Everybody Jacks This Up
This pitch likely sounds different than what you’re used to. That’s no coincidence. Most sales calls don’t sound anything like this. Most sellers jack this up.
Here’s how:
They have no idea what the competitive alternatives are. They haven’t gotten curious enough to know what people typically do before they buy their product. They haven’t started from a place of buyer empathy.
They don’t articulate “what you’re still stuck doing” in the buyer’s words. A good example of a [2] is something that should be simple to get to but it’s in people’s way. Here it's helpful to look for work that's slow, still being done by hand, or both. Another ingredient derived from pure buyer empathy.
They use stale business problems instead of actual pain-points for [3] and [4]. Pain is not about cost savings, or operational efficiencies, or technical debt, or revenue gains. Pain is when you go home, pour yourself a drink, flop down on your couch, and complain to your spouse or roommate or dog about the injustice visited upon you that day. Pain is personal. Pain is how you feel. You should talk about it as such. You talk about pain by using emotive words like Concerned, Anxious, Uncertain, Stressed, and Exhausted.* Remember: If you’re not talking about emotions, you’re not talking about pain.
They don’t tailor the pain statement to the persona they’re talking to. When I talk about personas with our portfolio companies, I'll often talk about the concept of "the balcony and the dance." Executives are watching things from the balcony. Individual contributors are out on the dancefloor. While both are at the same party, they are seeing things from entirely different vantage points. The approach you use to talk to them should reflect this reality.
Final Thoughts
There is no one sales pitch. Every sales conversation is different because every person you talk to is different. They all have unique ways of working, challenges they’re trying to overcome, and workarounds they’ve constructed to deal with those challenges. While your prospects might all have similar titles, everyone is coming from a different place.
Remember this: Closing a deal requires connecting with a person. That means acknowledging that you must earn the right to learn about what they’re going through. It means honoring their uniqueness. It means diagnosing before you prescribe. It means reading before you react.
So what should you say on your next sales call?
The answer, of course, is “it depends.”
And now you know on what.
Coming Soon - Part IV: Making It Your Own
*I steal from the ClozeLoop guys when I teach our portfolio companies how to talk about pain. Their C.A.U.S.E. framework is a great one and will give you all the pain vocabulary you’ll ever need.