Discovery Done Right

A checklist for the most important, most atrophied technique in B2B sales

The Gift And The Curse of Inbound

In the early 2000s, a couple of MIT graduate students noticed that the world of digital advertising was changing. Busy executives were getting sick of being interrupted online. All the banner ads and pop-ups were getting old.

This gave them an idea. What if, instead of using “look at me” tactics like display ads and paid search, companies designed their digital footprint to automatically deliver customized content to consumers based on their online behavior? What if, when someone filled out a form to see a whitepaper or asked for a demo of a product, you could customize their experience, sending them down different pathways based on who they were and what they interacted with? What if you got customers to come to you by making the experience of learning about your company feel customized and helpful? What if you could make digital marketing educational instead of just another kind of billboard?

What if you could do all this, automate it… and get the prospects to come to you?

That kind of “inbound marketing” would be pretty effective, the graduate students thought.

So they started a technology company to make it happen.

A company you might have heard of: Hubspot.

Over the next few decades, rising demand for software and the proliferation of inbound marketing (and the automation platforms like Hubspot that powered it) changed the way that products got sold. Marketing departments became more powerful, and marketing-sourced pipeline became a more important, more-measured, more-budgeted-for part of growth. The two founders of Hubspot, Dharmesh Shah and Brian Halligan, even captured their approach to this new era of marketing in a book, titled “Inbound Marketing”, published in 2009.

Fifteen years after that book was published, we're in an interesting period in the world of technology sales. A world irreversibly - and not completely positively - shaped by the power of inbound. The zero interest rate phenomenon is over. And plenty of investors have violently downshifted from a grow-at-all-costs strategy to one that emphasizes profitable, sustainable growth. Their companies can’t just spend millions of dollars to generate inbound leads anymore. Their cash runways won’t support it, and neither will their boards. As a result, many of these companies feel like they’re living hand-to-mouth - wrestling with the question of how to feed their growth ambitions with far fewer leads coming through the door.

Fewer leads means each one is more precious. When you have fewer leads, every mistake hurts more. When you have fewer leads, every bad habit is more costly.

Here’s the point I’m trying to make with this history lesson. When money is cheap, demand is plentiful, and you have more than you need, bad habits always creep in. Your technique gets sloppy because your environment doesn’t demand good technique. Your technique gets sloppy because the consequences are less harsh.

This is true in life, and it’s true in sales. Fumble a lead or piss off a prospect? That was okay in a zero-interest-rate world. Another qualified lead would probably show up tomorrow. There were always plenty to go around.

But today, with lower marketing budgets and fewer leads to work with, the cost of those bad selling habits are far more visible. And it’s those bad selling habits that are very likely holding you and your team back from where you want to go, and how fast you want to grow.

The worst of these habits? Shitty discovery technique.

What does a shitty discovery call sound like? It’s a one-way conversation. It’s a painful, selfish, census-taking exercise that undervalues a hand-raising prospect, creates a poor first impression, and leaves people longing for what they really want from a salesperson: Perspective on the market, and help navigating their choices.

This affliction creates needless waste in the go-to-market machine. It’s literally costing companies millions of dollars in lost opportunities. That sucks.

But here’s what really sucks. Shitty discovery technique is ruining the technology buying experience for everybody. It’s levying a punitive, unnecessary tax on learning about what’s new out there. And it’s causing a lot of otherwise curious potential buyers to think twice before they agree to book time with your sales team.

How does that make you feel? Hopefully, like you want to fix the problem.

So let’s do that, shall we? Let’s lay out what discovery done right looks like.

A Checklist For Great Discovery

This is my checklist for a great discovery call.

#1 - Earn The Right To Get Curious

Most sales reps are taught that discovery is all about getting the intel you need to qualify a deal or pass inspection from your sales manager. But it ain’t so. A great discovery call should, first and foremost, be helpful to the customer. It should help them understand what's working for them and what isn't. It should help them reflect on what their problem really is, how and how much it’s hurting them, and how urgent solving it should feel. And it should help them sort through what their options are, even if some of those options don’t involve working with you. You earn the right to get curious about the stuff you need as a salesperson - those semi-intrusive details about their budget, what they’re currently using, their decision-making process, and who else you’re going to need to rope in - by supplying what they need first.

Earning the right to get curious is about staying balanced. It’s about making deposits before asking for withdrawals. Each probing question from you must be offset by a valuable, relevant insight you provide. This could mean cataloging common industry challenges, sharing frameworks that broaden their thinking, or highlighting relevant case studies from people like them that showcase how to get around what they’re facing. This balanced approach not only makes the conversation more engaging - it also generates evidence that you deserve to be thought of as more than just another vendor.

Basically, you earn the right to get curious by proving that you can be helpful. So do that. First and foremost, be helpful. And remember - help is defined in the mind of the recipient.

But here’s a seemingly obvious suggestion that many salespeople also miss: Once you’ve been helpful, once you’ve earned the right to get curious, go ahead and be curious! Ask lots and lots of really good questions. The best way to force yourself to be curious? Try this. Literally start your questions with the words, “I’m curious.” Like this:

• I’m curious, who else does that impact?

• I’m curious, what have you tried to deal with that?

• I’m curious, where does this fall on your list of priorities?

• I’m curious, what other kinds of fixes are you considering?

• I’m curious, how much time does that take you every week?

• I’m curious, who besides you is thinking about this problem?

Starting questions with “I’m curious” backs you into a corner of inquiry. It forces you to peel the onion and learn more about what’s going on in the world of the customer - not only so you can understand them better, but also so you can get them to identify, quantify, and prioritize their pain - which is what qualification frameworks out there (like MEDDIC and others) are built upon.

#2 - Help Them Understand Their Current State

Here’s a sneaky way to add value: Give customers the context that helps them understand how they should feel. That sounds a little woo-woo, but it’s quite easy in practice. It can be as simple as bucketing the struggles that other teams like theirs are having, describing “what’s hard” about residing in each of those buckets, and laying out a good first step to advancing out of their flavor of the struggle. The goal here is to hand the other person a mirror—a reflective insight that isn’t as much about showcasing what you sell, but rather about illuminating the truth of their situation and giving them new language to describe it. (Plus, the research would tell you these reflective insights are one of the things prospects actually want from a sales pitch.)

#3 - Share Some Earned Secrets - Be Thought-Provoking

Once you’ve helped them identify the “what,” it’s time to share some of the “how.” This step involves sharing the earned secrets that only experience can provide. These are not just tips or tricks. This is about gifting them with a step-by-step guidebook for how to get from here to there. You want to show them the promised land, and then lay out the turn-by-turn directions for how they can successfully make the trip themselves. Ideally, you also provide proof of how you’ve helped others like them make the journey that you’re enticing them with. More on what this can sound like in this recent article of mine.

#4 - Honestly Diagnose Whether You Can Help

As the saying goes, “Prescription without diagnosis is malpractice.” So make no mistake. Your first job as a salesperson isn’t to sell. It’s to diagnose.

To properly diagnose whether what you sell is a fit or not, you need to know a few things. Things like where the sticking points are for the customer. Things like how they articulate the pain-point that brought them your way in the first place. Things like what they’ve tried to make it better, how that’s going, and how big of a deal all of this really is for them. Just as you wouldn’t trust a doctor who blindly suggests a major surgery, you shouldn’t go into any first sales call assuming you’re the answer to their problem- no matter how excited or eager the person on the other end of the line might seem.

So practice being as curious as you are commercial. Try to approach the conversation with the integrity of a physician diagnosing an injury rather than a salesperson pushing a product. Understand their pain points deeply and summarize for them what you’re hearing that makes you think you might be a good option, as well as what you’re hearing that gives you pause. If what you offer clearly isn't the right solution, be honest about it. In a world where most buyers end up making no decision at all, this diagnostic mindset builds trust and credibility, even if it doesn't convert every conversation into a sale.

#5 - Create a Contract About What Happens Next

After identifying the customer's needs and establishing how you can help, it's time to agree on the next steps. This 'contract' isn't legally binding, but it does represent a commitment between both parties. Outline what you will do next, what you expect from them, and set clear timelines. This ensures both parties are aligned and understand their responsibilities, making the transition to the next stages smoother and more predictable. The biggest piece of coaching I give sellers here? Be prescriptive. Don’t be afraid to lay out (yes, on a slide) your take on how serious prospects successfully evaluate their options. Lay out the steps, ask what works for them, and then agree to the next move you’ll make together. Buyers have anxiety about how to do their homework correctly. Give them a path to follow, and you’ll be pleasantly surprised how willing they are to come along.

#6 - Get A Sense For How You Would Get Them Started

Buying and implementing a new service or piece of software means making something stick. And making anything stick is hard work. So ease their entry into what you’re selling. Discuss the onboarding process, what initial steps you would take together to get them up to speed, and share some broad strokes of how you’ll tailor the early stages of working with you to fit their specific needs. Highlight support structures and resources you offer to help them get the most out of the partnership. This step is about reducing anxiety and building confidence in your ability to deliver. Everyone who buys software asks themselves the same question: “How hard is this actually going to be?” Answer that question before they ask it, and you’ll have scored some serious points.

#7 - Be Polite - Take Notes, Synthesize, and Send a Recap

Always end the call with a visible demonstration of professionalism and courtesy. Taking detailed notes during the conversation and sending a follow-up recap isn’t just good fundamentals - it sends a signal about your attentiveness and commitment to their needs. The recap should summarize key points discussed, reaffirm next steps, and include any additional resources or information promised during the call. This not only reinforces the relationship you’re hoping to build, but also gives you a thread to pull on the next time you talk.

I'm amazed at how many sellers out there don't send notes after important calls, don't play back the pain points they discover early on in sales processes, and don't bring back the insights and the unique nature of each buyer as they get closer and closer to the closing part of the process. The bar here is very low - and AI is making it easier than ever to pick out the stuff that matters and put it back in front of the buyer. Still, many people don’t do this. It’s the easiest way to stand out in a competitive process. Don’t not do it.

Yes, people want to buy the product that's best for them. But they also care a lot about who they buy from. And given the choice, amidst all the feature-function talk and requirements-building exercises, there’s a good chance that what they really want is to do business with the person who's more attentive, more polite, and who has their shit together marginally more than the other folks that they're considering.

Be that person. Do that work.