Why Sales Sucks: How To Make It Your Own

How to move beyond the basics and avoid sounding like everybody else

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.

The Arrival Fallacy

In Happier: Learn the Secrets to Daily Joy and Lasting Fulfillment, author and psychologist Tal Ben-Shahar introduced the world to a concept called the Arrival Fallacy. The Arrival Fallacy states that after achieving a goal, the satisfaction we expect often doesn’t arrive. You finish your climb, reach the summit, but the thrill you expected just isn’t there. This is an especially cruel kind of letdown. After all, isn’t this what you planned on celebrating? What you worked and sacrificed for? And now, instead of fulfilling us, our seemingly big achievement just leaves us wondering: “...Is that it?”

Dr. Ben-Shahar puts it more succinctly than I do:

“Arriving rarely makes us as happy as we anticipate.”

I’m bringing up The Arrival Fallacy for a reason. If you work at it long enough, pretty much everyone eventually figures out the basics of sales. With a little practice, you reach a point where you’re calling the right people, saying the right things, and closing deals more predictably. You’re not learning to sell anymore. You’re doing it.

And in a small way, you’ve made it. This is what you wanted when you first picked up the phone and clumsily tried to convince some stranger to listen to your pitch. It’s what you dreamed of when you rode along with a more seasoned teammate and watched them connect with, persuade, and close an otherwise-skeptical prospect.

“How did they do that?” you wondered. 

Well, now you know.

And knowing, at first, feels pretty good. But then the Arrival Fallacy hits. And the comfort that came with your newfound commercial proficiency quickly starts to fade. Pretty soon, the job feels... dull. The spark that powered you through those early stumbles starts to dim, and the work becomes kind of a grind. 

It’s a bummer when this happens.

But it’s also an important moment of truth.

The Moment Of Truth

You now have a choice to make. You can accept that the skill you were once so excited to learn has become a vocation. You can surrender to the grind, stop developing, and start to mail it in. You can accept that you sound a little bit like everybody else. You can start going through the motions. You can let yourself go.

But in a world full of flat, mechanical, jargon-laden sales pitches; a world in which buying something for your business has become, on average, pretty damn terrible, I am here to implore you: Do not allow yourself to plod lazily into the jaws of that trap.

This is when you have to decide: Whether you’re going to settle for simply knowing how to sell, or whether you’re going to strive for mastery.

This is when it’s time to make the job your own.

So to give you the tools you need to save yourself from all the reasons why sales sucks, here’s my best advice for keeping your beginner’s mind alive and healthy - and a few suggestions for how to start doing the job in a way that’s fresh, unique, freeing, and genuinely yours.

What follows isn’t a step-by-step framework. It’s more of a menu; a list of three next-level sales techniques that anyone who masters the basics should think about incorporating. My advice: Don’t try to develop them all at once. Grab onto the technique that resonates most with you. The one you’re drawn to. The one you’re most excited to translate into your handwriting.

And then, whatever you do, don’t let go.

Technique 1: A Clear Point-Of-View

Most high-ticket B2B purchases (especially in my world of software) sit within nebulously-defined categories that are constantly-changing, riddled with technical jargon, and are generally difficult to navigate. But this is good news if you’re a seller willing to take a stance. If you can combine clean language and strong opinions to paint a complete picture of (a) the problem people are wrestling with, (b) what options they have, (c) the puts and takes of those options, and (d) what typically triggers people to get serious about finding a solve, you’ll not only come across as credible - you’ll be gifting the person you’re selling the exact thing that’s missing in most buying experiences out there: Clarity.

This is the four-point framework I use to coach sellers as they start to craft their own authentic POV:

1. Challenges – How the Problem Shows Up

Challenges are more than operational snags; they’re personal. When people spend hours on manual tasks that could be automated or feel constantly pulled in different directions, their work becomes a grind. A strong POV doesn’t just describe the problem that people have - it acknowledges the frustration and wear it creates. Show you understand both the operational inefficiencies and the morale impact, and have language you lean on describe both. That’s a level of empathy that can set you apart in a world full of feature-preachers.

2. Triggers - What Causes People To Look Around

As my friend

Rob Snyder

(good Substack/better guy) likes to say:

“Life is a series of pain-points I mostly do nothing about.”

Read that sentence again. It’s an important idea to get comfortable with as you create your authentic POV. Here’s why: It’s not enough to understand problems and pain. You also have to understand the tipping point that finally moves people to do something about it. So as you’re thinking about your unique take on your space, don’t stop at reflecting on how your customers describes their problems and the impact of those problems. You also have to unearth what happened right before they agreed to talk to you about what you sell - right before they willfully entered into a conversation with a potential vendor. What was the breaking point? What was the catalyst? Why did they agree to this phone call at all? Get at that and you are way ahead of all of the other surface-level sellers out there.

You’ve heard people talk about urgency in a sales process? Understanding triggers is how you start to manufacture urgency. When you can describe and ask questions about triggers, you unlock a whole new level of credibility - and an important lever you can use to convince people that the best time to act might be right now.

3. Options – How People Deal with the Problem

“This is how we see the market.” Those six words make people stop what they’re doing and listen. Nothing conveys expertise like someone who can cut through the noise and simplify a complex category. Whether it’s bucketing solutions or charting them on a spectrum, what you’re going for here is helping your buyer see their options more clearly. People like buckets, and when you can map a crowded product category in a way that makes sense, you score major points with frustrated buyers looking for guidance.

4. Gaps – Shortcomings of Those Solutions

Despite all the tools and strategies in play, most buyers (especially the ones willing to talk to you!) are still dealing with nagging gaps in the way they do their work. It’s rarely because they’re doing something “wrong” - it’s more common that the solution or method they’re using today doesn’t fully deliver. A clear POV surfaces these gaps without forcing them, naming and giving labels to the frustrating limitations that lead to people looking around.

A good framework to start with: “Despite having a handle on [general task], most companies still end up stuck doing [specific, painful process] themselves.” This kind of insight gives them language for the daily realities their current solution leaves unsolved - and invites them to openly vent about what sucks about the way they’re doing things today.

Once you lay it out like that, it’s a LOT easier to get people to accept your view of what options are out there, how people can decide between them, where your product fits, and who it's best for. From there, selling becomes pretty easy: It’s simply about getting them to agree to your framework and then proving you can deliver what they need. That’s it.

Technique 2: Next-Level Curiosity

If there’s one quality that separates the best salespeople from everybody else, it’s curiosity. Nailing this technique is all about weapons-grade listening. It’s about getting beyond the surface-level stuff and digging into what’s really happening in the buyer’s world, so you can honestly say these exact words:

“OK, I get it. And I think we can help.”

The artform here is question selection - more specifically, finding the moments to ask next-level, wake-up call type questions. These kinds of questions don’t just give you information or check the boxes on your sales methodology. They get the buyer to confront what it really means if they stay stuck in the status quo.

So what kind of questions qualify as next-level curious? Here are some of my favorites: 

• “How does this challenge show up in day-to-day operations for your team?”

• “How long has this been an issue, and who else does it impact?”

• “What have you already tried to fix this? And how has that worked so far?”

• “Where does this stack up against everything else on your to-do list?”

• “If you could wave a magic wand and have this solved, what would change first?”

• “Which KPI or metric would see the biggest impact if things started improving?”

• “Have you earmarked a budget for this, or would you need to convince others on the value of a solution here to start to get them onboard?”

I want you to notice a few things about the questions on this list.

• They’re open-ended: You’re going for storytelling, census-taking here. Yes, we need to know about what they’re currently on, how many seats they need, and the integrations that matter most. We’ll get to that. For right now, we want stories - about what’s going on, how it impacts them, and how important fixing it is. (A tiny but important pointer: Sometimes the most effective discovery question is simply “Say more about that.”)

• They’re promote vulnerability: They invite the buyer to explore both the problem and its impact in their own words. And once they verbalize what sucks about their situation, they’re far more likely to at least consider the prospect of another solution - your solution.

• They lead you towards “I think we can help”: I’m hitting this point again because it’s so important. The best questions set up a natural opening to bridge the buyer’s problem with your solution. With every answer, you’re gathering the pieces you need to recognize when and how to introduce your product as the obvious answer - but only after you’ve accumulated the evidence you need to naturally offer your assistance. 

Technique 3: Signature Moves

Danny Meyer, famed restaurateur and author of Setting the Table, is known for championing “enlightened hospitality”—a brand of service so intentional that it feels unforgettably tailored. For Meyer, hospitality is an art, a commitment to delivering more than expected. In sales, we can harness that same idea of enlightened hospitality to create moments that stick. Sales may not be about serving meals, but it’s absolutely about leaving your buyer with the feeling that this process—their time, their interest, and the experience itself—matters.

The best sellers create these moments by injecting personality and presence into the sales process. It’s not about rigid scripts; it’s about guiding the conversation using touchpoints that feel energizing and fresh. The way you make that happen is through what I call your “signature moves.”

These aren’t quirks; they’re the well-timed maneuvers that make your sales process memorable. They’re the parts that leave buyers thinking, I want to work with this person. Whether it’s the way you break the ice, the story you tell to demonstrate a feature, or how you transition between points, these are the moments when you’re not just a representative but a trusted guide, someone leading with insight, attentiveness, focus - and even a little flair.

Signature moves don’t happen by accident. They’re practiced, polished, and specific. Here’s a few parts of the sales process to consider developing your own signature moments for:

• Opening a Call: Set the tone by making the buyer feel seen and valued right from the start. Sure, do the small talk thing. But then, pick your moment to say something unexpected but meaningful. “I’ve done some homework on your team’s recent projects, and I can see a few ways we might add value. Before I dive in, I’d love to hear your take on where this fits in.”

• Sharing Stories: Sometimes, the easiest way to sell someone is to tell them a story about a happy customer who is a little further down the path - then ask how they’re different. “I have to say, your situation sounds an awful like [Customer X]. They were dealing with some similar issues, ran a thoughtful process, and ultimately decided to work with us. Can I tell you a little more about them and you can clue me in on what’s different about your situation?”

• Guiding with Confidence: Buyers may hold the budget, but they often don’t have a roadmap for the process. And that’s where you come in. Use your expertise to guide them with confidence: “I’ve worked with a lot of teams facing similar challenges, and there are usually three areas that are critical to explore at this stage. Here’s my take on where we should go next. Let me know if there’s something else you’d like to add.”

• Closing with Impact: In later stages of a deal, close the conversation by making them feel they’re in capable hands. Skip the “soft” close and opt for something intentional. “I think we’ve covered what matters most to your team. Here’s what I recommend as our next steps. I’ll take point on getting things started, but if there’s anything else you want to address, now’s the time to make it part of the plan.”

Each of these moves creates an experience. When buyers feel they’re in the hands of someone who knows their world, who can confidently outline the process and lead the way, and who picks a couple of moments to make it distinctive, immersive, and fun, you start to earn their buy-in, attention, trust, and respect - the intangible qualities that make the difference between winning and losing those critical 50/50 deals.

Plus, nailing a signature move feels damn good. It’s a dopamine hit that shifts the experience for you too, from just another pitch to something you look forward to sharing. That energy is contagious—and when the buyer picks up on it, they’ll not only feel more engaged - they’ll feel more confident in what you say and what you’re selling.

Final Thoughts

Sales is a craft. And like any craft, it’s something you first learn the fundamentals of, then refine over time, and ultimately put your own unique spin on. This isn’t about settling for the basics; it’s about practicing the act of creating something undeniably yours, something that keeps you interested long after the initial thrill of learning it fades.

The real satisfaction in sales comes not just from hitting your numbers, but from knowing that every deal you close has a little bit of you in it: your work, your choices, and, yes, your personality too. So take one of these techniques, sand off the edges, put it to work, and let it remind you why you started doing the job in the first place.

Because if you’re doing it right, it’s never just “the job”—it’s your job.