Selling is Hard. Buying is Harder

As legal tech founders and vendors, we often grumble about how tough it is to sell to lawyers—whether in-house or in firms. Newcomers are always stunned by how conservative the industry is.

And let’s be honest, we vent. A lot. We complain about long sales cycles, lawyers’ aversion to technology, and their reluctance to change. We resort to discounts, last-minute deals, relentless email follow-ups, and other acts of desperation to close deals.

But what are we missing? Why is selling to enterprises so hard?

We’re looking at the buyer’s journey from the seller’s perspective.

The Buyer's Decision Paralysis

Picture this: You're planning a trip to Spain 🇪🇸 for the first time. You dive into research mode—travel blogs, Instagram hashtags, friend recommendations, TripAdvisor reviews. Hotel or Airbnb? City center or beach? Boutique or chain? Five-star luxury or authentic local experience?

Three days later, you've created a comparison spreadsheet worthy of a PhD dissertation, complete with color-coding and weighted scoring. Then life gets busy, you put the project on pause, and when you return, prices have changed. You’re back to square one. You're exhausted before even booking a flight.

Now, imagine your firm has made the "strategic decision" to improve process X (let's say, budget management). You or your team are tasked with finding software solutions. Unlike choosing a hotel, your firm has never purchased automated budgeting software before. There's no institutional memory to rely on.

You dutifully create requirement lists, research options, build comparison matrices, watch demos, poll colleagues, send RFPs, and wade through hundreds of pages of vendor fluff—all while your actual job continues to demand attention.

Then you interview users only to discover that despite the challenges with the current process, they're "fine" using Excel.

Really?

The Status Quo: The Easiest Decision They'll Never Make

The vendor parade continues. Demos are conducted. Proposals pile up. You've nearly narrowed down your options when suddenly key stakeholders become "super busy" and stop engaging. The process stalls.

Then come the predictable interruptions: vacation season, budget planning, year-end closing. "Let's revisit this next quarter when things calm down" becomes the refrain (narrator: things never calm down).

Here's the uncomfortable truth: Most professionals aren't experienced buyers because they might purchase the same type of product only once or twice in their career. Procurement is a distraction from their primary responsibilities. Alignment is elusive. Some are enthusiastic; others are indifferent or resistant.

In this environment, the path of least resistance—doing nothing—often feels like the safest choice. No one wants to champion a failed initiative. No one wants their name attached to a technological misstep.

The best decision? Wait and maintain the status quo... for now.

Break Through the Inertia, Make it Easier to Buy 

Buying enterprise technology is exhausting and risky, especially when it involves changing established workflows. Even positive change creates resistance. Current tools might be imperfect, but they're familiar and—technically—functional.

We've all heard the wisdom: "The buyer will buy when they're ready." While you can't (and shouldn't) force a purchase, your sole mission is to make buying easier for your customer.

Here are tactics that have proven effective but are often overlooked:

✅ Clear Differentiation From The Alternatives

When all products look identical to buyers, they're forced to create their own mental differentiation—and that rarely favors you. You're essentially delegating your positioning to someone who has never bought your product before.

Effective positioning isn't just marketing fluff; it's clarity for customers and internal alignment for your team. Sales, marketing, success, and support should speak the same language. At my previous company, we revisited our positioning every 6-12 months as our product and market evolved.

Clear and differentiated messaging ➡️ makes it easier to buy

✅ Effective Customer Discovery (That's Actually... Discovery)

Everyone claims to do great discovery calls, yet somehow, they don't translate to sales. Why? Because many reps use "discovery" as a thinly veiled closing opportunity. And those who do listen are listening to respond, not to learn.

A genuine discovery call is your golden opportunity to understand the buyer's pain points—or better yet, for them to articulate those pains aloud. After dozens of conversations, these challenges start sounding repetitive, but resist the urge to say, "I've heard this before." Instead, respond with genuine curiosity: "Really? That sounds challenging. Tell me more about how that affects your work."

The insights gathered here should shape how you conduct demos, communicate with users, and build a process that addresses what they actually need—not what you think they want.

Understanding customer needs ➡️ makes it easier to buy

✅ The Champion Letter (Your Secret Weapon)

This is the missed opportunity that keeps me up at night. A champion letter is a well-crafted recap of the buyer's pain points and needs, confirming your product's potential alignment and outlining clear next steps. You do this after each milestone in your buyer’s journey. 

There's a specific technique for this (well explained in Customer Centric Selling, one of my favorite sales books). Without a champion letter, it's as if the conversation never happened. Make every interaction count! Those who've worked with me know my obsession with getting this right.

Alignment and accountability with the customer ➡️ makes it easier to buy

✅ Not Every Buyer Should Be Your Customer (Yet)

Your product is constantly evolving, especially in the early stages. Overselling capabilities might win short-term deals but creates long-term problems. If a prospect wants budgeting software with all the bells and whistles, but you only have a basic version with more features planned for later, be honest about your current capabilities.

Focus on matching their most pressing needs with your existing solution. If possible, identify your unique advantage—your "wedge"—that solves their problems better than alternatives. If there's no fit, don't waste their time or yours (easier said than done, I know).

Focusing on the target customer ➡️ makes it easier to buy

✅ Out of Sight, Out of Mind (The Nurturing Non-Negotiable)

Making it easier to buy means educating prospects on how to evaluate and purchase your solution. Partner with marketing to create content addressing their needs and explaining both problems and solutions.

Provide materials that help them present your product internally, especially when you lack direct access to other decision-makers. Control your messaging by supplying detailed information about what you do and how you solve problems.

Set a nurturing cadence based on where prospects are in their journey. The moment you stop nurturing is when competitors swoop in—and there's nothing worse than learning your prospect was ready to buy, just not from you.

Educating and nurturing the customer ➡️ makes it easier to buy

The next time you feel frustrated about legal professionals being "resistant to change," remember: They're not professional buyers, and purchasing enterprise software is a high-risk, low-reward activity for many of them.

Our job isn't to complain about their buying habits but to make the purchase process so clear, so valuable, and so well-supported that saying "yes" becomes easier than maintaining the status quo.

Being patient ➡️ makes it easier to buy

What tactics have you found effective in making it easier for legal professionals to buy? I'd love to hear about your experiences.

Do you have an idea, or are you working on something awesome and want to chat? 

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