Discovery Is a Leadership Discipline

Customers can admire your technology and still decide it’s too risky to buy. The questions you ask decide which way that goes.

Most lost enterprise deals end with a familiar postmortem. The customer loved the demo and called the platform technically superior, and then they bought someone else.

A customer can admire your technology and still decide it’s too risky to buy. What moves them from admiration to commitment is rarely something you showed them. It’s the questions you asked. That’s why I treat discovery as leadership work, and why it sits at the center of the Trusted Advisor discipline in The Presales BOAT System™.

Most discovery sounds like an interview

Ask how many agents a customer has, or which CRM they run, and you’ll get a fact every other vendor in the evaluation has already collected. The customer answers easily because nothing about the answer is new to them.

Better discovery sounds closer to executive consulting than to gathering requirements. “What happens to revenue when customer wait times increase?” uncovers the business underneath the numbers. “Where does the work slow down between departments?” gets you the problem instead of a diagram. Questions like those tell you what the customer is trying to change, and a credible recommendation has to be built on that.

Five levels, and most discovery stops at two

In my book I describe discovery as five levels. Facts come first, then problems, then business impact, then the organizational dynamics around the decision, and finally the executive’s vision of what the business looks like a year after deployment.

Most discovery stops at the second level because it feels like enough. You understand the pain, and pain is what your product addresses. The conversation only turns strategic at the third level, where you learn what the problem costs and which executive already has it on a slide. It’s also the first level where the customer learns something from answering.

The order matters. Each level earns the right to ask the next one, and nobody gets to open a first meeting at the fourth.

One question none of the other vendors asked

A regional utility brought in a third vendor to evaluate a new contact center platform. The SC opened with the same facts everyone else had collected, then asked something none of the others had. “What is the biggest unspoken risk?”

A project three years earlier had failed publicly enough that two directors left the company over it. He kept going. He asked what happened to revenue when wait times rose during storm season, and who inside the company would lose influence if this project stalled again. His last question was what, a full year after deployment, would make the executive team call this one of the best decisions they’d made. After that, the sponsor stopped describing software and started describing the future she wanted, with shorter outages, fewer complaint escalations and a call center that could flex during emergencies.

When the utility signed, the sponsor explained the decision in her own words. “We just believed you’d get us through it without it becoming another mess. That’s what we were buying.”

The question most SCs never ask

The highest-value question in discovery is some version of who loses influence if this goes forward. Most Solution Consultants never ask it. The idea has usually occurred to them, but the question costs something. Asked badly, it sounds like a vendor shopping for a wedge between departments, and the rest of the evaluation gets managed at arm’s length.

Two things make it safe. Sequence is one. You earn the question by being useful on the easier ones first, so by the time you ask it, the sponsor has already seen that you’re working on their outcome. Framing is the other. Ask about the project instead of the people. “What would have to go wrong for this to stall the way the last one did?” gets you the same information, and it costs the person nothing to answer.

What you do with the answer

Getting the answer is the part people practice. The harder discipline is what you do in the minute after.

When a sponsor tells you about a failed project that pushed two directors out of the company, she has handed you the real evaluation criteria and a piece of her company’s institutional embarrassment at the same time. The tempting move is to use it in the executive readout so everyone can see you understood the stakes. That turns you into the person who repeats in a large meeting what someone told you in a small one.

The utility SC never mentioned the failed project again. It showed up in his plan instead, in how carefully the rollout was phased and how the risk of a repeat was handled, and the sponsor noticed.

What a customer tells you in confidence belongs in your plan, not in your deck. Handle it that way and each question you ask gets a better answer than the one before it. Over the course of an evaluation, that’s how an SC the customer admires becomes one they trust with the decision.

The Five Levels of Discovery, with a question bank for every level, is in Chapter 19.

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