Discovery: asking the right questions

You cannot sell what you don't know they have

• Our clients tell us things every week. We capture too little of it, and we ask too few questions back.
• Most missed opportunities are not lost to competitors. They are simply never seen.
• Awareness comes before selling: the CSMs who know their accounts best create the most pipeline, because they connect client problems to our services before anyone asks for a quote.
• This series: 2 hours on how to ask (discovery), 2 hours on what to ask about (cyber crash course).

Four sessions, one skill

The 5 phases of every great meeting

• No fixed time per phase: business contact → more phase 2 · IT director → more phase 3 · active project → more phase 4.
• It is your job to manage the meeting flow, not the client's. Prepare every meeting, first or hundredth.

01Relationship building & intro

Genuine human connection first, then a one-line purpose for the meeting. Signs of a great relationship: they respond fast, their time is easy to get, they ask about you, you know their family and hobbies.

• Share about yourself even unprompted; over time it prompts them to ask back (reciprocity).
• Layup question: “So, how did you get into IT?” — it works, and it lets you tell your version too.
• Match their energy. Read the room; don't annoy them.
• Avoid the weather and traffic. It's boring and everyone does it.
• Note what you learn (kids' names, hobbies) and never forget it. That is also discovery.

Six types of questions — two that matter today

02Business discovery

Understand: their organization, priorities, role and team, employees, locations, competitors, recent acquisitions, budget context.

03Technical discovery — broad, then 3 deep

Goal: a high-level inventory of their environment. Awareness, not a deep dive. Two classic faults: sales people skip this phase (especially in follow-ups); technical people go too deep, too soon.

Questions to retire

Overused questions that scream “just another salesperson” — and only harvest what the client already knows:

• Not forbidden — just reactive: you only get the opportunities the client has already identified.
• Current-state discovery is what surfaces the opportunities nobody asked for.
• You need both. Creative beats reactive.

04Opportunity

• Part 1: handle the immediate topic — often the reason for the meeting.
• Part 2: raise the potential opportunities your discovery just uncovered. Qualify with who / what / when / why / how; explore challenges, build the pain.
• Your real goal is to disqualify. Every potential opportunity you disqualify sharpens the focus on the real ones — count it as a win.
• Triage: most compelling to the client? Biggest outcome? Or simply ask what is most pressing.

05Closing

• Never leave a meeting without the next meeting scheduled. On the spot — not “I'll send you a Doodle”.
• Tie your value statement to what they told you, in their words: “You mentioned nobody watches the alerts at night…”
• Typical close: propose a focused follow-up with the right expert — “Can I bring our specialist to walk you through how other organizations handle this?”
• Handle objections calmly. If there is no fit, say so — it builds trust.

Capture it — or it never happened

• Your awareness only counts if it is written down where the team can use it: CyberstackDB (stack, contacts, observations, opportunities).
• Ritual: 15 minutes right after the meeting — update the account, log the potential opportunities, schedule the action items.
• Grade yourself weekly on two things: did I have enough meetings, and did I gain awareness in each of them? Pipeline follows awareness.
• Goal over time: 100% awareness on your accounts. Every blank cell in our account map is a question you have not asked yet.

The method on one page

Live discovery, for real

The client (played by Bill): IT Director of an 800-employee Québec manufacturer. Recently promoted, small team, board suddenly asking questions about cyber after a competitor got hit by ransomware.

One volunteer runs the meeting (15 min), from hello to booked follow-up. Everyone else observes: