Handbook

Part II · Understanding the problem · Chapter 3

Discovery: the first meetings

Who to talk to, what to ask in which order, and how to leave with facts instead of a pitch.

14 min read

Customers know their symptoms well and their problems less well. Discovery turns a vague request into a problem everyone can agree on. Done well, the solution often looks obvious by the end. Done badly, you build an impressive answer to the wrong question.

What you'll take away

  1. 01How to prepare so the first meeting is spent on things only the customer can tell you.
  2. 02The four roles to identify, and how to find the gatekeeper nobody invited.
  3. 03People, process and systems: three lenses that stop you missing a whole category of facts.
  4. 04An order of questions, from Rackham's research, that gets you to cost and value.
  5. 05How to plan a short call around three outcomes, and what to send afterwards.

Before the first meeting

Spend an hour on homework so the customer's time goes on what only they know. Read what they publish: annual reports, job ads, product pages, recent news. Find out what they already bought from your company and how it is being used. Learn the names and roles of the people attending.

Then write down three things: what you think the problem is, the assumption you are least sure of, and six questions that do not give away a solution. You will probably be wrong about the first. Writing it down lets you notice when.

Find the cast, including who wasn't invited

In almost every engagement four roles matter. One person can hold more than one of them, and the job titles will not tell you who is who.

RoleWhat they holdWhat you need from them
SponsorBudget, deadline, the business caseTheir measure of success, in their words; access to the champion
ChampionDay-to-day ownership of the problemThe real workflow, the numbers, introductions to users
GatekeeperA veto: security, legal, IT, complianceTheir rules and fears, early, before you design
End userThe work itself, and its exceptionsWhat actually happens, step by step, including workarounds

Senior people describe the problem as it appears on their dashboards. That is useful context, but not the facts you design from. Treat what executives tell you as the frame. Get the detail from the champion and the users.

Gatekeepers are the people most often left out of the first meeting, and the most expensive to meet late. Find them by asking directly: "Who else will be affected by this? Who approves new vendors or data access? Has security seen anything like this before?" Then meet them to understand their rules, not to defend your design. A security lead who helped shape the guardrails will approve them. One who first sees them in a review will question everything.

Look through three lenses

The classic way to miss something is to understand the software perfectly and the organisation not at all. An old lens from IT consulting helps: look at the people, the process and the technology, and treat a gap in any of the three as unfinished discovery.

PEOPLEWho does this every day?Who owns the budget?Whose job changes if it works?Who is nervous about it?Who knows the unwritten rules?PROCESSWhat starts the work?Which decisions are made?Where does it change hands?What are the workarounds?What needs human judgement?SYSTEMSWhat is the real stack?Where does the data live?What is off limits?What breaks at peak?How accurate must it be?
Fig 1. Questions worth having answers to under each heading. A blank column at the end of discovery is a risk you are carrying into the build.

The process lens is the one engineers most often skip. Walk the work from trigger to outcome: what starts it, what decisions are made along the way, where it changes hands, and where people work around the official system. The handoffs and workarounds are where delays and errors live, and where automation either helps or makes things worse.

Climb the question ladder

Neil Rackham studied thousands of sales calls in the 1970s and 80s and published the results as SPIN Selling. His finding was that successful calls used four kinds of question, roughly in order: situation, problem, implication and need-payoff. Sales is not discovery, but the order transfers well, because people answer harder questions once they can see you understand the easy ones.

SituationHow it works today: volumes, systems, peoplegives you the baselineProblemWhere it is slow, wrong, risky or annoyinggives you the targetImplicationWhat that costs, and who else it affectsgives you the business caseNeed-payoffWhat a fix would be worth to themgives you their wordsdeeper
Fig 2. Rackham's four question types, in the order they tend to work. Each gives you something different to take away.
  1. 1

    Situation: how things work today

    Rackham found that too many of these bore people. Ask only what you couldn't find out beforehand.
  2. 2

    Problem: where it hurts

    Ask about concrete recent cases. 'Tell me about the last renewal that went wrong' gets you further than 'what are your challenges?'
  3. 3

    Implication: what the pain costs

    Follow a problem outward: who else does it affect, what does it cost, what happens if it gets worse? Engineers tend to skip this, and it is where budgets come from.
  4. 4

    Payoff: what fixing it would be worth

    Ask what a fix would make possible. When the customer describes the benefit in their own words, you can quote it back in your proposal, and it carries more weight than anything you could write.

A benefit the customer describes is worth more than one you claim.

Techniques that get you facts

Funnel from open to specific

Begin with a question that invites a story, then let each answer pick the next, narrower question. At a builders' merchant: "How does a trade customer usually order?" leads to "which orders cause the most phone calls?", then "the ones with substitutions?", then "what happens when the substitute is wrong?". Broad questions surface what you didn't know to ask. Narrow ones get you counts.

Mirror the words that carry feeling

Chris Voss, a former FBI negotiator, popularised a simple technique: repeat the last few important words someone said, as a gentle question. A yard manager says "we just end up guessing on Fridays". You say "guessing on Fridays?", and wait. People nearly always explain, and the explanation tends to hold the detail they wouldn't have offered to a direct question.

Write numbers down as you hear them

Customers mention numbers in passing: the size of the team, how many orders a day, how long a check takes. Write each one down where they can see you do it, and read the set back at the end of the call. Numbers confirmed in the meeting become the baseline everyone agrees on, and the first sentence of your business case.

Leave room

Discovery calls go wrong most often because the engineer fills them. When you finish a question, stop. Count to five in your head if a silence feels long. If you catch yourself explaining how something could work, you have drifted into a pitch; ask another question instead.

Plan a short call around three outcomes

You rarely get more than half an hour with senior people. Rather than scripting the minutes, decide the three things you must leave with, and steer towards them.

Leave withSounds likeIf you run short of time
A shared picture of today"Can you walk me through the last one of these from start to finish?"Ask for someone who can show you, and book it before you hang up
The one or two problems that matter most, with a rough cost"Of everything you've mentioned, which would you fix first, and why that one?"Ask them to rank the problems by email afterwards
A next step with a name on it"Who should I spend a morning with next, and can you introduce us?"Never skip this one. A call without a next step didn't happen

Leave with something written

A great conversation is worth little if it lives only in your memory. Send a short recap the same day: what you heard, the numbers they gave you, open questions, and the agreed next step with an owner. A recap sent within hours signals that the meeting mattered, and it doubles as the first draft of the problem brief.

After two or three conversations, the brief should be able to state, on one page:

  • The problem, in one or two sentences the sponsor and the users would both sign.
  • Who decides, and how they will judge success, as a number.
  • The forces at play: fears, competing goals, the deadline and why it exists.
  • Boundaries: data that is off limits, systems that cannot change, required accuracy.
  • The baseline: what it costs today, in time, money or risk.

Try it

Rescue a vague first call

An insurance broker's head of operations says: "Our renewals team is drowning. We want AI to handle renewals." That is all you know. You have 30 minutes with her tomorrow and could ask for time with anyone afterwards.

Write six questions for the call: two situation, two problem, one implication, one payoff. Then name the people you would ask to meet next, and why.

Write your answer down first, then reveal the worked answer

Situation: "How many renewals does the team handle a month, and how many people work on them?" "Walk me through what happens from the renewal notice to the customer signing."

Problem: "Which step takes longest or gets stuck most often?" "What does a renewal that goes wrong look like?"

Implication: "When renewals run late, what happens: lapsed cover, lost clients, overtime?"

Payoff: "If the team had that time back, what would they spend it on?"

Next meetings. A team lead on the renewals desk (the champion) for the real workflow and numbers. Two people who process renewals, to watch the work and find the exceptions. Someone in compliance or IT, because renewals touch personal and financial data and may need regulated wording. A strong answer avoids any question that assumes the answer is AI, such as "which renewals could a model handle?"

Go deeper

Practise the skills