How to Start the Conversation

Most website projects don’t fail at the design stage. They fail at the first meeting, when nobody asks the awkward questions. Here are the questions I ask, and why I ask them out loud.

While everyone else is at the beach

Some people spend August horizontal. I spend it asking questions.

Summer is quietly the best season for this work. Nobody is shipping, everyone is slightly more honest, and there is finally time to think about the thing that has been on the “we should really fix the website” list since March. So while some are on the beach, others are starting new conversations — figuring out how to tell the story of a brand, a foundation, a product, a company.

I recently started working with an NGO, and it reminded me of something I keep running into.

The people doing the best work often tell the worst story

The organizations that most need a strong narrative usually have the weakest one.

That’s not a criticism, it’s arithmetic. Every hour and every euro spent on communication is an hour and a euro not spent on the actual program. So the website becomes a leftover — built once, in a rush, by whoever was available, and then quietly ignored for four years while the work itself gets better and better.

Meanwhile the ask keeps getting harder. An NGO website has to move someone emotionally and reassure a funder’s compliance officer and be usable by a person on a shared phone with 2 GB of data. That’s not a website. That’s a diplomatic mission.

These clients do their work brilliantly. They simply want to understand how to tell that story on digital platforms. That is a fair thing to want, and it starts with a conversation.

Why the first meeting is spoken, not sent

I never email a questionnaire and wait for a document to come back. I go through it out loud, in a discovery meeting, with the people who actually know things.

Here’s why. A written answer gives you the answer. A spoken answer gives you everything around it — the hesitation, the sigh, the “well, technically…”, the moment two colleagues look at each other because they clearly disagree about who the primary audience is. You are not listening for the answer. You are listening for the pause before it. That’s where the pain points live, and pain points are what you’re actually being hired to fix.

Technical details travel fine by email: hosting, CMS, analytics, who owns the domain, what integrations exist. Send those ahead, collect them asynchronously, save everyone’s time.

The essence only shows up in conversation.

A few things worth noticing while you’re in the room:

• Who answers first. That person usually holds the informal authority, whatever the org chart says.
• Who goes quiet. Often the person closest to the users, waiting to be asked.
• Which question makes everyone laugh nervously. Congratulations, you found the real project.

Why two questionnaires and not one

I could have written one generic template. It would have been useless to both groups.

A company is mostly answering questions about a transaction: who buys, who decides, who else they’re considering, what makes the offer different, what “success” looks like in leads or revenue, and which internal team owns which form.

An NGO is answering to several audiences at the same time, and those audiences want opposite things. Program participants need clarity and safety. Donors need proof. Funders need governance and reporting. Media need a fact. Volunteers need a form that works on a phone. And under all of it sits a category of question a commercial brief never has to ask: whose story is this to tell, who consented, what gets anonymized, and what happens if someone wants their photo taken down two years later.

Asking a foundation “what is your business model?” isn’t just imprecise. It’s slightly rude.

So there are two editions, and they diverge where they should.

What’s actually inside

Company Edition — 9 sections, 80 questions Business snapshot · Customers, users, and market · Brand and positioning · Website goals and user journeys · Content and structure · Features and integrations · Visual direction · Current website and technical setup · Project scope and decision-making

NGO Edition — 10 sections, 93 questions Organization and mission · Communities, audiences, and stakeholders · Identity, values, and voice · Website goals and desired actions · Programs, content, and impact · Ethical storytelling, consent, and safeguarding · Functions and integrations · Visual direction · Current website and technical setup · Governance, scope, and decision-making

Both are landscape A4 with response fields, one section per page. That’s deliberate: they’re made to be shared on screen during a call, or printed and scribbled on with a pen, whichever way your client thinks best.

How to use them without turning the meeting into an interrogation

Ninety questions read out loud in sequence is not a discovery meeting, it’s a deposition. Use the template as a map, not a script.

• Skip freely. Not every question applies. The ones that don’t apply are still telling you something.
• Short and honest beats polished. If you get marketing language back, ask the question a second way.
• Have several stakeholders answer the strategy sections separately, then compare. The disagreements are the finding. This is the single highest-value thing in the whole document.
• Separate three things as you go: facts, assumptions, and decisions nobody has made yet. Most project chaos comes from the third pile being mistaken for the first.
• For a small site, stay with the questions that clarify the offer, the audience, trust, and the contact journey. Everything else can wait.

What you end up with is not a filled-in form. It’s the raw material for a website brief, a sitemap, a content plan, a feature list, and — the part everyone forgets — a definition of what success looks like six months after launch.

Yes, use AI. Just not for the part that matters

Paste either questionnaire into whichever AI you use and adapt it: to a sector, to a specific client, to a language, to a shorter format for a 45-minute call. That’s a great use of the tool and you have my blessing.

What AI can’t do is sit in the room. It can rewrite the question; it can’t hear the pause. It will happily invent a plausible answer on your client’s behalf, and plausible answers are exactly what a discovery meeting exists to eliminate.

Use it to prepare. Use it to synthesize afterwards. Do the middle part yourself.

Take them

Both templates are free.

→ Download the Company Edition
→ Download the NGO Edition

You can adapt them for your own organization or your client work. Please keep the attribution if you pass the original file along, and don’t resell them as a standalone template. Beyond that, they’re yours.

If you’d like more of this — the templates, the teardowns, and the occasional strong opinion about design — the signup box is right below. No volume, no filler, just the useful parts.

Every great product starts with understanding people. Let’s start there.