By Mehdi HassanWhat questions should you answer before redesigning a website?
Before redesigning a website, answer six groups of questions: business goals, buyers, positioning, proof, existing search value and operations. Together they decide what the new site must say, which pages it needs and what it must not break. A website strategy workshop is simply the session where you answer them together, with the right people in the room.
We share the questions we use openly because the questions aren't the hard part. The hard part is answering them honestly, in sentences specific enough to publish. This framework sits within our hub on B2B website strategy, and it overlaps with what many agencies call the website discovery phase.
You can run it yourself with a founder, someone from sales and whoever owns marketing. Below are the groups, the questions in each, and how to turn the answers into a brief.
What happens in a website strategy workshop?
A website strategy workshop is a structured working session where decision-makers answer the discovery questions and agree on the site's job before anyone opens Figma. It produces decisions, not inspiration boards. In our own process the workshop sits at the start of the work, because we start with the words and the words depend on these answers.
Question group | What it decides | Who must answer |
|---|---|---|
Business goals | What the site is measured on | Founder or CEO |
Buyers | Who the pages are written for | Sales and customer success |
Positioning | The core message and category | Founder, product, marketing |
Proof | What evidence the site can show | Sales, customer success |
Existing search value | What must be kept or redirected | Marketing or SEO owner |
Operations | Platform, CMS and who maintains it | Marketing and engineering |
If one of these owners can't attend, send their questions ahead and get written answers. A workshop that leaves the sales questions to marketing's guesses tends to produce a site that sales doesn't use.
Which business and buyer questions come first?
Business and buyer questions come first because every later decision depends on them. If you don't know what a successful site produces, or who it's for, there's no way to judge a headline or a page list.
Business goals
- What should the site produce in the next 12 months: demo requests, trials, sign-ups, hires, investor confidence?
- What's broken about the current site, in the words of sales and of the founder?
- What's changing in the business that the site must reflect: a new product, market, price or segment?
- How will we measure the site three months after launch?
Buyers
- Who signs, who champions, who evaluates and who can block the deal?
- What do buyers ask on the first sales call that the site should already answer?
- Why do deals stall or get lost? Which objections come up most?
- Where do buyers research before contacting you: search, AI tools, review sites, peers?
The buyer answers usually reveal pages the old site never had. Our guides to mapping the buyer journey and writing for a buying committee show how to turn them into pages.
What positioning and proof questions does the workshop cover?
Positioning questions decide what you are, for whom and why you're the better choice. Proof questions decide what the site can show to back that up. They belong together, because a claim you can't prove shouldn't lead the homepage.
Positioning
- In one sentence a buyer would understand, what category are we in?
- What do buyers use instead of us today, including spreadsheets or doing nothing?
- What do we do better than those alternatives, specifically?
- Who is a bad fit for us? Saying so sharpens the message for good-fit buyers.
- Is our motion product-led, sales-led or a hybrid, and what's the primary CTA?
Proof
- Which customers have agreed to be named, quoted or written up?
- What measurable results can we state truthfully, with permission?
- What security, compliance and reliability facts can we publish?
- What founder or team credentials are relevant to the buyer's trust?
The motion question shapes the whole site, so it's worth its own discussion. See our comparison of product-led vs sales-led websites if the team disagrees.
What website discovery questions protect existing search value?
The website discovery questions about search ask what the current site already earns, so the redesign doesn't throw it away. Pages that rank, get cited by AI tools or attract links need a plan before anyone deletes or renames them.
- Which pages get organic traffic, and which queries do they rank for?
- Which pages have backlinks or get cited in AI answers?
- Which URLs will change, and where will each redirect?
- Do we need more than one language or region? (See our guide to multilingual websites.)
- Which buyer questions are we answering in AI search today, and which are competitors answering instead?
These answers come from data, not opinion, so pull them before the workshop. Our pre-redesign SEO audit walks through what to export. The AI side matters more each year: Ahrefs found the top organic result's click-through rate is 58% lower when an AI Overview shows, so the queries where you're cited may be worth more than raw rankings suggest. Our AEO checklist covers the page-level fixes.
Which operations questions decide the platform?
Operations questions decide the platform and CMS: who will edit the site, how often, and what it needs to connect to. A beautiful site the team can't update goes stale within months.
- Who edits the site after launch, and how technical are they?
- What content changes weekly (blog, changelog, careers) versus yearly?
- Which tools must connect: CRM, analytics, scheduling, product sign-up?
- Are there performance, security or accessibility requirements from customers?
- What's the budget for the build, and what's the budget for ongoing changes?
For example, suppose the answers point in different directions: how do you resolve it?
For example, suppose marketing wants to edit pages visually every week, while engineering wants the site in the same Next.js repo as the product. Those answers conflict, and the workshop is where you settle it. One common resolution is a Next.js site with a headless CMS, so marketers edit content in a friendly editor while the code stays in the team's stack. Another is a visual builder for the marketing site, accepting less code control.
The point is to make the trade-off explicit and write down who owns what. Leaving it unresolved means the decision gets made by whoever builds the site, often without the people who'll live with it.
How do you run a website strategy workshop yourself?
To run a website strategy workshop yourself, gather data first, answer the questions in order with the right owners, then write the decisions into a short brief. Here's the sequence.
Collect data before the session
Export top pages, queries and conversion paths. Gather sales call notes and lost-deal reasons. Run your main buyer prompts in ChatGPT and Perplexity and save the answers.
Send the questions ahead
Give each owner their question group in advance so the session is spent deciding, not thinking from scratch.
Answer goals and buyers first
Don't start on positioning until you agree on what the site must produce and for whom.
Draft positioning in publishable sentences
Write the homepage headline and subhead options live. Argue about words, not adjectives.
List proof and gaps
Separate what you can show now from what you need to collect. Don't let the site promise proof you don't have.
Agree the sitemap and keep-list
Decide the pages, which old URLs stay, and the redirect plan for the rest.
Write the one-page brief
Goals, audience, positioning, proof, sitemap, platform and success metrics on one page. Everyone signs off before design starts.
What should the workshop produce?
A website strategy workshop should produce three things: a one-page brief, a sitemap with a messaging hierarchy for each page, and a list of open questions with owners. If it produces a long slide deck and no decisions, it hasn't done its job.
The brief is what keeps the redesign honest. When someone later asks for a new section or a different headline, you check it against the agreed goals and audience. The sitemap shows each page's job, and the messaging hierarchy lists the headline, the main points and the proof in order, so copy and design start from the same plan.
Some teams bring in an outside facilitator for this step. If you're weighing that, our guide on choosing a website strategy consultant or an agency explains when splitting strategy from the build helps and when it causes handoff loss.
