Is It Time to Redesign Your Website?

I’m kicking off a redesign of the Boxcar Marketing site, and as luck would have it, a few Boxcar clients have recently done the same. So I thought—why not share the questions and thinking that make the early stages of a web project more successful?

Here’s the thing: I’m usually brought in after the new site is live, when someone says, “We need tracking!” And while I’m always happy to help, it’s much easier (and more effective) to build analytics into a site from the start. I’m excited to be involved at the beginning of a project—even if it is my own.

Why include developers and analytics folks like me earlier rather than later: We can help shape how your goals get translated into design and functionality. That means better data, better decisions, and fewer headaches.

So, whether you are redesigning now or thinking about it down the line, here’s a peek at what to consider in the discovery phase—the very beginning of the process.

🧭 Step 1: Get a Project Manager (Ideally One Who Knows Digital)

Your web agency or design team should have a project manager who understands your goals, your audience, and your content. Their job is to help you launch a site that’s not just beautiful, but also effective, efficient, and easy to manage.

And if you’re DIY-ing or leading the charge internally, you may be the de facto PM—so here’s what needs to happen next.

🕵️‍♀️ Discovery: Ask the Right Questions, Early

The discovery phase helps everyone align on what the site is for, who it serves, and how it should function. It also sets the stage for smarter design decisions—and measurable outcomes. Here are the types of questions to answer upfront. Your answers here guide design, but also analytics, and development. Plan so you can measure, measure so you can improve. 

🔍 1. Goals & Strategy

• What are your top 1–3 goals for the new website? (e.g. generate leads, showcase products, sell stuff)
• What’s not working with your current site?
• Are there specific metrics or KPIs you want to improve?
• Are there websites you admire or benchmark against?

Those last two questions are a good way to involve your analytics person. They can help benchmark where you are today and set targets for the new site. Plus they may have comp sites worth reviewing.

👥 2. Audience & Use Cases

• Who are your primary audiences? (Go deeper than “readers” or “teachers.” What job are they trying to get done by using your site?)
• Are there secondary audiences? (e.g. media, agency partners, collaborators)
• What questions do people ask in their first email or in-person interaction?
• What hesitations do they have before choosing you?

📄 3. Content Strategy

• What content do you already have—and what’s performing well?
• What do you wish you had more of? (Downloadable documents? Tools?)
• Will you reuse or rewrite content? Do you have a voice/tone guide?
• How often do you plan to publish new content?

Your analytics buddy can easily answer what content is performing well. And they can report on what content is present most often in successful user journeys.

⚙️ 4. Functionality & Features

• Are there integrations or platform constraints (Shopify, WordPress, etc.)?
• Will you keep your current website/blog platform, hosting?
• How do you manage your newsletter signups (Mailchimp, Substack, etc.)?
• Will you offer gated content or downloadable resources?
• Do you need booking tools or custom forms?

The actions you want visitors to take are a guide to what can and should be tracked. Ensure the dev and analytics teams are involved in this discussion before wireframes and designs are generated. 

🎨 5. Design, Structure & Feel

• What do you want visitors to feel? (e.g. “I want to buy that,” “This is useful”)
• Are there colours, fonts, or brand elements to keep or ditch?
• What visual tone suits your audience? (Minimalist, artsy, editorial?)
• What accessibility considerations are needed (contrast, font size, etc.)?

💡 Why This Matters

When dev and analytics are looped in early, we can:

• Ask clarifying questions about goals and user behaviour
• Flag functionality needs before you fall in love with a design that can’t be built
• Plan analytics tracking from the start so we’re not on the hop to implement a setup after the new site has launched or when it is too late in the process to ask for changes to code or style sheets that impact tracking
• Spot issues in QA that affect user experience or data integrity

Agencies that follow agile principles (as Kick Point explains here) often break work into smaller, collaborative sprints. This lets you test ideas, collaborate with stakeholders, adjust as you go, and avoid the dreaded budget or schedule overruns.

✏️ Takeaway: Start with Smart Questions

Whether you’re working with an agency or revamping your own site, the best results come from thoughtful planning across all stakeholders—marketing, content, dev, and yes, analytics. 🙋‍♀️

If you’re about to start a redesign (or even just dreaming about it), steal these questions. Use them in your kickoff meetings. Share them with your team. They’ll help uncover what your site really needs to do—and how to measure if it is working.

And hey—since I’m in redesign mode too…

Would you take 2-min to give me some feedback on the Boxcar Marketing site?
✨ Send a note to hello@boxcarmarketing.com

• When you go to an agency or consultant’s website, what is the most important content to see?
• What do you like or dislike about agency websites?
• Anything you want specifically on the new Boxcar Marketing site?
  • Something more interactive like office hours or a self-directed analytics course?
  • Downloadable resources?
  • More or less of what?

I’d love to hear what you think.