You're about to spend real money on a new website or redesign.
The first meeting you have about that project—the kickoff—will do more to determine the outcome than your choice of tech stack or template.
Done well, a kickoff gets everyone aligned on why the project exists, what success looks like, and how you'll measure it. Done badly, it's a quick chat about pages and colors followed by a vague proposal and months of scope creep.
There's a reason so many software and web projects go sideways. Studies consistently point to unclear requirements, misaligned goals, and poor communication as major causes of failure, not just “bad code.” One analysis of software projects found that mismanaged requirements are behind about a third of failures.¹ The Project Management Institute is even more blunt, reporting that poor communication was a contributing factor in 56% of failed projects.²
A healthy kickoff is where you avoid all of that.
As one project management guide puts it, project kickoff meetings “establish alignment, clarity, and collaboration among stakeholders from the very beginning.”³ Another describes the kickoff as “crucial for aligning stakeholders and setting a clear roadmap, preventing scope creep and enhancing accountability.”⁴
This is what my kickoffs are designed to do—and what yours should do, whether you work with me or not.
Why the kickoff sets the tone for everything
A bad kickoff feels like this:
- You talk mostly about pages, features, and maybe design inspiration.
- No one asks about your business model, margins, or sales process.
- “Success” is defined as “launch the site by X date.”
That’s how you end up with:
- Vague goals
- Scope creep
- Misaligned expectations
- A site that looks fine but doesn’t move the needle
A good kickoff feels completely different.
We still talk about design and content, but those are the last things we cover. The first part of the conversation is about:
- What business outcome we’re trying to move
- How we’ll know if this project worked
- What constraints we’re operating under
It sounds simple, but most web projects skip this. And when you skip it, your developer or agency is forced to guess. That’s how you get pretty websites that don’t generate leads, “SEO” that doesn’t translate into revenue, and redesigns that quietly hurt your numbers.
A strong kickoff is essentially risk management: it reduces the chances that misalignment, unclear expectations, and bad communication will kill the project later.⁵
The 5 questions I ask in every kickoff
Here are five questions I ask in every new web project. If your developer isn’t asking some version of these, you’ve got a problem.
1. “What business outcome are we trying to move?”
Not “What pages do you want?” or “What do you want it to look like?”
Your website is a business asset. So the first question is always:
- Are we trying to generate more qualified leads?
- Increase online sales?
- Improve close rate by explaining the offer better?
- Shorten the sales cycle?
Until we pick a primary outcome, everything else is guesswork.
This also sets us up to define KPIs—the numbers we’ll actually track. That could be form submissions, booked calls, checkout completions, or something else tied to real value. CIO and digital transformation research is clear: shifting from IT-centric metrics to business-driven KPIs is what lets organizations prove the value of their digital investments.⁶
2. “How will we know 6 months from now that this was a good investment?”
This question forces both of us to get concrete.
Six months after launch:
- What needs to be true for you to say, “That was worth it”?
- Is it +30% more leads?
- Is it being able to see where leads are coming from?
- Is it lowering your cost per acquisition from paid channels?
I’ll often say something like:
“If we’re talking again six months after launch and you’re thrilled, what numbers have changed?”
You don’t need perfect answers on the spot, but we do need ballpark targets. Otherwise there’s no way to evaluate success later—everything becomes about feelings.
3. “What’s your current lead flow and close rate?”
This is where we get into your actual funnel:
- How many leads do you get in a typical month right now?
- From where? (referrals, search, ads, directories, etc.)
- Out of those, how many become real opportunities?
- Out of those, how many become customers?
This isn’t about interrogating your business—it’s about understanding reality so we can make realistic projections.
If you’re closing 20% of qualified leads now, and the site increases lead volume by 30%, we can sketch out a rough impact on revenue. That’s far more useful than “We’ll get you more traffic.”
It also sets up the conversation about unit economics: what a customer is worth to you (LTV) and what you’re comfortable spending to acquire that customer (CAC). Many SaaS and finance guides use a 3:1 LTV:CAC ratio as a basic rule of thumb for healthy growth.⁷ We don’t need to be perfect here, but we do need to be directionally right.
4. “Who’s actually going to use/edit this thing internally?”
This is one almost no one asks—and it’s why a lot of sites decay after launch.
- Who will update copy or publish new content?
- Who will review leads coming in?
- Who will own reporting and check the numbers?
If the answer is “uh… probably me?” we design for that. That might mean:
- Simpler editing workflows
- Fewer moving parts
- Clear, documented processes
If you have a marketing team, we design for them—permissions, content workflows, and the level of complexity they can realistically handle.
The point is: a healthy kickoff plans for the real humans who will own the site after we’re done.
5. “What constraints are we working with?” (budget, internal team, timelines)
Good projects respect constraints. Bad projects pretend they don’t exist until halfway through.
We talk openly about:
- Budget (both for the project and ongoing support)
- Internal capacity (who can provide content, review, etc.)
- Timelines (including events you’re trying to hit)
This isn’t about upselling you. It’s about making good tradeoffs on purpose.
If we know we’re constrained on timeline, we might:
- Focus on the 2–3 most important flows for launch
- Park “nice-to-have” features for a second phase
- Prioritize tracking and reporting over fancy visuals
If we know we’re constrained on budget, we might:
- Use a simpler layout system
- Cut down on custom animations that don’t affect conversions
- Invest more in copy + tracking than in extra page templates
A transparent kickoff acknowledges constraints instead of hiding from them.
What I show the client in the first 30 minutes
Kickoff isn’t a lecture—it’s a working session. Early on, I like to show three simple things.
1. A basic success metric framework
Nothing fancy. Usually something like:
Visitors → Qualified visitors → Leads → Opportunities → Customers
We plug in rough numbers from your current situation:
- How many visitors do you get?
- Roughly what percentage become leads?
- Roughly what percentage of leads become customers?
Then we talk about where the bottleneck is:
- Not enough of the right visitors?
- Plenty of visitors but low conversion rate?
- Leads coming in, but sales can’t qualify them?
This keeps us anchored in business outcomes instead of design opinions. As one CIO guide puts it, the point of digital KPIs is to align metrics with what your transformation actually aims to achieve—and to keep the list small and meaningful so people can act on it.⁸
2. How we’ll track it (without drowning you in jargon)
Next, we talk about tracking at a high level:
- GA4 to understand traffic, key events, and conversions
- Ad pixels (Google, Meta, etc.) to measure campaign performance
- UTM tags so we know which campaigns and content are working
- CRM (if you have one) to connect leads to real revenue
You don’t need to know how to configure GA4 events—that’s my job. But you do need to understand:
- What we’re tracking
- Where you can see it
- How often we’ll look at it together
Digital transformation KPIs articles all hammer the same point: if you’re not defining and regularly reviewing KPIs tied to customer experience, efficiency, and revenue, your digital projects become expensive experiments you can’t evaluate.⁹
3. Where decisions will be made and how often we’ll review numbers
Finally, we talk about cadence:
- How often we’ll meet (monthly, quarterly, etc.)
- What we’ll review on those calls
- How we’ll decide what to change or test
A simple example:
- Every month, we look at leads, conversion rate by channel, and CPA
- Every month, we agree on 1–2 changes or tests based on that data
- Every quarter, we zoom out and look at LTV:CAC and bigger experiments
This is how you avoid “set it and forget it” websites. It’s not about endless redesigns; it’s about making measured, data-backed improvements.
Red flags in a kickoff (what you should walk away from)
Just as a good kickoff has a recognizable feel, so does a bad one. Here are some red flags that should make you think twice about moving forward.
1. Vague promises with no plan to measure anything
If you hear:
“We’ll get you more traffic.”
…but no one talks about conversions, leads, or customers, that’s a problem.
Traffic without a plan to measure and improve conversions is a vanity metric. You can’t take “sessions” to the bank.
2. No questions about your economics (LTV, CAC, margin)
If your developer or agency never asks:
- “Roughly what is a new customer worth to you?”
- “What are you comfortable spending to acquire one?”
- “Do some channels produce better customers than others?”
…they’re not thinking about your business, just your website.
Benchmark studies on LTV:CAC often put a healthy ratio around 3:1 to 4:1, meaning each customer generates three to four times what you spent to acquire them.¹⁰ You don’t have to know your exact ratio in the kickoff, but if no one is even trying to understand your economics, they can’t make good recommendations.
3. An obsession with tech stack, no discussion of needs
If the conversation is 80%:
- “We’ll build this on [Framework X] with [Tool Y].”
- “We’ll use a headless CMS with a microservices architecture.”
…and almost nothing about:
- Who your customers are
- What they need to do on the site
- What outcome you care about most
…that’s a red flag.
Tech choices matter, but they’re implementation details. They should serve your goals, not replace the conversation about goals.
4. No agenda, no summary, no next steps
Healthy kickoff meetings are structured. They have:
- A clear agenda
- Time for questions on both sides
- A recap of decisions and next steps
Project management resources highlight that thoughtful preparation—sharing an agenda, clarifying scope, roles, and deliverables—and a clear follow-up are essential to effective kickoff meetings.¹¹
If your kickoff ends and you have no idea what was decided, what happens next, or how success will be measured, you’re already on shaky ground.
Bringing it together
A healthy web project kickoff isn’t about wowing you with jargon or a 40-page deck.
It’s about:
- Getting brutally clear on why the project exists
- Agreeing on how you’ll measure success
- Understanding your current funnel and economics
- Designing around the real people who will use and maintain the site
- Being honest about constraints and making tradeoffs on purpose
If your last kickoff didn’t look anything like this, you’re not alone. Most agencies and freelancers are more comfortable talking about tools and timelines than LTV, CAC, or close rates.
But that’s exactly why so many web projects end with, “It looks better… I just wish we could tell if it’s actually working.”
You deserve better than that.
If you want your next web project to start with clarity instead of confusion—and you want a partner who’s willing to talk about revenue, not just redesigns—let’s talk.
F2 Web Services
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