the sky floor

5 Thoughtful Questions You Must Answer Before Starting a New Website

August 23, 2022

We start new websites all the time for clients. It’s what we do. Often potential customers come to us with a vague need: “it’s time for a new website.” While the desire for the new isn’t wrong, it isn’t precisely a granite foundation for the job. 

To help solidify the footing of your project, here are five questions that have helped hone our client’s toward success.

  1. What big problem are you trying to solve?
  2. What does failure look like?
  3. Is the answer to your situation a new website?
  4. Why now?
  5. Okay, a website is part of the solution, but what is the best way to get that website?

What big problem are you trying to solve?

Why are you even thinking about a new website if there isn’t a problem? Just because you have the budget? 

A new website is useless unless you know what problem you are trying to crack. I will tell you right now that buying anything just because you can is the fast track to buyer’s remorse. 

One way to clarify the answer here is to imagine the website is done and has been online for six months and that you spent way more than you wanted on it – what result would make it worth the cost? What specific area would be frustrating if nothing changed? 

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Here are some everyday examples we see to help kickstart your thought process:

  • Our eCommerce sales are falling or staying the same; we want to grow!
  • Our design no longer matches our brand, which no longer matches the company’s vision and mission.  
  • We are launching our business and have no website. (This alone isn’t enough, actually!) A website is a critical pathway for our target audience to learn about who we are and what we offer. 

What does failure look like?

Okay, you know more about what problem you are aiming to solve, but how can you dive deeper into how to solve that problem? 

Identifying what failure would look like will help carve the path to success. That way, you can take another road if you know where the expansive potholes are. Think of this like an if/then statement. If failure is blank, this will happen, or, alternately, we can do this. 

Here are some examples:

  • Failure is not launching by the biggest tradeshow of the year. If we don’t launch by the big show, our most tailored will not know about our new offerings. 
  • Failure is sales continue to drop even with a new website. If sales continue to drop, then we can A/B split test our landing pages to find higher converting calls to action. 

This exercise will help you uncover what you truly want, what to avoid, and how to get there. If you can’t answer all the questions you raise (what even is split testing anyway?), it’s time to bring that up with your service provider so they can help you find solutions. 

Is the answer to your situation a new website?

I hate even to bring this one up. What kind of website agency asks if you even need a new website? Well, this one does. Look, the goal of marketing isn’t just doing things for no reason. You can probably move the needle with a new website, but what if that isn’t the real solution to your problem? 

This question will clarify if you are headed down the right path. Maybe there is a solution that doesn’t involve a new website. After you have asked the two questions before this, you realize a website is a mere bandaid. 

Your big problem could be a lack of new signups for your app, and your co-founder thinks a new website will drive more signups. But as you answer the above questions, you realize a new influencer social media strategy will move the needle further and faster than a website could. 

After all, you are reaching for goals, not merely going through the motions. Specific goals need specific solutions. Not just any old action will do. 

Maybe you can’t rule out a website altogether, but it isn’t the most pressing problem/solution, so you re-order your priorities. In other words, we need a website, but not before we redefine our mission. Discovering this before you start the website project will save time and money and push your goals onward. 

Why now?

What is remarkable is that you can have solid answers for every question before this but waffle on this one. Unlike the reasoning of an exasperated mom, “because” is not a good enough answer. Will doing this work now help you achieve your goals, or are you distracting yourself from the hard work? Will watching the situation unfold over time help clarify the path forward? Or will it hurt more to wait any longer? 

Here is the thing about “why now”? If you don’t have any sense of urgency, it will be hard to finish the work and inspire anyone working on it to make it a priority. I am not advocating waiting until it is almost too late to get your website project done, nor am I saying there is a specific time frame that classifies as urgency – that will be different for everyone. But answering this question will help you understand what you want and when you want it, which will help you communicate those desires to your boss, employees, or vendor. 

Okay, you need a new website, but what is the best way to get that website?

Another question that a web company shouldn’t be asking. How can you build your website in a way that reaches your goals, no matter what that means? (Hint: it may not involve a custom build.)

This is a dangerous question for us from a revenue standpoint because the answer may well be Squarespace (although it isn’t as easy to use as they want you to think.) But sometimes, a complete custom website will not help you reach your goals more than a simple Squarespace site might. Why wouldn’t you do it if it isn’t going to help you move the needle? Or what if urgency is an issue? It might be faster to use a self-service option with themes than custom because custom takes more time. Or you might be creating a Minimum Viable Product, and the cheapest/fastest way to test is the best way right now. 

Conversely, you may need to stand out in a sea of look-a-like websites, and a template won’t cut it. Or perhaps you need CRM connections that Wix and Squarespace couldn’t dream of making. Or maybe time isn’t a huge issue, neither is money and in your field, status is critical – so having a custom website helps achieve your goal in and of itself. 

Figuring out your problem, the urgency, and how to solve it with the right tools will set your website project up for success before you start reaching out to providers. If answering these questions sounds daunting on your own, The Sky Floor offers a workshop to help you clarify what you need, reach out here to start the conversation. 


Answering these questions will help you avoid getting 95% of the way there and then fussing over the last 5% so much that you never arrive. Start with the end in mind, and your business, and vendors, will thank you!