Understanding your business: why I don't take anything at face value

Last updated:
Oct 29 2025
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First published:
Feb 27 2023
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The most significant feedback I consistently receive from our clients is that I understand their business. This is always nice to hear, because it helps reinforce the value of my process in getting to ‘get you’. The accompanying comment on this feedback is always about how other designers have missed the mark in a true understanding of the business in question. And it all comes down to strategy, because if you don’t know why, then what’s the point, right?

why i dont take anything at face value photo faces

From business goals to digital strategy—why the why of it isn’t an option

When you come on board to work with me, one of the first things you’ll notice is that I ask a lot of questions. Often I even ask the same question multiple times and in lots of different ways. This can seem really boring and I know it’s off-putting to some potential clients—there’s a big time investment to this. But there’s a reason why I start with strategy at the beginning of everything I do, whether it’s designing a business automation workflow or a small buisness website.

Examples of what can go wrong when your needs are taken at face value

Situation 1: fancy design agency builds overly complicated website after failing to ask the right questions

A former client approached me for urgent help after the big, fancy agency they’d hired to build their new website was failing to deliver what the business needed. It was clear to me that, while there had been extensive pre-build meetings, no one had asked the right questions up front. The fancy agency didn’t seem to understand what the business priorities were; what role the website would play in their marketing and in ongoing client relationship management; and, crucially, how the small business intended to manage the website going forward (not with a full-stack developer on staff, that’s for sure!).

If you don’t have solid foundations you will have to rebuild your house.

Learning: bigger isn’t always better. The agency’s lack of understanding of this small business meant they delivered an enterprise-grade, code-heavy website that just wasn’t fit-for-purpose for a small, hands-on team. In short, the tech stack was wrong. Asking the right questions at the beginning would’ve got my client a better website that would last them longer. A year on and we’ve completely rebuilt this client’s website to ensure that all code is available to them and nothing is locked away or hidden. We’ve given them a bunch a global templates that they can reuse to create new pages and sections with ease. We’ve created a content system that makes it easier for the team to do what they need to do without having to be web designers themselves. And we’ve given them a ton of free training so they can get in and get to work.

Situation 2: skipped strategy led to miscommunication and a poor experience for both creative consultant and her client

several wires in audio mixers

 

A colleague needed advice after her consulting service failed to meet the expectations of her client, while simultaneously overstepping her own boundaries around how her service worked. The consultant had a strategy session embedded as part of her process, but the client was time-poor and elected to skip the session. My friend let it slide, made a bunch of (reasonable-seeming) assumptions, and got to work (we’ve all been there!). When her client saw the work produced, the outcome didn’t meet expectations. Uh oh. Miscommunication on both sides led to a disconnect that my friend then worked overtime to resolve to keep her client happy. This isn’t a situation exclusive to designers, I’ve seen similar situations with business coaches, lawyers, financial planners and consultants of all stripes.

Learning: starting with strategy goes a long way toward setting expectations, defining service boundaries, and fully understanding what your client needs (which may differ from what they say on paper because we don’t know what we don’t know!). This has ultimately turned out to be a huge win for my friend’s process going forward, as she’s doubled down on her process to ensure strategy is never skipped.

Reliable, professional and responsive, Nicole takes the time to understand the client’s objectives and identify the best strategy to achieve them.

Jasmine Hogarth, Make it Clear

Things start to go right when we take the time to understand each other

Situation 3: an expert external eye should be able to recognize opportunities to enhance your first draft

worm's eye-view photography of ceiling

 

A new client came to me with a fully fleshed out sitemap for their new website that, on the face of it, was ready to roll—they’d clearly put a ton of work into it. My client had already done a massive amount of strategy work with a brand designer, so their vision was very well articulated. It was up to me to go deeper and get to know everything about their business, their vision for the future, their audience and all the ins and outs of how they wanted to leverage the website—not limited to the surface level ‘I need a website‘ marketing angle.

After two in-depth Website Strategy Workshops that were included in their custom web design package, we restructured the sitemap to allow for a better user experience. Their initial draft was a massive first step that helped light the way. Our work together created a super solid plan of action that made the rest of this project a breeze.

Learning: don’t take what looks like the obvious path to be the right one. Going deep into the why of your business goals and audience expectations can mean flipping the switch on the first draft of your vision.

Situation 4: a friend wants to use Shopify because she likes the designer’s Shopify work better than WordPress.

A close friend of mine has been picking my brain and getting a second opinion on the various options available to her as she goes through the process of finding a website designer for her latest re-design project. My friend loves the work of a Shopify designer who has been referred to her and is less keen on the portfolio of a WordPress designer who was referred by someone else.

The thing is, my friend runs an expertise business, not a luxury linen shop. Shopify is hands down the best option out there for e-commerce stores. Whenever a lead comes my way for e-commerce, I’m quick to refer them on to a handful of Shopify pros I can vouch for, as I know it’s the best tool for the job and will better suit their needs than anything I can come up with.

Likewise, my vouched-for,highly skilled Shopify colleagues refer me for clients who are a better fit for WordPress. They know that WordPress is the best fit for an expertise business.

While these referrals are happening without the need for a strategy session, we’re all experts and digital design pros who know from experience when we’re not the right fit. But my friend, who doesn’t have this experience, needs to do the strategy work and have an expert available to ask the right questions to uncover all the unknowns around her business goals and what she needs for her new website. Those unknowns can be the difference between blowing your budget on the wrong tool for the job and making an investment that delivers ongoing benefits to your business.

As I told my friend,

  1. Any designer worth their weight will design to your brand guidelines, your design preferences, and specifications. I’ve designed plenty of sites that aren’t my cup of tea design-wise, but they align with the client’s aesthetic or a strong design direction preference. In fact, my own website reflects my design aesthetic, but literally none of my client websites look anything like this, because the direction is always led by a combo of client preferences and industry research specific to the job at hand. You can point to a Shopify site you like as inspo if you want, and that look could easily be built out in WordPress by your web designer. Never let the design determine the tool.
  2. Strategy and structure are actually more important than design. Yes, design is important too, and you want a website that conveys your brand identity. But trust an expert here: you don’t want a site that just looks pretty. You want a site that is discoverable, converts leads, and provides a good client experience. Design is a factor here, but it is actually not the lead factor many businesses think it is. Yes, you want a design you love. But getting someone who can apply that on top of excellent site structure is more important than a designer who draws the picture you like, which doesn’t help your audience and has zero benefit to your business. If you want to recoup the money you’re investing in your website redesign, you need someone with the experience to deliver results, not just a pretty picture. 

For more on what a website can do beyond just looking pretty, check out my article on Digital-First Business Strategies.

Situation 5: I’ve been that person who jumped right in without a plan. It’s how we all start out.

woman in black shirt and black pants walking on red and white concrete floor

 

When I first started this business over a decade ago, I did the whole jump off a cliff without a parachute thing. I lived the start-up life. I tried to hustle (ew). I said yes to everything, and I learned a ton. But I also wasted epic amounts of time, money, and brain space along the way. I worked too many late nights. I spent money on quick fixes that may have moved the business a step forward, but always took it two steps backward in short succession.

This story is not just my story. It’s the same for most of the expertise businesses I work with. Most of my clients started their businesses from a corporate exit. We often start a business because we’re saying no to what we did before that. And we work the rest out as we go along. Starting a business is huge. You know you’re an expert at your big thing, but there are a million other things you don’t know anything about that are suddenly part of your day job. It all gets messy, fast.

Learning: businesses that succeed always outgrow this stage of juggling chaos. We take on more of an investor mindset and look at everything we do in our business through the lens of building brand value and creating a scalable business with a viable exit plan.

That means slowing down, taking stock, and getting the right advice from people who have the knowledge and experience to ask the right questions.

I will always take the time to understand you and your business

These days I always start with lengthy strategy deep dives that take the form of Clever Day intensives, Website Strategy Workshops, or for the Marketing Solutions Roadmap that is a precursor to my vCMO program. Yes, it takes more time to get the strategy done. Yes, strategic consulting costs money. Yes, strategy means thinking deeply and doing your homework. But I’ve learned the hard way what happens when this important step is skipped. 

If you don’t have solid foundations you will have to rebuild your house.

That usually means more time for the consultant and budget blowout for the client. It’s almost impossible to retrofit this sort of connection—believe me, I’ve tried, failed and learned my lesson! Don’t be me, start with strategy, don’t be lazy about it, and create a solid plan of action to make every project a breeze.

Get the help you need from experts who understand your business

If you want to get to know us, subscribe to the Box Clever newsletter, read some articles, or book a Clever Hour strategy session to pick Nic’s brain and find our more about the clever things we can do to help make running your business easier.

Written by:
Nicole Sidoti

Photo of Nicole Sidoti pushing up glasses

Hey, I’m Nic. I’m a digital design strategist on a mission to make your clever stand out. Because the world is better when we’re clever, together.

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