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It happens: A company loves the design of their new website, yay. Analytics shows that it’s getting traffic, yay. But… it doesn’t seem to be drawing engagement, responses, or leads, boo.

Way back when the designer first talked to the company about creating their new site, they had to nail down a number of project-scope details. How many pages? What plugins are needed? They also likely covered business essentials, like what do you sell? And how can people get it?

All good questions, but they’re not the ones we’ll be talking about today. Here, we’re going to be digging deeper, for a discovery interview that goes beyond the basics, into the territory of marketing message strategy.

Why? So the good-looking website that the company paid so dearly for actually brings them new business. Y’know, that ROI thing.

Now, some designers are glad to accept the copy that the client wrote themselves, so they have something to fill all those nicely-designed pages. But to me, that seems like an auto dealership selling really sharp looking cars, but to keep the cost down, the customer is expected to provide their own engine.

In any case, below are some Discovery Interview tips and insights to help website creators get more seriously strategic. Ready to start digging?

One: Talk to The Right People

For a smaller company, you may be interviewing a company owner. In a larger one, you’d likely talk to a marketing manager or their equivalent.

But only half the questions you’ll be asking will be about the company; the rest will be key questions about customers – their needs, their circumstances, their pressures, their options, and their obstacles.

Therefore, you want to include the company’s sharpest salesperson or customer service representative in the conversation – someone who deals with buyers on a day-to-day basis. That’s who knows, first hand, common buyer questions, concerns, dilemmas, and priorities. That’s important, because addressing those issues is where genuinely smart strategic messaging begins.

Whenever I’ve interviewed the owner and the salesperson together, my questions inevitably triggered discussions. Those, in turn, yielded valuable insights that never would have bubbled to the surface otherwise. Funny thing is, I wasn’t the only one who learned something.

Two: Be Incredibly Prepared

If you only have a short list of questions for the interview, you haven’t done your prep. Look through the company’s website, read reviews, check out competitors, and take note of any industry trends. Be curious, and allow good questions to lead to wider courses of investigation.

Include some of the questions above about customer needs and challenges. Go a step further and ask how those customers feel about those needs and challenges. What are the various buyer personas, and which are most important to the company’s bottom line?

Ask what is special about the company, or why they’re a good choice for customers. Now, here’s a trick: Put the same question in different words, then ask it a little further on in the interview. Then do it again. Know what? Each time they’re put on the spot, your interviewee will feel the need to dig deeper within themselves to come up with an answer.

Another idea: Don’t just ask why their customers buy from them. Also ask, if someone with an interest chose NOT to buy from you, or not to buy at all, what might be some of the reasons? This line of query can prove especially valuable in tapping into the mindset of typical buyers.

Three: Take Your Time

Forced to really think about their company and especially its customers, that’s when the good stuff starts to emerge. Not after the first half hour of superficial responses. Maybe not even after the first hour.

More than a few times, getting up after a two hour interview session, I’d be reaching for the door, and the client would say something in passing that suddenly cut to the very heart of the issue. I’d stop, sit back down, and go, ‘can you say that again?’ That a-ha moment may have revealed the company’s overriding unique advantage –- and inspired their new home page headline.

Try asking the business person a question, then tell them to answer it from their customer’s point-of-view. Note that if you’re doing your job right, the process could be just a teensy bit squeamish for your interviewee, because, well, they’ve never quite thought about these important things, quite this hard, from the perspective of someone other than themselves.

I find it surprising how much people know about their customers, but by and large, those highly valuable insights aren’t leveraged on their websites or other marketing. Why? Maybe because nobody pushed them to dig deep enough.

On of the things we’re attempting to get to here is the key transition from what the company is selling to how customers benefit within the context of their own universe. Look close enough and you’ll realize they are not the same thing. It’s a transition that could put the company ahead of competitors who couldn’t quite make it themselves.

Four: Follow It Wherever It Goes

As much time and effort I’ve put into preparing questions for my discovery interviews, there have been plenty of times when the conversation veered into another direction, leaving the rest of my carefully-worded queries behind.

Was I resentful? Heck no. I was thrilled. Because that new direction delivered us to helpful new ideas, considerations, understandings and breakthroughs. Think of your interview questions as a starting point, because, really, that’s all they are.

For some reason, in-person interviews seem to yield the most fruitful and unexpected new vectors of inquiry and insight. Maybe it’s the non-verbal cues that we respond to, for a conversational synergy that’s not as easy or spontaneous in a phone interview. Zoom interviews hold a kind of middle ground here.

Sending the person a list of written questions doesn’t allow for the free-form possibilities of  going off-script, but it does give them more time to think about their answers. And it may be the only option for execs who are too busy to schedule time to talk.

Final Thoughts

If you’re like me, you appreciate a professional, well-designed company website. But if you’re like me, in the end, that’s not the gauge I use when deciding which vendor gets my money.

When a company seems to understand exactly what we’re trying to achieve, we take notice. When they also understand the obstacle that’s standing in our way, we feel a connection. And when they seem to have a unique solution for overcoming that very obstacle, then our mouse starts sliding toward the Buy Now button.

That’s not gonna happen if the company doesn’t clearly offer the right answers. And you don’t get to the right answers unless you start with the right questions.

I believe everyone can do this. But I understand that not everyone wants to. Companies and web designers who would rather let someone else handle the interview, the strategy, and the copywriting are welcome to reach out. Because once I start digging, who knows what good stuff might be uncovered.

So what do you do next after a productive and helpful discovery interview? Start the writing? Not yet. Read What You Absolutely Must Do Before Writing Web Copy.

You can also get other points and perspectives from A Guide to Running a Client Discovery Process from Hubspot, and Discovery Session for the New Project Step by Step from Mediium.


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Tom TortoriciAbout the Author:  Tom Tortorici is an Atlanta copywriter and web content writer who helps companies make a genuine connection with their audience. His classes and conference presentations have focused on how writing, strategy and design can work together to grab attention and interest even among readers with short attention spans. In addition to working directly with businesses, Tom regularly partners with web designers and marketing agencies.

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Tom Tortorici Inc. | Tom@TomTortorici.com | 770-934-7861 | 3101 Rockaway Rd | Atlanta GA 30341