The mini-guide to talking to your customers

Actionable steps to starting the process of customer discovery

Photo by Sebastian Herrmann on Unsplash

Ok, so you’ve gotten over the psychological excuses stopping you from swallowing your pride and getting yourself out there. You’re ready to talk to customers! Congratulations, you must be so proud.

Now for the million dollar question flashing in neon lights in your head: where the hell do I start?

I want to make something clear before I give anything remotely related to advice. I am far from perfect when it comes to talking to customers. And during the trial period of the Telora fellowship, I talked to 50 of them over the course of four weeks. So my number one piece of advice is to just go do it. And you will learn. But if you’d rather not shoot completely in the dark (although this method does works wonders, but just takes a bit longer), keep reading. The following advice is a combination of what we learned from Eliam, the founder of Telora, a great book called The Mom Test, and my own * humbling * experiences.

First thing’s first: who should I talk to?

Pick 3–4 customer demographics who satisfy three criteria:

1. They make enough money to pay you for your product
2. You are interested in helping and learning more about their profession or interests (a 5–10 year commitment here)
3. You have access to them in some way, shape, or form

These will be the few demographics that you will get acquainted with in search of a problem you want to solve with your startup. There are multiple ways you can approach brainstorming and finding these people:

Make a list of people. List all communities you’ve been a part of. Clubs, organizations, family, friend groups, jobs you’ve worked, places you’ve lived. Ask ChatGPT to help you brainstorm areas of your life to explore. In every community, list the people that you can reach out to through personal email, phone, text, LinkedIn, etc. A good rule of thumb: you know that if they see your name, they’ll respond. Narrow down these communities by the criteria above.

Who-where pairs. All specific-enough customer demographics should come in who-where pairs; that is, you know who they are and where to find them. Give that “where” a visit, get over any social awkwardness holding you back, and approach people. Eliam gave us quite a motivating example of a pair of founders he was mentoring who were targeting doctors, and spent 10 hours one day in a cafeteria in a hospital interviewing doctors. As part of our process, I spent 8 hours one day in a co-working space looking for startup founders to interview. Ask ChatGPT for ideas on the “where” if you can’t think of it yourself. Check online forums or discussions to see where people might meet up. Look for events or conferences in the area. After you’ve exhausted all options, there are cases in which the “where” might not be so feasible to visit; maybe the demographic works remotely (study café’s might be a good choice, though), maybe the demographic is too spread out, or maybe the demographic is high-end business clients working in corporate offices. In these cases, you might need to try other methods.

Think outside the box, then think outside that box as well. The Mom Test quotes some interesting examples of finding leads. The one that stuck with me most was someone trying to target the demographic of university board members. To find this audience, they invited board members from 3 top tier universities to a monthly discussion session during which they discussed the problems the universities were facing. Other smaller university representatives came to spectate and learn from these big 3. This is something that is attractive to all parties involved: the top 3 university representatives got to learn from one another and voice their concerns, the spectators learned from the big names of the industry, and the founder was able to gain firsthand insight on the problems the target demographic was facing. Consider finding ways to teach and/or gather your target demographic. That is, organize workshops on a topic related to your product or demographic’s interests. Organize a happy hour for them to meet up and discuss their problems and gain insights and advice from one another. Think outside the box.

Referrals. We’ll discuss this more when we get to the actual content of an interview, but always keep this in mind. Ideally, you’ll only have to get a handful of people to agree to an interview, and you’ll get more people out of each person in the form of a referral. Usually, if someone you interview has someone they’d like to refer you to, they’ll ask you to write them an email post-interview (and even if they don’t ask, you should anyway), in the form of: Thanks for chatting, we’re working on a product that solves abc problem, thanks for agreeing to introduce me to xyz, have a great day.” With this short blurb, it’s pretty easy and frictionless for them to forward the email to someone else they think might be a good fit. Referrals can also come without an interview; look back at the list of people you made above. Do any of them know someone who might be useful to talk to? If you’re a student, professors are great, approachable people who know a ton of other people willing to talk.

Your goal getting started should be to just find a few people willing to give you 15 minutes of their time to chat about their problems. Don’t be discouraged if you can’t line up 100 interviews in two days. People are busy.

Before the interview: some psychological reframes

Great, so you’ve lined up an interview or two. You just met someone who wants to chat, you’re about to enter someone’s office, or you’re about to join the Zoom call. There are a few psychological things to remind yourself about.

1. You’re about to change someone’s life for the better. They are not doing you a favor by talking to you. If anything, you’re doing a favor for them. This reframe is important because it’ll change the way you approach the interview and it’ll change the way they perceive you. You’re about to solve a problem that has been draining their time, energy, or money, and you’re about to give them firsthand (probably discounted) access to it. Thank them for taking the time to chat, but don’t talk to them like you owe them anything.
2. You want to probe until you learn something new. It isn’t a failed interview if you realize they’ll never be a customer. It’s only a failed interview if you don’t learn anything new, whether it’s about the problem space, your target demographic, or the solution you’re building. You should be deathly afraid of at least one question you’re asking because it might invalidate your entire startup, or else you’re playing it too safe (which will only waste your time).

What do I ask?

Now that you’re mentally prepared, it’s time to execute.

If it is the first time you talk to the person and you’re in the early stages of customer discovery, this interview is focused on learning 1) what the person does, 2) what problems they face, 3) what they’ll pay you to solve their problems for them.

A successful interview must end with you knowing the next steps with the customer (it’s fine if that means no next steps). Decide before the interview what the advancements you want from the customer are, and practice asking for them. I know this sounds stupid, but this is usually where the fumbles come in, and we get embarrassed.

The questions you’ll want to ask during the interview will go something like this:

So you have profession xyz (or complete activity xyz). Can you walk me through your typical responsibilities, or what a typical day looks like? What kinds of things do you do?

This is an intro question so you’ll know what you want to ask them about, and to get an idea of the activities that dominate their days (this is where their largest issues will likely lie). From this response, pick the one that is most relevant to you and your product or interest, and we’ll probe with this one further.

You can skip this question if there’s a specific activity that you know you want to focus on (like the process of conducting research for professors, for example).

Tell me about the last time that you completed (insert the selected activity).

This will give you concrete details about the actual experiences that the person goes through, rather than anything hypothetical. If they give a one-line example, ask them to expand and give you the specific steps they go through and things that they do. You’re on the right track if their initial response to the question is “oh, I do it every day”, or “actually just an hour ago”.

What is the hardest part about doing (insert the selected activity)?

You want to know what they’re really burning to solve.

Why is it hard?

You want to know why there isn’t a solution. Is it something that can’t be solved? Is it something no one cares enough about to solve?

What tools do you use now to solve (insert hardest part about the activity)?

The ideal answer to this question is that there is a makeshift solution in place that kinda sucks, or they are combining a bunch of different tools to achieve the desired effect, but the system doesn’t quite fit.

What shortcomings do these tools have?

Understand why they are unsatisfied with their current system. Sometimes they won’t be, and that’s okay. In this case, maybe you can learn about the things that work great in their current system that you can incorporate into your product. Or maybe you’ll learn about your competitors.

So, just to make sure I got it right, (repeat back to them what they just told you about their struggles and problems).

They should confirm with, “That’s right!” It’s important that you make sure you understand before you try to sell.

Let me tell you something great. We’re building a product that solves (repeat back to them what they wanted solved in the form of a product).

And then, shut up. There’ll be a few seconds of an awkward silence. That’s okay, just stay silent. You want an honest, genuine reaction. Here’s an example of a few:

“How much does it cost?” Bingo. Right on the money. Throw out a number that’s reasonable (or on the higher side) and see how they react.

“When/how can I try it out? Is there a beta version?” Bingo #2. Although it’s not a hard money commitment, they’re showing genuine interest.

“Oh, cool idea. Let me know when it comes out.” Ehhh. Not all hope is lost, but not usually a good sign.

It takes a while of interviewing to really begin to nail setting up and interpreting this part. Be careful here for empty promises, compliments, or fluff words.

With the fact that I’m building software for (xyz demographic), is there anything else I should have asked you?

Here they might tell you another issue they care about finding a solution to more than what you’ve discussed. They might give you a tip about the demographic that you didn’t know otherwise (I’ve heard things about the requirements of a software to get lawyers to use it, for example). They might tell you a question that you should ask future interviewees in this demographic to learn more about what they do.

Finally, who else should I talk to who would be able to provide similar insights or who would be interested in a product like this?

This is a very awkward question to ask, but wording it like this will reap more benefits than saying “I’d really appreciate a referral…” or “let me know if there’s anyone else…”. Try to get an answer on the spot, and if you don’t, send a follow up email with the blurb I mentioned earlier (you should send this regardless to make their lives easier when referring you to others).

Ask for your advancements if you haven’t already.

It’s time to swallow your pride and embarrassment and ask for the advancements you planned for before the interview. This is likely the question you should be terrified of before entering the conversation. But remember, you’re helping them. You’re asking if they want to move forward in the process of making their lives better.

What just happened?

You’re going to hear a lot of information even over the course of the 15 minute interview format I described above. It’s important to know what this all means, and what accurate, non-biased takeaways you can move forward with from each interview. There are various outcomes you can leave with:

The interview that “went well”, and actually went well. An interview falls in this category if afterwards, you can recap concrete, specific facts about what they do and why they do it. You also got concrete commitment: you know what the next steps with this customer are. This means that the interviewee sacrificed something of value, whether that’s significant amounts of their time (in the form of a more involved follow-up interview or shadowing session), their reputation (they referred you to their boss or someone else who has more autonomy to make a decision), or, obviously, their money.

An interview that “didn’t go so well”, but actually went well. This means that you realized the person isn’t probably a fit for your product. However, instead of giving up when you realized this, you probed further to understand a few extra things: is the “problem” not actually that big of a deal? Or is this person fundamentally different from your ideal customers? Do they not care about this specific implementation, or are they just worn out from hearing too many pitches and empty promises? Or are they just tired today? This is useful information to guide the rest of your customer discovery. Maybe they know someone else who might be a better fit as well. You still showed interest in their lives and their problems, so they want to help.

An interview that “went well”, but actually didn’t go so well. The interview ended with something along the lines of “let me know when the product is released!” Or maybe the person showed that they had the problem you are targeting, but it was prompted by “But do you ever have issues with…” Reflect back on the questions you asked and make sure none of them were leading or prompted biased answers.

An interview that “didn’t go so well”, and actually didn’t go so well. They clearly weren’t a good fit for your product, and you ended the interview when you realized that. You didn’t get any referrals, or any new information from this interview. Remember, there’s something to learn from everyone.

After each interview, look back at your detailed notes and jot down a few things: 1) what problems they have, 2) a few bullet points summarizing their existing practices and sentiments, and 3) next steps with this customer. Then act on the next steps. Reach out to the referral, schedule the next time you’ll chat with them, give them the beta version to try out, etc. Just the act of reading back through your interview notes will likely help the takeaways stick, and re-evaluate things you misunderstood or misinterpreted.

They are interested in investing more time. Now what?

The second time you meet with them (and probably a few times after that), you’re going to want to get your feet wet and your hands dirty. For us, one of the target demographics we were targeting were productivity tool consultants. So we had a few of them walk us through a sample consulting session. We consulted for a few individuals and business ourselves. There was a team that Eliam told us about that began to shadow a doctor they were trying to help. You need to learn more about the actual details of the things they discussed in that initial interview to learn more about the problem space. This way, the solution that you build will be more personalized and helpful.

That’s a wrap :)

This is just scratching the surface of all you can do with customer discovery. If you skipped to this part in hopes of finding an epiphany or the magical advice I saved for the end, here it is: just start. You’ll learn much more by going out and struggling a few times than you will by reading a blog post like this. If you would like to keep reading more, though, I recommend checking out some of Paul Graham’s essays and the book The Mom Test.

The earlier you get used to having customer discovery interviews as a part of your regular routine, the easier it will become to overcome the social and psychological struggles that accompany these conversations. They should become part of your routine, as important as creating the product itself.

Happy customer discovery!