How to nail discovery interviews in presales like a journalist


I love discoveries.

For the stories to be uncovered. The challenges to be revealed. The customer’s triumph to be unlocked.

💎  If done righta discovery helps you helping your customer best. It will save you a lot of time during the demo preparation. Because you know exactly what to show for maximum impact, how to phrase it, and why.

👉  Now, here is the issue. A discovery is probably the most empathetic, people-centered part of our profession. Still, presales tends to work discoveries like a technical check list.

Don’t do that.

🔊  Stop working discoveries as a demo engineer. Experience them as a Journalist.

Here is how.


(1) Know your interviewee

Do your homework. First, cover the dimension of content. Find out as much about the person’s company; check the website, news, annual report, strategy papers, analyst reports, publications. Research the subject you are going to cover; industry sources, professional organizations, whitepapers. Most importantly, research the person you are going to meet. Online research is likely to reveal your interviewee’s professional background, areas of expertise, publications. This is the ground work to understand your interviewee, build a rapport, and draft meaningful questions.

“The preparation is the same whether you are going to interview a diplomat, a jockey, or an ichthyologist. From the persons’s past you learn what questions are likely to stimulate a response.” (A.J. Liebling)

❇️  Pro tip: Second, cover the dimension of language and behaviour. Look for video material to familiarize yourself with the person’s language, posture, gestures, and facial expressions. Why?

(A) Save time. Once you are familiar with how the person communicates, you save the important first few minutes of a meeting to build a rapport with the interviewee. Otherwise, you’d be wasting your brain computing power on analyzing and evaluating communication patterns. Consciously or unconsciously.

(B) Provide comfort. To make your interviewee feel comfortable, you adapt your communication style to theirs (e.g. analytical/ driving/ expressive/ amiable). Find out what’s what in advance to tune your questions and flow.

(C) Mind the gap. You need to understand the person’s usual communication patterns to detect unusual patterns during your interview that give interesting clues.


(2) Prepare your questions in advance

Every time you go into an interview, have a sense of what you want to explore. Prepare the goal for your meeting. Be it to understand the business use case better, to get a real user feedback to build your persona for the big show, or to gather the important success parameters from a management sponsor. What you need from this person to get your work closer to where it needs to be?

Write down your questions. These are deducted from your goal, from your research, and from your company’s resources such as product specific discovery questions.

Work out an interview flow. One of the hardest and most important pieces to develop. A balanced flow will help you to balance conversation and result orientation. Along this thread you figure out what and why you are going to ask next while your interviewee is answering your current question.

“The flow of questions needs to seem natural and conversational — don’t spin your subject off on a completely different topic just because that’s the next question on your list. Think about segues and transitions.” (Sarah Stuteville)

❇️  Pro tip: Be ready to throw your prepared questions and flow out of the window. Adjust to the situation. If you reveal an exciting new aspect: go for it. Or, on the contrary, if you face an interviewee who’s really not up to the task that day: let it go, make the best out of it. Don’t stick too much to the script. It’s your safety net. You can come back to your notes to be sure you cover the most important aspects (mark them accordingly).


(3) Humanize the interaction

❌ Don’t dive into the matter right away. (Unless you learned in your preparation your interviewee dislikes chit chat of any sort.) It’s a conversation between two people after all. You are not going to milk a cow for information.

❌ Don’t use any professional hook as a starter for your conversation. No current or former employer, nothing related to their career. Unless there is a very specific, unusual, anecdotal piece that is worth and interesting for your interviewee to elaborate on.

❌ Don’t use cheap talk. Weather, traffic, sports, and the like. Superficial. Just don’t. The person will not feel valued just because of that.

✅  Do develop an authentic curiosity in the person. Make notes during your preparation about pieces that strike you as interesting, or that establish an unexpected relation between you. (No, studying at the same university isn’t good enough. Been taught by the same professor? Warmer… You get the point.

❇️  Pro tip: if you did a thorough preparation and are honestly interested in the person, you are likely to establish a sound connection. Don’t fall into the trap of compromising what you need to know from the person in favour of too much friendly talk – and running out of time. Happens more often than you’d think.


(4) Ask what you need to know

Now that the lights are on, go for the information you need. Which, sometimes, is easier said than done. It’s different to prepare an interview on paper and pull through when you are sitting next to your interview partner.

“Some reporters are courageous only when they write, when they are alone with their typewriters, not when they face the person in power.“ (Oriana Fallaci)

Be aware of the basic toolset of asking questions.

Use open-ended questions, to widen the conversation, let your interviewee lead the way, and explore an interesting aspect. Effectively use closed questions to bring him/ her back to the thread, or to validate a statement with a straight yes/ no.

Silence is your friend. Sometimes you just have to shut up and wait. Endure a few seconds of awkward silence to give your interviewee the chance to carry on with truths he/ she wouldn’t have revealed otherwise. Just a few seconds, though. Listen to your instinct.

Use paraphrasing to ensure you understood your interviewee’s point, or eliminate ambiguity in an important statement. If you didn’t understand something you hear, ask for an explanation. Don’t act as if you got it when you didn’t.

Sometimes you achieve great results together when you ask your interviewee for his/ her opinion on a topic (“How would you…?”, “What would your solution look like…?”); opposed to just asking him/ her about facts on the topic (“How does this work?”).

Once you got stuck in an unspecific descriptions of your interviewees status quo, simply ask: “Please show me how you do…” There nothing like experiencing the person’s current situation seeing what he/ she sees and doing what he/ she does.

Try to look behind the curtain. Get a clue on why a person says the thing he/ she says. Is it truly the person’s perspective? Or is there an agenda, and you are being made believe something? Other than confronting the person directly, try to constructively work out the persons motivation. Glimpses of emotion (or the absence of it) will give you an idea.

“Assume nothing, question everything.” (James Patterson)

❇️  Pro tip: Occasionally, you will meet someone who doesn’t understand why you ask all these questions. At all. No way. Of course this is to end in a poor response outcome. Deadlock. Be confident to hit the break in such situations now. Walk the interviewee briefly (!) through your process of discovery and solution design. Then tell him/ her which results you require to move on. In 3 out of 4 cases you will break the deadlock.


(5) Watch, note, and listen

Here is another continuum you have to manage well during interviews: make notes of what is being said while paying attention to your interviewee. Sounds simple, isn’t easy.

Perceiving and processing how things are being said is as relevant as what is being said. Meaning: you have to pay attention to language, facial expressions, gestures. Is this statement spoken with confidence? Hesitation? Is your interviewee feeling comfortable, stressed, nervous? That’s all crucial information for you to (a) adjust your interview style to the situation, and/ or (b) to notice a topic you could explore/ should avoid.

Short: keep eye contact with your interviewee. (Rest assured, there’s another set of detailed techniques to it, too. Like: Lower your eyebrows, keep your palms up, don’t overdo eye contact.)

Having a great conversation with positive personal vibes is not the only goal, though. You gather crucial information to build a suitable solution to your clients (un)detected challenges. Wherever possible, record your call or web session. You have all eyes on the interviewee, and you can use a video-to-text transcription software later. Of course, not every interviewee is fine with being recorded.

❇️  Pro tip: Even when you use a voice recorder, you may want to take written notes of crucial statements or such that are important to the interviewee. The action of noting them down signals to the person your understanding of the importance.

You made sure your results will get collected. Now, listen. Listen deeply. That means: 100% attention, no interruption, no judgement, no advice, show empathy, be curious. Listen like a baby.

“Think of the tremendous acts of attention and concentration that babies make to explore sounds and speak their first words, to learn language and communicate through listening.” (Pauline Oliveros)

Pauline Oliveros coined the term Deep Listening. “Deep Listening is both a framework and a process. When people use Deep Listening they listen in a fundamentally different way, ask more revealing questions and embrace more nuance. When a speaker feels they are being deeply heard they are more likely to convey an enriched narrative, reflecting not just their positions but what’s truly important to them, their motivations and their values.” (Emily Kasriel)

Stop a second and let this sink in.

Think about yourself.

🤔 Imagine you are in a situation when you want to tell someone what you truly think and how you really feel. You start talking. Then imagine the listener rushes you through what you have to say. Mumbles “mhmm”, and continues with an unrelated question. Cause is the next one on his list. Would you reveal any relevant information to that interviewer?

👎 Me neither.

👉 Now imagine you sit next to a person that signals you with every fiber of his/ her body that what you have to say is important.

👍 Feel the difference?

This is the listener, the interviewer you may want to become.

I’m interested in you as a person, and I think that what you feel is important. I respect your thoughts, and even if I don’t agree with them, I know that they are valid for you. I feel sure that you have a contribution to make. I’m not trying to change you or evaluate you. I just want to understand you. I think you’re worth listening to, and I want you to know that I’m the kind of a person you can talk to. (Carl R. Rogers)


On a closing note

A discovery conversation is probably the most underestimated art of presales. Literally every aspect of it requires intensive practice and reflection to master it: Research, preparation, humanizing, listening, asking.

It’s hard to build these muscles. And it will take time.

❇️  Pro tip: One prerequisite non-negotiable despite all techniques you can train. A genuine interest in people, their stories, their world.

Investing effort to build these muscles will be rewarding. These capabilities will enrich both your professional and private life.

“The interviewer always learns something new from the interviewee. It opens up your mind to new ideas and the vast multiplicity of human experience.” (Steve Cosson)

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