When your team decides to start the customer discovery process there are several things you should know.
1. Don't pitch
Your customer discovery interviews are not about pitching your idea to people and getting a "yes" or "no". They're about finding out what problems/needs people have that you can try to solve. If you want to mention your idea to them wait until after your discovery conversation has ended.
2. Keep it casual
Don't start off expecting hours long conversations with potential customers. Schedule interviews that are 15-30 minutes and if the conversation keeps going, let it. It's easy for someone to give you such a short amount of time. If they run out of time and you have more questions you want to cover, ask if you can speak to them again. Too keep the tone even more informal, call it a chat rather than an interview. That's really how these customer discovery interviews should be handled, as conversations.
When you have short conversations scheduled to begin with you can also avoid wasting time with people who don't actually fit the customer segments you're looking for. Start off with qualifying questions that will determine if a problem exists.
3. Start Small
Finding people to interview can be a challenging task. Instead of going for the head honchos straight away, start with individuals who you know will be open to having a conversation with you and also fit the types of people you're trying to build a solution for. Toward the end of each interview ask as the interviewee if they know anyone else you should talk to. They might just give you a name, but they could open a new door by introducing you to someone you didn't have access to previously.
Scheduling time to talk with people can become an in issue in itself. Sometimes your initial conversation doesn't have to be planned at all. If you get a moment of time with someone ask them a qualifying question to see if they're a good fit to ask for a customer discovery interview.
4. Ask real questions
Think of the problem you're trying to solve. What actions lead to a person experiencing that problem? Do the people you're talking to see it as a problem? Not every person you talk to may have the same pain point.
Start your questions off broadly. Think about the cycle of events that lead a person to experience the problem. Get concrete examples from the past rather than hypothetical answers relating to the future.
Do they mention the problem specifically? If not, they might not see it as an important issue.
For each interviewee have three big questions. Ask the "scary" questions - questions that will force you to change (or disprove) your business. You should be terrified of at least one of the questions you're asking in every conversation. If you run into someone and don't have the ability to schedule time with them, ask them your big questions first.
Dig into interesting and unexpected answers to understand the behaviors and motivations behind them. Questions to ask are about your customers' lives: their problems, cares, constraints and goals. Modify your questions to best fit the interviewee. If they're answering your questions with only a "yes" or a "no", you're not asking open-ended questions.
Compliments: You can avoid compliments by withholding your idea from the conversation.
Fluff (generics, hypotheticals and the future): Use questions that anchor back to specifics of the past. The deadliest fluff is: "I would definitely buy that."
Ideas: Find out what the underlying motivations behind feature requests (ideas). Ideas and feature requests should be understood, not obeyed.
5. Have an end goal
The point of conducting customer discovery interviews is to find out if you have product/market fit. Once you have developed an understanding of your industry and customers you can begin showing the product, this is the time to cut through false positives and ask for a commitment.
Commitment: They are showing they're serious by giving up something they value such as time, reputation, or money.
Rejection: Asking for a commitment is not failure, not asking is.
Advancement: They are moving to the next step of your real world funnel and getting closer to purchasing. (Always know your next step after the meeting)