How to ask good questions?

Ask Good Questions

Seeing, listening, and touching are primary sources of information about the world. Every new project, new sales campaigns, new product ideas are based on a number of assumptions. As a sales/pre-sales person or product manager, your life depends on your ability to ask good questions. How do you know if a problem is worth solving ? How does your customer buy? When do they buy? Who do they buy? It is better to ask hard questions than losing the deal later or fail to create the right product.

The only way to discover all of these is to ask good questions, or observe a process/workflow or shadow your users. A vast majority of knowledge is stored in people’s heads, not codified in documents despite the huge investments in codifying such knowledge. Most common problems is that the interview is poorly conducted and you do not answer your questions or validate your assumptions. If you want to make that sale at the end of quarter or year or make that product a real hit, challenge your assumptions at the beginning of your effort. There is only one way to do it. You have to go and talk to your customers, users, partners, or stakeholders and ask questions. In my experience of working in enterprise product development, implementation, and sales, asking questions is a surprisingly hard skill. I had to spend lot of time to learn it from others, and it still feels intimidating. Here I want to summarize my learnings so far for my own benefits and possibly help others in the community. This is a long summary combining couple of books and podcasts stated in the References.

First, going by Charlie Munger[1], let’s invert the problem. Focus on what are NOT the good ways to ask questions.

1) Asking questions is NOT about finding a way to pitch your product. A natural tendency of pre-sales and product managers is to try to sell others at every opportunity. At discovery meetings your job is to learn not to pitch. You are looking to confirm or reject your assumptions. You are looking to make decisions. For sales team, you may want to find out whether customer is really interested in your solution or for product team, you are looking for patterns that help you prioritize product roadmap.

2) You have to be careful not to take what you hear literally. You want to uncover your customer’s’ functional needs and emotional wants, but do not create a “faster horse” — meeting the requirements literally. After the session, you will have more confidence on how to position your product, whether you are on a right track, or you have to change your plans. Do not ask any prediction and requirements questions. Your customers/users can not predict the future.

3) If your customer just want to see latest cool stuff from you, that may not be a useful discussion. You are looking for willingness to buy and who could help you build a “coalition” so that your product is actually implemented after sale and creates business value, not sit in the shelf. Interviews are not just for gathering data or show off your technical skills, it is for testing your hypotheses and building relationships.

4) Avoid asking unnecessary situational questions. The examples of such questions are: What software you use now? How old is the current version? How many people work in your department? The customers quickly become bored or impatient if asked too many of these questions. In digital age, you should be able to find these answers from your online research, conferences/networking, or paid subscriptions.

Now lets look at the journey of asking questions. You will get most out of your time if you start with a good foundation and map your interview journey. Start from the assumption that everything you know is WRONG. Here are the core set of five steps [2,3]:

  1. WHAT, staging the scene — what do you want to learn, write your assumptions, and hypotheses, and design your questions.
  2. WHO, design the stage,- Know your personas, select your actors.
  3. HOW, WHERE, and WHEN.
  4. Let the play begin- Ensure an effective session.
  5. Dance of interpretation- Synthesize and Make sense of what you learn.


Prioritize what you want to learn. Identify your assumptions and hypotheses about your customers, product, and partners-whether you are brand new company, launching a new product to existing customers, or selling additional features to an installed base. Two biggest risks you have with your current assumptions are: 1) you are not solving the problem customer has, 2) your solution is not attractive enough. If you want rigor in identifying assumptions, you may want to complete a “Business Model Canvas”[4].

Most of these interviews are guided, concentrated, focused, and open-ended communications. The questions must be written in the form of a flexible interview guide, but you must be able improvise based on the situational understanding during the interview. Your goal is to test your assumptions and hypotheses, not any generalization or statistical analysis. The good practices in preparing questions include[5]:

  1. Focus on current behavior, task, and process— because the current behavior is your most important competition- How your customers are behaving today, which may predict their future behavior. What they are capable of doing? What they are comfortable with? What decisions they make? Typically, as an interviewer, you want to uncover multiple realities and create a deeper understanding with real life examples- stories of personal/professional experiences and retrospective recall of experiences, feelings, and thought process. Focus on understanding usual, frequent events but also perspectives on rare events. You are mainly focused on “descriptive” questions- “What” “Who” “How” “Why” . Avoid questions that start with is, are, would, and do you. Asking Yes/No questions does not provide any insights you may need, so avoid those questions.
  2. Chunk up: Abstracting up allows you to look beyond immediate jobs and see opportunities for high impact changes. For example- “By meeting your service level, what would that get you?” “ If you are successful, what else could you achieve”, “if you are not successful, what else would be impacted”.
  3. Current constraints, choices, and actions: You need to understand the types of constraints limiting your customers because that will help you understand what types of solutions will be attractive and effective. You may see that customers may not perceive something as a problem or have limited resources, or certain cultural and social expectations.
  4. What frustrates or motivates your customer? No matter how good is your product, it requires efforts and investments from the customer. You need to uncover what motivates your customer, what makes him feel successful as well as what types of frustrations would be a deal breaker. The people who build products, they are usually comfortable with uncertainty. But most customers are not. And motivations may vary. Some are highly competitive and wants promotion and others may just want a “thank you” note.

Best practice examples of questions you can ask in customer situations:

  1. Tell me about how you do <xyz> today..
  2. Tell me about the last time you used something like ……….
  3. If you could wave a magic wand and be able to do anything that you can not do today, what would it be?
  4. Last time you did <xyz>, what were you doing right before you got started? Once you finished, what did you do afterwards?
  5. What are the consequences if you did <xyz>?
  6. What are the consequences if you did not <xyz>?
  7. By doing <xyz>, what would that get you?
  8. What specifically is challenging about <xyz>?
  9. Last time <xyz> happened, how did you feel? How did your boss/coworker/family react?
  10. Why do you think <xyz> happens?


Take great efforts to understand users and their current experiences- What are their habits, abilities, needs, and environments? When do they need your product? Why do they need you? How do they access your product? What are the factors in their life that will drive them to buy this product?

For early stage companies, you need to be very specific here- think through the kinds of people who have the problem you want to solve. They may have a particular job title, professional and social associations, and live in particular parts of the world. For example, if you are working on hospital operations management solution, you may want to talk to hospital administrator who would buy the product and hospital workers who would use the product.

Another important caveat here is that, your users are different based on your technology adoption lifecycle. Not everyone will be ready to buy or use your product on day one. For a new product, you need to find people in the left side of the technology adoption cycle- innovators and early adopters. These are usually the folks who has a strong pain point and would not mind trying a new unproven and unfinished product and services. For example, for hospital operations management software, you may want to target customers who are stuck with a old, archaic, and unresponsive vendor and paying high maintenance contracts.

You must also know the difference between “Customer Evangelist” (person is excited to bring a change), “Economic Buyer”(person with budget), “Technical Buyer”(approves the solution), and “User”(uses your product). For example, if you are developing a fitness device, your users may be the employees, but your economic buyer may be the HR department’s benefits manager who will help add your product in company’s benefit package.

In general, you start your sales cycle by talking to mid-level managers and employees than a C-suite. It is easier to get their time, have repeated follow up meetings, and helps you learn before you present to C-suite.

Lastly, even if you are an expert in your industry, you are not the user. You have biases, rational, and beliefs of your own, which will be harmful for your product/company if you try to act like a user.


How to find customers to talk to? You may have sales team or marketing team that may help you recruit. You could use personal connections, social media, websites, and physical places to find the people who may benefit from your product. Talking to Humans and Lean Customer Development and many sales training books have lots of examples and scripts you may use. If you are reaching out to people who would consider it a burden to talk with you, you may be approaching the wrong people. Asking for advice is the default method. People like to feel important and the people must benefit their own self interest by associating with your vision and telling you what they know. They see you and your solution as something that may help alleviate their current challenges. So, it is their best interest to give you all the information needed to execute on a solution.

Observing the customer in his natural setting is the best method for interview- this is validated by qualitative researchers. He may be able to show the current application he is using. You can see how his office is set up and who comes to his office- noise level, neatness, and privacy level of his working environment. In addition, you can see the face and body language, which helps you understand his deep feelings and helps you build relationship.

Another qualitative research method is to conduct interviews in a neutral location- helps you build rapport in a relaxed setting and you could talk to two or more people together and want to avoid distractions by coworkers. The next best option is video interviews (zoom, skype interviews), you have the benefit of seeing the facial expressions and body language. The last option is phone interview, you do not get any visual info, but can learn from verbal intonations and pauses.

Let the Play Begin- Ensure an Effective Session:

Have someone to take notes or record the interview if possible. And Plan for informed consent, confidentiality, and protection strategies if required in your situations, practice self presentations, and conduct pilot interviews if you are new in this area. You may plan to record the interview, however, in most cases, this is not a good idea. The interviewees may be more cautious in this situation and may be subject to legal restrictions.

By this time, you know your assumptions, hypotheses, personas, and know what you want to learn, devised questions, scheduled your interviews, and taken care of basic logistics. Now, you have to actually conduct the interview. Recently, I listened to Tim Ferriss show with Larry King[6], where Larry King explains how he controls the interview and tone of the conversation. This podcast would be a good use of time in your next business travel.

Here are some guidelines I summarized from various sources on interviewing:

  1. Be honest and clear on the purpose and agenda of the meeting and confirm the time. Make the interviewee feel confident that he will be helpful. Launch into one or two easy and warm up questions.
  2. Express genuine curiosity: Keep the tone conversational and encourage stories, pay attention to nonverbal communications, encourage silence- sometimes golden. Look for anything that is full of emotion or takes you by surprise. “Emotions” are the areas of opportunity.
  3. Be unobtrusive: You must act like a keen observer than a participant. Your behavior or attire should not draw attention.
  4. Be unassuming: You may have some degree of technical or professional knowledge regarding the topic. It may introduce bias and runs the risk of threatening the interviewee. Play down your expertise. Use phrases like “ your personal experiences” “for you specifically” “in your world” to emphasize that your interviewee is an expert.
  5. Be a reflective listener: By reflecting back what you hear, you can better understand the subject matter and move the relationship to a deeper level. Practice intense listening. Encourage him to go more detail about the things he is excited about.
  6. Avoid questions that may inject bias: The questions like the following needs to be avoided: “Don’t you think ……..? Would it cause a problem if …….? Would you agree that ……? Would you like if……….? These are generally result in “yes/no” answers and not helpful insights.
  7. Lastly, Smile.

Dance of Interpretation- Synthesize and Make sense of What You Learn:

Now is the time to start talking what you learned and use those to guide your decisions. Interpretation is a complex and dynamic craft, with as much creative artistry as technical excellence. There are many changing rhymes, multiple steps, moments of joy, revelation, exasperation, and the process is sweaty. The steps may include:

  1. Know yourself, your biases, and preconceptions. Consult your team and keep looking for alternative interpretations. Charlie Mungers biography[1], Thinking Fast and Slow book [7], and farnamstreet blog[8] are good places to learn decision making biases, heuristics, and mental models.
  2. Share the details with yourself, your team, and management team.
  3. Look for aspirational talk vs. real talk. You need real behavioral evidences.
  4. Focus on anomalies — they are the window to insight.
  5. Get critical feedback. A solo analysis is a great danger to self and others.
  6. Be wary of over identifying with customers/users.

Your job is not to look for things that support your interpretation or hypothesis, but to find out what might be wrong with it. An assumption deserves a some degree of trust when it has survived serious attempts of falsification. Analyze potential biases due to interviewee’s stakes in specific outcomes or due to their position in the organization. An essential check is triangulation- multiple sources and multiple methods (Observation, Interviewing, and Internet Research).




[3]: research/book9279




[7]: Thinking Fast and Slow:

[8]: Mental Models:

Disclaimer: I have no associations and financial interests in the references mentioned in this article. The opinions expressed here are personal, not the opinions of my current and former employers.