Asking better questions

As a Solutions Engineer, I sell software and show that the product I’m showcase is the right fit for the customer. The best way to do that is to ask more questions. For now, let’s take it by heart that asking questions leads to a higher credibility. Not only is it helpful for work, but also helps me quench my insatiable curiosity. What a wonderful job which aligns with my personality!

What’s your intention. Start broad and narrow in

Moving to the specifics, it’s very important to start with the end in mind. The intention is the north star which helps you guide your questions. However greedy you want to be by having an intention like “I want them to buy X” or “I want them to agree to Y”, it’s important to keep the intention open minded and curious. Leading questions can misguide both the asker and the listener which can result in unneeded answers or sometimes incomplete answers. Starting to cover the extended area of the topic in which the question is in helps not miss out potential opportunities.

Ex: “I need customer to buy my software” [Target Result] → “I want to know where the customer can use my software” [Intention] → “Can you describe your current processes in place related to X and Y” [Broad Question] → … → Do you think Xa is a top priority for you [Specific Question].

P.S. This technique does need you to know the playing field. And be ready to pivot if you realize if the direction of the conversation turns out to be different than what you expect.

Pivot Ex: “Can you describe your current processes in place related to X and Y” [Broad Question] → “We use process A in X which connects to C in domain Z and process C in Z is very inefficient today” [Answer] → Can you explain how domain Z is handled today [Pivot Question]

Types of Questions to ask

  1. Open Questions vs Closed Questions: If it’s a “Yes” or “No” question, it’s a closed question. Open questions are better in the beginning where you’re still testing out your hypothesis. Ex: “Can you do A?” vs “What do you do for A?”
  2. Legitimate vs Disguised/Leading questions: If information already exists in the question, it’s a disguised question and can be leading. Ex: “Don’t you think it’s hot?” vs “How’s the weather?”
  3. Hypothetical Questions: Hypothetical questions can lead to hypothetical answers. Asking such questions can be risky and asking for case studies might be a more useful question. Ex: “My situation is A. What should I do?/What would you do?” vs “Can you give me examples of something similar to A happening and how it was dealt with?”
  4. Clarification/Probe Questions: Asking for more details on the answer. Shorter the question, better the answer. Ex: “Tell me more”, “What made you do that?”
  5. Reflective Questions: Repeating the answer in the form of a question to elicit more context. Ex: “We do X and Y in our role which leads to A and B” [Answer] → “So, A and B are related to X and Y…” [Reflective] → More Details about the answer

How to ask

Do’s

  1. Start with open questions and based on the answer, either ask clarifying or reflective questions.
  2. You can also ask more open questions if needed.
  3. As you get more details, you can add more specific questions about a particular subtopic.
  4. Finally, as you can end with closed questions to get the correct answer you were looking for.

Don’ts

  1. Don’t string questions Ex: “How do you do A today? Do you think it’s a priority? How often do you use A?”
  2. Answering your open questions Ex: “How do you do A today? Usually, people use X and Y to solve A”
  3. Don’t lead to a closed question Ex: “How do you do A today?” → [Answer] → “Don’t you think it’s not an efficient solution” [Leading and Closed Question]
  4. Leave a question unfinished. Ex: “Can you do A today? Or…”

Types of Answers

  1. Truth (The Best)
  2. Lies, distortion and refusal: If you know it’s a lie, you can pivot by asking more specific questions, but if you don’t there’s not much you can do.
  3. Out of context: Redirect it to the right track.
  4. Partial answer: Ask clarifying questions.
  5. Avoiding answering, Stalling (asking another question as an answer): Be patient and use the next list to continue questioning.

P.S. Try to avoid Why and use the other 4WH questions because “Why?” can sound like you question their competency and make the person defensive.

Things to Remember:

  1. “Take your time, I’m listening.”
  2. Keep your agenda aside.
  3. Be available.
  4. Appreciate the other point of view
  5. Listen
  6. Try to imagine yourself in their place.
  7. Draw out feelings with questions.
  8. Ask speaker to elaborate.
  9. “Let me make sure I understand.”
  10. Be sensitive to speaker’s feelings.