Developing Questions for Your Next Informational Interview

One essential method to grow your skills, knowledge, and experience as an urban planner is to speak and learn from other leaders in your field or specialty. This is why I have dedicated to interview urban planning leaders and share it with you on this site.

I often struggled in reaching out to leaders because of my limiting belief that I wouldn’t be able to effectively engage in a conversation worth their time. To help me overcome this barrier, I developed strong, engaging questions that I felt confident would create a deep, engaging conversation. To become an urban planning leader, asking deep, engaging questions is a key skill to learn.

“The wise man doesn’t give the right answers, he poses the right questions.”

-Claude Levi-Strauss

In the interviews I have held myself, I developed my own questions that were unique to what I wanted to learn. Here’s how I did it:

Ask: What do I want to learn from this urban planning leader? I start by asking myself this question to determine my goal for the informational interview and how the person can help me grow. The answer is a guide to what questions you must ask for you to learn. For example, my answer may be, “I want to some advice on how to shift my career”, or “I want to learn more about Transit-Oriented Development”. Knowing this, helps me determine the focus of my questions such as, “in your experience, what is the biggest hurdle in changing your career path?” or “What case study should I research that you believe is a great example of TOD?”

Use example questions online and make them authentic to you. There are plenty of blogs that provide good example questions for informational interviews. Pick the ones that interest you the most, and put your own twist on them that align with what you want to learn.

Do your homework. Look up the person and the organization they work for to better understand what they do on a daily basis. This leads to more informative questions and better answers. Also, these leaders will respect your preparation and be more open to engaging with you. This will also avoid answers such as, “check my website, there’s information there.”

Start with simple questions. I like to ask very simple questions first to get the juices going in the conversation. Such as, “what are you working on currently?”, rather than leading with, “what’s the biggest mistake you made and wish you could go back and change it”. As the dialogue and energy picks up, ask more in depth questions to receive a better result. 

Provide context. If I ask someone, “why has transit mode share declined?” One, they may ask, has it? or why do you think so? Instead, use context as to where you derived the information and then ask the question: “After reviewing your Quality of Life study I noticed the percentage of transit mode share has decreased the last two years, why do you think that is occurring?” This gives the leader a better idea what you are asking and can provide a more informed answer.

Ask follow-up questions during the conversation. When the leader answers your question, ask follow up questions for three reasons. First, it shows you are listening and increases engagement. Second, it gives the opportunity to dive deeper into what the leader is saying. Third, it lets the conversation flow naturally. A prepared list of questions is your starting point and you may not get through all your questions within the time you have with the leader. That’s okay, the goal is not to get all your questions answered, the goal is to learn and grow.


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