I attended a local networking event to meet new people for my undercover problem discovery work. My primary goal was to get people talking and learn about their current struggles and how they’re trying to solve them.

To do this, I asked a lot of questions. People’s faces lit up, eager to share more. I was met with, “I’m glad you asked.” Or “Now that you mention it…” And “Funny you ask because…” Someone proclaimed that this was the deepest conversation they had had in recent history. (I started by asking, “so what troubles you these days?”)

I didn’t want to interrogate them in a one-sided conversation so I stopped asking. The roles reversed and they asked, “So what do you do?” I stumbled through my abstract. “I have a hard time being compassionate towards myself. I get very critical and it makes it difficult for me to practice self care. I want to see if this is a struggle shared by other people and see if there is a way to solve this problem.”

Oh wow, that’s interesting.

That’s a tough problem to solve. Good luck with that.

Well, good for you!

🦗 🦗 🦗

a sad, awkward monkey staring down at the ground

How would you carry the conversation from here on?

The way I see it, there are four paths one can choose to take, in my order of preference:

  1. Share how the problem affects me: I can take a more casual approach and talk about how the problem I’m looking to solve affects my life. This could be a great opening to establish a connection and to get to know each other better, if they’re willing to reciprocate and empathize.
  2. Share my “why”: I can expand on why I’m passionate about the problem I’m trying to solve. This could be another great way to build rapport and create a deeper connection without feeling like I’m building up to “the pitch.”
  3. Share my process: I can delve into my research and plans to tackle the problem. This could inspire ideas or creative solutions from unexpected sources.
  4. Shuffle Away: Change the topic, walk away, or if the conversation is still salvageable, put your undercover user researcher hat back on and continue asking questions.

In most of my conversations last week, I reached option 4 within a few minutes and walked away. There were two reasons for this. Firstly, I wanted to respect their boundaries. Secondly, I interpreted the niceties as a lack of curiosity. It’s like dating: if they were genuinely interested, they would have been curious. If not, they weren’t interested in a meaningful way. That’s okay; I won’t force a conversation. However, there is another scenario to consider: maybe they didn’t know what to ask or how to keep the conversation going.

Ways to authentically carry a conversation

  1. Share first: To build rapport and find common ground, start by sharing a personal anecdote to make the other person feel comfortable.
  2. …but don’t monopolize the conversation: My general rule of thumb is, if I start to feel like I’m getting too comfortable with my monologue, then I’ve gone on too long.
  3. Practice active listening: Pay attention to nonverbal cues when communicating face-to-face. You can mirror their body language, repeat what the other person has said, and ask follow-up questions.
  4. …and don’t be afraid of silences: Active listening may not always mean you have a response ready. It’s okay to take a moment to think and process what the other person has said. A simple prompt like, “Tell me more,” can help you take the time you need without feeling uncomfortable.
  5. Ask open-ended questions: Open-ended questions allow more detailed answers, while closed-ended questions can be answered simply: yes or no. Even questions asking for specific info are closed-ended; for example, “What do you do for a living?” and “How are you doing today?” Both start with “what” or “how”, but are closed-ended.