My Experiment to Have More Meaningful Conversations

My typical day is filled with 3 kinds of conversations.

1. 2-10 seconds. I like to call this a “freshmen dorm conversation.” I’m now five years removed from college so I’m not sure if I’m still allowed to make college analogies but here it goes: you see someone who you lived with in a freshman dorm and haven’t seen since. You say hello, and the conversation follows a set pattern: “Hey, how’s it going?” They reply “Good, how are you?” and you move on.
2. 30 seconds – 3 minutes. This is someone who you see on a semi-regular basis and you start the conversation with general questions and maybe have time for a weather-related or current events topic. Then, you close up shop and move on.
3. 3 minutes+. This does not seem like a lot of time, but how many of these types of conversations do you really have? To keep a conversation going longer than three minutes there has to be mutual interest and at least one meaningful topic of discussion.

I generally tend to have Type 2 conversations. This could be because I help run a startup and meet a lot of startup people; everyone I meet has his or her elevator pitch or talking points well rehearsed. In fact, I have a lot of conversations that are abridged versions of “the show,” which to me means anyone describing his or her startup with a positive spin.

I don’t know about you, but to me these Type 2 conversations are frustrating – especially when talking to interesting, intelligent people working on startups. It’s not really a secret that every startup is horribly broken anyways.

Entrepreneurs are eternal optimists, so I understand the impulse to use a positive word shield to hide what is really going on, but I wonder how helpful people would actually be if you let them try. For example, whenever we had office hours at Y Combinator, the partners would always ask what our most pressing problem was, and those sessions were incredibly productive.  This made me wonder, what if I did this with people who I see every day?

After having any idea, I run it by my “Am I crazy?” filter: my mom. She lives in a no B.S. world and is the perfect first person to run any idea by. Her response, “you are probably crazy. People don’t have time for your problems.” Since both of these are probably true, we created an important rule for a potential experiment. Don’t tell people my most personal problems, yet. Until I have a better idea whether this works or not, my shared problems will strictly be work related.

Like any supporter of the lean startup philosophy, before talking to anyone else or even writing this post, I decided to test this idea once. I’ve been going to the gym pretty regularly for the past two years and there is a guy who I see there a few times a week. We’ve probably had hundreds of Type 1 conversations and at least twenty Type 2 conversations. I still didn’t know his name or where he worked. He was a nice, anonymous gym guy.

This time, however, when he asked “How’s work?” instead of responding “Going great,” I replied that we had just launched our new app, Clippo, in the app store and were having a real problem with our user acquisition strategy. Namely, that paid apps and gaming companies had driven user acquisition costs so high that it made it very difficult for a consumer product without an extremely high budget to be competitive.

Gym guy didn’t respond with “that’s tough, good luck,” which is what I half-expected. In fact, he explained how the company that he works for created an optimized system for AdWords that would help us reduce costs and create a framework for user acquisition.

To quote Eminem, “Ah wait, no way, you’re kidding. He didn’t just say what I think he did, did he?” An insight and a strategy in my first Type 3 conversion experiment!

I made sure that I really understood what he had just explained to me. I asked at least five to ten follow-up questions, and gym guy answered each one patiently. I could tell he really enjoyed talking about his strategy and was excited to share it with someone who he knew was obviously grateful. How did I know that? I asked him.

I actually will be implementing his Adwords strategy over the next few weeks and, depending how it works for us (his company is in ed tech), will potentially write a post about it.

But my favorite part came after that – he told me one of his problems. For privacy sake, I won’t share what it was but am happy to report that I had a couple ways that I thought might help him. By approaching him with my problem, I think it made him comfortable enough to share something with me. Again, it is important to remember that before this we had never had a conversation for longer than 2 minutes. I wouldn’t say we are friends now, but I do know his name.

That exchange is what gives me real confidence that this can work. Another question my mom brought up was, “Is the average person going to know or care about your startup problems?” At first I had no answer, then I came back thinking “probably not and that is a good thing”. One thing we struggle with from time to time is uniformity of ideas. Christian and I work so well together and think so similarly that sometimes we are too close and too involved.

I’d love for some of my friends or anyone, maybe someone who works in finance or materials research, to tell me how they think I should acquire users. Maybe it will be awkward and they won’t care or have ideas, but maybe they will come up with something or some accessible group that I would have never considered. That to me is an exciting outcome.

This brings me to my plan: try and take one Type 2 conversation and move it to a Type 3 conversation every day. (My philosophy to stick to a plan is to take them one small step at a time.) Then, in every one of these conversations, I am going to lead with my most pressing work problem and write a post about how it went.

If the first couple weeks go well, I’m going to add personal problems to the mix. If it’s a disaster, I can always record them, make a reality show, and drive viewer growth using strategic Adwords placement. Someone asked me what my goal for this experiment is and honestly I don’t have something I’m trying to learn. I just want to see if it works for me. Am I missing something, how do you drive meaningful conversation in your life?

Big thanks to Nick Meyer, Melanie Major, and Sheila Vashee for editing.