How to have more impactful/deeper Taro 1:1 member match convos?

The key to understanding what makes a conversation especially meaningful is realizing that 99% of people (even shy introverts!) greatly enjoy talking far more than listening. On your end, this means that you should try to listen far more than you talk.

But let's break down the talking part: When do people enjoy talking? It's when they get to talk about something they're deeply passionate about. So your operating mindset when going into the conversation should simply be this:

1. Find something the other person really cares about
2. Make them talk about it and support them with positive vibes

For #1, the easiest way to do this is to ask probing questions like "What do you do for fun?". This one might not work though as it can feel a bit aggressive, especially with naturally awkward people (i.e. most engineers 🤣). What is far more powerful from my experience is listening intently and then "picking up" something they're interested in. This shows to the other person that you're paying attention (hence you value them as a human being) on top of the value of letting them talk about a fun thing.

As an example, let's say they mention in a broader point that they were working on a machine learning side project over the weekend. You can pick up on that and dig deeper with something like: "That ML project sounds cool! What does it do?". If they're clearly enjoying themselves talking more about the project, you should foster that energy by asking more questions. On top of that, show interested body language by nodding along, smiling, and saying positive affirmations like "That's awesome!".

It's true that providing concrete tactical advice to someone is incredibly valuable. However, there's also a lot of value in being a friendly, supportive face, more than many people realize. At the end of the day, a lot of us just want someone to listen. Be that someone 🙏

I cover these concepts and a bunch of others in-depth in my Effective Communication course: [Course] Effective Communication For Engineers

In conversations in general, not just work related, it’s often helpful to take the first step going deeper yourself. Be comfortable and confident, and the other person will reciprocate if they want to. For instance instead of saying “Hey I’ve worked at xyz company for the last 2 years and I’ve been learning more about DevOps recently” try, “I’ve recently failed in this way …” or “I’m feeling like I’m struggling in this area …” and see how the other person opens up and relates.

Here are some counter thoughts to the hurdles you have:

1. Rahul always talks about the importance of empathy, so if you’re an engineer and they are a PM you could ask “What is something you want to tell every engineer you work with but can’t” or “What do you wish engineers did differently when working with product?”

2. If there is a big difference in seniority I believe that it is because your match is OK with that and they are there in a networking and growth platform as the mentor. Personally I bet it would be enjoyable then for them to answer your questions like “What led to your success” “What do you wish you knew sooner” and “What challenges did you overcome”

I believe Rozie was just posting about this and a great way to have honest, real, deep conversations would be to talk about failures (and of course what you can both learn from them).

Some hurdles I find:

• There might be a big difference in our roles (for eg. system eng and product manager)
• There might be differences in seniority where I feel like I feel like I'm not able to provide enough value to my match (I might not be able to provide any value/insight into any challenges/goals of my match)

I would try to keep an open mind because there might be more similarities than differences in the projects that both of you have worked on. It can be helpful to get the perspective of a person who is in a different role than you because it could help drive how you decide to navigate a project with different stakeholders in the future.

Also, you might not need to provide direct value to your match in the form of advice. There are many times where others can find value by giving you advice. It gives them a chance to refine their own thoughts about a particular subject. It also feels good when you are able to help someone else.

what mindset should I keep to have deeper/meaningful conversations

At the end of the day, we are all humans, and we all have different interests and struggles. I would try to tap into these. If someone starts to elaborate a lot about a certain topic, they are probably very interested in it, and you can tease out deeper questions about why they are so interested in that topic.

I just came across this post from Alex's post on LinkedIn. Can anyone shed light on how these member matching sessions happen? Is there like a random matcher or do people volunteer to connect over a slack channel?