How to Talk to People, for Engineers

I’ve never been great at talking to people, especially strangers, but I’m much better than I used to be. In this post I’ll share some of the things I’ve learned in my quest to be a better human.

One of the easiest things you can do to improve your life is to get better at interacting with everyone you meet. The more good interactions you have in life, the more friends you’ll make, and the more doors will open for you. Being likeable goes a really long way. Humans are very social creatures, and we’re happiest when we have strong connections and communities.

The first thing I’ll say is that practice is extremely important. If you want to improve your skills, just keep trying until you succeed more often.

Find Ways to Engage #

I’ve never been what you could call an outgoing or extroverted person, but I’ve always looked for opportunities to make sure I’m interacting with new people. It’s good to make new connections, expand your network, and find friends. Most of the time the best way to do this is by meeting people face to face, in real life. These are a few examples of how I’ve done that.

In 2014 I decided to start driving for Lyft on evenings and weekends (while I was still working at Airbnb). I did this for 2 reasons:

1. When I exercised my Airbnb stock, I wound up with an enormous AMT bill and I wanted extra cash to pay it off
2. I figured that driving for Lyft would be a good way to practice talking to strangers which is something I knew I still sucked at

Driving for Lyft was great because I was forced to meet someone new and have a conversation every 20-30 minutes. I had a lot of memorable, boring, and sometimes downright peculiar interactions with a diverse set of random individuals (and groups, too).

Eventually I abandoned my Lyft gig, but it was very good practice. It helped me realize that most people are friendly, although plenty of people are jerks, and that if you speak to people kindly they are likely to reciprocate. Getting outside your comfort zone is hard, but the more you do it the easier it gets.

In 2016 I did a cross country bike trip (from SF to NYC) where I got to chat with lots of different people from a variety of different backgrounds. The thing that was most surprising to me during that trip was how nearly universally everyone I met was kind, friendly, and willing to help. People often stopped to offer water, food, or whatever. In some cases people even opened their homes to me.

On the very first day of the trip I got heat stroke on a country road near Modesto (the air temperature was well over 40°C), collapsed on the side of the road, and if not for a retired police officer who happened to drive by, recognize that I was in trouble, and poured water on my body immediately, I may not be here today.

These days I try to get out to meetups or events that seem interesting, especially those related to technology or startups. I’m not a big fan of social outings that consist primarily of binge drinking, loud bars, or expensive dinners, but I’m willing to make exceptions for the right groups of people.

The Digital Dimension #

When I first wrote this, I wasn’t spending nearly this much of my life talking to people through a screen. Then the pandemic hit and for a while that became the default. Even now, a lot of conversation still happens in Slack, Zoom, Discord, text, and DMs.

Here are some tips for effective digital communication:

• Turn your camera on for video calls when possible. Facial expressions and visual cues are important for building rapport.
• Combat Zoom fatigue by scheduling shorter meetings and taking breaks between calls.
• Be mindful of the “digital divide” – some people appear more confident online than in person, and vice versa.
• Join digital communities like Discord servers, Twitter spaces, or Clubhouse rooms related to your interests.
• Consider audio-first socializing like podcast-style conversations or voice chats, which can feel more intimate than text but less draining than video.

Research from Stanford¹ suggests that constant video calls are mentally exhausting partially because we’re hyper-aware of being observed. Try suggesting a phone call or walking meeting as alternatives when appropriate.

Listen First, Talk Second #

One of the first things anyone needs to understand about talking to people is that you have to practice listening first. If you find yourself doing more than 50% of the talking most of the time, you’re probably doing it wrong. If you’re constantly talking, the other party never gets to actually participate in the conversation and won’t be engaged. Avoid interrupting no matter how important you think your current thought is while someone else is talking.

A conversation should involve back and forth. It’s not a speech, you’re not there to talk at them, and you should make sure you hear their thoughts too.

This matters even more on video calls, where people talk over each other, pause too long, then start apologizing because the timing is off. Some tactics that help:

• Leave intentional pauses after someone finishes speaking to ensure they’re done
• Use visual cues like slightly raising your hand if you want to speak next
• In group settings, consider using the chat function to indicate you have something to add without interrupting

Get People Talking About Themselves #

I remember when I was younger I always had a fear of asking people personal questions. I was worried they might get offended if I ask them a question they didn’t like.

What I know now, that I didn’t know then, is how much people love talking about themselves. If you ask someone a question about themselves, they will most likely be happy to tell you everything they can about it until you interrupt them or change the subject. It also makes other people feel good because it demonstrates that you have an interest in who they are.

In other words: ask a lot of questions, and ask personal questions about them. However, make sure you know what’s appropriate and not appropriate for the given situation and level of familiarity.

If every sentence out of your mouth starts with “I”, that’s usually a bad sign. Try to say “you” more often when you’re asking questions or responding. Instead of “I think that project sounds interesting,” try “What excited you most about that project?”

Escalation #

You can’t start a conversation in big talk mode, you have to begin with small talk. From small talk you can move on to medium talk, and eventually from medium talk you can get to big talk.

Sometimes you’re allowed to break this rule, but it’s a pretty well established social convention that you have to start from small talk first. People are not likely to let their guard down around strangers right from the start.

I’ve noticed there is one short circuit for getting people out of small talk mode quickly: be funny. And if you’re not good at being funny, at the very least be genuine and kind.

I’ve also noticed that since the pandemic, some people will skip the warmup and go straight to something real. I’ve had perfectly normal conversations jump from “how’s it going” to “I think quarantine kind of broke my brain” in about thirty seconds. A question like “What’s something you figured out about yourself during the pandemic?” can get you there fast if the moment is right.

Have Shared Interests #

Conversations don’t go far when you have nothing to talk about. You can only say so much about the weather or the local sports team before you run out of things to discuss. And definitely don’t start talking about political or religious subjects unless it’s actually appropriate to do so.

One trick, which I have many times suggested to others, is to get a dog. I get approached constantly by strangers every day because of the fact that I have a dog, and she’s kind of cute. There’s a lot of other great benefits that come along with having a dog such as reduced risk of heart disease (likely because of having to walk your dog every day). A lot of people love dogs and it’s an easy subject to talk to just about anyone about.

If you don’t have a dog, then find groups of new people with shared interests to interact with. Try meetup.com, Reddit meetups, or whatever your preferred social platform is.

There are also way more internet-native groups than there used to be. Beyond traditional meetups, I’ve seen good ones built around:

• Virtual hobby clubs for everything from cooking to coding
• Online gaming communities that form strong social bonds
• Co-working Discord servers where remote workers gather to simulate office camaraderie
• Newsletter communities where writers and readers connect
• Cohort-based courses that create tight-knit alumni networks

I’ve met good people this way. Sometimes the internet is the easiest place to find the weirdly specific people you actually click with, and if they’re local you can always meet up later.

Be Approachable #

While the dog trick is a great way to make yourself more approachable, there are a few other things you can do as well. For starters, don’t walk around with headphones all the time (AirPods, sigh). Adjust your body language so you don’t look closed off to conversation. Don’t dress like a slob, but also don’t dress too fancy because it may intimidate some people.

Smiling is a fairly universal human signal of friendliness. If you can smile, do that.

In digital environments, approachability takes different forms:

• Responsive communication: Aim to respond to messages within a reasonable timeframe
• Personalized profiles: Use authentic photos and bios that share something interesting about you
• Active listening symbols: Use appropriate emoji reactions or short affirmations to show you’re engaged
• Visible availability status: Let people know when you’re free to chat

Offer Something #

To keep people engaged, it’s good to give them a reason to talk to you. If you want to meet the person again, tell them that. If you can help them in some way, let them know.

Don’t show up empty-handed. If you can help, help. That can look like:

• Sharing useful articles or resources without expectation of return
• Making introductions that benefit others
• Offering your specific expertise for quick consultations
• Highlighting others’ achievements on social platforms

A 2020 study by Harvard Business School found that people who engage in “generous” networking (focusing on giving rather than taking) build stronger and more valuable professional relationships over time².

Know When to Leave People Alone #

Cold approaches are hard, and sometimes people just don’t want to talk to you. It’s probably not personal, it probably has nothing to do with your appearance, it may simply be that they’re focused on other things and don’t want to be bothered. If this happens, just let it go and move on.

This advice is doubly important in digital spaces, where boundaries can be less clear. Unsolicited messages, excessive tagging, or repeatedly trying to engage someone who isn’t responsive crosses from networking into nuisance territory. Respect digital boundaries just as you would physical ones.

Reading the Virtual Room #

One of the hardest skills to develop in the digital age is understanding engagement levels without traditional cues. Here are some signals to watch for:

• Response time: Consistently delayed responses may indicate low interest
• Response length: Short, perfunctory replies often signal disengagement
• Reciprocity: Are they asking questions back or just answering yours?
• Enthusiasm indicators: Use of exclamation points, emojis, or GIFs can signal engagement
• Follow-up initiatives: Do they ever initiate conversations or only respond?

Practice, Practice, Practice #

I’ve already said it, but I’ll repeat myself by closing on this note: like anything in life, you’ll get better the more you practice. Get out, meet new people, and just talk to them.

Most of this is still the same online as it is in person. Pay attention, be curious, don’t make everything about yourself, and give people a reason to want to talk to you again.