How to Talk to Pretty Much Anyone About Pretty Much Anything

Edith Wharton once said, “Ah, good conversation -- there’s nothing like it, is there? The air of ideas is the only air worth breathing.”

Ms. Wharton had a way with words (written and otherwise), but she would likely be horrified to know that most of our daily conversations nowadays start with shorthand texts or three-line emails.

And yet, in spite of the proliferation of texting and emailing in modern conversations, you still have to know how to strike up a conversation to get a raise, build your network, ask someone out, or provide someone with feedback. It's as important now as it ever was to know how to break the ice, get to the point, make a connection, and frame a request.

But it's hard. That's why we put together this handy guide on talking to anyone about anything. We hope these tips help you navigate everything from cocktail parties to conference rooms with the greatest of ease.

Ask better questions to get better answers.

If you ask yes or no questions, you’ll get yes or no answers. Most of us are conditioned to ask and respond to the same questions at every cocktail party we attend -- so do everyone a favor and leave the “what do you do for work” as a first question at home.

Asking more interesting questions gets you undeniably better answers. So instead of probing on what someone does now (which typically leads to awkward humble bragging), ask what they wanted to be when they grew up, what their first concert was, what magazines they subscribe to, or which celebrity they’d want to invite over for dinner. Doing so relieves people of the boring back-and-forth of typical office party conversation and into far more interesting territory.

The same rule applies to business settings. I’ve never once hired someone who didn’t have solid questions for me about the market we compete in, the team he or she would be working on, and the company work environment. Whether you’re networking for your next career move, interviewing for a job, or meeting with a potential new vendor or partner, your goal should be to ask questions that can’t be answered with a quick Google search. I’ve included some examples below:

On Competition

Good: Who does your company compete with?

Better: I noticed that one of your competitors recently released X feature. How do you think that will change your competitive strategy moving forward?

Best: Many people view your competition as Y and Z, but I really think long-term that Company A could be a threat, given that you’re both converging toward the ecommerce space. How do you think about your long-term competitive strategy as it relates to Company A?

On a Specific Role

Good: What does this role entail?

Better: I know this role entails a significant amount of customer interaction. Can you tell me a little bit about how much of the expectation is around customer service versus upsells?

Best: I read on Glassdoor that people in this role are expected to deliver roughly 30% of all upsells. What is the training process like to deliver this, and how does your comp structure reward over-performance on that goal, if at all?

On Work Environment

Good: What’s it like to work here?

Better: Your company has recently doubled in size, and I’ve read a lot about your commitment to flexibility and autonomy. Has that changed at all over the last year?

Best: Recently, one of your tech leads wrote a blog about how engineers ship code during their first week on the job here. How does that same principle of autonomy apply on teams outside engineering?

Just as you wouldn’t show up at someone’s home for a party empty-handed, don’t show up to a networking event, meeting, social event, or dinner without some thoughtful questions for your counterparts. The best conversations start with better questions, so do your homework. Anyone can do a quick Google search; go a level deeper to inspire more thoughtful and engaging conversations.

Leave the weather outside.

It seems that regardless of context, the ultimate conversation-filler is to talk about the weather. On the surface, that seems fine ... but do you know anyone who actually enjoys talking about the weather other than Al Roker? Didn’t think so.

Weather is the fastest way to end a good dialogue, so leave the weather outside (regardless of how frightful it is) and work on other ways to fill awkward gaps in conversation. Unless you’re a meteorologist, the chances that you or anyone else has something truly interesting to say about the weather is extremely small.

To avoid weather talk, check out TheSkimm, your Twitter feed, or other news sources to find at least two topics more interesting to talk about than precipitation before you arrive at your next event.

Find yourself stuck in a vortex of weather-talk already? (Sadly, this is an all-too-common occurrence in New England this year.) To get out, switch gears to something more interesting by asking who in the group has a forthcoming vacation plan to escape the weather. Regardless of whether they are heading North, South, East, or West, talking about people’s vacations is infinitely more interesting than just talking about the forecast. Plus you might get some good travel recommendations out of it.

Want to change the subject altogether? Ask everyone in the group which website they visit first when they get up in the morning. Doing so reveals a lot about their personality without being overly revealing -- and whether it’s CNN, Reddit, TechCrunch, US Weekly, or ESPN.com, it helps you understand what your new friends are most passionate about without violating their privacy or confidence. That’s a heck of a lot more fun than playing group meteorologist.

Master the Bridget Jones introduction.

In Helen Fielding’s Bridget Jones' Diary, the book’s heroine (Bridget) is a woefully poor conversationalist who makes a resolution to introduce people with thoughtful details. While she may not be a fountain of wisdom for dating advice, her counsel on introductions is extremely wise. Instead of thinking of introductions (of yourself or others) as transactions to be completed -- “Jill, meet Brad, Brad, meet Jill" -- think of them as conversation starters.

For example, my colleague Lia works on our product marketing team, and I could easily introduce her to someone else accordingly. But for people who don’t work at HubSpot or in marketing, that type of introduction doesn’t help spark a good conversation. Instead, I typically introduce Lia as having been to nineteen Justin Timberlake concerts in the past year. Doing so inspires reactions from JT fans and haters alike, and it also tees up Lia to tell stories about her travels -- a much more interesting topic than how long each person in the conversation has been at their respective companies.

In addition to the quality of your introductions, make it easy for new people to enter the conversation. If you don’t know someone by name, give them a chance to jump in based on the topic with something like, “We were just discussing the very serious topic of which restaurant in town has the best margaritas. Do you have a strong vote on the matter?” Making people feel included from the start makes everyone feel more at east, prevents awkward “should I or shouldn’t I” introductions, and ultimately makes it easy for people to come and go seamlessly.

Improv-ise.

Tina Fey’s book Bossypants outlines some cardinal rules of improvisational comedy, one of which is mastering the “yes, and” principle. Let me give you an example: Let's say your improv partner states a fact, like “the police are here." It’s your role as their improv partner to respond first by acknowledging the truth of what he or she is saying, and then by adding to it. Something like, “Yes, and who knew they’d bring tanks with them, too?”

Responses like this build the storyline for an improv audience -- and they have a similar impact on real-life conversations. So the next time someone says, “Did you see the movie Wild?”, don’t respond with a simple “yes." Follow the queen of comedy, Tina Fey, and offer up something else: “I sure did, and I liked it better than Into the Woods. Do you think Reese Witherspoon will get the Oscar?” Alternatively, if someone asks if you saw the Super Bowl, don’t just nod or shake your head. Give them some direction, either with an “I did, and as a Pats fan, I’ve never been so grateful the Hawks decided to throw. Can you believe it?” Or if the game wasn’t your thing, say, “Of course -- I already have my left shark costume for Halloween next year. What are you going to dress up as?" "Yes, and" is a formula for significantly better comedy and conversation, so do the math and plan accordingly.

Be warned, though: “Yes, and” can quickly become a vehicle to talk more about yourself -- but the trick is to do exactly the opposite. Listening is as important as talking, so instead of trying to “one-up” the people you’re chatting with, it forces you to think deliberately about adding value to the conversation and acknowledge their input. Furthermore, thinking about conversations as mini improv sessions also forces you to take more risks. Tina’s wisdom rings true here again: “You can’t be that kid standing at the top of the waterslide, overthinking it. You have to go down the chute.”

This trope is as true of conversations as it is for other risks in your life: No matter how extroverted you are or how many people you know in a room, everyone still gets nervous in first-day-of-school situations, whether they are personally- or professionally-oriented. So instead of watching people pass and wishing you had spoken up, take a risk, pick a new improv partner, and practice your very best “yes, and” skills. The absolute worst that can happen is thirty seconds of awkward conversation (which, let's be honest, probably would've happened anyway).

Learn to be a play-caller.

In football, the coaches who call the plays are responsible for reading what’s happening in the game and then calling the best play possible for their team given the scenario. They have some set plays they know their players can execute on, and the team (and other coaches) look to them for exactly what to do when time is tight and the stakes are high.

The best conversationalists become de facto play-callers in conversations: They help bail people out of awkward situations; they know how to switch gears when the chatter takes a turn that is too serious or too personal; they include people in the conversation who may have otherwise been left out of the conversation.

The most important step in becoming a play-caller is recognizing that it’s not about talking more. In fact, if you’re an effective play caller, you might make someone else the star of the show. Instead, becoming a good play-caller means reading a situation well, listening actively, and knowing how to put the spotlight on others without putting them on the spot.

Not sure where to start? Try giving someone a genuine and thoughtful compliment. If you’re in someone’s home, don’t just say “I love your house.” Instead, choose a single item you really like and ask them to tell you the story behind it. This invites them to share more than just a polite “thanks so much” and often leads to a travel narrative or anecdote that others in the group can relate and add to.

Self-deprecating humor also works wonders in a play-calling setting. For example, I’ll often offer, “Has anyone else already completely botched their New Year’s resolution already? I know I have, and it’s only going to get worse tonight!” When people are uncomfortable, one-upsmanship has a funny way of working its way into the conversation -- so making fun of yourself makes everything significantly sillier and invites others into the conversation, instead of making them feel like they need to boast or promote themselves.

Focus on the positive.

If people wanted to join the debate team, they’d go back to high school. When cocktail parties turn into debates, the only "winners" are the bartenders-- because everyone just drinks heavily and goes home earlier. So even if you’re stuck talking to the world’s biggest party pooper, try to find the silver lining. Then everyone will feel more at ease.

This is not to say you need to agree with jerks for the sake of polite conversation. If someone offers a rude version of a differing political opinion in a professional setting, I’ll typically try to change the subject by saying, “Given that debate's been going on for decades, it doesn’t seem like one we’ll reconcile tonight, so let’s focus on a more pressing issue in front of us: where we locate more of those appetizers they had on our way in.”

Even more tragic than overly politicized conversations are those that put people on the spot. For example, let's say you’re in a group networking setting and someone remarks, “Gosh, you’re still single? I had no idea," or makes an off-putting remark about someone’s appearance, health, or awkward family situation. As a general rule, make it your goal to have everyone leave a conversation you’re in happier or more relaxed than they were when it started.

If someone is put on the spot, take an active role in helping them out: Change the subject, crack a joke at your own expense, or offer them a compliment that changes the course of the conversation. That kind of karma comes back to you in spades.

Don't try to ask all things of all people.

Let’s face it: It's hard to ask for a job, for money for your startup, or for advice to help accelerate your career. But in order to avert the awkwardness and potential rejection of a one-on-one email or conversation, far too many people try to be all things to all people -- asking dozens of people for input, advice, or opportunity. You’re far better off investing time and energy up front to identify a small group of people, investors, or companies where there is mutual potential value and follow with a thoughtful ask and conversation.

Arlyn Davich, the founder of New York-based startup PayPerks, notes, “The best kind of investors are those whose expertise you value more than their money. Once you’ve identified who those people are, be specific as to what they are uniquely qualified to help you with.” So instead of asking your entire LinkedIn network for job advice, or everyone you’ve ever met to invest in your business, identify a small cadre of people who can truly impact your decision or influence your success in your industry.

Don’t beat around the bush if you have a clear, concise ask for someone. Just make sure you find an appropriate setting to introduce yourself. (Mid-meal with their family doesn’t count, nor does when they are on a conference call). Provide a brief introduction of your background or company, and clarify where you think they can most help and why. Be polite, avoid presumption, and be prompt in your follow-up -- should they agree to help you out. Above all else, make it easy for others to help you. If they agree to chat, then travel to them, show up on time, and be absurdly and ridiculously prepared when you go.

I had a friend in college who loved to kick off group conversations by asking how much a polar bear weighed. After some quizzical looks (and the odd guess or too, usually from an engineer or scientist), he would deliver the punch line (“enough to break the ice”) just in time for some awkward laughs and to get a conversation started. While his joke was horribly cheesy (and occasionally bombed), it’s proof that everyone is a little awkward and uncomfortable in conversations with people they don’t know.

All right, folks. The next time you’re entering a networking event, showing up for your first day at a new job, arriving at an interview, or attending a housewarming party, you can arrive armed with the tips above. Here's another important insight from another woman I greatly admire: Amy Poehler once said, “There’s power in looking silly and not caring that you do.”

So take a risk, strike up a conversation with someone you don’t know, and ask an unconventional question. The worst thing that can happen is that it doesn’t work and you end up talking about the weather -- and that was likely going to happen anyway.