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:
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.