(Illustrations: Elliott Salazar)

Thanks to Susan Cain — author of Quiet and founder of the online organization The Quiet Revolution — nearly everyone is familiar with the terms “introvert” and “extrovert.” (And if you’re not sure where you fall on the spectrum, you can take a quiz on Cain’s site.) Despite the hype introverts have gained over the past few years, Cain’s writing hasn’t fundamentally changed the fact that our modern workplace isn’t always accommodating of them.

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All offices are different, but there are a few things most people have to deal with at work on the regular —whether it’s asking your boss for something (from time off to a raise) or handling conflict with a coworker. We talked with two experts about how to handle these more difficult conversations. Jennifer Kahnweiler is a certified speaking professional who works with introverts and has authored several books on the topic, including The Genius of Opposites: How Introverts and Extroverts Achieve Extraordinary Results Together, to be released this August. Jill Isenstadt is the head of coaching at Joyable, an app that provides evidence-based mental health resources for people with social anxiety.

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Whether you identify as an introvert or are just trying to figure out how to handle some difficult workplace conversations, Isenstadt and Kahnweiler have great tips for getting through the most awkward moments. Having these chats might not get any easier, but at least you’ll have the proper tools to prepare yourself for them.

You’re in an meeting or on a conference call full of important people — managers and clients. Everyone talks loudly, and a few key players dominate the conversation. You feel a bit stumped as to how to get a word in edgewise or how to make sure your ideas are heard.

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Focus on your strengths as an introvert and arrive to the meeting early so you can engage in some rapport-building before everything gets started, Kahnweiler says.

“What you realize is that there’s a meeting before the meeting, and a meeting after the meeting. Whether you’re heard or not during a meeting is based on people knowing you. And the times before and after a meeting are the best times to create those deep relationships introverts are known for,“ she explains.

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Kahnweiler also recommends speaking up within the first five minutes of a meeting. "Otherwise, you get very anxious if everyone’s already spoken,” she says.

Being prepared is crucial, she argues: “People who are very effective work to leverage preparation and have agendas for the meeting, especially if it’s full of Type A personalities.”

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When it comes to handling interruptions from your coworkers, Kahnweiler suggests putting your hand up, “like a talk show personality,” to indicate you’re not finished. Sounds a little silly, but imagine channeling Jon Stewart when he’s facing down Bill O'Reilly. A simple gesture can have a lot of power, especially from an introvert who isn’t inclined to speak too often.

“Introverts are also really respected because they don’t talk too much,“ Kahnweiler notes. "They don’t need to say a lot to really nail their point.”

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In turn, Isenstadt recommends identifying exactly what you’re worried about during the meeting. “Are you afraid of stumbling over your words or saying the wrong thing?” Think back to past successes and remember that you are capable of interacting in these settings. Anxious people have the same social skills as people without anxiety — they just might have less confidence or experience. “Remember that you know the information well and can contribute,” she says. “To take some steps to feel more comfortable, try speaking in lower-pressure situations, like smaller groups, or talking to colleagues one-on-one.”

Your coworker has done something frustrating and disruptive to your workload, your work environment, or your relationship as a whole. You’re upset, but you don’t know what to do — or maybe your coworker is upset at you, and you’re sorry, but you feel nervous about trying to move forward. How do you defuse an uncomfortable situation with someone you have to see every day?

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“First, you should remember that conflict is normal and necessary,” says Kahnweiler. “If you’re not having conflict, you’re not talking about what’s real. It’s a question of understanding what your and the other person’s preferences are. Introverts need time to digest information and are better at writing, while extroverts have to talk out their thoughts and differences.” It’s best to think about what your ultimate goal is in order to solve the conflict. Also, having a discussion will prevent either of you from spending way too much energy on the conflict.

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“If you’re in a tense situation, I recommend taking time to talk with that colleague, and coming to that conversation with an idea that there are multiple views on any situation,” says Isenstadt. “Be direct: ‘Here’s my perspective; what’s yours?’ They’ll appreciate that — it’s better than trying to avoid it.”

It won’t be easy, but it will be worthwhile. It’s also worth remembering that introverts excel at conflict resolution. While that initial conversation might be difficult, focus on your strengths — considering other people’s feelings, developing new ideas, seeking solutions — and use those to your advantage.

You’ve been invited to an event (it could be work-related, a networking opportunity, or even a friend’s party), but you hardly know anyone there. How do you manage the daunting task of talking to random strangers?

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“Again, I think for introverts, pulling out their preparation is the key,” says Kahnweiler. She recommends having a list of topics to discuss, whether you’re sharing info (a new app you like) or asking for advice (where to go on a trip). It might seem odd to prep for such mundane conversations, but it can be super helpful. "When you have some talking points, you can just start up a conversation, so you’re not just talking about the weather,” she explains.

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Kahnweiler recommends doing research beforehand if it’s a work or business event. “It’s an effort that pays off. If you think, why [am I] going to this event?…you’ll have a goal in mind and a specific lens on.”

“You might think, I’ll say something stupid, or I don’t know what to say, but again, it’s about challenging yourself with evidence,” says Isenstadt. “There’s likely a reason that you’re here; you have the means or information to be here, and other people are probably feeling the same thing.”

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The worst outcome, she implores us to remember, is someone walks away when you talk to him or her. “Practice the scenario in your daily life so you feel more comfortable. Try speaking briefly to people on the bus or train, or even a cashier or a senior colleague. These are people who might give you a bit of anxiety to talk to, but speaking to them will help you feel more prepared for going to networking events.”

Isenstadt also emphasizes creating space for helpful thoughts — and that anticipation is often more anxiety-inducing than the actual actions. “It’s helpful for our clients to think, I just have to say hello.” That initial part is the challenging moment, but you just need to introduce yourself.

You want to speak to your boss to ask for a raise, or special training, or even to help with a conflict or complaint. Depending on your relationship with your manager, it can be difficult to have these high-stakes conversations.

Think of your request from your boss’s perspective, Kahnweiler says. “This takes homework. When you’re asking for a raise, frame it as a statement of what you’ve done and how you’re going to build on that, and support your boss and their goals.” She recommends thinking about numbers you can bring in, since bosses love results.

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“Showing how you’re going to get your results demonstrates that you’re not just thinking about yourself, but about the whole organization. Like, ‘You investing in me learning this language makes sense for our company becoming more global.’” Kahnweiler also recommends prepping your manager with an email before the meeting and following up with a summary email.

Meanwhile, Isenstadt says to focus again on helpful thoughts to challenge more anxious ones. “If you’re afraid of stumbling or stuttering, remember: You’ve done that before in front of your boss, and you can cope. If you’re fearful of them saying no, think more about why what you’re offering is so compelling.”

She also recommends practicing these discussions in low-pressure situations (like asking for help in a store) before interacting with your boss. Having successes in everyday situations that are a little uncomfortable or awkward can help you prepare for the tougher ones. “It’s common to feel anxious in these situations,” Isenstadt adds, “but you must remember that you have the social skills to do this.”

By Sulagna Misra

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