9 fresh ways to start a conversation with anyone at work

You can be extroverted or introverted or somewhere in the middle, but no matter where you fall on the personality spectrum, there’ll be times when conversation doesn’t come easy. Overthinking it will generally get you nowhere, but not having a plan of action or a back pocket full of topics regardless of who you’re talking to also won’t help your communication game. If you’ve ever gone way out of your way to avoid an impromptu chat, fumbled with what to say, or defaulted to the weather (again!), the following guidelines should help.

And yes, while “guidelines” is a scary word, I promise that none of them require you to be agenius small-talker, the world’s most charming person, or outgoing at all.

So read on for advice on how to talk your way through any situation you’re likely to encounter along your career path, whether that’s in your own office, at a networking event, or at your company’s happy hour. Spoiler: At their core, they all have you being the initiator because, at the end of the day, simply being comfortable starting a conversation is half the battle.

1. With the founder or CEO

You: “Hi! How’s your week going?”

CEO: “Not bad. Busy! How about yours?”

You: “It’s going well. I’m excited to be working on [whatever project feels most significant to you].”

In this scenario, you give the leader a chance to share information with you. The open-ended question can lead to the CEO talking excitedly (in which case, plan to eagerly listen and ask a thoughtful question when he’s done), or it can result in him or her politely asking you how your work week is going. Be prepared with an astute but straightforward answer. Mention an item you’re working on and for what department if there’s any question as to your role at the company.

With big organizations, there’s nothing wrong with giving the founder or owner a break by dropping in any relevant info that’ll help him place you, which brings me to my next point: If you think he doesn’t know your name, now’s the time to extend your hand and say, “I’m not certain we’ve formally met. I’m [Your Name].”

2. With the newbie

You: “Hi. You started [this week, last Friday], right? My name is [Your Name] and I’m a part of the [X] team. Are you starting to feel settled? Have you been to [popular coffee shop in area] yet?”

Newbie: “Good, thanks. There’s a lot to learn, but I’m really enjoying it. How long have you been here?”

You: “I started in [whenever you started], and I can’t believe [insert something memorable here about your time at the company].”

Your goal is to get the conversation rolling and put the new person at ease. Sure, you could avoid making eye contact and simply go about getting your coffee in the kitchen, uttering a barely audible, “Hi,” but you can do better than that, and it pays to be friendly to your co-workers.

Remember, it’s not easy being the new kid on the block. If you value your company and your role, you should also make a point to appreciate its growth and culture — and that starts with you not ignoring someone in hopes your colleagues will shoulder the responsibility of befriending him or her.

3. With the (intimidating) colleague who’s been there forever

You: “Hey, I’m looking for recommendations for places to go for a networking lunch this week. I haven’t gotten to know the neighborhood well, but I thought, as someone who seems to know the ins and outs around here, you might have some suggestions.”

Colleague: “What kind of place are you looking for?”

This conversation opens up so many doors and avenues for discussion. Again, it’s one of those situations where you definitely don’t have to strike up a chat, but if the person is one you’ve been generally fearful of engaging with, getting over that intimidation is reason enough to say more than, “Hi. How are you?”

It’s not ill-advised to bring up a work-related topic, though that’s probably going to be easier if you’ve got some inkling of what the person does and what she’s working on. Appealing to her sense of expertise (in this example, knowledge of the area) is a smart point of entry. It’s likely that she’s a perfectly nice person, and your assumptions were incorrect — but there’s only one way to find out, and that’s bravely beginning the exchange.

4. With an event organizer

You: “This space is great. Thanks so much for organizing it. Do you plan things like this often?”

Organizer: “You know, I do because in my office…”

You’ve heard that most people like to talk about themselves, right? Trust in the truth of that and use it to your advantage. This is an especially handy tip if you have no idea what to say to someone you’ve just met or if you’re worried that you don’t have anything interesting to contribute and are grasping for language.

Placing the conversation lead on an event organizer is rarely going to backfire, and the bonus is that if you get the person talking about himself, you might even find that you can interject here or there, ultimately making a strong impression and adding something to the conversation.

5. With any VIP

You: “Hi. My name is [Your Name]. I know you’ve probably got to make the rounds, but I didn’t want to regret not coming over and introducing myself — and letting you know that your app is genius.”

You might not get much more than a thank you out of the very important person, and if that’s the case, don’t take it personally. But, a compliment will often ignite a discussion, and if you truly do have something kind to say about the person’s company, program, or product, why not open with that and see where it goes.

6. With your former boss

You: “It’s so good to see you! How is everything over at [Company Name]? I read that they’re expanding [department or product]. You must be excited to be spearheading that.”

Ex-boss: “As a matter of fact, I am. It’s been pretty chaotic, but it’s a fun time to be busy, and I’m happy to have something to focus so keenly on…”

No matter what terms you ended on, you don’t want to pretend like you didn’t see your former manager over there by the cheese table. By approaching her with a pleasantry and more, you demonstrate class and character. This isn’t the first occasion you’re going to run into someone you’re not dying to talk to, but it’s like they say, practice makes perfect.

And even if your former manager is harboring negative feelings on your departure, she’ll probably have a hard time rebuffing your kindness.

7. With the person from the department you know nothing about

You: “How’s your week going? Busy with projects?”

Person: “Busier than usual because we’ve got [names major initiative the team is focused on].”

You: “Oh, interesting. I hadn’t thought how that might affect your team. What are you working on specifically?”

By being vague in your opening, you allow for the fact that you don’t know exactly what the person does (don’t worry, he probably doesn’t know too much about your day-to-day either), but you, nonetheless, make an effort to engage him in a conversation about his work and his team and department.

If he’s a chatty person, maybe he’ll end up painting a clear picture of his role and the projects his team is working on and you’ll have material for every subsequent meeting. Or, if he’s more reserved, you can jump in and start talking about an initiative your department is focusing on.

8. With the boss’ significant other

You: “It’s so nice that you were able to make it tonight. It’s always fun to meet the people we hear so much about. Susan has mentioned that you both like to cook together. What’s the best thing you’ve ever made?”

The S.O.: “That’s a tough one. Maybe my chicken under a brick dish…”

This starter assumes you have some recollection of something your boss has said about her significant other. If you can’t remember a darn thing, you can default to the modern, more popular way of asking what she does: “What did we tear you away from this evening?” Or: “What cool stuff have you got going on this week (besides this gathering!)?”

With your manager’s partner, you don’t want to get too cozy and assume a familiarity that doesn’t exist, but you also don’t want to view the guest as off-limits. Just as you’re refusing to let yourself be intimidated (for long) by the seemingly aloof colleague, you’ll also want to avoid acting nervous. If you and your supervisor already have a good working relationship, making an effort with the S.O. is only going to further that.

9. With the intern

You: “How was your weekend? Are you watching or reading anything really great at the moment?”

Intern: “It was great. Actually, I’m totally hooked on both [Netflix series] and [NBC series]. Do you watch either of them?”

You: “I’ve heard great things about [Netflix series], but I haven’t had a chance to start it yet. I’m with you on [NBC series]. I love the actor who plays the dad.”

Once you start a dialogue about entertainment — TV, books, movies — it’s unlikely that you’ll struggle with finding more to discuss. Unless the intern lives in a cave and has no awareness of what’s going on around him, chances are, you’ll land on at least one item of shared interest, or even something you totally disagree on. You love The Americans, and he prefers House of Cards? Have at it. Nothing like a good spirited debate to carry the conversation beyond the basic, “How was your weekend?” “Good. How was yours?”

Of course, the scenarios depicted here are, in part, pure speculation. It’s nearly impossible to know how the person on the receiving end of the conversation you start is going to respond. But, that’s not what matters. If you can master the approach and the initiation, you’ll sail through the rest of it almost always. Be yourself, be sincere, and accept that starting and carrying on amiable conversations takes a certain amount of effort for most people.

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