Entering and Exiting Conversations with Grace

Raise your hand if you’ve ever been thrown into one of the following scenarios. You walk into a full room at a conference social and don’t see a single familiar face. Or, after your first week on the job, you’re at the company picnic and don’t know anyone you’re sitting with. Or this: you’ve popped into a virtual meeting just as the organizer randomly assigns everyone to a breakout room.

Nervous doesn’t come close to describing how you feel. It’s more like alarmed, panicked or frozen in your tracks! Striking up conversations with strangers or large groups is never easy — it takes time to gain the necessary skills. Such skills also help you to gracefully exit the same conversation. Here are essential tips to help boost your effectiveness.

For entering or exiting a group, like the one at the conference social hour:

1. Small group, targeted entry. Stand in the outskirts of the circle formed by the group. Make eye contact with the speaker, follow the content of the conversation and wait for a pause in the flow of the conversation. At an opportune time, such as a pause or comment from someone other than the speaker, make a relevant comment about what the group is discussing and quickly introduce yourself. “The statistics you mentioned are astounding. Hello, my name is Tatiana”

2. Small group, stealth entry. This requires bolder behavior, so I encourage you to first test it with trusted colleagues. Observe a group conversation from the outer circle and, when you sense a break in the conversations, move closer and make your introduction. Using your biggest smile and confident posture, say: “Hi everyone, my name is Tatiana. This is my first conference. Mind if I join you?” At this point, don’t add anything further. Instead, acknowledge affirming nods and greetings to you, and use this opportunity to enter the stream of the conversation. Don’t feel obligated to speak immediately.

3. Listen with your whole body. If your plan is to ‘collect conversation data’ so you can make comments later, be sure you’re listening at 110% capacity. That means using affirming non-verbals. Use eye contact that tracks whomever is speaking and tie to positive affirmations such as nodding and smiling, and statements such as “I see” or “I hear you.”

4. Exit strategically. Settings like a conference allow using one of the three “Goodbye Bs.” Bathroom is the easiest, or you could exit to the Bar for a glass of water or wine, or even Bail out to another group if someone’s expecting you, or if you’ve promised to make an introduction.

As another option, you might simply state: “You’ve been so generous with your time, I should allow others to benefit” or “Thank you so much, I know that other people have things to ask you.”

For navigating entry and exit in a virtual group setting:

1. Establish common ground. Here are two easy openers for use in a breakout room where you likely won’t know anyone or anything about them. “Where is everyone from?” and “Let’s introduce ourselves and our industries; I’ll start...”

2. Replace silence with open-ended questions. Unlike entering a live, in-person group where the conversation flows easier, you might demonstrate being attuned by asking follow-up questions. Be careful not to rely on this strategy entirely and coming across as too dominating.

3. Note themes for follow-up. Every breakout group ends up focusing on some type of discussion topic. Focus on this and use it to direct your follow-up (via email or LinkedIn direct message). And remember to make the effort and connect with new acquaintances you’ve met in breakout groups.

4. Note exit countdown. Breakout groups often end abruptly, so be sure you make a graceful farewell before you are cut off without warning.

Winning formula for entering a single conversation with a stranger:

I’ve created a formula in my “Starting a Memorable Conversation” LinkedIn Learning course which has three simple steps: Read, Comment, and Engage.

READ Be aware of the environment around you. Sadly, most people do just the opposite: they’re absorbed with their phones and oblivious of what’s happening around them. The best way to gain an impression in a new setting is by quiet and careful observation.

Intense focus on the external environment is a prerequisite for doing a quick read of the person you want to connect with. If you’re sitting next to someone in a coffee shop who’s intently typing away, using a newspaper to shield themselves, or scribbling obsessively on a note pad, they probably don’t want to be interrupted. But if they pause or make eye contact, that’s your opportunity for a greeting — a “how is it going?” or simple “hello” delivered with a big smile.

COMMENT Being attuned also helps you collect information for use in your conversation starters. For example, say something specific about the weather or the setting. If the person is someone important or famous who doesn’t know you, make a context-specific comment that would not embarrass you.

In the busy shop, it’s better to say “I’ve never seen such a long line here for the morning caffeine fix” vs. “Wow, you’re on our company board! It’s such a thrill to meet you!” The higher the level of celebrity or notoriety that a person has, the more important it is to forge a common connection.

ENGAGE After making a comment based on your read of the environment, you can then try posing an open-ended question. If done correctly, it can initiate a mutual exchange of information and begin to build rapport. Remember that people like talking about themselves. A simple inquiry such as “Do you fly through here often?” works for an airport chat. “Where is home?” is another open-ended question about travel, or simply “Is this a long layover for you?” can be an appropriate start to a conversation with someone you don’t know.

Here’s a video clip from the “Starting a Memorable Conversation” course of a new hire approaching the CEO at the company picnic. See if you can spot the cameo appearance.

Entering and exiting conversations gracefully requires finesse, mindfulness, and skill. Whether you’re navigating a crowded conference room or a virtual breakout session, remember: read the room, engage authentically, and exit with grace. Keep conversing confidently!

Check out the link for free access to the Starting a Memorable Conversation course in the comments section. The Exercise Files are particularly helpful if you’re looking to build this skill.

As always, I appreciate you reading Stronger. Follow me on LinkedIn and be sure to send this newsletter to a friend you think might benefit.