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Communication Strategies

15 Ways to Command a Conversation Like a Boss

If you're the one talking, it's your responsibility to make sure others are listening.
15 Ways to Command a Conversation Like a Boss
Image credit: Maskot | Getty Images
Entrepreneur Staff
11 min read

Conversations can elicit a range of emotions. They may be daunting, or they may be dreaded. They may be awkward, or they may be monotonous. The good news is, you, as a participant in any conversation, have more control than you think about whether these emotions overtake the dialogue.

Having a successful conversation is about striking the balance between preparedness and flexibility, between explaining your thoughts clearly and knowing when to pause or check in. It’s about being upfront about your preferences and ideas while being open to adapting them based on what comes of the discussion.

Related: Use These 10 Words in Conversation to Get What You Want

A fruitful conversation stems from establishing a rapport with someone. Show them you know where they’re coming from. Clarify that you understand what they’ve said. Be respectful of their time and don’t dictate back to them how you perceive them to be thinking or feeling. Keep questions open-ended. Experiment with new conversation settings or styles. And don’t give in to the internal voices that try to convince you to defer too much or suffer in silence.

To help you get your points across and help others convey theirs, read through the following 15 tips, which expand more on the ideas above.

Related video: 2 Tips for How to Communicate With C-Suite Executives

15 Ways to Command a Conversation Like a Boss

Study up beforehand.

Avoid wasting anyone’s time by getting to know your audience, advises Stacey Hanke, speaking coach and author of Influence Redefined.

If there’s lead time before your conversation, whether or not you already know the person you’ll be speaking with, try to get a better understanding of where they stand. What is their level of knowledge, not to mention their opinion, about the topic you’re preparing to discuss?

Always be mindful of the value the other person can gain from the conversation, in addition to the value you can gain.

Also, if you have an idea of how much time you’ll have with the person, plan accordingly. If your time is limited, prepare to deliver the points you need to get across quickly and succinctly.

15 Ways to Command a Conversation Like a Boss

Don’t be afraid to pivot.

Just because you planned what points you wanted to cover ahead of time doesn’t mean you should be rigid about getting through all of them. You might find, once the conversation is underway, that it’s going in a different direction.

In that moment, you can evaluate whether it’s beneficial for it to flow naturally. This change in course might be a great opportunity to accomplish something even greater than planned with the conversation. If you think you’re getting off topic to an unproductive degree, then you should feel empowered to steer the chat back to the matter that prompted it.

Speak extemporaneously. Even if you cover everything you meant to cover, you might do so in a roundabout, organic way vs. by checking points off a list.

15 Ways to Command a Conversation Like a Boss

Don’t talk over someone who interrupts you.

If you’re both talking, neither of you will be able to hear the other. Let that person finish, but don’t become discouraged or let them dominate the discussion, Hanke says.

Related: Why It's on You to Stop People From Interrupting You

Listen to what they have to say and think about what prompted them to say it. Doing so could give you insight into what additional information they might be seeking that you may not have considered. Once you know more about what their interests are, you might adapt your remarks so that they’re more relevant.

15 Ways to Command a Conversation Like a Boss

Pause often, at natural intervals.

Some people think pausing is awkward or makes them seem less confident. In reality, Hanke says, it separates the points you're making, so that they are easier for your listener to digest.

Pausing is especially important when you are explaining something complicated or technical, to give your audience a chance to keep up.

On that note, taking time to pause now and then gives you a chance to keep up with yourself. You can be more deliberate with your words if you take a second or two to think about what you’re saying. You can also scan the body language of those you’re speaking with, see whether they’re engaged, confused or distracted and change the content or tone of your remarks accordingly -- or ask your audience if they need clarification.

15 Ways to Command a Conversation Like a Boss

Be direct and assertive.

Culturally, women are more likely than men to qualify their remarks, ask for permission to speak, defer to more dominant voices and apologize for contributing their thoughts. But anyone can act in this manner, and it’s not the most effective way to get a point across.

If you’re tempted to couch or equivocate, recognize that aggressiveness and assertiveness are two different things, and that being direct is an affront far less often than you might think. In many cases, your listener will respect you more for it.

On a similar note, avoid telling someone, “I don’t care” or “It’s up to you.” Show that you’re engaged with the conversation and that you acknowledge the person you’re speaking with values your opinion by saying something such as, “I don't feel strongly about either course of action, but here are some factors to take into account.”

15 Ways to Command a Conversation Like a Boss

Don’t be afraid to say no.

This goes along with being assertive. Especially in a professional context, you may fear that disagreement could prompt conflict. In reality, if you don’t stand your ground, the consequences could be harmful to your business.

Don’t say yes or agree just because it’s the polite thing to do. You can politely say no, especially if you offer an alternative option or idea.

15 Ways to Command a Conversation Like a Boss

Help the other person help the conversation.

If someone is rambling, or if someone is interrupting often, call them out -- but politely and calmly. They might not even realize they’re speaking in a way that is hindering the dialogue, Hanke says.

Say things such as, “Did you just hear that? You just packed a lot of ideas into one paragraph,” or, “I’d like to finish this thought quickly, but I’d love to hear what you have to say in just a moment.”

You can also ask your listener questions to make sure they’re understanding what you’re saying, Hanke suggests. “What are your thoughts on the last couple of points we covered?” or “You’ve got some expertise in this area. What are your thoughts?”

Consulting another person will make them feel valued, which in turn will help you build their trust and lend more credibility to what you’re saying.

15 Ways to Command a Conversation Like a Boss

Make eye contact.

Everyone knows this one, but they don’t always do it, because it can be uncomfortable. Locking eyes with someone is intimate, but that’s exactly why it’s so powerful. It builds trust to look someone in the eye while completing an entire thought, and it makes you seem more sincere.

Plus, if you’re looking directly at your listener, you’ll be able to gauge how they’re perceiving what you’re saying and you can adjust or clarify.

15 Ways to Command a Conversation Like a Boss

Summarize and reiterate key points.

People tend to overestimate how well people understand what they are saying. The “tappers and listeners” study out of Stanford University illustrated this well. Participants tapped a melody of a well-known song, and listeners had to guess the tune. While tappers thought listeners would have a 50 percent accuracy rate, they only guessed 2.5 percent of the songs correctly.

The same goes with speaking: Only you know exactly what you mean, so be as clear as possible. One way to do accomplish this might be to summarize your main points at the begin and the end of a discussion.
15 Ways to Command a Conversation Like a Boss

Establish expectations in a negotiation.

In a conversation that’s centered around a negotiation, such as for a salary or a flexible work schedule, enter into the conversation with clear parameters.

In the case of a salary negotiation, employers should start by establishing a range that they’re willing to work within. Meanwhile, employees or prospective hires should go in having done their research to predict what the employer typically offers at that level, if such information is available, explains Sally Klingel, the director of labor management relations at the Cornell University Scheinman Institute on Conflict Resolution.

The benefit of having a conversation in this setting, however, is that even if everyone has their mind made up from the get-go, the discussion can lead to better understanding. One party might ask the other what their criteria are for making a certain type of decision. If you don’t get what you’re looking for this time around, you can cater your future performance to those criteria and make a stronger case in the future.

15 Ways to Command a Conversation Like a Boss

Keep things fresh.

Studies have shown that you’ll get someone’s attention and help them remember what you said if you surprise them or include an element of novelty.

If you have routine conversations with someone, mix things up every once in a while. Don’t just hold talks in your office or in the same conference room every day. Go to a coffee shop. Structure the discussion in a new way. Make a (tasteful and setting-appropriate) joke. Whatever it takes to keep things interesting.

15 Ways to Command a Conversation Like a Boss

Don’t undermine the other person.

Saying something that demoralizes the person you’re speaking with, such as “You look tired,” will likely catch them off guard, if not offend them because you’ve implied they look disheveled.

If you’re genuinely concerned about someone’s well being, simply ask, “Is everything all right?” If the person wants to open up to you about how they’re feeling or something they’re going through, they will.

15 Ways to Command a Conversation Like a Boss

Confirm your assumptions.

A conversation is an opportunity to make sure you and the person you’re speaking with are on the same page. Even if body language -- nodding, eye contact and good posture -- makes it seem like you two have a common understanding, you might consider quickly clarifying.

Don’t part ways before doing this: Paraphrase the point you think the other person made and confirm with them whether you’ve correctly processed what they’ve said.

Another way to make sure you’re in alignment is to ask the other person relevant questions based on the topic at hand.

15 Ways to Command a Conversation Like a Boss

Steer the conversation toward your strengths.

If you’re part of a one-on-one or group conversation that’s transitioned into a topic that you know little about, don’t sit idly waiting for the gears to change. Think creatively about what you can contribute.

For example, you might not follow sports, but you may have heard about one of the players in a context outside of game stats -- perhaps a side hobby you’ve learned an athlete in that sport spends time on, one that you share.

Or maybe you’re not really into the British Royal Family, but one of your friends is, and something they learned from a project they did at work could be loosely applied in your organization. You could pipe in with something like that, and the conversation might flow from there back to your interests.

Changing this subject in this way is a lot smoother than simply saying something like, “Can we get back on track?” or “This isn’t what this conversation was supposed to be about.” Plus, people will respect you if what you interject teaches them something new and useful.

15 Ways to Command a Conversation Like a Boss

Silence your inferiority complex by asking the other person for advice.

During a conversation, it can be easy to get into your own head, distracted by the other person if they seem knowledgeable, more powerful or have your fate in their hands in some way. They might be a boss, a mentor, a peer you compare yourself to, an investor -- you name it.

Instead of feeling inferior and underestimating yourself, tap into that person’s experience and expertise while you have their ear. Ask them how they achieved their accomplishments. Even tell them you admire them. Chances are, they’ll respect your honesty, and flattery may get their attention.

You can add value, too. Tell them what you’ve been thinking, learning and doing lately. They’ll likely have something to learn from you, which will help level the playing field and make the dialogue more productive.

Add to Queue
  • 15 Ways to Command a Conversation Like a Boss
  • 1. Study up beforehand.
  • 2. Don’t be afraid to pivot.
  • 3. Don’t talk over someone who interrupts you.
  • 4. Pause often, at natural intervals.
  • 5. Be direct and assertive.
  • 6. Don’t be afraid to say no.
  • 7. Help the other person help the conversation.
  • 8. Make eye contact.
  • 9. Summarize and reiterate key points.
  • 10. Establish expectations in a negotiation.
  • 11. Keep things fresh.
  • 12. Don’t undermine the other person.
  • 13. Confirm your assumptions.
  • 14. Steer the conversation toward your strengths.
  • 15. Silence your inferiority complex by asking the other person for advice.
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