Mastering the art of conversation

  • effective communication

Entrepreneurs have to be fantastic at conversation. There’s no way around it.

Then again, entrepreneurs have to be good at a lot of things. Building a successful business requires a plethora of skill-sets. But while these people spend hours upon hours honing certain skills they deem useful, others get overlooked. Conversation is one of them.

Why is it given so little thought? The main reason, we suspect, is because to most people, those other skillsets, the ones they spend hours upon hours working on, feel more tangible and “real” compared to the soft mushy stuff of conversation. Building conversation skills just isn’t all that important. This couldn’t be more wrong.

Conversation skills are honed and trained like any other skill: through self-awareness and practice. In this post, we’ll help you become a conversation master by offering some leading communication tactics that are simple and easy to implement.

This post is fully backed by established academic research. Our team of psychology and neuroscience PhDs have sifted through hundreds of papers, selecting only the ones of highest quality. You have the fullest confidence in all our recommendations.

Conversations and meetings: A founder’s life

Entrepreneurs are always in meetings. Their calendars often look like a game of tetris. Five separate one-on-one meetings can happen all before lunch. Then there’s external meetings with vendors, investors, and other entrepreneurs. Not to mention the slew of hiring meetings during growth periods. And you know what happens in meetings? Conversations.

So why don’t we walk through a typical meeting and pinpoint exactly what you can do to train your conversation skill-set. Each of the tactics we provide will be tied to the “life cycle” of a conversation: Beginning with scheduling and preparing, to initiating and finishing up the conversation.

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Setting up the meeting: Choose the location (wisely)

An important point to be made is that conversation happens long before you actually meet and begin talking. Mastering conversation means you need to put in some effort before the actual conversation starts. As you work on these behaviors, however, the level of effort will decrease over time.

Let’s say you’re scheduling an external meeting to explore a potential partnership. When you’re deciding on the location, know of a few unique spots in the area that you can suggest.

Choose a more stimulating or interesting place to meet to have a conversation with another person:

  • Meet at a trendy coffee shop over a typical Starbucks. Sorry Starbucks, once you’re over 25,000 locations, you’re probably no longer considered trendy.
  • Meet in a room with an outside view over a windowless one (“green” rooms with natural light are also known to boost cognitive performance). We also recommend putting in plants and some greenery throughout the office if you’re limited in terms of nice outside window views.
  • Even if you can’t choose a location, choose a particular spot in a room that is more interesting. Stand in front of a window or a piece of art.
  • If it’s nice out, have a “walking” meeting. Research has shown that walking can stimulate high level cognitive processes and creative thinking. It can also foster a sense of trust and cooperation among people.
office green walls

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The reason this works is because an exciting and interesting environment will make everything else seem more exciting and interesting to another person, including you and what you have to say.

The reason is because of an amazing theory in psychology called the misattribution of emotions. We humans are notoriously bad at pinpointing the exact source of what’s affecting our mood.

difficult to identify cause of your emotions

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If you have a conversation in an interesting and fun place, a person will feel a general sense of “pleasantness” or “goodness”, but they’ll be unable to identify the exact cause of that “goodness” feeling. Their brain, looking for an answer, takes a shortcut and says the “goodness” must be a result of what’s immediately in front of them: You and your words.

To learn more about these mental shortcuts – what we scientists call “heuristics” – you should definitely read Nobel prize winner, Daniel Kahneman’s book Thinking Fast and Slow.

Preparing for the meeting: Self-talk and self-write

Self-talk is an incredibly useful, yet simple, tactic that you can do to prepare ahead of time.

For example, before going into any conversation, remind yourself to “put your best face forward” or “your best foot forward.” The actual phrase doesn’t matter. Heck you can put your best elbow forward if you want. Just so long as you remind yourself that you can always present your best self in any social interaction. Take 2 minutes and go through a list that works for you. For example:

  • Remember a time you had a previous meeting and you nailed it. Ask yourself, what went well? What did you do that made it a success?
  • Think about the attributes that make you unique and different from others. They can be social, technical, managerial, etc. How do these strengths make you a better founder and a better person?
  • Think about your recent achievements at work. What is going well in your business? Think back on how far you’ve come to this point.
  • Go back to your “Why.” Remind yourself of the reason you do what you do everyday. This value should be unwavering and revisited multiple times a day. Ritualize your Why and always have it in the back of your mind.
  • If you’re particularly anxious about the meeting or experiencing some self-doubt (hey, we all do!), then try some of this self-talk in the third-person (your name) instead of the usual first-person. Research shows that doing so can help create psychological distance and conserve brain processing power.
put your best foot forward

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In a neat set of studies, researchers found that when people were given a one-liner of self-talk before a conversation, they were found to be more likeable and engaging conversation partners.

Even cooler was the fact that when others were asked to guess these people’s personality and IQ, the guesses were spot-on for predicting the self-talkers. But they were much less accurate when it came to predicting the non self-talkers.

What does that say exactly? Well, when you engage in even the simplest form of self-talk, it allows your real self to come through for others to see. The result: You are seen as more sincere, honest, engaging, captivating, and overall, a more interesting person.

Bonus Tip: If you’re able to, transfer this “best possible self-talk” into a writing exercise. This type of writing exercise – which is called “disclosive writing” – can be particularly effective. At the top of a page, fill in some of the prompts above.

Writing has numerous psychological and emotional health benefits beyond making you a more powerful conversationalist.

But to get these benefits, actually write it out. Step away from the laptop! As a number of studies are showing, “the pen is mightier than the keyboard.” The physical act of putting pen to paper is psychologically different and more effective, especially when it comes to disclosive writing. The sensorimotor experience of writing helps bring your thoughts to life and gives them shape.

Kicking off the meeting: Prime with positivity

Never start a meeting by jumping right in. As much as you might not like it, small talk is important for building rapport and trust. But instead of the usual, “how about this weather?” we recommend being more creative in your initial chatter. You should prime the person to enter into a positive state:

  • If your meeting is an internal meeting, then begin the conversation around a recent success story in the company. This could be raising the next round of funds, getting press coverage, or a recent launch.
  • Be sure, though, that the person had a hand in the positive event you bring up. If they didn’t, your priming will backfire as the person will likely feel that it’s a passive aggressive jab.
  • If it’s an external meeting, talk about an experience or event that the person just had in their life. This could reading up on their LinkedIn profile to see if they have had any recent accolades or accomplishments. You could also talk to mutual connects to find out about possible positive news. Whatever you find out, ask them about it and get them to elaborate and disclose.

The underlying assumption here is that in your meeting you want to have some positive impact or outcome. Priming the person with feel-good emotions at the beginning allows their brain to enter into a favorable state – what psychologist Barbara Frederickson calls broad-and-build – which then improves chances that the meeting will go well. The trick works off of the same set of cognitive biases, or heuristics, mentioned earlier with the fun and novel meeting place.

prime your recepient's mood

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Remember, the brain is wired to take certain shortcuts in order to determine the cause of a feeling or emotional state. The brain will (mistakenly) attribute the source of some feeling state to something – or somebody – else.

Use this bias to your advantage. If you are needing to address something that isn’t inherently positive, like asking an employee to join a new project that requires additional effort, then you should first prime them with content that is positive.

Bonus Tip: By the same logic, if despite your best efforts, the person begins the conversation by complaining for 10 minutes about how their basement flooded over the weekend, then steer clear of the less-than-ideal subject or question afterwards.

The brain’s biases work the same way for negative emotions as they do the positive ones. In this case, you’re better off waiting for another opportunity to bring some positivity back into the conversation.

Getting into the meeting: Ask for advice

As you’re into the actual meeting, be sure to ask for advice. In a sort of paradoxical way, asking for advice can gain you influence and esteem in conversation. In his book, Give and Take: Why Helping Others Drives Our Success, Adam Grant argues that engaging in this type of powerless communication is in fact very powerful and effective.

But the science behind advice-seeking comes with some caveats. To benefit from asking the right type of advice, remember the following:

  • Ask advice around a topic or subject that is difficult, not easy. Asking about something that is easy risks you being seen as either incompetent (you should already know the answer) or insincere (you are faking it to come across as naive).
  • When seeking advice, make sure the person you’re getting it from is the only person you’re asking. As soon as others know you’re asking multiple parties, you’re seen as desperate or scheming. This can come back to bite you. Chances are the world you live in is highly connected, and so asking a bunch of people the same advice will eventually come out.
  • Ask advice of people who are experts in that topic or subject. If you ask a novice, it shows you haven’t done your homework. Every person will have some expert opinion on something and know more about a topic than you, even your subordinates.

Asking advice properly can lead to a host of positive outcomes. In one study it was found that for those who asked for advice during deal conversations, they were successful at negotiating 42% of the time, compared with only 8% success rate for those who did not ask for advice.

ask for advice in a meeting

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Oddly enough, the vast majority of people are reluctant to seek advice during conversation for fear of being seen as incompetent. But the science says the opposite: Harvard research shows that individuals perceive those who seek advice as more competent and influential than those who do not seek advice.

Carrying on the meeting: Give honest compliments

As the meeting progresses, find a natural point in the conversation to compliment the person. Being complementary may seem like a good idea on a whole. But there are some caveats to consider:

  • It sounds obvious, but be honest in your compliments. In most cases, insincere flattery is not received well. You can try and fake it, but as much as you may think you’re fooling the other person, you’re probably not. Our brains are wickedly good at detecting cues of dishonesty. Read up on how you can pick up on different body language cues during conversation in our other post.
  • One way to get this across is by making sure the compliment is perceived by the other as a “true signal” of cooperation. This means that when you compliment, you need to prove to the person that you are complimenting them not for selfish gain but because you feel strongly about what you’re saying.
  • Only be complementary in a one-on-one meeting. Never in a group setting. The research indicates that even when your compliments are sincere and honest, other observers will form implicit (unconscious) attitudes of envy and jealousy, because of the simple fact that they aren’t the one who are the target of your praise.
  • Finally, do your homework beforehand. Ask around to see what sort of recent accomplishments the person has. If you know these ahead of time, you can steer the conversation in that direction to allow the compliment to be easily dropped in.
give honest compliments

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Rounding out the meeting: Ask a question

As the meeting winds down, you should end by once again engaging in some small talk. What works well here is asking a question.

But it’s not just any old question. The question you should be asking are the ones that get a person to self-disclose. If you do this well (and you get the other person talking about themselves), you’ll be perceived as likeable, trustworthy, and engaging. Here are some good examples to use:

  • Ask if they have any hobbies or things they like to do outside of work and business.
  • Tell them you’re searching for a next set of books/blogs/podcasts and ask which ones are their favorite (and why).
  • If they’re immigrants (a likely possibility given that a significant portion of North American entrepreneurs immigrated over), ask them about their heritage culture/country, and how the transition has been.
  • Related to above, ask about the entrepreneurial and startup life in their country. Is it similar? Different? How so? Ask if they’ve heard of Linda Rottenberg’s company Endeavor, the mega successful not-for-profit whose mission is to foster entrepreneurship in countries all over the world.
  • Caution: For all these questions, don’t just ask them out of the blue. There has to be a context where the question you’re asking is a natural part of the conversation, rather than just dropped out of nowhere.
ask a question in meetings

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Follow-up questions can be particularly effective. They indicate to the partner that you’re actually listening to what they’re saying and being considerate of their emotional needs. To be good at this, you really have to pay close attention. You can learn to train your attention and focus by reading our post.

In general, people love talking about themselves and their own experiences. It’s been found that people prefer to talk about themselves over getting paid money. Doing so activates the dopaminergic system in the brain, suggesting that the experience of talking about oneself is inherently pleasurable and rewarding.

In a very recent set of studies out of Harvard Business School, it was confirmed that people were liked more during conversation if they asked their partner more disclosive type questions. Ironically, the partner indicated they knew less about the people who asked more questions. But it didn’t matter. They still liked them more.

Recap and the Final Word

Here’s a recap of what you can do in order to become a conversation master:

  • Set the meeting by choosing an interesting location. To the other person’s brain, interesting location = interesting conversation
  • Prepare your best self for the meeting before with some self-talk tactics. You’ll be seen as more influential, impactful, engaging, interesting, and likeable.
  • Start the meeting/conversation by priming positivity. Again, to the other person’s brain, a positive start to a conversation = positive impressions throughout.
  • Get into the meeting/conversation and ask for advice. Doing so will make you actually seem more competent, not less.
  • Carry on the meeting/conversation and give a compliment. But remember the rules of how and when this works best.
  • Round out the meeting/conversation with getting the person to self-disclose. You’ll be liked more if you can get them to talk about themselves.

You probably have dozens of conversations every single day. For something that you do so often, it only makes sense that you work on and train this skill-set.

So remember these easy tips for the next time you have an important meeting and you’ll be a conversation master in no time.