Why Every Entrepreneur Needs to Be a Better Conversationalist (and How to Do It)

Photo by Mimi Thian on Unsplash

There are countless skills that every entrepreneur needs to have, from creative brainstorming to logical analysis and decision making. They range in complexity and specificity, with basic skills like time management permeating your day and more complex skills exclusive to your industry that you can only acquire through experience. But there’s one skill that’s incredibly basic, yet underrepresented in the modern entrepreneurial community: the art of conversation.

Everything Starts With Conversation

Your conversational skills are a deciding factor in how several important experiences play out during the course of your business leadership:

· Presenting your business plan to investors, persuading them to invest and listening to their ideas and feedback.

· Getting your first clients on board, and convincing them to stick with you.

· Choosing your team members through interviews, and retaining them with high morale.

· Managing, organizing, and delegating tasks on a daily basis.

· Collecting feedback from your team and clients, and making the improvements.

It’s a foundational skill that will affect literally every area of your business, yet there is no “conversation” class in business school, and we rarely get the opportunity to critique our own performance.

How to Be a Better Conversationalist

Fortunately, there are some habit changes, exercises, and general considerations that can help you become a better conversationalist overall:

1. Pay attention. There are tons of articles that tell you to act like you’re paying attention by making eye contact, nodding, and repeating back what the other person has told you. But as Celeste Headlee humorously points out, why would you need to act like you’re paying attention if you are, in fact, paying attention? When you converse, don’t just wait for your next opportunity to speak — truly listen to what the other person is saying, absorb it, and reflect on it. You’ll understand their meaning more clearly, and you’ll respond more appropriately.

2. Ask open-ended questions. The common advice to holding a better conversation is to ask more questions, but that only tells you half the story. You can’t just ask a series of rapid-fire questions and hope to get good answers. Instead, you have to ask open-ended questions, which force the responder to give you more meaningful information. Don’t ask, “do you like our new website?” This forces a “yes” or “no” answer, which closes the conversation and gives you little meaningful information to work with. Instead, consider something more open, like “what do you think of our new website?”

3. Let the conversation take its course. During the course of conversation, there will be many twists and turns. Try to let them happen as naturally as possible. You’ll have many thoughts and talking points enter your mind throughout, but don’t interrupt the flow of conversation to bring them up — it’s fine to let them go. Your goal here is to keep the dialogue active, with a positive rhythm, so unless you deviate far off course from your intended direction, let these natural changes unfold.

4. Err on the side of caution. People will hold you at your word, so be careful what you commit to and what you imply you know. For example, if a client asks you if you can customize your software with a new tool, don’t respond “yes” to keep the conversation moving (unless you know the answer is “yes” for sure). “I don’t know” is a perfectly acceptable answer, as long as you follow up to get the answers eventually. Doing this will allow your conversations to set more reasonable expectations and will set you up as a more powerful authority.

5. Skip the details unless necessary. Conciseness is a powerful tool that makes your words more meaningful, and helps keep the conversation on track at the same time. That doesn’t mean you should respond in snippets of only a few words, but it does mean you should avoid dredging up any details that are unnecessary for your bottom-line points. For example, if you’re not going to hit a deadline, but you have a plan to get the work done in another day or two, don’t bother explaining every domino that fell to get to this point to your client — instead, keep it high level unless they ask for more details.

It takes time to become a better conversationalist, just like it takes time to be a better anything, but the more time and energy you invest in your skill, the more it’s going to reward you in your future engagements. Plus, being a better conversationalist is more than just a line on your resume — it’s going to help you be a better friend, a better relative, and maybe even a better stranger. You’ll connect with people more deeply and meaningfully, and you’ll experience fewer miscommunications. Who doesn’t want that?

For more content like this, be sure to check out my podcast, The Entrepreneur Cast! And be sure to check out my business, EmailAnalytics, which visualizes your email activity — or that of your team.

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!