Art of Conversation

Entrepreneurs have very little time to waste. Learn how to maximize the efficiency and productivity of every conversation you have.


As an entrepreneur how much time have you spent massaging your business model, figuring out the financial model, running the Pro Formas, working through Excel and trying to imagine every different future and scenario? If we’re honest with each other the answer for all of us is probably a lot. We spend a lot of time doing that. A lot of spreadsheets, trying to figure out the business model.

Now here’s a different question. How much time do you think you spend in a given week in this construct we call a conversation? That can be an email conversation with prospects, it can be an email conversation between you and your team, one‑on‑one conversations in live meetings, one‑to‑many in a presentation. But this construct called the conversation, how much time do you spend in that? Again, I think the answer is a lot. You spend I don’t know what it is 70 percent, 80 percent of your time in this thing we called a conversation.

Now, last question. How many of you have been formally trained in how to have a conversation? I would imagine if we’re honest the answer is not many of us have been formally trained in how to have a conversation. Not many of us have learned about how to optimize something where we spend 70 to 80 percent of our time, this thing that we do called conversation. And I think that’s a challenge for entrepreneurs. Because as entrepreneurs one of the things we know we have to do is get into and run effective, impact conversations every chance we get. Why? Because we don’t have time to waste.

So I like to think about a conversation with three foundations. There are three foundational principles that underscore and support an impact conversation. And I think about them as bubbles. If you start on the left‑hand side, a little tiny bubble. The first bubble or on‑ramp to a conversation is called the purpose benefit check. The purpose of our talk today is to look at this construct called the conversation. What I hope you’ll gain out of this is a sense of the three main foundations of an effective impact conversation. How does that sound? Purpose, benefit, check. It’s very simple. Most of us show up with an agenda, which is fine, a written agenda on a piece of paper. Sometimes we don’t show up with an agenda. I’m okay with that. Either way is fine. But then the question is even if you have a written agenda how to drive alignment with a customer? You do that with words. You do it with a purpose benefit check. It insures that you’re in the right room. It insures that that prospect or customer is going to get what he or she came for. Or it corrects an error. I made a judgment, and no, she wants to go somewhere else with this meeting. And if I just launched into it, 20 minutes later I find that out, that’s wasting both of our time. Purpose benefit check is that on‑ramp. It’s the words that you say. It’s the alignment that you create in the room between you and someone else. And it gets you up to speed into a proper conversation quickly and effectively. So that’s foundation number one.

Now think of a slightly larger bubble. The slightly larger bubble is what I call impact questions. Think about the different types of questions you ask as a professional and entrepreneur, just a person. You ask closed‑ended questions how’s this, is this going okay so far, yeah, no. You know, that’s close‑ended questions. Or an open‑ended question, that’s a different type of question; how’s this going so far, is it okay? Yeah, it’s okay, it’s going well or not so well, whatever. What if I asked you an impact question? It’s a different level of question. What if I said based on this session, what are you going to do differently at work next week? That’s an impact question. People go huh, that’s a good question. You just asked an impact question. You made them stop and think or analyze or feel something, right? You made me stop. That is powerful in a conversation. It’s one of the foundations of a good conversation. Because you’ve made me think, and now I’m considering, I’m considering your company, I’m considering your product or service. So impact questions is key.

And then the third bigger bubble. As this conversation expands there’s something critical that we as entrepreneurs have to do. We have to qualify. So the different type of questions that live in that third bubble and really are the machine, the engine that runs conversations, is the ability to ask qualifying questions. As entrepreneurs we have no time to waste. And so we need to establish qualifying questions like does this person have the budget, is she the decision maker, and will she make a decision in the time frame that makes sense for me and my business. You have to establish those qualifying questions in any impact conversation. And these happen over time as the sales process goes. Even as you get to know the potential customer better you still have to qualify. These are the questions that’s going on in the internal conversation that you’re having in your head.

So these three things, provide a foundation for a powerful impact conversation. Because at some sense as an entrepreneur, in some sense you don’t have time to have any other kind of conversation. You can’t leave it to chance. And you can’t waste time. And these three foundations will provide you with an opportunity to wring out and be most effective in every conversation.

Suggested Readings

Founders School || Entrepreneurial Selling || Art of Conversation || Impact Guide (PDF).

Pink, Daniel. To Sell is Human: The Surprising Truth about Moving Others. New York, NY: Penguin Group, 2012. Ch. 4-6.

Wortmann, Craig. “Communicating with Influence: The 3 Most Essential Tools“. Sales Engine Inc., 2013.

Wortmann, Craig. What’s Your Story? Evanston, IL: Sales Engine, Inc, 2006. Chapters 1-3.

James, Geoffrey. 2 Sentences That Engage Customers. Inc. Magazine. June 3, 2013.

Deighton, J. and Das Narayandas. Siebel Systems: Anatomy of a Sale, Part 1 Case Study. Harvard Business School Case 503-021, 2003.

Questions for You

How comfortable are you asking for things? How comfortable are you with silence?

What two words would people use to describe your conversation skills? How concise are you in your description of the business?

What are the impact questions you should be asking your customers? How will your product make a difference?

Listen to the founders featured in Founder Genius talk about their approach to these conversations. How can you ensure that you really listen to your customer?

Tools and exercises

Qualify (PDF): Qualifying is simply asking questions. Budget, timeline, and decision-maker are the holy trinity of qualifying questions. But every entrepreneur will have additional qualifiers that must be answered to close a sale. Technology fit, team compatibility, cultural considerations, and risk tolerance are just several qualifiers that must be addressed.

Create a Sales Trailer:  Sales Trailer(℠) – A question you’ll often be asked is “What do you do?” And you should have an answer to that. I call it the “Sales Trailer(℠).” The Sales Trailer(℠) is the ‘movie trailer’ of your business. Every day, someone asks me “What do you do?” And I say; “I help companies build and tune their sales engine.” That’s my Sales Trailer(℠). It’s tight, clean, and it gets the job done. I call this an “on-ramp to conversation.” It’s not meant to tell someone everything about my business…that’s too much. It’s simply meant to start a conversation in an engaging way. Entrepreneurs often say WAY too much (I know I do!). The Sales Trailer(℠) is a way to be engaging, concise and open a conversation. That begins the selling process!