Conversations That Sell

If you dread selling, you're in good company. Many people who are excellent at their work find asking to be paid for it the hardest part of the job. Founders put off the follow-up email. Freelancers lower their price before anyone has objected to it. Consultants write a twelve-page proposal instead of asking one direct question.

• Explain why selling is a conversation skill rather than a personality trait
• Recognize four specific ways your brain misreads sales conversations
• Tell the difference between a useful no and a costly maybe
• Reframe your goal from persuading people to helping them decide

Most advice about finding clients starts with the pitch. Write a better offer, sharpen your website, perfect your cold email. Those things matter, but they skip an earlier question: who are you talking to?

• Map the places where your next clients are most likely to come from
• Recognize which settings produce real sales conversations and which only look like they do
• Explain the feast-and-famine cycle and how to break it
• Design a weekly conversation calendar you can keep up even when you're busy

Most people who dislike selling dislike this part most. The first message to someone who doesn't know you. The moment at an event when someone asks "So what do you do?" The first two minutes of a call with a potential client, when it isn't yet clear who's leading.

• Open conversations with potential clients and contacts without sounding like a pitch
• Tell your network what you do, and ask for introductions, in a way people find easy to act on
• Write short cold messages that make replying easy, including replying no
• Open a first call so the other person talks first and both of you know what the call is for

Discovery is the part of a sales conversation where you find out what's actually going on. It's where the mission from Module 1 becomes practical. You can't help someone make a good decision if you don't understand their situation, and they can't judge whether you can help if you haven't shown them you understand it.

• Hold back your solution until you understand the problem
• Use follow-up questions to get from the first problem mentioned to the real one
• Explore the impact of a problem so both of you can judge whether it's worth solving
• Ask about budget, decision-making and timing without it feeling intrusive
• Recognize when you're not the right fit, and say so

Every sales conversation sends two streams of information: what people say, and what they do. In selling, the second stream is usually more reliable. People say pleasant things to avoid awkwardness. What they do, whether they ask questions, bring in colleagues or agree to a next step with a date, tells you much more.

• Recognize the signals that show real buying interest
• Distinguish politeness from interest, and check gently when you're unsure
• Tell "not now," "not you" and "no" apart, and respond to each
• Read a meeting with several people who have different priorities
• Adjust your approach during a conversation, including your own state

For many people who sell their own expertise, the price is the hardest sentence in the whole conversation. It can feel like you're putting a number on yourself. So people rush it, apologize for it, bury it in a long email or lower it before anyone has asked.

• State your price plainly and stay quiet afterwards
• Use ranges and scope options instead of discounts
• Explore an objection before answering it
• Negotiate by trading, and know your walk-away point before the conversation
• Write proposals that lead to a decision, and walk away well when it isn't right

A good conversation is only the start. Plenty of deals that should happen never do. Usually the client didn't say no. Nobody asked for a decision, the follow-up never came, or the next step was "let's be in touch."

• End sales conversations with a clear, agreed next step
• Ask for a decision plainly, without pressure or tricks
• Follow up in a way that's useful rather than chasing
• Turn delivered work into repeat business and referrals