Joe OviedoWhen I’ve written four headlines and could make a case for all four, I start to suspect I’m using words to avoid a decision. I can swap “Get your sales organized” for “Sell with more clarity” and spend a while debating which sounds better. But ask me what someone would be doing on the day they realized they needed my help, and I might not have an answer.
That’s the moment I’m interested in. Not when they read my page or compare prices. A little earlier. What just happened in their business that would make them care about what I have to say?
“I didn’t know whether to write again”
Imagine I want to help independent professionals get a handle on sales. I start with a reasonable hypothesis: they send proposals, don’t follow up, and miss out on work. I could put a workshop together quickly. An email template, a follow-up schedule, and a way to track replies. I could even write a convincing page without talking to anyone.
Now imagine I sit down with someone and, instead of asking whether she struggles with follow-up, ask about the last proposal she sent. She says, “He told me he’d look it over. A week went by and I didn’t know whether to write again or leave it alone.”
At first that sounds like I was right. She didn’t follow up. But if we keep talking, I might find out she did write the email. She left it in drafts. She opened it twice but didn’t send it because everything sounded like “Have you read my proposal yet?” She didn’t want to chase someone she’d had a good conversation with.
That changes what I’d offer. A reminder would tell her something she hadn’t forgotten. A template might help her send the email, but I’d still wonder why picking up a conversation that went well now felt like intruding.
Go back to the moment before the proposal and we might find that nobody agreed when they would review it. He said, “Send it over,” and she took that to mean he’d get back to her. He may have expected a document to look at whenever he had time. There was no argument or rejection. They left the conversation expecting different things to happen next.
I’d arrived thinking the problem began a week later, with an unsent email. Now I’d work on the last two minutes of the first conversation: how to agree when to talk again and what to review together before making a decision. It’s a smaller intervention than I had in mind, but it addresses the problem before it shows up.
I wouldn’t use that line as a headline yet
It’s tempting to hear “I didn’t know whether to write again” and think I’ve found the headline. I’d write it down exactly as she said it. Before using it, though, I want to see whether my reading holds up when I talk to other people.
Someone else might have agreed on a date, followed up, and still heard nothing. Their proposal might make the client read eight pages to find out what’s included and what it costs. A third person might spend the week chasing proposals they wrote before asking about budget. All three could say, “I struggle to close.” I wouldn’t ask them all to practice the same email.
Listening becomes a way to decide whom I can help. If I want to test a session on restarting stalled proposals, I want someone who already has an open conversation and doesn’t know how to move it forward. Someone who has no one to talk to yet needs something different. I might help them another time, but I don’t want them to pay to find out this session wasn’t for them.
I also like asking people to show me what happened: the message, the proposal, or the draft that never went out. I’m not looking for a mistake. It’s just that when we tell a story from memory, we tend to reduce it to “they stopped replying.” The detail that changes everything might be a line neither of us remembered.
What I’d feel comfortable promising
I could write “Sell more without chasing clients.” It sounds good. The hard part is saying what I’ll do to make good on it. I can help someone reopen a conversation. I can’t decide for the person receiving the message.
I’d be more comfortable with something like: “Bring a proposal you sent that went unanswered. We’ll look at where the conversation stalled and come up with a way to pick it back up.” I’m not committing to close a project on anyone’s behalf. I am committing to work on a real case and make sure the person doesn’t leave with another list of tips to read later.
Before building an entire workshop, I’d try that session. What happens when someone brings a real proposal? Is the problem where I thought it was? Can we do something useful in the time we have? Does the person leave knowing what to write, or do they first need to clarify what they’re offering? I’d rather find out while I can still change the service, not after recording six modules.
That’s why I go back to listening when the headline doesn’t convince me. Sometimes two words do need changing. Other times I need to understand why someone has spent a week opening the same draft without sending it. Once I understand that, I have something better than a line for the page: I know where I’d start if that person sat down across from me.
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