Find The Line

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Years ago, I was speaking with a more experienced colleague about my sales woes. My pipeline was full of “maybes.” In my desire to allow people space to make a decision in their own time, I was acquiescing to all manner of stalls and put-offs that kept their buying decision in limbo. 

He asked me what I’d tell them if I wasn’t being so careful. I didn’t hesitate. I said, “I’d tell them I was okay if they’d decided not to work with me, but that I honestly believed that would be a mistake and that I recommend we move forward right away.”  

He said, “Cool, go say that...it’ll work.” 

I said, “I don’t want to cross the line!”

He asked, “Does that happen often? How often do you cross the line?” 

I said with pride, “I’ve never crossed the line.” 

Then my friend gave me advice that has helped to guide my sales and overall business decisions ever since. He said, “Go find the line and get back to me.” 

I made it my mission to find the line. I was more direct and said what I was thinking. I care a lot about people liking me, so it was tough, but I pushed forward. 

Know what? It’s hard to cross the line. And in my efforts to find it, I made a lot more sales than ever before. My confidence grew, and sales momentum built as I continued to be bold. 

Folks, consider taking my friend’s advice. You don’t get what you don’t ask for. You’ll be amazed at how many more sales you’ll make if you embrace a bold, direct approach.  

“Is there any reason we aren’t going to contract at this point?”

“If you were making the decision today, would you hire us? Want to just knock this out today?” 

It. Works. Give it a shot.

In case you’re wondering, yes. I’ve definitely found the line. Not often, and it’s not fun, but it has happened. If I don’t continue to find it from time to time, though, I’ll worry I’m leaving sales on the table.  

The Spark Notes: 

• For years, I played it safe in sales, letting prospects stall while I sat with a pipeline full of “maybes.”

• A mentor told me to go find the line—to stop worrying about being too bold and start saying what I actually thought.

• Turns out, crossing the line is harder than you think—and when you get close to it, that’s where the real momentum lives.

• If you want to close more deals, be direct, ask the question, and stop leaving sales on the table.