My roommate's bad date

My roommate went on a date. She came back disappointed.

"I just don't think he liked me that much," she told me.

"Why not?"

"Because I wanted him to take me home, but he never asked."

But apparently he liked her enough to ask her on a second date. The two of them went out again. Again he didn't invite her back to his place — and again my roommate interpreted this as "he doesn't like me".

I didn't meet the guy — but I'm guessing he liked her. He was probably just too shy to ask.

I say that because I've been in his shoes before — I've gotten in my own head about a girl I liked, wondered what the best way to escalate things was, and then just ended the evening without even trying... even when she clearly wanted me to make a move.

I had the same problem with sales. I would get on sales calls and fumble around with my offer.

Or I would pitch them something small because pitching something big was too scary to me.

A lot of them would wonder where the call was going, exactly. Others would judge me as unprofessional because I was too afraid to ask for the sale. They wanted me to just ask.

I've gotten over that, thankfully — but a lot of beginner coaches haven't. (And even some intermediate level coaches, too.)

If you think selling is "icky", or you're too afraid to ask for what you want, you're not just costing yourself sales. You're actively disappointing potential customers who want to buy from you.

They don't want to take the lead — they expect you to take the lead. Most people won't interrupt you on the sales call to say, "hey, I'm ready to buy this, let's do it." You have to make the ask.

I'm not saying to use high-pressure sales tactics or to scream at people until they buy — nobody wants that. But you can go too far in the other direction, too. If you want to help people, you need to (respectfully yet confidently) make them an offer!

-Theo