
Hot Take: Timid selling is worse than pushy selling
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Finding the right tone to take in a sales conversation can feel like walking on a tight rope.
You can’t to be too pushy because it feels gross and no one likes to be hard sold.
But you can’t be too passive because then you’ll just waste everyone’s time.
We don’t talk enough about how annoying it is to talk to a business owner that’s too passive on the sales call.
I, unfortunately, just had this experience. So, I’ll tell you just how negative of a client experience being overly passive on a sales call creates for your buyers.
Here’s the story:
The call was essentially 25 minutes of vague monologuing.No clear ask.No structure.I had to ask twice what the next step was.I left the call confused and irritated.
Here’s what went wrong (and what you should avoid):
🚩 He wasn’t clear on what he wanted to accomplish in the call.Turns out he was looking for a founding team member. Just say that. Don’t dance around it. Say the thing. If you don’t say what you want out of the call, how can your buyer know what you want?
🚩 He did zero discovery.He talked at me for 25 minutes. Didn't ask what I care about, what I offer, or even if I'm open to the type of relationship he was (not really) pitching.
🚩 He didn’t know his own next step.He finished talking at me and I had to guess what he wanted to happen next. I asked if he was looking for an equity partner, he said “I’m open to that.” Confused… I asked if he was looking for something else. He said “no, that’s what I’m looking for” Sir. 😮💨
Outcome of the call? He’s on my double-the-rate-if-he-ever-follows-up list.
Here’s the lesson:
Being too timid to pitch costs you deals and it can cost you relationships.
I’ll say this forever: you selling your thing is not pushy, it’s helpful. Go be helpful!


