Never reach out twice with the same value proposition

When I joined Channels two years ago, I knew next to nothing about sales. Now, I know just just the teensiest bit more than that. Basically everything that I’ve osmosed (osmoted? osmoosed?) has been from our company’s founder, Curtis Wiklund. He and his wonderful wife Jordin are incredibly talented and ran a successful photography business together for years before he founded Channels. It turns out that operating your own small business is a great motivator to develop sales skills.

One basic lesson that he’s taught me is to never reach out twice with the same value proposition.

To illustrate what I mean, imagine you receive this email from an interior decorator you’ve considered working with:

Dear Jenny,

I was reaching back out to you to ask if you’d had any further chance to consider working together. I have lots of happy clients and would love to work with you to craft your perfect home.


That’s a very polite email! Thanks George.

Unfortunately, that email probably doesn’t meaningfully alter your chances of hiring him beyond “if I just forgot, maybe I’ll follow up now”.

Furthermore, you’ll probably tolerate one or two of those emails before you wish George would shut it and go away.

That’s fine, but George can do better. Now, how would you feel if you received this email instead?

Dear Jenny,

Loved chatting with you the other day!

I’m reaching back out because an upholstery brand that I think you’d really love (Hickory Chair) is having their biggest sale of the year right now. I’d be happy to stop by to see if any of their items might help solve that pesky living room seating issue you mentioned.

As an example, here’s a piece I thought you might like:

A picture of a couch


Now I don’t know about you, but I’m much more likely to reach out to schedule a meeting after that second email. It’s polite, recognizes that George listened during the last meeting, and offers a meaningfully different value proposition than he put forth in your initial meeting.

Assuming that George’s barometer of what appeals to you is correct, he can probably reach out with many more of those emails before you get annoyed. They’re thoughtful and likely take him more effort to craft than it takes you to read them: it’s a little like having a free personal content curator working just for you.

It takes real effort to find that new value proposition. Often, it requires some combination of passive effort (keeping your eyes open for something that matters to that person) and active effort (passing along that new value proposition when you find it). However, it’s that very effort that demonstrates to the recipient that you care and makes the pitch much more effective.

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