Own your mistakes

Josh Sherman
3 min read

I fucked up recently.

Nothing that put any lives in danger, fortunately.

You see, I started doing a re-engagement campaign to reach out to all of my users that weren’t currently on my semi-monthly product update newsletter list.

This is actually something that’s come up quite a few times over the last year or so with some of my peers. Sitting on these emails was probably a gold mine. Low hanging fruit, they’d say.

It’s just that easy.

Well, maybe it could have been, if I didn’t fuck things up.

I thought I had crossed all of my T’s and dotted all of my I’s. I scrubbed my list with my own script. I paid to run the list through a cleaning service. I made sure to space out my sends and kept a close eye on my bounce and complaint rate.

Where I dropped the ball was on my copy.

I threw a post script in the email letting folks know that if you responded to the message I’d hook you up with a discount.

I completely failed to qualify the discount as only being available to users looking to upgrade from free to paid.

And of course I was hit up by a handful of already paying customers looking for their discount, most of which were already on grandfathered in pricing.

I sat on the requests for a short bit of time before starting to field the inquiries. A loss of revenue can really fuck with a small company, but if I’ve learned anything from my wife’s blog, negative press can be even worse.

Channelling my inner Jocko, I went full on with the Extreme Ownership and decided to honor the requests.

With that, without making things too difficult for folks, I explained how I fucked up and tried to find some concession that got them their discount, but also helped me out in the process.

For any customers that were on monthly, I offered up the option to switch to yearly in exchange for the discount.

Obviously this only works on folks already on monthly, so there were some folks that I couldn’t make that pitch to. For them, I hit them up with a customer survey with the 5 brilliant StoryBrand questions that easily translate into testimonials.

Not everybody filled out the survey, but nearly everybody I offered the switch to yearly to, took it. There was one lone individual saint that after I laid out the discount for going to yearly, felt their current rate was solid and didn’t want to take advantage of a small business owner like themselves.

The obvious lesson learned is that I absolutely need to qualify any future discounts, or the more likely scenario, never discount the brand like that ever again.

The less obvious lesson is that I should probably be trying to up sell monthly customers to yearly more often, especially since we’ve moved away from even offering up monthly plans anymore.

Even with a loss of annual revenue this week, by owning the mistake and trying to make the discount mutually beneficial, I was able to close out one of the highest revenue weeks of the year.

No more fuck ups for a while though, seriously.

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About Josh

Husband. Father. Pug dad. Musician. Founder of Holiday API, Head of Engineering and Emoji Specialist at Mailshake, and author of the best damn Lorem Ipsum Library for PHP.

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