Find Quick Wins Just By Having the Courage to Ask


I was reminded the other day that sometimes it can’t hurt to just ask. The fear of being too pushy or coming across as a greasy salesman to your customers can leave you very hesitant to ask them to spend money with you.

It’s always smart to walk that line carefully, but you’ll miss lot of opportunities if you let that fear keep you from making even the smallest of decisions.

A site we’ve been working with sent out a very simple message recently to their members – pretty much on a whim – to see if they would switch from the monthly to the annual plan. “It can’t hurt to ask, right?” they muttered as they hit the send button.

Hey {First name},

Would you be interested in nearly two free months of {Premium}? Switch to annual billing, and that’s exactly what you get!

Your account is currently at the {N monthly rate}. If you switch to annual billing, we’ll only bill you once per year (making accounting much simpler) and you’ll save {XX%}. That’s nearly two months of free {Premium}!

If you’d like to switch to annual billing, just reply to this message and I’ll get you switched over.

You will also keep any discounts currently applied to your subscription.

{Your name}

P.S. if you’re not interested then no worries, nothing will happen.

That message ended up converting 2% of the people they sent it out to. It’s certainly not a success case that they are going to pop champagne over, but it sure as hell beats the alternative of having done nothing. Even at 2%, this resulted in several thousand dollars and a big win reduction in their churn rate (since annual members cancel wayyyy less than monthly).

This is also something they can set up as an automated message to send out periodically, multiplying the benefits over time.

I challenge you to send something like that out to your customers this week. The goal doesn’t have to be that they spend more money with you. It could just be to take a quick survey, answer a question you have, try out a feature and respond with their thoughts, or even share your product on social media.

To give yourself the best chance at this being effective, here are some things you need to keep in mind:

  • Keep it short, simple and only ask for one thing. You’ve got a much better chance of getting them to act if there is one clear path for them to take. Ask for something that will take less than a minute for them to do.
  • Be very clear about how this benefits them. Notice the very first sentence in the message I shared earlier. Even answering a question or survey can benefit them by helping you know how to serve them better.
  • Reassure them that you are really grateful for their business already and that not responding to your request doesn’t penalize them in some way. No guilt trips 🙂
  • Reward them for responding. At the very least, send them a personal thank you for taking the time to do what you asked. It will go a long way toward making them feel more connected to you and more likely to respond again in the future.

Enjoy the experiment, and post a comment below to let me know how it goes!