I’ve used the same online time-tracking service for 15-ish years. Last week I got an email: they’re switching business models, and my subscription is jumping from $138/year to $1,158. That’s a 739% increase, with a few weeks’ notice.
The number stung. The email stung more. Long, patronizing, and it basically said pay up or get out. No nod to 15 years of loyalty, no acknowledgment of how big that jump is, not even a fake “sorry to see you go.”
Thankfully I’d had a heads-up from angry colleagues who got the email first. Some pushed back and got a partial reduction for next year. But it cost them time and hassle, and they’re still paying way more than before. I’m not doing that. I’m out.
Let’s be clear: raising your prices is not the problem. You should be doing it regularly—I talk about this in Good Work!. The problem is how. Here’s what this company got wrong, and what you should do differently.
1. Notice matters more than the number. A jump this size needed 2-3 months of warning, minimum—even without the final figure attached. People need time to make a number like that fit their budget. Dropping it on someone with three weeks left isn’t a business decision, it’s an ambush.
2. Loyalty is currency. I’m a small account to them. But 15 years of subscription fees and word-of-mouth referrals isn’t nothing, and they just torched all of it for a short-term number. If you’re raising rates on a client who’s been with you a long time, say so. Something like: “You and I have worked together a long time at $X, and my new clients are at $Y. I’d like to bring you closer to that—what feels workable for you?” That’s a five-minute conversation that buys you years of goodwill. Skipping it costs you the client and the referrals they might have sent you. And even if they say no and leave, you’ve included them in the conversation, made the choice theirs, and haven’t burned any bridges.
3. Give people a way to say yes, not just a bill. There was no tier, no phase-in, no negotiation—just a number and a deadline. This is exactly why I don’t raise rates the same way for everyone. New clients get my current rate from day one—they don’t know any different, and it’s a great way to test whether the number is right. Existing clients get grandfathered in slowly, usually through that same negotiation from tip #2. I might bring them up 10% this year and another chunk next year, rather than jumping them straight to the new-client rate overnight. It costs me a little short-term revenue, but it means nobody I’ve worked with for years opens an email to find their price tripled overnight with no warning and no say in it.
The takeaway if you’re the one raising prices: give real notice, charge new clients your new rate from day one, and bring your long-standing clients along slowly, with a real conversation instead of a bill.
I’ve got three weeks to find a new home for 15 years of time-tracking data. If you’ve got a tool you love, I’m taking recommendations.