Let’s talk about the “foot in the door” or “land and expand” approach to pricing—offering discounted pricing to entice a prospect to leave their current vendor partner and give you a shot. You tell yourself you’ll raise prices later, once they’re hooked on your quality and service. But let’s be honest: it’s like adopting a puppy and saying, “Sure, it’s fine if you pee on the carpet now. I’ll teach you to go outside later, once we’ve bonded.” Spoiler alert: later is a long, hard slog of un-training bad habits you allowed in the first place.
Starting a customer relationship by underpricing your work trains them to expect it. You’re signaling that your excellence comes cheap, and untraining that entitlement can take months or even years.
This isn’t just about lost revenue and profits—it’s about the long-term erosion of your pricing power. The moment you cave to a discounted “first deal,” you’ve set a dangerous precedent. You’ve handed them the keys to the discount kingdom, and now you have to figure out how to lock the gates.
The best way to avoid a bad habit is to prevent it from forming. If you’re excellent at what you do, your pricing should reflect that from the beginning. By focusing on outcomes and the unique value you provide, you create a foundation for mutual respect and value. Otherwise, you’ll spend years cleaning up messes you could’ve avoided.
Is it easier to get a prospect to switch providers with a discount? Sure—sometimes. But is it better? Not unless you have no other viable options. Too often, sellers reach for the discount lever because it’s the easiest one to pull, mistaking it for the only option. That giant, obvious lever blocks the view of more creative, less costly ways to win the prospect’s business.
If you think discounts are your only shot, lock yourself in a room with a whiteboard—and no distractions. Don’t come out until you’ve identified at least five ways to earn a prospect’s trial without discounting. Discounts are easy, but they’re incredibly costly. Do the harder, more strategic work of crafting other ways to convince the customer to try you out.
Pricing isn’t just about numbers—it’s about training expectations. If you teach customers that you discount to get in the door, don’t be surprised when they try to keep you there. Confident, fair pricing from the beginning sets the tone for a partnership rooted in a fair exchange of value. That’s a precedent worth setting.