Not 100% sure you can deliver on your early customers? Here’s how to talk about risk (and still get the sale)


You’ve got a new product you’re ready to start selling. And by some miracle, there’s already a major client ready to pull the trigger. There’s only one problem: You don’t know 100% if you can deliver for them.
So what do you do? Do you lie and tell them it’s 100% going to work? Or be completely open and honest and risk losing the sale?
Talking about risk with new customers is never easy. But luckily it doesn’t have to be one way or the other. There’s a way to talk openly about risk with your customers and still get the sale 99.9% of the time.
Why “fake it till you make it” is such a problem
We’ve all heard the stories of the founders who risked it all and won big. They said they could do something they were uncertain of and somehow pulled a rabbit out of their ass to make it work. But, let’s call these stories what they really are: fairy tales.
Yes, companies want to buy from confident founders. And bringing up uncertainty and risk—no matter how small—can feel like shooting yourself in the foot.
But when you’re trying to build and grow a successful startup, every new customer you bring on is taking a risk by choosing to go with you. Their business depends on you doing your job. So when you say “yes, we are 100% going to deliver” you better be damn sure you can.
I’m not saying you can’t use a bit of confidence to push for the sale, but too many founders and startups take “fake it till you make it” too far. Instead, it just becomes “Lie and hope it works out.”
This isn’t just a business dilemma, it’s an ethical one as well.
When the stakes are high for your customers, they’re equally as high for you. If you tell them there is a 0% chance of your solution not working and it crashes and burns, you’d better be ready for the fallout.
This is the dishonest and strong approach.
And sure, you might get the sale. But two months later when your solution isn’t working or bugs in your system are killing your customer’s business, they’re going to come back at you with a fury. And angry customers will kill your brand faster than anything.
But weakness during the sales process is just as bad
So, what’s the alternative? Full honesty and transparency?
Sure, you might think by telling the customer all the issues that could come up, you’re covering your own ass if things go wrong. But this is just as bad. I’ve seen so many startups make the mistake of leaning on transparency to the point of talking their customer out of the sale!
Instead of “Yes, we can 100% deliver” they go the complete opposite direction and say:
“To be honest, we don’t know for sure if we can do everything you’re asking. We think we can. But there’s a chance we can’t. We really want to work with you, so you can have it for free for a year, and if it works then you can start paying after that year.”
This is the honest and weak approach.
No, you’re not lying. But are you giving your customer the confidence they need to buy from you? Definitely not. Talking to prospects like this makes your solution feel just too risky for them. And when you don’t even value your product enough to ask for payment, you sound weak and 99.9% of the time, they’re going to back out.
How to come across as confident and strong when talking to customers about risk
It all comes down to how you frame the risk they’re taking.
You want to be confident in your solution, acknowledge the chance that things might not work out, and tell them exactly what you’ll do if that happens. This might sound a little vague, so let’s look at an example:
Let’s say you’re selling a new product to an enterprise company. It’s going to cost them $1 million for a year and it will take some serious work to implement it into their current system. And on top of all that they’re your first customer. They’re obviously taking on serious risk, so how do you approach it?
You say:
“You’re one of our earliest customers and we’re excited to work with you. So here’s what we’re going to do. We’re going to run a pilot. It still costs the full $1 million. But, because you’re a pilot customer, we’re going to include a full money-back guarantee. No questions asked. At any time during that year, if you’re not getting the value or service you want. Or if the solution doesn’t work as promised. You’re going to get all your money back.”
The Honest and Strong approach works because it offloads the risk to you
When you explain the risk like this and offer a money-back guarantee, you’re saying that you’re so confident in your solution that you will deal with whatever happens. You’re telling the customer there’s risk, but that you’ll deal with them. It’s being honest, strong, and transparent all at the same time.
Now, you might be thinking that “free” and “money-back guarantee” are just semantic differences. But there’s so much more to it.
Of course, in both scenarios the customer could end up paying you nothing. But when they have to give you $1 million and then come and ask you for that money back if it’s not working, they’re already showing they trust in what you do.
Being honest and strong is the only way to build a brand that lasts
As a new startup, getting your first few customers is incredibly hard. You don’t know what’s going to happen when your solution is out in the real world. But you need to be honest and transparent about the risk customers are taking. Use that risk as a chance to show that you’re confident, strong, and an honest company that looks after their customers.
So, no more “fake it till you make it.” No more weak “you can have it for free.” Be confident. Be strong. Offer the truth, but from a position of strength. And get the sale the right way.
Have you ever dealt with talking about risk to customers and had it go wrong? Let me know your thoughts and experiences in the comments.
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