Pricing & proposals

Asking too many questions might be killing your sales potential.

A client had a prospect that wanted a small pilot. They got back a list of questions and a quote five times their budget (accounting for all the uncertainty).

I don’t blame anyone involved. The technical lead did exactly what had worked for them for 15 years. Before you price software, you need the full feature list. You need to understand the integrations, the compliance requirements, the edge cases. So they sent over a long list of discovery questions and priced for what they didn’t know.

That approach used to work. But I don’t think it does anymore.

Buyers right now want very little friction. A lot of them either don’t know the answers to those questions yet, or don’t want to spend time figuring them out before they’ve even decided to work with you. Every question you send is another reason to put the email aside for later.

What we suggested instead: make the decisions yourself, and show them what’s possible at different budget levels.

Here’s what you get at the low end. Here’s what you get in the middle. Here’s the full version, if and when you’re ready. With a unique technical plan for each.

You’re still doing the thinking. You’re just doing it for them, instead of handing it back as homework.

And most importantly, you’re not asking them to send 5 different people on their team Slack messages to get your questions answered. You’re giving them something to point to and say “We want that one.”

Show people what they can get. Don’t hand them a questionnaire.

Most of the sales calls you take are quietly deciding what you think you’re worth.

A client walked me through their pipeline recently. The large majority of their sales calls were with very price-sensitive buyers. Small budgets, lots of haggling, every dollar questioned.

That’s fine on its own. The problem was what it did to their head.

When a bigger buyer came along, one who’d picked them for their expertise and not their price, they quoted the same way. All those other calls had trained them to expect pushback, so they priced to avoid it.

We split every prospect into three buckets. People who were mostly shopping on price. People who wanted them specifically for something they were known for. And people who were looking for the best partner they could find, wherever that was.

Each bucket got its own pricing expectations. The third bucket, the most lucrative one, finally got priced like it.

On the very next call with one of those buyers, they raised their quote by 25 to 30 percent. The customer didn’t blink.

That’s the part that stuck with me. Nothing about their work changed between Monday and Tuesday. No new hires, no dramatic process change. The only thing that changed was what they believed their work was worth. 100% psychological shift.

If you’ve never had a client push back on your price, you don’t actually know where your ceiling is. You only know where your comfort zone is.

Keep raising your rates until you hit real resistance. Until then, your rates aren’t telling you much.

A client showed me a proposal they were about to send. Honestly, it was great. Clear, well designed, strong case studies.

The fixed price looked good too... until, just out of curiosity, I said, “So, tell me about the project.”

They’d had several scoping calls with this prospect, and nobody on either side could clearly say what the project was. One of the prospect’s own people described it as “a website with five tabs.” It was very obviously not a website with five tabs.

When the scope is that fuzzy, a fixed price is a trap. Either you pad it so much the client balks, or you price what you think they mean and spend the next six months finding out what they actually meant, on your own dime.

So we called an audible and changed what the meeting was for. It became an alignment check, not a pricing conversation. Walk through the proposal together. Is this what you’re picturing? What’s missing? What’s in here that you don’t need?

Then, have two paths ready.

If they confirm the scope, great. Here’s your fixed price.

If there’s still real uncertainty, offer a retainer for a dedicated team instead. They pay for capacity each month, and you figure it out together as the picture gets clearer.

Some people worry this adds friction to the sale. It does, a little. I think that’s healthy. A small amount of friction before the price protects both sides from a much bigger amount of friction later.

We love to obsess over fixed pricing. But you can’t fixed cost your way out of a bad project.

A client was told the budget. They came in under it... and they lost anyway.

Not by a little. The winning bids were less than half of theirs.

When they told me, I could hear the conclusion forming: “We’re too expensive. We need to drop our prices across the board.”

I get it. Losing a big deal that you thought was in the bag seriously sucks, and the easiest lesson to draw is the most painful one.

But I’ve been on the other side of this. Years ago, I lost a project I really wanted. We came in right at budget and got turned down flat. Months later I ran into the agency that won it at a conference. They told me, a little sheepishly, that they’d lost a ton of money on it. They just wanted the case study that badly.

You can’t compete with someone who’s willing to lose money to win. And you shouldn’t rebuild your pricing around them.

A few things are always true:

1. Enterprise budgets get spent. If the money’s approved, someone is getting it. Pricing yourself into the floor doesn’t make the budget smaller. It just makes your share smaller.
2. One weird outcome is one data point. Learn from it, but don’t let it become your strategy.
3. Ask yourself: if they’d come back and offered you the work at half your price, would you have wanted it?

Usually the answer is no, which tells you the price wasn’t the problem.

Lost deals teach you plenty. Just make sure you’re learning the right lesson.

PS. That agency who beat us out? They went out of business a couple years later.