Week 30: I made some mistakes

(I briefly moved this email from Sunday to Tuesday to see what it'd do to the open rates. Turns out they're exactly the same—~55%. I like Sunday better, so here I am again.)

After 30 weeks of starting my company, I've made more mistakes than I can count.

I spent this week doing something that's interesting to do, but not interesting to write about—adding customer-requested features. So rather than talk about that, now’s a good time to tell you about the bigger mistakes I’ve made, and their corrections.

Opening meeting with rambling

How do you open a sales call? Do you ask where they’re from? How their day is going? Do you just start in?

Sometimes, I suddenly get nervous and just start rambling about my product. It’s clearly the wrong thing to do, but it’s hard to stop.

This happens when I don’t take a few minutes before the call to take a deep breath. I need to know, beforehand, how much I’m going to need to explain who I am and why we’re on this call together. I need to consciously decide how to pivot from setting the context to asking the customer about their problems.

Overestimating deal strength

Have you ever had a first sales meeting, and it goes so well that you can’t help but be incredibly excited?

Sometimes it’s warranted: the customer has a need for your product, budget to buy it, and time to adopt it.

But sometimes it’s a trap. If I really need a win, I feed off the excited and ignore qualifying signs that I’d usually pay more attention to. Does the customer really have the problem, or were they just being nice?

This is a painful one: it leads me to overestimate the strength of the deal and assume it’s in the bag. It’s not. It’s just the start of a slow, dead deal.

This happens when I’m overeager to close a particular account. I need to remember that if the account is make or break, the market isn't big enough anyway, so it doesn’t make sense to get hung up on it.

Compulsively checking email

This one needs no explanation, and I still do it anyway. But why does it happen?

If I’m feeling down and need a win, I hope something good is just going to turn up. It’d be easier for a win to simply fall into my lap rather than rely on a plan.

So in desparation, I refresh my email like I’m playing the lottery.

Here’s the correction, which I’ve yet to internalize: If I’m running a plan I believe in, either it will or won’t produce results. If it does, the results can wait until tomorrow. If it doesn’t, I can just make a new plan. I don’t have to stick with this forever.

Convincing everyone

If I’m in a conversation and realize I’m talking to someone who has no use for my product and doesn’t even have the problem I solve, I sometimes try to convince them anyway.

Why do that? It’s ego. I feel like I need to win the argument to feel validated about what I’m doing.

It makes zero sense to try and convert a person who will never be a customer. It's illogical and a waste of energy. Besides, no product is for everyone. I’m not the exception to the rule.

Pitching a friendly

Have you ever pitched someone—maybe a friend—and watched them get excited really quickly? They immediately start asking you heaps of questions about your product.

It’s hard to stop it—it feels good having someone take an interest in your work. But unfortunately, it’s a mistake if you let it go too far.

If the meeting becomes all about tech and not about their problems, it becomes way harder to have enough momentum to do a deal later on. It drags you off the right trajectory.

Momentum comes from the customer being convinced that they have a problem you solve. If the customer’s focus is on the product, not the problem, it’s hard to justify the dollars to make the sale.