Nobody likes to fail. I’m no different. But my fear of failure has an interesting behavior. Over the years I’ve realized a pattern when it comes to my failures: When I’m challenged to do something for the first time, I might be scared but I’m able to convince myself quite easily that I have nothing to lose. I tell myself (or actually feel deep down) that there are absolutely no expectations of me since I haven’t done it before. I’m an underdog. Failure is the most probable result anyway, so I might as well try. Usually, I’m so convinced to give it a try that I actually succeed quite nicely in most things, surely for a beginner.

That was the case with Infinify, my product leadership academy, when I decided to “give it a try” while I always have the option to go back to a CPO role in the industry. That was also the case with the CPO Bootcamp – after having consulted for a while I decided to build a group program, and invited early adopters to join me for the first ride. We ended up having a great batch of 10 people who will always have a special place in my heart.

But it’s then when my fear of failure strikes hardest – after I’d already succeeded. Because if I’d already done it well once, now everyone (or at least so the little voice in my head tells me) is expecting me to outperform the benchmark again, and anything less than perfect would be considered a failure. Guess what? This had led me to the exact result that I dreaded – failing miserably in various 2nd-time opportunities, only because I was so nervous. It happened time and again, and luckily I learned how to avoid this trap as time went by.

This expectation that the second time should go like the first one is of course, unrealistic. Zero to 80% is actually infinite growth (I’m a math geek after all). Demonstrating that kind of growth after you are already doing quite well is practically impossible. 

My specialty as a strategic consultant and product executive coach is this complex triangle where the product meets the strategy and the business. It is especially hard to succeed there, since as a product leader, your responsibility is no longer to build a great product, but rather to build a product that would become a business success – and that’s a very different ballgame, which entails much more than the actual code released to production. One area where I see this phenomenon of unrealistic expectations in many startups is regarding the sales process of their product.

One of these places that I get to work with companies on, is how to sell their product. Despite what people think, the first sale in a startup is usually not as hard as the ones following it. In the first sale, you have nothing to lose, you are still not expecting or pushing for sales, and it is quite a pleasant surprise that what you do actually works. It’s a big milestone, for sure, but what comes next is the really hard part.

That’s when you think you already know how to sell the product (because you’ve done it once or even a number of times successfully), and you have a goal. Now things get tricky. You now have a revenue goal, usually with a much more aggressive timeline than what reality can hold (either because you think it’s going to be easier or because you just need the money, now). With that, you attack full power and try as hard as you can to sell. But it doesn’t work.

One of the reasons that it doesn’t work as well as you expected is that perhaps the first sales were based on relationships more than on the product or on a great sales process. That’s very natural and exactly how it should work. 

But another reason is that in order for your customers to buy your product they need to be ready to buy it. As leads in your pipeline, they need to be warm enough and interested enough so that when you make them an offer, they would be able to accept it. It’s not up to you, it’s up to them and their pace. You need patience, and patience is relatively rare when you work against an aggressive goal. And just the way my fear of failing the second time was a self-fulfilling prophecy, trying too hard to sell would lead to the exact opposite. I’m sure you’ve been there yourself as a customer.

So what can you do to sell your product still? Here are a few things to keep your eye on at all times.

It’s Not up to You

The key to successfully selling your product isn’t related to your product, the price, or the value. It starts much earlier – with the mindset. As the title of this article suggests, selling your product is a mindset that is bound to fail because it’s not up to you. You can’t force anything on your customer, they have to be willing to make the move. 

It could sound scary because we all like to feel in control, especially when we have an aggressive goal to meet. But once you understand it, it makes things much easier. Specifically, it allows you to understand what are the things that you need to look at, and which efforts are futile.

It also helps you to set yourself with the right point of view for this effort: the customer’s one. This point of view is so important on one hand, but so hard to stick to on the other. That’s why it takes something as significant as the fundamental understanding that it’s not up to you, to help you get back to it whenever it’s lost.

Understand Their Buying Journey

Think about the last time you bought something, ideally not a simple consumable product. What was your buying journey? When did the idea of buying this kind of product actually land in your head? How did it get there? When did you decide that you are going to buy and not just consider? When and how did you decide that you are going to buy that specific product? What did you run into throughout the buying process itself? Was it helpful or did it create any objection?

As you develop your awareness of your own journey, you’ll realize how complex it was. How many things did you have to overcome before you made a single purchase? As you can see, the journey starts way before you met the actual product that you decided to buy eventually. It involved research on the category, and then perhaps on the products themselves until you decided to make the move. 

Like you, your customers are people. They need to go through a similar journey themselves. And like you, they need to make the move themselves. Nothing can force them to do it. You can create a sense of urgency and all the tricks in the book, but still, it’s their decision to make.

There are many frameworks for buying journeys. Know-like-trust, awareness-consideration-conversion, and any other that you might find useful. Whichever framework you decide to use, use it merely as a guide, and make sure you think for yourself and understand why each step of the journey looks the way it does.

Of course, like anything else you are uncertain about, the buying journey you outline requires validation. Reach out to real people and ask them how they buy products similar to yours. It doesn’t necessarily have to be in the same category, but for example, if you are selling to DevOps managers, talk to a few and ask them how they decided to buy the last piece of software they purchased. 

Guide Them Through It

So if it’s not up to you, and it’s a complex buying journey that they need to go through, what can you do to sell more efficiently? The only thing to do is to guide them throughout this journey, so that perhaps they walk in it a bit faster than they would otherwise, or that they don’t quit once they meet obstacles along the way. 

When you understand that your job is to help them, try to anticipate what they need at each stage. For example, if they are still not sure about whether at all they need a product of this specific category (this is very common with companies that create a whole new category), send them materials about that specific question. If they want to make sure they are not making a mistake, you can add some kind of warranty or money back guarantee. 

It’s important to understand where your customers are coming from and what they need at each point in time because if you try to push them when they are not ready, it will fail. If you try to address a different concern than the one they are currently facing, it won’t work.

You see, even though you can’t control it, you can still influence it, so it’s not as scary. But it all starts with submitting to the fact that it’s not in your hands. It’s the only way to make sure you’ll make the right efforts to actually make it work.

Good luck selling! Wait, scratch that. Good luck helping your customers buy!