Getting over the fear of selling as a founder
No amount of education, work experience, or podcasts can prepare you for being a founder. Inevitably you will have a lot of “firsts.”
Many of the things you can outsource or delegate. These tend to be general business activities like accounting, bookkeeping, or drafting legal documents and are not what makes your business unique (a.k.a your “secret sauce”).
But there are some activities that founders should never outsource or delegate until they can nail them first. One of them is sales.
For me, that was a problem when starting Prodsight. I’m an introvert, and speaking to strangers is an uphill battle I have been fighting for as long as I remember.
Building up the motivation to sell
Going through school and university might be possible without overcoming the fear of selling. Heck, you might even manage most jobs. But I don’t think you can succeed as a founder without getting comfortable with selling.
It might be tempting to think that if your product is self-service and you are pursuing a Product-led Growth (PLG) model, you don’t need to learn to sell. Users will sign up, input their credit card details, and voila!
But even if you can make that work, that’s only half of the puzzle with product sales. You also need to think about selling your company. Whether selling to potential investors, employees, co-founders, partners, media or being on a podcast - that’s all part of the same skillset.
Being able to sell your product and your company is essential.
As a founder, I was the ambassador of my startup, and I realized that unless I get over the hump, I won’t be able to move my company forward.
Once I made that realization, the motivation was clear. I needed to learn to sell. I needed to get good at it.
Overcoming the fear of selling
The fear of selling my product and my company came down to my lack of confidence. I was not confident our product was strong enough when pitching potential customers. I was not confident my background was impressive enough when pitching investors. I was not confident in my skill to handle a conversation where the objective was to have the other party buy something from me. And the biggest of all, I was scared of rejection.
So how did I build up the confidence to sell despite self-doubt? How did I grow a thick skin to be immune to rejections?
The reality is that I didn’t—at least not all the way. I just got good enough to be effective. Good enough to close early customers, raise investment, and eventually even sell the company. I think of salesmanship as a lifelong skill that can be visualized on a spectrum. I moved from the “Absolutely paralyzed” stage to the “Selling stuff” stage.
Focusing on the problem instead of the solution
In my head, sales were Shelley Levene from Glengarry Glen Ross (1992) desperately trying to sell stuff people don’t want… and failing.
In my first few sales demo calls, I would immediately jump into sharing my screen and describing every feature of our product. I would do 90% of the talking and walk away with no idea of what the prospect thought of the product, let alone whether or not they even had the problem we were solving. The outcome of each call was binary.
It wasn’t working, and it was everything I feared sales would be like.
Then after some deep reflection, I shifted my approach. Instead of doing a hard sell, I would focus on the customer’s problem instead.
I started every sales conversation by understanding the customer. What is their business? What is their role and day-to-day look like? What challenges are they facing on the day-to-day? I became a researcher. The prospect was doing most of the talking.
I would talk about our solution only when and if I genuinely understood if we could solve this customer’s problem.
I started actually enjoying these conversations. I even reached the point of looking forward to doing sales calls.
Every customer conversation became a learning opportunity. It was no longer about just winning the sale or dodging a rejection. It was about advancing my understanding of the market, customer profiles, alternative solutions, and sales objections - all of which I would analyze and feed right back into our strategy.
And it had an impact on the conversion rates as well. Prospects became more comfortable speaking with me. They were no longer on defense, trying to dodge my sales tactics. We were having a genuine conversation to see if we could help each other. And if not, we would part ways amicably without any hurt feelings, having still benefited from talking to each other.
Growing confidence through practice
Confidence is not something you are either born with or not. It’s something that you can grow over time. It’s also something that you can lose and might need to rebuild.
As I practiced selling, I naturally got better over time. As I closed deals, I gained confidence in our product's value and my ability to connect customers’ needs to our solution and get it over the line.
With each conversation, I would better predict customer questions and develop better answers to common objections. I built up a bank of customer stories that I could quickly recall and use in the conversations helping me to build trust.
As I became more fluent in sales, I naturally came across as more confident, which impacted the prospects. People are good at picking up on various cues, and if you come across them confidently, they are more willing to trust you and buy from you.
Closing thoughts
Overcoming the fear of selling was one of the hardest things I had to do as part of my founder’s journey. But it wasn’t just a grueling task I had to endure only to reach the destination. It became a lifelong skill that I will use for years in my work and personal life.
If you are a founder struggling with the fear of sales, I highly encourage you to attack it head-on. You will be a better founder once you get over the hump.