How to overcome the fear of selling

Sales is hard, even for experienced folks.

Requires a lot of thought, practice, and time to get really good at it.

Which makes it a very daunting task for founders who are selling for the first time.

Sales is a series of processes, systems, and skills. All of which can be learned.

But a lot of founders struggle with sales. Not because they can’t learn how to do it.

But because of a crippling factor. Fear.

In today’s newsletter, we’ll dig a bit deeper into sales mindset, why it’s so hard to get started with sales, and what to do about it.

Table of Contents

• Why is sales so scary as a founder?

• Outcomes are datapoints. Not your identity.

• With sales, you’re in the rejection game.

• How to bust through fear

Why is sales so scary as a founder?

When you’re a founder, working on a product, you’ve built your identity around it.

You might have been an engineer. Maybe someone technical.

You saw a problem that you thought you could solve better than anyone else.

You built an MVP. Got feedback from friendlies.

Improved your MVP, got more feedback. Maybe created a website. Maybe two or three versions of it.

You’re a builder. That’s your identity.

Now it’s time to get customers and make money.

And it’s hard for you to break out of your builder identity.

Why is that?

Because the very act of doing sales means you’ll get rejected.

And rejection puts your identity at risk.

See up until now, you haven’t yet succeeded or failed. You’re in building mode.

As soon as you start getting customers, you will start getting rejections. And rejections can often feel like failure.

So for a lot of founders, they delay rejection for as long as possible. Because they attach a rejection to an outcome. And this is where the fear really comes from.

Outcomes are datapoints. Not your identity.

I once had a sales rep on my team that attached so much self-worth to his ability to hit quota, that it impacted everything in his life.

When we was hitting a target, his ego went up. People were beneath him. It was not pleasant to see.

But when he missed his quota? He was a bad husband. He was a bad parent. He couldn’t provide.

The problem is he attached his identity to an outcome. Which meant that if the outcome wasn’t achieved, he immediately saw himself as a failure, in everything.

Most information you’ll see on the internet about sales is to book meetings. Create opportunities. Close deals. Hit a revenue number. Hit quota. Etc.

The problem is that outcomes is simply datapoints. A snapshot in time, telling you how well your process operated over the previous months.

Scientists understand this really well. They focus on running the experiment. The outcome is the outcome.

When you focus on the outcome instead of getting better at running the process, then fear comes in.

With sales, you’re in the rejection game.

A good win rate in sales is 30%. When you get started, you’ll likely hover around 10-15%.

A good response rate to your outreach is 3-5%. A good positive reply rate is 1/3.

That means that the vast majority of what you’ll do in sales will result in rejection. Folks saying no to you, or even worse, just completely ignoring you in the first place.

But the 30% who’ll eventually say yes? It will feel good.

And your job is to figure out the skills you need to develop + the processes you need to put in place to get from 0-30% win rate, as consistently as possible over time.

And that’s the real focus.

The best sales reps I know - and the best founders who do sales - obsess about the process.

They obsess about how they execute a task. They get as good as possible in every aspect of discovery, demos, follow-ups.

They pay attention to what leads to a positive outcome, and what leads to a negative outcome.

Then they try to replicate the positive ones, over and over again. Until it becomes systematic.

Their identity is closer to an engineer building a system. Not a sales rep hitting quota.

And it makes a world of a difference.

How to bust through fear

I’m not a natural seller. It requires a lot of effort for me to do sales. Always has.

I’ve been knocked down 3 pegs before. And it hurts.

But here are things that have worked for me, my sales reps, and founders I’ve helped to get rid of the fear of selling (or at least learn how to work with it:

• Define a minimum task you can do. This comes from Atomic Habits by James Clear. What’s something so small, that you can do every day, that you’d be really disappointed if you didn’t do it? For me it’s sending connection requests on LinkedIn. At a bare minimum, I can send connection requests to prospects. And I can do that 20 times a day. No effort required. Easy task. I’d be coming up with a lot of excuses if it didn’t happen. It’s the easiest thing I can do. For some of the sales reps I coached, it was doing a single dial. That’s easy. For some founders I’ve coached, it was sending 5 emails. That’s easy. Break down a task to a small number that you can commit to doing every day.

• With sales, you need to be indifferent. When you reach out to someone with the idea of generating an outcome, two things happen. 1. You’re going to come across as pesky, because the outreach is about you and not them. 2. You’ll start getting fear of rejection, because you’re going in with an ask. And if they say no, it will sting. So detach from the outcome. You need to be indifferent to a yes or no (easier said than done, I understand).

• Re-define what sales is. Sales isn’t about selling your solution. That’s an outcome. Sales is about helping someone who has a big problem impacting their business make a buying decisions. When you go in with the lens of understanding their pain, then helping them come up with ways to solve their pain, sales feels a lot different. It starts feeling a lot more like product management, which might be something you’re more familiar with.

• Reflect often. It’s easy to focus on the outcomes, especially when it’s not what you want. But take time to reflect on your skills and process. And notice the good that’s happening. You went from doing 5 outreaches a week to 20 outreaches a day, consistently? That’s something to celebrate. The amount of behaviour change, processes, and upskilling that needed to be deployed to make that happen is amazing! Recognize that, and keep track of it somewhere.

• Prepare. Do research on your prospect before you hop on a demo. Take sales courses, work with a coach. Practice your pitch with friends. Brainstorm problems with your colleagues. Reach out to practice leads to get rid of the jitters before reaching out to ICP leads. Apply frameworks to your deals. When you have these in your back pocket, you feel more ready. And feeling ready to do sales is a step towards doing sales.

When you’re first getting into sales, focus more on the behaviour changes you’re implementing every day. You’ll notice you’ll get more comfortable with everything over time. Some stuff will still be daunting, it always is. But breaking past the outcome, and detaching from it, will really help.

Growing a business is really about understanding a key set of processes that come together. So everything you do, from product development to outreach to closing deals to paying employees, has a process. That’s what you’re figuring out.

The outcomes will be there as your processes get better. So focus on making your processes better every day.

Let me know what you think of the newsletter! Always want to cover topics that you care about.

For more practical early-stage sales tips, connect with me on LinkedIn.

If you’re looking for more hands-on help implementing your first sales process, reach out for coaching packages.

P.S. Starting the waitlist for next group coaching. Ping me if interested.

P.P.S I have capacity for 2-3 1:1 coaching clients right now. Fast-paced learning, meeting every week + review your sales call. For founders who are very serious about learning sales fast. LMK if interested.