I used to suck at sales. So this is what I did to fix it

7 practical steps to get you selling more

If you suck at sales I can relate.

That used to be me. I was shy, hated calling people (still kind of do), hated getting rejected and couldn’t land a sale.

How I used to view sales

I remember watching The Wolf of Wall Street with Jordan Belfort selling a blue pen and was like, "There is no way I would ever in my life do that.

I associated sales with being sleazy, annoying, and lame. I’m a numbers person so preferred doing my own thing and coding.

I had a deep fear of rejection and not wanting to look stupid and sales was the surest way to probe on that fear. (I mean who really enjoys getting rejected?)

But then, I started a software company and I had no other choice.

Whoops…

Turns out you have to sell when you have a company.

Well, burning your boats is one way to do it so here’s how I approached it.

Breaking down the problem

• I decided that I would approach sales like a science experiment, reading as many things as I could and then trying to log what worked and what didn’t.

• I focused on input goals through this process (number of calls) as opposed to output goals (number of conversions.)

I thought I would break down the 7 key things that have helped me.

Lesson 1 - Read at least 10 books

Read sales books and write the tips and tricks down in a notebook. I ordered hundreds of dollars worth of books and still do to this day.

I think you should read 10 books. That way you will find out ones that you like and ones that you hate. For example in that list above, I randomly enjoyed Zig Ziglar’s book a lot and hated the greatest salesman in the world.

You have to triangulate what works well for you.

I do believe that everyone has a unique style of selling and you ultimately have to play to your unique strengths.

Lesson 2 - Write

If you’re thinking without writing, you only think you’re thinking.

Leslie Lamport

I only read that quote 3 months ago and what a game changer it has been. I wish I had written from the beginning.

What should you write about?

• Anything that comes to mind. It doesn’t have to strictly be around sales, it could be with how you are feeling, your goals and your dreams.

• Always write your book reviews and key takeaways.

I’ve found since writing I remember things and work through problems in a much clearer way and this has a carry over effect to helping with my business.

Lesson 3 - If you think it is hard to sell you should remember how hard it is to buy something

When you start out, you are so focused on how YOU feel and how hard selling is FOR YOU.

Flip it around. Have empathy with your buyer.

Go out and buy something really annoying and hard and observe how you feel. Heck sometimes going to a clothing shop is enough to feel completely overwhelmed.

Now I sell software and this exercise really helped to open my eyes to what my customers were feeling. If I struggled to buy clothes - which is something that I understand, then no wonder they struggled to buy software - it’s so confusing!

So slow down, don’t even think about yourself here, just take each call with a posture of remembering how hard it is to buy something.

Once you do that, everything becomes easier. You have more empathy, you don’t get grumpy, these people aren’t being mean to you, buying thing’s is just really difficult.

Lesson 4 - Now that you know the above - hyper fixate on solving one specific problem for one specific customer

Do you want to know a life hack that I have found in sales that particularly works when you are starting out?

Hyper focus on your customer and just guess what their problems are and do all you can to solve them before the sale.

This is particularly important when you are starting out with your business and don’t have any credibility.

So what you do is, put yourself in their shoes, try and solve their problem or anticipate what their needs are (helps if you have spoken to them beforehand) and then solve all of this before the call. Yes this is more work, yes this isn’t scalable.

But go and read this post here that I did on the power of your time as leverage as a founder when you are starting out and how hard it is for other businesses to replicate this.

I still use this trick to this day.

• Instead of trying to sell someone some random idea, I just build the idea and then show them.

• So that means making prototypes, articles, reports and documents. Whatever the client needs to see and taste what you are selling them.

So using my software company as an example.

Instead of telling our client the benefit of AI, we will create a prototype of a use case that could help them and just show them that in a presentation.

For example, I had a commercial real estate company that wanted to do work. They wanted a financial integration to a system. So I created a dummy spreadsheet and then a prototype of the tool (all without being asked to) and presented that to them.

The sales presentations with a prototype are markedly easier. It shift’s the conversations away from my company and background and purely to the problem and pain point.

• Now we will do 100 page presentations filled with prototypes and all sorts of use cases.

• We will build entire websites and UIs all as part of the pitch.

Is this scalable? No! Absolutely not! Is it effective? Yes! So we make sure to only do this for client’s that we think will have an outsized strategic return. To help with this, I have made a consulting pricing framework which you can view here.

Lesson 5 - 85% of deals end in no decision!

It’s not you, it’s the client.

Specifically, it’s the law of omission. Most people would rather do nothing, than make the wrong decision. Remember buying is hard! So most deals are lost to no decision.

I only learned about this statistic recently and man I wished I had read about it earlier. I would have stopped beating myself up when people ghosted me.

The weird thing is (that I still haven’t gotten used to) people often don’t say no. They will say all sorts of things that aren’t yes.

They will ghost you.

Not reply to you.

Still to this day, 5 years in, I still get upset and frustrated at a few people that promised me sales, said we had the job and ghosted me.

But you are only human and rejection does suck. That’s why it helps, having an analytical mindset to this and focus on input goals.

Unfortunately sales is a numbers game. You just have to find ways to increase the number of conversations that you have.

Lesson 6 - Think “what insight can I bring to the table”

I read a saying in the Challenger Sale Book that customers are looking for you to bring insights to the table and help them to think differently about their own business.

So what this looks like in practice.

• If I’m pitching on a SEO job, I’ll review the customer’s website. Tell them the things they need to work on and then show them something that Apple does that they could implement.

• I aim high on the intellectual curve here, so I like to get facts and information that is fresh and that a CEO is likely to have not heard before.

• Writing helps a lot with this. If you are constantly writing interesting things, then you will have interesting things to say at the meeting.

One trick to bringing insights to the table is casting forward. When I sell AI, I often zoom out and talk about what 2030 will be like and then work backwards.

Client’s enjoy it as they like to see where the trends are going and it is typically not something they have heard before.

Lesson 7 - Read Founding Sales

The book that helped me the most was founding sales. It has a lot of practical steps and it’s even free if you go to the website.

https://www.foundingsales.com/

I love it because it has all sorts of practical tips and tricks (like email templates - rejection handling.)

It’s the book that also changed my mindset on sales and helped me to feel comfortable with rejection.

If you enjoyed this article then head on over to my blog at https://www.cubthinktank.com/ where I deep dive into resources that can help you be a better executive or entrepreneur.