How I Overcame My Fear Of #Selling

How I Overcame My Fear Of #Selling

I used to think that selling was a skill you were born with.

In fact, I always attributed my lack of ability to convert a prospect into a sale to my genetic, passive nature and my tech brain.

I was wrong!

Over the past 25 years I spent much of my time in management and technology related roles solving problems.  Developing the ability to solve problems is counter-intuitive to developing selling skills.

If you are an engineer, manager, director or VP (especially in IT) you don’t have to sell much of anything to anybody.  What you do in most of these roles is technically solve issues, which does not require selling.

My first experience and failure in sales was back in 1997 when I joined a consulting tech startup company in Fort Lauderdale, FL.  (Shout out to Solayre Media if you are still out there)  We were selling MapInfo solutions to a variety of South Florida corporations. I went into the role for a few months and basically never closed a sale.

I blamed myself for just not being a good salesmen.  In my defense we had a crappy product and a competitor called MapQuest crushed our market.  Let’s just say I never asked for a sale. I left with a bad taste in my mouth and a lesson.

I decided that sales was not for me.  I was destined to not be in sales, and I felt that sales was somewhat demoralizing.  That’s because it requires thick skin and often lots of attempts before you succeed.

I generally felt that sales sucked!

From that point forward I went into more technical, management and marketing roles, where I felt it would be a better fit for my personality.

But always lurking in the back of my mind has been the fact that I really do want to sell.  Though I knew I was a failure at it!

10 years later I developed a sophisticated software solution that powered several national event companies.  That solution is called Take It National. I wanted additional customers so I started to make sales calls and I set up a few sales meetings.

My wife came along with me on one of those Take It National sales meetings.  I thought I did well.  She is an expert at selling.  She said nothing during the meeting. Afterwards she looked at me and said “That was the worst sales call I have ever been on”.  She pointed out that I never got the contract out of my briefcase and I never asked for the sale!  I talked about everything but the sale.

Too much product talk is apparently a distraction when closing the sale I learned.

This lead me deeper into my fear of sales.  I never closed a deal for Take It National other than the basic clients it was built for, which is Pre-Dating Speed Dating.

It was not that my software package was flawed.  In fact it is quite a killer solution. It was not that it was hard to implement or difficult to understand.  It was and still is quite a good Saas application.

My wife pointed out you always have to ask for the sale and have a contract ready to be signed at the meeting or on the phone!

My wife was brutally honest, pointing out every mistake I made. I fell even deeper into my fear of sales.

Over the next year or two I ended up in a new business development role. This was going deeper into sales not away from it!  That means I went on sales calls, many sales calls selling high end web development.

The good news is I relied on my team members to be the closer.  I just brought in the leads and handed them off.  I became an amazing lead gen guy.

Meanwhile I was going deeper into the path of sales with my career, even though I felt I sucked at it.  The team did close a few projects I brought it, here and there.  It was not my sale though.  I still feared the sales process.

We attempted to raise capital for a startup at the same time.  As part of the startup process I went around and gave pitches.  Once again we did not raise the capital we required.  I was feeling like my ability to sell was pretty flawed!

Finally, when we founded StartupPOP, our startup marketing agency, which does business plans and small eCommerce and brochure websites for small to medium sized companies,  I faced a major dilemma.  I had to sell or I would be out of business!  To be in a “consulting” business you have to get contracts signed and checks in the door!

I was a 49 year old sales rookie trying out for the major leagues!

I had never really understood that selling is a critical part of our working lives.

We can’t hide from sales.

We have to sell our products and services.

We have to sell our ideas.

We have to sell ourselves as employees.

We have to sell investors when raising capital.

We have to sell people all around us the idea that we are better and deserve more because…we really deserve more.  If you just asked for it!

Working a job at a big corporation temporarily shields those of us who don’t want to face up to the fact that we will need to sell ourselves.  (If you read my other posts, I get into how I have never got a job from a job interview.  Let’s chalk that up to my inability to sell myself).

So faced with not being able to pay the bills, needing to make my startup agency work financially, I have had to buy into the concept I can sell.  Yes I can!  In fact, I have.  Ok, I have closed a dozen jobs or so.  Not that much actually.  But it is something for me personally that is a major breakthrough!

What I have found is that anybody can sell.  You just have to ask for the sale! And I have discovered that it really is a numbers game.  Sometimes you have to fail 9 times to succeed 1 time or fail 99 times to succeed 1 time. There is a formula to selling and volume can change your success.

Never Sell With Your Own Wallet!

My favorite quote from my wife is “never sell with your own wallet”.  It means you can not take the customer’s perspective.  If you do, you end up either convincing them not to buy or end up with a lower sales price.

Why should you never sell with yourself as the buyer?

Because if you put yourself in the shoes of the customer, you probably don’t want to buy what you are selling!  But this does not matter!  You can’t think like that! You are not the customer!  You need to close the deal!

So, faced with all of this, when I got the first contract for StartupPOP in front of a client to sign, the client did not know I was a rookie.  In fact he thought I have been doing this all my life.  I found out that selling is a facade.  You just need to appear to be the sales expert.  Beside, what does that require other than the ability to ask for it!

If you feel like I did that you suck at selling, you are probably right!  But, that does not mean you will suck at it in the future.  You can easily overcome some of the issues I did by simply following step by step the process of asking for a sale. And you will be surprised like I was, that people will sign your contract and let you close them eventually…

So it is true.  Always be closing.

Always be prepared to close and take a check, a credit card or Paypal payment. Don’t go to a sales meeting without a contract ready to be signed and the ability to be paid!  Ask for the sale.  There often is no second chance. You can always give the money back if you don’t produce.  But you will never succeed if you don’t ask.

You may think poorly of me, that it took me a lifetime to figure out how to simply ask for a sale, but I know many people who have yet to sell anybody anything in their careers.

We are entering a new world order where many of us will not work at large corporations ever again.  Most tech workers in the future will be independent consultants, free-lancers, oDeskers and Thumbtacks!  We need to get ourselves ready for this world and selling is the critical ingredient required to succeed!

To hire StartupPOP to develop your business plan or small eCommerce or brochure website please email me at [email protected].

By the way, just want to mention that we are running a startup pitch event in Boca Raton, Florida on Dec 8 where 10 startup companies get up and pitch their startup. Here is the info:

Have a great day and start preparing to sell in your near future!

[This post was originally posted in Linkedin as, but as far as I can see Linkedin does not let Linkedin Posts get indexed by Google, so repost them here.]

Dan Gudema
[email protected]