All Of My Selling Mistakes (How to Sell Part 2)

how to make sales

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Note: This is a post from 2016.

So, if you don’t know how to sell your services, you don’t have a coaching business.

But selling – for most of us – is SO HARD.

I wrote a blog on how to get past some of your fears and doubts around selling (definitely read it here), and as a part two on this series I want to talk about some of my selling mistakes.

The truth is, I’ve sold a lot.  I’ve sold retreats, my book, big group coaching programs, small group coaching programs, DIY online coaching programs, and more expensive one-on-one services.  I’ve sold things that cost $35 and things that cost $6,000. But even though I’ve sold hundreds and hundreds of thousands of dollars of products and services – I’ve still made PLENTY of mistakes … almost every day.

So…in no particular order, here’s a peek behind the scenes at my business.

Selling Mistake 1: Forgetting the education

One of the things I love about being my own boss is creating interesting and helpful products.  I knew that networking is crucial to passion and career success, so year and a half ago I outlined a quick online live workshop I called the Networking Masterclass.

I knew my people needed networking help, but I wasn’t sure it THEY knew  they needed it.  So, instead of spending hours creating a big program and recording a bunch of video etc etc,  I threw up a sales page offering a two-hour live webinar, emailed my community, and set an incredibly low price.  I wanted to see if I could get paid to build it. $7,000 later, I had my answer.

It was great – I earned $7,000 to build a program, and I got confirmation I was on the right track…all for a few hours work.  Yay!

Feeling my oats, I took the program and turned it into a monster offering, with a private portal, hours of video, branded worksheets, the works.

I spent a few months working on it behind the scenes, getting it ready, polishing it up.

I felt great – I knew people needed it, I knew people would buy it, and now I had created something that would provide a ton of passive income for me because I had taken the live component out of the program. Now, all I had to do was sell it and I’d be helping people in my sleep.

So, I set a price of $197, threw up a much more detailed sales page, planned the launch, and pulled the trigger.

The first day of the launch was great – one of my best first days ever in terms of number of sales.

I was giddy with success – 50-75% of your sales usually come in on the last day something is available, so I thought this program was going to blow through my expectations and do amazingly well.

The second day was also good.

The third day NO ONE bought the program.

The fourth day two people bought.

The final day had a lot of sales, but NOTHING like what I had been expecting.

I had thought this program would make between $30,000- $40,000 on the initial launch (and I’d be able to keep selling it forever after), but instead it did $15,000. Half of what I had expected.


I had forgotten to educate people on why this program was so important. 

Before I offered the program I had sent several emails to my community about networking – but I was swayed by some of the questions I was getting in response, and instead of educating them on how building a strong network can literally change your career trajectory (and provide you with a career safety net), I ended up taking time to answer some of their more common questions in detail.

Therein lies the problem – the people who got their questions answered weren’t motivated to buy the program, and the rest of my community didn’t have a strong enough case on why this skill is so life-changing.

*face palm*

You guys, I know better! And yet, I still made the mistake. No matter how skilled you get, sales mistakes happen to ALL of us.

Keep reading for the aftermath.

Awkward selling mistakes that cost you money (don't do this!)

The aftermath

So, I had a great program, I had great client results from the launch (all kinds of good networking success). Now what to do?

I dusted myself off and changed tracks. In the next iteration of the program launch I took into account the education piece and spent significant amounts of time talking about it.  I explained all of the many reasons why networking is important, and then I started to teach a little bit more about the networking skill set before I offered the program for sale.


Tons more sales. Voila!

Never forget to educate people about why what you do is so amazing…for them.

Sales mistake #2: Not matching the touch to the price

I have a love and hate relationship with retreats. I LOVE them because for me they are one of the most fun and impactful ways to do what we, as coaches, do. Getting your hands on someone in a real and personal way (in a beautiful location), and helping to change their life is worth waking up for.

But I sometimes hate retreats because selling them can be a massive energy drain if you don’t do it right.

I was gearing up for my second big retreat, and I had a science-project mentality about marketing it. I was willing to try out a few things and see what stuck. The reason?  I’d changed the mission and focus of the retreat so it was basically a new offering for me.

Truthfully, I was worried.

Retreats can be a hard sell because it’s not just the price of the ticket, it’s also the price of the flight, hotel, rental car etc that people have to take into account, and the more things cost, the more people hold back.

I knew if I didn’t have the right message, if I was a little bit off, I could easily miss out on sales and have people miss out on the help they needed.

So, with that in mind I tweaked my message, I came up with a big launch plan, I enlisted help, and I rolled the dice a little bit.  I created a huge “retreat-like” experience online, and I had 2,000 new people sign up to participate.

At the end of that experience, I offered the full retreat for sale and …

…2 sales came in immediately.

Then 2 more.



I spent weeks planning this huge free experience, everyone seemed to love it and …

4 sales?


I poured a glass of wine, then had another, then thought about what went wrong.

Can you guess?

When I sold the retreat in the past, I sold it from a phone call. Why? Because it was a BIG expense for people, and they needed to feel connected to me in person in order to feel good about coming to the retreat.

If I wanted to get more people to attend, I had to offer them more chances to connect with me and get to know me, and ideally in a way that felt more personal.  Because if there’s any rule of sales it’s this: The more expensive the product or service, the more personal the sales process.

If people are paying thousands of dollars for you, then they want to talk to YOU.

So, I dusted off my back up plan: I brought my introductory 45 minute long private coaching session out of retirement, and offered it for $100 for 3 days to a small section of my community who had previously shown the most interest in the retreat (the powers of email tracking!).

I sold more of them than I expected or really wanted, so I turned off my sales cart early, and voila: Now I had a motivated interest list of people who were paying to talk with me.

I delivered my 45 minute session and then told them each about the retreat.



Folks were spending a few thousand dollars all-in to attend this event, and they needed more of  a relationship with ME.

And because it was a new offering, I needed to give more of me to reassure them that it was worth their time and money.

The aftermath

I was able to get more people to sign up right away on the phone and hit my base sales goal for the event. They just needed that extra personal touch to go with the higher price tag.  It’s such a silly mistake on my part because I know this, and yet – I’m human :).

Whew! This is a long post. I’m tired, are you tired?

However, I love this stuff so I could go on…and on :). So, if you want more mistakes from when I first started coaching to, well, yesterday, shout out in the comments!

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