049: Damian Thompson on sales mistakes small business owners make

Damian Thompson

Damian Thompson is founder and Chief Training Officer for Salesability, focusing on sales training for small business owners who don’t like sales. Sounds like the kind of guy we need to have on Sales for Nerds!

Damian started out selling newspapers, then did door-to-door sales in college. After college, Damian’s first “real” sales job was in enterprise software security. Then he’s help big companies set up a new sales office in foreign countries. He “burned the suit and tie” in 2011 and started trying to build his own business online. He moved to the Philippines, and started building an outsourced sales business. But it was hard. Then he did some copywriting and lead generation on demand, but was doing sales coaching to pay the bills.

Finally, he realized that he should focus on the sales coaching, with a particular attention to skilled creators who are reluctant sales people. Because they don’t like it, they don’t treat it with respect, so they never get really good about it. Their passion keeps them afloat, but they never build the sales process to grow beyond themselves, then they make the “$100,000 mistake” but hiring a savior salesperson, who then fails, because they were never setup for success. Here’s more of what Damian learned…

Damian’s definition of a real business is having revenue come in that you don’t have to touch.

Damian says there are a lot of charlatans like Grant Cardone. There’s also a lot of noise from SaaS companies like Steli Efti from Close, Aaron Ross from Predictable Revenue (see Aaron’s interviews on Sales for Nerds here and here) that doesn’t necessarily apply to the typical small business. Most sales training is run for big companies selling to other big companies.

Sales is a process– there’s no such thing as a natural born sales person. Once you take it on as a process, engineers can be great at sales.

There’s no such things as multitasking– time management is a huge problem for founders who struggle with sales.

Make sure you do prospecting every day, even when you’re busy with other stuff, or your pipeline will dry up and you’ll be in big trouble.

What you shouldn’t doing?

  • Trying to automate too much. You can’t automate empathy or insight. Mass cold email is terrible.
  • Fear the telephone. Pick up the phone (or Zoom or Skype) and call people. “Email for marketing, the phone is for selling.”
  • Charge too little. Everyone expects to be on time and on budget. Getting the first dollars is always the hardest– because they have to trust you. Note that you’re not selling your time– if you spent a lifetime learning to do something quickly, that’s valuable. It’s about the goal you help them reach.
  • Fail to sell against the status quo– by failing to establish consequences for inaction. Damien uses a personal example– I’m trying to lose 15 pounds– I know how to do it and I even tell myself that I want to do it, but I’m not doing it.
  • Skipping over the early qualification stages to try to speed to the end of the sale. Don’t ask “just enough questions to write a proposal.” Then you end up harassing the wrong prospects, and you’re constantly following up without giving any value, and you decide you hate sales.
  • Not having a system for sales. You are in control– just because someone asks you for something, doesn’t mean you have to give it to them. Don’t be not in control. Don’t let your prospects bully you.
  • Taking time with the wrong prospects. These people are happy to waste your time.
  • Not setting up sales reps for success. Typically when business owners hire operational help, they know how to do the process they’re hiring someone to do. But in sales, they don’t have a process, so they hope that a magical sales person will fix everything, but they’re not set up for success.

You have to “go the gym” every day. Your personal trainer can’t work out for you. You have to spend time on sales.

And you have to ask decisively for the next step. For example, you ask a web lead for a 20 minute call. But what happens at the end of that call? Is it a proposal? If so, do a live proposal review and schedule it on the call. Then what happens when you present? You ask for the business. Sometimes they say yes, sometimes they say no, but have a decisive next step for the “I have to think about” people.

Always ask for a meeting until you get a yes or no. If someone isn’t willing to get on a call with you, will they give you thousands of dollars? There’s nothing you can do with sales skills to sell something to someone who won’t get on the phone with you for a few minutes.

The person who wins is usually the most honest. So if you feel like you’re getting brushed off, make sure they have permission to say “no” without hurting your feelings. (And then ask what you could have done differently.)

Here’s the question to ask: one a scale of 1 to 10, and you can’t say 7, how big a problem is this? If they say a 6 or below, it’s not worth pursuing. If they say 8, 9, or 10, ask for more information on why.

Now go PICK UP THE *$@& PHONE!!! Or Zoom or whatever. (Here are some tips on doing video calls— especially important since face to face meeting are off the menu for now.)

The Wine

I got to enjoy some Chateau Fongaban Bordeaux from Puisseguin-Saint-Emilion. (In the episode, I mistakenly pronounced, or tried to pronounce it with an ‘R’ instead of an ‘F’ and the beginning– you can look at the label and decide if that’s a reasonable mistake.)

Where to find Damian…


Where you can find Reuben: @Sales4Nerds, @Mimiran, Mimiran.com (the easy CRM for people who are awesome at serving clients and would love some help getting more, but hate “selling”). You can also  listen on Overcast, or Subscribe on Android, or Player.fm.

Also, if you can get a free “fill in the blank” hero proposal template. Remember, a proposal is a story, not a brochure.

If you’ve ever struggled with a proposal, check out the “official” Sales for Nerds online course on Sales Proposals the Right Way (coupon link for listeners).

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Published by

Reuben Swartz

Host and Chief Nerd.