How Do I Train My Sales Force?

I was oehinking the other day how little time I spend in my posts on the very thing that I have done the last 24 years – training a business-to-business sales force. This post gives you suggestions to get started, whether you hire someone from the outside (like me), or not.

The Myths of Sales Training

There are several that need to be debunked first. In no order, here they are:

1. Full Day Programs Are Useful. They are not. Wow. There, I said it. And I actually do one-day programs, mainly to launch a more comprehensive program. But I find that sitting in a room for 8 hours consuming a trainers content is not how adults learn.

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Are You an Amateur or a Pro? Here is a Simple Checklist

I’ve been reading a lot of Steven Pressfield lately. He’s written a couple of books that are really good – namely “Turning Pro” and “The War of Art.”


If you’re a client of mine, I’ve probably sent you one of those books to help you grow your business. If you’re not a client, then I urge you to go to Amazon and purchase them both immediately, especially if you are interested in creating a new future for your business.

Most of the readers of my blog are sales or business development people and I thought I would create a very simple five-point checklist to help you assess whether you’re an amateur or a pro (or whether you have amateurs or pros working for you):

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What Skills I Would Insist On If I Were Your Sales Manager

I was asked recently what skills I would look for in a sales person. That got me thinking of “who” I would hire if I had to hire bunches of sales people. Here is my list of skills:

1. Understanding of Email Marketing

“Why” you say? Easy. Email is the most underused tool you have. How you write subject lines matters. How you craft a sales email matters. How you invite people into your tribe matters. How you share your expertise matters. All can be done via email. Learn – an autorespond service that helps you drip on your prospects.

2. WordPress Chops

Yes, I would want you to learn WordPress. Ever heard of it? Didn’t think so. Learn it. Go to and watch some videos on how to use it. It is a blogging platform that helps you establish your expertise by writing pertinent, valuable articles for your tribe (prospects.) It gives you a publishing tool right at your fingertips. $200 and you’re a publisher. You can then send your prospects to your blog where you will share great stuff.

3. Video Production Skills

You can always hire this out, but in my org, every sales person needs to know how to produce solid video (put on your blog). Interview clients…happy ones, presumably. Put it online. Have your own vignettes that you produce on trends in the industry. Take a class on video editing. It’ll take you no more than a couple of hours to figure it out. You can even do all of this with your iPhone. No need for thousand dollar cameras. So….no excuses.

4. Social Media Talent

LinkedIn, Facebook, Twitter…yes all the usual suspects. But do you know how to REALLY use them? You will as part of my team. Plenty of great sources online to learn how to maximize your use of this avenue. This is especially good for inside sales, but works for all. If you haven’t read a book on how to use LinkedIn, stop what you’re doing right now and read one. Oh, that’s right, you’re not on my team yet. Read it anyway.

5. Diagnosing Beats Selling – Everyday

Get good at diagnosing problems. The more problems you find (at your prospect) the more you’ll sell. Stop selling and start solving. Take a class on analysis. Make a list of the problems you solve and go find those problems. Most sales people stop before they make that list.

6. Writing Chops

I know, I’ve use the word “chops” too many times already. But, you get the idea. Most people are disgusted at composing and writing but not you. You’ll take an online class in it. And just write. Even if you can’t. Write and rewrite. It’s how you’ll get noticed (on Google ) and how you’ll populate your blog. A person who can craft their thoughts on paper is the same person who will be skilled at communicating their message verbally.

7. Storytelling

I paraphrase but Rolf Jensen, The Dream Society, said “Story telling is the #1 skill for the fu

ture.” He was much more eloquent than that but being able to tell your story – and your company’s story – is vital in differentiating yourself from all others. Nothing connects with your buyers quite like a good story. Tell them how you got where you are. What mountains and valleys you’ve traversed. Give them a peak inside yourself. That’s something they won’t forget – unlike your features and benefits.

8. Project Planning

Every thing you do on my sales team will be a “Project.” Your goals. Your territory plan. Your key account targeting. Most sales people are woeful at project planning. If you’re lousy at it, go hire someone at $50/hour to spend 4 hours with you and plan your major projects. Then, time activate it and watch great things happen. (I would prefer you spend time here rather than on goal setting. Anyone can set goals. Not anyone can create the plan to accomplish them.

9. Idea Capture

As you’re doing your job, you will have ideas. Make sure you have a place to capture them. It could be a folder (physical) or a Notes on your phone. We live in an ‘idea society.’ And sales is a place where ideas come fast. But most fail to capture them…and miss the rewards from them. Your brain is an idea machine. Don’t fail it by letting them slip.

10. Productive Habits

We have a problem now – too much information coming in. too many things you could work on. you can’t do it all-and shouldn’t. So you must have a “system” for producing results. A system for handling prospects. System for handling inbound communication. System for following up with people who owe you actions. David Allen (Getting Things Done) has some magical stuff here. Go watch some YT videos of him. But you need to be productive if you’re to be on my team.


So that’s it. Not bad, huh? I didn’t say anything about closing skills, probing skills, handling objections or any of that stuff. Yes, it’s important, but if you do the things above correctly, opportunities will flow to you – and you’ll be able to select who you want to work with. And if they don’t behave properly, cut them and move on.



How to Train Your Sales Team

As sales development specialists, we get asked all the time “how” we go about training a sales team. We’d like to think there is some secret sauce we  have access to, but we begin most engagements the same way – by understanding the 9 points in this video.

If you’re exploring ways for Caskey to help you grow your business by developing the skills of your team, then this video shares our philosophy and how we go about the work. It’s divided into two section:

  1. GET READY, which is the upfront discussions you must have internally, and
  2. GET RESULTS, which is the implementation of the work itself.