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4 Common Assignment Selling Mistakes (and How to Fix Them)

Assignment selling can revolutionize your sales process — but only if it's done well. Follow this guide to avoid common mistakes.

By Tom DiScipio

4 Common Assignment Selling Mistakes (and How to Fix Them)

Picture this: You’re a salesperson getting ready for a call with a prospect.

You’re anticipating any and all possible buyer questions and ready to provide articles, case studies, details, and expertise needed to answer them and ease concerns.

Then, in the call itself, just when you’re preparing to answer those same old questions, something magical happens...

There are no questions. The prospect already has the answers. Every single one.

Your prospect already has all the information they need. They already trust your business and they're eager to move forward into the next stages of the sales process.

This is assignment selling in action.

Simply put, assignment selling is the process of using educational content about your products and services to help speed up the sales process.

This content helps answer questions before they come up, making sales calls more productive and efficient.

However, like most great sales and marketing tactics, assignment selling is easy to get wrong when you're new to it.

The power of assignment selling

The theory behind assignment selling is simple: An educated prospect is more likely to become a customer — and faster.

In practice, assignment selling usually begins before a first sales call, when a salesperson sends pieces of content to the prospect to review before the call takes place.


The content is designed to answer the most pressing questions that buyers have at that stage in the sales process. Once a prospect has gone through the material, ideally, they'll be better educated and prepared for specific conversations.

With many of the standard concerns addressed through content, you can focus more on understanding that prospect's specific needs. 

On the flip side, when you share content ahead of time, bad-fit prospects may opt out of the sales process (or not complete the assignment at all). While disappointing, this saves your sales team a lot of time and effort in the long run.

Overall, assignment selling can be a sales reps’ greatest tool, but it’s all in how it’s used. 

Avoiding common assignment selling mistakes

No matter the size and makeup of the sales team, assignment selling mistakes are bound to happen as you first get started.

Just like anything else in life, you have to fall down a few times before you can dust yourself off and learn from your missteps.

These are the most common mistakes that happen when companies are first getting started with assignment selling.

Here are four common errors to avoid when getting started with assignment selling at your organization:

  1. Assigning too much or too little content
  2. Moving forward even if the prospect blatantly ignores the assignment
  3. Using only text-based content
  4. Not selecting unique content for each prospect or situation

Let's dive into each and see how you can avoid it.

1. Assigning too much or too little content

How much is too much content?


Imagine you're a prospect. If you received an email with 15 different links you were supposed to read before your call, would you do it?

You want to give each prospect enough information to have a better sales conversation, but you don't need to assign them the entire encyclopedia.

How to fix it:

I recommend two or three pieces of content ahead of each call. Any more than that and you're pushing it.  

However, you can provide more content as long as you don't assign it. Something like a buyer's guide might be lengthy, but prospects can use it as a reference material they can thumb through, reading what they'd like.

Also, explain what each piece of content is and why it's relevant (if that's not obvious from the title).

2. Moving forward if the prospect doesn't complete the assignment

So, what do you do if a prospect doesn't complete the assignment? Unfortunately this happens, and it's usually for two possible reasons.

Either they're not that serious about buying or they're too busy or forgot.

Shrugging this off and moving forward with the sales process can waste your time and the prospects. 

How to fix it:

The day before your call, respond to your prospect with a short but sincere email that stresses the importance of reviewing the material.

The email could look something like this:

Hi [prospect name],

Confirming our 2:45pm EST call today.

This is a reminder to make sure you have had time to read the resources below before we speak. If not, it may make sense to reschedule. I want to ensure we make the best use of our time together.

  • Marcus Sheridan’s free course: They Ask, You Answer Fundamentals
  • What Is a Learning Center and Why Does My Website Need One?

If you haven't had time to look at the above material, here is my calendar to book another time.

Keep me posted!


If you need to reschedule the call, so be it. If the prospect didn't complete the assignments because they are not serious, you've saved yourself the time that would have been wasted on an unqualified prospect.

If they didn't get to it, pushing back the meeting gives them the time they need to really focus and also reinforces the importance of the materials.

3. Using only text-based content


Articles are great, but many prospects prefer to consume information in different ways. This may mean podcasts, infographics, video, or even interactive tools. 

Video, with its use of audio and visuals, can actually be one the most useful tool in educating quickly and thoroughly.

In fact, when asked they’d most like to learn about a product or service, 73% of buyers said they’d prefer to watch a short video than read a blog post, view an infographic, or watch a webinar, among other things. 

Knowing this, it's a huge mistake to not incorporate other mediums, especially video, into your assignment selling materials. 

How to fix it:


Meet with your marketing team to talk about creating a wider variety of mediums. Can they help you by producing video content? Are there other types of content they can make?

Be clear with them: sales enablement materials should take different forms to suit different buyers.

You can also take matters into your own hands.

Use your smartphone or laptop camera to record a video reciting some of the insights shared in an article or use a tool like Canva to create an infographic on your own.

Canva has dozens of templates to help you turn your copy into a compelling infographic to share with your prospects without any design experience. 

4. Not selecting the right content for each buyer's stage

A prospect just getting to know your company is not in the same position as a final-stage buyer deciding between two options. Both need information from you, but their needs and mindsets are vastly different.

As a salesperson, if you blast out the same content email to every prospect, you're going to come off as generic and insincere.

You may be sending along information that is of zero interest to your prospect and, in turn, you're missing a huge opportunity to resonate with him and build trust. 

How to fix it:

Build up a library of sales enablement materials that answer as many buyer questions as possible and keep them organized by things like the stage of the buyer's journey or pain point. 

From there, whenever you send an assignment selling email, you can check your library and choose the material that is best suited to where that prospect currently is, conversations you've already had, and even the conversations you're about to. 

The right path forward


Your website and digital content are the best sales tools your reps will ever have.

Delivering that content to prospects in the form of assignment selling allows your sales teams to spend their time in the right places — closing deals, not "working" deals.

Assignment selling is the key to:

  • Better qualifying a prospect's commitment to the sales process
  • Shortening the sales cycle
  • Devoting time to more qualified leads
  • Dramatically improved close rates

Avoiding the common mistakes outlined above will help you use this process in the most effective way possible. Keep tweaking and evaluating as you go, sharpening your skills and improving your technique.

Want to dive deeper into assignment selling and how to do it right?

Take our free course "Assignment Selling: Content Is Your Greatest Sales Tool" today!

Free Assessment:

How does your inbound marketing measure up?
Take this free, 5-minute assessment and learn what you can start doing today to boost traffic, leads, and sales.


Inbound Sales
Assignment Selling
Sales Professionals
Published on March 2, 2023

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