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4 Most Costly Rookie Assignment Selling Mistakes (and How to Fix Them)

It’s okay to be a rookie and make mistakes with assignment selling. Most people do. Plus, you're already on the right track if you're creating content for use in the sales process.

By Eric Dunn

Eric Dunn also recommends this free course: Fundamentals of Virtual Selling.

4 Most Costly Rookie Assignment Selling Mistakes (and How to Fix Them) Blog Feature

We have all experienced the growing pains of being a rookie.

Whether it was the time we started a job at a new company, picked up a new hobby, played a sport or instrument for the first time, or trained for a marathon, all of us have made rookie mistakes. 

In Jeffrey Gitomer’s book, The Little Red Book of Selling, he describes 18.5 principles, strategies, and actions that will lead any sales person to success. Number 12 on that list is “make mistakes.” 

"Make mistakes. The best teacher is failure. It’s the rudest of awakenings, and the breeding ground for self-determination. Don’t think of them as mistakes — think of them as learning experiences not to be repeated. How willing are you to make mistakes?" - Jeffrey Gitomer

It’s okay to be a rookie and make mistakes with assignment selling. Most people do. It’s a new tool in your sales team’s tool belt, and it will take a few swings before you learn how to perfect the process. Don’t be afraid to fail.

I’ve seen some companies start out by sending emails to prospects that include a link to every blog on their website, the ‘ole “spray and pray” tactic — or sales reps who recorded a personalized video while behind the wheel of a speeding car — both not good (or safe) ideas. 

🔎 Related: Wait, what the heck is assignment selling?

The important thing is these companies learned from the minor mistakes. They found out what works and what doesn’t pretty quickly. And now they share assignment selling wins with me about how one email to a prospect that included links to educational content on their company’s website, helped them close a deal and bring in revenue for the company.

And the truth is, now that your company is writing and publishing content on a regular basis, you’re already off on the right track. 

Pro Course: Fundamentals of Virtual Selling

What is assignment selling?

Assignment selling is the process of intentionally using all this great new educational content your company is creating about your products and services, and sharing it with prospective buyers to help answer their questions and calm their concerns throughout their buyer’s journey.

In its simplest form, we use assignment selling to educate our buyers throughout the sales process in order to close deals faster.

Start with content

Your company is starting to create and publish educational content on your website. That is awesome! Your sales team is helping the marketing department answer your customer’s most common questions and address their concerns through blog articles and videos. Even awesome-er!

🔎 Related: How to create sales enablement content your sales team will love

Maybe your team has just scratched the surface with writing sales-driven content, and you’ve recently published your first cost article. Or perhaps you’ve been cranking out articles left and right and have made an impressive dent in each of the Big 5 categories:

What are The Big 5 [v3]

Watch: What are 'The Big 5' best business blog topics?

Either way, your sales team is starting to get antsy — wondering when, and more importantly, how they can start sharing these resources with prospective buyers. We’ll dive into the when and how in just a minute, but let’s make sure we first define the why.

Why do we do assignment selling?

Educating your buyers is proven to drive revenue. Research tells us that, on average, 70% of the buying decision is already made before a prospective buyer talks to your company. That means buyers are taking the time to educate themselves on the purchases they are about to make. They’re going to learn about it from someone, why not you? 

And if they continue to learn from your sales team, how different will those sales appointments look?

If the prospect had answers to their most common questions and concerns about things such as “how much will it cost me?” and “what are the problems I might encounter?” — how might that knowledge affect your prospect’s buying decision? By using assignment selling, they’ll see your sales reps as teachers, helping lead them to make an informed buying decision.

🔎 Related: 5 real-life examples of assignment selling in action

When you use assignment selling effectively, this continued education will help move the needle on your prospect’s buying decision from 70% — quickly up to 80% or 90%, saving your sales team a significant amount of time typically spent answering these common questions on the phone, and allowing your prospects to qualify themselves during the process.

Education leads to trust, and trust is the true currency for any business.

At this point you might be saying, “Cool, Eric, I get it. Now how do I actually do it — and do it right?” 

You’re ready to start educating your buyers throughout the sales process, but you want to make sure you don’t make too many mistakes. I get it. I’ve had these conversations with dozens of sales leaders just like you, hoping to avoid the potholes and roadblocks that sneak up on us as we get started with assignment selling.

As a digital sales and marketing coach here at IMPACT, I work with organizations of all shapes and sizes. From small companies with a single sales rep, to companies with multiple service lines, each with their own sales lead, and over 30 people in full-time sales roles.

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. 

I have collected the most common mistakes that happen when companies are first getting started with assignment selling. Hopefully these lessons learned will help you navigate the road ahead more clearly, and give you confidence to get off on the right foot. This list might be short, but it packs a punch with details and specific examples.

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

  1. Underestimating the value of your sales emails
  2. Marketing and sales don’t talk on the regular
  3. A lack of transparency into what sales reps are doing
  4. Not celebrating your wins

1. Don’t underestimate the value of your sales emails

Every sale starts with outreach. Your sales emails are the lifeline to closing deals and bringing in revenue for your business. What you say and how you say it matters — and bad emails can quickly lead to lost deals.

Your sales team doesn’t need to follow a word-for-word script — that would sound too robotic and impersonal — the opposite of what we want to achieve in sales emails. But there are guardrails you can put into place to help keep your salespeople on the best path to success. Keeping your sales outreach tight, consistent, and personalized will help you reach your assignment selling goals of educating the buyer in every stage of the sales process.

🔎 Related: How to use personalized video in every stage of the sales process

Without guardrails, you run the risk of every salesperson running off doing their own thing — something I’ve seen at many organizations. This free for all is not only hard to track for sales leaders, it also produces inconsistent results and close rates with too much variance. 

If you’re looking to increase your average close rates, following these tips below will help you maintain consistency and effectiveness across your sales team.

Create better subject lines

What’s the first thing you see when you open up your email inbox? Junk mail from newsletters you’ve been meaning to unsubscribe from? Yeah, me too. So how do we stand out from the sea of spam that floods our inbox everyday? It starts with the first nine to 10 words in every email, your subject line.

This is your one chance to evoke interest, so don’t waste it on something as generic as “following up.” Here are four critical tips to creating more clickable, and meaningful email subject lines:

  1. Use the recipient’s name
  2. Include the word “video” (if you’re including a personalized video in the email body)
  3. Have a clear purpose for why they should open the email
  4. Say it in under 10 words or less

Let’s see it in action. 

Imagine I’m a salesperson for a company selling copiers and printers. I have a prospect (we’ll call him Tucker) who I know is looking for copiers for his small business. 

Here’s what a generic subject line might sound like to Tucker:

“Information about your copier”

Using the four tips above, here’s a more meaningful subject line for my outreach email:

“Tucker, a quick video about your copier solutions”

If I’m Tucker, and I’m scrolling through my junk-filled inbox, I stop because I see my name. The copy is less than 10 words so I can scan it quickly, and I have a clear purpose of why I should open the email — to help with my copier solutions. 

Personalize your emails

Using your recipient’s name in the subject line and the salutation are a great start, but don’t stop there, keep personalizing. Each time your reader sees their first name, it makes them feel valued.

A person’s name is to him or her the sweetest and most important sound in any language.” - Dale Carnegie

Here are three additional ways to personalize each outreach to remind your prospect everything about this email is tailored specifically to them.

  1. Use personalized video
  2. Share links to articles that are specific to your prospect’s questions and concerns
  3. Include a bio video in your email signature

Use personalized video

One of the fastest ways to build trust quickly with your prospects is to introduce yourself through video. This gives the recipient an opportunity to hear you, see you, and ultimately get to know you — all before speaking to you directly.

Say their name in your video. Talk about their company and call out their challenges, concerns, and questions. Reference that clear purpose you mentioned in the subject line and use the email as a brief teaching opportunity.

🔎 Related: What is 1:1 personalized video training and do I really need it?

Vidyard and Wistia are two examples of easy to use software solutions that make creating personalized videos as simple as one click. If you’re not using video as a sales tool like this, you’re missing a vital opportunity to build trust before ever meeting your prospects.

And when you copy and paste your video link into your email, make sure to use a thumbnail image so your prospect’s can see your smiling face before they click on your video. Vidyard gives you this option to copy your thumbnail image as soon as you’ve recorded your video. 

Here’s an example of a thumbnail image created using Vidyard:

It's not the actual video, just the thumbnail! 

Include a bio video in your email signature

A great way to wrap up your assignment selling emails is with a consistent email signature. This is also a great opportunity to close out your message with one last trust-building video.

🔎 Related: How to create amazing bio videos for your team members

Bio videos give you another chance to introduce yourself to your prospects and customers. Typically two to three minutes in length, these videos give basic information about you and your role at the company — but they also offer a chance to show a little personality, including information about your hobbies outside of work, and what you like to do for fun.

Here’s a great example of a bio video from Fire & Ice Heating and Air Conditioning:

If you have not yet created bio videos for your entire sales team, check out how you can get started making these amazing videos that help humanize your business.

Share links to articles that are specific to prospect’s questions and concerns

To use our example from above, if we know that Tucker is interested in buying copiers for his small business, let’s not waste his time by sending him links to educational articles with titles like “Small printers for your home office” or “Best copiers for your large business solutions.”

These are not specific to his concerns and needs for his small business.

Find educational articles and videos on your organization’s website that will educate your prospects, based on their specific concerns. 

Pro tip: When you include hyperlinks in your emails, always use the title of the article or video.

2. Marketing and sales teams don’t talk on the regular

Many companies suffer from silo-itis. A rampant condition where sales and marketing teams work entirely independently of each other. They don’t talk and share ideas, knowledge, and processes. These silos can make it very difficult to do assignment selling effectively. 

Why do silos form in many organizations? The answer is probably the laziest phrase in business, because that’s the way it’s always been done. Sales is perceived as the revenue generators, out on the front lines bringing in money for the company on a daily basis. And marketing is seen as the expense, working on amplifying the company’s brand, but not contributing to the bottom line. 

🔎 Related: What is a revenue team? (definition + revenue content tool)

Some companies have a tough time getting out of this mentality. They think that sales needs to sell, and marketing needs to market. They’ll break down the walls for a day and run a content brainstorm between both groups. This is a great first start, and something to be applauded when complete. But after the editorial content calendar is filled out with common questions received by the sales team, they go back to their respective corners of the office.

Without regular conversations with marketing, how will the sales team know which articles and videos are soon to be published on the website? How will the marketing team know which specific content is helping the sales team close deals if they’re not consistently meeting to talk about what’s working?

I’ve heard some marketing teams say:

“We did our content brainstorm and it went great. But now we can’t get the sales team to return our emails about new questions they’re being asked or which articles they’re using the most in the sales process.”

These silos represent a breakdown in communication, and ultimately, a breakdown in the quality of your company’s content. 

The solution? Establish a revenue team:

Liz What Is Rev [v3]

Watch: What is a revenue team?

Meeting weekly or bi-monthly, the revenue team is a collaboration of the sales and marketing departments working together towards a common outcome — to generate revenue for the company. 

Every video published on the website and every article shared in an assignment selling email — the goal is to educate your buyers, generate qualified leads, and make sales. 

3. There’s a lack of transparency into what sales reps are doing

If I asked your sales leaders what percentage of your sales team’s emails currently include personalized videos and links to educational articles, could they provide a specific number?

If not, that’s okay, you’re just getting started.

But this is where you want to be. Having insight and transparency into how your team is using assignment selling will help you identify areas for improvement, and get everyone working toward becoming world-class sales communicators.

Sales leaders should regularly review emails from reps

You don’t need to do this every day, but you can start with once a week. Ask each sales rep to BCC you on at least one sales email per week. Set time aside each week to scan through and review each email for the best practices we mentioned above.

I’ve seen sales leaders collect these emails on Fridays and immediately place them in an email subfolder titled “Weekly Email Review.” This helps keep things organized in one place, and you can set a reminder every Friday to take 15 minutes to review and provide feedback as needed.

🔎 Related: 5 reasons why you're not hitting your sales goals

Do the subject lines include the prospect’s name? Is the personalized video recorded while driving, holding their phone, and eating a cheesesteak sandwich? (I’ve seen that, and it’s not pretty). If and when these things happen, you’ll want that transparency so you can help them course correct, and identify what to change and improve for the next time.

4. Not celebrating your wins

Sometimes the successes will sneak up on you. 

I had a sales leader tell me recently about a really exciting prospecting opportunity with a potential new customer. Not only was this a chance at a year-long contract, but the prospect was a customer of their biggest competitor. 

🔎 Related: How to measure content ROI, celebrate wins, and keep your job

One of their sales reps already knew the prospect’s biggest concerns and most burning questions, so she sent an outreach email that included a personalized video, two articles about how much their services cost, and a video introducing their installation process.

The next day, the sales leader contacted me saying they had won the deal — followed by “this assignment selling stuff really works!”

I quickly wrote back and asked how they planned to celebrate this big win for the company? She said “Probably over a couple of beers :)”

I’m not going to stand in the way of an excited sales rep and a few iced-cold IPAs, but I really wanted to hear how they planned to share this with their entire company. Sharing the wins is how you truly make assignment selling stick within your organization.

🔎 Related resources:

Some salespeople might not entirely see the value just yet, or they need to be convinced that this is a new tool in their toolbelt worth using. When they see the wins in terms of revenue for the company, commission-won, and new deals closed, that’s when they start to say things like “this assignment selling stuff really works!”

You can share your wins on something as simple as a company-wide Slack channel — or present your assignment selling wins every month at your all-staff meetings. Find a creative way to let your entire company know that educating your buyers throughout the sales process is leading to sales.

By failing to prepare, you are preparing to fail

Now that you know where the potholes are on your road to success, will you swerve at the last minute to avoid them, or patch them up now with a process that fixes these issues and creates a smooth path to assignment selling growth?

Take the time to create effective sales email standards for your team, using the best practices for subject lines, personalized videos, proper hyperlinks, and bio videos. Have your sales and marketing teams meet regularly to discuss what’s being published on your website, topics in the queue, and new questions to include on the content calendar.

🎓 Online course: Assignment selling content is the most powerful sales tool

As a sales leader, take the time to review your team’s sales emails and see how they are progressing. Give them specific feedback on how to improve and make sure you showcase the assignment selling wins when they happen.

The goal here is not to create “to do lists” for your sales reps. Rather, it’s to instill a culture of education, shifting the mindset in every salesperson that we must all think like teachers in order to educate our buyers and build trust faster. Fixing these four mistakes will help you create a process that works for your team, and move them from simply checking off the boxes, to creating new, trust-building sales habits with assignment selling.

And if/when you make one of these rookie mistakes, remember what Jeffrey Gitomer said: “Don’t think of them as mistakes — think of them as learning experiences not to be repeated.”


Pro Course:

Fundamentals of Virtual Selling

Learn how to close more deals in a video-first, virtual workplace

In this course, you will learn:
  • How to use video through different stages of the sales process
  • How to use video to improve engagement and increase revenue
  • How to measure your success with virtual selling



Virtual Selling
Inbound Sales
Assignment Selling
Sales Process
Sales Professionals
Published on November 12, 2020

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