The 3 Ways Salespeople Are Getting Messaging Wrong

Aug 19, 2021
Author: collin stewart

If you know you’re not telling the story of your solution as well as you’d like – then you must also know that you’re missing out on deals. Tim Pollard, a recent guest on the Predictable Revenue Podcast, has developed a set of principles that apply to the full spectrum of messaging, from short outbound email copy to late-stage closing conversations. But, on his episode of the podcast, he narrowed in on early-stage sales conversation design. His methods look at the way the human brain consumes and retains information to help salespeople (and their messaging) close more deals and shorten their sales cycles. 


What Tim sees in most sales organizations, when it comes to demo and discovery calls and their supporting materials, are bloated powerpoint decks. “Powerpoint is not the fundamental problem,” Tim explains, “though you never want to use powerpoint in your meetings.” Powerpoint is a vehicle, and embedded within its presentations are the 3 most common and most toxic mistakes salespeople make with their messaging.

1. TMI. Salespeople try to pack too much information into their meetings. Even though we know from experience that as a buyer, we hate being inundated with information because it makes us tune out and switch off, salespeople still do it. According to Tim, that’s an indication of just how deeply ingrained this habit is into the salesperson’s psyche. 

2. It’s confusing. Many companies’ value propositions are unclear. The buyer follows the presentation, slide after slide, and comes away with a murky understanding of what your company does and why it would be of value to them.  

3. It’s sender-oriented. Most salespeople launch into a meeting by talking about themselves. They can get through dozens of slides before they begin to hint at relevance.

These 3 toxic behaviours most commonly occur together and in tandem with a shoddy powerpoint presentation. These behaviours have 2 outcomes:

Your meeting is not compelling. Your buyer leaves the meeting confused or disinterested. 

Your meeting does not pass the “retellability test.” The retellability test is a standard that Tim came up with that encapsulates one of the most underappreciated aspects of sales messaging and all communications in general. I’ll explain. You have your one-on-one meeting with your customer. It’s an early-stage meeting and you, as a salesperson, feel this is the most important meeting you will have with this customer. You’re not wrong. But what you’re missing is the other meeting that will happen that you won’t be privy to.

Your customer has to resell your product or service internally, to the buying committee. If your messaging was weak when you shared it with your customer, one can only imagine how awful it will be once it’s been reshared. And your customer isn’t going to fire up your same trite powerpoint presentation to show to their boss. Consequently, it is vital that your customer can run your solution up the chain of command without diluting the message. We’ll teach you how below.

Home office desk with a Macbook computer on top that display the text "do more" in white with a black background


Tim has seen the issues with sales messaging radically amplified in a virtual world. In taking a social interaction, like a sales conversation, and moving it into an asocial environment, the complexities compound and nuances can be lost. Tim observes 3 fundamental ways the dynamic changes in a virtual environment:

1. The problem of distraction. In a live sales conversation, customers are not likely to overly self-distract. They may glance around the room from time to time but, in most cases, they will stay relatively focused on the seller and the conversation at hand. In a virtual environment, distractions are rampant. Even with cameras and video turned on, customers are fighting against interruptions and diversions all the time. If their video is off, chances are they aren’t even looking at the video call window and they’re doing something else. If your messaging is already confusing, complex, unclear, or uninteresting, it becomes infinitely more so in a virtual world. (This is another reason not to rely on powerpoint slides – they’re another distraction. Make sure to show something other than you on the call no more than ⅓ of the time.)

2. Loss of mental bandwidth. This is a well-known experience for those of us working virtually. Working from home is mentally exhausting and zoom fatigue is very real. Again, if a customer already has reduced mental bandwidth, your confusing, complex, unclear, or uninteresting messaging is certainly not going to land.

3. Loss of feedback.

Great salespeople may not always be great communicators, Tim asserts, but all great salespeople are great at one thing: reading and responding to social cues. They can identify positive and negative signals and lean into them. In a virtual environment, especially if you’re sharing slides or your customer doesn’t have their video turned on, the fluctuations of unspoken social interaction are flattened. Customers become passive and inert and salespeople, in turn, struggle to read them and respond appropriately. As a result, salespeople need to plan and design interactivity for a virtual meeting.


1. Keep it crisp, clean, and simple. Set aside your tendency to overshare. 

2. Root your messaging in a customer problem. Your customers are not interested in talking about you or your solution until you’ve reached a shared agreement that they have a problem they would like to solve, and you can do that. Similarly, once the pain has been uncovered, don’t just label it and jump to a solution. Unpack the problem, ask questions, be consultative. At least ⅓ of each sales conversation should be about the customer problem.

3. Simplify your value proposition. Your value proposition should be expressed through the lens of a small number of ideas. The human brain doesn’t store data like a hard drive. Therefore, it doesn’t retrieve data like a hard drive – running a query and pulling up the exact information. The human brain boils each idea down to its essence for easier storage and retrieval. So, focus your value proposition on 3 or 4 big ideas, including what your customer needs to believe or be convinced of in order to take the next action. 

4. Support your ideas powerfully. Whatever materials or messaging you use to support your ideas need to do so in a way that is memorable. In sales, we tend only to support our ideas with facts and data. But imagery, story, metaphor, and physical artifact are much more engaging and more retellable.

5. Follow a logical story. If information has no flow, it’s hard to remember and hard to retell. Your messaging should be a symphony with 3 movements. Each one compels the buyer to listen on. Movement 1: You, the customer, have a problem that is bigger and potentially more serious than you had imagined. Movement 2: We have a solution that will solve this in a way that is fundamentally better than our competitors. Movement 3: This is how we move forward together. 

6. Set a concrete next step. This is sales 101. Just do it.

7. Embed your message in collateral that is specifically designed for retellability. This material will be presented internally later. It should be constructed the way you’d construct an argument. It has to be logically laid out, clear, powerful, and support the big ideas you shared in the meeting.


With the changes described above, Tim has seen teams’ sales conversion rates from 20-30% to the realm of 50-70%, and sales cycles dramatically reduced. One Oratium client went from a 13% conversion rate with a 40 slide powerpoint deck to a 34% conversion rate and sales cycle time cut in half with just these simple, logical principles.


If you think your messaging is a little weak, you’re probably right. And if your messaging is weak, you may be winning the initial battle of persuading one customer, but you’re losing the war when it comes to that customer selling your solution internally. Tim Pollard reminds us of 3 key mistakes to avoid, the 7 hallmarks of messaging, and, most importantly, reminds us that the most important meeting is not the one we have with our customer, but the one they have with their buying committee. So, make sure your messaging passes that retellability test and equips your customer to do the selling for you.

You can check out Oratium’s elearning if you want to learn more.


More on buyer psychology: Understanding buyer psychology and how it fits into the sales process with Outreach’s Max Altschuler

Having effective conversations in a virtual world: Communicating effectively in a virtual environment with Dr. Ethan Becker

And the psychology of sales in a virtual world: How fear of uncertainty is holding us back (and why it shouldn’t)



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