Three Reasons Your Outbound Strategy is Failing

Building an outbound sales strategy is a lot like painting a house. How you prepare for the job can have a big impact on the quality of the end result. Of course, when it comes to preparing there are a few basics to keep in mind. For example:

  • reaching out to the right buyer personas for your solution
  • making sure your emails and phone calls land at the right time of day
  • ensuring you have a sufficient volume of leads and activities for the pipeline you’re trying to create.

But that’s just the start.

Back at Salesforce, I noticed a strange trend with some of my reps. They were making tons of phone calls to the right people, at the right time of day, but not generating as much pipeline as you might expect given their level of activity. So I decided to dive deeper, see if I could diagnose the problem, and provide some coaching. As I listened to dozens of calls to hear where things might be going wrong, some interesting trends emerged. Problematic trends that weren’t showing up on any report or dashboard but ones I’ve since found to be consistent across many of my clients experiencing outbound turbulence.


1. You don’t have your buyer’s attention

In his book Buy-In: Saving Your Good Idea from Getting Shot Down, author John Kotter says we’re bombarded with 520,000 proposals, plans, or ideas in a single year. On a typical day, we can be slammed with six requests and four complaints from our family before 7:30 a.m., 14 things to remember from the radio program we listen to going to work, and dozens of new emails by the time we get to our desk.  And according to Gary Keller, author of The One Thing, we get interrupted every 11 minutes and spend about one-third of our day recovering from those interruptions.

The reality is, buyers (like us) are busier than ever and have scarcely little discretionary mental bandwidth. If you don’t earn your buyer’s attention, your message will fall on deaf ears. 

A simple tip to get that attention is to try a different medium. For example, data shows that open rates on video messages are 10X that of old-school text. Bringing your customers the gift of personalization by doing your homework to drive reciprocity is always a good call (see video below).  Or better yet, unleashing the massive conversion power of advocacy by getting referrals and warm introductions from happy customers who can more easily secure your buyer’s attention. Not to mention convert at rates 50 times higher than email campaigns! 

Helpful video: Prospecting Tip – How to Use Reciprocity to Increase Response Rates


2. They can’t figure out how you can help

Steve Krugg, author of the best-selling book, Don’t Make Me Think, says of your company’s website, “If visitors can’t identify what it is you do within seconds, they won’t stick around”. The same applies to your outreach…but with a twist. Your customers don’t need to know what you do. Rather they need to understand the problem you can help them solve! Unfortunately, most failed conversations tend to place the focus on the vendor’s products and solutions (e.g. “Oh hello there Mary. My name is Steven and I work for Acme Co. We specialize in high-volume marketing automation solutions and analytics“). And to make matters worse, regardless of how well-differentiated we believe our solutions are, most of us tend to sound the same to our buyers simply because of the sheer number of solutions saturating every market. For example, in the Marketing Technology space alone, the number of vendors has increased from 150 in 2011 to over 8000 today.

So when it comes to getting your intro pitch to not only be heard but resonate quickly, the science of persuasion can help modern sellers operate with armor-piercing efficiency to convert more customers. The secret is leveraging a principle known as processing fluency; the ease with which information is processed.

For example, instead of describing what you do, your message should focus on who the enemy of your solution is. Are you trying to stamp out crappy performance reviews that most employees hate? Are you focused on helping sales leaders understand why their sales funnels are leaking without having to sift through piles of data and complicated reports? The power of juxtaposition and contrast can also be helpful here. For example, have you ever noticed that when you’re watching an infomercial for a new kitchen gadget, the argument to purchase it all of a sudden becomes more compelling when they start listing all of the older clunky, expensive, and hard-to-clean appliances their gadget can replace?

The quicker you can deliver clarity to your customer around how you can help, the more likely they are to lean in and say, “Interesting! Tell me more!”

Helpful video: The Power of Polarizing Messages

Helpful Video: Supercharge your Narrative with the Ninja Pitch


3. You feel you’re bothering them

Let’s face it. Customers generally hate unsolicited sales outreach. And because most of us feel the same, we can easily empathize with those we call on. It also doesn’t help that most outbound outreach involves an element of experience asymmetry; an imbalance created when younger, newer, or generally less experienced sales reps call on a more senior decision-maker whose job they’ve never done. For these reasons, despite our best efforts to “smile and dial”, many times when we call on our customers we feel like we’re bothering them. We are emotionally compromised. We sound tentative, unsure, or even fearful, and our customers feel that uncertainty in the tone and demeanor of the seller during the interaction.

But imagine you were calling your customer to tell them they just won ten million dollars in the lottery. How would your tone and enthusiasm change then? Would you feel you were bothering them? Of course not! So the key is to figure out how to manifest the same degree of conviction in your current outreach. For example, get customers to share first-hand stories with your team and phrase your narrative in their voice! Wharton School of Business school professor, Adam Grant, conducted an experiment where students who received scholarships funded by alumni donations share first-hand, life-changing stories of how the scholarships impacted them with the fundraising reps. The result, a 400% increase in average weekly donation revenue because the reps were able to convey the value of their outreach with higher conviction. 

You can also reformulate your pitch to lead with beliefs and feelings rather than products. In his book, Start With Why, Simon Sinek, asserts that customers don’t buy what you do, they buy why you do it. For that reason, when sales reps lead with messages rooted in beliefs, their conversations are more natural and persuasive with negative feelings organically pushed aside in favor of high conviction and enthusiasm.

Helpful video: How To Speak with Credibility When You Have None!

Helpful video: How to Harness the Massive Conversion Power of Conviction!


Executing an outbound selling strategy can be tough. While tactical execution is fundamental to sales success, alignment around the emotional elements of attention, clarity, and conviction is equally important and unfortunately, often overlooked.


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