I get a fair amount of cold pitches my way. I cannot spend time responding to all of these pitches other than to provide a terse “no”, but on occasion I will take a bit of time to correct some of the more egregious, yet innocent prospecting mistakes.

One memorable exchange last year was from an SDR that sent me a canned LinkedIn connection request. I replied that his technique was ineffective and provided a link to one of my earlier posts about how to use LinkedIn properly. He responded soon after with this:

“We face the universal sales problem of reaching a large number of people without sounding like spam.”

He then went to some length to justify his approach. I replied suggesting that his line of thinking is a logical fallacy. Why automatically assume the need for volume?

You often hear the phrase “sales is a numbers game”. The premise is that you need enough activity at the prospecting stage (top of funnel) to have enough opportunities to achieve your sales target (bottom of funnel). There is truth in that premise.

But ask yourself this, how much activity are you investing and for what result? If you are doing a whole lot of prospecting without positive results, that’s insanity, as the saying goes. It means that something is broken in your prospecting approach and you do not fundamentally understand your sales process well enough achieve volume.

We often over-execute on prospecting and under-invest in the strategy behind our prospecting. If we reversed this and gave more thought as to how we are prospecting, we would avoid the pitfalls that lead us down the path of becoming a spammer.

We often over-execute on prospecting activity and under-invest prospecting strategy.

Most of us think of spam as the act of sending out lots of unsolicited emails. However, I consider spam more broadly as any communication across any medium or channel or stage of sales cycle that is devoid of value to the recipient. So having a call with a prospect where all you do is pitch features is just as spammy as sending out an email blast to a thousand people you do not know.

In this context, spam takes on five flavors:

  • Spam of messaging where our message is not attuned to the prospect
  • Spam of volume where we do not create a valuable one on one connection
  • Spam of ignorance where we lack basic understanding of the prospect’s business
  • Spam of relevancy where we are unable to link prospect value to solution
  • Spam of conversation where we cannot influence a prospect’s thinking

If we can identify in our processes and techniques the types of spam we are creating, we can then begin to build a stronger foundation for our prospecting execution.

Image for post

This requires we return to the first principles of prospecting, or what I deem The Prospecting Manifesto:

  • Connecting to the prospect’s why versus treating everyone the same
  • Knowing each prospect versus spamming a list
  • Understanding a prospect’s business versus wallowing in ignorance
  • Asking insightful questions versus pushing your agenda
  • Helping prospects think versus qualifying them through a process

I explore these five principles below as a counter balance to the temptation towards employing spammy tactics and value destroying approaches that prevent us from building trust and credibility with prospects.

Connecting to Why

Most sales reps obsess over subject lines and witty openings. But having a clear, concise, and compelling message is the only way to move beyond opens and to convert leads into quality opportunities.

Do you really know who are you selling to? Do you know why they would care about you and your solution? What drives them to ask, “tell me more”, instead of hanging up or deleting your emails?

While marketing is the group usually tasked with creating personas and messaging, they are working on the macro level. They also do not have a quota. And they often do not have a deep sense of the emotional core that drives people to make decisions.

That is where sales lives. We thrive in the emotional, one-on-one engagement that takes ideas and creates ownership in the mind of the prospect. But we cannot do that unless we understand what they would most fundamentally care about, such as getting their job done faster, receiving better compensation, or advancing in one’s career.

For example, perhaps you are selling software to internal recruiters, who might be struggling with the lack of quality candidates. They are getting pummeled by their internal buyers. They are under the gun to produce. So what do you think will pique their interest more, the features of your product or a story about how you helped another recruiter look like a rockstar?

If you are not connecting with prospects, switch up the strategy and go to their specific why. That “why” differs based on buyer types or personas. Your buyer types are simply people that would be involved in the purchase. In our recruiter example, that could be a VP of Talent, the Hiring Manager, a COO, an employee brand manager, or the front-line recruiter.

Once you identify your buyer types, create a grid with your buyer types (personas) in one row, challenges or opportunities that would speak to their internal why as column headers, and 1–2 questions you can ask to evoke a response confirming or disagreeing with the “why” you suggested as tied to something your company can uniquely offer.

What if you cannot find something compelling to say to a particular persona? Do not worry, it takes a few iterations to hone your messaging to get it just right. Talk to current customers or people in your network with the titles that match your personas. Once you have the messaging together, you can then focus on only those prospects that would experience and care about the “why” you address.

Knowing Each Prospect

It is natural to want to pump up the volume when you are in the early stages of building pipeline. You are starting from zero after all and that is a scary proposition when looking at your quota.

If you are not seeing consistently positive results at volume though, reduce the volume. Instead craft your outreach to be more personal and insightful. Put yourself in your buyer’s mind and understand what they would find valuable and important for them. Then you orient your messaging to be about them instead of about your product and your company.

I lay out a quality based approach in my posts on using LinkedIn and general outreach tips. For the TL:DR crowd though, I summarize the formula like this:




[NEXT STEP]. Thanks,


That is a maximum of five sentences that you can even condense down to four or three if you are creative. Remember you are competing with all the other stuff jamming your prospects inbox, and vendor emails are the lowest priority after the boss, family, colleagues, customers, company internal emails and pretty much anything else.

You might think then that a witty subject line is necessary to drive opens. However the objective is not email open rates, it is to identify qualified deals. Your best opening is always short and to the point. Carrying on the recruiting solution example, you might say “Increasing Candidate Quality for [COMPANY]” or “Saw Your Post on Recruiting, Let’s Chat”. They are both straight forward and more importantly is about the prospect or the prospect’s organization. It’s about them not you.

If you get your messaging and account / persona targeting right, you can then begin to scale your efforts, implement automation, and build feedback loops to continually tweak your messaging for higher effectiveness. Remember that it is better to go deep then learn and iterate than to jump immediately into the volume game.

Understanding Their Business

When you reached out, did you just use your standard pitch to get the next meeting? If so, you just made the person on the receiving end feel like they are a target rather than a person.

What if your goal was not to make a sale but to instead make the person smarter? Instead of wringing a few more seconds getting as many words out as possible to convert a lead to a meeting, change the game. Give the gift of a unique insight or different perspective that provokes new ideas.

That is ultimately what we do in sales. We are in the business of changing mindsets. You help open minds to see solutions that may never have occurred to others.

This brings us back to the persona mapping matrix from before. The questions and messages you create are based on the prospect’s “why”. Understanding the why however is not always obvious. How do you learn someone’s “why” and craft messaging that would be meaningful?

You need a deeper understanding of the industry and the types of people you are selling to. In short, it requires you gain industry acumen. Here are some sources to begin your quest for knowledge:

  • Read online trade journals
  • Interview existing customers
  • Review case studies / customer stories
  • Interview people in similar roles inside and outside your company
  • Attend industry tradeshows, events and meetups
  • Consume books, podcasts, and other long form materials

Do not simply outsource knowledge acquisition to marketing! It is your responsibility to understand your market beyond mere knowledge of your company’s products. Your prospects rely upon you to be a trusted resource. Otherwise, what value do you provide as a salesperson? Elevate the game and become a deliverer of insights.

Asking Insightful Questions

Selling with insights is a great concept. If you come up with enough smart things to share, your prospects are going to stop and listen. Right?

At this stage, you have most of the raw ingredients. You are focusing on quality and personalization, targeting the right buyers with the right message, understanding the internal “why” that drives buyer decisions, and delivering worthwhile content to share.

Most of the time however our prospecting will still fall flat. Why? Because we bust in the doors with a host of insights like we are battling a three-alarm fire. Most of our prospects however have no idea there is a fire or even a whiff of smoke.

My friend Michael Harris had this to share in a LinkedIn thread:

If sales knew why a customer changed, they’d know where to shine the light of insight on new customers to expose the unrecognized problems and costs of the status quo. And as customers discover the risks of the status quo are greater than the risks of change, they’ll be highly motivated to change. Look for insight in the customer’s blind spots.

The subtle lesson is instead of throwing darts on board in the hopes of hitting a bullseye, we should first seek to understand the change that is happening inside organizations that are potentially receptive to the message. How do you do that? By asking great questions.

The way cognitive biases work is that if you throw a bunch of insights and facts & figures at people, they get defensive. Our minds perceive direct statements as threats to avoid. They perceive attack whereas you feel that you are simply trying to be helpful.

If you wrap your insights as questions however, you have an opportunity to open the conversation. People are more apt to answer an informed question and to own the responses they provide. Our questions therefore not only help to better inform us, but they open up the minds of prospects to new ideas. When in doubt, ask more questions.

Helping Prospects Think

What is keeping you up at night? You know what keeps me up, sales reps asking that horrifically outdated question to prospects. Yet, most questions asked by sales reps do not rise all that much higher in the effectiveness department.

Sales reps are constantly told to ask more questions, to speak less and listen more, to be engaging, and to demonstrate insight. The most fundamental and important of these however is to ask questions. If you ask good questions, rest takes care of itself.

But what should you ask? Most of what I hear in calls never goes beyond the most basic, information-probing questions. While that is helpful to qualify a prospect, they are not engaging for the person on the receiving end. These are the annoying sales questions.

A question is an opportunity to make a prospect think critically of their situation. Your job as a sales rep is to help people see a better way of doing things. You are doing inception, injecting new ideas that can cause a person to take action. The problem is that you cannot just tell people about the new idea, they need to arrive there by themselves.

I mentioned before how the mind is generally hostile to new ideas that come from the outside. That is the magic of asking thought provoking questions, the prospect is leading themselves down the path to seeing that better vision of the world, all without you explicitly telling them what to think.

So how do you ask amazing questions? Read this excellent post by James Muir which breaks down the process for creating great questions and how to ask them.

True value-adding questions are those to which the client does not already know the answer.

Questions are your most powerful weapon in sales, so be well armed and prepare. You will know you have succeeded when your questions lead to

Many make the mistake of thinking prospecting is all about banging away at the phones. They get caught up in the tactical motions, but the more successful prospecting come from taking a more thoughtful approach. It is not easy, but once you go through this effort, you will have a sound prospecting strategy. Execution in sales matters, but only once you got the right plan to execute.

Let me know your thoughts on this topic and The Prospecting Manifesto. Would you change it, add to it, simplify it? Thanks again for reading!

Leave a Reply