I still go through my morning routine of cleaning out my inbox. I’ve resisted having Claude it for me, partly because I learn a in skimming my inbox.
Every morning I have over 100 emails in my in box. About 35% are clients/prospects and get a lot of attention. Another 15% are from Substack or other feeds I subscribe to. I skim a few and file the rest away for evening reading. 5% are offers from airlines or hotels I’ve used recently.
The other 45% are people prospecting me.
About 1 in every 200 is decent and provokes interest. But the rest are horrible. I’ll come back to what sets these 1 in 200 apart.
I skim all these emails. Partly, my business is to help sellers connect more effectively with customers, so I want to see what people are doing. Part of it is my curiosity about what people are doing in their prospecting.
Some observations.
None of them have taken the time to research me or my business. Even though we have AI tools that make this easy, none of them have taken the time to do this.
They all have some sort of provocative statement about how they can improve my business. Mostly it’s about getting me more lead and opportunities. I wonder, “If they know nothing about me and my business, why do they think they know what I need?” For those that are offering lead gen and prospecting services, I think, “Is this the way they would represent me?”
Then there are the “sequences.” There are those that have been told 16-18 touches are needed. I see the sequences. Most of them are, “Did you see my last email?” Some are “This is my last outreach,” but I know they are mid sequence, so I can count on receiving more, last outreaches or did you see my email.
Some go through changes in their messaging, I give them credit for that. But I typically see them repeating themselves after the 4th or 5th.
One started sending me emails starting August 11. He’s getting impatient, the last few days he has sent me 2 a day. He’s up to 16 outreaches, so I expect I’ll receive another 2-3 and he will have completed his sequence.
I’ve had a long “relationship” with a few. One, from a well known company, started sending me emails in January 2024. To date, I have received 274 prospecting outreaches.
There’s one “guru” who has the secrets to success. He knows most messages are spammed. So he changes his email address every 3-5 outreaches, to get around the systems people have put in place. Such a great lesson to learn. Every week, I receive 1-2 emails from new email addresses. I block them. Every once in a while, I look in my Spam box and see another pile of follow-up emails from him. This pattern has repeated for about 2 years.
Many of these people have high visibility in LinkedIn, offering their insights on high impact prospecting.
Some of you are thinking, “Well these must be very small organizations who don’t know how to prospect.” But at least half of them are from well-known companies.
And I don’t even track what’s going on in my Spam box. As I wrote this, I looked at it out of curiosity. In addition to those trying to steal my money were a large number of, “You need our products….”
I went back to the handful of outreaches that caught my interest. How were they different?
They weren’t terribly personalized. That is, they didn’t start with, “Dave I read your post on ….” They didn’t focus on challenges with my business. They did focus on challenges my clients might face. They didn’t talk about their products or how I would benefit from them. They focused on the issues my clients face and sought my views.
They were interesting enough that I went to their company websites to start looking at their orgs and the solutions they sell. And with a couple of them, I asked to schedule a discussion. We’ll see how those go, but given their approach to date, I suspect it will be good.
As I reflect on the good, bad, and ugly (heavily weighted to ugly) of the prospecting outreached inflicted on me and so many others, the issue isn’t that prospecting/outbound doesn’t work. It’s that we don’t understand what we should hope to accomplish.
We’ve made prospecting about our goals and objectives. Generating responses, booking meetings, scheduling demos.
Those I paid attention to made me curious.
I was curious enough to look at their websites and LI profiles. I was curious enough to have a conversation.
Rather than chasing me, in some sense I started becoming interested in them.
And in talking to them, I found they had carefully researched me and my company. They had read some of the articles. They had chosen to reach out to me because they thought I’d be interested in the conversation. And, in their outreach email, they didn’t have to prove they had researched me. Research was just part of how they worked and prepared.
We’ve always thought prospecting is to find people interesting in listening to what we have to say. But what if we started rethinking it?
What if we thought of prospecting as finding something they want to talk about?
Doing this, we still must carefully research the people and orgs we seek to reach. But the difference is understanding what they might be interested in. What is most relevant to them right now? What may be happening in their markets that might be important?
The objective of that first encounter isn’t to qualify them and schedule a demo, it’s to engage them in talking about something they are interested in. We want to create a meaningful experience, where they invite us to explore the issues further.
It’s about creating conversations that customers value and in which we begin to establish trust.
Some may push back, saying, “Dave we can’t waste our time doing this! We have to hit our goals!”
The rebuttal to this is very easy. First, we should never be prospecting outside our ICP. Closely focusing on our ICP increases the likelihood that we can find those people and have those conversations.
The more powerful rebuttal is, “What you’re doing isn’t working now, why not consider something different? Think of the 274 outreaches one company has made in the past 20 months. Not a single one provoked interest.
But underlying this pushback is a real fear. The majority of sellers don’t know how to have these conversations. The only thing they know is their products, scripts, playbooks. They don’t really understand their customers and their businesses. They don’t have the acumen to be able to engage in these conversations.
And this isn’t the fault of the seller. It’s that we’ve designed our prospecting systems that don’t require or reward their ability to engage customers in this way.
Sellers are just doing what we’ve told them to do, what we measure them on. And all our training and tools reinforce this.
We haven’t built the customer and problem acumen critical to their ability to provoke those conversations with customers.
Our tools and training don’t show how to research and engage customers about business issues they may be interested in.
Our metrics don’t focus on measuring high impact conversations the customer is interested in.
I’ve often challenged my clients, “What would you talk about if you couldn’t talk about your products?” I’d shift this in our prospecting outreaches to say, “What would your outreach look like if it wasn’t about your products? What would provoke the customer to want to have a conversation with you?”
I titled this, “They know what I need but they have never spoken to me.”
The reality is the majority had no idea what I need, they focused on what they wanted me to need.
The few that stood out wanted to understand what I thought. And through this, we might discover what I need.
Afterword: This is a must listen to AI discussion of this post. They bring a huge amount of humor looking at what we do in prospecting, and great insights into what’s wrong with prospecting. While this sounds obscure, their discussion on intellectual validation is fascinating. Enjoy!
