“I just finished a year of Lead Forensics putting 1,000 leads through email sequences using Hubspot. Not one sale,” said our email writing student, a successful entrepreneur. We’ll call him Jason to protect his identity.

“Before that I hired a cold calling team. It was a one year effort. Zero sales. They gave a second effort on the house. That landed one sale that covered my costs.”

“Nothing is working,” outside of occasional referrals. But Jason’s successful, 22 year-old business can no longer rely on word-of-mouth alone.

He was frustrated. But not done. After all, he launched and is operating a successful business for over two decades. Jason has what it takes. But he needs to grow.

Now.

Prospecting new customers is the lifeblood of his company. Always has been, always will be. Those are his words, not mine! Sure “inbound marketing” is trendy and, for some, it generates conversations with potential buyers.

But so far his HubSpot email templates have failed to engage potential customers in conversations.

“I need to increase gross sales… and I need a better process for doing that,” Jason told me. But he was terribly reluctant to invest in email writing coaching. 

Could it really make a difference? His gut told him yes. But he was gun shy given all the failed investments and wasted time. Not to mention broken promises of vendors and consultants.

Jason felt ripped-off.

Every seller has blindspots; portions of an email message we cannot see creating big problems. Because we are the source of these poisonous tendencies they are difficult to spot.

Bad word choice. Weak tone. Persuasive hooks.

I have blindspots. You do. We all do. And not just with email. In life and in business. This is why (the good) consultants and coaches are worth every dollar invested. They quickly see the blindspots we cannot. (and course-correct us)

Peer review of your ideas, real-time sharing of “which tactics work, which don’t.” Life long learning. All of that. This is why professional communities (of sellers) are worthwhile. (e.g. our Spark Selling online Academy) 

The key to starting more conversations, using email, is spotting and fixing blindspots. Here is one of the most common examples: Biased “hook” questions.

In Jason’s case he dripped six emails to organizations identified as visiting his website. Companies like Lead Forensics help identify the company but the rest is rather like guesswork… trying to understand who within the company visited.

Once targeted, Jason was sending the six messages—seeking conversations with prospects. He used HubSpot to send and analyze open and response rates.

Jason’s messages were all problematic. But his third HubSpot email template asked these “hook” questions:

“Many companies have a product development process that follows a similar schedule year after year. Is that is the case in your business? When a pattern exists, it is much easier to plan for the slow time as well as when things get completely crazy. If there is no pattern what do you do when more projects land on your desk than you can handle?”

These kinds of questions are typical in our experience coaching business owners and sales reps. Hook questions. Leading questions. Questions that “push on pain points.” Questions marketing people often write, hand to sales people and say, “try this approach.”

Big mistake.

Persuasive tone and hook questions = instant death in sales prospecting emails. Aiming to persuade targets to have a meeting is mostly a non-starter. This goal is a complete non-starter for B2B sellers of complex, longer sale-cycle products and services.

Starting a conversation asking for a meeting (without being invited into one) is a great way to get rejected and/or secure meetings that go nowhere.

Standing out. It’s what gets your email opened and read. But how?

“Is that is the case in your business?” and the other (above) questions communicate “I’m asking because I want you to confirm (for me) what I’m sure is your problem—so I can sell you something.”

These are COMMONLY ASKED hooks. Customers see them over-and-over in inboxes. Customers aren’t fish. Hence, they don’t bite.

Answering a question like “Is that is the case in your business?” makes customers with latent need feel too vulnerable. Result: They don’t answer and increasingly hit delete. (or worse, spam… an even faster way to un-subscribe!)

Hook questions are biased to an answer the seller seeks. That’s what makes such cheap, come-ons easy to spot and delete. They are clearly (that’s the problem!) rooted in the seller’s desire to “open the door” to a sales discussion.

Instead, Jason should be asking questions. But with inward focus… helping the client examine his/her decision-making process with regard to possible change. He should be asking questions about, for example, how the status quo was created.

This separates your message from the pack.

What works is simple: Focusing clients on change THEY might direct–on their own terms, on their own schedule, if they decided it was appropriate and, possibly, with the help of a vendor like Jason.

Success demands you gain permission to help prospects decide on a meeting themselves. Thus, your email message templates must help prospects persuade themselves. Everything else fails.

However, it is impossible to have a 100% accurate perspective on communications effectiveness—unless you have trustworthy (and qualified) people giving honest feedback.

Finding your blindspots.

Within a few weeks Jason got his drip sequence sorted and nabbed a lead:

Hi Jason-
Thanks for tracking me down.  I am interested in your thoughts and am certainly open to discussing opportunities.

Philip W.

Here’s how Jason earned it. He asked an un-biased, inward-focused question… helping the prospect consider his own situation for a moment. This provoked thought, stood out from other email come-ons and encouraged Philip to read the next sentence.

Jason opened by asking, “How would you know if (and when) it’s time to consider a different or additional product development path?”

He asked a neutral question. Questions are dangerous (in general). But this question is neutral to Jason’s natural bias.

His second (of three) sentence was, “I’m asking after noticing the innovative baby bed on your site… Are you open to considering a conversation about change—if it is the right time?”

Notice how short this approach is. Notice also how customer-centric the questions are—and how the seller does not discuss himself whatsoever. Most importantly, the question posed is not a self-serving marketing hook. Instead, it’s provocative.

Want to stand out from the pack? Write messages in ways others aren’t. This way. Write messages that do not serve you—as much as they serve (and provoke) the reader.

Ready to start? Join a small group of us online as Jed Fleming and I strengthen outreach to provoke conversations.

Truth is, most people who support us rarely give brutally honest feedback. They usually have a horse in the race. Or they’ll tell you what you want to hear—rather than what you need to know. Increasingly, we take free advice from experts who aren’t experts at all.

Are your co-workers, marketing team, software vendors, friends, spouse and Uncle Google really the best people to get prospecting outreach advice from?

Do writers of articles you’ve Google’ed have YOUR best interest in mind?

In most cases, no.

Think about it. Jason has been driving sales outreach without checking blindspots. You wouldn’t drive a car that way. It’s too dangerous.

So why drive your outreach this way? It could be costing you a lot of money.

How will you find a better way to start client conversations? Our community and coaching workshops are here to help. We live and breathe this stuff!