“I’ve invested in training, coaching and tools before… and been burned,” said our student Tony, a successful entrepreneur in the engineering and design field. 

Tony launched and is still operating a successful business—for over two decades. He has what it takes. But he needs to grow.

Now.

Prospecting had always grown the company for him. Sure, he said to me., inbound marketing is trendy and, for some, it creates conversations with potential buyers.

But so far his HubSpot email templates were failing to engage prospects in conversations.

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

Tony felt ripped-off.

Blindspots—portions of email messages we cannot see creating big problems. Because we are the source of the problem they are difficult to spot.

Too much self-talk. Weak tone. Not standing out. Negative mental triggers—sounding too persuasive, asking biased questions. Lack of provocations. 

I have blindspots. You do. We all do. And not just with email. In life and in business. This is why (the good) consultants 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. 

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

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

Tony’s messages were all problematic. I noticed it immediately. It’s my job. 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 this 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. 

We found Tony’s blindspots—immediately. It was easy.

“Is this 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!)

Because hook questions are typical spammy crap. They don’t help you stand out in the inbox. You blend in with the noise.

Hook questions are biased to an answer the seller seeks—as a means to start selling. 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, Tony 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 noise.

Instead, start focusing clients on change THEY might choose to direct—on their own terms, on their own schedule, if they decided it was appropriate and, possibly, with the help of a service provider.

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 Tony got his drip sequence sorted and nabbed a lead:

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

Philip W.

Here’s how Tony earned it. He:

1. asked an un-biased, inward-focused question—helping the prospect consider his situation;
2. provoked thought on the client’s status quo—and how it may be hurting him;
3. stood out from cheap email come-ons—encouraging Philip to read the next sentence;
4. reduced the size of his message to be smartphone short, earning the short reply.

Tony 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 Tony’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. 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.

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.

Speaking from the heart: I see recommendations being made by “experts.” I know this advice won’t work—except by accident. Because our community knows which tactics are currently starting conversations… based on outcomes our Academy members demonstrate every day.

Yet these “best” practices are trumpeted on LinkedIn—and flocked to by legions of (usually) low-skilled sellers seeking silver bullet answers.

It should be criminal.

I recently made a sales trainer friend. His name is Andy. He says… “I think the problem is worse than people lying. It’s that these people have so little real world experience on which to base their ‘expertise.’ And when they get a little social validation they become true believers in their own BS.”

Thanks for letting me get that off my chest. Because I want you to find your blindspots too. It’s the fastest way to get better at outbound prospecting.

Ok. Share your thoughts in reaction in comments please. I welcome your critical thought and different experiences. This is how we learn.

How will you find a better way to start client conversations? Our community and workshops are here to help. We live and breathe this stuff! There are multiple levels of commitment to get involved.