Why 97% of Sales Email Messages With Questions Don’t Work

Two of the most popular writing strategies in B2B sales email messages fail to provoke desired behaviors. Especially replies. Instead, they put your customer in a vulnerable position.

sales email messagesTwo of the most popular writing strategies in B2B sales email messages fail to provoke desired behaviors. Especially replies. Instead, they put your customer in a vulnerable position.


I’m talking about asking prospects questions and/or offering persuasive research.

Both tactics fail or under-perform. Because both result in tipping-off customers to your motive:

To sell … before they’re ready to be sold to.

These tactics reek of persuasion. While marketers think persuasive copywriting is good, it’s not.

Copy that openly allows customers to persuade themselves — if, and when, they’re ready for it — delivers consistently more value to both sides. Especially if you are trying to get a meeting with the CEO using email.

Are You Asking Customers to Become Vulnerable?

Are you asking prospects to:

  • Answer questions leading to an outcome you want?
  • Be persuaded by third party research to form a conclusion you want?

If so you are asking customers to become vulnerable. Nobody likes feeling vulnerable. Hence, your email (or even website) copy may be under-performing or not performing at all.

Because your persuasive tone screams, “I’m trying to persuade you … answering (at all) will entrap you!”

Example: I recently received this response after requesting a demo from a software provider.

Thank you and Communications Edge for your interest in learning about our award winning [software tool]!

I am eager to hear from you and what you are looking to get out of your LMS package.

In order to give you a more detailed pricing quote, do you mind answering a few questions:

  • Are you training staff or external partners?
  • If external, will you be selling the courses?
  • How many learners are you expecting on a month to month, year to year basis?

Who says I want — or am qualified to request pricing?

Why would a seller communicate, “I’m going to ask these questions specifically to size-you-up for a quote” before discovering if a price quote is appropriate?

Wouldn’t it make better sense to ask me (a potential buyer), “What is your current LMS solution and/or why would you not build your own LMS?”

Of course it would.

But this solution provider’s rep didn’t ask me that. Because in his twisted world it wouldn’t serve him. After all, I just requested a demo.

I must be ready to buy! Or I’m darned close.

Wrong and wrong.

Those conclusions are both foolish and blindly abundant thinking.

Perhaps you may not think “Why would you not build your own tool?” is smart. But have you considered how this question is neutral? It pushes against making a quick sale.

Therein lies the power. Sound like David Sandler’s “negative reverse” technique? Indeed! It can be very effective.

Effective at qualifying a purchase for both buyer and seller? No. Effective at qualifying a discussion about a potential purchase … if and when the purchase is right for the buyer.

The Role of Questions

The role of questions in effective cold email messages is to serve. The client! In doing so you serve yourself: Clients “qualify-out” themselves. Customers will gladly tell you if they’re going to purchase, when and why … if you will kindly not rush it.

Too often we see questions being used to qualify buyers and/or entrap them. Both cause your email messages to fail or under-perform.

Another rep recently sent this question to me, paragraph No. 1, cold:

“Hi, Jeff. Would you like to increase distribution of your training modules? I am contacting you because I would like to bring [company] to your attention.”

Of course I’d like to, you dope. But then it gets worse … he tells me his intention is 100 percent about his need to place a solution. This isn’t about my need at all. Just to be clear!

First this rep tries luring me with a question that, if I answer, obviously makes me vulnerable to a sales pitch. But just in case I miss his intention he spells it out clearly for me!

The above reps want to sell LMS software to me … more than they care if this is, at all, a fit for me. Prefacing questions with “I’m asking you these questions to push a quote on you” literally screams “I’m going to jam this sale through as fast as I can … game, Jeff?”

In the first example, exploring the nature of my demo request could be saving him time. Time is money. (if you’re this reps’ boss this should trouble you!)

There are a myriad other problems with this message. For example, how does communicating, “I’m eager to show off” benefit me, a potential customer?

BANT Is Killing Us

Rather than a servant leadership mentality (and practice model) there is a pervasive “BANT mentality” (Budge, Authority, Needs and Timeline) dominating sales email messaging. Especially inside sellers.

It’s giving us a bad name, wasting resources and losing accounts.

All by promoting a communications technique which helps customers feel vulnerable to pitches that want to happen way, way too soon.

Help the prospect see your questions as neutral to your bias to sell. In other words, don’t help them feel your question is self-serving. Instead, aim your question at their decision-making process … to spark curiosity.

What is your experience with questions? How are you using them to serve customers and your lead qualification process?

Author: Jeff Molander

Jeff Molander is the authority on making social media sell. He co-founded what became the Google Affiliate Network and Performics Inc., where he built the sales team. Today, he is the authority on effective prospecting communications techniques as founder of Communications Edge Inc. (formerly Molander & Associates Inc.) He's been in sales for over 2 decades. He is author of the first social selling book, Off the Hook Marketing: How to Make Social Media Sell for You.Jeff is a sales communications coach and creator of the Spark Selling technique—a means to spark more conversations with customers "from cold," speeding them toward qualification.

10 thoughts on “Why 97% of Sales Email Messages With Questions Don’t Work”

  1. Good points. Consultant based sales often gets misunderstood. If the title was actually based on the actions it would be reversed. The primary cause of this problem is not setting up your marketing strategy or plan correctly. No matter what situation is presented you should be able to help. It may be your product or service but it may not. The current situation as well as a needs type analysis is the first conversation anyone should have. My product might be the best fit but it may not. If your system is set up correctly you can advise them on what the best product or service actually is. Many sales and marketing procedures attempt and assume you need what they offer. Here is a unique and simple approach. Most inquiries are initiated in the evaluation stage. They are in the process of making a decision. How about creating some marketing materials that help them make a choice? That is what the need at that point. You are giving them what you think they need. This type of approach really defines you as an expert. Most marketers do not address this. It saves sales a lot of time as well. If your product is the best fit then continue the process but if not you are not wasting time and resources trying to convince them your product will work. Yes your product will probably work but is it the best available for their needs? You have to accept that your product is not designed for everyone. If you need help setting up a system that implements these concepts please reach out.

    1. Thanks. “Most inquiries are initiated in the evaluation stage. They are in the process of making a decision.” Mmmm. not sure if that squares with my experience, Wally. I see a lot of software demo requests being made by people who have absolutely no purchase authority and who are not actively considering (yet). Many are still considering “build or lease.”

      1. Agree with software testing . Then marketing should address the advantages of building or leasing. I evaluate a ton of software with no intentions of ever buying it. I want to se
        e if it will be good for my clients and I like to see if it can be a business on its own. Meaning can someone start a business using that software as primary resource in generating income. Many developers never see this model and few really pass the test. But I have never been asked why I downloaded it or tried it. They all assume I am a buyer. I can generate revenue for them. they never ask how.

        1. Good dialog Wally. I see a great need to help people to embrace accountability as in a WEconomy, that connects people and fosters trust and the desire to matter. I also work with software and interactive learning programs but when you look at why companies fear transformation and then make it natural, fun and far more fulfilling, they enjoy the ride of a lifetime. That is what I am doing now. We’ll see how others open up or resist it. But success that pays attention to others first with no hidden agenda’s is really essential. I hate seeing all these folks ask for a connection in social media (which was intended as a sharing environment) and go directly into sales mode.

          1. Thanks. The truth is I know I can help people. We all can. It may not be my product or service though. There are people who are better than me at what I do. There are people who are worse. The fault in marketing is assuming. I cant help you at all until I know what you are looking for. Marketing generally focuses on client acquisition. There are several other areas that often get ignored. If you help a prospect in making a decision, then sales does not have to walk that line as to when to ask for the sale. Yes it may lengthen the cycle but it often shortens it. If you help them gather and review different options they don’t need to so the decision can be made both better and faster. If you structure your marketing correctly the majority of the viable options are with people or companies you have a relationship with.

          2. Hi Wally, Well stated. I loved my career that evolved from design, brand, marketing and strategy in highly demanding industries. Yeah, initially it feels great to measure up to standards set by people we respect, but what’s really exciting is when we leave a comfort zone to embrace a larger shared value. Something we would never see till after we invest in others. Marketing and sale have denigrated to stalking people that search for something once (retargeting) and pushing info at people. I’d rather define my success by the success of others I help. If I can help them with an hour or two of my time, I don’t charge for it. If I cannot help a client after 8 -12 hours of my time, I do not charge for that either. Given my 24 year track record with HP and other tech companies and across all industries, to be a catalyst and strategic implementer that accounted for their highest revenues ever…I can align my offers to higher outcomes and certainty than most. I do this without ego or any hidden agenda’s as all work and life are about enabling and connecting people to work and solutions that matter, even where they initially could not even imagine it before. I wish you luck in your endeavors as seems you have the right value compass.

          3. Actually have a theory that marketing and sales are reversed. In my system it creates an employee advocacy environment because if the targets are set correctly anyone and everyone can both sell and market. They soon find skills they enjoy and are good at naturally. This allows the company to really expand.

          4. Hi Wally, yes anyone can create a better relationship and benefit the company. I still recall when I went to my local supermarket and was in the veggie section and the store clerk pointed me to another store with fresher produce. My point is no one likes to be a target, sold to or marketed to. Sales and marketing go into steep declines when a company falls short of the markets raised expectations of them, now armed with total transparency. That is why I stated that until companies invest in a purpose, inclusion, shared leadership and rewards, trust and relevance…that won’t change.

      2. Maybe evaluation is the wrong term. It is still the decision aspect. Evaluating different options not the actual comparing of products. The fact still remains that the provider has no idea why someone downloads or tests(demo) the product. Some do have some small forms to gain this knowledge but this also creates a friction point.

  2. Hi Jeff, Nice article. Thanks. As one who long worked in design and marketing (nice combination for creative relevance) and earning regard as a customer champion, I often put the corporate agenda as secondary to the real needs of customers, influencers, channels…all within the market and business ecosystem I>E. instead of pushing resellers to sell a large tech companies products, I first helped the resellers to shape brands and strategies that truly helped customers. This pay it forward approach created the strongest reseller growth nationally and yes, they then sold the large tech companies products because we cared to invest in trust and relevance first. I have over 50 experiences like this that led to that companies highest revenue growth and most inspired global teams.

    My work is now geared to inspire greater business humanity as soft skills finally get noticed as crucial. I heard 77% of CEO’s are concerned their employees lack adequate soft skills. Meanwhile Gallup says only 15% of global employees are emotionally connected to their work. That’s a lot of two way blaming going on.

    My point to you and others is that people have always been the difference makers internally and externally. Trust has always been principle #1 along with relevance. As we exit a time where people were measured by their close rates, and customers hate being sold to or marketed to, the very soft skills engineers used to put down as “artsy fartsy or touchy feely” have always been hero work those of us that cared did without reward. Today, if you fail to earn good faith across your internal and external ecosystem, you fail on all counts.

    That said, as one who volunteered for 8 years in an incubator and who took a 3 year sabbatical to study the values shaping change, I see a pattern to develop closed internal cultures that strangle inclusion, innovation, open dialog and outside-in objectivity. At the other end of this equation, the river of change is upon us and if we stay in our bubbles, we will fail to ride those new currents.

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