This one question led to millions of dollars in sales

The secret is in how and when you ask

Over a five year period, I worked in the B2B SaaS space selling to technical buyers who are very sophisticated in the buying process, very knowledgeable about the technology they’re interested in buying (they do a ton of research before you ever walk in the door), and for the most part loath salespeople (I’m still not sure why but it’s a real bias that exists). During that time, directly and indirectly as a sales manager, I closed $15.4 million in annual recurring revenue, averaging out to about $3 million each year. With an average quota for an Enterprise Account Executive (AE) at $1.5 million per year, averaging at 2X quota capacity means not only working hard but also working smart. Let’s discuss the working smart piece.

Selling to a technical buyer can be pretty difficult. An Account Executive needs to be fairly technical (almost as technical as a Sales Engineer), needs to shed the Slick Rick personality, and genuinely needs to care about understanding the problem the buyer is trying to solve to learn if their solution can actually meet the needs of that business. Being inquisitive and asking the right questions will go a long way to building credibility and ultimately closing the deal. But what are the right questions to ask and how does one stay sincere and credible?

The foundation of the key question is “Why do you ask?” This question in itself is not super novel. In fact, it’s basically Sandler Rule #12 — Answer Every Question with a Question. However, next time you’re in a sales meeting with a prospect, study the AE leading the meeting and see how many times he/she just answers every question the prospect asks. You’ll be amazed how many people do this based on society’s predisposition to answer a question when asked (I blame it on the education system). 

As a sales manager, I personally made it a requirement for all the interviewee’s to track how many times a candidate would answer a question with a question during the mock pitch session. If they didn’t or only did seldom, everyone in the room knew where that candidate would end up. Around 90% of the time, the candidate didn’t make it past the mock pitch and as you can imagine, my team was very slow to hire.

Now, Sandler Rule #12 explains why this is important in general but why is this so important in the technical sale? It’s important because technical buyers want to have intelligent conversations with knowledgeable people in the space who have a credible perspective on the problem they’re trying to solve. To get to an intelligent conversation, the AE needs to fully understand all the context, variables, and dependencies that is leading this prospect to investigate a vendor for this solution. Most often technical buyers can solve a problem with enough time and hours but it’s usually not the most efficient or scalable solution. To understand those details, responding with a simple question can open up the floodgates which will lead to a sophisticated dialogue and ultimately reveal the true pain the prospect is trying to solve and, just as important, the concerns they have with your solution! Here are some suggestions that don’t come across patronizing or elementary:

1. Good question! Is there context around that question that could help us better understand what you mean?
2. Can you provide a use case or example where answering that question positively would solve a pain point or business problem?
3. Are you asking that question because you’ve felt that pain before? If so, when was the last time, and what was the impact to the business?
4. You’re asking this for a reason, did you personally have that challenge in the past or did you hear that could be a challenge from a colleague or friend?

Of course, these are just a few suggestions and if all else fails you can simply say, “Why do you ask?” I recall back in 2010 I was giving a pitch to a room full of executives at a speaker company and one of the guys turned to the group and said, “What’s with this guy, every time I ask a question he just asks a question right back.” I looked down and smiled as I knew  I was on the right path.

When to deploy this tactic is critical but here is the first step. Create a trigger in your brain. Yes, I’m serious. Train your brain to recognize when someone is asking you a question. Good news is this only takes about 90 days or so. I’ve personally been doing this for years and yes, my wife still loves me! Do it with everyone at first, focus and pay attention when someone is talking to you and learn to set a mental trigger so if they ask you a question you immediately respond with simple phrases like “Why do you ask?” or “You must be asking for a reason.” Eventually, it will become second nature and you’ll find yourself both recognizing when someone is asking you a question and controlling whether to reply with a question or just answer (asking someone why they asked where the bathroom is probably not the right etiquette).

Once you’ve mastered control over your urge to “ask why” it’s time to deploy this tactic in a prospect meeting. Be sure to use this method strategically to spark a conversation that will lead you down the right path. Over time, you’ll start to recognize themes in your space where asking a question at the right time will naturally lead your prospect down the right path but this does take a bit of time and a bit of practice so don’t beat yourself up if it takes a couple of rounds to get this part right.

Overall, the goal is to get the prospect to pill back the onion and uncover the real challenges they’re having and why they’re asking the question on the table so that you can earn the right to present your solution as the most viable option.

Once you’ve fully understood the question and walked them through how your solution would solve it, you’ve now earned their respect and can proceed with whatever sales methodically your company subscribes to whether that be Command of the Message, The Challenger Sale, etc. with the other side of the table willingly (and usually happily) participating in the process. All too often I’ve observed AE’s going straight into a MEDDPICC barrage of questions before ever earning the right to ask these questions and watching the prospect just give generic, bland answers they know will quickly end the meeting so they can move on with their day. This obviously doesn’t lead to closed:won happy customers.

Here is a bonus tip: I personally always like to close out any meaningful dialog with “Did I answer your question.” More times than not, the prospect would say yes and I would immediately follow-up with “Great, was the answer to your satisfaction?” Every now and again I would get an odd/surprised look but most often I’d get “yes, to my satisfaction.”

I asked this “to your satisfaction” question for two reasons. One, because anyone can answer a question but it doesn’t mean the person receiving the answer is happy with your reply and if they’re not, this opens the door for them to say “well, not really” and now you can continue to pull on the thread. Second, if they are happy with the answer, everyone in the room subconsciously knows it’s time to move on to the next topic on the agenda. Running an efficient and effective meeting is still the responsibility of the AE and if not managed properly, you could talk the entire time and never move the sales cycle forward. It’s a fine balancing act of course, but ultimately your job is to meet the needs of the prospects and convert them into a paying customer.