Creating Situational Awareness in the Technical Sales Process

I recently came across this blog from Gartner Group’s Hank Barnes on the subject of creating situational awareness inside the sales organization. This plainly has a direct corollary inside the SE organization so I thought it would be good to think about how we could apply that to our own deals.

In order to keep this a manageable amount of information, I decided to list out the top three questions to ask yourself for each step in the technical sales cycle.


  • What are the top three most important data points you need to qualify a customer? Some customers may be very open and willing to describe all aspects of their pain points and buying process, others will hold that information very close to the vest. Try having a question or two at the front end of your 1st meeting to determine how much information you can obtain. Something like “Can you tell me about how you’ve been accomplishing xyz today?” If you get a great response, perhaps you continue with a few more well rehearsed questions.
  • How can I incorporate qualifying questions into my pitch? If and when you meet the brick wall, go into your material, but have strategic checkpoints during your pitch where you may be able to pull out some related qualification material. For example, if you’re talking about network architecture or sizing, a question about how many potential users they would have seems like a very appropriate question to ask, and one that would likely be answered in that context.
  • What are the top three red flags that you could help uncover during your first meeting? Is there a specific use case you’re weak at or is a key buying center not represented? Figure out what these are ahead of time and make sure you’re seeking these out immediately.


  • Would slideware or a whiteboard be more effective? Most customers do not mind slideware as long as it’s interesting. Others are put off by the very nature of slide- based presentation. Think about asking the question before you delve into presentation: “I have some slides that are already complete that I can put up to talk through, or we could take a bit longer and do a whiteboard session that would be more specific to your organization, do you have a preference?”
  • Who in this meeting am I addressing the most? The least? Asked another way, you’re simply prioritizing attendees and the specific content likely to be most important to them.
  • What objections do I need to spend time addressing right now and which ones should be dealt with offline? There are likely certain aspects to your product that come up repeatably as objections. Determine which ones are most important to your prospect and which ones are tangential that can be safely taken offline.


  • What are the three most interesting elements to this prospect I need to ensure are included? Make sure you’re showing the most relevant aspect up front (ala Great Demo!)
  • Do you have the minimum necessary information required to provide a customized demo? If not, make sure you ask those final questions up front before you begin.
  • What are you closing for? Sometimes multiple demonstrations are required. Oftentimes the POC is the next logical step. In others, a reference sale may be appropriate. Understand what you’re closing for so that 1) you cover just enough ground to set yourself up nicely, and 2) you incorporate your close as part of demo meeting.

Proof of Concepts

  • What other solutions are going to POC? Competitive angles can be used throughout the sales process of course, but at this stage it is imperative you factor this into planning. This influences the testing below.
  • What are the pertinent use cases for my prospects business pain point? Rarely does a prospect really need all that product does (or every feature within it). For each POC at least have a mental list of what is needed to cover. Leave out everything else to avoid scope creep.
  • What test cases accurately demonstrate the use cases? An important component of every POC is figuring out how you recommend a prospect test out a particular use case. I say recommend because a prospect may have their own plan, which is fine, but you should always try to influence this. It will save both of you a lot of time and effort.

Are there others you’d recommend for this list? Comments here.

Don’t Be This Guy


Click for larger image

While I have gone through a fairly rigorous set of writing/grammar classes in the past, I don’t consider myself a grammar nazi. Those who live in glass houses and all…

But there is a definite time and place to ensure that your communications (both verbal and non) are crisp and as perfected as possible. When I was just getting started in my professional career I would sluff off comments that a slide or email communication had some spelling or grammar errors. After all, when I sat through presentations they didn’t bother me at all.

As you meet with more and more customers you will eventually come to realize that there are those that 1) notice, and 2) care a lot about these things. Even folks like myself that are pretty lax start to raise an eyebrow if there are more than a couple errors in a slide deck.

And there is one group/situation in particular that should be hyper sensitive to accurate communications: managers and those helping screen applicants for job hires.

Enter: This Guy


Normally I don’t like to pick on individuals for posts, but if there was EVER a time to use proper language, it would be from someone asking for a job contact. Recruiters/HR are paid to find reasons not to send your resume along. Don’t make it easy for them!

What we should all take from examples like this is that people perceive us by the words we use and how we use them. Take the time to scrub your presentations, or better yet have a fresh set of eyes do it. Take the time to reread that important email a few times to make sure it’s perfect. Take the time to rehearse the beginning and ending of that important presentation. And, most importantly, be extra diligent when communicating with anyone who may have a say on whether you’re hired.

Comments here.

Why Google Sucks

googleWhen I first got started in this business you really had to know your stuff cold. That meant that you couldn’t rely on every possible answer to a technical question being just a Google search away. I was, just like our customers, forced to memorize a lot of pedantic technical data.

I recognize this has a sort of “get off my lawn” sort of overtone. But you know what, I’m really glad in a way. Today, it’s all too easy to rely on the Internet Crutch to answer our questions on demand. Temptation is everywhere, and for up-and-comers to high technology this represents a real problem.

This problem is especially pronounced for SEs. You only get a few hall passes per meeting where you can answer “I don’t know, let me get back to you on that” before your credibility is damaged. There is palpable pressure to know it all without coming across as a know-it-all. I think I can help you with the first part.

I recently found myself involved in a similar version of this conversation with a colleague for the nth time. It seems to come up A LOT. Every time I find myself making a similar recommendation, and goes something like:

“There’s a book I read a while ago–actually a gift from a family member–that had a really great impact on my ability to remember and recall all sorts of information I find important, especially names, acronyms, and technical data.”

At this point folks get pretty interested, mainly because I think it’s a very universal skill we all wish we were better at. The book is Moonwalking with Einstein: The Art and Science of Remembering Everything. It recounts the author’s journey from covering the World memory Championship as a journalist through his experiences becoming a participant.

It is beyond this article to cover all of the techniques discussed, but suffice it to say it spawned my reading of several other books on memory development. The key takeaway: Memorization is skill like anything else, nothing more–the implication being that anyone can learn to have a fantastic memory. It may not help you remember where you parked your car at the airport, but if you want to learn the name of all the countries of the world or remember those OSI layers, this is the place to start.

So the next time you catch a colleague trying to justify why they didn’t memorize something (instead preferring to “Google-it” as needed), please send this link, they’ll be glad you did.

Comments here.

When All (Attention) Is Lost

BoredHave you ever made it several minutes in to your presentation only to feel like your prospect couldn’t care less what you had to say? I experienced that (thankfully rare) feeling the other day while my rep was presenting the opening to the call. It’s tempting to just blame the prospect and assume they aren’t interested. But here’s the thing:

They took time out of their day to speak with you. They MUST have a problem.

Once you realize that, you realize that you must have strayed somewhere in your pitch. You lost them for a reason. And that’s ok, it will happen occasionally to everyone, but you have to be mindful to get yourself back on track. First though, could you (or your rep) have prevented that issue in the first place?

  • Did your “hook” email promise something compelling, but you didn’t hit on any of those points at the beginning?
  • Did you assume you knew the customer’s problems and started down your normal spiel without verifying?
  • Did you waste 15 minutes of this poor soul’s life showing them several slides about your company, your customers, your awards, pictures of your corporate headquarters?
  • Did you not properly introduce yourself such that you had no credibility established from the start?
  • Did you not take a minute before unleashing your slides to attempt to build a bit of personal rapport with the audience?

And how do you know if you’ve lost attention? The most influential aide is simply paying attention while you’re speaking, and more importantly while your counterpart is speaking. Here are the things to watch for:

  • You hear them typing in the background
  • They have to unmute when you ask them a question (because they were smart enough to know you’d HEAR them typing in the background)
  • They decline to answer questions or they provide one word answers
  • They gave themselves an “out” somewhere after the call started (such as an urgent phone call they have to answer)

So you’ve taken care of the basic hygienics of managing attention, and you notice that attention has faltered, how do you get back on track?

  • Throw out a difficult or somewhat contentions question, something specific to your industry where everyone is likely to have religion on their point of view
  • Pause, and ask them sincerely if this is hitting the mark because “you’ve got a sense” that they might rather want to focus on architecture, or the competition, or a demo, etc.
  • Do the unexpected. Stop your PowerPoint. Cut to a story about an existing customer. Make a joke: “So, Dan, it seems like you totally get it, should we stop now and talk about a PO?”

The option I chose on my call last week was a combination of a touch question and something unexpected. I stopped my rep politely, suggested that it seemed like my prospect already had the problem solved, and suggested we should conclude the meeting if that was the case. In a very complimentary way of course.

In this case I was lucky: the prospect woke up, felt slightly challenged by the assertion, and then took five minutes to explain why he did in fact need a technology like ours. We responded by ditching the rest of the presentation, went right into a demo showing the use case he discussed, and the call ended on a high note.

I should point out that something like that is a last ditch effort, because you run a small risk of alienating a potential buyer. But, then again, based on verbal cues you probably weren’t reeling in a big fish either. Having thought it through, I realize now that my reps and I should have some phrase that signals the other that we need to shake things up, which also gives them the chance to veto that decision. Meaning, both of you are on the same page before attempting.

If nothing else, that should prevent the “WTF?!?!?” phone call after the meeting.

How 8 Determines Your Fate

downloadThere is now research to prove that humans, on average, have shorter attention spans than goldfish. Really. It is now just 8 seconds. That is a 33% drop since 2000. And for the folks we are all trying to reach (the “decision maker”) that span is probably shorter. Knowing this, what can we do increase attention on our offering, and most importantly have that knowledge retained?
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Does Anyone Have Any Questions?!?

Does this sound familiar: You’re going through your presentation or demo, you get to a transition point, you pause, and… crickets. So you ask “does anyone have any questions?”. Nothing, or maybe an uncomfortable “not right now”, comes back. So you try that again, this time maybe you don’t wait so long until asking again. Same response. Rinse and repeat this cycle 5 to 7 times and you have a very common affliction that affects many of us.

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The Inside Job

I’ve been catching up on some past seasons of a pretty good crime show called White Collar. It’s got a lot of Thomas Crowne overtones to it. One of which is that while external heists are some of the flashiest of crimes, the inside job is less dashing yet often more elegant and effective. It got me thinking about some of my bigger successes and what separated them from lesser performances. In almost every case I could point to having a good inside man with the customer. In most circles they are known as Champions (as in they champion your cause). As SEs we should be especially mindful of creating, nurturing, and enabling ours to be successful. So in this article we’ll look at some processes and best practices around doing so.
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