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.