We’ve all been in situations where we’ve lost a deal and had no clue as to why. I’d just sit there and stew on it, combing through every interaction I had with them, second guessing my pricing, wondering if maybe I could’ve had better executive alignment, or maybe my competitor just flat-out outsold me. It sucks to go through that, but there’s a way to significantly reduce the number of times this occurs and that’s by documenting, tracking, and leveraging your prospect’s evaluation considerations.

What Are Evaluation Considerations?

Evaluation considerations are the factors that the prospect will take into account as they make their decision. Common considerations are price, expertise, location of resources, feature/function, integrations, etc. When your prospect is listing these out, try to get specifics. If they say, “Expertise”, ask, “What specific expertise is most important to you?” Don’t let them get away with giving you high-level considerations. That’s too easy and you’re not setting yourself up for success by allowing that to happen. Details matter.

Whose Evaluation Considerations Matter in the Account?

This is where a Buyer Map comes into play. As a general rule of thumb, if the person is important enough to be in your buyer map, then they’re important enough to get considerations from. In fact, gathering these can be your excuse to reach out to specific people one on one. This serves a dual purpose. Not only are you gathering important information, but you’re also building more relationships (multi-threaded). You can write these people via email and request a call, but that may result in them just responding via email (usually with vague, high-level considerations) or them just not responding at all. I recommend cold calling each person and saying something like:


 “Hey Bob, this is (INSERT NAME) from (INSERT COMPANY). I was going through my notes from our last call and realized I was missing some pretty important information from you. I apologize. As you and the rest of your team evaluate your options, what factors are most important to you, personally? That’s my only question and the only thing I’m missing.”



What does this simple little call accomplish?

  1. It establishes a one-on-one relationship with that specific stakeholder.
  2. It makes them feel special (you taking the time to call them to ask what’s important to them, “personally”).
  3. It gives you invaluable insights into what they’re specifically taking into consideration as they evaluate you as a vendor.
  4. It makes you stand out from your competitors as a competent professional because you’ll come across as thorough and organized.
  5. “That’s my only question and the only thing I’m missing”. This tells your prospect that the call will be short and because there’s only one single question, they’ll feel obligated to share the information with you.

Leaving this as a voicemail is okay as well. I find that I have a >50% call-back rate when I leave a message asking for 10 minutes to cover this and giving them my cell. Also, as you’re writing down everyone’s considerations, be sure to write names next to each consideration and consolidate. If price was important to three people, make sure those names are next to “price” in your list.

What Should I Do With This Information to Better Control My Sales Cycle?


There are three things you should be doing with this information:

  1. Work diligently to validate that you’ve met every single person’s considerations, then check them each off in your list as time goes on.
  2. As you  continue to engage with people in the account, pause every so often and revalidate considerations with key stakeholders. (i.e. “Bob – 6 weeks ago you told me that these seven factors were important to you. I just want to check with you to see if there’s anything you’d like to add to this list now that we’re a little bit deeper in the evaluation.”). When and how often you do this is on a case-by-case basis. Just use your best judgement.
  3. Use it to close the deal in your final presentation! Sample statement during final presentation: “Throughout his evaluation, I’ve been closely monitoring our efforts to ensure that we’re meeting each individual’s expectations. As you can see on the screen, I’ve checked off everything. I’d like to pause for a moment so you can absorb this from two perspectives: One – Is there anything on here that is inaccurately checked off? Two – Is there anything that’s not on here that should be?”

During the final presentation, if there’s a large group I’d stick with the question I suggested above. If it’s a small group of 2-3 people, I’d change up my positioning and ask that each individual respond: i.e. “Sally, from your perspective, is there anything on there that is inaccurately checked off or is there anything that you feel is completely missing?” Then, “Bob – How about you?”

In summary, while I know this is a time-consuming exercise, it’s absolutely worth it and will significantly increase your chances of success in the deal. In some cases, if people aren’t willing to spend the time with me to tell me what they’re considerations are, I’ll use that to test the validity of the deal by saying something along the lines of, “We know that 72% of prospects that don’t have documented considerations don’t end up making purchases. My company won’t let our sales department leverage any internal resources until these are documented. Having said that, are you willing to schedule some time with me to go through this or are you okay with us respectfully declining to participate in the evaluation?”

Now, I won’t use that in every deal, as it’s a little harsh, but if I feel like my time is being wasted or they’re not taking the evaluation seriously, this is absolutely the right path. If they get pissed off and are okay with you walking, so be it. You just saved yourself potentially weeks/months of wasted effort. Hell, they may even come back to you later at which point they know what they’ll have to do to work with you. It’s a win/win for everyone involved.