Time to Sweat the Small Stuff: Part 1 — Minor Failures that Condemn Sales Presentations to 2nd Place

Having recently worked with procurement on a multi-million dollar outsourced contract, it was fascinating to see sales teams’ minor failures have an oversized impact on evaluators’ decisions. So here are the first three of nine failures that made a difference (the remaining six will come in following posts).

There is a time to sweat the small stuff.

It’s when you’re on a sales team that’s about to make an in-person presentation for a large dollar contract; every action should be intentional and orchestrated.

At this stage, the smallest misstep can turn off the evaluating team and effectively blow what you’ve accomplished so far.

If evaluators have invited you to present in the down select, then you know your offering (and pricing) is in the ballpark. And, in presentations it’s the little things that can swing the decision in your favor, or have you standing on the number 2 podium with no contract. Now is the time to prepare for and avoid these presentation failures.

Presentation Hubris of Experienced Sales Reps

Unless of course you like to wing it, which is the hubris of many an experienced sales leader, and you can hear their excuses after a botched presentation:

  • “We’re sales veterans, we know what to do, we don’t need to prepare”
  • “We didn’t have time to prepare”
  • “We couldn’t prepare because everyone’s in a different city”

However, for savvy sales pros here are fine points that you DON’T want to do. Avoid them and you’ll make a better connection with evaluators during your presentation, which allows them to better hear what you have to say….AND…. better find the relevance and value in what you’re saying.

It’s all in your understanding and preparation.

#1) Don’t Intimidate with Numbers

#1) Don’t Intimidate with Numbers

And we’re not talking about pricing: This is about the number of people you bring to the presentation.

Keep your sales team fewer than the number of evaluators in the presentation. If you don’t, it may look like you’re trying to invade Poland.

How many on your team is the right number?

There’s not an exact number but in my experience the sales team works best if you have two-to-three (2-3) FEWER members than those in the room evaluating your presentation. For example:

  • Evaluators =5 —> then your sales team = 2-3
  • Evaluators =7 —> then your sales team = 3-4
  • Evaluators =1 —> then your sales team =1

If there are remote evaluators sitting in via web meeting, you’ll still want to keep your sales team’s number fewer than the evaluators in the room.

Get it wrong and this is where it’ll hurt…

Get it wrong and this is where it’ll hurt…

If you have more people on your sales team than evaluators, even if you’re team is holding quietly on the web meeting, you can create an oppressive atmosphere. Like vultures on a telephone line waiting in turn to swoop down onto roadkill.

And when your presentation time gets tight, if you have lots of team members they may feel compelled to gabble at speed to force words into a closing window. Remember, evaluators know you’re time’s about up and they’re starting to shut down in preparation for the meeting’s end. And no one’s consciousness can handle this type of data dump after just sitting through volumes of information.

#2) Don’t Mismatch Their Team

#2) Don’t Mismatch Their Team

One of the determinations evaluators try to make during your presentation is can your firm, as an outsourced outsider, work within their culture. And that covers many areas, such as:

  • Workplace courtesy & manners
  • How conflict is dealt with
  • Diversity in thought & people
  • Dress codes & personal appearance

Assessing your cultural fit with their firm is always a gut call; it’s the evaluators’ best guess during the presentation.

If you signal you’re aligned with their company culture it can add an unspoken connection between your sales team and evaluators.

However, if not, it can highlight a perception of unfitness between you and them, a “Can’t quite put my finger on it but I just don’t feel they’re right for us” type of response.

Many sales teams look for every advantage when competing for large dollar contracts. Cultural alignment will be one of them. Realize your competition may be addressing this to their advantage.

Matching the Evaluators' Team

So, to whatever degree you can, match your sales team’s dress code and demographics with those of your evaluators’ team and their company culture. Give it your best shot, recognizing this is one presentation goal you may not fully achieve.

For example, if your evaluators include one or more millennials, your sales team should include at least one. Same is true with race, ethnicity, and gender to whatever degree you can with the people you have, which speaks to having a heterogeneous team yourself. And of course, your team should dress to match the evaluators and their culture.

1st BIG CAVEAT to Mismatching Their Team

Populate your sales team ONLY with members who will add something to the conversation — never bring people in the room for a false display. Evaluators see through it in a second.

Also, don’t feel pressured to get tattoos or visible piercings either. Matching clothing and demographics is good enough. Seriously!

2nd BIG CAVEAT to Mismatching Their Team

OK, if your sales offering is acknowledged by all as over the top valuable, bleeding edge cool, and you’re the only game in town….Well, then you dress how you like, bring who you like, and basically make a statement that this is who you are: “The hell with anyone else, take it or leave it.” And good luck to you too.

Get it wrong and this is where it’ll hurt…

Get it wrong and this is where it’ll hurt…

Mismatch this intangible and it can easily have an oversized impact on evaluators’ decisions. This risk is even more impactful in culture-conscious tech firms on both coasts and in between.

Ever watch a team of 15 suited, middle-aged, white men, hedge-fund manager lookalikes walk into a sales presentation to face six evaluators who are a youthful mix of genders and race wearing hoodies, polo shirts, and jeans? (I did. My group followed that mismatched sales team and the evaluators certainly told us all about the mismatch. Luckily, we were aligned.)

#3) Don’t Forget to Acknowledge Each Evaluator’s Importance

#3) Don’t Forget to Acknowledge Each Evaluator’s Importance

Procurement almost always includes end-users and gatekeepers on their teams to evaluate sales presentations.

End-users are there to check the reality of solutions presented. They’re often front line managers on their way up a career path, and evaluating these presentations helps broaden their experience.

Gatekeepers are there to make sure the solutions presented pass muster in secondary areas, such as compliance with safety, legal, HR, finance, etc.

Expect end-users and gatekeepers to be proud of their role in the company. Watch how they introduce themselves at the beginning of the presentation when they state the part they’ll play with this purchase. You’ll likely see joy and a sense of pride for being a part of this important decision.

Savvy sales pros during the course of the presentation typically focus on the end-users, working to get them to acknowledge the efficacy of the proposed solution.

Don't Forget the Gatekeepers

Flickr CC image by krollia

But don’t forget the gatekeepers. While they may be nominally involved with the solution after purchase, they’re customer-insiders that you and your sales team will want as allies during the contract term.

So, without obviously pandering them (flattery apropos of nothing), subtly and selectively acknowledge the importance of the position/role of every evaluator present.

For gatekeepers, articulate how your solution will make compliance, governance, and reporting faster, easier, and better for their work domains. How it will make them and their department look better to their execs upstream.

For end-users, continue to elicit their understanding and recognition of your solution’s value, just like you’ve always done.

Get it wrong and this is where it’ll hurt…

Get it wrong and this is where it’ll hurt…

The funny thing about evaluators; their titles don’t always equate to the influence they have behind closed doors. It’s like a courtroom jury, where an outspoken, large-personality janitor can have more gravitas than a bank president, with the ability to sway the rest of the jury towards their opinion.

Ignore a gatekeeper during the presentation at your risk; to some it’s a sign of disrespect. Recognize it’s difficult to know when a gatekeeper has the personal power to sway what seems a logical choice in another direction entirely. You and your sales team don’t want to be on the losing end of that one.

Flickr CC image by New York National Guard


These are the first three of nine failures to avoid in sales team presentations. Presentation prep is the time to sweat the small stuff so prepare accordingly. And please, don’t fail in these three small areas:

#1) Don’t Intimidate with Numbers

#2) Don’t Mismatch Their Team

#3) Don’t Forget to Acknowledge Each Evaluator’s Importance

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