Why are so many sales presentations like bad dates?  And how do I fix this?

Why are so many sales presentations like bad dates? And how do I fix this?

I recently spoke with a CRO who’d taken their company from $5M to $200M+ and shared my belief that most executive-level customer pitch decks fell flat and could be 10x more effective. He challenged this (as I'd hoped) and the ensuing discussion was fun for both of us. I’m recounting it here in case it’s helpful to other marketing and sales leaders. You can apply this to pitch decks or any presentation where you want to sell your vision and convince your audience you’ll achieve it. 

The analogy that brought our conversation to life was comparing dating to pitching a customer.

When you go on a date, we’ve all learned that you start by learning about the other person:

  • Where do you work? What do you like about it? What’s missing?
  • What are your favorite things to do in your free time?
  • What do you wish you could do that you aren’t today?

The purpose of all this is to be able to identify the things you have in common and see if you find each other interesting enough for date #2.

Yet compare this to how many companies pitch executives at new customers. Here’s the flow I see all the time:

  • Here’s a picture of our founders 10 years ago when they worked here.
  • Here’s a picture of our headquarters building. It looks expensive, but our products are well priced.
  • Here are our products and technologies in great detail – speeds, feeds, block diagrams and a roadmap of things you can’t have yet.
  • Here is a slide with all the companies that buy from us including some of your competitors.

I’m sure you can see parts of this in your own presentations. Now imagine for fun if you behaved this way on a date. It would look something like this:

  • Here’s a picture of me on the college swim team. Yes, I’ve changed a bit.
  • Here’s a picture of the house I grew up in. Mom and Dad did well, but OK if we go Dutch on lunch?
  • Here are all the things I like to do in great detail, starting with pictures of each car in my model train collection.
  • Oh, and here are some of the other people I’ve dated or am dating.

It’s basically a conversation about me, me and more me. It’s no wonder so many customer presentations are like bad dates. Sure, the salesperson may have done a great job qualifying the customer. But this is all wasted if the way you present to the customer is all about you.

Pointing out problems is easy, so the CRO naturally asked: “so what’s the right way to do this?”

Here are the five steps I use to lay out an executive customer presentation (and most others in some form). Much of this comes from things I’ve learned and plagiarized from great sales and marketing leaders over the past 20 years:

1.    Start at a market level

It may seem counterintuitive to not start talking about the customer’s needs. But it’s important to start bigger to show you have a strategic view of the market. The market-level view should identify a macro issue that is important to your customer and in which you have expertise. Show how it is important and that those who move early will gain advantage. Show that those who do not move early stand to lose something. Create urgency to take action.

At this point, you haven’t talked about your company, its products, or the customer’s specific needs.

Desired outcome of step 1 of your presentation: the customer sees you understand the market today and have a long-term view; you’re a potential partner and not just a vendor. You’ve put their short to mid-term problems into a larger context, made them more important, and potentially created a larger opportunity. And you’ve learned more of their needs through discussion.

Examples of market-level entry points: this is the hardest part of the presentation to get right and will take some trial and error. Here are a few examples from my past:

  • From the CAD and 3D design market: today we’re going through the biggest change in design since CAD moved from 2D to 3D in the 1990s. How will this produce new winners (and losers)?
  • From the security market: No matter how much companies invest in security technology to build taller walls around their infrastructure, people/employees are the source of most breaches. If building more walls isn’t working, how do we address the people part of the equation?
  • From the PC market in the 2000s: how will the PC remain relevant as the DVR and game console take over entertainment and the living room?

2.    Identify a joint obstacle

If you’ve done your job in step 1, the customer sees a big opportunity. In fact, they may have seen parts or all of it on their own but been unable to capitalize on it. This could be due to a lack of resources, in-house expertise, or something they just don’t know how to do.

You have still not talked about your company or its products.

Desired outcome of step 2: identify the obstacle to capitalizing on the market level trend. Through preparation, you already know what this is. You want to exit step 2 with the customer seeing you as their potential partner who is invested in overcoming this same obstacle.

3.    Tease a solution

The important word here is “tease” - you want to show just a bit without diving into all the details. This is hard to do because we all love our products and want to talk about them. But completing step 4 first will make the product discussion much more successful. An example of a good tease is 1-2 slides or 3-4 minutes where you say: we’ve broken down the obstacle into three components and have a high-level approach to addressing each. The three components here should be the three pillars of your value proposition and frame the solutions and products you will eventually talk about.

You have still not talked about your company or its products.

Desired outcome of step 3: you want the customer to know you have an approach to meeting their needs, invested in the rest of the meeting, and leaning forwards in their chairs. 

4.    Share tons of customer evidence

I usually start this step by saying “let me show you some best practices for how we’ve worked with other companies to address these same challenges. I think this will bring things to life and give us ideas on how to proceed together.” 

You then show you already have expertise and success in helping others capitalize on the market trends from step 1 and overcome the joint obstacle in step 2. And ideally, your examples illustrate how you’ve addressed each of the solution components in step 3. 

It’s best to show vs tell, so leverage video demonstrations, live demonstrations, and customer testimonials. Bring in data everywhere you can with an emphasis on the kind of data that will help the customer build their business case to work with you.

In this step, more is more. 

You are still not talking about you or your products – you are talking about what others have achieved (with your products as the supporting actor vs the lead).

Desired outcome of step 4: you want the customer or audience you are speaking with to come away knowing you can already help them. Others are already using you successfully. And others may be moving faster than they are. Ideally, you want them to want to move faster, skip a trial phase, consider a larger engagement than they had been, and know your products are solid.

5.    Frame the joint solution

You are almost ready to talk product, but not yet. Resist the temptation to lay out your products like all the items on an a la carte menu. You have been solution selling to this point and want to deliver the six-course tasting menu (with wine pairing) rather than one or two items.

You want to start by saying: here’s how the leading companies I showed you in step 4 got started, and here’s a solutions approach to help you go fast and be a leader in this space (capitalizing on the market trend from step 1). Show the customer three phases to success, or a Large and Medium approach to gaining leadership. These phases should ideally combine multiple products, support, services and consulting.

You may still not have talked about product in detail yet. That’s fine. This is the topic of your next meeting.

Desired outcome of step 5: you want to conclude with executive sponsorship and a clear next step with people assigned to work with you to define a joint solution. Here you will break the phases or proposals down into products and services.


At the simplest level, a customer presentation (or any presentation) done right is about the person or company you are speaking with and the things you jointly care about. It flows more like a date than a typical sales pitch. It’s definitely more work to build out steps 1-4 in my approach vs just launching into a “me, me, me” presentation. But it will create bigger results for you whether you are just trying to inspire an audience, create a partnership, or 10x a deal.

Jeff Hansen

Golf CTO | Venture Partner | Start-up Advisor | Former Founder | Spatial Computing (fka 3D/XR/AR/VR) Gladiator | Former MSFT, Unity, Magic Leap, Belkin, Skullcandy

4 年

Great post and guidance. I learned from the Pro directly!

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Stephane Imbert

Entrepreneur & Investor (Metaverse and MedTech)

4 年

So refreshing ... having a ??date?? with my customers will never be the same ;-) thank you Tim !

Olivier T.

Senior Product Manager Automotive

4 年

Great way to break it down in a simple way. No wonder why I always felt that you should be in charge of the marketing customer docs & sales decks :)

Eva Poppe

Driving Revenue Growth & Market Expansion @DTN | Customer Excellence | Impact Creator | B2B SaaS | Co-Chair Alumni Council Cultural Vistas

4 年

What a great read, Tim. Absolutely nailed it.

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