Using Personality AI to Pitch Pricing

When you use Personality AI to tailor your communication and address costs in a way that accounts for the buyer’s core motivations and preferences, you can avoid mistakes and solidify strong long-term customer relationships.

Fixated on cost

For most people, fewer things create more anxiety than conversations about money. This tension comes at intermittent milestones in your personal life, like when you want to ask for a raise, take out a loan, or negotiate to purchase a house. However, sales professionals have these delicate conversations daily, so if you are in that role, you need to become comfortable with them in order to succeed. 

A few months ago, a VP Sales friend of mine reached out to me for advice on product pricing after dealing with a prospect at her business. This prospect, who we’ll call Todd, was particularly insistent on negotiating pricing for the software product my friend’s company was selling. Despite the fact that she had already offered a discount for paying annually and for purchasing licenses for several members of his team, he seemed determined to get a better deal, for no clear, specific reason. They had multiple discussions, attempting to justify their pricing model, but after a while, it began to feel like nothing she did could really make a difference or close the deal unless she just dropped the price, which her company always avoids doing.

Concerned that she may have overpriced her product, she reached out to other prospects, customers and friends like me to get feedback. Most of us validated her initial assumption: the price is relatively low and the product has a lot of value. So why was her prospect, Todd, so determined to push on the pricing?

Why are some people just naturally more focused on driving down costs, while others are not?

While any given buyer’s individual circumstance certainly impacts their motivation to negotiate, much of it comes down to their personality. Some people have a natural inclination toward efficiency, cost, and value, and they will do whatever they can to increase their return on investment. Others are innately more big-picture focused, driven mostly by new ideas, relationships, and gut instincts, making them less concerned with the details about a deal and more focused on the high-level outcome. 

By learning to identify the different motivations and preferences that drive each personality’s behavior during pricing discussions, you can successfully make sales hooks, navigate these conversations, and avoid getting stuck in a stalemate (much like my friend was with Todd). To do this, we need to understand more about personality.

Understanding personality

Historically, the only way you would be able to fully understand someone’s personality is by either getting to know them really well, which takes lots of time and emotional intelligence, or having them take a personality test. Both of these approaches require that you have an established relationship with the person, which doesn’t tend to work in the world of outreach communication, since we are often trying to connect with new people who we have never spoken with before.

Thankfully, there is a new technology that unlocks another way to learn about someone’s personality without an assessment - Personality AI. We wrote about this in detail in another ebook titled, Personality AI (which you can download for free). This new technology analyzes publicly available information on websites like LinkedIn to predict someone’s personality, using artificial intelligence and machine learning. We built our product, Crystal, to harness Personality AI and enable anyone to identify personalities online to improve their communication and build stronger relationships, all based on the core principle of empathy.

Without getting too technical, when Crystal’s AI predicts personality, it uses a framework called DISC to classify personalities into a few categories that we refer to as D (dominance), I (influence), S (steadiness), and C (conscientiousness). Each of us has a primary DISC type in one of these categories and sometimes a secondary DISC type in another. To keep things simple, we separate these into easy-to-remember labels called Archetypes. 

You can see them all on this graphic called the Personality Map:

Below is a breakdown of common personality traits within each of the categories in DISC.

 D Personality Types: Captains, Drivers, Initiators, Architects

  • Motivated by control over the future and personal authority
  • Tend to prefer instant, concrete results and having an advantage over competition
  • Communicate clearly and succinctly

I Personality Types: Influencer, Motivator, Encourager, Harmonizer

  • Motivated by innovative, unique, creative ideas and excited by the future
  • Tend to prefer building new relationships and experiences
  • Communicate in a casual, expressive way

S Personality Types: Counselor, Supporter, Planner, Stabilizer

  • Motivated by peace, safety, and others’ wellbeing
  • Tend to prefer security, reliability, and trust
  • Communicate in a friendly and genuine way

C Personality Types: Editor, Analyst, Skeptic, Questioner

  • Motivated by logic, information, and problem solving
  • Tend to prefer accurate information and quality solutions (quality over quantity)
  • Communicate in a business-like, fact-based way

These differences are extremely important to understand when approaching a conversation with anyone. For example, someone who is a warm, people-oriented Supporter (S) is less likely to engage in a discussion about facts and data. They’d usually prefer to engage in a more personal, get-to-know-you conversation. An Analyst (C), on the other hand, tends to enjoy learning more about specific, concrete information. By identifying someone’s personality type, we can learn how to best communicate with them.

Why change how you pitch pricing based on personality?

Screen Shot 2019-08-07 at 10.46.58 AM

In the same way that personality impacts the way we think about making plans or working through conflict, it also affects how we think about details like pricing. Discussing cost in the wrong way or at the wrong time can easily lose you a sale. The same applies to other money-related issues, like discussing salaries or raises with employees. While some people are very direct and expect to talk through financial details immediately, others are likely to be offended if you address money-related topics too quickly.

By understanding personality and using Personality AI to improve your communication skills, you can be prepared to better handle challenging cost conversations.

How to pitch pricing to anyone

Addressing D-types:

Direct, assertive D-types tend to prioritize key factors like pricing and will likely want to be presented with information up front. When communicating cost to D-types, don’t tiptoe around the question or hesitate; instead, give a clear, bottom line price. If you spend too much time engaging in small talk or overloading them with detailed information about your product, they are likely to lose interest and you are less likely to move the conversation forward.

If you’re discussing pricing with a D, try saying or writing…

  • Would you agree to this?
  • Here’s how our pricing stacks up against our competitors...
  • What kind of ROI are you looking for?
  • Here’s the bottom line cost...

D Personality Types   Captains, Drivers, Initiators, Architects 


  • Allow some room for them to negotiate
  • Compare your pricing with competitors
  • Show how they can save more money in the future
  • Give them the bottom line pricing without going into details


  • Give in easily when they push back
  • Take a long time to follow up with requested information
  • Wait a long time to share the total cost
  • Make them feel trapped with long-term commitments

Addressing I-types:

Creative, enthusiastic I-types usually want to be connected to the idea or product before they hear about pricing. It’s most important to capture their imagination and make them interested in future opportunities before you discuss cost; help them see the exciting value in what you have to offer. When you do discuss pricing, make sure they have an understanding of what others are paying. Avoid being overly-analytical or hyper-specific.

If you’re discussing pricing with an I, try saying or writing…

  • Let’s walk through the math together...
  • Here’s what some similar companies are paying...
  • I think we can come up with a creative solution...
  • The pricing model is pretty simple...

I Personality Types   Influencer, Motivator, Encourager, Harmonizer


  • Explain and write out the math for them
  • Share pricing verbally first, then write it down
  • Explain your ability to be flexible
  • Share what their peers are paying for similar products


  • Focus too much on the logic behind your pricing
  • Be hyper-rational at the expense of empathy
  • Let a pricing conversation drift into a broader discussion
  • Ask them to make a pricing decision without consulting others

Addressing S-types:

Warm, supportive S-types tend to seek connection and trust in their relationships, and this holds true in the buying process. It’s important to ask them questions about themselves, teach them about the product, and establish a more comfortable and secure environment before discussing pricing. 

When you address cost with S-types, focus on commitment and predictability. How can your company make sure their purchase will pay off in the long-run? Try discussing warranties and extended service agreements with them, but be sure to give them the flexibility to choose without unnecessary pressure.

If you’re discussing pricing with an S, try saying or writing…

  • How important is long-term predictability?
  • It’s important that we are both comfortable with this...
  • Let’s go through all the options together...
  • Are there others we should run this by?

S Personality Types   Counselor, Supporter, Planner, Stabilizer


  • Explain how they can achieve more certainty in the future
  • Walk through the individual components first, then the total cost
  • Provide options for a long-term commitment
  • Help them get approval from others for their purchase


  • Focus too much on competitors’ pricing
  • Anticipate a tough negotiation
  • Give them too many decisions to make
  • Bring up pricing before they are ready

Addressing C-types:

Analytical, reserved C-types will likely want to hear all of the concrete information you have to offer.

Focus on explaining the logic of the cost first, then offer clear breakdowns of the details and specific pricing. With C-types, it’s important to have significant, justifiable reasoning as to why your price is what it is, otherwise they will be more likely to push back.

If you’re discussing pricing with a C, try saying or writing…

  • Here are the additional terms...
  • Do you need any additional information?
  • Here’s the full pricing breakdown...
  • Here’s how the pricing formula works...

C Personality Types   Editor, Analyst, Skeptic, Questioner


  • Outline all the extra details like terms and conditions
  • Ask if they need any further information
  • Provide full item lists and breakdowns
  • Provide formulas, calculations, or visuals if possible


  • Throw out ballpark numbers
  • Leave out any details about cost
  • Make any errors or exaggerations
  • Get to the bottom line before explaining the logic

Personalize the discussion

Screen Shot 2019-08-07 at 10.54.11 AMUnderstanding the differences between personality types and adjusting your communication style to better reach people is the interpersonal way of the future. These personality differences are critical for discussions about pricing in order to move the purchase process forward and cement your sale.

However, if you use an approach that is wrong for the customer’s personality (even if it’s not wrong for your personality), it will likely put the entire deal in jeopardy. 

When you use Personality AI to tailor your communication and address costs in a way that accounts for the buyer’s core motivations and preferences, you can avoid mistakes and solidify strong long-term customer relationships.

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