Where Ideas, Experiences, and Lessons Learned Intersect

The Million Dollar Deal How-To

Posted on November 3, 2023 Updated on August 22, 2025

Eight years ago, one of my peers asked me to produce a two-hour sales training session for the combined global sales team. He suggested a session named “The Million Dollar Deal How-To,” which would show people how to go about finding and closing large deals. It was a good idea, so I went ahead and did it.

The presentation started with a list of my Top 20 deals to date and a brief description of each deal, the biggest of which had an $8.5M+ ARR and a 7-year total value of over $60M. I included an additional negotiation for a deal closed by another VP shortly before he left the company. It was a complex deal with a very large System Integrator worth $1M-$2M/year over five years.

The underlying assumption is that the seller performed proper qualification before this step. While this would be considered a “given” by many, I have seen far too many sellers focus on deals that would never happen. To be successful, you need to spend your limited time on the opportunities that you are most likely to win. The better your upfront qualification and ongoing validation, the more likely you will succeed.

My goals with this section were:

1. Demonstrate credibility.
2. Demonstrate how the concepts apply to both products and services.
3. Help the team see some commonalities between the deals.
4. Explain how a lack of attention to negotiations or the contract can ruin a great deal.

Next, I presented a comprehensive list of the key topics, providing examples of each, followed by a very active Q&A session. The session was well-received and resulted in an increase in deal size and sales volume over the next year.

The contracting part showed examples of how a simple missing or additional word (e.g., “Discounts calculated based on the Annual Cumulative purchase volume, where the word “annual” was a mistake that reset the value that would have cost us over $5M in revenue over the life of that agreement) and similar mistakes. As an aside, I was negotiating a deal a year ago, and someone in our Operations team made a small mistake (adding a period to the annual increase language) for a multi-year deal that would have cost us over $40K on the first renewal. The point of this section was that you only assume the deal is complete once it is correct and complete. 

Below are the Top 10 concepts from that training session that were common to all wins:

1. Relationships Matter – People buy from people they like and trust. Moreover, they tend to like and trust people with integrity who have the customer’s best interest at heart. Create Customers for Life.
   • Just because you can sell something to someone doesn’t mean you should – especially if it is not a good fit or won’t bring them value.
2. Understand the Needs and Quantify the Impact – Use their terms, phrasing, and figures to increase the relevance of their use case and seek their validation.
3. Understand Their Constraints – Document the various assumptions to determine how real or rigid they may be.
4. What Happens if They Do Nothing? – Ask questions like, “Why Now?” and “What is the impact of waiting a year or more?” The answers will help with qualification around genuine business needs. 
5. Understand their Timeline and Milestones – Working back from the targeted end date can create a sense of urgency and avoid unnecessary delays.
   • This is where Project Management can help you close the deal.
6. Be Creative – The key is to get the prospect to focus on the outcomes (the “Fundamental Objectives”) rather than the approach (the “Means Objectives”). Focusing on “what they need” versus “how it is done” can be more challenging. Consider other aspects of their business that could be impacted and proactively raise any potential concerns and your ideas to address them.
   • Remember, you are trying to solve their problems and not hide things that will become apparent later.
7. Don’t Discount Someone Based Solely on Title – Many mediocre salespeople dismiss everyone except the Economic Buyer. A better approach is to ask various stakeholders about their roles in the purchase process and how they make decisions. 
   • Alienating people you will need to develop a long-term relationship with doesn’t make sense.
8. Learn about the Alternatives and the Competition – How does our offering fare against the others? Why would they choose us over the competition?
   • It pays to be brutally honest when you are doing this.
9. Dream Big – You only know if you ask, and if it was too easy for the prospect to say ‘Yes,’ then you left money on the table.
   • It doesn’t mean you must extract every penny from the deal. Instead, consider what else you could have included to make things easier for the customer, accelerate the project, increase the probability of success, etc.
10. Create a Shared Vision of Success – Help people “see and feel” what success is like. That can be very compelling, especially if challengers come forward later in the process or some other issues arise.
    • The worst thing you can do is sell something that does not solve their problem. You make your Economic Buyer and Champions look bad, which helps ensure you will not do more business there anytime soon.

While there are still several other components of the overall approach, these provide the foundation. Selling is not easy, but it is rewarding to help your customers prosper and grow, and financially beneficial to exceed your quota by selling large deals. Good Hunting!