Project Management
The Million Dollar Deal How-To
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 had $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 had properly qualified the prospect 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:
- Demonstrate credibility.
- Demonstrate how the concepts apply to both products and services.
- Help the team see some commonalities between the deals.
- Explain how a lack of attention to negotiations or the contract can ruin a great deal.
Next, I presented a comprehensive list of key topics, provided examples of each, and led an active Q&A session. The session was well received and resulted in increased 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 alone. 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:
- 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.
- 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.
- Understand Their Constraints – Document the assumptions to determine how real or rigid they are.
- 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 qualify genuine business needs.
- Understand their Timeline and Milestones – Working back from the targeted end date can create urgency and avoid unnecessary delays.
- This is where Project Management can help you close the deal.
- 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.
- Don’t Discount Someone’s Value or Impact 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. That person may not be able to say ‘yes’ to the deal, but they easily create doubt and help kill momentum.
- 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.
- 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.
- 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!
Never Panic!
Panic is never a good problem-solving tool, regardless of your position or role. It is especially bad when you are in charge of people or brought in for your expertise. Panic leads to a myopic view of the problem, hindering creativity and fostering dread.
The point in my career when this became readily apparent was when I was working for a small software company. We had a new product (Warehouse Management System) and were launching our third deployment. This one was more complicated than the rest because it was for a pharmaceutical company. In addition to requirements like refrigeration and lot control, there was a mix of FDA-controlled items requiring various forms of auditing and security, and storage areas significantly smaller than previous installations (think small packages of medicine versus pallets of one product). It was a challenge, to be sure.
A critical component, “Location Search,” failed during this implementation. About 10-12 people were in the “war room” when my boss, the VP of Development, began to panic. He was extremely talented and normally did an excellent job, but his reaction negatively affected the others in the room. The mood quickly worsened.
I jumped in and took over because I didn’t want to be stuck there all weekend, and because I wanted this implementation to succeed. I asked my boss to go out and get a bunch of pizzas. Next, I organized a short meeting to review what we knew and what differed from our prior tests, and I asked for speculation about the root cause. The team came up with two potential causes and one potential workaround. Everyone was organized into three teams, and we began attacking each item independently and in parallel.
We identified the root cause, which led to an ideal fix a few days later and a workaround that allowed us to finish the user acceptance testing and go live the following day. A change in mindset fostered the collaboration and problem-solving needed to move forward.
But this isn’t just limited to groups. I was a consultant at a large insurance company on a team redesigning their Risk Management system. We were using new software and wanted to be sure that the proper environment variables were set during the Unix login process for this new system. I volunteered to create an external function executed as part of the login process. To keep the code clean, I added an “exit” at the end of the function. It worked well during testing, but once it was placed into production, the function immediately logged people out as they attempted to log into the system.
As you can imagine, I had a sinking feeling in my gut. How could I have missed this? This was a newer system deployed just for this risk management application, so no other privileged users were logged in at the time. Then, I remembered reading about a Unix “worm” that used FTP to infiltrate systems. The article stated that FTP bypassed the standard login process. This allowed me to FTP into the system and then delete the offending function. In less than 5 minutes, everything was back to normal.
A related lesson learned was to make key people aware of what happened, noting that the problem was resolved and there was no lasting damage. Hiding mistakes kills careers. Then, we created a “Lessons Learned” log, with this as the first entry, to foster the idea of sharing mistakes to avoid them in the future. Understanding that mistakes can happen to anyone is a good way to get people to plan better and keep them from panicking when problems occur.
Staying calm and focused on resolving the problem is a much better approach than worrying about blame and the implications of those actions. And most people appreciate the honesty.
As the novelist James Lane Allen stated, “Adversity does not build character; it reveals it.” Maintaining your composure and sense of calm (“equanimity”) makes chaos more manageable and helps develop resilience within the team. That is key to surviving in any high-pressure environment.
Connecting the Dots Faster
When I started consulting, an experienced consultant told me, “The best Consultants are experts at becoming Experts.” I started my consulting career with that goal in mind. After a few years realized that “Good consults are people who can learn enough quickly to ask intelligent questions and then connect the dots faster.” This is a great skill for anyone, regardless of the industry or business.
It’s impossible to be an expert at everything. I believe having great depth in a few areas (true expertise) and breadth of knowledge in many areas (enhancing context and insight) is important. Both types of knowledge alone are valuable, but combined, they add a dimension that allows a person to be far more effective and potentially much more valuable because it leads to the ability to pick up on the dependencies and nuances that others miss.
Just think – How much more effective is a salesperson who understands technology and project management concepts when working to demonstrate fit and create a sense of urgency? Or, an Attorney who understands the complexity of service offerings and delivery – enhancing their ability to construct agreements that are highly protective yet not overly complex or onerous. Or a programmer who thinks beyond the requirements and looks for ways to improve or simplify the process. Extra knowledge helps with the big picture understanding, and that often leads to providing more value by “thinking outside the box.” Additional knowledge and skills almost always help us become more effective, regardless of what we may be doing.
Increased knowledge and a desire to do amazing things create opportunities to make a huge and immediate impact. Sometimes it is because you are asking the questions that others may be thinking but simply cannot articulate in a clear manner. It helps you see the gaps and holes that others miss. And most importantly, it helps you “connect the dots” before others do (often many months before something obvious to you becomes obvious to others). A large consultancy once used the phrase “seeing around corners” to make this concept tangible.
So, if you buy into the concept that knowledge is good, the next question is usually, “What is the best way to learn?” People learn in different ways, so there really is no one single best way to learn. Understanding how you learn best will help you learn faster.
I’m a fan of reading. A good book may reinforce ideas you already know, introduce you to a few concepts or ideas that seem like they could help (giving you something to test), and often present many ideas that you know or feel just won’t work. Just don’t become one of those people who changes their beliefs and approach with every book they read (or what I refer to as “The book of the month club manager.“)
I’m also a fan of hands-on learning. The experience of doing something the first time is important. Keeping detailed notes (what works, what doesn’t make sense, what you did to figure it out, workarounds, etc.) enhances the value of that experience. It’s amazing what you can learn when you “get your hands dirty.”
What about formal education? I’ve never been a fan of the person who wants to get a degree in order to get a promotion. There are certainly some professions where education is critical to success (often through legitimacy as much as anything else). My advice to people is to work towards a specific degree because it is important as a personal goal and because it could possibly help you get a different or better job in the future. I will never criticize anyone for learning, going to school, or getting another certification or degree.
I believe the best way to get ahead is to learn the position, innovate, optimize, and deliver incredible results. You won’t “knock it out of the park” every time, but those “base hits” will help you score and ultimately win.
This is not to say that formal education is bad; I don’t believe that at all. I was working on my MBA at the same time I was expanding my consulting business from the US to the UK. I had a concentration in International Business, so I could apply many things I was learning right away. This bit of serendipity both enhanced my learning experience and helped me make better decisions that had real implications for my business. The funny thing was that I was working on that degree to raise the bar for my children, so this was just a bonus for me.
There are also other great ways to learn – ways that only require an investment of your time. There are many good free online courses. If you are interested in learning something or need to know more about it, there is almost always a place to find free or low-cost training. These are great investments in yourself and your future, and may help you learn to connect those dots faster.
Below are links to a few good free learning websites. Do yourself a favor and check them out. And, if you know of others, leave a comment and recommend them to others. Enjoy!
OpenCulture (directory with content from multiple sources)
Open Education Database (directory with content from multiple sources
The Power of Simplicity
“If you can’t explain it simply, you don’t understand it well enough.” – Albert Einstein
In the first part of my career, I didn’t care much for consultants. My experience was that they would come in, tell you what to do, and then leave victoriously while we were stuck trying to implement something that just wouldn’t work. They seemed to make everything seem so complex—often to justify their cost.
Then, I met an amazing consultant who shared something valuable with me. He explained what he believed differentiated a true consultant from a contractor (something I wrote about a decade later in a Tech Republic article). He then made me aware of the Einstein quote above. This was one of those pivotal moments in my career.
For many years, I have met many interesting people. Some seemed to try to intentionally obfuscate even the easiest things to make themselves seem brilliant. Others took such a circuitous route that you sometimes forgot what you were trying to understand and fix. And sometimes explanations were just so tangential that the main point was lost entirely. There are likely many reasons for these experiences – some intentional and many not. The real lesson learned is that it wasn’t just consultants who can be incomprehensible, and that clear, comprehensible communication is critical to effectiveness.
Just think about the power of a well-crafted “elevator pitch” when you meet someone new or the ability to quickly explain how your company differentiates itself from the competition (piquing their curiosity, making you the more interesting, or helping your company become the better/safer choice in your prospect’s mind).
Or being able to articulate your business strategy in a way that people understand (and can explain to others). That understanding can create interest, leading them enough to want to learn more and become part of making that happen.
The best consultants, as do the best employees/managers/executives/business owners, have this ability to explain something simply. While this is only one attribute of success (likability, powers of persuasion, integrity, knowledge, and skills are others), it is something that can be taught, developed, and consistently applied.
The power to “explain it simply” is the power to make a difference through better understanding, and that is what communication is all about!
Where Ideas, Experiences, and Lessons Learned Intersect 