Career
Two Truths of Enterprise Sales
I have been selling products and services to large enterprise organizations for most of my career. I like to tell people, “Everyone is in sales,” because one way or another, they are.
Early in my career, I was a Systems Analyst for a Marketing company. I created what I’ve been told was the first custom coupon system for Subaru, as well as several systems for Mitsubishi Motors and Mitsubishi Electric. We would devise several ideas to pitch to the customer and then have follow-up meetings to flesh out the idea and help sell an extensive, multi-faceted program. It was a great learning experience in understanding what mattered and how to effectively upsell deals.
Standard sales advice is to sell to a known problem or a project. The thinking behind finding projects is that a tactical or strategic need has already been identified, with executive support and funding to address it. Most companies have some degree of dysfunction (which is why Patrick Lencioni’s books are so popular) that tends to affect projects negatively.
Focusing on problems is the way to go, but a business rarely comes to you to disclose those problems and their impact. A Consultative Selling approach is helpful in this situation. The upfront preparation can be time-consuming, but the results are often bigger deals that close in less time.
The process I use involves understanding the business, its customers, and competition, as well as potential changes to that business or industry. I will search for clues that indicate potential problems (from financial reports and filings to product-specific forum posts). I will then hypothesize about a few potential problems and reach out to the highest-level individuals in the organization likely to be responsible for these issues.
When you do speak with someone, you need to demonstrate your understanding and potential value add to learn more and begin gaining their trust while listening for validation or other information to refine your hypothesis. People buy from people they like and trust, and this approach becomes the foundation. From here, you can guide the process and expand your reach to other areas and layers of the organization. As a seller, your focus is on proposing real solutions that are mutually beneficial and have a high probability of success.
So, back to the two truths –
- Companies and teams are often biased toward the status quo and the familiar. Problems are rarely solved using the same people, products, and processes that got them into this position in the first place. Your focus as a seller needs to be on outcomes. Help them visualize what success looks like and how it feels. Overcome negative emotions of fear using positive emotions and envisioning a better future.
- Change can be expensive at first. It is an investment in the future that should yield both short-term benefits and long-term savings. Your focus as a seller should be on delivering value.
This approach and understanding can lead to new customer acquisition and ongoing account growth. You are continually demonstrating your value and commitment to your customers’ success, and that pays off.
Here’s a bonus third truth. If you cannot quickly gain consensus on the root cause problem(s) or traction with your proposed solution, qualifying out is often the best next step. Nurturing the prospect may lead to a future deal, but leveraging that 3-6 months on another prospect will likely result in more deals closed. Qualify out quickly and move on – that is better for everyone involved.
Remember, hope is not a strategy.
Success is a Mental Game
This assertion is as true in business as in sports, individually and in teams. So, let’s break it down.

When I watch my local football team, I occasionally see a shift in facial expressions from excitement to frustration – often right before the end of the first half. Sometimes, they recover during halftime and come out renewed and ready to win, but the “gloom and doom” expressions usually translate into suboptimal performance and mistakes. It is frustrating because you know they have the talent to win.
The same thing happens in business – especially in Sales. Sometimes it occurs in the middle of a sales cycle, similar to the example above. Unfortunately, too many people allow a few data points to determine their future trajectory. Why is that?
Whether you own a company or manage a group of people, good leaders aim to optimize their workforce by balancing factors that result in happy and loyal employees doing their best for themselves, their customers, and their company. Many motivational theories exist, such as Expectancy Theory, Reinforcement Theory, the Role of Instrumentality, Intrinsic vs. Extrinsic Motivation, and more. Since one size rarely fits all, the challenge becomes an effort of reward-focused personalization, which can be a lot of work.
People will often win or lose before they even start. Their negativity, self-doubt, and anticipation of failure become a self-fulfilling prophecy. This post focuses on self-motivation, attitude, mindset, and creating the habits that lead to better success.
Below are four simple questions that someone should ask themselves when they question their ability to succeed in a position, company, or industry. There are always many ways to point the finger of blame elsewhere, but the first step should be to look in the mirror.
- Do you believe that you can win where you are today? If not, why are you still there? Customers and prospects can sense insincerity, so if you don’t believe in yourself, you shouldn’t expect them to believe in you. Maybe the company is terrible, and everyone is failing. If that is true, then it is probably time to look elsewhere.
- What have you learned from past successes and failures, and how have you adapted based on those lessons learned?
- What are some early indicators of success or failure that you have identified? Are you adapting to the situation if you run into those indicators now? It could be that the best approach is to cut your losses on this attempt and move to the next sooner rather than later (i.e., qualify out quickly).
- What are you doing to improve your skills? It is funny how small, continuous improvement efforts lead to a greater sense of confidence. Greater confidence often translates to increased success.
I have found that consistently doing the right things is the best way to maximize my success. Start developing habits and routines that have led to winning in the past, but don’t expect them to work forever. Everything changes, and you should change, too. Look for things that are working for others, try them out, and if they work, incorporate them into your routines.
Success truly is a mental game, and everyone can win. The person who continues to win over time is the person who does not get stuck in time. Be curious, get excited, and adapt. And once you get there, start helping others. Having mentors is nice, but it is also great to become one.
As the saying goes, The rising tide lifts all boats. Winning can be a team sport, but it begins with individual contributors having winning attitudes. Unfortunately, the same can be said for losing, so decide now what you want and go forward with energy and confidence.
Never Panic!
Panic is not 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.
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. 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 did not want to be stuck there all weekend and mostly 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 was different from our prior tests and asked for speculation about the root cause of this problem. 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. Trying to maintain clean code, I had 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 had been resolved and that 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.”
Understanding the Real Issue using Root Cause Analysis
Too often people, including Consultants, spend time trying to solve the wrong problem due to having incomplete or incorrect information. Once, I was investigating a series of performance problems and unplanned outages that were assumed to be two separate problems. As I gathered information, several people provided anecdotal stories of anomalous behaviors in various systems, speculation about the “real problem,” and discussions about “chasing ghosts” during previous attempts to resolve the problem.

I remember stating that I was there to solve a real problem having a serious negative impact on production and that it was not my intent to chase ghosts or do anything else that would unnecessarily waste time. Next, I outlined the approach I would use to make a Root Cause determination and that we would reconvene to discuss the real problem and potential solutions. A few people scoffed and felt this was a waste of time and money.
The process followed was simple, structured, and logical. It took everything that was known to be true and mapped it out. I looked for patterns, commonalities, and intersections of systems and events. Within two days, my team and I had identified a complex root cause involving multiple components, which we demonstrated would reliably reproduce the symptoms that our client was experiencing. From there, we worked with their teams to make minor network changes, system configuration changes, and several small application changes.
By the end of the second week, they were no longer experiencing major slowdowns or unplanned outages. Each outage cost this company tens of thousands of dollars in lost sales due to the time-sensitive nature of their product. Within one week, they had recovered the cost of hiring me and my team. What stuck with us was how many really smart people “believed in ghosts” and failed to focus on the information they already had.
A few years later, we created a white paper to potentially help others needing a simple structured approach. Below is a link to that white paper written by one of the top people on my team. We received very positive feedback then, so it seemed that this could still be useful today. Please take a look and let me know what you think.
Using Themes for Enhanced Problem Solving
Thematic Analysis is a powerful qualitative approach used by many consultants. It involves identifying patterns and themes to better understand how and why something happened, which provides the context for other quantitative analyses. It can also be utilized when developing strategies and tactics due to its “cause and effect” nature.
Typical analysis tends to be event-based. Something happened that was unexpected. Some type of triggering or compelling event is sought to either stop something from happening or to make something happen. With enough of the right data, you may be able to identify patterns, which can help predict what will happen next based on past events. This data-based understanding may be simplistic or incomplete, but often it is sufficient.

But people are creatures of habit. If you can identify and understand those habits and place them within the context of a specific environment that includes interactions with others, you may be able to identify patterns within the patterns. Those themes can be much better indicators of what may or may not happen than the data itself. They become better predictors of things to come and can help identify more effective strategies and tactics to achieve your goals.
This approach requires that a person view an event (desired or historical) from various perspectives to help understand:
- Things that are accidental but predictable because of human nature.
- Things that are predictable based on other events and interactions.
- Things that are the logical consequence of a series of events and outcomes.
Aside from the practical implications of this approach, I find it fascinating relative to AI and Predictive Analysis.
For example, you can monitor data and activities proactively by understanding the recurring themes and triggers. That is actionable intelligence that can be automated and incorporated into a larger system. Machine Learning and Deep Learning can analyze tremendous volumes of data from various sources in real-time.
Combine that with Semantic Analysis, which is challenging due to the complexity of taxonomies and ontologies. Now, that system more accurately understands what is happening to make accurate predictions. Add in spatial and temporal data such as IoT, metadata from photographs, etc., and you should be able to view something as though you were very high up – providing the ability to “see” what is on the path ahead. It is obviously not that simple, but it is exciting.
From a practical perspective, keeping these thoughts in mind will help you see details others have missed. That makes for better analysis, better strategies, and better execution.
Who wouldn’t want that?

