Selling
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.”
Sales Success for the Individual Contributor
Let’s start with two of my favorite personal quotes:
“Luck is what happens when Preparation meets Opportunity.” – Seneca, Roman Philosopher.
“Become the person who would attract the results you seek.” – Jim Cathcart, Author of “Relationship Selling”
Why are those quotes important? Because they point out that you are responsible for your own success.
Great companies with great products or services and great management teams make it much easier to be successful, but anyone who is prepared, curious, focused, motivated, and has a system they follow can succeed anywhere.
My experience has shown the following to be true:
- You are unlikely to succeed without preparation and understanding of your prospects, their customers, and their competition. This understanding provides the foundation for asking relevant questions to understand the real need and effectively qualify a deal in or out.
- Most sales occur because a Product or Service solves real and immediate business problems or ties into strategic business initiatives.
- Your early goals should be around getting the meeting, having real discussions, understanding problems from your prospect’s perspective (including the terminology they use to describe those problems), and helping them describe what success “looks like to them” and why that is important (logically and emotionally). At this stage, you are learning and positioning, not selling.
- Deal qualification is an essential skill that enables you to focus your time and efforts where you are most likely to succeed. The faster you can “qualify out” a prospect that is not a good fit, the better it is for you and that prospect. Eternal optimism is not a plan for filling your pipeline.
- If you have a supporting team, ensure that everyone understands the situation, their role and contribution to success, and what you want them to focus on. Never assume that things will just fall into place on their own.
- Have a repeatable process to track activities, measure progress, and identify the best next steps. Remember, “To measure is to know.” (Lord Kelvin)
- The sale is not over until your new Customer is happy. Become their internal advocate within your organization, and you will be rewarded with the customer’s trust, loyalty, and repeat business.
Ideally, your Sales Leadership Team has defined a Sales Strategy and created a couple of repeatable Sales Plays and compelling supporting materials such as Success Stories; Case Studies; ROI and TCO charts; brief but targeted Demos; and realistic Product Comparison information for internal use. These become the foundation for repeatable and scalable success.
But, if that is missing, collaborate with your peers, seek guidance from your leadership, and get creative. Remember, you are ultimately responsible for your success, so don’t allow things to become excuses or a crutch. In the words of the Buddha, “There are three solutions to every problem: Accept it, Change it, or Leave it.”
To help ensure success, you will need to follow a Sales Methodology. Here is a link to a good high-level overview from Spotio.com. I’ve used several and there are pros and cons to each. None of them effectively addresses the successful progression from:
- Initiation, Understanding, and Qualification.
- Defining a compelling Solution and successfully positioning it against the competition.
- Closing the Sale is an area in which many salespeople fall short.
The sales methodology that I personally believe is one of the easiest to use and most effective is MEDDIC. It is a Deal Qualification process, which is more encompassing than a simple Lead Qualification approach. The biggest blind spot is that it fails to address these four key areas:
- Influencers within a buyer’s organization. Knowing who these people are and their biases will allow you to direct various resources towards each and ideally provide a multi-threaded approach for each deal.
- Incumbents and the sentiment towards those vendors and their products. This is key to not wasting time on an opportunity you would unlikely win.
- Related/Adjacent needs. Being able to tie success to multiple areas provides leverage and increases the value of your solution.
- Timeline/Urgency. This allows you to work backward from milestone dates for efforts like typical lead times for Legal and Purchasing, Integration Testing, QA/QC, Training and Documentation, etc.
Being prepared, creating a common vision of success based on the outcome rather than the approach, being responsive, and developing relationships and trust based on knowledge and a desire to help are easy ways to differentiate yourself from many lesser salespeople. Invest in your skills, set aggressive goals, and always hold yourself accountable for success.
Do this and you will become part of the 20% of any sales team that ‘moves the dial.’
Are you Thinking About Starting a Business?
The last post on Starting a Business was popular, so I thought I would share a key lesson learned and then provide links to previous posts that will provide insights as you launch your own business. If you have any questions, just post them as comments; I would happily reply.
The COVID-19 pandemic has created a great deal of uncertainty and opportunity. For many, now is the ideal time to explore their dream of starting a business and jumping into entrepreneurship. That can be exciting, fun, stressful, financially rewarding, and financially challenging, all within the same short period of time.

Being prepared for that roller coaster ride and having the ability and strength to continue pushing forward is important. Something to understand is that “Things don’t happen to you. They are the Direct Result of your own Actions and Inactions.” That may sound harsh, but here is a prime example:
When I was closing my consulting business down, I trusted my Accountant and Payroll company to handle all of the required Federal, Wisconsin, Ohio, and Colorado filings – something they stated they would handle, and I accepted at face value. Both companies had done a great job before, so why would I expect any less this time?
About nine months later, I started receiving letters from Ohio and Colorado about filings due, so I forwarded them to the Accountant and Payroll company. I thought this was “old business” and was being handled, plus I had moved on. It was probably just a timing error, something easy to explain away.
Skipping forward nearly three years, I had been threatened by the IRS and the Revenue Departments from both Ohio and Colorado. I started with a combined total of nearly $500K in assessments. Slowly that dropped to $50K, and then to $10K. I spent countless hours on the phone and writing letters explaining the misunderstanding. It wasn’t until I finally found a helpful person in each department willing to listen and tell me specifically what needed to be done to resolve that situation. My final cost was around $1,000. I was relieved that this fiasco was finally over.
I blamed both the Accountant and Payroll Service for these problems for the longest time. Ultimately I realized that it was my business and, therefore, my responsibility to understand the shutdown process – regardless of who did the work. I would have saved hundreds of hours of my time and several hundred dollars by gaining that understanding initially.
I was not a victim of anything – this situation directly resulted from my own inaction. It did not seem very important at the time, but my understanding of the situation and its importance was incorrect, and I paid the price. Lesson learned. It was my business, so it was still my responsibility to the very end.
Below are the other links. You don’t have to read them all at once, but it would be worth bookmarking them and reading one per day. Every new perspective, idea, and lesson learned could be the thing that helps you achieve your goal a day, week, or month sooner than expected. Every day and every dollar matters, so make the most of both!
- Comments on and a link to an on Curt Culver about Entrepreneurship.
- Comments on and a link to an HBR article about Start-ups and Entrepreneurship.
- Innovation, Intelligent Failure, and Failing Productively.
- Acting Like an Owner – Good Preparation for Becoming an Owner.
- Profitability Through Operational Efficiency.
- What Are You Really Selling?
- Continuous Improvement and a Growth Mindset.
- The Value Created by a Strong Team.


