lessons learned
Repeatable Sales Motions vs. Selling Success
Having a sales organization that consistently exceeds aggressive goals is the holy grail of growth-focused companies. A repeatable sales motion is often seen as the vehicle to make that happen. Unfortunately, few companies have translated salesmanship and the art of selling into the science of repeatable sales.
Often, one or two successful deals become the foundation for what is believed to be the repeatable sales motion. While there may be lookalike prospects you can focus on, that doesn’t mean there is real scale potential. This approach fails to address other independent variables, and often results in an approach that is neither repeatable nor scalable. Let’s take a more analytical look at what works and why, which leads to a better understanding of how to develop repeatability.
As the Roman philosopher Seneca is quoted as saying, “Luck is what happens when preparation meets opportunity.”
Preparation is more than understanding the prospect company, their competition and differences, the market they operate in, and what changes may be coming (technological, legislative, economic, etc.)—although that is often far more preparation than many Account Execs bring to a meeting. I’m always amazed at how unprepared many sellers are, and that is the quickest way to lose your prospect’s respect.
I’ve learned over the years that planning for the unexpected is planning for sustainable success. That can be as tough and nebulous as it sounds. You need to stay calm, unemotional, and in control while assessing the situation and adapting. Confidence definitely helps, as does logic. Composure is a key aspect of professionalism.
I like the Five Whys method of drilling into those statements or concerns to understand them. Sometimes it’s fluff, but sometimes it helps you close the deal faster because you uncovered something others missed. Other times, you qualify a prospect out quickly and move on to a better fit that develops into a closed-won deal.
Salesmanship includes:
- Being prepared
- Being likeable
- Relationship building starts with finding connections and common interests, then demonstrating your ability to help the prospect solve their problem (and at this stage they may be more focused on symptoms than root causes).
- Understanding the need. Why is this important to them? Document this, including their phrases and terminology, as that can have a huge impact on their acceptance of your proposed solution.
- Having value to add. This includes product knowledge, competitive knowledge, industry knowledge, and more. This allows you to have a perspective about their business that may not be 100% accurate, but will likely impress them and lead to deeper discussions about their needs and goals.
- Being respectful. This starts with respecting their time.
- Being focused on solving their problems. Without this, you won’t have a loyal and lasting customer base. To me, this is as much about reputation as it is about salesmanship.
- Learning from failures as much as success. Evolution is important.
These are all teachable/learnable skills. They also address the intangibles that fuel selling success.
So, which came first – the selling successes or the repeatable sales motions? To me, they go hand-in-hand. By developing a foundation of a high-performance sales team, pooling information gathered during sales discovery calls and other meetings, and focusing on unmet needs and associated messaging, it is possible to create and refine something that becomes repeatable. It takes more than one or two wins to prove there is a pattern.
Selling may not come naturally to a lot of people (it wasn’t for me), but it is a muscle that can be developed with hard work, practice, and a goal of improving each and every day. Your success may appear to be luck, but you will know better.
How ADHD Became My Professional Superpower
ADHD is often considered a disability, but in the complex and fast-paced world of business, it has become my greatest competitive advantage. This is the story of how this condition changed the way I work, view problems, solve them, and deliver value.
The Turning Point
My diagnosis came as a surprise through my oldest daughter. After a car accident left her struggling to focus, testing revealed her high IQ had been masking undiagnosed ADHD. As the psychiatrist detailed her symptoms, my wife looked at me and said, ‘That’s you.’ Six months later, the tests confirmed it.
The Superpowers vs. The Struggle
I began researching ADHD after my daughter’s diagnosis, and this new understanding explained so many things about my life. I realized I was much faster at taking a big-picture concept and distilling it into specific “work packages”—a project management term for sequences of related tasks tied to a single deliverable. At the same time, I was often much slower with routine tasks and activities. The diagnosis helped explain the best and worst aspects of this condition: hyperfocus and procrastination.
To many people, these contradictions did not make sense. To some, they were frustrating. But they all trace back to how the ADHD brain processes information.
I didn’t enjoy routine activities or the lack of focus they brought, so I developed systematic approaches that provided consistency, let me do more with less effort, and helped me complete those tasks faster. Later, I learned to automate those systems, and that was a game changer. These systems were accessible to anyone, delivered better results in less time, and made business more predictable and scalable.
However, as a consultant and later as a salesperson working with organizations ranging from small businesses to large companies, I realized that what corporate mindsets categorize as a limitation is actually a specialized toolkit. I do not see details sequentially; I tend to see entire systems simultaneously and then start considering potential problems and opportunities for improvement. That perspective led me to begin at the end, focusing on the “what” (goals and outcomes) instead of the “how” (often the status quo approach) when problem-solving.
While repeatable motions that have proven successful in business are highly desirable, not every business has achieved that goal. This is an area where creativity, understanding, relentless focus on a goal, and a continuous improvement mindset often lead to the desired goal.
How to Leverage ADHD in Your Career
- Audit Your Energy: Track when your hyperfocus naturally kicks in and what triggers it. Schedule your most complex, big-picture strategy sessions during those exact peak windows.
- Outsource the Routine: Automate, template, or delegate administrative tasks. This protects your brain from the mental fatigue caused by repetitive, linear work.
- Build Micro-Deadlines: Break large projects into immediate work packages. Artificial urgency helps trigger the dopamine required to power through procrastination.
Conclusion
For years, I couldn’t understand why I could map out massive, complex projects in minutes, yet struggle to finish a simple, routine task. My ADHD diagnosis and understanding of this condition helped me feel more normal. Additionally, it allowed me to better control and leverage it. Hopefully, this helps others understand themselves and expand their potential.
As Albert Einstein stated, “The definition of genius is taking the complex and making it simple.” This is something that the ADHD brain does well. Probably half of the business leaders that I have worked with exhibit many of the characteristics of this condition. I believe that knowing how to manage it can turn it into your superpower as well.
Playing to Win, versus Playing Not to Lose
Life is funny. There are always ways to justify nearly anything you want (or don’t want) to do. For example, “The timing is not right” (“We’re not ready,” “The market will be better soon,” “We need to save more,” “We need to staff up first,” etc.) Justifications often include things like “We had a bad experience once” or “We are a very conservative organization” – comments that tend to lean towards risk aversion or a lack of confidence.
I’ve seen this in my own business after a large investment failed to yield the desired results, when I was a regional sales and services leader at a “growth-oriented” software company, and as a consultant. The root cause always varies, but the net effect is that those companies play it safe.
Why is that a problem? It may not be. Being content may not be a bad thing. Sometimes the status quo is enough. Having a reliable schedule, manageable stress levels, sufficient funds, and doing something you like with people you like may be the goal. But not everyone is built that way.
Growth usually means stepping out of your comfort zone, taking on risk, recognizing the need to adapt to stay ahead of the curve, and being OK with uncertainty. It means bringing on people with different backgrounds, skill sets, and perspectives than yourself. It can be very hard – especially if you are used to being in control and having the answers.
For me, the solution was twofold.
- We had to accept failure as an inevitable outcome. I believe this is where a lot of people stop. If you view failure as negative, then everything that stems from it (loss of money, a hit to your ego, and other setbacks) becomes your focal point. Lesson Learned: When you view it as a learning and self-improvement opportunity (“cognitive reframing”), it just becomes part of the cost of getting better.
From your team’s perspective, if everyone is as focused on the journey as you are on the outcome, people tend to view challenges logically rather than emotionally (thereby controlling fear). Success truly is a mental game. - We developed a structured approach for future investments (read more about it here). We treated each new venture like a project. It was focused, analytical, and unemotional. With this approach, speculative investments became easier each time. It’s amazing how that distance also helps switch the focus from risk to reward.
This understanding led to a presentation I gave that helped relaunch a company, helped several clients critically assess the risks and rewards of their plans, and may help someone consider whether they are focused on winning or simply on not losing.
As Richard Branson wrote in his book, Screw It, Let’s Do It: Lessons in Life, “If you opt for a safe life, you will never know what it’s like to win.” So, are you ready to play to win?
Curiosity-Led Execution
Most organizations don’t struggle because they lack solutions—they struggle because they misdiagnose problems. A structured, curiosity-led approach accelerates alignment, reduces rework, and leads to solutions that actually stick.
My Starting Point
I was not a fan of consultants when I first started working with them. Most were arrogant, had limited focus, and viewed problems or goals in isolation. I later learned that the same could be said for salespeople, executives, and more. It had less to do with the role and more to do with how people presented themselves as experts.
Switching to consulting was a tough sell. When I finally accepted a position, I expected to learn proven methodologies from seasoned experts. The lessons I learned weren’t always what I had expected.
Many of the senior consultants I worked with had been highly successful early in their careers. But over time, that success calcified into rigid frameworks and default approaches. They weren’t completely wrong—but they weren’t adaptable or as effective as they could have been, either.
It reminded me of the old metaphor: “If the only tool you have is a hammer, everything looks like a nail.”
At one point, I seriously questioned whether consulting was the right fit for me.
Then I stepped back and looked at the best consultants I had worked with—the ones clients trusted and consistently delivered outcomes. I asked a simple question:
What do they do differently?
The answer wasn’t just expertise. It was curiosity, combined with the desire to deliver a positive experience and tangible outcomes.
From Depth to Insight
Early in my career, I went deep—sometimes excessively so.
I read dozens of manuals for a relational database system, cover to cover, just to understand how it worked. Then I spent years traveling, reviewing its source code at night, trying to understand why it worked the way it did. That understanding led to new ways of optimizing performance.
That effort paid off. I became recognized as an expert for that product, which opened the door to many challenging and exciting consulting engagements.
But it also revealed a limitation: Depth alone doesn’t scale.
What scaled was the mindset that I developed with it:
- Looking beyond surface-level symptoms.
- Viewing problems from a systemic perspective. Understanding how systems interact (not just how they function).
- Asking how and why decisions were made, not just what decisions were made.
I learned to read between the lines—technically and organizationally. To understand not just systems, but the people and processes behind them.
That context is powerful, but difficult to extract—especially quickly.
The Breakthrough: Structured Curiosity
What ultimately worked wasn’t just knowledge. It was a repeatable approach built on three elements:
- Establish credibility
Demonstrate enough expertise early to build confidence. - Lead with curiosity
Ask thoughtful, relevant questions that show genuine interest—not interrogation. - Close the loop
Articulate your understanding back to stakeholders to confirm, refine, or challenge it.
This creates a feedback loop:
Curiosity → Insight → Validation → Alignment
That loop is where trust—and progress—happens.
A Practical Tactic: The “Columbo Technique”
One of the most effective tools I’ve used is commonly called the Columbo Technique.
The idea is simple: Lower defenses by creating psychological safety—and a sense of control.
Instead of pushing for answers, you:
- Ask informed questions
- Make partial observations
- Then, intentionally leave a gap
Something like:
“I might be missing something, but I’m not fully connecting how X impacts Y…”
This does two things:
- Signals humility (reducing resistance)
- Invites correction (which reveals deeper truth)
People tend to open up—not because they’re forced to, but because they want to contribute. They feel safe because you are focused on understanding the situation and solving the problem, and not pointing fingers or assigning blame.
And once that happens, you get access to what actually matters: the “why” behind the “what.”
Applying This in the Real World
This approach works across consulting, sales, and leadership—but only if you apply it deliberately.
Here’s how to operationalize it:
1. Start Broad Before Going Deep
Don’t jump to solutions. Map the landscape first:
- Stakeholders
- Systems
- Constraints
- History
2. Use Their Language
Mirror terminology and examples. It builds alignment faster than forcing your own framework.
3. Validate Early and Often
Don’t wait until the end to present conclusions. Share evolving understanding:
- “Here’s what I think I’m seeing…”
- “Does this match your experience?”
- “Can you help me identify reasons why this might not work?”
4. Balance Confidence with Curiosity
Too much confidence shuts people down.
Too much curiosity erodes credibility.
The balance is where influence lives.
5. Optimize for Adoption, Not Perfection
The best solution is the one that gets implemented and sustained—not the one that looks best on paper.
A great example of this is at a large insurance company, where I led a successful 18-month redesign and implementation of a common Risk Management System used across three distinct businesses.
Before I came, they spent two years and several million dollars with a Big 5 Consulting company. The output was several 3” binders filled with specifications, definitions, and design documents. It was amazing, but wasn’t implementable. I have seen that far too often on consulting engagements.
A section in the middle of this post describes what happened with that project.
Make It Repeatable with the CLEAR Framework
This is a simple, reusable model that can help anyone new to a company or role.
The C.L.E.A.R. Framework
C — Credibility
- Establish baseline trust quickly.
- Demonstrate you “speak their language.”
L — Learn
- Map systems, stakeholders, constraints, and history.
- Ask high-quality, layered questions.
E — Expose
- Surface gaps, contradictions, hidden dependencies.
- Use techniques like the “Columbo Method.”
A — Align
- Play back understanding.
- Build shared clarity before prescribing.
R — Recommend
- Deliver solutions optimized for adoption and results, not elegance alone.
Why This Matters
Knowledge explains. Curiosity transforms. When you lead with curiosity, you move faster—not slower.
You avoid rework.
You uncover hidden constraints early.
You gain stakeholder alignment before decisions are locked in.
And occasionally, you can help solve problems that have existed for years—in a matter of weeks—because you’re solving the right problem.
If this sounds interesting and you would like to discuss it further or seek out assistance, contact me here.
What is Customer Success?
In most companies, it is a department or a team. I would argue that it should be foundational in a company’s culture. Companies need to focus on providing products and services that solve critical business problems for their clientele. By doing so, they create a predictable revenue stream and install base that supports future growth.
In a quarterly executive meeting a decade or so ago, the head of the Support organization stated this team was the most important. The head of Engineering then stated that her team was the most important. I chimed in and stated, “Without Sales, nothing happens, but ultimately, if all teams are not focused on the same objective, like a tripod, then all teams will ultimately fail.” Our CEO agreed, and that was the end of the discussion.
You could also argue that Marketing and Services should be included, and I would agree, since it goes back to all teams being focused on a singular, overarching goal.
In a previous post about creating Customers for Life, I wrote about a tactical implementation to address customer churn, which is the byproduct of failure in one or more areas. This was a wake-up call for me, as we were very focused on the success of our largest accounts and most productive channel partners – totaling 70% of our revenue, but we took the other “less valuable” accounts for granted. The lesson learned was that 30% of $62M is a large number, and by applying the same techniques to those accounts, we increased organic growth while minimizing churn.
Why Customer Success Teams Struggle
- Lack of Ownership: They don’t own the accounts and often lack the motivation and accountability for each customer’s health and success.
- Stay Reactive: They are reactive rather than proactive advocates for customers.
- Lack of Resources: They are spread too thin and lack the capacity to actively engage with all but a few customers.
- Enter Too Late: They are not introduced early in the sales process, which is a great way to demonstrate commitment to the prospect’s success if they select you as a vendor.
- Stay Low in the Org Chart: They do not develop relationships beyond a small operational team, limiting executive visibility and expansion potential.
- Ad Hoc in Nature: They lack formal processes, including detailed documentation, that help ensure consistency and continuity over time.
How to Position Your Team for the Win
- SWOT: Review your strengths and weaknesses. Why do companies buy from you? (or, what are you really selling?) What are you known for? What do people like and appreciate? Where do you fall short? (opportunities for others) Accentuate the positive and focus on improvements where needed.
- We often received customer feedback that when they called our support team, their problem was solved on the initial call. With other vendors, it often took 2-3 people to reach someone knowledgeable who could help. We promoted this when selling and reinforced the importance of maintaining this positive image to our internal teams.
- We also received feedback that some of our technical features were lagging behind the competition, so my team and I helped identify the most critical features, then worked with Engineering to prioritize them and focus on bringing in new customers who needed them. It was a win-win.
- Be Proactive: It is often possible to anticipate problems or make improvements based on your understanding of the customer and their history. Being part of the solution means that you don’t wait for the next problem to engage.
- When I had my consulting company, we provided managed services for several large companies. We had proprietary monitoring tools that reported conditions that often led to outages if left unchecked. We addressed the issue and informed the customer once it was resolved. Our monthly summary report listed the likely outages avoided, the average duration of similar outages, and the cost avoided (based on the hourly cost of downtime). Key people saw our value at least monthly, so when it came time to renew our service, the process was fast and painless.
- Become the Internal Liaison: The customer success team should serve as the main conduit for information. Introduce your Services or Engineering teams to the customer early. This doesn’t just solve problems; it uncovers new opportunities to provide value (and sell additional services) that position the customer for even greater success. Engagement and a sense of partnership go a long way.
- I will often introduce the Services team when problems or needs arise. Their expertise and insights can be very valuable, often leading to services that position the customer for even greater success.
- Go Above and Beyond: People remember that. Teams begin to rely on you. And Executives begin to see your company and products as critical to their success. This creates long-term value for your company.
- Focus on the Future: Ask your customers, “How can we help with your upcoming initiatives and projects?” This is a great way to learn what they will be working on, to show your interest in their success, and to identify how your company and products can help them achieve it.
These are things that have been very successful for me when I was leading two large global regions, when I was a top Account Executive at a company with a small customer success team, and as a Consultant. I set expectations, led by example, and they began doing much more of what I expected from the customer success team. We started seeing improvements in the first 30 days.
While leadership doesn’t have to come from designated leaders, cultural changes usually require the commitment, involvement, and support of the organization’s top executives. Everyone can make a positive impact on a company’s direction and success.
When the customer wins and views you as a key partner, you don’t have to worry about churn.
Where Ideas, Experiences, and Lessons Learned Intersect 