lessons learned
Curiosity-Led Execution (5-minute read)
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 but was more evident when 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 learned were not always what I had anticipated.
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 that delivers tangible positive 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, while traveling, going through its source code, trying to understand why it worked the way it did.
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 applied 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
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. Failing to do that will ultimately lead to the death of products and ultimately corporate decline.
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 with me, 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 wakeup 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 do not own the accounts and often lack the motivation and accountability for the health and success of each customer.
- 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 feedback from customers that when they called our support team, their problem was often solved on the initial call. With other vendors, it often required going through 2-3 people to get to 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 would report conditions that often led to outages if unchecked. We would address the issue and inform 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. Every person has the potential to 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.
Lessons Learned from GTM Consulting
For the past two years, I have performed part-time, contract go-to-market consulting. My wife had a surgery that had gone wrong 18 months ago, so I needed something that would allow me to take care of her, stay sharp, earn money, and help companies grow.
Most of the work was with small to midsize companies, but the problems and needs mirrored what I have encountered at larger companies. The main difference is that large companies tend to look to software to address problems. In contrast, smaller companies lack the budget for what they view as an unproven solution that increases complexity.
Here are my Top 5 findings:
- GTM plans are often developed at the highest levels, often in isolation, without market testing and validation.
- Sales teams are pitted against one another, rather than working together to help everyone achieve more (i.e., “A rising tide lifts all boats.”)
- Sales teams are focused on selling features rather than solving business problems.
- CRMs are not consistently used and often reflect idealized fiction rather than reality.
- Sales management and teams are not leveraging AI to help focus their efforts.
Here are the related Lessons Learned:
- Identifying common business problems and describing how your product or service solves them should be the foundation of the plan. Perform market analysis. How do companies describe those problems? Their terminology, often found in job ads, can help create effective messaging that resonates. Work to become the natural fit for what your prospects are seeking.
- Individual contributors get paid to win, but sales management needs to create incentives for collaborative efforts that lead to wins.
- For one company, I convinced them to implement a 2% SPIV (like a SPIFF, but team-focused) for every team member who actively contributed to team improvement. SPIV payments were quarterly, and there was a running total so the team could see the fund growth. Initial indications of a positive impact are good.
- Another benefit of collaboration is that it helps teams focus on approaches that work due to ongoing testing and refinement. Collaboration also helps teams focus on a more accurate ICP (ideal customer profile). Sales management can then feed their findings back to Marketing to improve and tailor their efforts.
- Selling is a byproduct of problem-solving. You can’t solve problems if you don’t know what they are. Every interaction with a prospect should focus on gathering information, building trust and relationships, and leveraging prior interactions to demonstrate that your solution will solve their problem and ease their pain.
- CRMs often either lack information or are full of wishful thinking. They focus on activities, and not progress and next steps. Using MEDDIC/MEDPICC as a foundation for reporting is a much better start. Sales managers need to independently validate the information to ensure their teams are being upfront and honest. Trust, coaching, and collaboration work together for the win.
- AI is not a panacea, but it is very effective for research, market validation, prospecting, and meeting preparation. Going in prepared builds respect and credibility, saves time, and lets you quickly qualify prospects in or out. There may be a nurturing program for some of the prospects qualified out for immediate deals, but your time is valuable, and you will go hungry chasing deals you can’t close.
So, what are your thoughts? Have you seen some of these problems yourself? How did you handle them? Let me know in the comments below.
And if you are looking for a Consultant to help your business grow or someone who can add immediate value to your team, then contact me.
Beyond the Hunt: Fueling Sustainable Enterprise Sales Growth
The software start-up world is obsessed with “Hunters” – salespeople laser-focused on landing new customers. Job boards are overflowing with companies in “growth phases,” desperate for new logos. Understandably, the revenue from each new customer can mean a 10-20x multiple in company valuation in the VC-fueled race toward an exit. But what happens after the deal closes? Is that frenzied growth sustainable?
The Long Game: Profitability and Sustainability
My experience leading a large business unit and running my own company has taught me that sustainable growth requires more than just a flood of new logos. Here’s why:
- Cash flow is King: Lines of credit can vanish overnight (remember Silicon Valley Bank?). Relying solely on external funding is a risky approach.
- Not All New Business is Good Business: Unprofitable accounts, high-churn risks, and customers with limited growth potential can drain your resources faster than you can acquire them. Efficiency matters for scalability.
- Profits Drive Long-Term Growth: Organic, profit-fueled growth, especially when driven by innovation, creates a much more resilient and valuable business.
The Power of the Hybrid Sales Model
To achieve sustainable growth, you either need an extensive and fully integrated organization that seamlessly transitions from the sale to implementation (not many companies are able to accomplish this), or a hybrid sales team that excels at both hunting (50-70%) and farming (30-50%). Landing a new customer is hard work, but retaining and growing them is just as challenging and crucial. Customer acquisition costs are often too high to justify losing a customer only a year or two after the initial win. Treating new customers like assets (instead of commodities) is essential to long-term success.
Mastering Strategic Accounts: Turnarounds and Growth
Large, strategic accounts—Tier 1 companies with strong brand recognition and significant revenue potential—present unique challenges. In my experience, these accounts often fall into two categories: those I initially closed and then grew (ideal, as you have already laid the foundation for success), and those I inherited in a neglected state and had to turn around.
Turnarounds require a unique skill set. They demand as much time and sometimes even more effort than landing a new logo, blending aspects of both hunting and farming. It takes commitment, skill, patience, and effort to understand an organization and find new ways to deliver value. Relationships and trust take time to develop, and in this situation they are in question (or worse).
Case Study: From Churn Risk to Multi-Million Dollar Expansion
Take, for example, a large Financial Services company I inherited when their Strategic Account Manager left. The account had been neglected for two years and was riddled with problems. We lacked executive relationships and higher-level visibility within the organization. They were evaluating competitors, and we knew nothing about it! Even though they were an existing customer, we were the underdog.
I organized a day-long on-site meeting to understand their pain points. We identified immediate issues, shared our vision for the future, began building trust, and demonstrated our commitment to their success. Following this, we spent a few hours getting to know the team over dinner. It was an eye-opener for me, with them providing more information about their needs and how best to approach them.
The result? Within three months, I closed a $500K expansion deal, followed by a $500K consulting engagement and then a $3.25M two-year cloud expansion and upgrade prepay deal. My team and I rebuilt the relationship, solved critical problems (even going beyond our product scope), and provided a clear path forward with our AI-powered platform. I became a trusted advisor who was valued by their executive team. It was a true win-win.
The Bottom Line: Building a Sustainable Sales Engine
Install base growth and customer retention is critical for long-term success, especially with larger customers. The approach has to be multi-dimensional. It is a team effort, and the Account Executive is the quarterback. Relationship management, customer success teams, support, and services all play a role. Effective communication is bi-directional, where the customer has insight into what is coming down the road and input into the direction of products they rely on. This becomes a true partnership that adds significant value to both organizations.
Does this hybrid approach apply to every company? If you’re IBM or Oracle, your offerings are broad and deep, and your customers are largely locked-in. “Land and expand” is part of their DNA. And if you’re selling end-of-life products, your focus might shift towards maximizing the “long tail” through customer success and services to minimize costs and maximize profitability.
However, for most growth-stage Cloud and SaaS companies, the hybrid sales model is an essential part of their success.
Call to Action:
- Evaluate your sales team structure and compensation plans. Do they incentivize both new customer acquisition and ongoing account growth?
- Invest in training and development for your sales team. Equip them with the skills needed to excel at both hunting and farming. It can be a difficult transition, but is worth it in the long run.
- Need help building a high-performing hybrid sales team or turning around strategic accounts? Let’s connect!
Sales Discussions that Work
Selling is challenging work, and often, “we” (sales and marketing teams) make it even more challenging than it has to be. How many times have you seen a selling script, elevator pitch, or initial presentation that is long, boring, and undifferentiated? People have a short attention span, and nobody wants to interact with someone who does not listen to them or is pushy.
Your initial discussion is crucial to your success. Instead of going over a list of features, reading a slide deck, and telling why you and your product are so great, let’s try something else.
1. Understand why people buy. Any change has the potential to be difficult, risky, and painful. So, the pain they are facing has to be even greater, or they won’t bother changing. Your main job early on is to listen and try to understand their concerns. You may have a perfect solution, but if it doesn’t solve their pain, it holds little value to your prospect. This initial meeting is all about them.
2. At the start of the meeting, ask, “What would make this time well spent for you? What would you like to walk away from this meeting with?” Get them thinking about their problems and the value you may be able to provide, even if they don’t fully articulate them to you.
3. Ask questions and follow-up questions. People don’t lead with their significant issues, and someone unwilling to divulge anything likely isn’t a buyer. The more the prospect talks, the more you learn. So many sellers do not understand this simple concept. They want to dazzle you with features and demos – even if those things are not what the prospect needs.
4. Once you think that you have identified a pain, qualify and quantify it. For example, “You mentioned that your product release cycles are too long and complex. What is the business impact of that, and what would the impact be if you could reduce that time and effort by 50%?” Write that down, in their own words, because it could be vital later. If you manage to identify several pain points, review them and ask the prospect to identify the top three issues from the list, and ask why those three?
5. If you are giving a presentation, pull up the most relevant slide (customer problem/benefit slides work well here) and ask if this sounds similar to the problem they are facing. It can be a good starting point for getting the discussion moving in the right direction.
6. Don’t worry if you are not able to cover everything you intended, as long as the meeting is productive. I’ve also seen salespeople cut someone off and move on to a new slide rather than discussing something of substance. I was actually told once by a sales leader that five minutes of discussion is all that is required in an initial 30-minute meeting, because our goal is to pique their interest. That just doesn’t work.
7. Next steps. Keep in mind that your time is valuable, and qualifying out a prospect who is not a good fit is essential – it helps you avoid false hopes and lets you focus on people who might genuinely need your help. There are many ways the next meeting could go, but it’s best to ask the prospect. Would they like to expand the audience? Is there a specific issue they would like to address? Would they like a product demo or a technical discussion? Is something like a non-disclosure agreement (NDA) keeping them from opening up? Lack of engagement on their part is a huge clue. Be direct and ask the tough questions now to avoid wasting valuable time and effort later.
Here is a mini success story. In 2010, my team and I began selling the first commercial vector high-performance analytics database. There were several products already out that claimed to be 70x-100x faster than other products. Our pitch was supposed to be that we were 70 times faster than other products. That was self-limiting from the start and likely prevented people from contacting us.
After two months of minimal success (I closed a deal with a small hedge fund, which was the only sale in all regions), we started a weekly webinar called “Why Fast Matters.” The focus was on positive business outcomes rather than specific technology and features (“speeds and feeds”). We opened with some “What if?” statements, such as: What if you get answers from complex queries faster than your competitors? What if you could do that without the cost, complexity, delays, and limitations of a Star Schema or pre-aggregated data? What if you could do this on commodity x86 hardware? We would then briefly cover the breakthrough technology (which was a precursor to Snowflake) and offer a free half-day meeting with a consultant.
Within the first two weeks, we met with a company that was later acquired by PayPal shortly before eBay acquired PayPal. This company was about to spend $500K on a proprietary hardware expansion that would have only provided additional capacity for the following year. Their customers bought advertising based on queries against the last six months of their data. I asked the question, “What if they could query against five years of data and get answers faster than they do today? Do you think that would help them buy more advertising? Do your customers ever ask for this?” The response was that their customers frequently ask for 12 months of data and would be willing to pay more for these capabilities. Still, they did not have a way to do this cost-effectively.
I closed a $250K ARR subscription deal in two weeks, and they purchased $140K of commodity Dell hardware for our software to run on. They saved 20% over their planned purchase, and more importantly, they rolled out advanced querying capabilities (against six years of data) in less than a month. There was incredible value to them and their customers, and it generated more business for them. We would not have identified this need if we had primarily focused on features and technology.
As an aside, I was initially chastised for going off message, but after the Australian team adopted our approach and began closing deals, it became the new corporate standard. If something isn’t working, focus on finding ways to improve it. Even incremental change can be meaningful.
In the words of Tony Robbins, “If you do what you’ve always done, you’ll get what you’ve always gotten.”
Where Ideas, Experiences, and Lessons Learned Intersect 