Life

The Strangest Feedback I Ever Received

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My first job after my consulting company shut down was building a consulting organization for a spinoff database company. The CEO called me the week before, then invited me to meet him in Manhattan the following week. We met for a few hours, then he handed me a piece of paper with a title and salary. I thought about it for a minute, shook his hand, and said, “Thanks, boss.” We devoted the next few days developing a vision for the team that would boost sales and drive greater customer success.

We worked closely for the next six months, but there were times I could tell that I frustrated him. For example, we once met with a top 3 credit card company. They presented their needs, and he told them we could easily handle it.

On the way back to the hotel, I explained the architectural limitations that would make the project very challenging. Then I presented multiple ideas to accomplish what they needed – just not in the way they envisioned it. My focus was on creating a deal that worked, and not just closing a deal that could ultimately hurt our reputation.

A year or so later, I was on a multi-city road trip to visit customers and prospects with each member of the sales team. It was a Thursday afternoon; I had just arrived at a hotel in San Diego where I’d stayed dozens of times over eight years, and I was relaxed and feeling great.

The CEO called, telling me that one of the architects he hired had just given his notice, and asked me if I thought we should try to get him to stay. I explained that this person was extremely talented and worked well with everyone, but he wasn’t working on the things he was hired to do and had been noticeably unhappy for the past several months. I asked if we planned to revive the project this person helped develop, and the answer was ‘no’.

I went on to explain that while this guy was a great person and technical asset, he wasn’t a good fit for the company now or where it was heading, which is why I recommended letting him go. I said we could use his salary to hire one or two people interested in our current direction and get a better return on that investment.

To me, this was a logical decision, and not an emotional one. Most companies have limited resources, and to win, you need to find the greatest leverage for every dollar spent.

His response was, “The thing I love about you is also the thing that I sometimes hate about you.”

A man in suit standing in front of a mirror that has two reflections. One is overly positive, while the other reflects reality.
“Reflections” created by Nano Banana 2

There was a brief pause of silence, then I replied, “OK, I’ll bite. What is that?” He said that, unlike everyone else who reported to him, I consistently told him what he needed to hear instead of what he wanted to hear. He told me he valued my perspective, which is why he called, but I often frustrated him by telling him something contrary to his beliefs.

This candid conversation didn’t damage our relationship, and it reinforced a core truth about leadership: loyalty demands clarity first, then compliance.

Safe leaders surround themselves with “yes-men” to protect their egos. Exceptional leaders seek out individuals who care enough about the mission and its success to risk temporary friction. This is about doing the right thing, versus who is right.

Leaders should create an environment where all opinions and data are welcomed during the planning phase. Disagreement isn’t disrespect; it is a risk-mitigation strategy. This is where clearly articulating your concerns persuasively helps. True alignment sometimes requires strong but professional debate behind closed doors: looking for flaws and weaknesses in a plan, refining it as needed, and then executing the final decision as a unified team.

So, do you have the courage to provide the truth – even if it is unpopular? Can you do so in a convincing and professional manner? They might hate it in the moment, but they will value your integrity in the end, especially if you are seen as someone focused on improvement and success, and not just a contrarian.

This is what should be expected of executives within an organization, for the overall good of that organization.

Curiosity-Led Execution

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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:

  1. Establish credibility
    Demonstrate enough expertise early to build confidence.
  2. Lead with curiosity
    Ask thoughtful, relevant questions that show genuine interest—not interrogation.
  3. 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.

Getting Your Piece of the PIE

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Whether you are selling, consulting, or managing, a foundational approach has consistently helped me succeed. I call it PIE – an acronym that stands for Perspective, Insight, and Experience. When applied effectively, these three elements provide a robust framework for solving problems, winning clients, and leading teams to remarkable outcomes.

Over the years, I’ve taught this methodology to my teams, and it’s been a critical driver of their success. While I usually reserve it for a small circle, I believe it’s time to share it more broadly. I built this methodology and other structured approaches/methodologies as part of developing high-performance teams. They provide the foundation for rapid qualification and faster wins.

Approaches like these are required for consistent, reliable, and scalable organic growth

Perspective – Broaden Your View to Stand Out:

To truly differentiate yourself in any field, you need a broad, informed perspective. This involves understanding the larger environment in which you operate: the market, competitive landscape, customer needs, technological advances, and regulatory shifts. A dynamic perspective evolves as you gain new experiences and encounter different approaches to solving similar problems across other businesses or industries.

This requires a broad understanding of the environment, market, competitive landscape, legal and technological changes, and more. It also grows and changes as you experience new and different things—especially when different approaches to similar problems are taken. It is how you start to stand out in the eyes of your prospects, customers, and team.

Earlier in my career, I taught technical courses. Usually, two or three people stood out. At least one wanted to prove they were better and smarter, and usually, one discussed strange approaches to solving problems. When you dug into those strange approaches, you often found something creative and brilliant coming from a different perspective on the problem. Curiosity and a desire to improve often drove their innovative approaches.

In business, perspective becomes your differentiator. When you can see things from a broader, more holistic viewpoint, you position yourself as someone who can offer more than just solutions—you offer foresight, adaptability, and creativity. You become the lighthouse that guides your clients around tricky situations and to a better destination.

Products create interest. Perspective creates confidence.

How to Apply This:

  • Stay informed about industry trends, not just within your niche but across related sectors.
  • Engage with diverse thinkers, challenge your assumptions, and be open to unconventional ideas.
  • Regularly reassess your strategies in light of new information or shifts in the business environment.

Here is a post that discusses perspective as the starting point.

Insight – The Power of Seeing What Others Don’t:

Insight is one of the most valuable assets you can bring to any business interaction. Too often, people are trapped by existing tools, processes, and perceived constraints. Insight lets you cut through these limitations and spot opportunities for improvement that others miss.

Here’s where perspective plays a role in insight: the broader your view, the better you can generate actionable insights that can transform a business. My most successful deals and projects were not won because I followed the status quo—they were won because I brought fresh ideas to the table. By reframing the problem and presenting a path to a better solution, I created value that competitors cannot match.

How to Apply This:

  • Question assumptions and typical approaches. Ask yourself, “Is this really the best way to solve the problem?”
  • Look for inefficiencies, bottlenecks, and areas of waste in processes. These are often hidden opportunities for innovation.
  • When engaging with clients or teams, offer insights that reframe their challenges and provide a path to improved outcomes by focusing on the “what” rather than the “how.”

Here’s a post that delves deeper into insightfulness.

Experience – The Foundation of Wisdom and Credibility:

Experience is the foundation that supports both perspective and insight. It’s the repository of lessons learned—both successes and failures—that shape your approach to problem-solving and innovation. The more varied and in-depth your experience, the better equipped you are to offer valuable insights and strategies.

Consulting, in particular, is fertile ground for gaining diverse experience. By working with multiple clients across industries, you gain exposure to a wide array of challenges and solutions. In sales, this experience translates into powerful stories that illustrate your ability to help clients achieve better outcomes. The more experience you accumulate, the more confident you’ll become in your ability to deliver meaningful results through transferable competence (taking skills and lessons learned from one domain and applying them to another).

How to Apply This:

  • Reflect on your past experiences—what worked, what didn’t, and why. Use these lessons to guide future decisions.
  • Build case studies from your experiences to demonstrate your expertise and credibility when engaging with clients or stakeholders.
  • Continuously seek out new challenges that stretch your capabilities and expand your knowledge base.

As Albert Einstein wisely said, “The only source of knowledge is experience. You need experience to gain wisdom.” But it’s not just about accumulating experiences—it’s about leveraging them. Your past successes build confidence in your abilities, while your failures provide invaluable lessons that help you avoid costly mistakes in the future.

Perfection is the Enemy of Progress

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Winston Churchill photo with the British flag as a background.

The title is a quote from Winston Churchill. I have learned in my career that these behaviors can be very costly from a business perspective, especially when decisions affect large parts of a business. It took me years to learn this lesson as I transitioned from perfectionist to “reformed perfectionist,” which was challenging.

Below are a few examples that could help you better understand people like this, and if you are someone like this, it might even provide motivation to try to change.

Early in my career, as I expanded my role from Programmer to Analyst Programmer to Systems Analyst, I often found myself spending too much time and effort on things that had minimal impact. Applications and subsystems looked a little better, ran a little faster, integrated more easily, were easier to modify, and generally had fewer problems. Those are all good things, but in hindsight, those benefits often did not justify the associated costs. 

Some industries and applications require a degree of quality and reliability, such as nuclear power plants and lifesaving medical equipment. Since very few things are perfect, there are usually a variety of built-in safeguards to mitigate the impact of errors and failure. I have worked on a few of those systems, and I get it. But they are not in the majority. 

Identifying the intersection of meeting the stated requirements, delivering the required quality, and knowing what “good enough” looks like is essential. That’s where diminishing returns set in for every additional hour spent on an activity.

I worked with a hardcore perfectionist at a small software and services company. On a consulting engagement, he spent two days on a task that I viewed as a 2-4 hour effort. We discussed it, and he told me he had at least three more days to finish. We had a heated discussion, and he was frustrated with me for a while. Years later, he admitted I was right, talked about how difficult it was to change, and how much more productive he is now. 

I had a consulting engagement with a small software company that spent 10+ years on a SaaS product and was always “just two to three weeks away” from their MVP (minimum viable product). I started working with them over three years ago, and they are still at that point today. Software is never perfect, so waiting for perfection can kill a company.

I have also sold to companies stuck in analysis paralysis because they (leaders and teams) are always second-guessing decisions and want to be 100% certain before making a decision. Those companies need to solve a problem, or they would not be seeking a solution. In most cases, making an informed decision on a proven solution now will solve their problems and deliver value quickly. There is an actual business cost for every month of delay. 

Are these behaviors costing you or your company money? If yes, dig a little deeper to understand the potential positive impact making small changes could have. Daily improvement is a great thing!