strategy

Playing to Win, versus Playing Not to Lose

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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?

This entry was posted in Business Ownership and Management, Change Management, Consulting, innovation, leadership, strategy and tagged , , , , , , , , , , .

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.

This entry was posted in Business Ownership and Management, Career, Consulting, innovation, leadership, Life, Selling, strategy and tagged , , , , , , , , , , , , , .

Leading Next-Generation Sales Teams: The Mandate for Predictable Revenue

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An image of a hand pointing to an AI generated dashboard on a computer screen.
Image created by Nano Banana

The sales landscape has fundamentally shifted. I keep reading posts and stories about AI replacing sales teams, and it may be for more commodity-type sales, but it will be some time before it replaces Enterprise sales teams. Building relationships and trust is the foundation for an executive to take a risk on your product, especially when it is critical to their success. AI is not yet at that level, and as behavior changes with every key release, building trust in AI will be challenging for many years to come. But today, AI can be a powerful enablement tool for your team when leveraged correctly.

Your prospects no longer need salespeople for information; they need us for Insight. They have done their research. They expect their time to be an investment, not a discovery exercise. Does your presence and knowledge project confidence and inspire trust? Does the prospect view you as someone interested in helping their business, or just someone trying to close a deal? Impress them, and you could earn the opportunity to dig deeper. Disappoint them, and good luck recovering.

Two years ago, I was selling to a Fortune 100 Financial Services company. I understood their business needs, and we met them easily. We demonstrated that we could take a key manual process that typically took 7 weeks to complete, automate it and maintain full compliance, and complete the task within 10 minutes. The SVP told me his priorities for selecting any new vendor were: 1 – Company Stability; 2 – Relationship with the Vendor; 3 – Product Quality; 4 – Product Value to their business; and 5 – Total Solution cost. Before selling their IP, the company fired the sales team, and the remaining execs stepped in and offered the deal at an even greater discount. It never sold because the executive team didn’t understand what mattered to this buyer. The company had a high-level relationship with the stakeholders, but lacked the trust and credibility that I had built over several months. This is one of the main reasons why I believe AI won’t take over Enterprise Sales anytime soon.

So, how do you get it right?

The question for every CRO or VP of Sales isn’t whether their team is busy, but whether their activity is revenue-focused and drives predictable, scalable results. There’s plenty of money to be made, but following the same old tired formulas seldom works.

For leaders aiming to build next-generation teams that deliver zero surprises in the forecast, the approach must be recalibrated around three core pillars: Strategic Preparation, High-Agency Coaching, and Outcome-Focused Messaging (“context”). It is much more than cold calling for two hours a day or having 5-10 meetings per week. Those things matter, but they are just activities if you are not targeting the right companies and people, or if your team blows it once you have found them. This will be a significant cultural shift for many companies.

Strategic Preparation: From “Discovery” to “Insight”

When a prospect books a meeting, they are giving us one of their most precious assets: time. If we treat that time as a standard discovery call, we set negative expectations, which signals the lack of perspective (the ‘P’ in PIE) and perceived value. This isn’t theory—it’s the PIE framework (Perspective, Insight, Experience) I’ve used for years to sell large deals, turn around at-risk customers, and scale teams.

The C-Suite Mandate: Accelerate deal velocity by focusing on specific quantifiable impact for your prospects, and increase win rates by targeting identifiable business pain.

  • Come with an Understanding of their Market, Changes, and Competition. Before the first call, we must show we’ve already invested time in understanding their operational constraints, competitive pressures, and budget priorities. The goal is to move the conversation immediately from the tired, “What keeps you up at night?” to “We have seen [problem] with companies in your industry. Is that something you have experienced or have concerns about?”
  • Long Discovery Calls or Presentations Typically Won’t Work. Customers are fatigued by generic questions. Every interaction must be purpose-driven and meaningful. If the call runs longer than planned, it must be because the conversation has become mutually valuable, not because the seller was ill-prepared and just kept talking.
  • Discussions Must Be Targeted to the Problems They Are Most Likely Experiencing. This is where we leverage Insight (the ‘I’ in PIE). Use your background and AI to hypothesize the top three pain points before you dial. Our role is to validate these points, quantify the impact, and then introduce a Shared Vision of Success (our solution) anchored by measurable business outcomes.

Player-Coach: Enhancing Team Capabilities, Not Just Motivating Activity

If you are a sales leader who only focuses on closing your team’s most challenging deals, you are creating a dependency, not a capability. A Player-Coach must be accountable for the team’s numbers and its health. That can be a big job.

The C-Suite Mandate: Drive organic growth by building repeatable processes and cultivating high-agency talent.

  • Not a One-Size-Fits-All Proposition. True coaching is not a template. It requires a methodical but human approach to diagnostics. That takes time, effort, and a genuine desire to help people grow.
  • Identify Skills Gaps and Tailor Efforts. Test skills, identify gaps, and create targeted efforts to build skills that address someone’s specific deficiencies. This personalized attention builds the high-performance culture and accountability required to sustain long-term success.
  • Leverage the Team – Role Playing and Team Reviews. We must create a culture where knowledge sharing and feedback loops are the norm. Leverage team reviews and structured role-playing to sharpen execution. This is how we transform luck into a predictable process.

Give teams the latitude to adjust their messaging and test approaches. Adapt messaging to business trends, changes in the competitive landscape, and changing terminology. Then, have your team share their experiences and findings (good and bad) for review, feedback, and refinement. Structured agility helps your team maintain its competitive edge.

The Leadership Mandate: Context Over Content

We are past the AI hype cycle. The C-Suite doesn’t care about the tool; they care about the ROI and the risk of poor execution. As leaders, we cannot just hand our teams a login and say, “Go use AI.” That’s a recipe for chaos and a quick erosion of professional credibility. We must lead by example.

We need to teach our teams that AI generates content (not always accurate), but humans provide context. The two work hand-in-hand.

  • Do use AI to deepen your understanding of the prospect’s industry so you can become a true consultant. Use the technology to gain understanding and market intelligence and tie it to your Experience (the ‘E’ in PIE) as preparation before any call.
  • Don’t use AI to automate a thousand bad emails. Mass communication is cheap; individualized insight is priceless.
  • Do use AI to research the one hundred prospects that actually matter. Focused efforts yield significantly better results.
  • Don’t use AI to fake expertise. This can quickly kill credibility, as any good consultant will tell you.

The “Million Dollar Deal“ isn’t won by a bot. A human wins it by understanding the nuances of the prospect’s business, building trust, and navigating the internal structure and politics. AI is simply the tool that clears the path so you can do that work faster and with better data. AI is leverage, not a crutch.

Call to Action: Are You Building a Team or a Capability?

The next-generation sales leader understands that customer success is at the heart of everything we do. We win when they succeed. Your most valuable asset isn’t your pipeline—it’s the predictable capability of the individuals on your team. Consistently doing the right things is critical to success.

The challenge for every business leader today is this: Are you enabling your teams to sell like consultants, or are you still measuring them (and driving their behavior) on activity-based metrics? Focus on building intelligent and creative teams that deliver consistent results with zero surprises. It doesn’t happen overnight, but it is an investment in your future success.

Let’s discuss how we can implement the PIE framework and position your team to deliver scalable, organic growth.

This entry was posted in Artificial Intelligence, Business Ownership and Management, Consulting, innovation, leadership, machine learning, Selling, strategy and tagged , , , , , , , , , .

Lessons Learned from GTM Consulting

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For the past two years, I have performed part-time, contract go-to-market consulting. My wife had a surgery that went 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. What I encountered was quite different from what I expected, so I thought I would pass it along.

A generated image of a male consultant working with a sales team.

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 often lack the budget for what they view as a solution that increases complexity.

Here are my Top 5 findings:

  1. GTM plans are often developed at the highest levels, often in isolation, without market testing and validation.
    • An interesting aside is that the company is often really seeking sales optimization but believes it is doing things “well enough” today and therefore needs to focus on new offerings and revenue streams.
    • New perspectives on past performance and failures are well received but more surprising than anticipated. This leads to a better understanding of needs, which builds consensus moving forward.
  2. Sales teams are sometimes pitted against one another, rather than working together to help everyone achieve more (Coopetition – “A rising tide lifts all boats.”)
    • Sometimes the competing team isn’t sales, but support. The team wants to help the customer (which is great), but works outside its defined scope instead of bringing in the services and sales teams to work jointly to solve the customer’s problem.
  3. Sales teams are focused on selling features rather than solving business problems.
    • Training those teams on solution selling and understanding the prospect’s needs pays off.
  4. CRMs are not consistently used and often reflect idealized fiction rather than reality.
    • Old, dead, or unqualified opportunities; lack of recent contact or interaction; deals that have slipped more than once; and a lack of understanding (company, needs, players, business environment) all point to an unrealistic pipeline.
  5. Sales management and teams are not leveraging AI to help focus their efforts.
    • Conversely, they may view AI as a panacea, investing time and money in tools that supplement a strong team rather than focusing on strengthening the team.

Here are the related Lessons Learned:

  1. 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.
    • Here’s solution sales again. Teaching teams to ask better questions, listen more, and validate their understanding increases their standing with prospects.
  2. 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 other companies describe those problems? Their terminology, often found in job postings by competitors and your target audience, can help create effective messaging that resonates. Work to become the natural fit for what your prospects are seeking and the problems they are likely dealing with.
  3. Individual contributors get paid to win, but sales management needs to create incentives for collaborative efforts that lead to both wins and ongoing customer growth.
    • Paying sales teams for net new business only causes them to ignore install base expansion opportunities. And, if another vendor solves their problems, it is only a matter of time before they replace you.
    • 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 tailor and fine-tune their efforts.
  4. CRMs often either lack information or are full of wishful thinking. They focus on activities, and not progress and next steps.
    • Using MEDPICC as a foundation for qualification is a much better start.
    • Sales managers need to validate the information independently to ensure their teams are upfront and honest. Trust, coaching, and collaboration work together for the win.
    • Chasing deals that are unlikely to close wastes valuable resources.
  5. 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 helps you quickly qualify prospects in or out.
    • There may be opportunities to nurture prospects who have potential but aren’t qualified for immediate deals, seeding the pipeline for future opportunities. This could be a great place to leverage AI for personalized journeys with highly relevant curated content.

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 assistance with your business, contact me.

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