Stepping Stones and Cornerstones

The High Cost of Transactional People

If you spend your career building—whether that’s technology systems at a Fortune 50 company or the operational framework of a growing MSP—you learn a fundamental rule of construction: Not all materials are meant to bear weight. If you try to build a skyscraper on a foundation of drywall, it will collapse. You have to know the difference between the materials that look good on the surface and the materials that can actually hold the building up.

The same is true for human infrastructure.

In business, and in life, you will encounter two types of people: Relational builders and Transactional extractors. I call them Cornerstones and Stepping Stones.

Learning to tell the difference between the two is one of the most painful, but necessary, lessons in leadership. And if you have a "Fix-It" mentality like I do, it is a lesson you will likely have to learn the hard way.

The Fix-It Magnet

Because my childhood taught me to find safety in solving problems, my default setting in the corporate world was to provide immense value. As an INTJ, if I saw a broken process, I fixed it. If I saw a struggling peer or a direct report who needed mentoring, I poured my time, my strategic thinking, and my political capital into them. I assumed that when you invest deeply in someone, you are building a Cornerstone relationship. I believed that mutual effort created mutual loyalty. I was wrong.

What I didn't realize was that high-functioning "Fixers" are absolute magnets for Transactional people. When you naturally provide value, structure, and solutions, transactional people will flock to you. They will eagerly consume your emotional and professional investment while offering nothing in return. The trap is assuming their proximity means loyalty. When you naturally produce results, you attract people whose only goal is to consume them.

The Illusion of Loyalty

A Stepping Stone relationship can look deceivingly like a Cornerstone at first. They will flatter you. They will seek out your advice. They will gladly let you mentor them, review their presentations, or introduce them to your network. But the fatal flaw is the direction of the energy. It is a one-way sync.

I have learned this lesson through painful experience. There have been times in my career where I brought people under my wing, advocated for them behind closed doors, and spent hours of my own time helping them secure their next promotion or land a massive client. I thought we were in the trenches together. I thought we were building a foundation.

But the moment they got what they needed—the title, the introduction, the credit—they vanished. The lunches stopped. The collaborative emails ceased. When the time came that I needed an advocate or a favor, they were suddenly "too busy." It is a jarring, hollow feeling. When you realize you weren't a partner to them, but merely a tool they used to cross a river, it leaves a unique kind of professional heartbreak. It makes you want to lock the vault, compartmentalize your empathy, and never invest in another person again.

Spotting the Tells

You cannot lead effectively if you become cynical and refuse to trust anyone. But you must become highly discerning. You have to learn the "tells" of a Transactional person before you spend your most valuable asset—your time—on them. Here is how you spot a Stepping Stone:

• The "Emergency" Imbalance A transactional person's crisis is always an all-hands-on-deck emergency that requires your immediate attention. But when you are facing a crisis, they offer empty platitudes or disappear entirely. They are happy to make withdrawals from your emotional bank account, but they never make deposits. Their emergencies are always your problem, but your emergencies are an "inconvenience" to them.

• The Scoreboard Relational people give because they care about the health of the system and the success of the team. Transactional people keep a ledger. Everything is a trade. If they do you a minor favor, you will quickly be reminded of the debt you owe them. They keep score. Everything is a trade: "I did X for you, so you owe me Y."

• Upward Adoration, Downward Apathy Watch how they treat people who cannot do anything for them. A Stepping Stone will be incredibly charming to a VP or a Director, but dismissive of an intern, an administrative assistant, or a vendor. If their kindness is conditional on a person's title, their loyalty to you is conditional on your usefulness. They only reach out when they need a roadblock cleared or an introduction made.

Guarding the Architecture

The lesson here is not to stop helping people. The lesson is to stop trying to build load-bearing walls out of cheap materials. You can work with Stepping Stones. You can collaborate with them on a project. You can be polite, professional, and effective. But you must mentally reclassify them. Do not give them the premium access, the deep mentorship, or the emotional vulnerability that you reserve for the Cornerstones.

The Pivot: How do you recover without becoming cold and cynical? You don't stop being relational; you just get smarter about who gets your premium investment. You learn to match energy. You can operate transactionally with transactional people (giving them exactly what the job requires and nothing more), while saving your deep, relational investments for the people who actually want to build alongside you.

Invest in the leaders, friends (and even family) who match your energy, who stand by you when the project fails, and who view your relationship as a foundation to be protected, not a resource to be extracted.

The Architecture of a Cornerstone: Identifying Relational Leaders

It is easy to become defensive after you’ve been burned by a Stepping Stone. But if you lock down your network entirely, you stop building. You cannot scale a system or a career on your own. You need load-bearing walls, and that means you have to get incredibly good at identifying the Cornerstones—the relational people who are actually worth your premium investment. While Transactional people operate on a one-way extraction protocol, Relational people operate on a bi-directional sync. They understand that a healthy system requires both give and take. Here is how you spot a Cornerstone in the wild:

• Symmetrical Support: When they are in a crisis, they ask for your help. But when you are in a crisis, they don't just offer empty words; they roll up their sleeves and ask, "What part of this can I take off your plate?" The data flows both ways.

• The "System Health" Mindset: Transactional people only care about their individual metrics. Relational people care about the overall health of the environment. They are the ones who stay late to help a peer troubleshoot a server issue or rewrite a difficult email, even when there is no direct benefit to their own performance review.

• They Deflect Credit and Absorb Blame: A true Cornerstone acts as a shield for their team and a mirror for their successes. When the project launches flawlessly, they point to the people who built it. When the system crashes, they stand in front of the executives and say, "I own this."

How to Invest in the Foundation

Once you identify a Cornerstone, you must intentionally shift how you interact with them. You cannot treat them with the same guarded professionalism you use with Stepping Stones. You have to pour concrete.

1. Grant Premium Access Time is an executive's most precious resource. Stop giving it away to people who only want to use you. Protect your calendar ruthlessly from the extractors, and reallocate that time to your Cornerstones. Give them the unvarnished truth, the behind-the-scenes strategy, and the vulnerability that you hide from the rest of the organization.

2. Shift from "Fixing" to "Sponsoring" If you have a "Fix-It" mentality, your instinct will be to just do their work for them when they struggle. Don't. You invest in a Cornerstone by elevating them, not by enabling them. Use the political capital we talked about in the last chapter to become their Sponsor. Say their name in the rooms they aren't in yet.

3. Check in When There is No Crisis Transactional people only call when the server is down. You prove your relational investment by calling when the system is running perfectly. Reach out just to ask about their family, their golf game, or their weekend. Prove to them that their value to you is not tied exclusively to their output.

Refactoring Your Own Code: How to Become a Cornerstone

It is one thing to look for Relational people; it is entirely another to ensure you are actually being one yourself. For high-achieving, data-driven leaders—especially those of us who pride ourselves on operational efficiency—becoming truly relational requires an intentional rewrite of our own internal code. We are wired to value results, ROI, and logic. But human infrastructure is messy, emotional, and inefficient. If you want to be a Cornerstone for others, you have to practice these three disciplines:

• The Discipline of Listening Without Solving: This is the hardest skill for a Fixer. When a peer comes to you with a problem, your brain immediately compiles a five-step action plan. Stop. Sometimes, they do not need an architect; they just need a sounding board. Learn to ask, "Are you looking for a solution right now, or do you just need to vent?"

• The Discipline of the Long Game: Transactional people operate in sprints. Relational people operate in decades. You have to be willing to invest in someone today knowing you might not see the ROI for five years.

• The Discipline of Valuing the Person Over the Output: In corporate life, it is perilously easy to view people as simply a means to an end—resources to be deployed to hit a quarterly target. To be a Cornerstone, you must fundamentally believe that the people on your team have inherent value regardless of their title, their metrics, or their utility to you.

When you shift your mindset from extracting value to building capacity, you stop just managing processes. You start architecting leaders.