Choose Your Circle Wisely: Why the People Around You Determine How Far You Go

“The people you surround yourself with in personal and professional life shape your standards, your decisions, and your destiny, and not everyone in your circle has your best interests at heart.” — Laurent Pierre Jr.

The quality of your inner circle will define the quality of your leadership. Who is in yours?

The Day I Realized Not Everyone Was In My Corner

Early in my career, I was still young, still hungry, still believing that everyone who smiled at me in the hallway was genuinely rooting for me; I made a mistake that many ambitious people make. I confused proximity with loyalty. I confused shared history with shared values. And I paid a price for it that I still think about today.

There was someone in my circle at the time. We had worked together, laughed together, and leaned on each other during hard stretches. I considered this person one of my trusted advisors. When an important opportunity came up a career-defining moment I opened up completely. I shared my fears, my plans, my vulnerabilities. What I didn’t know then was that this same person was quietly carrying my confidences to others. Not out of malice, exactly —I’ve long since made peace with it—but out of self-interest. My advancement, it turned out, was not in their interest. And so, in ways subtle enough to be deniable and calculated enough to matter, they worked against me. I didn’t see it until the damage was done.

I’m not telling this story to relitigate the past or to assign blame. That chapter is closed, and I genuinely wish that person well. I’m telling it because that moment fundamentally changed how I think about choosing the right people to let into my life and my leadership. It taught me that the most dangerous threats to your trajectory are rarely strangers. They are the people sitting at your table. And if you are a leader — or aspiring to become one — understanding the composition of your leadership inner circle may be the most consequential strategic decision you ever make.

The Hard Truth Nobody Likes to Say Out Loud

Let me be direct with you, because I believe you deserve directness: not everyone who calls themselves your friend, mentor, or advisor is working in your favor. Some are passive — they simply don’t invest in your growth, showing up to consume the energy and opportunity of your relationship without contributing to it. Others are more active — they subtly undermine you, share your vulnerabilities in conversations where your name deserves to be protected, or quietly celebrate your stumbles in private while offering you a hug in public. I know that’s hard to read. It was hard to live through. But I also know that the leaders who recognize this truth early are the ones who go further, build better, and lead with greater integrity.

In my experience — across more than three decades at IBM, Microsoft, NielsenIQ, and now Precisely — I’ve come to recognize that most circles contain three kinds of people. Understanding the difference between them isn’t cynical. It’s essential.

The Three Types in Most Circles

• The Builders: They invest in your growth, celebrate your wins without reservation, tell you the truth when it’s uncomfortable, and show up when it costs them something. These people are rare and precious. Protect them fiercely.

• The Bystanders: Neutral by disposition. Neither helping nor harming, they are passengers in your journey — consuming without contributing. They’re not malicious, but their presence can create a false sense of community. Proximity without purpose is not a circle; it’s a crowd.

• The Blockers: Subtly competitive, quietly self-interested, or privately threatened by your growth. They may cheer the loudest at your successes in public, but they are the first to offer “context” about your failures to others. They are the most difficult to identify precisely because they have mastered the language of support while practicing the art of sabotage.

You don’t need to become paranoid. You need to become discerning. There is a profound difference between the two. Paranoia closes you off from connection entirely. Discernment helps you choose connection wisely. And wise choices, made consistently over time, shape destinies.

“Your circle shapes your standards. Your standards shape your decisions. Your decisions shape your destiny. Choose wisely.”

— Laurent Pierre, Jr.

When History’s Greatest Leaders Got It Wrong: Four Cautionary Tales

This is not a theoretical problem. The failure to choose your circle wisely has toppled empires, collapsed billion-dollar companies, and sent once-celebrated leaders to prison. Let’s examine four of the most instructive cases in history — because I believe there is no teacher quite like a well-studied failure.

I. Julius Caesar and Decimus Brutus (44 BC)

Most people know the name Brutus in connection with Caesar’s assassination. But most people think of Marcus Brutus — the idealistic senator. The man who arguably did more damage was Decimus Brutus, and his story is far more instructive for leaders today, because Decimus was not a rival. He was Caesar’s most trusted military commander, his closest ally, and — according to the ancient historian Cassius Dio — the man Caesar himself identified as his most reliable confidant. The night before the Ides of March, 44 BC, Decimus dined with Caesar. They broke bread. They shared the intimacy of men who had campaigned together, who had survived together.

The next morning, Caesar was uneasy. His wife Calpurnia had been shaken by premonitions and begged him not to go to the Senate. Caesar wavered. And then Decimus appeared at his door. Not with a weapon — with words. He appealed to Caesar’s pride, suggesting that staying home would be perceived as weakness, that the Senate would mock him, that a man of his stature could not afford the optics of fear. Caesar, moved by the counsel of his most trusted advisor, walked to his death that day. He was stabbed 23 times by a group of senators — led in large part by the man he trusted above all others. Barry Strauss, writing for HISTORY.com on March 15, 2018, called Decimus “Julius Caesar’s Forgotten Assassin” — forgotten precisely because the betrayal was so complete, so personal, and so hard for history to process.

The lesson for leaders: Proximity is not loyalty. The people closest to you have the greatest access — and therefore the greatest capacity to either protect you or destroy you. Be cautious about who earns that proximity, and never confuse shared history with shared values.

II. Kenneth Lay, Jeffrey Skilling, and the Enron Circle of Yes (2001)

The collapse of Enron is one of the most studied corporate disasters in modern history, but we rarely examine it through the lens of circle failure. That’s the lens I want to use here. Kenneth Lay and Jeffrey Skilling built their inner circle at Enron from a carefully curated collection of enablers — a complicit board, an auditor (Arthur Andersen) whose judgment was compromised by the consulting fees Enron paid them, and executives who were richly rewarded for playing along with financial structures that defied both logic and law.

In August 2001, Vice President Sherron Watkins sent a direct, courageous memo to Kenneth Lay warning him that “Enron will implode in a wave of accounting scandals.” She was specific. She was right. And she was the kind of truth-teller that every leader’s circle desperately needs. Rather than act on her warning, Lay reportedly consulted his inner circle — who, according to accounts of the scandal, wanted to dismiss Watkins entirely (Texas law ultimately prevented them from doing so).

The warning was absorbed, minimized, and ignored. By December 2, 2001, Enron had filed for bankruptcy in what was then the largest corporate collapse in U.S. history: $63.4 billion in assets wiped out, 20,000 employees losing their jobs and their retirement savings, Arthur Andersen dissolved, and Jeffrey Skilling ultimately convicted and sentenced to 24 years in federal prison.

The lesson for leaders: A circle that protects your ego instead of your integrity will eventually cost you everything. The most valuable person in your circle is not the one who confirms your vision — it is the Sherron Watkins who has the courage to challenge it. When that person shows up, listen. If your circle has conditioned you to dismiss them, rebuild your circle.

III. Adam Neumann and the WeWork Mirror (2019–2023)

Adam Neumann did not suffer from a lack of ambition. He suffered from a circle that reflected his ambition back at him without ever questioning it. His board and investors granted him supervoting shares — 10 votes per share versus 1 for everyone else — effectively making Neumann untouchable by the very governance structures that exist to protect organizations from unchecked leadership. No one in the room had the structural standing, or the personal incentive, to tell him the truth.

When WeWork’s S-1 IPO prospectus was released in 2019, what the circle had collectively chosen not to see was suddenly visible to every outside observer simultaneously: staggering losses, self-dealing transactions, and a governance architecture built for the benefit of one man. NYU professor Scott Galloway described the document as containing what amounted to “weapons-grade” misrepresentation.

The company’s valuation — once celebrated at $47 billion — collapsed by 83% to approximately $8 billion in just six weeks. The IPO was pulled. Neumann was ousted. Employees whose stock options had been granted at higher valuations were financially devastated. SoftBank, which had invested $10.6 billion, was forced to execute an emergency rescue. WeWork ultimately filed for bankruptcy in 2023. As reported by Stratrix Strategic Forks in March 2026, the WeWork saga remains a defining case study in what happens when a circle is structured to amplify a leader’s vision rather than test it.

The lesson for leaders: A circle that reflects your greatness back at you without challenging your blind spots is not a circle — it’s a mirror. And mirrors cannot save you. The structures you build around your leadership must include voices with the standing and the will to say no.

IV. Elizabeth Holmes and the Theranos Board of Prestige (2003–2018)

Elizabeth Holmes assembled one of the most visually impressive boards in the history of Silicon Valley: Henry Kissinger, former Secretary of Defense James Mattis, former Secretary of State George Shultz, former Secretary of Defense William Perry, and other luminaries of American public life. On paper, the circle looked invincible. In practice, it was hollow. What the board lacked was as stunning as what it possessed: not a single member had expertise in diagnostic laboratory science — the one field that Theranos actually operated in. There was no audit committee, no technical oversight committee, and no standing body tasked with substantive risk review. The board met infrequently and relied entirely on Holmes for information about the company’s operations.

According to governance analysis by Global Link Law and a postmortem examination by researcher David Shadrake, prestige had been systematically substituted for expertise and accountability. When whistleblower Tyler Shultz — the grandson of board member George Shultz — raised internal concerns about the accuracy of Theranos’s blood tests, those concerns were dismissed. The technology, as the world eventually learned, did not work as claimed. Patients received inaccurate blood test results that affected real medical decisions about real human lives. Holmes was convicted on four counts of wire fraud and conspiracy in 2022 and sentenced to 11.25 years in federal prison. More than $700 million in investor capital was lost. The reputations of distinguished public servants were tarnished by association.

The lesson for leaders: The right names in your circle mean nothing if they don’t ask the right questions. A circle built for appearance rather than accountability will eventually fail you publicly — and the more impressive the names, the more catastrophic the fall.

The Common Thread: What Every Failed Circle Had in Common

These four stories span millennia and industries — ancient Rome, corporate America, Silicon Valley, the American public markets. And yet they share a strikingly common anatomy of failure. When I look at them together, three characteristics appear in every case:

Failure Pattern	What It Looks Like	Historical Example
Proximity Without Integrity	Being physically or emotionally close without being honest. Warmth that substitutes for truth.	Decimus dining with Caesar the night before the assassination.
Prestige Without Accountability	Impressive titles and associations, no mechanism or will for genuine challenge.	The Theranos board: former Secretaries of State and Defense, zero lab scientists.
Agreement Without Wisdom	Yes-people who protect the vision at the expense of the truth, often incentivized to do so.	Enron’s compliant board ignoring Sherron Watkins’s warning. WeWork’s supervoting structure silencing dissent.

The pattern is consistent enough to be a law: when the people around you are more invested in your comfort than your correctness, eventual failure is not a risk — it is a scheduled appointment. The only variable is when it arrives.

A Leadership Truth Worth Writing Down

The most dangerous person in your circle is not the one who challenges you. It is the one who never does — and calls that loyalty.

The CIRCLE Audit: A Framework for Evaluating Your Inner Circle

Over the course of my career, I’ve developed a personal framework I call The CIRCLE Audit. I use it periodically — not as a paranoia-fueled exercise in suspicion, but as a deliberate, structured act of leadership self-care. If you’re going to choose your circle wisely, you need a tool for actually doing the work. This is mine. I’m sharing it with you.

Letter	Dimension	What It Looks Like When Present	What It Looks Like When Missing
C	Candor	They told you before your presentation that slide 4 was confusing, not after the meeting fell apart.	They only validate. Every idea you share is “amazing.” Silence when you need honesty.
I	Investment	They make introductions without being asked. They remember your goals and follow up. They show up.	The relationship only flows one direction. You pour; they receive. There is no return.
R	Reciprocity	They call to check on you — not because they need something, but because they care about you as a person.	They are consistently available when they need something from you and consistently hard to reach otherwise.
C	Competence	They have experience, expertise, or perspective in areas where you are still growing. They elevate the conversation.	Their advice never challenges you. They reflect your own thinking back at you in slightly different packaging.
L	Loyalty Under Fire	When your name came up in a difficult conversation, they defended you. Not blindly — truthfully.	You only know they were in the room because someone else told you. Their silence permitted the narrative.
E	Evolution	They are actively growing — reading, learning, expanding their thinking. Their energy pulls you forward.	They subtly resist your growth. New ambitions make them uncomfortable. They celebrate when you plateau.

Run this audit honestly. Not harshly — but honestly. You may find that your circle passes with flying colors, and that realization itself is a gift worth sitting with. Or you may find gaps you’ve been avoiding naming. That’s not a crisis. That’s information. And information is the first step toward change.

How to Audit Your Circle Right Now: Six Practical Tests

Frameworks are only useful when they translate into action. Here are six tests you can run this week — not eventually, not when things calm down, but this week — to get an honest read on the composition of your circle of influence:

1. The “Who Do I Call?” Test

When something goes seriously wrong — not minor inconvenience, but genuinely wrong — who are the first three people you call? Not who you should call, but who you actually pick up the phone and dial. Those three people tell you almost everything about your circle. Are they builders? Are they equipped to help? Do they make you feel steadier after the conversation, or more rattled? The speed and instinct of that choice reveals your deepest trust patterns.

2. The Honesty Test

Think of your last significant mistake or consequential bad decision. Now ask yourself: did anyone in your circle tell you — before it happened — that you were heading in the wrong direction? If the answer is yes, that person is invaluable. Protect the relationship. If the answer is no, ask a harder follow-up: were the signals there, and your circle stayed quiet? Or did your circle genuinely not see what was coming? Both answers matter, but they call for very different responses.

3. The Energy Audit

After you spend time with each key person in your circle — whether it’s dinner, a call, a meeting — pay attention to how you feel when it’s over. Do you feel energized, clear, and expanded? Or do you feel drained, vaguely unsettled, and smaller? Your body keeps score long before your mind admits what it knows. Energy is data. Use it.

4. The Celebration Test

Share good news with the people in your circle — a promotion, an opportunity, a creative breakthrough — and watch carefully. Who genuinely lights up? Who mirrors your joy with spontaneous, unrehearsed delight? And who subtly changes the subject, immediately introduces a complication, or pivots to their own news within thirty seconds? Authentic celebration is one of the clearest windows into genuine investment. You can’t fake it convincingly for long.

5. The Absence Test

This is the hardest one, and also the most revealing. When you are not in the room, who is protecting your name? When a conversation turns to your work, your decision, or your reputation, who is the person who says “That’s not who I know Laurent to be — let me offer some context”? And conversely, who is the person quietly participating in a narrative about you that they would never repeat to your face? You may not be able to answer this question with certainty. But you often know more than you’re allowing yourself to know. Trust that.

6. The Growth Mirror

Look at the five to seven people you spend the most time with. Where are they in their own journey — professionally, personally, intellectually? Are they operating at the level you’re aspiring to reach, or are they comfortable at a level you’ve already surpassed? This is not an invitation to abandon people you love. It is an invitation to be honest about whether your circle is pulling you forward or anchoring you in comfort. You can love someone and still recognize that their season in your inner circle may be complete.

Building a Circle Worth Having

I’ve spent considerable space in this article on what to watch for and what to audit. But I want to end this section on something more important: the extraordinary, transformative power of a circle that is genuinely aligned with who you are and where you’re going. Because when you get it right — when you build a circle of real builders — the acceleration you experience is unlike anything you will encounter alone.

Here is what a powerful, aligned leadership inner circle actually looks like in practice:

The mentor who has been where you’re going. Not someone who gives advice from theory, but someone who has navigated the terrain — the organizational politics, the loneliness of senior leadership, the moments when the right decision is also the hardest one. I have been blessed with mentors like this throughout my career, and I do not take that for granted for a single day. Find them. Learn from them. And when your time comes, become one.
The peer who challenges your thinking without competing with your spirit. This is a rare and beautiful thing: a colleague at your level who pushes back on your ideas with rigor, who disagrees without dismissing, who makes you sharper without making you smaller. When you find this person, hold on.
The advisor who brings expertise you don’t have. None of us can be expert in everything. The most effective leaders I’ve observed are deeply comfortable surrounding themselves with people who know more than they do in specific domains. Ego is the enemy of this kind of circle-building. Humility is its foundation.
The truth-teller who loves you enough to say the hard thing. This person will occasionally make you uncomfortable. They will say the thing everyone else is thinking and no one else will voice. They are a gift — even when it doesn’t feel that way in the moment. Especially when it doesn’t feel that way in the moment.
The visionary who sees more in you than you see in yourself. Every leader needs at least one person in their circle who holds a larger vision of their potential — someone who calls you forward when you’ve talked yourself into playing small. In my own journey, from Brooklyn to Haiti to Howard University to the frontlines of technical support to SVP of Global Customer Support, there have been people who believed in a version of me I hadn’t yet grown into. Their belief was architecture. It helped me build something real.

A Note to Leaders of Color and First-Generation Professionals

I want to speak directly to you for a moment — because I see you, and I know that the circle challenge I’ve been describing carries additional weight when you’re navigating it as a first-generation professional, as an immigrant, or as a person of color in corporate spaces that were not originally designed with you in mind.

I grew up in Brooklyn and Haiti. I attended Howard University. I entered corporate America as a young Black man who had to learn the unwritten rules of the game in real time, without a manual and often without a mentor who looked like me. I know what it feels like to be so grateful for any table that offers you a seat that you don’t stop to ask whether the people at the table actually want you to succeed. I know what it feels like to hold on to a relationship that isn’t serving you simply because the alternative — being without that connection entirely — feels more dangerous.

Here is what I want you to hear: the margin for error in your journey may feel narrower, but your standards cannot be lower. In fact, they need to be higher — not because you deserve less grace, but because the stakes of getting your circle wrong are more immediate for you. You may not have the family connections, the inherited professional networks, or the safety nets that cushion certain errors for others. That means the people you let close to you matter more, not less.

It is harder to find mentors and advisors for leaders who look like you, who understand the specific texture of your experience, who can see both the systemic realities and the personal possibilities without one erasing the other. But they exist. I promise you they exist. And you deserve to be intentional about finding them rather than settling for proximity with people who don’t actually have your best interests at heart.

Be warm. Be generous. Be open to people who don’t look like you and don’t share your background — some of my most important mentors and allies have been people whose life experiences looked nothing like mine. But be discerning. Protect your vulnerabilities with care. Share your deepest ambitions with people who have earned that trust through demonstrated investment in your growth. And never mistake someone else’s comfort with your limitations for investment in your potential.

For the First-Generation Leader

You did not come this far — navigating systems not designed for you, building credibility in rooms that questioned your presence, finding your voice in cultures that sometimes tried to silence it — to hand the keys of your trajectory to people who are not invested in where you’re going. Your circle is one of the few things in this journey you actually get to choose. Choose with intention.

Choose Wisely. Your Destiny Depends On It.

I started this article with a personal story — a moment of betrayal, quiet and slow, by someone I had trusted. I want to end it with something different: a declaration of possibility. Because everything I’ve shared here — the cautionary tales, the framework, the audit tests — is ultimately in service of something hopeful. The right circle doesn’t just protect you from what could go wrong. It accelerates everything that can go right.

Your standards will rise to meet the people you spend time with. Your decisions will be shaped by the questions those people ask of you — or don’t. Your destiny — the thing you are building, the leader you are becoming, the legacy you will leave — will bear the fingerprints of the people you chose to let close. This is not metaphor. It is mechanics. It is how human beings actually work.

So I ask you, as directly and as warmly as I know how: Look at your circle. Really look at it. Not the circle you have on paper, or the one that looks impressive in a LinkedIn post, but the actual living circle of people who have access to your thoughts, your fears, your ambitions, and your vulnerabilities. Are they Builders? Are they asking hard questions? Are they growing? Are they loyal under fire? Are they telling you the truth?

If the answer is yes — celebrate that. Invest in those relationships with everything you have. If the answer is complicated — that’s okay too. Complicated is where growth begins. Start there. Be honest there. Make deliberate choices there.

“Your circle shapes your standards. Your standards shape your decisions. Your decisions shape your destiny. Choose wisely.” — Laurent Pierre, Jr., SVP of Global Customer Support, Precisely | Author, The Unfinished Work

The people around you are not incidental to your journey. They are inseparable from it. And you — right now, today — have the awareness, the agency, and the responsibility to choose them with the same intentionality you bring to every other consequential decision in your life.

Choose wisely. I’m rooting for you.

Continue the Conversation

If this article resonated with you, here’s how we go deeper together:

• Reflect honestly on your own circle using the CIRCLE Audit framework above. It will surface truths you may have been avoiding — and clarity you have been searching for.

• Share this article with someone in your network who is navigating a leadership transition, a career pivot, or a moment of questioning who belongs in their inner circle. Sometimes the most powerful thing you can do for someone you care about is hand them the right words at the right time.

• Subscribe to The Future Ready Leader at laurentpierrejr.com — where every article is designed to give you practical frameworks rooted in real executive experience, honest enough to challenge you and human enough to sustain you.

• Connect with me on LinkedIn — I read every message, and I mean that. If something in this article sparked a question or a story of your own, bring it. That is exactly the kind of conversation I built this platform for.

• Explore my book, The Unfinished Work: Redefining Leadership for the Modern Technology Era — a deeper exploration of the leadership principles I’ve built across 30+ years at the intersection of people, technology, and organizational transformation.

Topics Explored in This Article

About Laurent Pierre, Jr.

Laurent Pierre, Jr. is a global technology executive with more than 30 years of leadership experience at IBM, Microsoft, NielsenIQ, and Precisely, where he currently serves as Senior Vice President of Global Customer Support. Born in Brooklyn and raised in Haiti, Laurent attended Howard University and built his career from frontline technical support to senior executive leadership — a journey shaped by relentless curiosity, people-first values, and a belief that metrics matter, but people matter more. He is the author of The Unfinished Work: Redefining Leadership for the Modern Technology Era and the founder of The Future Ready Leader blog at laurentpierrejr.com.

References & Sources

Strauss, Barry. “Julius Caesar’s Forgotten Assassin.” HISTORY.com, A&E Television Networks, March 15, 2018. [Decimus Brutus / Caesar assassination.]
Cassius Dio. Roman History (Historia Romana), Book XLIV. [Primary ancient source on Caesar and Decimus Brutus.]
“Enron Scandal.” Wikipedia / CEO Today. [Bankruptcy filing December 2, 2001; $63.4 billion in assets; 20,000 employees; Arthur Andersen dissolution.]
Watkins, Sherron. Internal Memorandum to Kenneth Lay. Enron Corporation, August 2001. [Direct warning of accounting scandal implosion; reproduced in Congressional testimony.]
U.S. Department of Justice. United States v. Jeffrey K. Skilling. Skilling conviction; original sentence 24 years federal prison, later reduced. [Enron fraud case.]
Stratrix Strategic Forks. “WeWork: A Case Study in Governance Failure.” March 16, 2026. [WeWork valuation collapse, SoftBank $10.6B investment, bankruptcy 2023.]
Galloway, Scott. Commentary on WeWork S-1 IPO prospectus, 2019. [Quote regarding misrepresentation in WeWork filing; widely attributed and cited in business press.]
Shadrake, David. “Theranos Postmortem: Governance, Deception, and the Board That Asked No Questions.” [Board composition analysis; Tyler Shultz whistleblower account; $700M investor losses.]
Global Link Law. “Theranos Corporate Governance Analysis: A Cautionary Study.” [No audit committee; no technical oversight; board meeting frequency and information asymmetry.]
U.S. Department of Justice. United States v. Elizabeth Holmes. Holmes convicted January 2022 on four counts of wire fraud and conspiracy; sentenced to 11.25 years federal prison, November 2022.