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Unpacking Your Life
Unpacking Your Life

Exploring the crossroads of life, security, and self.

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Unpacking Your Life

Exploring the crossroads of life, security, and self.

It’s Time to Come Clean to My Microsoft Family

Posted on July 6, 2026July 2, 2026 By UPL Admin

It is finally time to come clean to my Microsoft family. For the last five years, I have been living in two very different worlds. By day, I was a Senior Escalation Engineer at Microsoft, working in the support world, helping solve complex problems, jumping into the hard cases, and doing the kind of work most customers never see but absolutely depend on.

At the same time, I never stopped being the CIO of Centurion American Development Group. That may surprise some people, but it probably should not. Those who know me know I have never been wired to sit still, coast, or wait for someone to hand me permission to lead. I have always believed you prove what you can do by doing the work, carrying the weight, and delivering results when nobody is clapping.

That dual role gave me a very unique perspective. While doing my Microsoft job, I was also helping lead a real business organization with real budgets, real people, real expectations, real decisions, and real consequences. There was no corporate theater to hide behind. If something broke, it mattered. If a decision was bad, the business felt it. If people were unhappy, you heard about it quickly.

And here is the uncomfortable part. I was helping lead a larger organization than some of the people sitting in leadership roles above me. I was doing it with higher satisfaction, better communication, stronger quality results, and stricter budget discipline than what I was seeing from some areas of Microsoft leadership. That is not arrogance. That is observation.

Leadership does not have to be complicated. In fact, I think we have made it way too complicated. Somewhere along the way, people started confusing titles with leadership, meetings with communication, slogans with culture, and dashboards with reality. For me, leadership has always come down to the basics: treat people the way you would want to be treated, keep the lines of communication open, tell the truth, admit when something is broken, and listen before you dismiss.

Most importantly, remember that the people doing the work are human beings. They are not spreadsheet entries. They are not cost centers. They are not anonymous boxes on an org chart. It sounds simple because it is simple, but simple does not mean easy.

The fact that I could not even get a real meeting with people in parts of our leadership team told me everything I needed to know. Not because I thought I was owed something special or needed a red carpet, but because acknowledgment matters. Basic professional respect matters. Human beings matter.

You cannot preach culture while ignoring the people who helped build it. You cannot talk about growth mindset while refusing to listen. You cannot claim to care about employees while treating the relationship as purely transactional. And that is what Microsoft became for me when I rejoined five years ago. Transactional.

That word hurts to say because Microsoft was once more than that to me. It was a place where you could build a career, feel proud of the work, support customers at a high level, and believe the company had your back. It was not perfect. No company is. But there was something there. There was a mission. There was pride. There was a sense that the work mattered and the people mattered with it.

When I came back, I wanted to believe that was still true. It became clear pretty quickly that it was not. At least not in the same way. The support world has changed. The leadership around support has changed. But honestly, I do not think this is just a support problem. Support is just where I lived it.

What I saw there felt like a smaller version of what has happened across the broader company. Less connection. Less loyalty. Less humanity. More process. More politics. More distance between the people making decisions and the people living with the consequences.

That does not mean there are not amazing people still there. There absolutely are. Some of the smartest, hardest-working, most dedicated people I have ever known are still inside Microsoft. People who care deeply. People who still answer the phone. People who still take pride in fixing the impossible. People who quietly hold the whole thing together while leadership sends another email about values.

Those people are the reason this is hard. They are my Microsoft family. They are the ones I will miss. But taking the VRP was my signal that I am done. Not bitter. Not broken. Not defeated. Done.

I am done pretending the company is still what it was. I am done waiting for leadership to remember that people matter. I am done trying to get a conversation with people who should have been willing to listen in the first place. I am done giving more loyalty to a machine than the machine was willing to give back.

And oddly enough, I feel good. I know who I am. I know what I bring. I know how I lead. I know what real accountability looks like because I live it every day outside the Microsoft bubble.

At Centurion American, I get to lead. I get to build. I get to solve real problems with real people. I get to make decisions that matter and see the impact. I get to be part of something where the work is not hidden behind layers of corporate fog. That is where my energy belongs now.

So to my Microsoft family, thank you. Thank you for the late nights, the war rooms, the escalations, the laughs, the scars, the stories, and the lessons. Thank you to the people who still care. Thank you to the people who showed up when it mattered. Thank you to the engineers, support professionals, and teammates who made the hard days worth it.

To some in management, I will simply say this: do a reality check. Leadership is not a title. It is not a level. It is not a badge. It is not how many people are under you in the org chart.

Leadership is how people feel after they interact with you. It is whether they trust you. It is whether they believe you will tell them the truth. It is whether they feel seen, heard, and respected. It is whether your people would still follow you if they did not have to.

That is the test. And far too many are failing it.

Microsoft gave me a lot over the years. It gave me opportunity, experience, friendships, and stories I will carry forever. But it also gave me clarity. The company changed. I changed too.

Now it is time to take everything I learned, everything I survived, and everything I know I can do, and put it into the next chapter. This is not the end of my story. It is me finally writing it on my own terms.

General Management Mental Health FreedomMental Health

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