What My Family's Estate Trust Project Has Taught Me About Humility

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Over the past 20 months, I have served as appointed trustee for my parent’s estate trust. On paper, that sounds like an administrative role. In practice, it has been one of the most demanding projects I have ever managed, and it came my way with no project plan or scope document, no set budget, and key sponsors who are my own siblings.

Most of the project work moved forward the way estate trust work typically goes based on the size and complexity of our parents estate.   One core issue did not. Figuring out how to ethically and fairly distribute the estate’s personal property among five heirs became the stickiest problem of the entire project. In fact, because of lack of agreement among the five beneficiaries on this phase, it resulted in a two-to-three-month delay in our project timeline.  One of my brothers could not change his mindset around what ‘equality’ meant as he fixated on the original trust document language.  He believed that literally every single piece of personal property from an unopened pen set to the piano needed to be accounted for monetarily as well as be divided exactly into 5 equal shares. 

So of course, he pushed for a comprehensive inventory that could have taken many months and additional expense to the trust for a comprehensive accounting.  For myself as trustee, I did not believe this was feasible or even reasonable.  Certainly, from a legal perspective, this was not required.  On top of that, the other beneficiaries decided to join him to insist this be accomplished.  Thank goodness we had previously secured outside legal counsel that helped mediate a reasonable solution that we jointly put together.  

I will be honest with you. My first temptation as trustee was to manage this situation unitarily based on what local law allowed.   I had the designated power as ‘executor’ to do so.  I had my own opinions about what was 'fair' but also reasonable to keep the project moving forward without further delay or additional expense.   My break came from one of my most ardent opponents on the matter, another brother from out of state.  This brother offered to come out to the trust property location to help establish a few private estate sales as a practical solution for property distribution. 

I made a deliberate choice to double down on expressing humility in agreeing to his proposal that was accepted by all the other beneficiaries.  It was the right move to make as we were able to solve what to do with the non-inherited personal property.  Also, I was able to negotiate a final agreement that allocated a greater portion of personal property assets to the two brothers out of state.  In this regard, I continued to stay humble enough to agree as a way to close out that phase of the project.  It allowed me to insist on a tradeoff to receive additional payment as trustee for hours worked above the flat rate for my service time that was previously agreed upon.    

Many of us carry an image of humility that makes it sound like being soft with others. We picture the person who never speaks up, who defers on every decision, who shrinks so others can feel large. That is not humility.

Stephen M.R. Covey offers a definition in The Speed of Trust that has stayed with me since reading the first time. He places humility inside integrity, and he describes the humble person as someone more concerned with what is right than with being right. I find that distinction clarifying. Humility does not ask us to abandon our convictions. Jim Collins found something similar when he studied companies that made the leap from good to great. In Good to Great, he describes the leaders at the top of those organizations as a blend of deep personal humility and intense professional will. They were ambitious, but their ambition was for the organization and its people rather than for themselves. When things went well, they looked out the window to credit others. When things went poorly, they looked in the mirror at themselves.

Robert Greenleaf would recognize both descriptions. His test for the servant leader was never about the leader's stature. He asked whether those served grow as persons, and whether they become healthier, wiser, freer, more autonomous, and more likely themselves to become servants. Humility is what makes that test possible to pass.

Here is the reality for most of us in project management. We are accountable for outcomes, yet we rarely have formal authority over the people who deliver them on the project team. Our engineers report to someone else. Our sponsor outranks us in the organization hierarchy. Our subject matter experts know far more than we do about their technical part of the work.

My estate trust project was that reality in miniature. As trustee, I do hold formal legal authority, and I learned that it was the least useful tool in my influence tool bag. Every sibling has a legitimate legal stake in the trust, a different perception and mindset and a voice that deserved to be heard. The same is true of every stakeholder on our projects. A stakeholder who feels unheard does not stop having concerns. Those concerns simply go underground and surface later as resistance, delays, or quiet disengagement.

We can think of the metaphorical analogy of a conductor in front of an orchestra. The conductor is the only person on stage who makes no sound. Every note the audience hears comes from someone else. The conductor's job is to listen more closely than anyone in the hall and to help each musician play their part at the right moment. When project leaders adopt that posture, the team plays better music, and the applause is a result of an outstanding performance of aligned musicians performing together based on a shared purpose.

I would like to be concrete here, because humility is easy to praise and harder to practice. On the estate trust project to date, it has showed up in three ways.

First, I asked open ended questions of my fellow beneficiaries before I proposed or made key decisions that impacted the trust. We met in many beneficiary meetings in which I listened to their concerns, questions and proposals. 

Second, I let the shared process carry the fairness instead of my own judgment. Transparency took the weight off my opinion and placed it on a shared method that everyone could examine and question.

Third, I admitted what I did not know and where I had gotten it wrong.

We are not completely finished. We have a final 2026 tax liability to be processed with our estate CPA and then a final beneficiary share distribution in early 2027.  The past few months, we moved from guarding positions regarding personal property to solving a shared problem, and I believe humility is the reason.

Edgar Schein, the MIT organizational psychologist, devoted much of his later career to this exact skill. In Humble Inquiry, he defines it as "the fine art of drawing someone out, of asking questions to which you do not already know the answer, of building a relationship based on curiosity and interest in the other person."

Notice the phrase "to which you do not already know the answer." Many of us ask questions in meetings that are really statements wearing a question mark. Schein invites us to ask the kind of question that could actually change our minds about what decisions to make for our projects.

Here are two actions to practice over the next two weeks.

1.     Ask one genuinely humble question in every key meeting. Before your next steering committee sponsor check-in, status meeting, or one-on-one, write down a single question you do not know the answer to, such as "What concerns you most about this phase that we have not talked about yet?" Ask it, and then stay quiet long enough to hear the full answer. Notice what you learn that a status report would never have told you.

2.     Practice the window and the mirror. Each time a milestone lands well, name a specific person who made it possible, out loud and in front of others. Each time something slips, begin your explanation with your own part in it.

Humility will rarely be the loudest attribute with people on a project team, and that is exactly why it is so easy to overlook. Over the long term, it is the strength that keeps people talking when the stakes are high, keeps information flowing when the news is bad, and grows the leaders around us because it leaves them room to lead. I learned that lesson again regarding my parents’ personal property distribution decision, and I believe it holds true on every project we will ever lead. You can do this!

I would love to hear from you this week. Reply to this email and tell me about a time humility, either yours or someone else's, turned a difficult conversation around or made a big difference in a project you managed. I read every response, and with your permission I may share a few anonymously in a future issue.

Serve well, lead well, and grow the leaders around you.