Lessons From a Year of Missteps, Messy Meetings and Better Decisions

As the year comes to an end, I have been thinking about the chaos of boardrooms, executive meetings and the occasional self-inflicted mess. I do not always navigate it well, far from it, but over time I have realised there are a few simple sayings that make sense of things when I look back on what happened.

This has been a year of lessons; some learned the easy way and others learned the uncomfortable way. I have said the right thing at the right time, and I have also said the wrong thing at exactly the wrong time. There have been moments of clarity, and moments where I have misread the room or let frustration get ahead of judgment.

The sayings below are not badges of wisdom; they are reminders. And I need them as much as anyone.

Before I share them, it is worth reflecting on how I try to work with boards – and why I do not always get it right.

How I Try to Work With Boards – and Why I Do Not Always Get It Right

Working well with boards is always a balancing act: honesty with respect, challenge with partnership, and independence with collaboration. The aim is to create an environment where issues are raised early, different perspectives are encouraged, and decisions can be made without ego taking centre stage. Clear, calm communication helps, especially when conversations are uncomfortable, as does listening closely, separating facts from emotion, and making space for disagreement without letting it become personal.

And it does not always go to plan. No one gets it right every time. There are moments of pushing too hard, or not hard enough; responding too quickly, or too cautiously; letting frustration show; assuming clarity where there was none; asking one question too few, or one too many.

The goal, always, is progress, not perfection.

What I know for certain is this: the quality of a board is rarely about its structure and almost always about the behaviours of the people around the table.

There is also a limit to what any board can achieve when some directors do not pull their weight or when others behave as if they are part of the executive team. Directors who engage deeply, prepare properly and contribute constructively make an enormous difference; those who merely turn up or slide into operational decision-making undermine the effectiveness of everyone around them.

Boards work best when every director understands their role – and stays in it. And that is why these sayings sit in the back of my mind, even if I do not think about them at the time.

1. “I do not know.”

These might be the most powerful words in leadership, and the most underused. Saying “I do not know” signals honesty, self-awareness and the discipline to avoid bluffing. Boards appreciate it. Executive teams respect it. People remember it. The important part, of course, is the follow-through: I do not know, but I will find out, and I will come back to you. Humility cuts through faster than false certainty.

2. Disagree without destroying the relationship.

Challenge ideas, not people. Boards and executive teams need healthy tension to make good decisions, but disagreement must never leave emotional debris. Separate the issue from the individual and remain open to being wrong. Rigid minds stop learning; curious minds evolve.

3. Management should be management. The board should be the board.

Boards that drift into operations demoralise management. Executives who try to manage the board undermine governance. When the boundary blurs, dysfunction enters; when it stays clear, organisations move faster, and talent thrives. Good boards ask the right questions. Good executives deliver the right answers.

4. Watch your unconscious bias.

Bias rarely announces itself. It appears in small moments, in a comment, a question or who you assume holds authority. I once had someone say to me, half-joking but clearly signalling a point, that they “were not as clever as me and not as good looking, but they were richer, implying that their wealth somehow made their view more valid. It was a perfect reminder of how easily status bias slips into decision-making. When you notice it, take responsibility: own it, apologise and do better.

5. Diversity is not a quota, it is a mindset.

True diversity is not achieved by adjusting the gender balance of a room. A homogenous workforce, of any type, creates blind spots. The real question is: What perspectives are missing? What lived experiences? What voices are not being heard? Diversity without inclusion is cosmetic; inclusion without genuine diversity is an echo chamber.

6. Being likeable is not essential, but it helps.

Effectiveness does not require universal popularity, but being approachable, fair and trustworthy makes difficult conversations easier and reputational hits less damaging. Technical skill gets you in the door; character keeps you there. When pressure arrives, and it always does, goodwill matters.

7. Tell me today and it is our problem. Tell me tomorrow and it is your problem. Tell me next week and you are the problem.

Problems rarely destroy organisations. Surprises do. Bring an issue early and we solve it together. Bring it late and you have removed my ability to help. Bring it very late and the issue is no longer the problem – your judgment is. Late disclosure is not a performance issue; it is a trust issue.

8. “Common sense is much less common than you think.”

Never assume the obvious is obvious or that others see what you see. Most governance failures I have witnessed were not caused by complexity, they were caused by the absence of basic, grounded thinking. Common sense is something leaders must model, not assume.

A Final Reflection

None of these sayings are clever, and none will win an award for originality. But they have survived market cycles, shifting expectations and every flavour of new leadership thinking for a reason: they remain true under pressure.

Boards will continue to deal with complexity, competing priorities, strong personalities and the occasional crisis. Executives will continue to juggle pace, politics, egos and imperfect information. And all of us, without, will get things wrong.

Leadership is not about being flawless. It is about being self-aware enough to notice the missteps, disciplined enough to correct them, and humble enough to learn from them.

The old line, “if it is not broken, do not fix it,” no longer holds. In today’s environment, someone is always trying to break your business, your model or your assumptions, competitors, technology, regulation or disruption itself. Better that you break it first.

If the coming year brings challenge, and it will, perhaps one or two of these sayings will make sense when you look back, as they so often do for me.

Because sometimes all it takes is a single sentence, remembered in hindsight, to change the way a conversation lands or a decision unfolds.

And at the end of the day, the most dangerous sentence you will ever hear in a boardroom is: “We have always done it this way.” And the most expensive mistake you will ever make is choosing an amateur when you needed a professional.

About the Author: Jon Brett

Jon Brett is a Non-Executive Director of Corporate Travel (CTM) and Raiz Invest (RZI).

Jon is also the author of the very successful  podcast series The Taking of Vocus, chronicling the extraordinary rise of Vocus, what went wrong with the M2 merger, and the eventual privatization of Vocus. The podcast is accessible via his LinkedIn profile Jon’s book The Taking of Vocus, is available on Kindle.

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