Tuesday Thoughts | 28 October 2025 | Issue 199 - Please Feel Free to Disagree

The past couple of weeks have found me wandering across North America, making a stop in Chicago for the DRI | Association of Lawyers Defending Business Leadership Conference and Annual Meeting, before heading further West for the CSAE Annual Conference.

When I was a much younger professional, these sorts of events were the source of copious notes, and too many take aways to possibly revisit; but as I get further into my career, the true value of these sorts of gatherings is in making and maintaining the connections that help me puzzle through the more complex aspects of my job (and life).

These days, a successful conference is when a clear theme emerges, that leaves me thinking critically about a focused area for improvement; this year, the theme that emerged was the power of respectful and constructive disagreement.

Being disagreeable, asking divergent questions, challenging the status quo, and doing things that are necessary but unpopular takes a great degree of bravery; but it is critically necessary for ensuring that the best answer, and not just the first or most obvious answer, are surfaced within any meeting, brainstorming session, or even a (not so) casual conversation among friends.

Learning to disagree, and remain cordial, and then go on to work collaboratively together, is a core skill, that I work hard to nurture; not to be argumentative, but because I know instinctively, that when a complex issue arises, chances are if we’re all agreeing early in the process of solving the puzzle, we are missing a critical piece.

Two weeks ago, the DRI Annual Meeting kicked off with a keynote from renowned reporter Bob Woodward, who recounted his first indication that something about the Watergate building break in was out of sorts – he had never seen such well dressed men accused of this sort of crime.

An entire chapter of history rests on the early notion that something was not simply as it seemed, and one man’s willingness to dig beyond the first and most obvious answer. Not to mention the willingness to hold someone with significantly more power – the President of the United States – to account for their actions.

Much later in the week, I had the chance to sit down with my fellow Executive Directors from all around North America, in a brilliantly planned session, we got to role-play difficult situations Executive Directors face regularly; again, we often disagreed about the path we might take to redress these issues, but each time those alternative perspectives and approaches taught me something.

Last week here in Victoria – yes, I am still on the West Coast, at least until tomorrow – I attended the CSAE Conference where sessions ranging from tapping into creativity, to surfacing our collective creativity, to learning to love your problems, kept resurfacing the idea that a healthy degree of friction is a key ingredient in collaboration.

Often, especially when Boards of Directors are involved, there is a tendency to want to come to an agreement as quickly as possible, as a sign that the board is working as a team; I would submit that the best teams are those that can spar with each other, and still come together to face a common adversary.

I don’t want to hurt anyone’s feelings either, but sometimes the kindest thing we can do is tell the truth, gently.

Have you ever disagreed with something I have written in Tuesday Thoughts? This is issue 199, and to be honest there are some past issues that I’m not sure I agree with anymore. Even when you didn’t buy into my hypothesis, I hope that the exercise of considering my perspective sparked something that led to your taking some sort of action.

This week’s call to action, is to be unafraid to disagree – kindly.

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I am a Certified Association Executive with over a dozen years of experience in leadership positions across Canada’s Not-for-Profit Sector, with deep ties in the Meetings and Events Industry. I use the art of storytelling in speech and writing to explain ideas, and to inform audiences and readers on a variety of topics. Learn more about how we can collaborate;

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