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Human Beings are Messy Data Sets
This is one of the reasons alignment is so difficult, whether in families, teams, businesses, or entire organizations. Systems are relatively straightforward. A process follows a sequence. A policy establishes boundaries. A workflow defines how something should move from one stage to the next. If something goes wrong, you can often trace the breakdown, identify…
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Conversion of Knowledge of Acquaintance into Knowledge About Is a Risky Exercise
My WHY, according to the WHY Institute, is Make Sense. When I first encountered the WHY.os framework, I remember feeling a strange sense of recognition. The WHY Institute describes a WHY as the fundamental motivation that drives a person’s behavior, decisions, and way of seeing the world. In their model, the WHY is expressed through…
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Is this Decision Asymmetrical?
Asking “Is this decision asymmetrical?” is a vital mental model for risk management and strategy. Before discussing strategy, before discussing execution, before discussing budgets, restructuring, hiring, expansion, partnerships, marketing campaigns, software purchases, or new opportunities, the question to ask is: Is this decision asymmetrical? Most leaders spend considerable time trying to determine whether a decision…
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The fog of war does not only exist on battlefields
The fog of war is a phrase that originally belonged to military strategy…those moments where commanders were forced to make decisions while visibility remained partial, communication fractured, and information arrived distorted through fear, delay, assumption, ego, or incomplete observation. From a distance, war often looks like movement directed by certainty. Inside it, however, people are…
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“More than physical pain, I fear humiliation…”
The title of today’s post is the line spoken by Duncan, the insecure CEO of an up-and-coming data-mining company called Hypergnosis, during a therapy session with Joanne in the AMC series Audacity. While the darkly comedic drama eventually reveals other fractures moving beneath his life…an unraveling marriage, unresolved father wounds, mounting emotional instability…the statement itself…
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Why “One Size Fits All” Decision Training Fails
There is value in teaching and training leaders to become more effective in areas like decision-making, communication, delegation, negotiation, strategic planning, conflict resolution, emotional regulation, and execution. Organizations need these things. Teams function better when leaders can slow down enough to evaluate options, regulate reactions, ask better questions, and avoid making decisions from pure panic…
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Clients buy for emotional relief, not technical accuracy
The consultant who sounds certain. The advisor who reduces complexity into one clean answer. The framework communicated with confidence. A polished implementation roadmap. When pressure is high and consequences feel immediate, clients are more than likely to gravitate toward the person who makes the discomfort stop fastest. A confident answer can feel like oxygen when…
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What Apollo 13 Understood about Leadership Under Pressure
“Houston, we have a problem” has survived all these years partly because of the way it was delivered. The sentence itself carried no drama. There was no attempt to inflate the moment emotionally even though an oxygen tank had exploded in space and three men were suddenly inside a situation that could very realistically kill…
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Don’t Volunteer yourself into Future Anxiety
In other words, don’t emotionally solve problems you think may occur in the future. We have all done this at one time or another. Something happens. We anticipate the problem. We immediately start solving. A problem becomes a prediction. What makes this difficult is that entrepreneurship does require anticipation. You cannot operate responsibly without thinking…

