Week 41, 2022—Issue #225

Paradoxical Leadership: Long and Short, Sustain and Disrupt, and Confident and Humble

Andreas Holmer
WorkMatters
Published in
3 min readJan 4, 2023

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Each week: three ideas to help us build better organizations. This week: three ideas for better leadership. This post was originally published in the WorkMatters newsletter on Oct 14, 2022.

Photo by Christina @ wocintechchat.com on Unsplash

I’ve spent the last few weeks exploring NZS Capital’s whitepaper on complexity investing. That’s done. But I’ve kept thinking about complexity and how it affects leadership.

Turns out there are a few paradoxes to deal with:

1. Long and Short

Leaders must think long-term while dealing with the here and now.

Unexpected events are surprisingly common. Try as we might, we simply can’t know what the future holds. That’s why we should focus on what will not change. When we double down on First Principles, we are less likely to be led astray by quarterly targets, etcetera. As Jeff Bezos has said: “In the long term, there is never any misalignment between customer interests and shareholder interests.

2. Sustain and Disrupt

Leaders must optimize for efficiency while placing bets for the future.

The pace of change is steadily increasing. Economic cycles come and go, as do technological paradigms. That’s why we should work to both sustain and disrupt our businesses. Explains Johns and Slingerlend in their whitepaper: “This represents an important aspect of combining Resilience (steady S-curve) with Optionality (adding a new S-curve) — the ability to adapt and evolve.

3. Confident and Humble

Leaders must act confidently while remaining humble about the future.

We’re inundated with information. The trick is to separate signal from noise. That’s why we should create time and space for mindful decisions. It’s the only way we can build confidence in incremental action while remaining humble in terms of future events. Explains Adam Grant on Twitter: “Confident humility is knowing how little you know and how much you’re capable of learning.

F. Scott Fitzgerald famously wrote that “the test of a first-rate intelligence is the ability to hold two opposing ideas in mind…and still retain the ability to function.

This is certainly true for the modern leader.

Explains Gary Hamel and Michele Zanini in Humanocracy:

Scientists who embrace the conflict between opposing theoretical frameworks have the chance to discover new and deeper truths. Jurists (and parents) that navigate adroitly between mercy and justice are more humane and effective. Political systems that resist ideological fractures are better at crafting effective policies. Mastering paradox is equally vital for our organizations.

Paradoxical Leadership is the ability to reframe one’s thinking about contradictions from ‘either/or’ to ‘both/and’. It’s an essential leadership quality in this volatile, uncertain, complex, and ambiguous world in which we now live.

That’s all for this week.
Until next time: Make it matter.

How can we build better organizations? That’s the question I’ve been trying to answer for the past 10 years. Each week, I share some of what I’ve learned in a weekly newsletter called WorkMatters. Subscription is free. Back-issues are published to Medium after three months.

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Andreas Holmer
WorkMatters

Designer, reader, writer. Sensemaker. Management thinker. CEO at MAQE — a digital consulting firm in Bangkok, Thailand.