Reader,

So, why should I write another book?

TJ posed that question and not-so-subtly challenged me with “Sure, you’re kind of smart, but as an old dude your knowledge is out of date. After all, The Prepared Mind of a Leader was published twenty years ago.”

2006

The point of the 2006 book was to examine the skills leaders needed to be better prepared for a changing world. Is 2026 really that different from 2006? Maybe not, but I think leaders at all levels are being challenged in new ways.

Leadership in 2006 was hard but the world was relatively understandable.

• Problems stayed stable long enough to analyze. Most big businesses worked on an annual planning cycle.
• Decisions unfolded on human timelines. Sure, we used computers to summarize and analyze data, but we marched at “human speed.”
• Experience mattered. Twenty years of experience really was important.
• Expertise accumulated. The career ladder was there to take people from individual contributors to managers to executives.
• And if something failed you could usually diagnose it, fix it, and move on. And, if not, some hotshot consultant could tell you what to do.

However, that world no longer exists and leaders need to modify their “thinking system.”

Leaders are not struggling because they lack intelligence, effort, or discipline. They are struggling because the environment itself has changed and some (but not all) leadership thinking has not.

Today’s world is not just faster or more complex, it’s wicked. (Wicked is being used as a systems descriptor, not a morality label.)

What Makes 2026 Different?

A wicked world behaves in ways traditional leadership training was not designed for:

• Problems change as you try to solve them. For example, we’ve been dealing with “the drug problem” since the 1970s. Was President Nixon’s war on drugs approach applicable to President Trump’s narco-terrorism? Both deal with drug problems in America.
• Stakeholders disagree on what is even happening. Are AI data centers good or bad for a city? Is AI a productivity panacea or the death knell of entry level jobs?
• Actions trigger consequences far from where they were taken. How might a TikTok “influencer” in Brazil impact your marketing campaign?
• Feedback arrives late, distorted, or politicized. So, what do you think of the recent Melania documentary? Might the answer depend on your political views?
• Small decisions can create permanent effects. We’re still watching the impact of letting our preteens have a phone. Is it a safety device or a tether?
• Expertise ages faster than careers. How about the deep expertise needed to develop on-site data centers in the era of Amazon Web Services? Will programmers be needed in the age of AI agents?

It’s a different operating environment today, and smart leaders are getting surprised. Why? Well, many leadership tools still assume three things:

1. Problems can be clearly defined.
2. Options can be compared objectively.
3. Outcomes can be predicted with reasonable confidence.

However, in a wicked world with lots of tight interactions, none of these assumptions hold.

1. The problem is provisional.
2. The options reshape the system itself.
3. The outcomes depend on responses you cannot fully anticipate.

That is why smart, experienced leaders can make decisions that seem right, but they fail.

Why? Because the system moved while they were deciding.

AI – a New Leadership Risk

Artificial intelligence has collapsed our sense of time. Prompt ChatGPT and you get a response (answer?) as soon as you hit the return key.

Decisions that once unfolded over weeks now propagate in hours and consequences lock in before learning arrives.

Unfortunately, you cannot pause this system to think longer and deeper.

• Delay is no longer neutral. We’re afraid that others will think we’re waffling.
• Inaction is no longer safe. The system is tightly coupled and will change while we think.

I contend that we need to upgrade our leadership thinking systems to respond to some fundamental shifts in how this world is run.

I know we cannot control complexity. However, I think we can improve the skills needed to operate intelligently within it.

Back to TJ’s challenge regarding old-dude-thinking, next week’s letter will review the late Russ Ackoff’s challenge to “formulate the mess.” Some old thinking certainly applies to today.

Oh, by the way, the tentative title for the new book is A Thinking System for a Wicked World.

Cheers,

Bill