Tech leadership secrets unveiled at CTO Craft Con by legendary leader, Michael Lopp

At the November 2023 CTO Craft Con, we were joined on day 1 for an opening keynote presentation by the amazing Michael Lopp. Lopp is a veteran Silicon Valley-based engineering leader who has built both people and products at companies including Slack, Borland, Netscape, Palantir, Pinterest, and Apple. When he’s not deeply concerned with staying relevant, he writes about leadership, bridges, superheroes, and humans at the popular blog Rands in Repose. He currently works at Apple. 

Building culture is hard

Lopp kicked off the conference on day 1 with his presentation about Kobayashi Maru Management. His presentation aimed to cover:

  • How complex systems fail and why we let them fail
  • How you can prevent failure from occurring in the first place!

With leadership and engineering experience at giants including Slack and Apple, Lopp gave us an overview of his background and admitted, “Building culture (in start-ups) is incredibly hard. It’s exhausting.”

So, the audience waited in anticipation for an understanding of his solutions and suggestions.

Lopp continued with a quick poll with a show of hands and discovered that roughly 70% of the conference audience identified as introverts and 30% as extroverts. He added that at most leadership conferences he speaks at, this number is the same.

What is Kobayashi Maru Management?

Lopp created this management concept based on the Star Trek franchise’s philosophical idea of a “no-win scenario.” Lopp built on this during his presentation as he outlined the idea of a system failure in complex systems – a Kobayashi Maru event.

Michael Lopp

He said, “Complex systems are stable; it’s a built thing, knowable inputs, knowable outputsit’s working. A complex system is anything which involves a significant amount of human beings. All these feelings, all this knowledge, this complex thing called culture that we can feel but we can’t necessarily describe. All of this experience, all of these opinions. It’s like you’ve got a leash on a hurricane.”

3 steps to a Kobayashi Maru event

So, how does a Kobayashi Maru event occur in the first place? In summary, Lopp discussed the following:

1 The bad place

The Kobayashi Maru event is when there is a hint of impending disaster. And, a day in the life of a leader is full of unexpected developments which could lead to this (for example, a one-to-one meeting where someone resigns), Lopp added, “A Kobayashi Maru event begins innocuously.” and could be when a relatively simple decision is made but leads to something else. 

He gave the audience an example of when this happened to him in his career, how it started and what it became. For the full session, watch here.

Often a Kobayashi Maru event:

Michael Lopp
  • Is a complete surprise
  • Is an intensive, instant, adverse reaction to something
  • Is usually via a population of unexpected humans
  • Includes new critical information

Lopp discussed with our Community the consideration of who you will be or turn into when you fail. He added that a critical part of a leader’s job is their appropriate ability to act in unusually complete, unexpected and perhaps no-win scenarios.

He said such situations can be, “A virtual, unwingable scenario” and “A test of character.”

2 Don’t YOLO the comms

He added that you can’t afford to ‘wing’ the communication plan around an event, and he discussed how you can prepare in four steps. These steps included how to create a plan and ensure a successful execution of it. Lopp discussed how to communicate with all those affected by a change, how persons of interest should be involved, and what to do in an initial rollout plan.

For detailed information about this plan, you can purchase the presentation in full here.

3 What does winning look like?

Finally, Lopp discussed what the reward is for all this work. And it’s not quite what you might have expected it to be.

Find out what winning looks like in such events in the recorded presentation.

Michael Lopp

About Michael Lopp

Lopp has written three books. His first book “Managing Humans” now in its 4th edition, is a popular guide to the art of leadership and clearly explains that while you will be rewarded for what you build, your success is only because of your people. His second book, “The Software Developers Career Handbook,” is a career handbook for leaders and engineers alike. Michael’s third book, Small Things, Done Well, explains how focusing on the small parts of leadership is critical to becoming a better leader.

For fun, Lopp rides bikes (all of which have names), drinks red wine and tries to understand how forests work amongst the redwoods of Northern California because curiosity is how you grow.

Buy the full presentation and enjoy every minute of it.


Following two sell-out conferences in 2023, we’re proud to announce the launch of CTO Craft Con: London 2024, where we’ll relocate to the prestigious QEII venue, driven by the ever-increasing demand and growing number of attendees. 

Pre-registration is now open! You can sign up here to be the first in the know when Super Early Bird tickets go on sale.

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