Otis on Leadership

In Shawshank redemption Otis “Red” goes before the parole board with promises to be better. He tries to play by the rules and repeatedly gets denied. Finally, he has had enough and lets them have it. He is done with their game, they can keep him there forever.  He speaks with the tired wisdom of an old man desperate to speak sense to his younger self, bereft of the hope that a future is possible. He doesn’t care, and now they approve his release.

As amusing as this story is, I’m convinced it speaks to a deeper truth. The road to excellence in leadership doesn’t end with learning what to care about, but it definitely starts with a decision to follow your convictions over learning to do what others in power want.

When I was at DARPA, a PM’s goal was to get to the tech council and get the funding to make our idea happen. In several startups, I’ve marched a similar path to get funding. Each time, I had to navigate a maze of intermediaries, each wanting to hear specific things before I could get to the decision maker. The temptation was always present to win their approval by making my main focus to learn and deliver what they wanted to hear at the expense of my core vision. Keeping this temptation in check always helped in the end and I started to really know that conviction matters more than compliance.

Ok, that’s DARPA and startups. But most of my time has been in government and big companies. Big companies don’t just have intermediaries, they have systems, processes and whole organizations that test our compliance versus conviction trade. Conversations in every company start to change as everyone pays attention to where the winds are going. Conviction is still there, but it becomes bounded by what the boss or bosses emphasize. This is a natural consequence of what leadership means. We set the emphasis of our team and that includes culture and values. Shouldn’t we want our workforce to adopt what we are projecting?

Not at the expense of core individual convictions. To get a flavor of how this can lead us off the high road, a senior leader at a former company made (the fine topic of) female empowerment a core platform of his leadership and bombarded LinkedIn with his progress in this area at the expense of any other vision or message. I took pitches every day from vendors and vendor pitches started to include slides at the beginning that highlighted their commitment to female empowerment. This is how you end up with technology pitches that didn’t emphasize technology. While it was great that the boss was speaking his conviction, it was sad to watch the ecosystem around the company pander and step outside their prime value.

Tech vendor’s sometimes do this even when they focus on technology. When a topic becomes hot, say blockchain or machine learning, you start to hear lots of references to high concept phrases. Do you do X? Oh, yes we know X very well. Do you integrate with Y? oh yes. In my research work I get to bump into real thought leaders and it’s a completely different story. They question my question: “why would you do X?”. They often disagree with what I’m saying and point out my misunderstanding. I like these conversations. I like these people. They have different incentives, but they get my call back.

The best conversations are not banal agreements. Listen to a couple on their first date as they try to please each other. It’s funny watching them try and agree. It’s also a boring conversation.

Then watch the verbal tennis match of two long time friends disagreeing. “No, that’s not the best, this is . . . You’re crazy, this is . . .” In such disagreements there is life and learning and love. They deeply care about each other, but they aren’t focused on pleasing the other person. They have transitioned to something greater.

There just isn’t room for multiple things at the top of your priorities. If you focus on playing the game and optimizing the system to your advantage, you not only hurt your chances of success, but you risk any gains you make leaving you empty and not really adding up to any real change. On the other hand, if you really bottom out your convictions and decide what you really want to do, you have to take on the system. The system will fight you and may beat you down. The collective goals of that system will differ from yours and people will defend their equities in ways that give you headaches, sleepless nights and may even break you.

However, some people, and in the right culture, the right people, will watch. They will know that you care more about the impact of your principles than personal gain. They may not agree with you, but they will respect you. And when you succeed your success will have meaning and will take root. It may grow as others are inspired by your conviction and the truth of your principles.

One of my heroes, John Boyd, said you have to make a fundamental decision to the question: do you want to do something or do you want to be somebody? The magic of this is you really can have both, but you have to pick the right door. Both doors will lead to frustration. The choice to be somebody will make you an expert in what people want to hear and where the system is going. It will feed your ego with each win and teach you how to navigate a system with the right partnerships, the right things to do and the right things to believe. Each year you will risk becoming less and less of the person you once were, even if the organization rewards you.

The choice to do something driven by your convictions alone may pit you against the world. John Boyd never became a general. He never developed executive presence and took on the assignments that would get his name at the top of the promotion lists. He lived in a small apartment and his Facebook and LinkedIn page would have been boring and unnoticed. (Hint: I’m pretty sure he wouldn’t have one.) He did change the art of war and gave us our F-16, A-10, and built the science of aerial combat. He made a real impact on national security, but his lasting impact was on his acolytes who went on to change the Air Force and the DoD. His impact lives on.

The choice can’t be more clear. Integrity, conviction and meaning over advancement and ego. It’s Cincinnatus returning to his farm. It’s  General Marshall telling president Roosevelt that general Eisenhower was the better man to lead D-day. It’s George Washington refusing to be crowned King. It’s Socrates taking the cup of hemlock. It’s Martin Luther walking down the streets of Wittenberg with a piece of paper in his hand that will change the world.

The greatest parable is Solomon’s test for the two mothers who both claimed parentage of the same child: who cares more about the baby? When you truly care, you can’t lose. Without Solomon’s wisdom, the true mother would have suffered greatly. She wouldn’t have her baby to touch, to teach and to watch grow. But she could take great joy in the child’s life. There would be a chance for the truth to break free and make all things right.

Even if the other mother “won”, she would live a lie. It would be a parenthood devoid of meaning, filled with guilt and deception. Not living the lie is what bringing your full self means. It means being fully aware of the trades you will make, who you are and what you stand for.

This is all simple when described here, who wouldn’t choose the greater good when it’s described this way? But this gets complicated in Monday’s staff meeting or in your strategy review. Who will you be when you aren’t focused on the questions above? Every day you make decisions that together comprise a life. If you come to forks in the road and you haven’t been intentional about your principles and practiced applying them, then your path will be filled with extra obstacles to find meaning and you risk ending in a tale of sound and fury, in the end signifying nothing. That’s a heavy price to pay for the trophies you get from a happy system.







One response to “Otis on Leadership”

  1. Jim Martin Avatar
    Jim Martin

    Wow Tim. I came here to read your piece on Laser Alignment, but stayed long enough to come across this article. Thank you.

    I loved this particular statement… as it reminded me of how much I miss my wife (lost to cancer in 2017).

    “In such disagreements there is life and learning and love. They deeply care about each other, but they aren’t focused on pleasing the other person. They have transitioned to something greater.”

    Thank you for this.

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