Tag: Being a CEO

Thinking in Bets: insights on decision science from the 2018 book by Annie Duke

Life is poker, not chess.

We operate with limited information and are outcomes are heavily influenced by others with varied priorities. That’s the setup for the 2018 book Thinking in Bets by poker player Annie Duke. She was near to several poker scandals but has since focused on decision science — with her poker past as an effective storytelling device.

It was popular in business circles. The book is effective in conveying a clear overall point and synthesizing relevant research. I enjoyed it and would recommend it.

Below I share notes for my future reference.

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Me & White Supremacy: notes on the 2021 book by Layla Saad

Allyship is not an identity, but a lifelong process.

In twisted and complex American race relations, that amounts to a controversial stance. The last several years have been especially polarizing and yet somehow also clarifying and therefore productive.

For my work, myself and my community, I try to follow closely contributions to disentangling these systems. That’s why I picked up a copy of Me & White Supremacy, the 2021 book by Layla Saad. The book is structured as a kind of work book with journal prompts scheduled to run as a “28-day challenge.”

It also reads like an effective review of current recommendations on what Angela Davis famously called “anti-racism.” Whether you’re new to the conversation, or a professional that strives to keep engaged with the conversation, I recommend it. Below, I share my notes to review in the future.

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What question is your work answering?

A version of this essay was published as part of my monthly newsletter a couple weeks back. Find other archives and join here to get updates like this first.

Every company is an approach to answering some question. (Every nonprofit might be a policy failure.)

Many mistakes are made in choosing that question: it might be too ambitious, or too unambitious. It could be too niche, or not focused enough. The true addressable market might be too small. The question may not be a lasting one. You can ask a question too early or too late, with the wrong leadership, team or product. Some of that can be changed by a good team, so along the company-building journey, you must change your approach.

But don’t change the question.

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Little ways an organizational leader can show her team she cares about them as people

Pay them a competitive salary. Protect against mission and role creep. Give something clear to work toward and a strategy to employ to get there.

As an organizational leader, these are the foundations of developing a healthy relationship with your workforce. I’ve found there are other signs of an empathetic organizational culture that you can develop, without excessive budget needs.

These are examples of ways to show your team that you actually care about them as people. It goes a long way to develop the relationships you need to take on a big challenge, particularly without a pile of money.

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I changed a lot at my company. Here’s why beating a big Q1 revenue goal meant so much

A version of this essay was published as part of my monthly newsletter a couple weeks back. Find other archives and join here to get updates like this first.

Nobody wants to follow someone who made General in peacetime.

I’ve been thinking about that concept a lot lately (Ben Horowitz calls its Peace/War Time CEO). In 2017, after eight years of informally leading the tiny community journalism organization I cofounded, I named myself CEO. Up until that point, my cofounder Brian and I had survived together. We’d always find a way to last a bit longer, growing slowly and thoughtfully as we navigated treacherous waters.

That survival approach was rational for growing a local news company in the early 21st century,  a time in which consumers maintain very high expectations for free and independent journalism but have not yet been fully trained to actually pay or otherwise support its work in a post-advertising world.

But in early 2018, as I was finally feeling the great responsibility of the CEO title, I took stock of where my company was.

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To be great, you must know how to change speed

A version of this essay was published as part of my monthly newsletter a couple weeks back. Find other archives and join here to get updates like this first.

In high school, my varsity soccer coach would preach: Masters change speed.

The best players aren’t always the fastest. They are the ones who can go fast and then slow. Dribble the ball at a sprint. Stop. Pause. Redirect. Sprint again. Pace. Pace. Pace.

It’s among the lessons from my youth I reflect on most often. It carries through so much of my life. I love speed. It takes mastery to manage on deadline, something I surely learned from newsrooms. Yet, as I age, I’m most proud of how I can find moments of calm to slow down amid my frenetic pace.

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How to fund small projects as a CEO

One unexpected result of becoming CEO of my own company is that I found myself without a traditional budget line I could pull from.

As we grew our company, we created a budget aligned with core functions. I stepped into a role in which I was overseeing them all, but I didn’t set aside budget for me in last year’s budget for myself. That sparked me to wonder how other CEOs approached giving themselves budgetary space to experiment, explore and trial.

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