Posts

The Myth of the Heroic Fix

“By failing to prepare, you are preparing to fail.” - Benjamin Franklin In startup and tech culture, we celebrate the last-minute save. But heroics are often symptoms of earlier neglect. Hero Culture thrives on moments like this: it's Friday at 4:47pm, a ticket has been sitting in review for two weeks, the stakeholder is impatient, and the engineer has a flight to catch, so someone pushes the deployment button because it's a small change and it's always fine. By 9pm there's a Slack thread, by 10pm it's a call, the engineer is somewhere over Ohio in airplane mode, and the one person who knows that part of the codebase is stepping outside a birthday dinner every fifteen minutes to check their phone. The fix takes forty minutes, the post-mortem takes two weeks, and the person who stayed up to save the night gets praised on Monday morning while the person who warned against Friday deployments three sprints ago is quietly forgotten. That's the thing about Hero Cult...

Visibility Bias in Leadership

“Only when the tide goes out do you discover who’s been swimming naked.” -  Warren Buffett One consistent truth I have observed in business is that leaders tend to reward what is visible, while some of the most essential work within organizations remains unseen. Consider a product launch. Slack channels fill with celebration, leadership offers public praise, and performance metrics are widely shared. Now contrast that with months of refactoring, quiet mentoring, and diligent risk mitigation that largely go unnoticed. Visibility distorts perception. This is visibility bias in action. It appears as: Shipping rewarded more than stabilizing. Roadmaps praised more than operational rigor. Deck-building valued over difficult conversations. Activity mistaken for impact. This connects directly to a post I previously wrote on shipping versus advancing , where I argued that organizations often conflate visible activity with meaningful progress. Shipping, with releases, tickets, a...

The Space Between Intention and Achievement

“You can't build a reputation on what you are going to do.” - Henry Ford Many years ago I told someone that my wife at the time and I were planning on adopting a child at some point in the future. To my dismay, the response was “congratulations!” As if I had already adopted a child. The person went on to say what good people we were. Receiving such praise did not feel gratifying. It felt misplaced. Almost like a “stolen valor” situation. After that I kept to myself our plans to adopt, and as it turned out the only child I ever adopted was my beloved step-daughter. The other day I wrote a blog post that I’d hesitated about quite a bit. It was regarding the DBA program at Edgewood University. On the one hand, I was excited to share a program that I’d found to be so affordable and complete, and from a good (albeit small) university. On the other, I dreaded the possibility of giving the appearance of one trying to take credit for what he has not yet done. There is an emotional tensio...

The Difference Between Shipping and Advancing

“ All change is not growth, as all movement is not forward .” — Ellen Glasgow One day I was at the neighbor's house, hanging out with friends, when I noticed a calendar with a quote for each month. Paging through it, I came across the one above. It impacted me deeply at the time, as it aligned with what I often felt I saw in the world. Movement without progress. As the years have passed the quote has stayed with me, and its meaning to me has evolved as I've progressed through my career. I can see that in today's business culture, we often confuse activity with achievement. Let's consider the differences between shipping and advancing. "Shipping" means delivering something, releasing a feature, completing a sprint, publishing a post, or closing a ticket. Shipping is visible. It feels productive. It checks a box. Advancing, on the other hand, means moving closer to a meaningful objective. It's creating durable value. Improving systems and not just outputs....

The Illusion of Control in Roadmaps

There we were, on a Zoom call, sharing our quarterly roadmap with leadership. The visuals were clean with dates, themes, milestones, and color coding. I think it's safe to say that the emotional effect of such a roadmap is a sense of alignment, clarity, and reduced anxiety. That's where there may be a problem. Roadmaps create psychological safety, but that safety can become an illusion of control.  Visual order reduces anxiety. We humans are social beings, and stories are core to our way of thinking about life. We prefer structured narratives over ambiguity. A roadmap, high level though it may be compared to a detailed project plan, turns uncertainty into a sequence. Having dates implies predictability, and sequencing implies causality.  Executives, for their part, want forward visibility. They want to see into the near- and mid-term future to the extent possible. Sales wants commitments that can be communicated and kept. Finance wants forecasting. Engineers look at the roadma...

Document Everything

Early in my career, I worked as a web producer at a startup, an experience I have written about before. It was a formative role that required wearing multiple hats and operating with a high degree of ownership. One of my primary responsibilities was receiving content from publishers and converting it into a format compatible with our online reader. The inputs varied widely. Investment newsletters arrived as emails, Word documents, PDFs, and in one case even by postal mail. Each format required a different workflow, and transforming them into publish-ready content demanded both technical adaptability and careful attention to detail. Although I could have managed most of the process from memory with minimal notes, I made a deliberate decision to fully document my work. I created step by step guides, including screenshots, and stored everything in Confluence. I also made sure my colleagues knew where to find it. My thinking was simple: if something unexpected happened, the business should...

Check Out Edgewood University's DBA Program

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For some time I've been thinking about my next academic move. While I have two Masters degrees, at some point in the future I'm going to want to complete a Doctorate in Business Administration. I've looked into a few options, but one from Edgewood University has stood out from the rest . Although it seems this program might be relatively new to the university, they have a great lineup of courses . And they are affordable, compared to other schools. You can complete your DBA for well under $25,000 according to what I've read.   Here are some quick facts about the school, via Wikipedia : Established: September 4, 1927 Religious affiliation: Catholic (Dominican) Endowment: $50 million President: Andrew P. Manion Academic staff: 150 Students: 2,469 (fall 2024) Undergraduates: 1,236 (fall 2024) Postgraduates : 1,233 (fall 2024) Location: Madison, Wisconsin Check out the video below and have a look at their website, if you're interested. I'm not saying this would d...