Crosby
Chief Outsmarticle Writer (COW)

I write outsmarticles in the spirit of coaching and sharing. I hope they help you outsmart a situation, or pass on wisdom in an article-sized format. Follow and find me on LinkedIn if you'd like to track me down IRL (over to the right).

Balance on the Wobble-Board: People, Product, Process

The principle here is simple: Balance your leadership contribution to the People, Product, and Process while keeping your eyes on the horizon. We are going to start this outsmarticle with a negative contrast. It drives home with clarity how simple this principle is, and how damaging it is to ignore. Consider a newly-promoted CTO. He is in his early thirties, …

How to Lead When You’re Not in Charge

Status: 2 chapters in.  Will make a great outsmarticle. Review forthcoming. Quick Summary: Ever noticed that great leaders do not always need the authority that they may or may not be given? Explore the endearing and enduring qualities of true leaders by examining them without their bureaucratic power. Identity, clarity, positivity, action… TBH I find the writing wordy, but worthy.

The First 90 Days

Status: I refer to this frequently, and gift it often. Invaluable resource. Quick Summary: Watkins makes a living helping people successfully do something we only do every few years; transition into a new role.  In here are all the insights and gems and pearls of wisdom that you might accumulate if you spent years studying thousands of transitions. A must read for any …

High Output Management

Status: Bookshelf pending re-read. (Last read over a decade ago.) Quick Summary: Must-read from the heady Silicon Valley startup days. Basically, stop wasting your time trying to be the Individual Contributor you once were (good at). Pay attention to setting up your team to win, by giving them the individual space, and building the right org and processes.

The Magic Candidate Quadrant: Domain or Product Expertise?

Ever applied for a Product Management role because you love the Domain, even if the Product needs are not quite a perfect fit? Ever sought to fill a role where you need robust Product Leadership, and don’t really care about Domain Expertise? Graphing Domain Expertise vs. Product Expertise helps clarify the needs for a given role, and conversely to understand …

Strategy, Structure, Staffing

Let’s face it, defining org structures is difficult. Reorgs are an iceberg problem; They appear simple at first but get massively more complex as you dive deeper. There are many choices: Should we be hierarchical, or matrix, or a super-sexy hybrid approach? Should we build two-pizza teams like Amazon? They optimize for different outcomes: Do we want tight control and high leverage, …