🐿️ Sheriffs on the Spot - The Insanely Profitable Tech Newsletter

Originally published 18th March 2024

It might seem most effective to march into your tech team at high noon like Marshal Kane, enforcing law and order and good software process while sweeping dissent aside and pushing a product vision. You can’t beat the drama of the brave sheriff with the star-shaped badge who rounds up or guns down the ruffians to clean up a crooked town all by himself–but unfortunately, in my experience following this script only leads to bad decisions and worse morale, as important information and ideas from those closest to the code and the customer get thrown aside. Instead, it’s more helpful to model interventions after a different kind of sheriff–the ones who worked for King Henry II of England in the 12th century.

Henry’s vast empire stretched from Ireland to Spain, but his orders could travel no faster than his horses and their riders could carry them. So by necessity, he delegated local authority to a number of “shire-reeves”, who fought off raiders, kept the peace, and–most important to Henry, who was constantly at war and short of cash–collected taxes. To ensure he squeezed out every penny he could, the king required his sheriffs to gather once a year for the “reckoning of the exchequer”, where each one stepped forward nervously to turn over a bag of silver coins, count them up, and give the reason for any shortfall. Cooking the books could land you in an oubliette or worse, but if, say, you explained honestly that your collections were light because Scottish marauders had burnt most of your citizens’ crops, Henry might send aid in the form of an army expedition. “Rendering an account” as these sheriffs did is where we get our word “accountability”, and it shows nicely how you can ensure your tech team are answerable for their outcomes, and get the help they need, by putting them in charge of frequently reporting results.

The technique I usually recommend for effective accountability is briefing and back briefing (from Bungay’s Art of Action): agree on the goal, constraints (like budget or delivery time), and freedoms (e.g. to choose technology or staff members), then get a rapid read-back from the team on how they are going to execute (the “back briefing”) and have them schedule frequent demos of working software so you can monitor progress and offer assistance. The key words here are “rapid” and “frequent”: we can work and communicate at speeds King Henry couldn’t possibly imagine, so we should be seeing results from the tech team weekly or even daily. As I explained to a CEO in the spaceflight industry recently, when you lean forward and issue vigorous orders like a Wild West sheriff, the team leans back and waits for your direction, so they accomplish less; when you lean back and wait for results, they fill the space with action but may go catastrophically wrong. This is what Roger Martin calls the responsibility virus; my preferred cure is, like mediaeval kings, to pull your “sheriffs” toward you and ensure they, not you, are in charge of incessantly demonstrating value.

This first appeared in my weekly Insanely Profitable Tech Newsletter which is received as part of the Squirrel Squadron every Monday, and was originally posted on 18th March 2024. To get my provocative thoughts and tips direct to your inbox first, sign up here: https://squirrelsquadron.com/