Recent Posts

Estimating ROI of AI Developer Tooling

As engineering leaders see their AI tooling bills rise, many are asking how to estimate the ROI of that spend.

Their engineers offer qualitative feedback that AI agents are significantly speeding up certain tasks, but the finance department sees quantitative dollar figures. This contrast creates a pressure to quantify the AI payoff.

Measuring engineering output effectively is infamously difficult to achieve. Fortunately, there is still a way to estimate AI effectiveness – by comparing outcomes between when AI assistance is present and absent. The following is an experimental technique for doing so.

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Making Retros Work: Turning Reflection into Peak Performance

The retrospective (or “retro”) is a standard Agile team meeting held to reflect on how a sprint went and what improvements could be made. Its purpose is to help teams perform better over time.

Unfortunately, they’re often a fraught meeting.

Common complaints include that they feel forced and formulaic, that they devolve into venting about issues outside the team’s control, or that they descend into struggle sessions.

Teams under tight delivery pressure resent them. So do teams with weak psychological safety.

But the worst indictment a retro can receive is: nothing changes.

Despite this, they’re one of the most important practices an organization can have. Problems with retros do not stem from their fundamental purpose, but from how they’re implemented.

This article will explain how to address common complaints, restore trust and motivation in them, and maximize their effectiveness.

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Managing Distributed Teams Effectively

Managing distributed teams can feel like management on “hard mode”, but it doesn’t have to be.

While the COVID pandemic made working from home mainstream only recently, distributed teams and remote work have been around for centuries, despite far more limited technology.

When Magellan set out to find a westward route to the Spice Islands, he was effectively leading five distributed teams, with no way of communicating back to his boss – King Charles I of Spain – after departure.

When British America was governed from London, messages took six to eight weeks to cross the Atlantic – a situation that continued for nearly two centuries.

The point is not that managing distributed teams is easy, but that the principles involved are well understood. Technology has added nuance, but when companies struggle to align teams across time zones, it’s usually due to weak fundamentals.

In this article I outline the core principles of managing distributed teams, and review the practices followed by leading remote-first organizations.

I also explain why many managerial tools commonly relied upon in in-person environments – which remote work naturally restricts – are actually net negative for productivity rather than practices worth preserving.

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