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Copyright © 2019 Cloudbreak.


Every week or so I collect a set of articles that have caught my eye about leadership and management in the tech industry.


The articles cover a wide range - everything from the basics of running meetings, to the subtleties of managing remote teams, to the underpinnings of giving feedback and difficult conversations.


Articles I circulate in the newsletter are collected below in the archive.  Feel free to browse, and free to sign up!

I keep your email safe, and I don't spam.


On Minesweeper and Bad Hires - Programming Leadership - Medium

“What if the concept of “bad hires” is more harmful than helpful?” Marcus, with an interesting take on the cost/benefits of the hiring process.

Hiring: When The Water Reaches Your Waist, It’s Too Late, And Other Cautionary Tales

My notes from a few months ago, on a recurring issue I see with my VPE clients: waiting too long before tackling hiring. Hiring is a Big Rock and needs a Big Machine. Building the machine takes a while. Start now.

13 Questions to Get More Feedback From Your Team - Programming Leadership - Medium

Easy read, useful stuff. Exactly what it says - ways to start the “I want feedback” conversation with your team.

Performance Reviews: The Good, the Bad, and What You Can Do About Them

Some good things in here (“the idea of grading on a curve is crap” and “When managers are prompted to recall past negative behaviors (or areas for growth), they will remember those things more accurately and tend to weight them more heavily”).

Also ways to include getting feedback for yourself during the review process. Practical. Good.

Three Star Leadership | Wally Bock | Leadership: There is No Misbehavior

“I’ve said what I want - why don’t they do it??” - the cry of the frustrated manager. “They” are people, and they have their reasons - a simple, but useful post about what might be going on.

What the Success of Rock Climbing Tells Us About Economic Growth | Chicago Booth Review

This seems so simple, and yet is at the core of how companies evolve: “When one person learns how to do something, and when he or she can and does communicate that knowledge to others, the others can quickly benefit from that knowledge, and the group advances”

Learning, and the communication of learning, determine how fast we grow. The article is more about economics than company structure, but its lessons are fundamental.

Resources – Better Allies

Noticed that the pics of folks in your blog posts/marketing material/website all look kinda the same? A super nice set of resources, including stock photos of all sorts of groups, from Better Allies (worth signing up for the newsletter, too).

Managing From Afar: How This Engineering Manager Tackles the Challenges of Remote Work

A whole ton of detailed experience and advice on working remotely - managing meetings, the use and misuse of synchronous communication and more.

“Slack is very powerful, and we can use it really well or really poorly,” Kammah says. “By default, it’s easy to use it poorly—as in, use it as a synchronous tool"

Asynchronous Communication: The Real Reason Remote Workers Are More Productive

A super-useful drill-down on asynchronous vs synchronous communication. Some of the stats in here are hair-raising, the solutions thoughtful.

“This trend toward near-constant communication means that the average knowledge worker must organize their workday around multiple meetings, with the time in between spent doing their work half-distractedly with one eye on email and Slack”

How To Lead Effective Team Meetings: 8 Best Practices + Free Template -

Do we need another piece on how to run meetings? Well, sure, turns out we do. Clear, specific advice, nicely articulated (yes, it’s a bit of a marketing piece for the app but it’s still well worth reading).

Planning with Benefits - Redbubble - Medium

The balance of “top down” vs “bottom up” is always a trick in a planning exercise, so it’s neat to see an approach which has a clearly defined point of view on the problem. Pretty fascinating.

Temporal Dynamics - Coaching Teams Stuck In Discussion Gridlock - The Agile Coach's Guide To The Galaxy

Outlines three personas that can show up in discussion: the Historian (“how did we get here!?”), the Observer (“what’s going on?), the Strategist ("what should we do now??”). Identifying who has which persona can help get a stuck conversation back on the road.

Neat model.

Disrupting Bias in Feedback — Jill Wetzler

A cool, practical post outlining specific ways to notice, and then disrupt our own biases when giving feedback. Great piece.

Listening, Part 1: Introduction – Chelsea Troy

Listening is a pretty deep skill in itself. Chelsea Troy starts to dig in. A good start to what will likely be a good series of posts.

Why I’m Tired of Hearing About the Iron Triangle in Software Development – Management Kaizen

“You can have two of fast, cheap or high-quality” - the ancient mantra of the Project Manager. But does it really apply to software? This piece argues strongly that it doesn’t: quality ends up being cheaper, faster and, of course better.

Interesting perspective. I like it.

Speaking Truth to Power: Reflections on My Career at Microsoft

Pretty fascinating account of working through the Three Phases of Microsoft: Gates/90s, Balmer/2000’s, Nadella/Now. Useful as a study in a) how much a strong leader’s personality imprints itself on a company b) how much that cultural change can impact a company for good and/or ill.


Pretty amazing. A collection of epic memos to internal audiences.

The classics are here: the Elop “Burning Platform” (“We too, are standing on a burning platform, and we must decide how we are going to change our behaviour” sic), the Myhrvold “Roadkill on the Information Superhighway” (1993: “The confluence of wide area digital communications and ever cheaper computing is going to be a lot more traumatic and far ranging than PCs have been”), the original pitch for PowerPoint (yikes!), and many others.

It’s like a peek into the classic crises and turning points of the last 40 years.

Psychological Safety: How to Build a Culture of Psychological Safety

A nice checklist for assessing the degree of psychological safety in a team, and a neat anecdotal illustration of why it’s so important if you want a creative, high-functioning group of people. Good article.

Serving up One-And-Done Criticism Is the Easy Stuff of Fools | the Jane Group

“Delivering criticism to make yourself look good is the easy stuff of fools” and “Criticizing is but the first step in what should be a process. My experience has been that it’s the rare person who’s willing to invest in the whole process”

Criticism is necessary and it takes care to get it right. This post suggests how to get there

12 Mistakes to Avoid in Difficult Conversations - Lolly Daskal | Leadership | Lolly Daskal

A listicle, but a good one. Worth having around to review before you head into a difficult conversation.