We caught with up Esther Derby in the middle of snow storm and hoping the airport is cleared before she has to fly out to Webstock in a couple days time! In addition to her conference presentation, Esther is running a full day workshop on Agile Retrospectives.

1) Tell us something about your past work history and how you’ve arrived at where you are.

I started my professional career as a programmer. I wrote my first program using punch cards. My first portable computer looked like this:

Some things about our field have changed a lot.

Other things…not so much.

I was really good at finding the source of odd behavior or errors in large systems. My managers noticed this, and promoted me to be a manager. I believe this method of selecting managers remains largely unchanged.

It is true that all complex systems share certain characteristics, the parts are interconnected and a change in one element can have ripple effects throughout the system. The connections aren’t always obvious, and the fix many be far away from the effect. Still, the skills needed to steer a human system (which is what managers need to do) are just a little different from those that made me good at trouble shooting software. So I set out to learn a different set of skills.

Along the way, I earned a Master’s in Organizational Leadership, studied family therapy, and took a dive into Humans System Dynamics, a new field that applies concepts from chaos and complexity science to groups and organizations.

In my first years as a manager, I missed the challenge and satisfaction of solving technical problem; I’ve come to learn that working with human systems is just as intellectually challenging and just as satisfying. Does tend to be a bit more messy, though.

2) Have you always worked with an Agile methodology? If not, did you have a “ray of light” experience that brought you to it?

I’ve been around long enough that I’ve seen methodologies come and go. When I look back over the teams and projects that worked best, we were applying at least some of the principles of agile development. We found ways to build feedback into the system: working in small chunks, testing early and often, keeping public project progress posters (the precursor of Big Visible Charts). We worked in the same office and we had frequent communication with the people who would use our products.

What got me interested in Agile (with a capital A) was the explicit emphasis on collaboration, sustainable pace, and pride in work. I’ve seen too many organizations where work is a dehumanizing slog. Life is just too short to spend 40+ hours a week that way. Many teams have had success using agile principles and methods. I’ve heard from scores of developers that the Agile teams they worked on were the best work experiences of their lives.

Sadly, I think many organizations are drawn to agile because they see it as a way to squeeze more work out of people. Sort of like the days when executives didn’t read past the word Rapid in Rapid Application Development. The truth is that if executives want to get more done faster, they have to look at the work system, and the way they manage.

3) Why do most managers suck so much?

Most managers want to do a good job, but don’t know what to do or how to do it. It’s not surprising, since most managers in software organizations are promoted into management from technical position (as I was). So they do what they’ve seen their managers do. Or if they’ve had a bad experience, avoid doing what their manager did.

The broader problem is that the predominant mental model of management is way off. I know, all mental models are wrong….and some are wrong in ways that are more damaging than others. Much traditional management thinking focusing on getting people to work harder and smarter with carrots and sticks. But the most effective way to get everyone to work more effectively is to work on the work system so that everyone can do better.

4) You’re giving a workshop on ‘Agile Retrospectives’. Who should attend and what will they learn?

Agile retrospectives are the engine for continuous improvement on teams. Anyone who wants to learn how to help their team think, learn, and improve together should attend. Same for anyone who has dull, do nothing retrospectives. We’ll do a project, have a retrospective, and then learn how to design effective retrospectives by examining the pieces and parts of a retrospective and how they fit together–all without PowerPoint!

5) What are you most looking forward to about Webstock?

I’ve heard so many wonderful things about New Zealand. I’m looking forward to visiting Wellington, catching up with some old friends, meeting new people. I’m also looking forward to the energy and drive that just rolls off the Webstock program. I’m sure I’ll have fun.

Thanks Esther. And we can promise there will be no snow in Wellington in February!