Iterate More, Plan Less


I’m always on the prowl for useful insights.

A colleague, Dustin Andrew, has a useful post, Learn to Get Traction in Your Team.

I like his collection of tips, and I found myself using the phrase, “iterate more, plan less” a few times.

When I joined Microsoft, one of my rules was “avoid analysis paralysis.”

I avoid analysis paralysis by taking action, producing results, and changing the approach as I learn.

I’ve learned to improve by versioning perfection over time.

I find it’s easier to settle for “good enough’ for now, if there’s a chance to improve downstream (i.e. perfection as a journey vs. destination)

Photo by Jim Frazier.


  1. Good nugget of wisdom. If I could point to one thing I’ve learned in the past 2 years that has contributed the most to my current (and future) success, this would be it. Iterate more, plan less. Don’t try to understand everything up front, work it out as you go along. This is natural thinking in many areas of life but somehow in software we feel we need to figure everything out up front and then have a perfect run of good luck over the course of a project to stay on track. Iterate more, plan less means you don’t try to make as many assumptions up front (that may be faulty) and you give yourself time to figure out and deal with risks as they are discovered. It feels natural now, but it used to be a foreign and scary concept!

  2. Hi J.D.

    I like that saying, and the meaning behind it.
    I enjoy your work…keep spreading your message.

    Giovanna Garcia
    Imperfect Action is better than No Action

  3. Hi JD,

    Iterate more, plan less, is something I should probably do! Plans change often anyway, so there is little point spending too much time on planning. It’s the “ready, fire, aim aim aim” approach someone else taught me.

  4. @ Jason

    I like the way you connected the dots. I think the key is having a process you trust that let’s you learn and respond.

    @ Giovanna

    Dustin has a way with words. I think it’s a sticky message.

    @ Daphne

    Great point on how plans change often and I’m a fan of ready, fire, aim. It was one of the very first sayings I learned when I joined Microsoft.

  5. Hi JD

    I’ve always been a bit of a planner, but I must admit that now with writing I find the best thing is just to jump right in there and start. As I write I get the ideas and often the first draft is better than if I were to sit and plan and write very carefully.

    Cornel’s philosophy is to have something and then work off it. (He’s also in IT)


  6. Thanks for the idea and explanation. I am a planner. Sometimes I over-think things. I don’t start until I am sure it will work. However, I have also seen that sometimes just fiddling with things, or just starting is the best way to get where I am going. I get to see that things that I previously visualized as oceans are actually puddles. I will write that one down as I tackle a major project in the coming 8 days: iterate more, plan less.
    Thank you.

  7. @ Juliet

    It’s thinking on paper in action.

    @ Steve

    One of my favorite tools for analysis paralysis is time boxing. I also like to use mini-milestones and chunk up progress.

  8. Hi J.D. I’ve failed at some things simply because I never started them. Never got out the planning, need-to-have-everything-in-place-first phase. I truly hope I’m over that bit of self-defeat. Perfection never happens anyway — it’s all about process and unfolding story…

    As always, you make me think. Thank you.

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