That was my first mistake. Sure enough, hot on its heels came another one, wearing a full-body smile. I couldn’t resist. “OK”, I said, “You can come in too.”

Then a third idea showed up, this one a bit more obstreperous. “You let them in. I want to come in too!” “Uhh… I guess so.”

Some of those ideas were so charming that they were hard to resist. But before I knew it, there was a crowd of them, each struggling to be the first to slide into the keyboard. With all of their jostling, none of them could get through. If I couldn’t break that logjam, this post was never going to happen. “Stop! Time out! All of you, go to your rooms! Now!” I hated to see the looks on their faces, but I had no choice. I’m trying to write a blankety-blank blog, not The Great American Software Book.

That crowd of ideas came out of some discussions about Agile software development at last month’s No Fluff Just Stuff conference in Boston. It’s fitting that in dismissing them (at least for now), I was applying a lesson from Agile: Don’t try to do everything at once. Create and deliver in small increments instead. You get feedback faster this way, and your customers get the use of your work sooner.

This isn’t the first time I’ve taken a concept from Agile to use in domains that are removed from software development. How To Make Mistakes was essentially a distillation of Agile concepts. I’d even suggest that one of Agile’s greatest strengths is that it helps to create a process for making better mistakes. Conversely, one of its greatest weaknesses may be that few people recognize this.

How does Agile help create better mistakes? To illustrate this, I’ll list the guidelines that I set out in How To Make Mistakes with their foundations in Agile:

• Understand the risks: The most popular flavors of Agile, such as Scrum and Extreme Programming, emphasize specific methods for identifying and mititgating risks.
• Define your goals, Seek feedback early and often, Assess and Adjust: I lifted these fairly directly from the Agile Principles.
• Work consciously: This mirrors another Agile Principle: At regular intervals, the team reflects on how to become more effective, then tunes and adjusts its behavior accordingly. Such reflection can and should be a part of each developer’s personal work methods too.
• Make your own mistakes. The Agile Manifesto states a preference for “Individuals and interactions over processes and tools.” Similarly, the Agile Principles declare that “the best architectures, requirements, and designs emerge from self-organizing teams.” Put together, these remind us: No process, however intelligently it was designed, possesses its own intelligence.  Human intelligence must be allowed to trump process guidelines. In fact, any well-designed process must include guidelines for overriding and updating itself. Agile processes are living processes.

One of the risks to successful Agile adoption is having unrealistic expectations. Business stakeholders may expect that a “better” software process is one that results in fewer mistakes being made. A more pragmatic expectation might be that Agile can help a team make better mistakes, which eventually will lead to fewer being made. Better mistakes and fewer mistakes both lead to better results.

I may have some other ideas on this, but they’ll have to wait for another time.

“Wheee!” [*Splash*!]

Back to your room! I’m closing this post down now!

The professor’s meaning came through loud and clear to the student: The mistakes of a master may have greater merit than the rest of us can achieve with our best work.

I had a glimpse of this truth early in my career—not from an older master, but from a younger one. I was two years out of college when Jim (not his real name), fresh out of MIT, started working with me on a project. At first I was put off by this youngster’s apparent arrogance, but gradually it dawned on me that the guy knew what he was talking about. I began to seek his feedback on my work, and a good friendship developed between us.

Some time after Jim left the company, I told him that I’d been making a bit of a career fixing his mistakes. He was distressed to hear it. No worries, I assured him: he’d made the right mistakes. His work conveyed a good understanding of the problems that he’d been addressing, and was clear enough to help me absorb some of that same understanding. The overall structure was sound; the mistakes were usually in the details.

There was one arguable exception, though: Jim had solved a particularly thorny problem using a very non-traditional approach, which was difficult to maintain after he left. He’d been aware that this unusual technique could become a problem, but he’d concluded that the alternatives would have been worse. Regardless of whether Jim had made the best possible decision at the time, he deserves credit on several grounds: He’d considered different ways to solve the problem; he’d brought the best tools to the job that he could find; and above all else, he’d solved the problem. If his choice was a mistake, it was a mistake well worth making.

To err is human, or so it’s said. It may be even more human to fear erring. While this fear is often well-founded—it can, after all, save lives—it can also be costly. An excess of caution causes inaction, which often is also a mistake. And as has often been said, every mistake represents a learning opportunity. Since we are all bound to err sooner or later, it follows that we’d do better if we stopped trying to avoid mistakes, and started aiming to make the right mistakes.

Making the right mistakes requires using the right process. In fact, making the right mistakes is all about using the right process; what mistake you make matters far less than how you make it. The better your process for making mistakes, the better your mistakes will be. Drawing upon my vast experience at crafting mistakes, I offer herein some tips that may help you improve the quality of your own.

• Understand the risks. When lives or vast fortunes are at stake, it’s probably not a good time for taking risks. Yet even when the real risks are lower than that, we still carry a severe aversion to mistakes. This can do more harm than good. Many of your mistakes will be forgotten in time; for others, you’ll have chances to make amends. Move your work forward based on what you know, or can learn fairly quickly.
• Define your goals. What are the essential criteria? You and your customers need to agree on these points before much serious work can begin. Beyond the essentials, spend less time analyzing and defining, and more time doing. When choosing between building something good now, or something better later, go for the good. Today’s omissions will be tomorrow’s opportunities, if they are missed at all. Focusing on the essentials will help you respond to requests faster, which will help facilitate the next item on the list:
• Seek feedback early and often. The sooner you discover your mistakes, the easier they’ll be to correct.
• Work consciously. This isn’t some New Age concept, but a very down-to-earth process. Think of it as your personal continuous improvement or Kaizen plan:
  • Observe yourself as you work.
  • Consider what you’re doing, how you’re doing it, and why you’re doing it that way.
  • Look for better approaches. (There’s always a better way. When mistakes are possible, so is improvement.)
• Assess and adjust. Look for your mistakes, take responsibility for them, and learn from them. Don’t let problems fester. Get other people involved, when you need to, but without seeking to assign or dodge blame.
• Make your own mistakes. Understand what’s required. Listen closely to the advice and wisdom that other people have to offer you. But if you think that your best path goes down a different road than the one you’ve been pointed down, then follow that thought. Your successes will be sweeter, and your lessons will be learned more clearly.

There’s a question that’s posed in various places around the Internet:

What would you do, if you knew you could not fail?

That’s too broad for me to answer concisely. (Fix the current economic crisis? Bring peace to the world? Travel in time? My taxes?) Instead I ask myself a slightly different question:

What would you do if you had no fear of making mistakes?

I’d take piano lessons, and I’d write a blog.

One down, and one to go. I think I’m off to a pretty good start.

Update 08 Sep 2011

This is too good not to include here: