Less-experienced expect you to have design solutions on tap. Experienced have learned that design is a process. Of course, not all small companies have inexperienced staff — I’ve encountered plenty of small companies with big-company mentalities.

The FBI project in particular — what specific insights did you learn about how an organization like that works?

My experience of working for the FBI was exactly what you would expect when working for a complex government organization.

I won’t tell you what the project was, but it was a few years ago. A very capable coder at the FBI had been tasked with a project outside of her skill set. She reached out to a colleague for help, who reached out to an agency, who reached out to me.

For obvious reasons, security was very tight — doubly so when they realized I was outside the U.S. In the end, a portion of the project files had to be recreated with all content stripped out before it could be surreptitiously emailed to me.

When you’re asked onto a project like that, you’ll find there’s a lot of red tape. You’re often dealing with assets you wouldn’t choose. You’ll be working with partitioned code — or even a partitioned strategy. You will commonly find there’s a chain of accountability of which you are only partially aware.

The answer is to embrace the experience. It’s healthy to be forced into new ways of working, if only to confirm that your preferred approach is best. It will, in the long run, make you a better .

I don’t actually know if the work I did for them made it into the field. Even if it was discarded, as someone who spends most of his days making money for people, it was incredibly rewarding to contribute, in however small a way, to making the world a little safer.

Once you have a project with one of these clients, what approach do you use to keep them happy and thrive while working with them?

Anyone who’s ever run a marathon knows the number-one mistake is going out too hard. It’s the same on a big project. The temptation is to start firing off solutions in an attempt to make progress.

It pays to hold off until you’ve exhausted the problem. A successful solution can always be found by thoroughly exploring the brief. I’ve been in crisis meetings where a simple observation from me has led to a flurry of agreement and consensus on a direction — not because I’m more insightful than the stakeholders, but because I’ve been able to articulate something they already knew but hadn’t previously defined.

When working with complex accountability structures, the best approach to feedback is little and often. Regularly ask for very targeted feedback. No one should ever be surprised by the deliverables you supply.

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