Not long ago I wrote about a time I was fired under some pretty stinky circumstances. And then there was the time I worked under the CEO who lied in court about having sexually harassed his assistant. And I still haven’t told the story about the company owner who went to prison. Fortunately, my long career in software development (going on 22 years) hasn’t always been such a bust.
I left the philandering CEO’s employ for a situation where the boss and I just didn’t mesh. Also, after having been a technical writer and editor for seven years I was starting to itch to make software again, like I did in college. So when a well-known local software company was hiring software testers, I applied. I knocked the interview out of the park and got the job.

The company made a large and sprawling product for an industry I knew nothing about, so I had lots to learn. Given my background, the first thing I did was reach for the manuals. Unfortunately, they were incomplete, inaccurate, and poorly organized – unusable. There was online help, but it was unnavigable. Nobody was ever going to use any of it to successfully use the product. My boss managed the technical writers too, so I marched into his office to complain. I wasn’t delicate about it. “This stuff is terrible! I can’t believe you ship this to customers! It’s an embarrassment.”
He leaned back in his chair and calmly said, “What would you do to fix it?”
“I would throw it out and start over,” I began. And then over the next ten minutes, off the top of my head I outlined a project that would create new manuals and online help that would actually help users not just use the product, but get the best value from it.
Three days later, he called me back into his office. “Remember that thing you said you’d do with the documentation? I am promoting you to the manager of that department. I want you to do exactly that.”
It was a bold move for him to take a gamble on me. I’d never managed people, and my project management experience was limited. What I didn’t know was that every year the company surveyed its users about product quality – and every year the documentation got the most complaints. My boss had been told to fix this problem, but he had no grand ideas. Then I walked in with a solution that sounded like it just might work.
Most of this story is just the nuts and bolts of the project – hiring and coaching staff, creating plans and schedules, doing visual and information design for the new manuals and online help, managing the project, reporting to management, and even doing some of the writing myself. The details would be interesting only to another technical writer. Much of this was new to me, but I had excellent support from a boss who needed to see his gamble pay off. He also helped me navigate the inevitable office politics, including another manager who kept trying to torpedo my efforts. Also, the program manager helped me master the project management tools we used, none of which I had ever even seen before. My team and I worked on the project for a year and a half. It’s not often a technical writing team gets an opportunity to do a clean-sheet rewrite like this, and they were all enthusiastic about it. I worked hard to clear their roadblocks, respond quickly to their concerns, and generally be a good guy to work for, and it paid off in the excellent work they delivered. When we were done, we had written over 3,000 pages and had created a seven-megabyte context-sensitive online help system.
I was invited to demonstrate the new online help at the annual user conference. 600 people flew in from all over the United States, and there I was before them on the opening session’s main stage. My presentation was the last of a series about new features in the product. When I finished, to my astonishment the online help received enthusiastic applause – and then one person stood, and a few more, and several more, and soon the whole room was standing and applauding. That moment remains the pinnacle of my career; I can’t imagine anything else ever overtaking it. The icing on the cake was when I overheard the VP of Sales say to my boss, “All the blankety-blank new features we pushed you to put into the product, and everybody liked the blankety-blank online help the best! The online help! You’ve got to be blankety-blank kidding me!”
I used to think I was just a grunt paid to trade the words I wrote for a paycheck. Through this project I learned just how interdependent everyone is at a company, and how everybody is important. Specifically, I learned:
- If you want to see your great ideas implemented, they need to solve a big problem the company thinks it has. What problems does your company think it has? They may very well be different from the problems your company actually has. What great ideas do you have that you can frame in terms of helping solve those problems?
- When you’re doing something you’ve never done before, find people who can coach you through it. I don’t care how far down the ladder you are at your company, your success helps determine other peoples’. Look for someone who both knows how to do the thing you need to learn and whose success depends in part on yours – that last bit motivates them to help you. In my case, it was my boss and the program manager.
- Work for the kind of boss who clears roadblocks out of your way so you can be most effective. I now leave situations where the boss doesn’t help me in this way. It’s that critical.
- Your success always depends on other people, so treat them well. In giving my team an exciting assignment and creating an environment in which they could focus, they happily turned out huge quantities of good work. Also, after we shipped the new documentation, I promoted every writer. They deserved it.
A footnote: That company went through tough times a few years later and so we all moved on, some for better positions and others (like me) because they couldn’t afford to pay me anymore. One of the writers who worked for me called me up one day about two and a half years ago, by which time I really had moved into software testing. She said, “We have an opening here for a test manager. I’d love to work with you again, and this is a good place to work. You really should apply.” I did, and I got the job. I found out later that just before my interview, she went to the VP and said, “He’s a great boss. You don’t want to let him get away.”
Sometimes the good things you do come back to you!
Doing quality work can pay off, too. Here’s a story of a time it really did.