Hot boss, cold boss: This tech pro just had no chance

Two bosses can't control their feelings and miscommunicate, sabotaging their current contract and a potential new one

Communication is an art, one it seems a project leader would possess. But one contract I was working on went south due to disagreements between the customer and our team's leader. There was good news for me: I got hired by the customer to work on the same project, albeit only for a little while.

A small supplier of custom software had asked for a jack of all trades. I applied and found myself working my way through five interviews with the business leader, who became Boss A. When asked if I could familiarize myself with five technologies while reworking a vintage software system, I confidently answered, "Yes."

[ For more stories about exasperating IT jobs, check out "10 users IT hates to support" and "7 blowhard bosses bollix up IT." | Pick up a $50 American Express Gift Cheque if we publish your tech story: Send it to | Get your weekly dose of workplace shenanigans by following Off the Record on Twitter and subscribing to the anonymous Off the Record newsletter. ]

I found myself reworking a software system for a corporate customer that published law materials. The software system, chosen by the customer for the project, was a complex amalgamation of several hundred files creating a Web interface written in 1995-ish Web technology, patched onto a back-end system dating back to the 1980s. It was legacy software and lacked documentation, a contact person, or a supplier -- they'd been out of business for years.

I succeeded in updating that system's user interfaces, including making JavaScript run properly even when it resided in files that called each other recursively. It became more responsive and user-friendly. And our team wrote data converters to port SGML data, which the customer supplied, into the file structure of the system.

During that time, I communicated with some of the customer's staff. But all contact with the project leaders went through my boss, whose solid technical expertise was overshadowed by the fact that he couldn't control his emotions.

That's one way to sever a contract

One day, Boss A came back from a meeting with the customer, his face purple with rage even several hours later (it was a long drive to the town where the meeting had been held). Sputtering, he explained that during the meeting the customer had requested new features -- impossible ones! He told me to write up a report confirming this, which he would pass along.

But I recognized many of the requests as ideas the two of us had discussed when we were brainstorming. We had acquired extensive knowledge of how to make the old system do new tricks, but Boss A had decided not to offer them since he thought they would be too time-consuming and costly. However, with the customer requesting them, it seemed like we could at least offer the option and build in fees to cover our expenses and time. Boss A agreed with me that the features were doable, but he still insisted I write up a report telling the customer they weren't.

I never learned the customer's reply. But one day, a few of us were fired because they had canceled our supplier contract on the grounds that they were now consolidating their supplier relationships. There wasn't much to do but start looking for another job.

The next day, I was leafing through a computer magazine and did a double take when I came across a job advertisement from the same publishing company. The job description didn't fit my skills entirely, but I applied because it involved technologies I had already worked on for them while employed at the software supplier. Could I simply continue my work? It seemed like a dream opportunity.

I landed an interview, which did not go well. First, the person interviewing me -- who was to become Boss B -- didn't seem interested in me as a person, rarely making eye contact or small talk. Another detail that might help explain the strange feeling I got was that, a few days before, an accident had left me with a serious black eye. Many strangers had asked me about it. But, even after a long interview, this person never mentioned it. During the whole encounter I got the feeling I was considered a robot and not a human being.

The final reason I didn't feel good about the interview was that Boss B asked me about my knowledge in many technologies I'd never heard of before. Can you do this? No. And can you do this? No. It went like that for seemingly 10 minutes, during which she never looked at me, her eyes fixed on her checklist. I figured I wouldn't get the job.

1 2 Page 1
Page 1 of 2
InfoWorld Technology of the Year Awards 2023. Now open for entries!