Most companies are made up of the following groups:
Management
Accounting
Sales
Development
Information Technology
Human Resources
Marketing

This company is no different. We have all 7 fields here. Here are the general responses I get from each field (Obviously I’m in IT)

Management: “I don’t care how much it costs or how long it takes – just get the upgrade finished with minimal downtime”
Accounting: “That costs too much – find something cheaper or free. We also need the systems to be up 99.99% of the time – especially over weekends and holidays”
Sales: “I’m very important, without me making money for the company you wouldn’t have a job. If something doesn’t work, I’ll find a way around it even if that means I break stuff further”
Development: “I need rights to everything”
Information Technology: “We’re f***ing awesome!”
Human Resources: “Don’t touch each other, yell, run, or laugh. Oh, and we have a new person starting in 20 minutes, so setup a system for them – and no, I don’t know their name yet”
Marketing: “I need a faster computer so I can design this for a trade show”

/rant.

So onto the meat of the situtation:
The company recently upgraded from CRM 3.0 to CRM 4.0. That’s a huge upgrade. Huge. CRM 3.0 is going End Of Life in April of 2011, so we figured we would get a head start on the upgrade process. That and Management told us to upgrade. The Dev and QA teams checked everything out before, during, and after the upgrade.

Unfortunately, a single sales rep was having issues with his contacts losing their parent links during offline/online synchronization. We checked out his company-issued laptop had his personal Comcast account tied into Outlook. Every company I’ve ever been to or worked for has a “no personal email” rule for Outlook. This company apparently allowed it until recently. This sales rep thought he would be grandfathered in.

So I send him an email saying that he will have to remove his personal email from Outlook. He comes and visits me at my desk:
GUY: “So what you’re saying is that there’s a limitation on the new software that doesn’t allow me to use it the way I could before?”
ME: “I’m saying that some of your problems may be attributed to the personal email account as well as your contacts being spread between the server and several PST files”
GUY: “How do you suggest that I view my comcast mail then? It’s rather important and tied into a lot of things that I do”
ME: “Web access?”
GUY: “I’ll have to do a bit of thinking about it and get back to you”

At that point he walks away. I figured we’d be done – no one else has their personal mail ‘tied into’ the system. Who would be that ‘stupid’?
Argh, then he comes back (10 minutes or so later – I really need to get an office with a door…)

GUY: “So you’re saying that I might have to get a second laptop for personal use?”
ME: “If you want to maintain the exact same functionality with Outlook, then yes”
GUY: “Why did it work before the upgrade? Do you know if removing Comcast will solve the issues? And is this some sort of new rule here?”
ME: “I’m not exactly sure on the company policy for personal email – all I know is that every other company that I’ve ever been to disallows the use of personal email on a company-issued system. How about we sit down next week and discuss this further?”
He walks away again. But then I overheard him talking with another coworker:
GUY: “…I don’t know why they just pick and choose to upgrade things without letting us vote on it or at least have some sort of say in the matter…”
and “…they’re hindering my productivity…” “…I need that account for a lot of company business…”
Awesome.

So then I get a call from him:
GUY: “What about my blackberry? How can I sync up my comcast mail and my work mail on the blackberry?”
ME: “The same way you normally would?”
GUY: “So I’d have a Desktop Manager on each laptop and then sync that way?”
ME: “Uh, I guess you could do it that way – hopefully it doesn’t overwrite the other data”

Apparently he uses POP3 to download comcast to his Outlook, and then uses the Desktop Manager to sync with his blackberry. Talk about backasswords.