Training employee on new technology when they are DEAD SET against it...

I had a smaller scale version of this issue about 2-3 years ago. I did IT on-the-side for the very small law firm I worked at, and I spearheaded and executed the transition to Google Apps, in large part to help the legal secretary handle multiple calendars and the owner's emails (things she had been complaining about for years). I was in charge of training her in the new systems. She dragged her feet the whole time. Pointed out every perceived flaw. Had diatribes about how the old system was better and this new system was awful because of X, Y, Z, despite the fact that it worked wonderfully for the rest of us and helped streamline so many processes. I took all the problems to the big boss and let her handle it. She was outraged at the secretary and it was a lot of drama (this also wasn't the healthiest company, BTW). I guess the secretary was notorious for this kind of push back; for example, she refused to transition from Word Perfect to Word for over a decade. We were still fighting the secretary about Google Apps, when I left a full year after the launch. But you know what? Performance management wasn't my job. Deploying the software and troubleshooting issues was my job. And that's what I did, and I let the boss handle the performance problems. Schedule a meeting with the Director and clearly, objectively explain the roadblocks you're experiencing. It won't come off as whining; don't fall into that line of thinking, because it WILL bite you (trust me, I know from experience). They didn't hire you to be a management/HR consultant; they hired you to develop software. Let the Director manage her people.

Obviously this is a HR issue. However! I have no idea if I ought to bring this situation up to the director. This is actually not an HR issue at all! It's precisely the sort of thing that the Director is needed for. Your problem is that Anna does not answer to you, so you rely on her goodwill to get her to do what she needs to do. Since she doesn't want to adopt the new workflow just on your say-so, she needs someone who's actually in her chain of command to tell her to do it. What you may need is a meeting with all of the stakeholders (ie, everyone who uses the new system, including Anna, so as not to single her out) led by the Director where the director outlines the new tasks and workflows and duties. And then to have all emails regarding the new application cc'd to her to make sure everyone is in compliance. how can I do it delicately and productively without getting her or myself fired? Keep in mind there is a possibility that Anna will either believes that she will not get fired and will be able to outlast this change-of-workflow or that Anna will prefer to get fired rather than change. To a degree she sees herself as a long time established institution of the organization and you as just "passing through." And/or she may be comfortable with being fired if she feels she was "unfairly" let go.

Also: you need to reframe this to yourself as a problem that must be solved instead of feeling guilty. Anna deserves to be fired, and she's probably going to lose her job over this sooner or later, as she should. But if you skitter into this situation cowering and apologizing, the director will sour on you. Stand up straight, smile, and be sorry-not-sorry that progress stops for no one. Re your update: then it's the director's problem to solve either way. Do not approach her as having an HR problem. You have a software deployment problem. The director may have an HR problem, but you are not HR.

It's up to the director to push the change through, NOT YOU. Director made policy change, not you. Should not be your problem to "convince" them to adopt the new methodology.

On the softer side, when I am dealing with deployments that are a big change, I acknowledge out loud to the users all the time that change is hard and change sucks and I am sorry to be the bearer of the change but The Powers That Be have decided that this is how it's going to be. That's why you get TPTB involved, in part to make sure everyone remembers who made this decision and it wasn't you.

This is where you'll find out if the organization you're working with is a good one or a bad one. Good: the director will insist that Anna gets with the program or gets fired. Bad: you'll be asked to change the workflow of your software to fit Anna's way of doing things, and/or when you leave Anna will go back to using the same processes she always did and the director will let her. This happens a lot in academia where jobs are often viewed as "for life" and people will bend over backwards in ridiculous ways to allow someone close to retirement to keep doing things the way they've always done them, no matter how much it inconveniences their coworkers. Either way, though, it's the director's job to solve.

Maybe ask Anna to help create a manual for how to complete various tasks with the new system? It could be a good way to reinforce the learning experience, especially for people who are not web programmers and may benefit from more context about how everything works. A project like a manual or FAQ could apply her expertise about the organization to build and maintain an accessible resource for future questions about the systems.

hey santry, there was a long planning process and she had many many, opportunities (both one on one meetings and general ones) to speak up if her needs were not met. I do not believe the problems are poorly solved (of course I wouldn't) but more importantly, the director, who is extremely hands on, has worked with me every step of the way and is thrilled with the results. If Anna had/has issues and does not speak up that's really her own problem. I can't solve problems I am unaware of.

Do you have a training outline? Make one. Break down the things that need to be learned. Schedule time with Anna and other staff. Report progress to the Director, i.e., Anna, Pat and Lee have begun work on the Q component. Leslie has mastered the R component. Tell the Director that staff are having difficulty embracing change, ask for a visible show of support. If Director checks in with staff and makes it clear that the software is a high priority and that she's Paying Attention, it will help. Approach Anna with lots of flattery, treat her like a friend, show her ways to make herself look good. Director will be so impressed that you've mastered Phase I. Wow, you'll be really valuable as the in-house expert on this software. That report is so useful, you're helping Organization do its job. Put the training outline someplace visible, when anybody masters anything, put a star on the outline with their name. or some other way of rewarding people. Give out small packets of M&Ms for success. What gets rewarded gets repeated. Many people react poorly to change, especially if it makes them feel dumb, threatens their livelihood, makes them work harder and change their established habits.