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I am an IT Manager for a relatively small company. At our corporate office, we are switching from Outlook/Exchange to a cloud email platform.

Most of the employees grumbled (they are all used to Outlook), but most knew it was a change they'd just have to grin and bear. They are attending the training and are figuring it out.

A little background on the way I'm tackling this transition:

  1. Outlook will remain available to everyone until the cutoff date. This way everyone can use both platforms at their own discretion to become familiar with the new system on their own time.
  2. Group training sessions on the different sections of the software are taking places every couple weeks. They are hands on and Q/A take place.
  3. Online information is posted so users can train themselves on their own time.

However, one employee (an older lady, if it's relevant), seems basically disgusted with the change. During the transition process she has done the following:

  1. Pointed out even the most minute differences between the new and old software, even those that are changes for the better.
  2. During training, using Q/A time to point out as many flaws as time allows, and essentially ranting about how the change is unwanted.
  3. More recently, stating that the reason she is refusing to use the new platform is because "only those under 50 can understand it". Likewise, she claims the new platform was simply chosen because I'm young and software like this comes "second nature" to "kids like me".
  4. Attempting to rally support from others in the office, not in the form of constructive criticism, but in the form of dissent and general rudeness (it seems to be becoming rudeness directed at me).

It's starting to frustrate me. I totally understand how change can be hard, especially when you have a busy schedule and learning something new is time consuming and seems unnecessary when you already know the old way of doing it.

However, this change is necessary, it's decided, and as far as I'm concerned, I've planned the change so it occurs slowly, smoothly and with plenty of time to learn the ropes without getting overwhelmed.

So here's my question:

What steps can I take to better do the following:

  1. Help the user understand why the change is being made
  2. Train the user so they understand the changes
  3. Prevent the disagreement from becoming personal (it seems it's headed that way)
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What more can I do to ease this user's fears? - do you understand the 'fears'? Is there any element of truth to them? It's worth remembering that it's IT's job to do things for users, not to users. If the new system will make work more difficult for her then this is a real problem that needs to be addressed. It may well be that she's in rant mode because she feels her concerns are not being properly listened to and addressed. It may also be that she's full of nonsense, but in either case the solution is to tackle her objections, speak to her about all her concerns and address them – RobM Sep 2 '14 at 22:02
Please avoid using comments for extended discussion. Instead, please get a room, a chat room. Comments are intended to help improve a post. Also, this is not the place to discuss the merits of different email platforms. Please see What "comments" are not... for more details. – Monica Cellio Sep 5 '14 at 22:15
UGH! In this case the answer really should have been "Turn on IMAP and SMTP over TLS and be done with the matter." – Joshua Nov 10 '15 at 4:14
@Joshua Except, I couldn't at the time and it would not have been an acceptable answer. Thanks for your input, though. – Moses Nov 10 '15 at 19:38
up vote 45 down vote accepted

The basic strategy here is to get her alone, and identify what her core issues are. In this strategy you will try to get her to seperate emotions from facts, and plans from personalities.

  1. If she is a valuable member of your team, then her opinion should be equally valid. Schedule some time with her (a couple of hours at least), and hear her out. It will be lengthy, it will take time, but listen to each of her concerns, write them down, and treat each one with legitimacy.

  2. Once you have a list, sit down with her and talk about the issues you can get the cloud-provider to address. Usability issues are one area they can address. Then talk about the issues driven by emotion that the cloud-provider can't be expected to address. Her assessment that only young people can use the software is an emotional issue. Hear her out anyway, but ask her "what can the cloud-provider be expected to do to resolve this issue?"

  3. Once you've written down her core concerns, talk to a representative of the company leasing you the cloud-based e-mail client. Talk to them about the issues and find out which ones they can address, which ones can be addressed with training, and ones they just won't address.

  4. While you do this, speak with her and let her know that you are working with the provider to find resolutions to her issues. It is critical that she know you're taking her concerns seriously. By investing yourself in her concerns, she will invest herself in the outcomes.

  5. Finally, remember that any financially-motivated major changes should be shared with the users. Is she aware of the savings the company will enjoy after this change is implemented? Aside from disrupting her e-mail skills, how will changing e-mail providers change her daily work? Will it improve? If so, how?

By taking her concerns seriously, you are showing her you also take her seriously. By remove emotions and personalities from the question, are are going to have a few good nuggets that you can bring back to the vendor. If they can show change, your employee will also.

Its very important not to denigrate her opinion or otherwise demean her (eg publically rolling your eyes when she talks). This is an important issue to her, and if she is a valued member of your team, you should treat it carefully and respectfully.

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I was the employee in a similar situation (the issue wasn't just emotional "ick hate!" but some key accessibility problems that made it unusable for me), and the more I tried to get help from IT and got brushed off, the more frustrated I got. Once I got to somebody who was willing to have an actual conversation with me about it, hear my concerns, and work with the vendor, we started getting somewhere and we ultimately found a combination of configuration options that solved the problem. – Monica Cellio Sep 2 '14 at 20:27
I can confirm that this exact approach has worked for me as well - in a similar situation but with a much larger system. – Burhan Khalid Sep 3 '14 at 7:20

You said that "most knew it was a change they'd just have to grin and bear". In other words, IT implemented a change that most users didn't want. It seems then that you made a change that didn't benefit the users. So why was that change made?

Maybe what would help would be just an honest statement like: "Yes, we know that the change in software is annoying everyone and doesn't give any benefits to the user, but we will be saving $100,000 a year in licensing fees". That tells the lady in question that she is right with her assessment of the new software, but she has to bear it because the inconvience to her saves the business money. Right now what she sees is that she is inconvenienced because some kid in IT made a stupid decision without thinking about the needs of the users.

Now of course it is possible that this is actually what happened. That a change was made for changes sake to do something that is more fashionable than Outlook. In that case, you haven't been doing your job and you deserve all the aggravation that you get. The worst is claiming that you made a change to benefit the users when you didn't. Some people just can't stick it if they are lied to.

What is strange is that you say "attempting to rally support from others in the office" as if that was some character flaw. If you live in a democracy, then you should see "attempting to rally support" as a very positive thing. And it seems she is the only one with the guts to speak up, which makes her a very valuable employee.

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What more can I do to ease this user's fears? Is there anything I can do? We're coming up on the cutoff date and I still hear nothing but how much she hates it.

I've been in a similar situation at a prior company.

While it was a different set of technologies, and wasn't email, it was basically a similar "important system migrating to a new technology with a few unhappy/scared/grumbling users resisting".

What they did was arrange an additional series of optional lunchtime Learning Sessions specifically for those who were still having a difficult time adjusting even after the normal training sessions.

During these 1-hour sessions (and basically only during these sessions) users were encouraged to bring their questions, and have them addressed in on a projected screen in front of the group of attendees.

This all served several purposes:

  • Limited the grumbling to just those lunchtime sessions, and permitted the other training sessions to continue unhindered
  • Required a minor commitment from the grumbling attendees to go to a conference room and have their lunch while discussing these issues, rather than having lunch where they would prefer
  • Provided actual learning for the folks who actually wanted to learn

This approach might work for you as well.

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Be careful with limiting training to only during a lunch break. Depending on your local laws, this could be a violation of labor code, eg. – Byrån Sep 3 '14 at 7:21
+1 @Byrån - my lunch break is unpaid so anyone telling me I needed to spend my break learning a technology I didn't want to be involved in, or suggesting later that I'm at fault not volunteering to work through my lunch, would be invited to shove something painful somewhere unrepeatable. – RobM Sep 6 '14 at 13:36

I would talk to her in person and tell her "You say that only those under 50 can understand the new software but I would say from the way you point out the most minute flaws and your knowledgeable criticism that you are one smart cookie. I have no doubt that you are totally capable of learning the new software and if you keep doing this, you're going to make weep - in fact, you are making me weep already :) If you need any assistance from me, I'll be glad to help but honestly, I think you are better able to take care of yourself than most of our users :)"

Frankly, I kind of like that older lady - she reminds me of some of my crankier, smarter, older relatives - and yes, they do make me weep :)

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Older women often feel ignored or despised by younger men, and if you show that you think she's smart (and if you genuinely believe that there's truth in what Vietnhi Phuvan says), that could be the best way to win her round. – S List Sep 3 '14 at 8:29

Always remember that change isn't always a good thing.
Many people in IT (and elsewhere) see something new and instantly grasp on to it like it's the Holy Grail, impervious to criticism or self critique.
The New is always Perfection, anything even a few days older is automatically Bad.

Don't let yourself fall into that trap, analyse the concerns of your users, see what can be done to address those concerns, realise that ALL user concerns have merit.
And above all, don't blindly run after every bit of new technology. New isn't automatically (or rather automagically) better.

I see it all the time, and I work in IT. Hundreds of millions of dollars are lost on project after project to convert things to some new system, some new architecture, for no other reason than that it's there.

Maybe in your case the new system does add business value (and anyway, the rollout seems too far ahead to do anything about it if it doesn't). But keep in mind that the concerns of your users aren't automatically invalid because the user is older than you are. She may be set in her ways, but that may well mean that her way of doing things is the optimal way and the new system will degrade her (and everyone elses') job performance, and THAT is bad for business.

Example of that (and this has nothing to do with technology) is a company that used to take phone orders and ship the goods before the signed order sheet was in their archives.
They got "ISO certified" and now were no longer allowed to ship anything unless there was a signed order form in the books, and payment confirmation had been received, even from long term existing customers with a 100% on time payment history.
This cost them so much business (many of those customers relied on their rapid service to get them critical components faster than the competition, even if they were a bit more expensive) they went bankrupt. All because of change for the sake of change that disrupted a core business process to the point the company was no longer competitive.

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+1 just for the opening 2 sentences! Change for change sake is never a good thing :-) – AquaAlex Sep 3 '14 at 7:50
@AquaAlex most extreme case I ever saw was a guy slagging a camera he had on order as being rubbish the moment a new model was announced which he instantly ordered as well (and received before the older model, the order for which he forgot to cancel). He never used it, but he did 'know' it was rubbish simply because a replacement model had been announced by the manufacturer (delivery had been delayed because the manufacturer couldn't keep up with demand, it was that bad, lol). – jwenting Sep 3 '14 at 8:02
hahahaha i know people like that and also at other extreme which still use OLD stuff because it always worked. – AquaAlex Sep 3 '14 at 9:51
@AquaAlex oh yes, I still use my trusty 12 year old DSLR, nothing in the newer models that is worth spending money on replacing it. That said, were I to develop a requirement that needs something that camera can't meet I would replace it, not try to change the requirement to meet my equipment. – jwenting Sep 3 '14 at 9:53
Exactly! Use the correct tool for the job. – AquaAlex Sep 3 '14 at 11:10

I think there are a few points that you should cover in a private discussion:

  • Ackowledge her fear of change. One of the main office tools that has likely been a staple of her work life is being replaced even though it is just as functional as it was last year.
  • Remind her of the upcoming cutoff date. Offer her additional support if she doesn't feel she will be comfortable with the software by implementation day.
  • Let her know that implementation day is not flexible, that the investment has been made in the new platform and training and that you expect her to be able to continue the level of performance that you have come to expect from her.

All you can do let her know that you hear her but that this course isn't going to change and that you will support her through the transition. It validates her without reopening the issue for debate.

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The solutions to this problem depend on who this old lady is.

Is she a worker that produces something - Manager, Developer, Designer, etc? Is she support - secretary, admin, assitant, reception? Is she a mover and a shaker? (Note - this might be someone from either category above.)

Not all that long ago a company I was working for was trying to migrate from Office 2007 to Office 2010. There was a secretary who used 2003 because she refused to learn any changes in software. This was in 2012 - she was using Windows XP and Office 2003 when the entire rest of the department had been migrated. She was the secretary to a VIP in the company and, as such, a pretty big mover and shaker. We finally migrated that computer when she retired.

This is an example of a person who you may not be able to migrate. Understandably your situation is a bit different - you're shutting down your exchange servers and migrating. But if she is in with an important enough person or she herself is an important enough person then you need to come at things from a different angle.

We had a couple other folks, at the same time, who had tried to put off migration. This is the cynic in me but a lot of them were complaining so that they could have an 'excuse' for any issues. Oh they forgot to do something? It's that goshdarned new computer system! The solution for us, for everyone except the one secretary, was to get buy ins from their bosses. It's one thing to complain about something that IT is 'forcing' everyone to do. It's another thing to complain about something your direct boss is excited or happy about.

That, ultimately, ended up being our problem with our lone holdout. She got to her boss and poisoned the well before we did. Even the oldest, crotchety-est ladies on staff somehow ended up being fine with the changes when it stopped being "the mean IT people are doing this" and became "This is part of your job, if you are incapable..."

That is, admittedly, pretty cynical and a tiny bit mean. It wasn't all stick and no carrot - one on one training with users having problems. Promises(that you intend to keep) that when they have a problem with the system you will be there for them and help them resolve it. That if it's a legitimate problem or change you will go to bat for them. You will stand up and say "Yes Sr BossPerson, Gladys was unable to turn in the TPS reports as you expected and it was because of our system and this is how we've resolved this..."

At the end of the day most people jut want to do their jobs. A lot of people also like complaining. The key to the second problem is to acknowledge the first.

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"This is part of your job, if you are incapable then..." is pretty mean, but you can sweeten it by phrasing it the other way round. "By updating your skills, you're making your CV look so much better! If anything ever happened with our jobs here, God forbid, you'd want your skills to be marketable, wouldn't you" – S List Sep 3 '14 at 8:22

There are good answers here already (especially @Mike Van Trufflebutts answer:

I would like to mention two other things.

The first one is a note, which cannot help you now since the change has already been decided.

It is a good idea to involve the employess/coworkers in your plans of big changes such as the one you described, before the decision for this change is made. This could for example be done by choosing a number of users to test the new system in a testing phase. In that way your employees/coworkers would have had a chance to share their concerns and make suggestions for improvement early on. Maybe the decision would have been made against the new system. Maybe another provider would have been chosen etc.

The bottom line is: the employees would feel valued if involved before a decision is made. (By the way, from your description it seems that you actually value your employees/coworkers, which is excellent!)

Now my second point, which is not addressed in the question, and could be helpful for you now:

However, this change is necessary, it's decided, and as far as I'm concerned, I've planned the change so it occurs slowly, smoothly and with plenty of time to learn the ropes without getting overwhelmed.

It may well be that your plan of implementing the change is really good and a smooth transition for the employees/coworkers, and you support them during the transition and take their concerns seriously.

What is missing for me is that you should also explain the necessity of this change to your employees/coworkers. It shows that you value your employees if you not only make a good plan for a smooth transition, but also give them transparency regarding the decision process. Why is this change necessary?

If your employees feel that they have been given all informations, including reasons for the change, they are more likely to accept this change than without having been extensively informed.

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