Managing Windows 10 Upgrade Remorse

Eric Riz

by Eric Riz on 7/24/2015

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Date Revised:

Applies to:
remorse, Windows 10 upgrade

Planning for and managing Windows 10 upgrade remorse will help you win over reluctant users in the long run  

When Microsoft released Windows 10 on July 29, 2015, millions of users had the opportunity to join the 5 million Windows Insiders who have played such an instrumental part of the product’s release thus far. Virtually overnight, the pool of users grew exponentially, and I can tell you from experience with other operating systems that if the pattern holds true, some users will love Windows 10 while others will hate it. That’s the reality of any upgrade from one product to the next, and its human nature to sometimes feel remorse over what you’ve “done.” This is analogous to selling your old car and then having thoughts about all the places and experiences you had together. Your old operating system, regardless of the version, was comfortable and you knew how to navigate through it. At a minimum, you knew how to get your job or task done with minimal disruption. Regardless of your specific situation, the creature comforts of your old operating system will be gone, and you’ll be left with a new system to navigate, which may cause you to turn your nose up at Windows 10 altogether, regardless of the enhancements it contains.

As an individual, your upgrade experience may leave you longing for your old operating system. As someone who may be part of a larger organization, the decision to upgrade may have been made for you, but the result can easily be the same; a longing for your previous operating system and frankly, fears about the future. This is something that has been written of in the Journal of Personality and Social Psychology. A 2012 piece entitled, Buyer’s Remorse or Missed Opportunity, addresses how purchases can be divided into two different categories; material or experiential. A material good is made to be kept in the buyer’s possession, while an experiential good provides the buyer with a life experience. In the context of Windows 10, this interestingly falls somewhere between these two experiences; as an operating system can be both material and experiential. This research explains that regrets of action are intense, but only in the short term, while regrets of inaction gains intensity over time and dominates people’s experience. As time goes by and users read about the various ways that Windows 10 has been embraced by organizations, they may regret their inaction and begin talking about wanting the new operating system. Both of these experiences must be addressed and managed accordingly to ensure happiness amongst your users.  

In terms of upgrading, there are many experiences that your users will have over the coming weeks. For the organization, your interest at a fundamental level is that Windows 10 functions as expected, and allows your users to perform their job in as seamless a way as possible. That’s obvious. What isn’t as obvious is trying to identify those people who experience upgrade remorse and potential ways to turn their viewpoint around.

Here are three steps to conquering upgrade remorse for your team:

  1. Identify the issues – Depending on the role of the individual, you may be in a position to simply ask how the person is enjoying using Windows 10. Someone with a positive answer will respond immediately with exactly that level of response; something positive that shows a degree of satisfaction with the operating system. Conversely, someone who isn’t enjoying their experience, or who finds using Windows 10 frustrating, will pause to find the right words for their answer. Note this potential negative by calling it out immediately and trying to have a discussion about the experience. Remembering that their issues may simply be a reflection of insufficient training, so ask for some usage scenarios to better understand the issue. When the issues are (hopefully) out on the table, don’t rush to try and respond with a solution. Because many issues can be systemic and shared by a number of users, your best response is to accept the feedback and compile a common list of the issues experienced. From there, you can ask others in the organization for their feedback and then devise a plan to correct the common problems.
  2. Create a mutual plan – Once you have identified a list of issues, creating a plan with your colleagues is critical to long-term adoption and success. Working together shows your users that the organization is committed to their success with Windows 10. While this step may seem intuitive to some, it is critical and should not be overlooked. Sitting down and hashing out a training and adoption plan will help mend fences with your users; hopefully moving their thoughts from remorse to acceptance and potentially even excitement. Remember that sometimes users just need to be shown a new way of completing an old task in order to gain their acceptance.
  3. Overcome the hurdles – Unfortunately, there is no doubt that upgrading to Windows 10 will ruffle a few feathers within the user pool of your organization. What’s critical is that users see that a clear strategy has been set out that includes their use and efficiency expectations long term. As Microsoft’s next generation operating system, users can expect to see their organizations align to a larger vision that includes reinventing corporate productivity through business processes and using data to benefit and bolster organizations. Working together, the “business” and “IT” can create a great future for the organization. To assist with this, I recommend creating a general mailbox for users to send Windows 10-specific questions. In the coming months, be sure to check on these questions and with users to ensure they are working stress-free. Plan for a formal get-together in 3-6 months between your teams to answer any questions from the group and consider sending out a newsletter to highlight features of Windows 10 that your team has collectively discovered that make them more productive. 

Topic: Windows

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