TimeZest can provide value all over an MSP and in a variety of situations. However, when you need to schedule time with users to help them through something like the upgrade to Windows 11, TimeZest is a huge difference maker, cutting the time spent wrangling customers to a small fraction of what it takes to do manually.
The logistical nightmare of coordinating with dozens, or even hundreds, of busy employees across all your clients is a huge hidden time-sink. It’s a flood of back-and-forth emails, endless games of scheduling ping-pong, and missed appointments that destroy your technicians’ productivity and frustrate the very clients you’re trying to help (even if they don’t want the upgrade). TimeZest removes the scheduling bottleneck so your engineers and clients can focus on the work, not the back‑and‑forth.
Every client is different, every MSP is different, and a lot can be done with agents these days to patch workstations, but MSPs we talk to schedule at least two types of appointments to perform the OS update:
- Upgrade Session – to kick off the OS update and supervise the process.
- Validation Session – a brief follow-up to confirm the user can work and answer questions.
This avoids surprise downtime and can turn a mandatory upgrade into a positive touchpoint.
Additionally, if a new machine is needed to accommodate Windows 11 (or it’s just a good excuse to get rid of a clunker), TimeZest can help with device deployment as well. We’ll go over some best practices in scheduling a project like this so that you can remove one of the worst parts of the entire thing for your tech and clients: manually scheduling appointments to get it done.
Schedule the Upgrade
While your RMM might be able to do the upgrade with little effort, it’s still important to work with your client to find a mutually convenient time for the upgrade to take place. The last thing you want to do is run an update while a client is cramming for a big presentation the next day.
For this we recommend you create a dedicated appointment type (e.g., “Windows 11 Upgrade”) in TimeZest.
Make it effective:
- Slot length: Plan 60–90 minutes to cover downloads, 2–3 reboots, and final checks.
- Windows: Limit booking to your defined upgrade hours (add an after-hours window for high-impact roles).
- From the ticket: Send the link from the PSA ticket so every interaction is documented automatically.
- Department waves: If you’re planning on doing machines at a specific time it still may be a good idea to provide a scheduling link to your main point of contact to pick a mutually convenient time for their entire staff to be off of their devices..
Schedule the Validation
A new OS is a great opportunity to check in with clients and not only validate the upgrade went as planned, but that each member of your clients’ teams have their IT needs met. However, the simple act of getting everyone manually scheduled can actually consume more time than the validation meetings consume. Unless you happen to find a mutually agreeable time within the first reach out, which doesn’t reliably happen, you’re wasting your time and your client’s time unnecessarily.
Instead of one technician offering a sampling of their own availability, TimeZest can present a whole team’s combined availability. This gives you the best possible chance of accommodating your client when it’s convenient for them, instead of the times your engineers happen to suggest from just their own calendar in a single convenient step. When doing this manually, each follow up to schedule is 15 minutes on a timesheet. When scheduling a meeting can take a half of a dozen attempts to accomplish (especially when you include rescheduling), you’ll find an hour or more reported on timesheets setting a meeting that often times takes less than 15 minutes to perform.
Most importantly, when sending a scheduling link from TimeZest, you’ll want to constrain the times this meeting can be scheduled because you want to make sure it occurs after the upgrade is due to happen. This is easily done from TimeZest’s PSA scheduling pod like so:
This is also a great feature to use when you’ll have a engineer on site for a specific period of time while the upgrades are happening. This way it’s easy to make sure the on-site team member(s) has their week scheduled for them and arranged before they arrive with very little effort. It’s also helps make sure they’re not simply mobbed when they get there, everyone already has time arranged to meet with them.
Schedule the Deployment
When a Windows 11 upgrade requires a hardware refresh, keep the rollout under control by having end users book their setup before they unbox. Include a bold “Schedule Your Setup” QR code or shortened link (e.g., bit.ly) on the box or a slip inside that points to a TimeZest Shareable URL. The moment they pick a time, TimeZest creates/links the ticket in your PSA (ConnectWise, Autotask, or HaloPSA), updates your tech’s calendar, and sends confirmations—eliminating back-and-forth and preventing unassisted plug-and-pray installs. The result: predictable schedules, happier users, and faster Windows 11 cutovers. Learn more about deployment scheduling with TimeZest here.
You’ve Got This!
Don’t let scheduling hold you back from helping your client through transitions like this. Scheduling is a bigger time suck than most people realize for projects like this and it’s where TimeZest is indisputably indispensable. As always our support team is here to help get a game plan together. If you’ve got a mountain of upgrades to get through, don’t panic, we’ll be here to help!
