How to Fix Apple Watch Contact Syncing Problems
Some people are experiencing problems with Contacts on their Apple Watch, or with initiating phone calls with Siri on your Apple Watch. The problem may be that your Contacts aren’t properly syncing, and Mac Geek Gab listener Bill wrote in (MGG 626) with the skinny on resetting it.
The Issue
The problem is that your Apple Watch is displaying phone numbers for some or all your incoming calls, even when the people calling you are in your Contacts. Alternately, you may find that Siri on your Apple Watch is unable to do something like, “Call Dave Hamilton,” even though Dave is in your contacts.
The Solution
To fix this, try resetting your Sync Data in the Watch app on your iPhone. It’s easy enough, but the last step isn’t entirely intuitive. Start by going to iPhone > Apple Watch > General > Reset > Reset Sync Settings. the following screenshots were taken in iOS 10.

Main Screen of Watch App on iPhone
On the screen above, tap General, and then scroll to the bottom and look for “Reset.'”

General Settings Screen for Watch App on iPhone
That will take you a screen with three options. The bottom one is “Reset Sync Data,” as shown below.

Reset Screen in Watch App for iPhone
When you tap “Reset Sync Data,” the button will flash. And that’s it. You get no additional feedback letting you know the data is being reset, but that’s what’s happening. You’re done, and your Contacts should be properly synced in just a few minutes.
Related
I’d call this an interface fail, for what it’s worth. It seems to me you should get a pop-up sheet that asks if you’re sure you want to reset data syncing, with an explanation that accepting means it’s happening.
That’s it! Thanks to Bill for writing in to Dave Hamilton and John F. Braun with the tip.
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