I don't think you can do that configguration. The reason why is that speed dial function is only used to make outbound calls and cannot be configured to be a shared line for monitoring status on 7914 side car or 7960 phones. The only way to monitor the line state on 7914 of an extension eg. Managers DN is to configure shared lines instances.
You can add a new button template by going in ccmadmin to Device\Device Settings\Phone Templates... in this page you will find templates like "Standard 7960".
Click on the standard one and then click copy, give the new one a name, and you can change each available line to either speed dial, service, or line... you should see lots of lines to account for the possibility of up to two 7914s...
If you set them all up as lines, then update it and go to your phone config page you can set this new one as the button template.
Then you can add shared lines for all the ones you want to monitor.
Unfortunately as far as I know there isn't a way to be able to transfer/call these buttons directly - pressing them will pick up the line.
You can do it with CME but not with CM.
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