At this time of year we often reflect and sometimes we think "I wish I had stayed in contact" with someone. It can feel awkward to do this and so we don't. However, there is good news (and boy do we need that right now) - the Holiday Season and the global pandemic give us an opportunity to reach out to people we have lost contact with.
I was on a call with Mo Bunnell last week and he was explaining that as business people we nearly all underestimate the strength of 'weak ties'. I agree. Here at Passle we have a tool called ISTATOY (I saw this and thought of you). It is a simple way to send timely, digestible content to contacts - and a great way to keep in touch/get in touch with contacts. Particularly those you have lost touch with or feel a little awkward contacting out of the blue.
My advice is as well as sending the normal "I was thinking of you in these crazy times, happy holidays" type email I suggest you include something that you know will help and resonate with them. Obviously not a sales message but rather something helpful. This could be personal or include a link to some content. A quick post about the challenges and opportunities they are probably experiencing at work or even better a short video message. For video just record yourself on Zoom.
Finally, and I think this is important. Follow it up with a phone call. It seems we have forgotten how to use the phone! Dial their number and say hello.
Check out Mo's video below for more ideas on deepening relationships once you have established connection.