So I’ll start by admitting that having three small children, running a small business, and trying to get the logistics of life to run somewhat OK is slightly challenging. 
One thing that tends to slip my mind is the small social things relating to people I meet regularly, but not as frequently. So I meet them, we do some small talk during our interaction - something comes up, and I’d like to remember to check in on it next time we meet.
“So how did that trip go?” / “How’s it going with this or that project?”
I hope I’m not the only one with this challenge… and was thinking that someone might have a good system in place for alleviating this? 
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at the danger of sounding like a broken record: omnifocus is your friend here.
I have both my business, private and social items all in this one place.
When I meet someone and would like to ask them something whenever I meet them next, I store that question in omnifocus tagged with their name. The “People” perspective I have then allows me to easily retrieve it.
(actually this also goes for my wife and kids, anything I want to discuss with them, but can’t do right away goes into omnifocus,)
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You can also use the little notes section in the contacts app for this kind of information about people. I just want things I have to do in Omnifocus and keep everything else separated (i.e. books I want to read are in a list in Devonthink etc.)
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Yes, I was considering this - but was getting a bit worried about cluttering up OmniFocus too much. In a scenario where someone suggests something for me - like reading a particular book or checking something out - then the action itself would typically be added as a Task in OmniFocus, but I’m not sure if “remember to talk to Person X again about it” would go in as neatly. Especially if I end up having too many tags.
But I guess this is the closes solution to something workable I see at the moment. Ideally I’d like some kind of App that would just add on a layer of information on top of the Contacts I’ve got - with easy management etc.
I agree the OmniFocus route could be used here. This sounds like what the GtD method refer to as “Agendas”, things to talk to a person about the next time you meet, but don’t really need a due date.
There used to be great contact managers where this information was easily tracked. For some reason, this product category seem to have disappeared or been integrated into huge CRM-type solutions.
If anyone knows about a decent contact manager that integrates with the Contacts database on macOs and iOS, I’d be very keen to learn about it.
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I can understand your hesitation.
In my case: if I can’t put it in Omnifocus, why did I buy it?
OF for me is the trusted place where I am 100% sure to find all my tasks and all agenda items related to people.
I only see the agenda’s (people) perspective “on purpose”
- During my weekly review (quick check)
- If I am going to meet / meet someone I quickly check their tag. Usually I will the just flag the relevant items to show them in the flagged perspective for the day. (= my usage for flags)
In all other circumstances it does not show up in any perspective unless I flag something or add an additional tag that shows up in some perspective during the weekly review.
My DB is patient, that is what it was made for, and I always have all items on hand, wherever and whenever I want to see them.
I do it this way because I don’t want to go hunt for tasks/ideas/people items across several apps as I already have one that works for me.
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I use TheBrain for this information. I have a Thought for the person, in the notes of that person’s Thought, I have notes about our last conversation that way I can review it before I meet them again, or if I see them, I can quickly pull up the thought on iOS to review before I say hello. Under their Thought, I have various thoughts such as (Persons Initials)-Dates. In that Thought, I note any significant dates I know about that person. (Person Initials)-Relationships, any significant relationships this person has: partner, spouse, children, etc.
If it’s a working relationship, I connect them to projects we might have worked on together as well as their skills. That way if I am working on another project and I need someone for a specific subset of tasks, I can check TheBrain and know that this person has a background in this type of work.
All of these are first written up in Drafts, so I can record it while it is fresh in my mind, then when I am back at my Mac or work desktop, I can connect it to the right thoughts or create new ones if needed.
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I’ve tried using different or separate apps for this but I always come back to my task manager, which happens to be OmniFocus. I just have a single action project that is just named relationships and have tags for each person’s name. I also have a perspective that shows these relationships. On iOS I can just pull down on the homescreen and type in the person’s name or type relationships and either go to that tag or the perspective really quickly.
One thing that I do to remove all the friction is to specify how I am going to follow up in the task title (call, text, email, visit, etc) and then in the notes field I always put a link to whatever method I am going to do. If its an email I put the email address, phone call or text I put the phone number, etc. This way it removes all friction when I am going to do it. I’ll even go one step further and type in the message that I’ll send them. For example, if I want to follow up with a friend on how his marriage is doing I’ll put the phone number and type out a message like “Hey man, I just wanted to check in about our last conversation a week ago about your marriage. I hope things are going better, keep me posted.” Anything I can do to remove friction helps.
Depending on the follow up I will sometimes set a notification. If it is a simple text, especially one that I’ve written out, I will set a notification that I will most likely not be doing anything too important (i.e. at night after the kids are in bed, Sunday afternooon, etc). The notification is less intrusive because I just have to act on something that I’ve already written out.
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