Sometimes I hear from people who are having a hard time finding a job or clients for their business, working on establish healthier habits, or sorting out their finances. The Internet tells me that people who are struggling generally don't need more advice, since they've been told by everyone else around them to apply to jobs, go to events, exercise, lose weight, stop eating junk food, stop buying coffee, etc. In fact, we should probably stop asking how things are going and stop trying to solve people's problems for them. Ditch the clichés, too. Sympathy, encouragement, support, and maybe even a little distraction are apparently the way to go.

It got me thinking about different purposes for conversation, and how to match someone's purpose better. Mismatches can lead to frustration on both sides, like when you're really looking for advice and different perspectives and someone fobs you off with “You can do it!”, or when you're feeling like this situation will never end and someone passes on a piece of trite advice that you'd already tried on day 1, or when someone just wants to talk and you jump in with a problem-solving mindset.

It feels a little weird to explicitly talk about what people are looking for in a conversation, but what if clarifying that up front can lead to a more effective exchange? You could minimize those mismatches or even direct people onward if you're not in the right space for a conversation. For example, although people have told me that they appreciate how positive I am (which is good for when people need encouragement), I catch myself becoming impatient if people just want to vent without taking action. I'm much better with breaking down big challenges, finding alternative approaches, and celebrating small steps forward (even if they're minuscule). I read extensively, so I can tell people some common approaches to different life challenges, but I don't have a lot of personal experiences because my life has been pretty straightforward.

There are so many different kinds of conversations, so I'll keep the scope of this reflection manageable by focusing only on the conversations where someone has started by describing a problem. What are some of the things people look for, and how do I want to respond?

Advice (rarely): “You should…” is a common response when people share what they're going through. People rarely need additional information, but oddly enough, they get spades of it (even unsolicited). It's not like it's difficult to search the Internet or find books about different life challenges… and yet it's so tempting to fall into the trap of thinking that just a little more knowledge will help people solve their problems.

I've been curbing the impulse to give advice by reminding myself that people are generally smart and usually try everything before asking for help. Instead of “You should…”, I often phrase things as “You've probably …. How did that go?” If they hadn't done it yet, I ask what's been getting in their way. I rarely have experience with the particular situation they're in, but barriers tend to be common, so I can share how I've dealt with those – not in a “You should” way, but rather “Here's what I tried and what worked for me.”

Acknowledgement: Sometimes people just want someone to see them and know what they're going through. This is the “Oh, you poor dear; let's have some ice cream and you can tell me all about it” sort of thing, I think. Active listening techniques (restating, etc.) can help here. I'm not particularly good at this yet, but I might get better at this by focusing on the interestingness of people.

Distraction: Sometimes you just want to have fun and take your mind off stuff. Like acknowledgement, but this time you're having ice cream and watching your favourite movies or something like that. I'm not particularly good at this yet, but I can get better at this by asking people what they want to do.

Encouragement and celebration: “I'm in a sucky situation, but I'm working on it. I'm making slow progress, but I'm making progress!” “Woohoo! You can do it!” is sort of how this conversation goes. It's like acknowledgement, but people are moving forward instead of getting stuck. I like cheering people on, and I might be able to do even better by helping people track their progress so that they can see how they're doing over time.

Thinking out loud: I often find myself understanding things better when I explain them either to myself (through blogging) or to other people. Conversation is great for making sense of and making peace with things. People can ask questions to probe your reasoning and direct your thinking, helping you deepen your understanding.

Active listening and thoughtful questions can help. For my part, I can see it as a way to learn from other people's lives and thought processes, so there's a lot of benefit in doing this too. Learning about therapy might help here.

Poking holes (rarely): “I'm going to …” “That might not work because of …. Have you thought about …? What about …?” It's mind-boggling how many people have this as their default reaction, actually – probably second to advice. My parents used to struggle with this a lot, because my dad would come up with wild ideas and my mom would immediately have her “How would we make this actually work?” hat on. I hardly ever do this with other people, although I do this myself to test scenarios: come up with ideas, then put on the “What could go wrong?” hat and poke holes, then update the plans to address those holes.

It's probably better to assume people are not looking for this unless they explicitly ask for it. If people do want this, I like approaching it from a “Let's make the plan better” perspective rather than the “You suck at planning” perspective.

Accountability: It can be easier to take action or change habits when you publicly commit to that, and having a friend follow up with you and keep you accountable can help a lot. I do okay with this, although I don't actually enforce anything in case people miss their goals. (Perhaps I should start insisting on some kind of consequence – maybe ice cream.) Learning about coaching techniques might help here too.

Different perspectives: “I'm in this situation and I think you've been in something similar. How did you solve it?” is the gist of this conversation. Sometimes knowing that something is possible (because someone you can identify with succeeded at it!) is enough to give you the strength to get through the situation.

Requesting help: This is where you're asking for help. Requesting specific favours do well, I think, because that makes it easier for other people to recognize situations in which they can help you. That's why it's good to describe your ideal client and ask friends to keep an eye out for people matching that description, describe your ideal contact and ask people to check their networks, etc.

I feel like my network is not as plugged-in as it could be in terms of business owners and potential clients for friends. I probably need to meet more people who need stuff! Hmm, actually, the input part works pretty well in terms of sketchnoting/graphic recording – I get the occasional request that I can forward to other people. In other areas, I can usually point people to other people who have experience in the kinds of things they want to do and the meetups to check out, so I guess that's something. There's room to work on this, though! Time to go to more events and connect with more people. Although come to think of it, that's not actually the thing that worked for me in sketchnoting – maybe I'll focus more on creating useful stuff, and go to a few events for serendipity.

Acknowledgement, distraction, encouragement, thinking out loud, poking holes, accountability, different perspectives, requesting help… What other purposes have you noticed when you talk to people about life's challenges?

I happened across this First Annual Festival of House Culture while browsing through my Facebook news feed. As it was in the neighbourhood and one of the events promised to be a philosophy salon, I figured it would be a good excuse to try something new. I shared it with a couple of friends who are also into that sort of thing.

It was an enjoyable get-together: two musical performances and a free-flowing conversation that covered friendship, culture, community and connection. I signed up for the mailing list so that I can find out about monthly events. Apparently, there's a series called the Piano Salon. I met a number of people that I'm looking forward to bumping into again. It felt like my kind of thing (versus, say, going to clubs or sports or movies).

I've been thinking about some of the things we chatted about. Here are some thoughts:

What is house culture, anyway? I think of it as opposed to going-out culture and homebody culture. Going-out culture involves spending for things like movies, dinners, and shows, although sometimes you can find free events or organize a picnic. Homebody life is more like relaxing at home by yourself or with a few other people. House culture might range from having a few friends over for brunch to having a mini-concert that includes friends-of-friends or even strangers.

I think it's interesting to be at home (or someone's home) instead of a commercial or public space. There's something about being surrounded by someone's regular life. Hanging out at home is more convivial and less commercial, too. I don't have as many get-togethers as I probably should. I remember that I always get stressed out right before the actual party. (“Why do I keep doing this to myself? What if people take offense at not being invited? What if no one comes? What if lots of people come and there aren't enough seats? What if I get introvert overload? Gah, the house isn't clean yet!”) Also, W- is even more of an introvert than I am, so I don't want to impose on him or cut into his weekend recharging time. I should remember that I actually do enjoy the conversations, that friends will forgive the occasional dust-bunny, that W- is okay with disappearing off to gym class or into the basement to work, and that everything is going to be okay. I'm up for meeting friends-of-friends, but I don't think I'm comfortable with opening the house to complete strangers yet. Anyway, I can build up slowly. Also, people are awesome and they can help me learn.

Here are some tips for organizing a house concert/salon. We're probably not quite at that point yet (music? seating? layout?), but maybe someday.

How does one make friends? We talked a little bit about what intimacy is, and how shared vulnerability can build trust. I'm not particularly good at being vulnerable around other people. This is likely due to a combination of:

• All those lectures about how you should be careful about what you let people know about you. Sure, most people are good, but it only takes one person to really screw up your day/life/whatever. And it gets worse on the Internet.
• I skew towards happiness, rarely feel angry or sad, and am learning to apply philosophical principles to minimize weaknesses and negative emotions. There are a few things that make me anxious, but I tend to be more comfortable working on those things myself.
• I'm not used to asking specific people for help. I can often piece things together from the Internet or research, and I'm more comfortable with writing rather than talking as a way of thinking things through. I feel like putting blog posts out there and being open to follow-up conversations (either online or in person) is a little less of an imposition compared to asking specific people about their opinions.

I'm more curious about the Aristotelian idea of friendship between good people: a mutual admiration and help sort of thing, maybe? So for me, getting better at making friends might be more along the lines of learning what's interesting and admirable about people (there's always something) and using that curiosity to get over the friction I feel when it comes to planning get-togethers or going to events.

… though I sometimes amuse myself with suggesting and arranging such little elegant compliments as may be adapted to ordinary occasions, I always wish to give them as unstudied an air as possible.

Mr. Collins in Pride and Prejudice (Jane Austen)

After three successive weekends (three!) with parties, I want to think about small talk and how I can tweak it. Small talk is unavoidable, but there are things you can do to nudge it one way or another. I like having conversations that move me or other people forward, even if it's just by a little bit.

So, what do I want to do with small talk?

• Help other people feel comfortable enough to open up about some memorable interest or quirk
• Find topics of common interest for further conversation
• Find a way to help or a reason to follow up

We could do the ritualistic weather/profession/how-do-you-know-the-host conversations, or we could change the level of the conversation so that it goes beyond the repetitive gestures that only skim the surface. I could chat as a way of passing time (possibly bumping into interesting thoughts along the way), or I can more deliberately check for things I'm interested in while staying open to the serendipity of random connections. What do I want to be able to frequently do through conversation?

• Identify possible meetup or global community members – reassure them that this is a thing and that lots of people are interested in it; point people to resources (Emacs, QS, visual thinking)
• Talk shop with other geeks to find out about tech and business things worth looking into
• Other geeks (non-tech): learn more about different fields
• Non-geeks: See if there's anything I can help with easily (books? ideas?)

I could either dig into people's interests or be memorable enough so that people look me up afterwards. Many people open up about their interests only when they feel comfortable. What makes people feel more comfortable? It helps to establish a sense of similarity and shared understanding.

People have different strategies for establishing similarity. I know a few people who use the “You look really familiar…” approach (even if the other person doesn't) because rattling off schools, companies, associations, and interests tends to reveal something in common.

I like building on stuff I've overheard or asking questions about common context. That's one of the reasons why I like events with presentations more than events that are focused only on networking – the presentation gives us something to start talking about.

In terms of helping people get to know me and find topics of shared interest, I use short disclosures with high information value.

Consulting: “I'm a consultant” has low information value: it's vague and it wouldn't establish much similarity even if the other person was also a consultant. I rarely use it unless I'm tired, I want to shift the focus back on the other person quickly, or I sense they're also going through the motions. (Or I want to see at what point their eyes glaze over…)

Emacs: “I'm working on some Emacs projects” has high information value when talking to tech geeks, almost like a secret handshake that lets us shift the conversation. (I talk faster, go into more detail, and use more jargon when talking to fellow geeks, so it's almost like the 56kbps modem handshake.) I'm female, I don't wear geeky T-shirts, and I don't work for a technical company or in a technical position, so it helps to verbally establish geek cred quickly without making a big deal out of it.

Data analysis: For geeks of other fields, Emacs is low-information, but Quantified Self and data analysis seems to be a good way to establish that similarity quickly. It works well with people who are interested in science, tech, engineering, math, or even continuous improvement. Litter box analysis is surprisingly engaging as a cocktail party topic, or at least it's easy to for people to ask follow-up questions about if they want to.

Sketchnoting: People (including most of the ones who don't identify as geeks) tend to be curious about my sketchnoting, since it's visual, easy to understand, and uncommon. That said, I need to get better at handling the usual follow-ups. People tend to say things like “You draw so well” or “I could never do something like that.” I want to nip that in the bud and get people to realize that they can do this too. Pointing out that I draw stick figures like a 5-year-old doesn't seem to do the trick (“Ah, but you know what to leave out” and “But you're doing this while listening – that's hard”). Maybe a little humour, poking fun at the idea of going to an art school that specializes in stick figures or learning how to not fall asleep in presentations? About one in fifty people I talk to recognizes this as something they do on their own or that they want to do, and it's good to link them up with the global community. For most people, though, I feel slightly more comfortable focusing on ideas they want t olearn more about and sending them sketchnotes if there's a fit.

Semi-retirement: This experiment with semi-retirement can be a good conversational hook for prompting curiosity. It usually follows this sequence: semi-retired -> “aren't you a little young? what do you mean?” -> tracked, saved up, experimenting. It tends to be too detached from people's lives, though – many people don't think they can pull it off, even experienced freelancers who are doing most of it already.

Variety: If I don't know how someone identifies, it's fun to answer the “What do you do?” question (which tries to pigeonhole someone into a neatly understandable job title) with a sense of variety: “I do a lot of different things! This week, I …”

Going forward

For the next few events, I think I'll experiment with doing the tech/non-tech/non-geek identification earlier, or going into that with an opening based on variety. I could name an example each for tech, non-tech, and non-geek, and see which one they dig into. As for digging into people's interests, maybe an open-ended survey-type question would be an interesting way to help people open up while still collecting data in case people haven't thought about how to make themselves easier to get to know. Hmm…

Small talk might be small, but if I have thousands of conversations over the years, I might as well keep learning from it. How have you tweaked how you do small talk?

When it comes to socializing, I have a high coefficient of static friction. I tend to stay in place. If I let too long go between get-togethers, I fall out of the habit of hosting them, the identity of someone who brings people together. I rarely ever want to go out. I drag my feet. I look for excuses to stay at home. I resist when invited, and only manage to make myself go because of social expectations.

When I'm there, though, sometimes it's all right. Sometimes it's awkward. But sometimes it's fun and almost frictionless, and the time speeds by.

I should remember those times so that it's easier to push myself to go out. The risks are small, anyway.

What makes some get-togethers feel okay? I like board games and card games. They create new situations for us to interact in and result in new in-jokes. They give my hands something to fiddle with. At the same time, there's still space for conversation between rounds and during breaks. I find background conversations too distracting when I'm trying to work on something, so I prefer to work at home. Pair-hacking might be interesting, though. I like talking through complex things much more than conversations just about catching up. I like having a sense of accomplishment or learning.

The weather's warming up, so maybe I'll have a get-together sometime. Gotta ramp up to it again. Maybe I'll check out Gamfternoon at HackLab.to. Maybe I'll try going to more HackLab open houses. Maybe I'll invite people over for a casual get-together. Daylight Savings Time kicked in, so I guess introvert hibernation mode is winding down… We'll see!

I used to think a lot about how to keep track of the people I know, writing down notes about their interests in Emacs' aptly named Big Brother Database (BBDB). I wanted to be the kind of person who could remember people's goals and dreams, who paid attention to trivia from long-ago conversations. A little configuration allowed me to see my notes when reading or replying to e-mail from people, and I even wrote some code to track when I last contacted someone and filter the list of people so that I could focus on people I hadn't talked to in a while. It was amusing to see a record and realize I'd actually known someone for years (these things sneak up on you before you know it!), and it was occasionally gratifying to be able to look up someone based on an interest I vaguely remembered them having and to make the connection with a book I'd just read or someone else they should meet.

I kept tweaking this system. Maybe there was a contact relationship management tool out there that could help me remember what was important to people's lives or discover small-talk topics from people's social media updates. Maybe there was an application that could help me act thoughtfully, beyond the usual flood of Facebook wall messages on someone's birthday. Maybe there was a way for me to learn how to keep in touch. I asked people who networked for a living (mostly salespeople and politicians) how they managed to remember all these little details and reach out. They told me about spreadsheets and index cards, phone calls and e-mails: “Hi, how are you doing? Was just thinking of you. What's up?” I was inspired by examples of super-connectors who somehow managed to remember everyone's faces and names, asking after kids and pets and hobbies, effortlessly breaking through the limits of Dunbar's number. (Or at least it seemed effortless; many worked very hard at this.) I tried out systems like Nimble and Contactually as a way to see people's activity across platforms and remember to keep in touch. I tried ConnectedHQ (no longer available?) and Sunrise for people-related notes in my calendar. I followed Facebook and LinkedIn's suggestions to greet people on their birthdays or job changes.

Still, those practices never quite felt natural. Maybe I'm just not a people person, at least not that kind. I never became comfortable with calling someone out of the blue, and I preferred posting stories on my blog instead of telling them one-on-one through e-mail or conversation.

I decided to try a different approach: I stopped worrying about keeping in touch. If people came into my life, great. If people drifted out, that was fine too. Instead of working on keeping those relationships going, I focused instead on being open to the conversations as they came up. Instead of reaching out so that I can hear about what people are working on and stay on their radar, I decided to focus on what I was curious about and be open to the people I'd bump into along the way.

Sure, I might have missed a few serendipitous connections with people who were quietly working on interesting things–but the world is full of other people who make it easy to keep up with them, like the way my blog makes it easy to keep up with what I'm interested in. I subscribe to a number of people's blogs and I follow people on social networks. But for the most part, I care about ideas and conversations first, and then getting to know and keep in touch with people happens along the way.

It's a very different form of networking, I think, than what I've read about in countless books. I still recommend books like How to Talk to Anyone (Lowndes) and Never Eat Alone (Ferrazzi) to people who are curious about building relationships with specific people or making the most of networking events. Me, I'm learning about how to talk to everyone. Instead of building a relationship with a specific person, I look for opportunities to help people around an idea or contribute to a group. Instead of asking a specific person for help, I ask in general, and people step forward if they're interested. I don't have to fear rejection, and no one has to look for tactful ways to say no; and if a request doesn't get any takers, well, I'm where I would've been anyway.

In order to make that work, I need to make sure I have good ideas that people want to be part of, the confidence to share them, a platform for sharing them with, specific requests and ways people can get involved, and a way to celebrate how people are helping. I like that. It turns networking into something more than “I think you're cool and I want to stay in touch” or even “You're working on cool stuff; How can I help?” – it becomes “We're all part of something bigger. Let's make things happen.”

I'm working on sharing, learning from people, asking for help, and making it easy for people to build on what we have in common. I'll get there someday. It's not so much that I want to keep in touch with a specific person; it's that we're both actively thinking about a topic, so maybe we'll set up a conversation so we can exchange notes and learn together. It's not so much that I want to have a wide range of skills in my roster of contacts; it's more that I want to provide value to a wide range of people, and maybe some of them will want to help me when the opportunity comes up.

I was thinking about the way people are related to topics so that I can nudge myself to reach out more for questions and conversations. I like the idea of confederates: people who are actively learning about similar things, and whom I'm comfortable asking if I want a different perspective or I'm curious about what they're learning. I don't have any set schedule for reaching out to these people. If I learn something they might be interested in, I'll mention it to them, but I'll also open up the conversation to everyone who might be interested. When I started drawing out the map, I realized how lucky I was to have so many people I can learn from and who might find stuff I'm learning useful too. This is how I keep in touch now – through the exchange of questions and ideas.

So I might not build as close a relationship as you might with someone who takes the time to send you birthday cards or calls you up every quarter, but then do you really feel all that close to insurance or real estate agents who send you cards like clockwork? I don't send “Hi, what's up?” e-mails and I tend to not be very good at responding to them, but I'll dive deeply into topics of mutual curiosity. My network is shifting to people who share what they know and what they're learning. While that means I'm probably missing out on a lot of stuff that never gets shared beyond the small circles most people are comfortable in, there are so many good people out there focused on bringing everyone up–not just the people they've bumped into. It might also mean that I'm not as close to the people for whom these little gestures mean a lot, but it means that I draw closer to people who don't have that need. It's like the difference between someone who puts you on the spot when you forget your name and someone who helpfully supplies it at a hint of hesitation; someone who makes you feel bad for forgetting their birthday or anniversary or whatever, and someone who's more focused on what's good instead of what's missing.

You don't have to wish me a happy birthday, and you never have to apologize for replying slowly or not being in touch. Better to share your questions and ideas, and better to share that not just with me but with the world.

If I want to learn about more than I can explore in my own life, I'll need to learn from other people. The easiest way to learn is from people who are already teaching: books, courses, and so on. Although I could probably spend my entire life doing so, it might be interesting to go beyond what I can learn from books and classes. That's because books and classes have to be written for a certain kind of audience, and learning is further restricted by the time it takes to create these resources and the kind of people who can do so.

I can learn from coaches and mentors as well. Coaches may have explicitly thought about what they want to teach and how they want to teach it, but they customize the approaches and tips for each person (at least good ones do). Mentors might not have thought about the topics as much, so if I want to make the most of mentorship, I should get better at asking questions as well.

An interesting challenge is to learn from people who might not step forward as coaches or mentors. Some people have thought a lot about what they do as they improve it, but they might not have realized that other people would find that useful, or they might not have gotten around to sharing. Finding them is probably the key challenge; once we make the connection, we can have a geek-to-geek conversation. Other people do good stuff without having thought about how they do it – unconscious competence. In addition to the challenge of finding them, there's also the challenge of articulating how and why they do things, maybe through interviews and observation.

I'm pretty decent at learning from books. I'm working on getting better at tracking how I came across a book so that I can thank people, and so that I can see the book in the context of the great conversation. I'm also working on translating ideas into actions and experiments. Books are familiar and well-understood.

Coaching, on the other hand… I could probably make better use of coaching, if I find good matches. Essentially, I'd be investing in faster insights and more effective learning. Could be worthwhile. What would make me say, “Yes, that was totally worth it. I grew in ways I couldn't have done alone. Let's continue.”? Path-finding, I think – a quick way to sort through decades of experience and all these resources.

What am I generally curious about? Systems, paths, estimates of effort and reward, other people to learn from, blind spots…

So that's for formal coaching relationships. For informal learning, like the conversations we have over years of blog posts and the serendipitous connections we make on Twitter, I'm curious about getting stuff out of people's heads and helping them share that with other people. People are learning all sorts of cool stuff, but (a) few people slow down and write about them, and (b) sometimes you really do need someone else to ask questions, so if I share what I'm curious about, maybe I can connect with people who have spent some time thinking about these things too.

Mel Chua and I were talking about interview techniques, and she mentioned how instant replays are great for helping people break things down. You watch people do something, you do an instant replay as you try to explain what they're doing, they say “No, no, no, I did it because ____”, and you iterate until both of you have a clearer understanding. Sounds interesting. I wonder how we can do that online… Timothy Kenny‘s approach is like that too, except not in real-time. He analyzes the behaviour, and then discusses the model with people to see if it can be corrected or clarified.

Anyway, that's my plan for getting better at learning from people – more conversations, and then eventually regular conversations. I think that will help me get to a more awesome place than I can on my own. =)

Have you deliberately worked on learning from people?

I’ve been giving a lot of people advice lately (Google Helpouts, lunches/coffee with people, and so on), which is weird for me because I hedge what I say when I’m writing on my own. My blog posts focus more on the “Here’s what I tried, and here’s how it’s working for me” rather than “You should do X, Y, Z.”  When someone asks me a question or describes a challenge they’re facing, though, I have no problems offering suggestions.

I thought about what advice is like and how I can give it more effectively. I realized that there are actually lots of different ways you can help people by talking to them, and it’s not all about saying “You should do X, Y, Z” with minimal understanding of the other person’s situation. Here’s what I came up with:

(Click on the image for a larger version)

I’ve read about and tried a lot of approaches, so I really like the “Have you thought about…” way of helping people. I do that after a few “Tell me about…” so I understand the person’s context and we can build on things they’ve already tried. Sometimes people ask me about how I make decisions too, so I’m happy to walk people through that. (Especially if I’ve already documented it!) On rare occasions, I can tell people the name of the thing they’re looking for (ex: spaced repetition! cloze deletion!) which unlocks all these resources for them. When I’m writing on my own, I like using “Don’t miss… / Watch out for…” to help people save time.

Giving advice still feels odd. I definitely don’t want to become an “I know better than you” sort of person. I like using questions more than declarations anyway. Maybe I’ll find an approach that works for me!

How do you share what you know? How do you help others learn?