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?