Humans are not automatically strategic. Our goals are complicated, the world is complicated, and actually doing things is hard. This means that the default state of the world is that you are missing out on a lot of ways of achieving your goals, both small and large. And this is normal and to be expected! We all procrastinate, neglect opportunity costs and the value of information, are over or under-confident about our own abilities, and are generally mired in a range of biases that hold us back from being effective.
One interesting side-effect of this, is that it’s often way easier to notice these mistakes and biases in other people’s heads than in mine. And it’s much easier to make progress when you have somebody else helping you! You can separate the cognitive work of actually strategising and doing, from the cognitive work of paying attention to biases and keeping yourself focused. And, as a result, I’ve noticed that I’ll moderately frequently have a conversation with a friend where I notice that they’re missing out on ways of achieving their goals, and try to help them fix this. This is a bit wordy, so I’ll henceforth refer to this as debugging their problems.
This is something I would have assumed would be annoying, but people generally seem to be grateful and appreciative! (Even after trying to account for the inevitable sampling bias) So I’ve mostly decided that this is something worth continuing doing, and a way to add value to the lives of my friends (if they want it). This post is my attempt to write up my thoughts on how to do this well, and in ways that don’t make my friends hate me!
Health warning: If you actually intend to try these ideas, I recommend explicitly asking people if they want help solving their problems! This can be a way to add a significant amount of value, but can be super annoying if they’re tired and just want to vent, or aren’t actually interested in solving the problem.
With that aside, I think this is a really valuable skill to cultivate! It can help your friends become much more effective people, and I find it often helps me to debug my own problems, by mentally framing it as giving advice to somebody else.
The first and most important point - you are helping them to solve their problem. The goal is not to have things to progress the way you think they should, it’s to help them make progress. This is an important distinction, because it means you need to be open to the (likely) possibility that you’re wrong about the problem and it’s solution. They have way more context on their life than you do, and will often have missed out subtleties at first. This means that:
If I think I get what’s going on, and have an idea for the solution, I’ll first para-phrase back what I think is going on, to check that I’ve understood right. And then my favourite technique by far is the Socratic method. Rather than explaining my idea for a solution, I’ll ask leading questions that can lead them through the thought process I went through. If this goes well, then they’ll generate thoughts such that my solution makes sense. And if this goes even better, they’ll give an unexpected answer to one of my questions! And this is awesome, because it shows I misunderstood something, and we can dig into that, with no harm done. So, either we get to the same point, but in a way that feels more intrinsically motivating, or it fails gracefully and I discover that I’m wrong.
Some specific ways I use this:
Often an underlying problem is that they feel stuck and thus aren’t really trying to solve the problem - it feels overwhelming and unpleasant to think about, and thus is just a background annoyance, and feels impossible to solve. The underlying problem here is that things are hard, but from the inside hard and impossible feel the same, and they never try hard enough to see the difference.
My favourite solution to this is to get more creative - set a 5 minute timer to freely generate possible solutions and ideas, and see if things still feel impossible at the end of that. This works way more often than it has any right to. Often just telling people to do this can work, but it can also be useful to suggest taking 5 minutes right now to think about it (this depends on the weirdness tolerance of your friend, but can be super effective!)
Another approach - if you’re stuck, find a first step towards a world where you aren’t stuck any more. Often the best way to do this is to learn more about the problem - I call this gaining surface area. A few approaches:
I find that there is rarely a problem where the other person has genuinely tried all of the obvious ways of making progress!
It can also often help to ask for historical examples! Dig into the details of past examples of the problem and what could have helped then, and try to generalise this into a solution. Or, ask for an example of a similar problem they solved, and dig into what worked, and what could be applied here. It’s surprisingly hard to generalise from past experience without prompting!"
It’s all well and good to talk about the problem, but the main way a conversation can be helpful is by getting them to actually do something afterwards! Sometimes, at the start of the conversation it’s mutually obvious what the right solution is, and the real problem is one of procrastination, or a hidden aversion to implementing it.
I know that I personally have a much longer list of possible solutions to problems in my life, than I do of solutions I’m actually implementing. Failing to do anything about your problems is the default state of the world. And since they get no value without actually doing anything, one of the most valuable services you can provide is by fixing this!
This breaks down into two parts, breaking down the task into concrete next actions and creating accountability to support those concrete next actions
As a general rule, human intuitions suck when it comes to planning. We consistently over-estimate our conscientiousness and under-estimate how long things will take/how much we’ll procrastinate. We miss out on the obvious failure modes that’ll feel obvious in hindsight. Often I’ll be talking to somebody, and they’ll promise to do something afterwards, and it feels pretty obvious that they’ll forget, or are being too ambitious.
But, conveniently, this is much easier to fix when it’s explicitly pointed out, and you can force them to use the outside view! Two questions I love asking here (shamelessly stolen from CFAR’s Murphyjitsu technique):
I find these questions are really effective at getting them to actually leverage the knowledge and intuitions they already have and to make more robust plans. So I always ask them once we’ve formed a concrete plan, and this often helps make it more robust, especially for failure modes around procrastination!
Overall, I think these techniques have helped me to add a significant amount of value to my friend’s lives. And if you have friends who’d appreciate this kind of thing, I expect these techniques to be helpful!
I want to again emphasise the health warning at the start, not everyone wants you to solve their problems for them. I highly recommend explicitly checking beforehand! And I’ve very deliberately phrased most of these techniques as questions - if you get an unexpected answer to a question, that should be a significant update and worth listening to! And if you fail to listen to it, you are failing to be maximally helpful to your friend. Sometimes somebody answers “are you surprised if you haven’t done this next month?” with “yes, I’m just really busy this month”!
But if you can do this when appropriate, I think it’s a significant way to be a good friend and add value - I want to help all of my friends become happier, more agenty, effective and productive people, and think these techniques can work well for that. Good friendships should feel like a collaborative effort to make each other better.
And finally, getting good at giving this kind of advice can also be really helpful to your ability to solve your own problems! It’s way harder to recognise problems in yourself than other people (I think I only follow ~25% of my own advice), but it’s a learnable and valuable skill! And definitely one worth cultivating.
I strongly recommend Core Transformation as a framework for peer counseling. After trying a dozen different methods with dozens of people over the last five years it has been the clear winner.
Great insights into the human operating system here.
Very actionable; I love the brevity and being written in outline format.
Off-topic: I was reviewing some principles of classical rhetoric this morning; it's interesting how many I see applied in this piece.
Interesting, I'd be curious to hear more about which parts of this reminded you of classical rhetoric?