Introduction

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.

Giving Them Agency

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:

1. You need to follow a strategy that’s robust to having misunderstood something
2. You want to always feel like you’re on their side, and helping to empower them to solve their problems, rather than creating a sense of external obligation towards solving things they don’t really care about

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:

• Motivating them to actually solve the problem, or do the action we’re talking about - often people are annoyed about something, or feel a vague obligation to work on it, but don’t feel strongly motivated to really, intrinsically care about it.
• It’s often extremely helpful to make concrete both the costs and the benefits of the action - it’s easy to be put off by a gut reflex without ever really digging into it
• A common example: People neglect the value of information from trying something new, eg a new productivity technique that might solve their problem, but doesn’t feel quite right. Here, asking “what are the costs of doing this?” and “what would it look like if this went well? How could that change what you do next time?” can make this feel more visceral
• I think people have a strong systematic bias against taking cheap tests
• Another common example: Neglecting opportunity costs. Eg, somebody has an overloaded course schedule, and feels overwhelmed, but doesn’t want to drop any particular course. Because the cost of dropping it feels visceral, while all the other things they could do with that time don’t
• More generally, asking them to elaborate on the benefits, costs and risks of each action can make a decision much easier
• It’s easy to be loss averse, and fixate on the costs and worst case scenarios. I like to ask people to imagine something goes really well - say the 90th percentile of possible outcomes - and to flesh out what that actually looks like.
• Calling people on their BS (high variance!)
• I find that with a certain kind of person, it can be helpful to explicitly say that it feels like they’re complaining about their problems without really doing anything about them, and are just being passive
• This is definitely a high-variance one - I recommend only using it on friends you’re confident will take it well
• Overcoming insecurity
• I find that often the smartest and most capable people I know can be the most insecure, and underweight their own ability
• It can be really helpful to take the outside view, eg encourage them to apply for a job by asking how they think that company would respond to “generic person in their reference class” or “specific friend who’s similar to them on paper”
• Explicitly talking about all the ways they’re impressive helps a lot here
• You can also side-step this issue entirely, and frame something as a low-cost experiment, especially if I think their chance of doing well is way higher than they do
• I find people often respond well if I explicitly say I think they’re being insecure and under-estimating their own ability
• Overcoming inertia and fear of failure
• It’s easy to fixate on the risk that something could go wrong. Eg, they try something new, don’t enjoy it, and feel like they’ve wasted their time. It often helps to explore what failure would concretely look like
• It can also help to reframe things so that failure is still a success - eg, frame it as running an experiment for the sake of gaining information. A negative result is still a result, and running experiment to resolve uncertainty is an awesome habit to cultivate!
• More generally, I think one of the best ways to add value is to challenge their framing of a problem - that’s one of the hardest things to do yourself!
• More generally, framing an action as “becoming closer to the kind of person they want to be” can be shift from obligation to intrinsic motivation here
• Creating urgency
• It’s easy to procrastinate and put things off endlessly, because they’re never urgent. This is the planning fallacy. It helps to get them to take the outside view: “how long have you been putting it off?” or “how long did it take to complete last -thing in this reference class-?”
• Use pre-hindsight: “Would you be surprised if it’s one month from now and you’ve still not got round to it?” or “and you still feel too busy to do it?”
• Saying things in the first person
• A cheap, but surprisingly useful hack, is to describe what I think is going on in their head from my perspective, and ask whether that fits.
• Eg, if I think they’re procrastinating sending an email for BS reasons, say “I find that often I’ll come up with creative excuses to avoid sending an email, when really I just hate sending emails, and know I’ll need to get round to it eventually. Does that resonate at all?”

What to do when stuck

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:

• Ask somebody for advice, who has relevant experience
• Run a cheap test/experiment. Try something new and see what it’s like
• Take some time to introspect on what’s going on and what it feels like
• Do some research

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!"

Taking Action

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

• Have a concrete next step
• Always, always, always prompt them to concretely describe what they plan on doing next. In order to do anything, they will eventually need to convert intentions into concrete actions. But this is cognitive labour, and rarely feels urgent, so it’s always something that can be put off. But this increases the labour required to actually do anything in future, increasing the activation energy and making it easy to procrastinate. So making them do the labour now makes them much more likely to eventually do something!
• I think this is an incredibly important step, and worth being somewhat pushy on
• If you can ensure they do at least one thing towards the goal, they’ll build momentum and it’s much more likely that they continue
• One of the strongest sources of procrastination is when a task feels overwhelming and fuzzy - breaking out a concrete next action is the only reasonable solution to this
• It normally works to explicitly ask “what is the next step you can take towards this goal?”
• People are rarely concrete enough first time round, I recommend poking them for more detail:
• When will you do it?
• Press for the earliest reasonable time, motivation drops with time
• Press for a specific time of day, on a specific day, when they know they’ll be free - this makes it much more likely to happen
• Where will you be?
• What, concretely will the task look like?
• Will you need anything to do this?
• Interestingly, I find some people are way too ambitious here, other people aren’t ambitious enough - telling the difference is somewhat subjective, but I find nudging them in either direction can be helpful
• Getting more than one step planned can be even better! But this is often harder, and less necessary - often they’ll have a much better idea of step 2 after step 1
• Setting accountability systems - finding ways to make this concrete plan stick
• Getting them to set a concrete task, at a specific time, and putting it in their calendar often suffices!
• Encourage them to set reminders for that time, eg setting an email reminder or an alarm
• Creating social accountability - I offer to message them checking how it went at a specific time
• I recommend only doing this if you have a good reminder system that you know you follow! I currently set myself a Trello task with a due date
• I’m pretty excited about Telegram scheduled messages for this purpose!
• (Higher variance) Setting up some financial accountability
• I think this is interesting, works super well for some people, and badly for others. I recommend against pushing for it, though it can be a worthwhile option to suggest
• Websites like Beeminder and Stickk are popular for this, though I personally find them a bit too clunky for personal use
• I’ve recently developed a system for personal commitments where I message a friend a task and deadline, and commit to paying them £20 if I fail - this is shockingly low friction and effective!
• Open offer - if anybody wants to commit to sending me money if they haven’t completed a specific task by a specific time, I will enthusiastically keep track of this and follow up! :)

Good Planning

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):

• Measuring surprise: “Would you be surprised if it’s two weeks from now and you haven’t got round to it?”
• Pre-hindsight: “Suppose it’s 2 weeks from now and this didn’t work. What went wrong?”
• Eg, they want to make a new exercise routine, ask “Suppose it’s a month from now, and this routine hasn’t stuck. What went wrong?”

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!

Conclusion

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.