My Advice Checklist

Sometimes I write posts that end up being a point of reference for me often in the future. And sometimes, as with this post, I’m writing it specifically because I know I’ll want that reference in the future.

This is going to be a post I’ll show to anyone who wants to ask me for advice. If people frequently ask you for advice, feel free to copy this post and use it yourself!

The reason I want these things in an evergreen format is many of the questions I’ll put below can seem a little off-putting or even insulting if you think I’m asking them of specifically you and you alone, but are perfectly reasonable if you know that they’re just the baseline questions I always ask. So I’m putting them here in advance so I can prove that’s the case!

Okay, preliminary stuff out of the way. If I sent you this link, it’s because you asked to have some sort of meeting or conversation with me about some topic and want my input. If that’s the case, here’s the first thing you need to know: I don’t actually want to give you advice. I’m responding to a request and I’m happy to help, but this is me helping you. I wouldn’t stick my nose in your business if you didn’t ask, believe me – so don’t take anything as a personal insult.

The second thing I want you to know is that while I’m a generally pretty competent guy who has been around the block, I’m not some sort of universal expert or even particularly smart. It’s worth making sure that you actually want my input. Be skeptical! Confidence can be easily mistaken for expertise, and even with me you should be careful who you listen to.

Okay, assuming I haven’t chased you away from the idea of asking for my input about stuff, let’s get down to the things I’m likely going to ask in 99% of situations.

  1. After you’ve described an unpleasant or sticky situation, let’s examine the following idea: what would you do if you were literally the only human in the scenario who was capable of change? What would you do differently?
  2. List at least two ways in which you are the architect of the current situation. Unless a meteor fell from space onto your house, you had SOME input in getting here. I don’t want this to be accusatory – rather, I want to equip you with the insight to not have a bad situation repeat.
  3. What advice would you give to someone who was in a nearly identical situation, except they didn’t have any financial worries at all? How about if their situation was identical but they didn’t care about other peoples’ feelings? What if they had the same situation except they were invincible, immune from bodily harm? (Creating these “what ifs” can help isolate the real problem in a complicated situation.)
  4. What solutions have you already thought of and dismissed, or tried and failed? If the answer is “none,” then we’re not having the conversation we should be having.
  5. Lastly – do you want my advice? I know that seems like a weird question to ask this late in the game, but the reality is that a lot of people think they want advice and what they really want is to be listened to. And if that’s the case, I’m genuinely happy to do it – I’m a friendly ear whenever you need it, and not all problems need solutions; some just need friendship.

There’s a theme around these questions: personal responsibility. I’m a big believer in it, for one. But also it’s just a practical concern – I can’t really impact any of the other people in your story, so we have to focus on the brain in front of us, and that’s yours. You can see how some of those questions might feel a bit confrontational if I asked them right after you told me about an unpleasant problem you’re facing; they might feel like I’m exclusively putting “blame” on you or something. But it’s not that at all – it’s just that you’re the one I can empower.

Anything you do frequently, you should take the time to improve and make more efficient. If you spend a lot of time at a desk, it’s worth optimizing that desk for your comfort and efficiency. Similarly, I spend a lot of time advising (it’s my literal job, for one, but also the structures of my life and relationships just tend to run that way), so I want to make the process as efficient and effective as possible.

If you’re a parent, a manager, a leader of any kind, the go-to person in your social circles or family for practical advice, or any kind person who hears they phrase “hey, can I pick your brain about something” more than a few times per week, this same methodology can be very helpful for you as well. My goal is to give advice sparingly and thoughtfully, and to be considerate in my approach – if that helps you as well, then I am doubly glad.

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