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Hi! I’m Irene. I’m one of the people supporting the Diamante Scholars program. If you’re part of the program, there are good odds that we’ve met. If we haven’t met – then thanks for checking in with us, and I’m happy to get to introduce myself to you. I live in Seattle, am currently doing a ton of baking, and am tackling some really big problems that I didn’t see coming a few months ago. Tackling big, difficult problems can sometimes feel like an unsolvable maze. It doesn’t have to be that way, even though it feels that way. I often find that it’s a matter of breaking that big problem down into smaller, more easily managed problems, and then figuring out what information I need to start solving those smaller pieces.

For me – the effort of turning ambiguous, challenging problems into small solvable ones relies on all of my sense-making tools, most useful among them is leaning into the ability to ask what I think are some pretty basic, possibly very dumb questions.  It’s humbling, but asking yourself questions, and figuring out answers is simple, and important. 

By taking the big problem, turning into smaller problems, and then figuring out what kind of information is needed along the way, you can derive a list of questions that – as you answer them – help you learn how to build a solution. 

Have an objective

First, make sure you understand what problem you are trying to solve.  For example – suppose you’re worried about how you’re going to afford college. Do you want the scope of your problem to be: “I’m worried about how I’m going to pay for tuition and supplies”, or is it more appropriate to specify it as “I’m worried about how I’m going to pay my room and board, plus the cost of my education.” 

Part of specifying a problem is having a high level expectation of what a good outcome looks like. In our above example, you could pay nothing for school by simply not going. That’s not a very good solution. A better solution to the problem is one where you know how you will pay your tuition, you feel secure in your housing, and you have a plan to pay for books. This is your objective. 

Set expectations for the answer

Objective in mind – do a quick check in with yourself about what you expect – the concept of what a good answer looks like to you. Having a sense for what sort of answer you think you need can help you figure out how to ask follow up questions. It also helps sort the helpful answers from the non-helpful answers. 

Suppose your problem is that you have to learn to drive a car. Then your objective might be “being able to get in the car, and safely drive it from point A to point B.” If you ask someone “how do I drive a car?” and they respond by telling you about how combustion engines work you can quickly see that they’ve misunderstood the question. They’re telling you how the car works, not how you operate the car. If instead they tell you about the laws and rules you have to obey while you’re driving (all important things) – they’re telling you about how drivers operate in society – again, this is not how you operate a car. An answer that tells you about the function of the ignition, how to use the steering wheel, what the instrument panel means,  is telling you exactly what you needed to know. 

Evaluate the answer honestly and objectively: 

There are all kinds of answers that you can receive in response to a question – and the bigger, more complicated and more open ended the question is the more different kinds of answers you are going to get. Suppose we’re answering a math problem. If the question is “how do I solve this EXACT problem?” – there’s generally one right answer, and a couple of different ways to go about finding it. If the question is “how do I solve math questions of this type of math problem” the right answer is less specific, and so on up the chain. 

Evaluating any answer you are given takes time and work, and it can really help to be organized. 

  • Write down the critical points of the answer. If you have the opportunity, repeat it back in your own words to be sure you understand. 
  • Check in with the usability of the answer. Look back at your objective. If your original goal was to better understand a complicated system then ask yourself – does this answer allow me to ask more specific questions, define next steps, or take a specific action? 
  • Check in with the content of the answer. Does the answer make specific claims about the way the world works, or expectations you should have? Can you verify those claims independently? Even quick “gut feeling” checks for whether or not the answer someone gives you makes sense can tell you whether you need to ask a follow up or dig deeper. 
  • Evaluate the level of risk if you act on bad information. Following math tutoring that taught you how to solve a derivative incorrectly might cost you a few points on a test, but that misunderstanding is also really easy to fix. In this case, bad information is annoying, but not life altering. However, making an important financial decision can have long term consequences and lots of different payoffs, and in this case your standard for action is a lot higher. 
  • Sometimes people give you extra information, or give you an answer that doesn’t seem to match the question that you asked. There are a lot of reasons for this, but regardless, they took the time to share with you. So evaluate it. Can you use that information elsewhere? Does it tell you something about the world that you didn’t know before? Does it change how you think about your original question or objective? 
  • Do you need to revise your question? If the answer you got doesn’t quite allow you to figure out what to do next you need to reflect on how to ask a better question and go back to the start. This is ok – it’s an important part of asking questions, and the more complicated the topic the more likely this is the outcome. It can seem frustrating at the time, but it is meaningful progress. 
  • Separate the information content from the delivery. There are specific instances when this is critical to fully evaluating the answer.
    • When the person answering the question appears to be an expert. Just because someone says something in an authoritative way does not make them an authority, and even if they’re an authority in something that doesn’t mean they’re an authority in the thing you’re asking about. 
    • When the information is good, but the delivery is bad – like when someone answers your question but does it with a bad attitude, or as if you are a nuisance. Writing down the information and evaluating it outside of the interaction can help you see that the answer you got moves you forward, even if the interaction didn’t feel great. 
    • When the information is bad, but the delivery is nice. Just because the way information is presented makes you feel good, doesn’t make it true or correct. 

Remember: questions are innately human

Don’t be afraid to ask questions, but do be cautious about whose advice you take – including mine! In general, people like to help, and asking a question is the first step in allowing them to do so. In order for them to genuinely help, your counterparts might need you to be a little flexible with them. By listening to people without interrupting, accepting answers that are formatted a little differently than you originally expected, or iterating on the question and answer until you fully understand – you are much more likely to get meaningful information. 

Asking questions is a big part of how we build relationships – relationships to institutions, society, and each other. Because questioning, and learning is so intermingled with just being human, it can be a little messy.  Be kind to the people who are willing to try to answer your questions, even when they fail. Even when they don’t answer your question, or they do it in a grumpy tone of voice, thank them for however much they showed up for you and keep on moving down your path. You aren’t obligated to act on every answer given, and you’re going to find that you sometimes have to ask the same question a lot. 

When all else fails – the right question is to find someone you trust and ask them “I don’t know what I’m doing, but this is my goal. Can you help me figure out where to start.” If you just do that the rest of the questions will come.