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Asking for help when you don’t even know what to ask

Five months ago, I embarked on a glorious adventure, the next step in my technical development with a new team at Microsoft. You could have almost seen the stars in my eyes as I daydreamed about what would surely be nonstop learning, rapid advancement, and the future of an all-star developer in the making. I would understand everything with confidence by my first month on the job, and everyone would love me. It would be awesome.

Well, here’s what actually happened. I made exactly zero check-ins my first month on the job. I caused a live site bug within the first three months. Now five months later, I’ve finally managed to claw my way up to the point where I feel reasonably competent, most days anyway. I’d like to think that people still love me, but I haven’t tested this theory yet. Anyway, say hello to reality!


These days I still sometimes have trouble figuring out how to approach a foreign problem. The common advice is to just ask for help. “Just ask! It won’t hurt!” they say. Hey, it’s solid and actionable advice, and so “just ask” I did!

Me: “Hey, can you explain how this works?”

Coworker: [Says a bunch of things I don’t understand]

Me: “Okay, thanks.”

A few hours later after doing some standalone investigation – because I was too embarrassed to admit I didn’t understand the first time – I make a bit of progress but get stuck again. I go back.

Me: “So found this other thing. What’s that?”

Coworker: “Um yeah, I already told you.” [Proceeds to explain again, but I’m having trouble listening over the sound of my shame.]

By this point, I sort of know what I’m doing and continue investigating on my own to fill in any remaining knowledge gaps, praying that I don’t have to go back and make a fool of myself some more. The day ends with me making embarrassingly slow progress.

Want more awkward responses?

“It’s not as complicated as you think.” <– My first month.

“What are you talking about?” <– Just a few weeks ago, when I was trying to ask about something by using a name that referred to something else.

And my personal favorite: No words, just the furrowed-brow, pursed-lip expression. You know, the kind where you can almost hear the gears grinding in the person’s head as they try to process what it is you’re even trying to say. <– Way too frequently to count! It’ll probably happen again tomorrow.

The problem wasn’t so much that I couldn’t ask questions as that I was so lost to the point that I literally had no idea what to even ask. The best I can come up with was “How does this [really broad thing] work?” which is a terribly generic question that puts the responder in a perfect position to return an equally generic, ambiguous answer. What you really want is a precise, context-specific answer that effectively unblocks you from what you’re trying to accomplish.


I just want to get from point A to point B, so how do I ask for help when I don’t even know what I need help with? I don’t know for sure, but after breaking down my core roadblocks, I have some ideas to implement.

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I’m so lost I don’t even know what questions to ask to unblock myself!
State anything that I do know! My one goal is help the other person understand exactly what pieces I already have so they can at least figure out which pieces I’m missing. I can only do that by being as specific as possible. State where I’m starting at and what I’m trying to accomplish, even if it’s something as simple as “I don’t know what this graph means, but the desired goal is to get it to look like it did at some earlier point in time.” What is point A and what is point B? Just start with those.

State exactly what I am currently doing. It may be completely off in the wrong direction, but it will at least help the other person understand how he or she can course correct me back onto the right path. You can’t course correct someone if you don’t know where they’re off-roading in the first place.

Be aware of terminology that keep popping up that I don’t fully understand. These terms appear in meetings, emails, hallway conversations, and you’ll know what they are, because every time you hear it, you’ll think “seriously, what the hell is that?” Now while it’s a good idea to just ask for the definition (this should be the default anyway), for bonus points just toss them into questions and see what happens! If I use them incorrectly, somebody will (hopefully) correct me. They will understand what path I’m trying to go down and course correct accordingly. I’ll also understand those terms better in context next time. It’s surprising how much frustration and blockage can result from simply not understanding how one word is used.

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I don’t know who to ask!

This is pretty simple (simple, not easy). Start with literally anyone & ask if they are familiar with the area in question or know someone who does. Eventually I should be able to daisy chain my way to the right person. Sometimes though, what you think is the right area turns out not to be what you’re actually looking for. Once again, it’s helpful to state the point A and point B if not really sure.


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What if I need to ask the same question twice because I didn’t fully understand the first time?

Then ask again! But for both my and everyone else’s time’s sake, I don’t actually want to rehash the same thing over and over again when I probably only forgot or failed to grasp one particular part of the original explanation. In that case, I intend to be honest and state what exactly I do or don’t understand so that the other person doesn’t waste time spending 80% of the time explaining what I already know and only the remainder of the time clarifying the actual area of confusion.

Here’s my template:

“I know I already talked to you about ___ , and I’ve gotten started doing ___, but then I forgot how ___ gets me to ___. How do I get started on this next part?”

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But I’ll look dumb!

“There’s no such thing as a stupid question.” “There’s no such thing as a stupid question so long as you believe it.”

You may choose to perceive a question as legit and someone else may choose to perceive it as dumb. Stupidity, like most self-attributing adjectives, is subjective. So yes, you may ask someone a question, and that person may judge you for it. I see no reason to sugar coat this reality. Most people will be happy to help you, but there are a rare few who will judge you. Oh well.

Feel embarrassed, awkward, or angry. Then set those feelings aside and remember the important thing: Did I get my answer to the right question? If the trade-off is between a temporary butthurt ego vs the knowledge acquisition that will unblock myself in favor of progress, which one’s more worth doing in the long run?

If the urge to process the torrent of emotions arise, I tell myself “I’m pretty [butthurt, pissed off, embarrassed, etc.] right now, but I’ll let these feelings go at this time and focus on the information I’m after. No worries, because I’ll have plenty of time to continue feeling [butthurt, pissed off, embarrassed, etc.] later.” Chances are, when “later” comes, I won’t feel nearly as bad as I would have while in the moment anyway.

One of my great life goals is to get comfortable with feeling “dumb,” and I’ve put several experiments into practice already. I’ll explore them more in future posts, but one simple practice right now is to just write down all the moments where you feel foolish. Look at that list a few weeks later and notice how you feel about those same moments now. Do you still feel the same way? Did you even remember some of them? Chances are that they suddenly appear a lot more trivial the second time around.

My challenge for the next few weeks is to ask specifically for what I want as soon as I notice the discomfort of “not knowing” arising. My responsibility is to help the answerer understand what it is I need. With that, I leave you with one of my favorite quotes, because who doesn’t love snazzy quotes?

“Choose discomfort over resentment.” — Brene Brown

Happy Asking!

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  1. I love Brene Browns work! Don’t lose track of the possibility that the other person may not be explaining things well, or that they may not be answering within a context that makes sense to you. Communication encompasses so many facets and is so complex. I think your idea of specificity is very good.

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