The UnCollege Blog

When & How to Ask for Help


I believe in diminishing marginal returns. And because of this, I tell everyone who works with me that one of the most important things to figuring out how to work more efficiently is to figure out when & how to ask for help, etc.

Think for a moment, about the last time that you were stumped by a difficult problem. It could have been a coding challenge, it could have been a complex financial model, it could have been difficult copywriting, whatever. Think about it. Here, let’s define as “stump” as the point at which you’ve exhausted all the strategies you yourself have personally identified to try to solve the problem (e.g., you’ve Googled it, looked in online forums, tested different code variations, etc.). At this point, you have not yet reached out for help.

Now answer these questions:

  1. When starting the problem, did you think it may have been challenging enough to potentially stump you?
  2. How many strategies did you try before you got stumped?
  3. How long did it take you to get through those strategies to the point where you got stumped?
  4. How did you eventually overcome this stump?

It would be interesting to do a survey with the above but alas, I can only talk from experience. In my experience working with people, most of the time when they get stumped, they were not expecting it (i.e., answer to #1 is “no”). They felt they had the capabilities to fully tackle the problem in a timely and efficient manner. In my experience, people tried at least 3 strategies on their own, but often times more (especially it’s a code based problem, where there are various ways of coding something to try and get it to work). And, most importantly, most people worked on this one problem for 3+ hours before admitting they were stumped.

I believe this is an inefficient & frustrating way of getting work done. And yet, it happens all the time (to me too, despite my hyper self-awareness of it!). The reason is because we want the answer to #4 to be, “I powered through and did it myself.” We want to be proud of our own accomplishments, not having relied on others, especially not in a work context where reliance might come across as a shortcoming, a lack of skill, or something else we’re “dinged” for.

But, more often than not, the answer to #4 is that someone else helped us overcome the stump by making just the right suggestion, no matter how small. And, more often than not, we’re not judged as harshly as we think for getting outside help.

So my first point is: should you ask for help? Definitely!

Never be afraid of doing so & never let personal pride get in the way. Remember that asking for help clears roadblocks quicker and makes you feel a lot less frustrated. Some tips for getting yourself to be more open & willing to ask for help:

Fully understand the scope of a problem at the very beginning, and realistically assess your capabilities to see the fit. If you’re tasked to write a story and you’ve never written more than a few sentences before, there’s a real potential that you’ll find this task hard — even if it’s “just writing.” Being honest about when you might be challenged, before you even start, helps you avoid “stick it out” behavior. (As well, if you’re up front with you boss/ team about a problem that may stump you, they might allocate more time and resources, instead of expecting a solution the next day, which will only stress you out and frustrate you further once you get stuck!)

Remember that there is no ‘I’ in team. Your team members and boss are not out to get you. No one wants you to fail. So don’t think you need to do everything yourself — there is absolutely nothing to prove. And if you can’t believe that, then believe this: the more time you spend getting stumped, the more time you’re charging to your boss, who probably doesn’t want that. In other words, it’s even in the boss’ financial interest to help you get un-stumped faster.

If you’re convinced, now the bigger questions: when should you ask for help? and how?


Just because you should ask for help, doesn’t mean you should always do it first and foremost. If someone else had the answers, then there wouldn’t be any work to do in the first place! Rather, when you’re tasked with a problem, you need to give it some time and thought before getting stumped.

You need to spend long enough on the problem that you can grasp it. If I told you right now to solve climate change, your mind might go blank, or blow up with a zillion ideas all at once screaming for your attention so much that you might might as well be blank. You need to take the time to rein the ideas in and to render the problem into a structured approach. Visually speaking, think about turning that amorphous blob of ideas into a geometric shape, or think about building a blueprint for a house. For some complex problems, this process itself might take several hours of research!

Once you have the problem in the whole of your mind, then from that point, start your timer. As you brainstorm solutions, think about categorizing these more vs. less likely to solve the problem, and try the former group first. For example, to solve climate change, you might try marketing-based solutions first to address consumer demand rather than policy changes, if you believe that policy tends to deadlock itself and be diluted in its final form.

You should try at least 2–3 of the “more likely” solutions, at least. Now obviously for climate change, the time span is probably years. But for the average problem in you work life, doing this will probably take a few hours. At that point, if you’re not seeing progress, then it’s time to consider asking for help. Now, not only do you know exactly what the problem is, but you’re also armed with enough experience to answer questions such as “what solutions have you tried, why have they failed, etc.”

So to conclude, the second point is: ask for help once you have a structured the problem & spent a few hours trying a few potential solutions, which failed.

For me, that’s usually 1–2 hours before I ask for help. But of course, this will also depend on how important a question is, and how easy it is to find people who can help you.

Here’s a graphical visualization of what I’m talking about.



You know the popular meme: let me Google that for you? In case you didn’t,let me Google that for you. The gist: it’s annoying to get asked for help for something that’s super easy to solve. And that’s the other reason why you need to spend some time on the problem first.

If your helper can find a pretty easy solution on the first page of Google search results, they’ll probably be a little bit more annoyed and a little less inclined to help out (always, of course, depending on circumstance).

The final point is: when asking for help, include the following information:

  1. The problem you’re trying to solve. Do not make the other person go through the whole exercise to understand what the problem is, spell it out for them as well as any relevant context for the problem (e.g., why you’re working on this/ why it’s a problem; every once in a while, someone might realize that you’ve been tackling on an problem that’s not super important)
  2. The solutions you’ve tried and the detailed outcomes. Think about also including trade-offs — oftentimes each solution solves a bit of the problem but not the whole; what are the bits specifically? Maybe you’ll get some insight on combining them
  3. How you found/ came up with the solutions. As in the Google example, this is just to prevent the person from helping you by researching the same sources
  4. What other solutions you’re thinking of trying. Remember, at this point, you’ve reached out after working on 2–3 “more likely” solutions and spending 1–2 hours, but you could easily have other ideas that you haven’t tried yet. Offer up these suggests and see how the other person reacts

And that’s it! Hopefully, this gets you unstuck, and helps you to be a much more efficient at work!

Did you enjoy this post? Don't miss: If You Could Offer One Piece of Advice...

About the Author:

James dreams about a more sustainable future. His current project aims to reduce over-consumption--Last Minute Gear ( will rent & deliver outdoors gear (e.g., camping, snowsports) up to 1 hour before a trip!

This post was originally published on James' Medium Page

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