DGQ 8: What challenges are you facing right now?

tree, hand, help

How can I help you?

For those who spend a meaningful amount of time giving and helping others, that won’t be the first time you’ve heard that question. And it won’t be the last. On the flip side, if you’ve ever asked anyone else for help or advice, you most likely asked the above question yourself.

While it originates from positive intent, that question often falls short in execution.

  1. It is an open search query. Most busy people are context switching all the time. While we love spending time helping others, we don’t often think about how others can help us. I was asked this a total of 6 times over the past week, and I didn’t have an immediate answer for any of them.
  2. We force ourselves to think of an answer that isn’t always what we actually need.
  3. It shows you haven’t done your homework. I admit some people are more explicit with things they need help with publicly than others. Sometimes you’ll be able to pick up by inference, based on job title and time in their career.

Nevertheless, when you’re unable to find the answer to “How can I help you?” yourself, I default to figuring out what obstacles and challenges they’re currently facing. The question “What challenges are you facing right now?” is less of a question that is explicitly asked, but one of my main questions I need to get answered by the end of the conversation – no matter how long or short the conversation is. That said, there are fewer times than I can count where I felt compelled to explicitly ask someone I’m reaching out to help, “What challenges are you facing right now?”. I will admit I ask this quite often when catching up with friends.

So, what do I ask instead to find out what challenges the other is facing?

  1. Draw assumptions based on appearance and energy. “You look like you haven’t been able to sleep well for the past two weeks.” Then following up with, “What have you been losing sleep over?”
  2. Be willing to step up to the plate first. “I’ve been struggling with X this past week… Have you been struggling with anything recently?”
  3. Sometimes the best answers and insights you’ll get into a person’s life isn’t through just a single question. But rather, through just the flow of conversation. And subsequently, I don’t have any one-size-fit-all template to gauge that.

While I admit I’m still working on being able to close conversations well myself, being able to close a conversation is sometimes more important than the conversation itself. As Maya Angelou once said, “At the end of the day people won’t remember what you said or did, they will remember how you made them feel.” On the same token, the end of a conversation will determine the aftertaste you leave in another’s mouth.

Quite often, I find myself closing off with: “You’ve been incredibly helpful. We’ve completely run out of time before we ran out of topics, but I want to be cognizant of your time. I’d be remiss if I didn’t at least try to be the same for you.” And depending on the conversation, I’d subsequently follow up with either:

  1. “You mentioned X earlier in our conversation, and I would love to send you some amazing resources on that before the end of the day today.”
  2. “I noticed that you recently tweeted about Y, so to thank you for your time, I compiled a list of Y that would hopefully save you some time.”

Photo by Neil Thomas on Unsplash


The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.


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