Helpful Questions to Ask Someone Having a Tough Time

having a hard time

There are three questions you can keep in your back pocket that will make it super easy to check in with someone having a tough time. Because That way, you won’t be at a loss for words–which is a big reason why we may be tempted to stay away when someone we know or love is going through something hard. We don’t want to say the wrong thing. These questions free you from having to figure out what to say, and help you keep the conversation focused on them and progressing in a way that they’re able to be present for.

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Here’s the first question: Want to talk about it? 

A lot of people are worried about ‘bending your ear.’ They don’t want to burden you. Or maybe they truly don’t want to talk about anything serious because they’re just not in the space to. 

BUT, everyone appreciates the opportunity to share what’s going on with them, even if they don’t feel like taking you up on it. 

A simple, “Want to talk about it?” is often all it takes to get someone to share what they’re ready to share. Once they start talking, it’s important to remember that your only job is to listen and to validate, meaning, to let them know that you’re listening without judgment. So you just want to say things like, “Wow, that sounds hard.” Or, “I can tell this means a lot to you.” You’re just mirroring their experience back to them, letting you know that you’re with them. 

And if they DON’T want to talk about it, you can simply say, “I’m here for you whenever. Is it OK if I check in with you about it again later?” And if they say no, or no thanks, or hell no, hey, respect their wishes. You tried. Just tell them that you care about them and you’re rooting for them. Just that knowledge can go a loooong way. 

The second question to ask is, How can I help? 

Really, it’s not your responsibility to fix or come up with solutions. You offer so much value just by being present and listening. But it’s also natural to want to help. Instead of launching into “I’m going to do this,” or, worse, “You know what you should do?” (I swear, I think those are my least favorite six words in the the English language), just say, “How can I help?” Or, slight variation, “How can I support you?” It can trigger the person to think about what they need, and just that nudge is powerful. Maybe they haven’t even thought about it yet. Of course, they may say, “I have no idea,” and that’s fine.

The third question to ask is “I have some ideas that might be helpful–want to hear them? Or want me to just listen?”

And it really is one of the last questions you should ask, because really your main job is just to let them know you care and listen to what they have to say, which is what the first two questions are designed to do. And it is:   

I know you’ve gotten unsolicited advice at some point in your life. And how did that feel? No matter how good the advice may have been, I’m guessing it made you feel not great. 

When you ask someone if they’re interested in your ideas and they say yes, it completely shifts the energy of the conversation and makes it a much more open dialogue. 

Another way to phrase this is, “Would you like some help brainstorming some ideas?” You don’t need to be the source of the thing that helps them through. I’ll talk more about this in Friday’s episode, but for now, just know that IF you have advice or help to offer, you want to ask first if the person is interested in hearing it. Just trust me on this. 

Remember how powerful it is just to listen – and if you need reminding of that, go back and listen to yesterday’s episode about bearing witness. So if they decline your invitation to help, just know – you still helped!

Daily Tiny Assignment

Your tiny assignment is jot down somewhere, maybe a note in your phone, or in your journal, these three questions: 

Want to talk about it? 

How can I help? 

And if they say they don’t know, you can follow that up with:

Would you like some help brainstorming ideas? Or, I have some ideas, would you like to hear them? 

I hope you’ll come back tomorrow, when I’m interviewing somatic psychologist Dr. Susan Bernstein about what NOT to say to an anxious person. 


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