The best question you could ask the people you care about

April 19, 2024

Discover how this one simple line of questioning can help you build deep trust and understand the people you love and care about. This works both at work and also in your personal life.

The best question you could ask the people you care about

Not too long ago, I was working through a tough situation between various leaders in an executive team I coach.

It was one of those days where nothing was going according to how I thought it was going to go. It turns out, humans are irrational beings with big emotions, and my job as a facilitator is to hold space for that. Some days are harder than others. This was a particularly hard day.

In a moment of panic and distress, I called one of my best friends, Sabrina Wang, who also happens to be an executive coach. Without divulging sensitive details to her, I shared with her how crappy and out of control I felt that day. I was scared that I would never be able to help the leadership team, and it left me distraught imagining the team’s tensions growing even more explosive.

Sabrina then taught me one simple notion in two different ways.

First, she said, “Hmm, this sounds like a lot. My question for you right now is, what do you need? Would you like empathy and compassion, or my thoughts on how I would approach this situation?”

Obviously, I asked her for both.

This was effective for two reasons. First, if Sabrina offered only empathy and compassion, I would have felt better for a little bit — but I would still feel alone, solving hard problems all alone.

Second, if she jumped straight into telling me how she would solve this problem, I could have gotten triggered. My fear brain might have said, “What, does she think I’m an idiot, that I don’t know how to solve this? Also, how stupid am I that she’s suggesting things I never thought of?” In other words, I would have felt completely unheard, like she didn’t understand what I needed.

Instead of assuming, Sabrina asked. Her simple question, “What do you need?” Along with options for me to choose from helped me feel at ease, like she was here to guide me, and also hold space with zero shame or stigma for my big emotions.

If that’s where the story ended, that would have been amazing. But like I said, Sabrina taught me this simple notion in two different ways. Here’s the second way.

After acknowledging my feelings of distress, she got my permission and told me what she would do:

“I would ask your coachee: how can I support you right now?”

Such a simple notion - who would have thought?! Ask someone: what do you need?

And this is where Sabrina was so clever: she not only explicitly gave me actionable advice, but she also practiced what she preached and I saw its results in real-time.

First, she asked me: “What do you need?”, which helped me see her advice in practice.

Then, she gave me the advice: “I would ask your coachee, ‘How can I support you?’”, which would help them think, “Yes, she is on my side, and she supports me - all because she cares!”

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Too often, we find ourselves assuming what the people around us need. It’s usually because we see the world through our own point of view, so we naturally offer people what we ourselves would want… even if they’re completely different people with different needs, wants, and desires.

We offer the (often unsolicited) advice to others thinking, “Well, I’d want someone to tell me if I were in their shoes!”

But what we forget is that when we dish out our advice, we are in a neutral state of mind, while the other person is likely in a highly-emotional, volatile emotional state.

You tell yourself you’d want unsolicited advice no matter what, but that’s your logical, untriggered brain talking. Your answer would likely be different if you were given unsolicited advice in a massively triggered state.

So don’t assume. Ask them what they need.

Asking for what they need aligns you to them. It reminds them: “I’m on your side. I’m here to support you. I am not the enemy. I am here to help.”

Here are a few prompts that you can try on for size:

  • How can I support you right now?
  • What is it that you need?
  • What’s the best way to hold space for you?
  • I’m a container for you, and want to be here for you in whatever way feels good for both of us.

Once you ask what they need, you’re not done. Offer some options.

Highly distraught or emotionally triggered people can’t think straight, and giving them open-ended questions my cause them to feel further distress at not being able to fully articulate what it actually is they want.

You can do this a few different ways:

  • Here are some ways I can help you that come to mind …
  • I think these are the ways I can support you … what sounds good from that list? And of course, if there’s anything else I didn’t mention, I’d love for you to tell me.
  • Would … help? Of course, we don’t have to go there if it’s more distressing than supportive.

Once you figure out your most authentic narrative to (1) ask for what they need, and (2) suggest a few options, your final task is to stick to what they have asked you for and give nothing more, nothing less.

That means, if they ask for you to only hold space for them, please don’t start offering advice after you hold space for them. You may only offer advice if they’re no longer triggered and feel adequately heard. Do this any sooner, and you’ll unravel the safety you helped them feel and all the trust you’ve just built with them.

Support them as they need, and if you’re done with that, ask them: Is there more I can do to help you?

They will tell you what they need, hopefully in a less triggered state.

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Ever since Sabrina gave me this sage advice, I have implemented it in multiple facets of my life.

I always ask this question and validate emotional experiences.

In conflict resolution.

During coaching sessions.

While listening to friends or colleagues that are hurting.

It even works with kids. Recently, I was talking to the high school daughter of a very close friend, who was heavily distraught because she had been bullied earlier that day by her peers.

Instead of assuming what she needed or freezing in paralysis talking about sensitive and triggering topics, here’s what I did.

  1. I validated her feelings. “Hey, I’m incredibly sorry that that happened to you. It’s fucked up and should never have happened. I can’t imagine how violated you felt, and how much trust dissolved between you and this supposed friend.”
  2. I asked her what she needed. “My question for you right now is, how can I support you?” 
  3. I gave her some options. “We can talk about it, we can stand here and eat ice cream, we can hang out and do something else… what sounds good to you?”

From there, she replied that she would simply like to spend time together. So we sat on the couch, ate ice cream, and hung out in silence. In the end, she felt better, and trust was created at a deeper level.

Before leaving, I reminded her (with her parent’s permission, of course) how else I was willing and happy to support her.

I told her, “I am a trusted family friend, and you can text or call me any time.” She nodded, thanked me, we hugged, and I went on my way.

To continue with trust building, I would not make a promise I could not or did not want to keep. So my intention is to fulfill this offer - if she texts or calls me, I will be there for her.

Try this out with your spouse, partner, child, colleague, or co-founder. The results may surprise you.

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Special thanks to Sabrina Wang for sharing her wisdom and allowing me to tell this story. Sabrina is the CEO of Evergrowth Coaching for extraordinary leaders of Series A to Unicorn companies.

Before starting Evergrowth, Sabrina was the Head of Coaching at Mochary Method, founded by Matt Mochary. Sabrina is well-versed in the engineering, product, and design side of building a tech company. At Headspace for Work, she worked in product management building B2B SaaS products that reached 1 million users.

Sabrina is driven by her mission to help people achieve high performance and find greater impact. Her coaching is heavily influenced by her mindfulness meditation journey, studying Reiki, energy work, and other spiritual modalities.

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Regina Gerbeaux

Who’s Regina Gerbeaux?

Regina Gerbeaux (@_rpgbx) is the executive coach to some of the fastest scaling startups in the world. She is also a founder currently interested in the food delivery and logistics space.

Regina was the first person trained by Matt Mochary (executive coach to the CEOs of Coinbase, Brex, and many more) in the Mochary Method Curriculum.

Her tactical templates and operational write-ups have been referenced and used by fast-scaling companies, including BioRender, CoreDB, dYdX, and many more.

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