The Problem

When someone shares something big and painful, the pressure to find the perfect words in response is heavy, isn’t it? The inner critic kicks in, whispering, “What if I say the wrong thing?” “What if I make it worse?” “I should have a solution, but I don’t.” And just when you think you’ve figured out the right thing to say, the inner critic pounces again: “What if they think I’m not helpful?”

As leaders, we’re trained to solve problems. In moments like these, the instinct to fix is strong. It’s a struggle I wrestle with, too. But sometimes the real work is simply being present. So, what do you do when you don’t know what to say? How do you show up as a leader when you can’t solve everything?

The Discovery

From personal experience sharing big, painful things with others, I’ve learned what kinds of responses don’t work for me. I get the internal wince when someone tries to "fix" or rush me into feeling better. I think, yeah, that’s not quite what I need right now. After spending hundreds of hours facilitating experiential communication courses at Stanford Graduate School of Business, I found relief and validation when I discovered what doesn’t work for me often doesn’t work for other people. So I’d like to share with you five very human urges I’ve noticed (both in myself and others) that miss the mark and hurt your hard conversations:

1. The Urge to Fix

It’s so easy to fall into the trap of solving everything. We’re wired to offer advice and solutions. It’s tempting to say things like:

• “Have you tried doing this?”

• “You should talk to so-and-so—they might have the answer.”

• “I’ve been through something similar, and here’s what I did…”

I am certain your advice comes from a good place, but sometimes a person needs to be seen before they need a solution.

2. The Urge to See the Bright Side

Another instinct that sneaks in is the urge to find the silver lining. You might say things like:

• “At least it’s not as bad as it could be.”

• “Everything happens for a reason, right?”

• “You’ll laugh about this someday!”

When I hear one of these after I share something big and painful, you know what goes on in my head? “I get to say that, not you.” Rushing to optimism with a reframe before the person gets there themselves is exactly that, rushing. If you have felt rushed, you know it’s not great. 

3. The Urge to Be The Cheerleader

You want to help them snap out of it, feel better, see their worth, and get back on their feet. You might feel the urge to be their personal cheerleader, saying things like:

• “You’ve handled worse before!”

• “Look how much you’ve accomplished—you’ll get through this too!”

• “I believe in you! You’ll bounce back stronger than ever!”

While this comes from a place of care and wanting to see them rise above the situation, it can feel overwhelming to someone who is simply trying to process their emotions. 

4. The Urge to Be The Detective

Sometimes we ask questions about the logistics or the details of what happened. When we do, we prioritize our understanding over their feelings. 

• “What exactly happened?”

• “What did they say next?”

I know a couple who struggled with IVF and the main way people responded was asking, “When’s the next procedure? What did the doctor say? What happens if this time doesn't work?” The hardest part wasn’t coping with the uncertainty of the process – it was constantly answering the peppering logistical questions they received.

5. The Urge to Be Silent

Sometimes, we go quiet because we don’t know what to say and we think staying silent is the safest option. But when you stay silent too long, it can lead them to think, “Maybe I shouldn't have shared this. It's too much for them.” or “They probably think I'm overreacting or being dramatic.” Instead of helping them process, your silence creates more doubt and isolation.

When a big, painful thing happens to me, my inner critic can take hold and spin up a story that I didn’t do enough. As a result, I’ll share something like, “Gosh, I’m a dumb dumb.” (but likely in harsher words)

When that share is met with silence, I think whoever I’m talking to must think I’m a dumb dumb too.

This might seem like a long list, but what all these responses have in common is they don’t soothe the hurt, they run past it or ignore it. So, what works better?

The Experiment

I learned that what I really need when I share something big and painful isn’t advice or cheerleading—it’s connection. Here are a few ideas from my coaching practice that shift the focus from “What should I say?” to “How can I connect?” in the moment of the big, painful share and after.

In the Moment

1. Your Feelings
   When someone shares something hard, sometimes the best thing you can do is simply share how you feel about what they’re going through. Letting your emotions show humanizes the moment and validates their experience. For example:

• “I’m so mad that this happened to you. That’s just not fair.”

• “I’m heartbroken for you. I can’t believe you’re dealing with this.”

This response shows that you’re not just hearing their words—you’re emotionally with them. It’s a simple but powerful way to connect.

2. Your Observation
   Sometimes, it’s not about your feelings but about what you’ve observed. People often feel deeply valued when someone recognizes their strength, dedication, or passion, especially during tough times. For example:

• “You really loved that house. I can tell how much it meant to you.”

• “You worked so hard on this project. I can see how much you’ve invested.”

This shows you see their emotion, you see their values, you see them. 

3. Your Relationship
When words fail, sometimes the most powerful thing you can do is simply let them know you’re in their corner, no matter what. For example:

• “I just want to be here for you right now, no matter what you need.”

• “I don’t know what to say, but I’m with you through this.”

This type of response assures them that they don’t have to go through the chaos alone. 

After The Share

It’s easy to think that once you’ve said something, you’ve done your part. But following up to your initial response is a wonderful way to connect and show your care. Here’s why:

1. Give Clarity

When someone shares something tough, they’re often feeling overwhelmed, and the last thing you want to do is put the burden of next steps on them. For example:

Instead of saying, “Take as much time as you need,” give them some clarity about what happens next:

• “Take a few days, and then let’s check in on Wednesday to see how you’re doing.”

• “How about we talk again after a week, just to see where you’re at?”

Instead of, “Let me know what I can do,” give them some options:

• “I can watch your pet or your kids while you attend or plan services”

• “I can bring over a hot meal or do laundry”

This way they have some clear choices, making it easier for them to ask for what they want. 

2. Keep the World Going

When I was going through a tough time, what I needed most was to remember that the world was still spinning. Yet I noticed a lot of quiet after people’s initial care and condolences. I get it—their inner critic says, “Am I allowed to talk about my bad night of sleep when you’ve just had a huge loss?”

At least for me, it’s tough to keep talking about the big, painful thing for too long. I have to talk about something else. I want to tell you that I only recently started listening to Chappell Roan and, oh, I’ve been missing something good. I want to show you a tranquil wallpaper I found that calms me down. Or show you the muffins I made that taste better than they look, I promise. I want some normalcy. 

Sometimes giving people space can worsen the isolation. In the spirit of care and connection, take small actions to show you’re thinking of them: 

• “By the way, I think you’d love this song. I heard it today, and it totally reminded me of you.”

• “I was thinking of you this morning. Kiddo has been sick and crying for days. I don’t know how you do it with two.”

This helps to check-in, keep the connection, while maintaining normalcy 

3. Give Grace

Processing a big, painful event doesn’t happen all at once. For me, it might hit when I’m driving to Trader Joe’s a week later, and suddenly the reality of it all sets in—cue the sobs. But even when the big emotions aren’t showing, I know my mind, heart, and body are still processing. I notice it because I’m slower. I’m more tired. And sometimes, when I’m less regulated, I start to look for a fight. Not my best moment, but it’s true. I can come off as combative, even when I don’t mean to.

This might be true for you or the people around you as well. So, give grace—especially when someone isn’t at their best. The inner critic will try to tell you that they’re just being difficult or that they “should” be handling things better. But remember, there’s often a lot of unseen work happening beneath the surface.

The Takeaway 

The inner critic thrives on discomfort. When someone shares something big and painful, the inner critic may show up for you and the person sharing. To help quiet both your inner critics, remember your role is to listen. The real power of connection comes from showing up emotionally—not because you have all the answers, but because you care.

2. The Goings On

“Overeager Jen, here we go again!” is my playful mantra whenever I find myself taking on too much. I’ve lost count of how many times this has happened. While I’m better today at pacing myself, the growth I’m most proud of lies in how I respond when I overextend. In the past, I’d berate myself, which clouded my thinking and slowed my ability to figure things out. Now, with that phrase, I bring some humor into the situation, keep my head clear, and move forward.

What does this all mean? It means I am starting a waitlist and taking new 1:1 clients starting in April. If you are interested, reply. If you know someone who might be, pass this on!

I’m back facilitating Interpersonal Dynamics, Stanford Graduate School of Business' most popular elective on building effective professional relationships. In the very first session, I was reminded of something I love about this course—it helps students discover what they truly want and ask for it. (Sound familiar?)

This weekend I’m facilitating Building Interpersonal Skills, which takes some of those same concepts and opens them up to the public through Stanford Continuing Studies. The course is once again sold out with a waitlist. If you’ve signed up, I can’t wait to meet you.

In the world Executive Education, I’ve returned to facilitating Communicating With Impact at Stanford. I’m working with senior leaders around the globe to become savvy communicators who can get things done.

I mentioned late last year I’m cooking up a group coaching program. If you know me and my process, you know I’ve been doing lots of user interviews and experiments so I can make it an experience my one-year-old would say, “Wowww” to. (It’s her new favorite word).

____________________________________