How to Connect with People from the Inside Out

Have you ever felt inadequate to respond when someone has opened up to you about their feelings? I know I have. But after I get past the awkwardness, I always find the profound connection makes the discomfort worth it.


I had been working with Elizabeth (not her real name) for about six months. She joined the company with deep experience and high expectations. But recently, her work effort had been waning. A couple of big projects had fallen through, and then I heard from a colleague that she had been in a hard conversation with another person on our team. I let it all go without discussing it for a while. She was, after all, an experienced leader on our team.

I’ll never forgot when it finally all came to the surface—all of her anxiety, pain and frustration. We were in our bi-weekly one-on-one meeting when I asked, “So how are you doing?”

“Fine. I’m working on ABC client and XYZ project, and we need to get this, that and the other thing done by the end of the week.”

“Elizabeth,” [pause] “how are you really doing on the inside?”

“Oh, a little stressed and tired, but I’m really focused on getting this work out the door this week.”

[Pause with a soft smile and nod] “Say more about your stress and fatigue. How are you doing?”

At that point, her eyes welled up with tears and, as her lips quivered, she said, “Actually, I’m feeling really overwhelmed. I feel like I’m not my normal self. Sometimes I feel like I’m failing, and I am having a really hard time with a couple of work relationships…I’m sorry, I didn’t mean to cry.”

Well, I didn’t mean for her to, either, and now I’m somewhat freaked out about how to respond. Do I put my hand on her shoulder? Allow myself to cry with her? Console her with choice words of wisdom? Will she regret being this vulnerable with me? Maybe I should rescue her and wrap this up as quickly as possible?

“Elizabeth, thanks for being real. I’m sorry.” [Pause]

“I just want to be a valuable contributor to the team and feel like I’m doing work that fits my strengths.”


[Another pause]

“Yeah, I want that for you too. I’m sad that you’re feeling overwhelmed. And I’m glad that we can talk about what’s going on inside of you.”

That led to some ideas to support Elizabeth, but here’s the coolest part. Elizabeth and I were able to connect. We connected with each other, which increased our trust in one another. And she connected with herself, which increased her self-awareness.

Do you connect like that with people at work?

To connect, you need to discover what’s happening internally more than what’s happening externally. This means encouraging people to tell you more about who they are than what they are doing in the moment.

Consider the following questions. Do you:

  1. Reserve regular time in your schedule to be with people one on one?
  2. Meet with people in places and spaces that make it feel safe for them to be open with you?
  3. Suppress your own inner monologue of to-do lists and objectives in order to really listen?
  4. Genuinely inquire about what’s going on inside of someone rather than only outside of someone?
  5. Accept the awkwardness and internal discomfort that can come when someone reveals their emotions?
  6. Resist the temptation to respond with words of rescue, wisdom or solution?
  7. Follow up with people to ask how they are doing?
  8. Practice confidentiality so that people know that they won’t be hurt or judged by being vulnerable with you?
  9. Recognize that the most important “work” people need to do is work on the inside?

And finally, how about you? Who are you right now on the inside?



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  • Doreen Cropp
    September 28, 2016 at 4:46 pm

    I have recently encountered this exact situation, and unfortunately it did not result in a good departure. Never had a chance in this organization. Very good message. Thank you.

    • Matt Norman
      September 28, 2016 at 9:41 pm

      Doreen, thank you for commenting and I’m glad that the message resonated. It’s unfortunate that your recent situation did not end well. Hopefully your current or future organization will provide a better environment.