What is your topic?
Insecurities – things that made you anxious or scared
What was your life like BEFORE you addressed this issue in your life?
Early in my career, I was all about being the most prepared guy in the room. I knew the products well: the numbers, the fine print, etc. I figured that was enough to earn trust. And meetings were fine, technically, but I could always tell something wasn’t sticking.
What emotions were you feeling BEFORE you dealt with the issue?
A lot of self-doubt, honestly. I had this mentor who could connect with just about anyone. He always made it look very natural, and I’d be standing there thinking: is that something you’re just born with? Then I’d try to do what he did and it would come out totally stiff. That was probably more frustrating than the original problem.
How was this issue affecting your life?
At work, my conversations with clients stayed shallow. People respected what I knew, but I don’t think they felt like I actually cared about them specifically. And it wasn’t just work. I did the same thing with friends and family. Always redirecting to something useful or productive. Like I didn’t know how to just let a conversation be a conversation.
What primary strategy or practice did you implement to address the issue?
I started making myself ask one real personal question per conversation, and then actually listening to the answer instead of already thinking about how to get back to business. I started sharing things about my own life first, which felt uncomfortable. And I basically had to reprogram myself to stop treating small talk like something to just get through.
Where did you hear about this strategy or practice?
I learned it entirely from watching my mentor. He never sat me down and explained it. I just started paying closer attention to what he did differently and tried to copy it. Badly, at first.
Please provide our readers with the individual strategic steps you took.
1. When you feel the urge to steer a personal moment back toward business, just pause. Don’t act on it yet.
2. Ask one real question you don’t already know the answer to. Then actually wait for the answer, don’t half-listen.
3. Share something true about your own life before asking someone to share theirs.
4. Let the conversation go wherever it goes for a little while. Resist the urge to steer it.
5. After each conversation, be honest with yourself, were you actually present, or just going through the motions?
6. Repeat this consistently, especially on the days it feels unnatural.
How long did it take before you saw or felt changes occurring?
It took longer than I expected. Over a year before it stopped feeling like I was performing it. There was no big turning point. Just gradual, meeting after meeting.
What challenges did you face along the way of your personal transformation?
Plenty. Awkward conversations, meetings that fell completely flat. I’d leave and replay it in my head for hours, wondering if I was just not cut out for that part of the work. Even though technically I was fine at everything else.
How did you address those challenges?
I kept showing up instead of retreating, which is honestly always what felt safer. I’d go back to watching what my mentor did and just remind myself that doing it consistently was more important than doing it perfectly.
What is life like for you now?
It’s just a different experience. Conversations with clients actually feel real now, not like something I’m managing. I’m a lot more comfortable being honest about who I am, including when I don’t have the answer. Having a kid recently changed my perspective too. You can’t fake presence with a toddler. It either matters to you or it doesn’t.
From a broader perspective, what you have learned about yourself through this experience?
Mostly that I was wrong about what connection actually is. I thought some people were just built for it and I wasn’t. Turns out it’s more like a muscle. You build it by using it, even when it feels awkward. Especially when it feels awkward.
What advice would you give others facing this challenge?
Just accept that you’re going to be bad at it for a while. There’s no shortcut, no one technique that unlocks it. You just have to keep showing up and being a little more real each time, until one day it stops feeling like something you’re doing and just becomes how you are.
What continues to give you strength?
My family. Becoming a dad has been the biggest thing. It puts everything in perspective pretty fast. You stop overthinking whether you’re connecting the right way and you just do it. That carries over into work more than I expected.
If others reading this would like to connect with you to ask questions, are you open to that?
Yes, I’m happy to connect with readers who have questions.