How I Learned to Have Tough Conversations
There’s a few feelings we can all relate to: the horror that ensues after a newly-purchased ice cream slides off its cone onto the ground, the disorientation of taking a daytime nap and waking up in pitch darkness, and the constipating anxiety of preparing for a confrontation.
But, friends, here I am, unconstipated, post-conflict, and ready to share.
To set the stage, here are some things I’ve been born with that have made the journey of hard conversations easier to navigate:
- I’m an extrovert
- My family is loud and confrontational
- I’m a very tiny person so I’ve spent a lot of time making sure I get seen and heard
- I learned and loved to read, write, and speak
For me, this was a non-negotiable foundation. I enjoyed mysteries and fantasies and deep literature. I stayed up at night reading about worlds that don’t exist, about feelings I’ve never felt, and about people (and mystical creatures) that were nothing like me.
It led to a love for writing — sad journals, angsty teen life is unfair rants, reeeaallly bad poems (when I was 8, I wrote about a girl named Aclarious who was hilarious), and essays.
I joined speech and debate. I read, wrote, and spoke for over 10 hours every week. I attended tournaments. I was not so good at first, and then I was better. I failed and failed and failed and every now and then, I picked up a prize.
I learned how to speak intentionally, understand my audience, get confident in my talking points, and never back down (that last one would be revised in later years). I took every argument that came my way.
2. I started teaching
It started when I was four and tried to teach my newborn baby brother how to walk (you can guess how well that went).
Although that didn’t quite pan out, I started volunteering and working with kids since I was a teenager. I’ve worked at Camp Galileo for five summers, and it was the best tough-conversation-navigation experience of my life.
When you’re in front of kids all day, you have to channel respect, empathy, and discipline all at once. You learn how to set expectations. You learn how to create and enforce fair consequences. You have to be the best part of yourself all the time — these kids look up to you, they learn for you, and they need to take you seriously while having fun.
It’s a noisy, wild juggling act, and I love it.
(And if working with kids isn’t enough conflict resolution for you, try dealing with their parents.)
3. I made some amazing friends
My friends are the best. It’s a scientific fact.
I used to get jealous when I saw Tumblr girls share the pumpkin spice lattes their friends would bring them. My high school friends never did that for me (but it’s never too late!! !! you know who you are!).
But over the past 10~ years, we’ve gotten really comfortable with each other, brought out the best in every person in our group, and understood how to be honest. On our vacation to Hawaii last year, we looked like the breeziest group of friends to ever walk the island, but we also had to have some pretty difficult discussions about our friendship…and how I needed to be less of a jerk.
If you’ve never fought with your friends, you should really consider it.
4. I was trained in (and practiced!) non-violent communication
I’d figured out, by this point, how to be comfortable having tough conversations. And I was decent at it — they usually ended in resolution and a better mutual understanding.
But learning about non-violent communication changed the game.
In my third year of college, I volunteered for the Whole Earth Festival (WEF). From the outside, it’s a wonderful little (big) gathering of 30,000 artisans, musicians, and hippies. It’s everything you imagine the Summer of Love to be, but more wholesome, and a lot of cultural appropriation.
They have a mandatory non-violence training for everyone who signs up to volunteer. It’s a full-day event and it’s wonderful. The staff makes you feel warm and accepted the minute you walk in. You can keep your shoes on or off. You can sit anywhere.
But you take it seriously.
I learned about “I” language, and it’s changed the way I interact.
There are tons of resources on non-violent communication and “I” language, but here’s the gist.
Instead of telling someone “You didn’t tell me the project was delayed! You should have let me know!”, you frame it from your perspective. You could say, “I’m frustrated that I hadn’t heard about the project being delayed. By being left out of the conversation, I feel like my contributions to the team are undervalued.”
I’m not exaggerating about this being a game-changer. I find that by making conversations about me, my feelings, and my reactions, it puts the power back into my hands. I practice it every day.
If you tell someone they screwed up, they can always say “no, I didn’t” or reply defensively. But if you tell someone they’re frustrated, what can they say? “No, you’re not frustrated” doesn’t make much sense.
You can’t effectively argue with someone’s truth.
5. I started going to coaching
Coaching is a recent development for me, and it’s been awesome.
I’m participating in a Women in Tech Circle with Strive. They provide leadership development and coaching for underrepresented people in tech, including women and people of color.
I was skeptical going into it. I figured I already knew how to have hard conversations and was a decent leader, and I wasn’t exactly sure what I was supposed to get out of it.
I’m halfway through the program as I write this, and my skepticism has been cured. Here’s the low-down on why all the tech brats of Silicon Valley won’t shut up about coaching (purely from my experience with Strive’s program):
- It provides you with a support system. (Mine is probably unique because I have my coach AND a small, supportive group of women to talk to online and offline.)
- It makes you practice. My coach, Nadia, validates me as a friend would, but also challenges me. She asks me questions that force me (in the best way possible) to be reflective and gives me tactical ways to practice micro-skills in every interaction.
- There’s accountability. This is key — it’s one thing to learn about tough communication. It’s a whole other thing to implement it. We have tangible and trackable challenges that mean we have to practice the skills we learn.
- Coaching gives you forward momentum. I’ve gotten tips and articles out of it, but more importantly, I have a toolkit of what to do in the context of my own future. I walked away from today’s session with a clearer idea of what it’s going to take to build Soapbox Project, the media platform I’m creating. It’s extremely difficult to get that kind of clarity and momentum in any other 1-hour situation.
A conclusion, for now
The past few days have been rough. I’ve had tough conversations with people I’d thought were my champions who ended up making me feel small (well, smaller than I already am). Practicing critical conversations is draining, but I think it might be the single most important leadership trait I possess.
After my recent experiences, I’ll be more intentional on learning how people I work with handle conflict and communication. How my leaders set expectations early on and maintain them, how they affirm those around them, how they show respect, even during situations that are not ideal.
I’m validating and affirming myself, too, in the way I’ve been unafraid to confront difficult situations and people. There’s always room for improvement, but I’m really glad I’ve been preparing and re-preparing all my life. Tough conversations have made me who I am — an empathetic leader, a good friend, and a fun, dynamic, resilient person.
I’m validating and affirming myself, too, in the way I’ve been unafraid to confront difficult situations and people. There’s always room for improvement, but I’m really glad I’ve been preparing and re-preparing all my life. Tough conversations have made me who I am — an empathetic leader, a good friend, and a fun, dynamic, resilient person.
