Conversations You’re Too Afraid to Have but Should
- Jul 15, 2025
- 5 min read
Written by Kelli Binnings, Brand Expert & Entrepreneur
Kelli Binnings is a multi-disciplined creative who loves talking and writing about brands, psychology, and leadership. She is the founder and chief brand strategist at Build Smart Brands and is the soon-to-be author of The Breakout Creative, which is set for release in late '25. She is also in the process of completing her Master’s from Goldsmiths University in London in the Psychology of Arts, Neuroaesthetics, and Creativity.
We all have that one conversation we’ve been dodging. The one lingering in the back of your head like an email draft you never quite hit send on. Maybe it’s with a team member who keeps missing deadlines, or perhaps it’s with a partner or client who’s veering off the rails.
We all have those moments where silence feels safer, thinking the tension will dissolve on its own, and the elephant will finally leave the room. Spoiler alert: it rarely does.
I’ve done it, too. I’ve smiled through meetings where my insides were screaming. Played nice, played cool, until suddenly, I wasn’t.
And here’s what I’ve learned through years of building brands and working across countless teams: those unsaid words don’t disappear. The longer we let them sit, the more corrosive they become to our business, our culture, and our mental well-being.
When we avoid the truth, we’re not just protecting others’ feelings. We’re abandoning our own.
When resentment starts running the show
At first, it feels like patience. Like you’re doing the professional thing. You tell yourself all kinds of stories:
“Now’s not the right time.”
“Maybe it’ll work itself out.”
“I don’t want to hurt their feelings.”
“What if I say the wrong thing?”
But underneath all that is fear. Fear of rocking the boat. Fear of looking like we don’t have it all together. Fear of someone walking away.
And meanwhile, resentment quietly creeps in. You start avoiding eye contact. Your jaw tenses. You resent them, then you resent yourself.
I’ve been there. I remember one client project that had me awake at 3 AM for weeks. Constant changes. Scope creep galore. And me? I kept saying it was fine, knowing the project would end eventually. But I was doing us both a disservice.
It wasn’t the client’s fault. It was mine, for not setting a boundary earlier. And even worse, I was setting up the next designer for failure by not giving valuable feedback to the client on how to better organize, plan, and work with creatives.
That’s when it really clicked for me: holding back doesn’t save relationships. It erodes them. Quietly, painfully, until there’s nothing left but frustration.
So what happens when you finally speak up?
The wild thing is, when you finally say what’s been sitting heavy on your heart, everything realigns. I’ve seen entire team dynamics shift in one honest, vulnerable moment. It’s not about airing grievances or laying blame. It’s about saying, “This is real. Let’s face it together.”
When leaders are honest, even about not knowing all the answers, teams feel safer doing the same.
The top four benefits of speaking up:
Stronger trust: Vulnerability breeds trust.
Better performance: Clear, direct feedback helps people grow. Avoiding it only leaves them confused and stuck.
Mental clarity: Carrying unspoken issues around is exhausting. Talking it out frees up mental space for creativity and problem-solving.
Culture transformation: Teams that normalize honest, even messy, conversations create resilience and adaptability.
Feedback isn’t criticism, it’s collaboration
One of the biggest shifts I’ve made in my own business journey is learning that feedback isn’t about calling someone out. It’s calling them in.
It’s saying… “I care enough about us and our goals and want to do better.”
Sometimes the hardest part isn’t knowing what to say; it’s knowing how to start.
My approach?
Lead with curiosity: “Can we talk about how that project went?”
Be clear: “Can I share with you a few things I noticed and felt during this last project?”
Don’t blame, align: “I know we both want the same thing, [insert goal, vision, outcome]. How can we get better at working toward it together?”
Name your feelings: “This feels a little awkward to talk about. Can you be patient with me as I get through it, because I know it’s important to our progress?”
Listen.
Opening the door to conversation
This is exactly why I created Brand Food, a deck of 52 creative conversational cards and insights to spark moments of reflection, open doors for realignment, and create opportunities to share perspectives on life, business, and brand.
Sometimes we avoid vulnerable talks simply because we don’t have the right words, questions, or conversation sparks to open the door. These cards are designed to orchestrate the awkwardness, tee up the vulnerable insight, and guide conversations that otherwise may never happen.
It isn’t about scripts. It’s about having the kind of curious, honest conversations that shift everything, from how your team operates and shares feedback, to how your brand shows up, and most importantly, how you feel walking into work each day.
Just think, if one card could help you have a conversation you’ve been avoiding for months, what could a full deck of them unlock for you and your team?
The real win: Making honest talk your norm
Honest conversations shouldn’t be rare. The more you practice them, the easier they get. The tension doesn’t fully disappear, but your muscle for “moving through it” grows stronger. And that changes everything, from how you lead to how you brand to how you show up as a human being.
When you build a team or a brand where honesty is the norm (not the exception), you don’t just avoid resentment. You build resilience.
People trust each other more. Feedback flows both ways. Problems get solved faster because nobody’s wasting energy on politeness theater.
And let me tell you, working and surrounding yourself with people who aren’t afraid to tell you the hard stuff? That’s priceless.
What’s next?
If you’re curious about grabbing a set of Brand Food cards, they’re coming out in Fall 2025! Sign up here to be the first to know when they go live. If you’re interested in more articles on leadership, brand, business, and mindset, check out “thoughts” on my website or connect with me to learn more ways you can improve your brand leadership within your organization.
Connect with me on LinkedIn, Instagram, or visit Build Smart Brands.
Read more from Kelli Binnings
Kelli Binnings, Brand Expert & Entrepreneur
Kelli Binnings is a fearless thinking, multi-disciplined creative who loves talking and writing about brands, psychology, work culture, and leadership. As a life-long learner and "design your life" believer, she thrives on bringing ideas to life and joy to others through her work. Outside of her brand business and love of writing, she’s a published music photographer, wellness athlete, and soon-to-be author of her first book, titled The Breakout Creative, set for late '25. She is also in the process of completing her Master’s from Goldsmiths University in London in the Psychology of Arts, Neuroaesthetics, and Creativity. Her mission is to reframe the way people think and apply positive psychology to their professional lives.
