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Building a Culture Where the Truth Doesn't Hurt
Why I share my biggest failures with my team
Hey!
Chris here. Welcome to Blueprint—the newsletter to help you build a winning engineering team.
I've noticed something weird in tech leadership. Everyone claims to want "radical candor" and "honest feedback," but when that feedback actually arrives, suddenly everyone's defensive.
People say they want the truth, until it hurts.
But here's what I've learned after 20+ years building teams: the companies that win are the ones where truth flows freely—even when it stings.
Let me break down why brutal honesty is the foundation of every great team I've built 👇
📒 DEEP DIVE
Building a Culture Where the Truth Doesn't Hurt
A practical guide to giving and getting criticism that doesn't end in disaster.

Honest feedback is an absolute necessity for high-performing teams. But most companies get it completely wrong.
I know this because I did too.
At my first company, I had a superstar employee. He was an absolute killer at his job. He'd been working insane hours for months, and was completely burned out. The exhaustion was affecting his interactions with other team members.
I knew I needed to address it. So one night, after returning from a cross-country flight at 11pm, running on maybe 4 hours of sleep over 2 days, I (stupidly) decided that was the perfect time to have this conversation.
Both of us were exhausted, irritable, and not in the right headspace.
But I pulled him aside anyway and tried to give him feedback about how his burnout was affecting others.
What should have been a simple, supportive conversation turned into a defensive mess. He took it personally, I got frustrated that he wasn't hearing me, and we both left feeling worse than before.
My intent was right. The message was right. But my timing was completely wrong.
This experience taught me that sometimes the best response is no immediate response at all.
The "No Response" Technique
One of the most powerful communication tools I've learned is that you don't always need to respond immediately.
When hit with difficult feedback, simply saying "I need to think about that" is perfectly valid. You don't have to defend yourself on the spot.
This applies to giving feedback too. If you're exhausted, angry, or emotionally drained—wait. Your words will land better when you're in a better state.
This works in personal relationships too. Being able to say, "I'm not in a good headspace to discuss this right now" demonstrates emotional intelligence.
Why Most People Struggle With Tough Feedback
When you get feedback, you have 2 choices:
1) Take it as evidence of something you need to fix
2) Take it as a personal attack and get defensive
Most people default to #2 because their ego gets in the way. They can't separate their identity from their decisions, so any critique feels like a rejection of who they are.
Whatever you do, don’t default to #2.
Receiving and taking in tough feedback requires real confidence. When someone with solid expertise tells you you're wrong about something, it shouldn't break you. You should be able to say, "You're right. Thanks for pointing that out."
Most people giving feedback aren't trying to hurt you. They're just telling you something isn't working.
How to Give Feedback That Works
When someone on your team messes up, their reaction tells you everything.
In my world of technology, major incidents happen regularly. I've noticed that about 95% of the time, when someone causes a significant outage, they already feel terrible. You don't need to pile on—they're punishing themselves worse than you ever could.
The rare 5% who cause problems and don't care? That's a clear signal to remove them from your team.
For the 95% who feel terrible, I share my own failures. Like the time when I was 19 and took down five banks simultaneously for hours (real story.)
This accomplishes 2 things:
It shows I've been there too
It helps them see that these painful moments are essential learning experiences
The person who just made a costly mistake and feels awful about it is the least likely person to repeat it.
They just learned a $10,000 lesson in ten minutes.
If they genuinely care—if it bothers them deeply—you just watched them do years of growing in minutes. That's incredibly valuable.
Building a Feedback-Rich Culture
So how do you actually build a team where feedback works? Here's what I've done:
Make feedback normal, not special: Schedule regular, informal feedback sessions so it's not just happening during crises or performance reviews.
Model it yourself: Openly ask for feedback on your own work and decisions. You aren’t above feedback.
Reward honesty, not harmony: Publicly appreciate team members who raise difficult issues, especially when they were right and you were wrong.
Train the gap: Explicitly teach your team to pause between feeling and responding. Make "Let me think about that" a phrase everyone's comfortable using.
Fix the issues, not the blame: Keep conversations focused on improving the work, not on judgement.
The best engineers I've worked with share these habits. It's about creating a culture where you can remove the barriers between problems and solutions.
Companies where honest feedback is discouraged bleed their best people. Top engineers don't want to work in environments where truth is buried under ego and politics.
Your job as a leader isn't to be right all the time. It's to build a team that can tell you when you're wrong—and then fix it together.
🎙 EPISODE OF THE WEEK
This week on Build Your Business, Matt and I tackle the silent killer of most businesses: chaos.
We dive into how systems and standard operating procedures (SOPs) create order from chaos.
If you're drowning in tasks or ready to take your business to the next level, this episode will show you exactly how to build systems that scale.
Listen wherever you listen to podcasts: Spotify | Apple Podcasts | Youtube

BEFORE YOU GO…
The cost of poor feedback in engineering teams goes beyond hurt feelings and awkward meetings.
I've watched tech companies lose millions on failed projects because engineers couldn't speak up about flawed designs. I've seen talented developers quit rather than work in environments where pointing out problems gets you labeled as "negative."
Your most expensive bugs and your worst outages almost always have the same root cause: someone saw the problem coming but didn't feel safe saying so.
The best engineers I know don't want to be right all the time. They want to work somewhere they can be wrong, get corrected, and grow from it.
Give your team that environment, and you'll build something that lasts.
Talk soon,
Chris.