Candor

AI has unlocked new velocity for startups—and new visibility, too.

The faster you grow, the sooner you’ll need to prove you’re secure enough to play with enterprise customers.

The tl;dr? You need compliance to sign deals.

Vanta is hosting a session on how to make compliance work at your pace, without slowing momentum, stalling deals, or putting revenue at risk.

They’ll cover the essential steps you can take now to prepare for your first audit in the new year. Let 2026 be the year you earn customer trust and unlock new deals.

This past week, someone came to me complaining about someone else on the team. As a company of 110 people, this happens from time to time as people want to surface issues with me and ensure they’re handled properly.

The problem is that this person had already come to me complaining about the same person doing (or not doing) the same thing multiple times before. In retrospect, those conversations haven’t been productive and haven’t addressed the underlying issue.

A few months back I was working on a company manifesto (tech speak for “document”) to codify our operating principles, and one of them that I wrote was that communication should always travel the shortest possible distance. I’m confident that companies operate far more effectively when people are comfortable giving direct and honest feedback to each other.

Back to the above example: Employee A came to me complaining about Employee B. There’s a few possible outcomes from this situation:

Or, hear me out, Employee A could just directly communicate the feedback to Employee B with candor. I can almost guarantee that a thoughtful message on the side would be well received and immediately resolve the issue. And if Employee B is incapable of receiving and internalizing that feedback, then that’s an entirely different issue in itself.

When I suggested that, Employee A responded with a seemingly valid rebuttal: “I’m not their manager, I’m not even on their team, and I don’t have the bandwidth to coach someone on this.”

To which I agree – it’s not their job to coach this person. But there’s a vast difference between delivering a few sentences of feedback and providing on-going coaching (I’m just asking for the former).

And I don’t believe in the whole manager and team thing – we’re all high-performing adults and should feel comfortable sharing feedback with anyone else at the company regardless of team, seniority, or circumstance.

Granted, I understand that most people try to avoid confrontation. That’s why I think it’s so important to instill the value of direct feedback and communication as a cultural norm. It’s my job as a leader to encourage and normalize this level of candor at the company.

Related, one of my all-time favorite business books is No Rules Rules. It’s about Netflix’s high-performance and radically transparent culture. The team actually makes fun of me for often I reference it.

The whole book is insightful, but there are two specific takeaways related to communication that I wanted to highlight.

At Netflix, employees are expected to speak honestly and directly, even when it’s uncomfortable (which to be fair, is most of the time when giving direct constructive feedback).

I’m no organizational therapist, and I’m sure there are dozens of great frameworks for giving feedback, but the one they reference in the book is called the 4A framework:

Feel free to do with the framework as you please, but overall I’m such a big believer in this operating philosophy as a company.

I’d actually go as far to argue that not giving feedback is incredibly selfish. You’re doing a disservice to the other person by not helping them improve, and you’re also hurting the company by tolerating suboptimal behavior and outcomes… all because you don’t have the stones to speak your mind.

This is actually a version of one of the other operating principles I’m working on for the manifesto: be confrontational.

Smart people disagree on things, and that’s a good thing. If no one disagrees, it’s likely a sign of groupthink or that people are too afraid to contribute.

Again, it all comes back to being comfortable speaking up in situations where most people are inclined to avoid confrontation. But confrontation pushes the company towards better decisions and outcomes.

All of this has to come from the top. People need to see that it’s ok to challenge and critique the CEO. Fortunately, I have no shortage of instances where people have come to me with feedback on ways that I could improve.

In most circumstances, I had been moving so quickly that I wasn’t consciously aware that I was undermining someone’s efforts or impeding the initiative. It wasn’t intentional, and without them bringing it to my attention I would have never fixed it.

I’m a better CEO for them coming to me with their feedback, and they’re happier employees because the issue was addressed. This sounds so incredibly simple, but this type of culture is counter to how many people operate by default.

I can’t brute force my way to success like I could in the early days of the company. Today, the easiest way to compound my efforts is to build a culture where everyone on the team makes each other better.

And while I’m on my soap box talking about company culture and communication, I’ll drop this podcast I listened to this week that I found valuable: Rachel Lockett, an executive coach, talks about having difficult conversations.

Enjoy the book and podcast recommendation ✌️.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe: mail.bigdeskenergy.com/p/candor

I’m renting a house with Houck (founder of Founding Journey) in Tamarindo, Costa Rica in February with 7 other founders. We’ll be working, vibing, and delivering shareholder value. Other details:

In honor of Art Basel, check out this retro Miami rig. Incredible vibes to tap the dial-up modem.

Think you can generate a better office? Reply with your submissions 📨.

Some of my favorite content I found on the internet this week…

Turn on, tune in, drop out. Click on any of the tracks below to get in a groove — each selected from the full Big Desk Energy playlist.

Share this newsletter with your friends, or use it as a pickup line.

👉 Your current referral count: {{ rp_num_referrals }} 👈

Or share your personal link with others: {{rp_refer_url_no_params}}

📥 Want to advertise in Big Desk Energy? Learn More