Bottom Line:
“In on the joke” teams outperform those that aren’t because they operate with more honesty, innovation, and resilience. Their ability to have high intellectual friction with low relational friction leads to better decision making, faster conflict resolution, fewer mistakes (and faster recovery from errors), and stronger alignment and execution. They’re also more engaged, less burnt out, and deeply committed.
What do you want from relationships with some of the people you spend most of your time with, such as your executive teammates?
Do you want to feel seen, heard, understood, and know someone really gets you and accepts you anyway? Do you want someone who has your back when the heat rises and who will celebrate with you when things are working just as you hoped? Do you want to be acknowledged and valued for your contributions in a way that speaks to you, not how they want to? Do you want people around you who challenge, teach, and push you to be a better version of yourself? Do you want relationships that bring “life”—shared laughter, inside jokes, and spontaneity? Do you want to be with people who thrive on a sense of shared meaning and purpose?
Elite executive teams that know each other’s superpowers and kryptonite and are for each other’s growth are what we define as an in on the joke culture. This culture becomes rocket fuel for achieving business results and relational results necessary for success.
Being in on the joke cultivates a shared awareness of how self-sabotaging behaviors affect team dynamics and organizational culture. When leadership teams create environments where members can openly notice, question, and discuss behavioral patterns without fear of judgment, they establish genuine psychological safety.
While I had experienced some of this in past roles and attempted to cultivate this in the culture of the organization I led for more than a dozen years, I had not experienced this as fully as I did in the first three months at Kairos. An example that is seared in my memory was receiving the feedback that even my quarter-baked ideas are worth sharing and help client discussion progress, AND when I do share, I need to sharpen my sharing because it can be overly complex. It was a paradoxical request that generated lots of deep and frustrating conversations, yet it was the correct and needed feedback that illustrated I could and should engage earlier with tighter thoughts. The team coupled the feedback with support, conversation, and a commitment to help me develop in future client meetings. I’m still working on being less complex, but quarter and half-baked ideas get shared more frequently.
Why Psychological Safety?
Psychological safety is the belief that you won’t be punished or humiliated for sharing your thinking as a member of a team. It’s the foundation of an “in on the joke” culture and requires intentionality, hard work, and an ongoing commitment to prioritize practices that generate courageous revelation and soft landings. Teams build psychological safety by courageously talking about the issues that are present below the surface, including the way team members are acting or working together, impacting work relational health. Like a pad that catches a high jumper after a 6’ leap over a bar head first, how others respond to courageous sharing gives the revealer the confidence to share again. Without the pad, the high jumper never leaps. They definitely won’t leap again if someone pulls the pad out from under them, which is so easy for our subconscious to do in busy and hectic staff meetings, especially when tensions are high.
How to Build an In on the Joke Culture
If psychological safety is a prerequisite to becoming an “in on the joke” team, how do you cultivate it? Here are a few key tools and practices we use regularly to maintain and develop psychological safety internally at Kairos, at The Forge, and with our clients.
Icebreakers: A structured activity or question designed to help people feel more comfortable with each other and begin sharing courageously in a low-pressure way. We start one of our weekly staff meetings with an icebreaker that is light, revealing some experience, aspiration, or belief we hold that shapes who we are. Icebreakers open the door for better staff meetings and, when done consistently, give us greater insights into each of our personalities. There are endless ways to shape an icebreaker.
In on the joke with me: I have difficulty with icebreakers. I don’t love being put on the spot without having time to think about an answer, and I’d rather not share something I’m not feeling strong about; I’d rather withdraw. Honestly, my ego wants to share something cool, funny, or overly profound, and the mental rolodex does not move at the speed of AI like I want it to. I’ve grown to appreciate the depth, nuance, struggles, joy, and kinship that come from learning more about my co-workers. So, I’m all in, and it’s helping me grow.
Candid Retrospectives: Structured processes to reflect on team dynamics, decisions, and performance that go beyond outcomes and into how the work got done. We are committed to AARs (After Action Reviews) and have a specific process we go through, including a template. See the link at the bottom of this section. Retrospectives normalize speaking up, giving/receiving feedback tied to business cases, and allow us to name tensions early and name and address behavior patterns more accurately.
Wins & Concerns: A collaborative check-in tool where team members safely share and celebrate recent successes (“wins”) and current challenges or failures (“concerns”) without fear of judgment. Kairos uses this format to regularly check in with one another on how our client work is going, how we’re doing on long-term efforts, like The Forge, and how we’re doing with our value stream initiatives within the Kairos business. This provides a balcony perspective and opportunities for collaborative discussion while getting to know each other’s joys, fears, concerns, and deficits.
Going Deeper: Prioritizing time as a group to ask more intentional questions designed to take the team deeper. Below are a number of questions focused on the core elements of psychological safety to get you started. The two biggest areas of growth for most executive teams we work with are spending more time together and spending that time talking about the most important things. Sometimes, the most important thing is to spend time working on the team by talking about the team.
While these are tools anyone can begin using to start opening things up for your team, they won’t solve systemic issues nor address an unhealthy community without deeper discussions. That’s a different post and likely best done through a conversation with a Kairos team member about how we work with clients to build the foundation of psychological safety. Book an Office Hour with us here.
We’ve discussed these as a team in-depth on our conversation series called Riffs. You can find them here.
Core Benefits of “In on the Joke” Culture
Trust and Respect
People feel safe in environments that are transparent, reliable, and consistent, where mutual trust and respect are actively cultivated.
Open, Honest, Direct Communication
People thrive when they feel heard and can engage in honest, two-way dialogue where healthy conflict is normalized as part of collaboration.
Support for Risk-Taking and Learning
People feel safe where mistakes are seen as learning opportunities, effort is acknowledged, and experimentation and creativity are encouraged without fear of judgment. If failure is punished or ignored, people stop taking initiative.
Inclusivity and Belonging
People feel safe in spaces where everyone is seen, valued, and included, fostering a deep sense of connection and contribution. It’s harder to judge or dismiss someone you genuinely know and care about.
Modeling Vulnerability
Leaders go first. Safety grows when leaders model the openness, humility, and behavior they wish to see in others. If leaders can openly share uncertainty, mistakes, and learning, then it lowers the stakes for everyone else to do the same.
Starter Questions To Go Deeper
Each example below hits on one of the five elements critical to building psychological safety on a team.
Fostering a Sense of Belonging
“What’s a moment in this team when you felt especially included or supported?”
Builds on shared positive experiences and reinforces inclusive norms.
Naming Sacred Cows
“If you had a ‘magic wand’ to change one untouchable thing in our culture, what would it be?”
Encourages candidness while softening the risk with a hypothetical frame.
Sharing Zany and Risky Ideas
“What’s the most out-there idea you’ve had for this business but never said out loud until now?”
Makes space for the wild ideas that usually stay buried.
Sharing Errors, Failures, and Areas of Ignorance
“What’s a time you took a risk, it didn’t go as planned, and you had to own it?
Spotlights accountability without shame.
Sharing Hard-to-Hear Feedback
“What kind of feedback is hardest for you to hear—and why?”
Opens the door to personal insight and empathy.