Why Your Culture Training Isn’t Sticking And What Actually Builds Trust at Work
Culture isn’t a slogan or a workshop. It’s the quality of the relationships between the people doing the work — and most leaders are getting the math wrong.
A note from me: I founded the Octagon Experts Bureau to put the sharpest experts in front of the rooms, stages, and teams that need them. Michaun Elise Winborn is one of them, and the insights below are exactly why.
Most organizations talk about culture as if it were a deliverable — a value statement to roll out, a workshop to host, an assessment to score. Then the survey numbers don’t move, attrition climbs, and someone publishes another article about how corporate training doesn’t work.
Here’s the uncomfortable diagnosis: the training isn’t the problem. The premise is. Culture isn’t an artifact you install. It’s the accumulated behavior of the people inside your organization — how they speak to each other, how they communicate when no one is watching, whether they advocate for each other or quietly snipe. And nearly all of that runs on one thing leaders consistently underweight: relationships.
The Math of Trust
There’s a simple equation worth memorizing: vulnerability × time = trust. Trust is not declared in an all-hands meeting or generated by a values poster. It’s the stacking and layering of small moments of vulnerability over time. Which means you cannot shortcut it, and you cannot fake it.
This is where many leaders get stuck. “Vulnerability” at work sounds like an invitation to overshare, and most people — reasonably — have no interest in handing their colleagues data to use against them later. But vulnerability in the workplace doesn’t require you to word-vomit your personal life. It can be as small as sharing a vacation photo, offering your pronouns, mentioning the degree you actually earned versus the job you actually do, or naming a skill you have that isn’t being used. Anything on your résumé is fair game and still personal — it just isn’t private.
The point is the muscle, not the disclosure. Every small offering lowers a barrier. Enough of them, repeated over months and years, become the substrate of a team that can actually disagree, collaborate, and produce good work together.
The Fastest Way Leaders Destroy Trust
If trust is built in small moments, it is broken in them too. The single most efficient way a manager erodes trust isn’t a dramatic blow-up. It’s indifference — not caring about their people, professionally or personally.
That indifference shows up in mundane ways: failing to develop someone, withholding the context a direct report needs to succeed on a project, taking credit instead of giving it, never asking what someone is working toward. You don’t have to be a bad person to do this. You just have to be busy and uninterested. The cost compounds quietly until you see it in exit interviews, engagement scores, and eventually litigation.
The leaders who build durable cultures do something different: they build relationships even with people they don’t particularly like, because they understand that everyone holds data, context, and capability they themselves don’t have. Relationships aren’t sentimental. They’re operational infrastructure.
The Gap That Becomes a Lawsuit
Look closely at most organizations in trouble and you’ll find a specific gap: CSAT and revenue metrics look fine, but the scores on my manager cares about me, I have the same opportunities as others, and inclusion is real here are quietly underwater. Leadership reads the top-line numbers and concludes things are working. Employees are living a different reality.
That gap is where reputational risk is born. It’s also where the bait-and-switch happens: people are recruited into a culture that was sold to them and discover, three or six months in, that it doesn’t exist. They leave. The cycle repeats. And the soft skills no one wanted to invest in turn out to be the exact skills whose absence costs the most.
A Framework for Leading Through It: Wake Up, Interrupt, Navigate
Awareness alone has never changed behavior. A generation of bias trainings proved this — they were excellent at exposing problems and terrible at telling anyone what to do on Tuesday morning. Here’s a proven framework:
“Wake up” - Get honest about the systems, inherited norms, and defaults you’re actually operating inside — at the org level and your own. Get curious enough to gather real data instead of assumed data.
“Interrupt” - Identify the inherited behaviors, biases, and communication defaults that quietly cause harm, and disrupt them in real time. You can’t exit every system, but you can stop reproducing it inside your team.
“Navigate” - Move through the system with integrity rather than performance. Make in-the-moment decisions — about hiring, promotions, conflict, negotiation, who gets airtime in the meeting — that are equitable and considered, not reflexive.
The framework isn’t only for questions of inclusion. It works anywhere a leader has to act under pressure with incomplete information and inherited habits — which is to say, most of the job.
What to Measure 90 Days Later
Culture is not tangible, which is why leaders pretend it can’t be measured and then act surprised when it deteriorates. It can be measured — through pulse questions designed to test whether difficult conversations are landing differently, whether meetings are more inclusive, whether employees notice their manager engaging differently than they did a quarter ago. If your people can’t feel the change, there isn’t one.
The through-line of all of this is unglamorous and inconvenient: relationships are the work. Not the soft part of the work. The work. Products, retention, reputation, and risk all sit on top of how well the humans inside your building actually trust each other. Treat that as frou-frou and you will keep paying for it — in attrition, in lawsuits, in the gap between the culture you advertise and the culture people experience.
This piece draws on the expertise of Michaun Elise Winborn, CEO and Principal Coach of Born2Win Coaching, who advises leaders and organizations on building trust, navigating conflict, and driving culture change that actually sticks. She speaks, coaches, and facilitates for executive teams, conferences, and people-leader audiences working through culture, retention, and leadership development.
▶ Watch the full interview with Michaun Elise Winborn:
📅 To book Michaun Elise Winborn for your next event, conference, or training, contact the Octagon Experts Bureau at booking@octagonexpertsbureau.com, or explore the full roster at octagonexpertsbureau.com/roster.
About the Founder:
Kelly Charles-Collins is the Founder of Octagon Haus and Octagon Experts Bureau, where she helps experts transform what they know into authority, enterprise, and economic power. A speaker, author, and former trial attorney, Kelly writes and speaks about communication, leadership, reinvention, and expertise-driven business. Her work has been featured in Forbes, Fast Company, Authority Magazine, and on ABC, CBS, and NBC.
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