Most leadership mistakes that hurt company culture don’t look like culture problems at first. They look like practical choices in the moment: avoiding the conversation, making the exception, letting standards slide, assuming people will pick up the history and values of the company on their own.
I recently asked a wide range of business leaders about the biggest leadership mistakes managers are making right now, and many of their answers came back to the same issue: the small choices leaders make that weaken trust, culture, and connection over time.
Business Leaders on the Top Leadership Mistakes That Hurt Company Culture and Trust
Mike Viola, CEO of CongruityHR: Managers are consistently losing sight of the human side of leadership. Most are buried in meetings, emails, reports, and putting out fires, measuring activity instead of outcomes. In the process, they deprioritize what I’d argue is most important: coaching, developing, recognizing, and genuinely connecting with their teams. Simply put, they need to spend less time managing tasks and more time leading people. People don’t leave companies because they had one too many meetings. They leave because they don’t feel valued, challenged, or connected to a purpose. Great leaders create clarity. They set high expectations, remove obstacles, coach consistently, celebrate wins, and hold people accountable. They build environments where people know what’s expected of them and have the support to succeed. Just as importantly, they take ownership of developing talent. The best managers mentor intentionally, give honest feedback, and treat mistakes as learning opportunities. They share credit freely and take responsibility when things fall short. They also lead with humility. Strong leaders aren’t threatened by talent; they actively seek it out. They hire people who are smarter, more experienced, or more specialized than they are, knowing that great teams outperform even the strongest individual leader. As AI continues to automate administrative work, the human side of leadership becomes even more important. While AI can summarize a meeting or analyze data, it cannot inspire, earn trust, mentor a young employee, or create a culture people want to be part of. The best leaders will use technology to free up more time to lead, not less.
Kevin Diamond, CEO of Lumi: The biggest leadership mistake I see right now is assuming company culture will sustain itself. Many organizations are focused on return-to-office policies, productivity metrics, and hiring plans, but they’re overlooking a more fundamental challenge: a generation of long-tenured employees is leaving, taking institutional knowledge and cultural memory with them. Culture isn’t something that survives by accident. Leaders need to intentionally capture the stories, values, and behaviors that define their organizations and create opportunities for newer employees to learn them. At LumiCup, our mission is rooted in challenging long-standing assumptions about disposable products and sustainability. Preserving that entrepreneurial mindset requires more than onboarding documents or process manuals. We intentionally create opportunities for team members to learn the stories, decisions, and values that shaped the company so those principles continue to guide future growth. In an era of hybrid work and shorter employee tenures, the managers who succeed will be the ones who treat mentorship, storytelling, and knowledge sharing as core leadership responsibilities rather than informal practices that happen on their own.
Dr. Kristen Gwinn-Becker, CEO of HistoryIT: One of the biggest leadership mistakes I see today is assuming that organizational knowledge naturally transfers from one person to the next. Too often, critical context, past decisions, important stories, and lessons learned live in individual employees’ inboxes, hard drives, or memories. When leaders retire, teams restructure, or employees move on, that knowledge leaves with them. The mistake is assuming history is passive, when in reality it is an active leadership tool. When organizations ignore their history or treat it as a pile of materials to deal with someday, they miss opportunities to make better decisions, strengthen culture, and build on the work that came before. Leaders should treat organizational knowledge as a strategic asset that requires intentional stewardship. Digital preservation and digital archives give organizations a practical way to capture, organize, and activate the records, stories, and institutional context that help teams move forward with clarity. Just as organizations invest in talent development and succession planning, they should invest in knowledge continuity. Organizations that preserve and use their history are better positioned to navigate leadership transitions, connect people to a shared purpose, and avoid repeatedly starting from scratch.
Dr. Raleigh Duncan, founder and CEO of Clearlight: Micromanaging employees is the biggest leadership mistake I regularly see managers make. Our employees become empowered when they are given projects and the autonomy to tackle or solve problems on their own or as part of a bigger team. Managers should set expectations and provide support when needed, rather than constantly overseeing every step along the way. Employees should have an understanding that you do trust them to complete the project or task at hand. This approach helps employees expand their capabilities, build their confidence, and, at the same time, reinforce their importance as an integral part of the organization.
Patsy Doerr, Chief People and Culture Officer of LRN: Trust erodes when leaders hesitate to address issues directly or fail to hold honest conversations. Whether the conversation is about performance, team dynamics, or a workplace concern, leaders should approach it with curiosity and empathy, rather than make assumptions and focus on understanding the underlying issue. It’s also important to ensure people feel safe speaking up and sharing their perspective without fear of retaliation or judgment. Difficult conversations that are handled well can reinforce accountability while also strengthening trust and psychological safety. By effectively navigating these conversations, leaders demonstrate their commitment to the well-being of their team and the organization as a whole. Ultimately, the ability to handle tough conversations leads to enhanced employee engagement, improved morale, and greater productivity.
Stephanie Daniel, VP Partners at Fora: The biggest leadership mistake managers – and companies – make right now is losing focus on human connection while over-indexing on efficiency and output. We’re at an extraordinary point in time: AI and technology are accelerating everything we can do, and companies must enable talent with the most innovative tools at their disposal. But strong leadership also means ensuring people still feel seen, valued, and empowered. Humans and technology, anchored by real mission alignment: that’s the most powerful recipe for building generational companies like Fora that genuinely change the course of business. Maslow mapped this decades ago: humans don’t just need stability and a paycheck – they need belonging, esteem, and purpose. While most corporate management is designed around the bottom of that pyramid, cultural strength at the top and a community with a deeply human mission – like empowering travel entrepreneurs – creates a powerful productivity feedback loop that no efficiency tool can replicate. Having spent over 15 years in large corporate finance before making the entrepreneurial leap, I’ve lived both sides. That’s why I believe startups have a deepening structural edge in this era: we can stay agile, innovative, and human, without getting buried in process and bureaucracy.
Mark Steffe, President and CEO of First Command: The biggest mistake I see is leaders confusing communication with connection. They send the emails, post the updates, record the videos, and then wonder why their teams still feel disconnected or resistant to change. The reality is you can communicate something a dozen times and still have people hearing it for the first time, filtered through their own concerns and uncertainties. That gap between what you think you’ve said and what your team has actually absorbed? That’s where trust breaks down and morale erodes. What leaders need to do differently is invest in understanding before action. Before you roll out the next initiative or push through the next change, ask yourself whether your people genuinely understand the why, not just the what. That means getting out from behind the screen and having real conversations. At First Command, we build structured opportunities for two-way dialogue because leadership isn’t about broadcasting; it’s about connecting the dots for people so they can see how their work ties to something bigger than a to-do list. When people feel that connection, everything changes: engagement, performance, retention. All of it.
Mesh Gelman, founder and CEO of Cumulus Coffee: Many leaders who are building teams look to hire primarily based on experience and background. While relevant skills are great, what’s even more important is strong buy-in to the mission, work ethic, and willingness to learn new areas of expertise. You can teach almost anyone new skills, but there’s no substitute for the qualities that make someone a reliable and effective team member. I also believe that the most important trait you can model for your team as a leader is true connection with the customer. Building relationships directly with our community members has allowed me to continuously absorb feedback and deliver a product that customers are excited to use. While maintaining a strong vision as a founder is important, it shouldn’t get in the way of incorporating genuine customer input that enhances the user experience. Lastly, I strive to communicate the advantages and dangers of AI. AI is very new and it’s in the pioneer stages. It has great promise and I encourage the team to use it often. However, great leaders need to make sure that it doesn’t make them or their teams lazy.
Seth Collins, Managing Partner of martinwolf: I think the biggest mistake managers make right now is having a lack of patience and a lack of caring. More than ever, employees need to know they are loved and safe if you want their loyalty and commitment. They view AI as a threat, and so managers need to spend more time thinking about using it as a resource, a tool for employees. Remember, AI won’t manage your customers.
Michael Jacobson, CEO of French Florist: The old model assumed you could see everyone, hover, and correct behavior in real time. That world is gone. Teams are distributed, work moves fast, and this generation won’t be micromanaged (they’ll just leave). When you can’t watch anyone, the only thing holding a team together is shared principles (a shared “why”, understanding the internal compass of how each team member operates in life). This is not values painted on a wall. These are principles you’re willing to make expensive decisions over. Here’s the uncomfortable part: your real culture isn’t your mission statement. It’s the worst behavior you’re willing to tolerate from your best performer. Every manager has an experience at some point where someone is crushing their numbers, but they quietly trample what you say you stand for. The moment you keep them anyway, you’ve told everyone that results buy a pass on values. And everyone is watching. We are scaling a brand through the vehicle of franchising, and scale is merciless here: every new location and every new hire multiplies whatever you tolerate. Get the values loose and you don’t get one problem; you get a hundred copies of it. So the job isn’t managing tasks. It’s building your entire people system around a short list of non-negotiable principles, then running every decision through them. Hire to them, even when the more skilled candidate doesn’t fit. Coach to them. Promote to them, so the people who live the values become the visible proof of what gets rewarded. And when someone truly won’t live them, let them go, even the talented one. Especially the talented one. There is someone who is equally if not more talented than them out there that is more aligned to the principles of the company. Do that, and you stop managing behavior, because the culture starts doing it for you. Identify the principles your company lives by and hire, coach, promote, and protect it deeply to those principles.
Frequently Asked Questions
How do leaders damage trust at work?
Many of the leadership mistakes that hurt company culture also damage trust. Leaders lose trust when they avoid difficult conversations, apply standards unevenly, ignore concerns, or tolerate behavior that contradicts the values they talk about. Trust gets stronger when people see leaders handle hard moments with honesty and consistency.
What are signs of a weak company culture?
Signs of a weak company culture include low trust, poor communication, inconsistent standards, avoided conversations, high performers getting special treatment, and employees feeling disconnected from the organization’s values. Culture usually shows up most clearly in what leaders tolerate under pressure.
What leadership mistakes hurt company culture?
Leadership mistakes that hurt company culture include avoiding honest conversations, tolerating behavior that violates company values, communicating without real connection, assuming culture will take care of itself, and letting important knowledge leave with longtime employees.
How can leaders build a stronger company culture?
Leaders can build a stronger company culture by being clear about standards, addressing problems directly, recognizing the behavior they want repeated, and making sure the company’s values show up in real decisions. Employees judge culture by what they experience, not by what the company says about itself.
Why does communication matter to company culture?
Poor communication is one of the leadership mistakes that hurt company culture because people need more than updates. They need context, clarity, and a chance to understand how decisions affect their work. When leaders only broadcast information, teams can still feel disconnected.
