Unveiling the unvarnished truths of leadership, this article distills hard-earned wisdom from seasoned professionals. Gain exclusive access to strategies that have been forged in the crucible of real-world experience. These expert insights offer a roadmap for navigating the complex terrain of modern leadership.
- Create Space for Conflict
- Show Vulnerability as Strength
- Listen to Your Team
- Prioritize Clear Communication
- Value Emotional Intelligence
- Embrace Failure as Learning
- Adapt Leadership to Individual Needs
- Emphasize User-Friendly Systems
- Serve a Higher Purpose
- Avoid Micromanaging
- Balance Compassion with Decisiveness
- Allow Room for Failure
- Engage in Customer Service
- Never Surrender Control of Your Future
- Prioritize Professional Growth
- Maintain Work-Life Balance
- Delegate Effectively
- Adapt to Change Quickly
- Understand Team Before Implementing Changes
Create Space for Conflict
One leadership lesson I learned the hard way is the importance of creating space for conflict. Like many leaders, I equated silence with consensus, assuming everyone was on board if no one voiced disagreement. That assumption backfired spectacularly during my time as president of the student union at Carleton University in Ottawa, Canada.
We had an ambitious idea to create a parody music video to encourage students to vote. Excited by the concept, I pitched it to my team. Some members were enthusiastic, and no one expressed reservations. Assuming everyone agreed, we moved forward. The video went viral—but not for the reasons we hoped. Instead of inspiring students, it became the subject of national ridicule, earning titles like “the most embarrassing music video in Canadian history.” It was a humbling moment.
In the aftermath, we debriefed as a team. I discovered that several members had serious doubts about the idea but didn’t feel comfortable voicing them. They admitted they hesitated to challenge me because of my strong personality and my enthusiasm for the project. Their silence wasn’t agreement—it was fear of conflict.
This experience taught me that silence can be a barrier to innovation and effective decision-making. Avoiding conflict often leads to poor outcomes, as it prevents diverse ideas and critical feedback from surfacing. True collaboration requires fostering an environment where team members feel psychologically safe to challenge ideas, even their leaders.
Now, I actively ignite and manage conflict within my teams. I ask direct questions, encourage dissenting opinions, and explicitly invite alternative perspectives. Instead of asking, “Does everyone agree?” I now ask, “What concerns or doubts do you have?” This approach has transformed how my teams operate. When people feel safe to speak up, better ideas emerge, decisions improve, and trust deepens.
My advice to other leaders is simple but powerful: lean into conflict. Recognize that productive conflict is essential for growth. The more you embrace it, the less it feels like a “dirty word” and instead becomes a natural part of your team’s dynamic. Create psychological safety by showing your team that disagreement is not only acceptable but valued. Set the tone by admitting your own mistakes and encouraging open dialogue. And most importantly, remember that your role as a leader isn’t to have all the answers—it’s to guide your team to find the best ones together.
Fahd Alhattab, Founder & Leadership Development Speaker, Unicorn Labs
Show Vulnerability as Strength
A leadership lesson I learned the hard way is that showing vulnerability isn’t a weakness—it’s actually your biggest strength. Early on, I thought being a leader meant looking like I had everything perfectly figured out. I’d walk into meetings thinking I needed all the answers, never admitting when unsure about something.
The wake-up call came during a major project when my “I know everything” attitude was actually holding my team back. I realized I was creating an invisible barrier that stopped people from really opening up and sharing their best ideas. It was like I was saying, “I’m the boss, so I must be right,” without even realizing it.
Now, I do things differently. When I’m stuck or unsure, I say so. I’ll straight-up tell my team, “I’m not sure how we should tackle this. What are your thoughts?” And wow, the magic that happens when you create that kind of open space—it’s incredible. People start sharing ideas, collaborating, and solving problems in ways I never could have predicted.
My advice to other leaders? Drop the superhero act. Nobody expects you to be perfect. What people really want is someone genuine—someone who listens, admits when they don’t know something, and is willing to learn together. Leadership isn’t about having all the answers. It’s about creating an environment where everyone feels comfortable bringing their best self to work.
Trust me, the moment you start being real, you become a truly powerful leader. It might feel scary at first, but it’s absolutely worth it.
Bradford Glaser, President & CEO, HRDQ
Listen to Your Team
One of the most valuable leadership lessons I learned came early in my journey with my group: the importance of truly listening to my team. Early on, I thought my job as a leader was to have all the answers, to chart the course and inspire others to follow. But I quickly realized that when I rushed to solve problems or push my ideas, I wasn’t fostering the collaboration or trust we needed to thrive. I learned this the hard way—by seeing talented team members hesitate to speak up or, worse, feel unheard.
This experience shifted my approach entirely. I realized that leadership isn’t about having all the answers but creating space for others to share theirs. Now, I prioritize listening with intention. Whether it’s in one-on-one conversations or team meetings, I make it a point to ask open-ended questions and resist the urge to jump in too quickly. Often, the best solutions come from the people closest to the problem.
My advice to other leaders? Embrace humility and remember that listening is your superpower. It’s not just about hearing words; it’s about understanding perspectives and showing your team that their voices matter. The more you listen, the more trust you build—and trust is the foundation for innovation and growth.
Leadership is a constant learning process, but that lesson taught me that the best leaders don’t act as the loudest voice in the room. Instead, they amplify the voices of others. It’s a humbling and incredibly rewarding shift, and it’s shaped the way I lead every day.
Justin Landis, Founder, Justin Landis Group
Prioritize Clear Communication
One leadership lesson I learned the hard way is the importance of clear communication. Early in my career, I assumed that my team understood my vision and expectations without needing detailed explanations. This led to confusion, misaligned goals, and missed deadlines. I realized that effective leadership requires not only setting a clear direction but also ensuring that everyone is on the same page. By improving my communication skills, I was able to foster a more cohesive and productive team.
Based on this experience, my advice to other leaders is to prioritize transparent and frequent communication. Take the time to clearly articulate your goals, expectations, and feedback. Encourage open dialog and actively listen to your team’s concerns and suggestions. This not only prevents misunderstandings but also builds trust and collaboration within the team. Remember, a well-informed team is a motivated and efficient team.
Wes Wakefield, Founder, Pro Coffee Gear
Value Emotional Intelligence
One leadership lesson I learned the hard way was the indispensable value of emotional intelligence in the workplace. Early in my entrepreneurial journey, when expanding a diagnostic imaging company into São Paulo, I initially overlooked the importance of fostering strong interpersonal relationships. This oversight led to a high turnover rate and decreased morale, hampering our growth during a critical expansion phase. This experience taught me that empathy and self-awareness are crucial for nurturing a motivated and productive workforce.
I’ve since embedded emotional intelligence into my leadership framework, not only changing company culture but also driving a consistent year-over-year revenue increase of over 50% for small firms I’ve supported. To other leaders, my advice is to invest in understanding your team’s emotions and motivations genuinely. Prioritizing emotional intelligence will lift team dynamics, improve decision-making, and ultimately contribute to robust business success.
Victor Santoro, Founder & CEO, Profit Leap
Embrace Failure as Learning
A leadership lesson I learned the hard way is embracing failure as a learning opportunity. I hesitated to take risks early on because I feared failure might set me back or make me look incompetent. I quickly realized that avoiding failure meant avoiding growth. When things didn’t go as planned, it was easy to get discouraged, but over time, I learned that every setback offers valuable insights.
This experience reshaped my approach to leadership. Now, I encourage my team to experiment, take calculated risks, and learn from their mistakes. We’ve built a culture where failure is seen not as something to be ashamed of but as a stepping stone toward innovation. This shift has made us more adaptable and helped us remain open to new strategies, partnerships, and ideas.
For other leaders, my advice would be to reframe your mindset around failure. Instead of viewing it as a roadblock, see it as a necessary part of the process. Encourage your team to take risks and celebrate the lessons learned, even when things don’t go perfectly. Leadership is about creating an environment where people feel safe to try new things, knowing that setbacks are just part of the journey to success. When you lead with that mindset, you empower your team to push boundaries and achieve far more than they thought possible.
Darcy Cudmore, Founder, RepuLinks
Adapt Leadership to Individual Needs
I have done well to forge a one-size-fits-all approach to leadership thinking, all thinking about everyone. I thought that clarifying expectations and giving clear directions would be sufficient motivators for every team member. But experience quickly taught me that everyone brings a different personality, set of strengths, challenges, and communication style to the table. What worked for one person might not work for another, and the fact that we tried to approach everyone exactly the same way often backfired and led to disengagement or misunderstanding.
One example that illustrated this lesson for me was two members of my team with strikingly different work styles. One depended on frequent check-ins and in-depth instructions, the other wanted independence and results-oriented structure. The same leadership was not a fit for both. The detail-oriented worker felt disregarded when I offered high-level direction, and the self-sufficient team member felt micromanaged when I attempted to be more hands-on. This disconnection doesn’t only impact their performance but also their morale and satisfaction in the workplace.
I had to learn quickly that to best inspire and support my team, I needed to adapt my leadership style so as to meet people’s unique needs. I learned what each one of my team members preferred to work with and what they responded to and how they liked receiving feedback. For some, it was weekly check-ins and collaborative brainstorming that worked best; others shined when left to their own devices to take ownership of their projects with little interference.
By adapting my style, both individual performance and team dynamics significantly improved. This effort led to employees feeling better understood and valued, driving their engagement and willingness to contribute. It also helped build a sense of trust because they could see that I was invested in their personal success and growth.
My advice to other leaders is to spend time getting to know your team’s unique dynamics, then lead accordingly. Pay attention to what they like, the questions they ask, and how they react in different circumstances. Leadership is not a one-size-fits-all, it’s a matter of figuring out what gets the best out of each individual you have on your team and how to align them with the team’s goals. This personalized approach leads to a more aligned, inspired, and high-performing team.
Ryan Hetrick, CEO, Epiphany Wellness
Emphasize User-Friendly Systems
It’s important to emphasize user-friendly systems. Early on, I underestimated how critical ease of use is when rolling out new initiatives, particularly cybersecurity policies. Employees struggled to adopt the systems we implemented, not because they didn’t value security, but because the processes felt too complicated. This resulted in delays and inconsistent compliance. It taught me that no matter how good a solution is, its effectiveness depends on how easily people can incorporate it into their daily routines.
This experience shaped my approach to leadership. I now prioritize simplicity and usability in every system we implement. Let other leaders focus on the user experience when introducing changes. Get feedback from your teams early, understand their pain points, and make adjustments to ensure adoption feels natural. When people feel comfortable with the tools they’re given, the results are much smoother and more consistent.
Christian Espinosa, Founder and CEO, Blue Goat Cyber
Serve a Higher Purpose
Perhaps the most important lesson I’ve learned as a business owner and leader is that it’s not ALL about you. Leadership is not about personal recognition, ego or authority; it’s about serving a higher purpose—whether that’s the organization’s mission or the development and professional fulfillment of its people. Integrity forms the bedrock of effective leadership; and when it is lacking, trust crumbles. Integrity is important, but the true test of a leader is their capacity to develop and lift up others. Throughout my career I’ve become acutely aware of how important it is to develop other leaders and help people reach their potential. It’s an ongoing reminder that leadership is about serving others, and not oneself.
I’ve seen it firsthand: When a leader makes it all about themselves, things start to unravel—the mission gets lost, and people start to feel undervalued. Although it may yield short-term wins, this style of leadership can have dire long-term consequences on morale, culture and the organization’s future. I always take it to heart and feel fortunate enough to just be grateful and humble about the trust given to me. Leadership is a privilege, not a right, and with that privilege comes an enormous responsibility to lead, listen, inspire and care for others.
By keeping the focus on the team and the collective goals we’re all working towards, I’ve been able to build better relationships and reinforce that the mission always comes first. Again, leadership isn’t easy, but there is one thing I know—we lose track of what’s important the moment it becomes about us.
Marc Hardgrove, CEO, The Hoth
Avoid Micromanaging
The lesson I learned as a leader is that micromanaging hinders growth. Before, I thought being a hands-on leader meant overseeing every detail to make sure things were done exactly how I envisioned. What I didn’t see at the time was how this approach stifled creativity and left my team feeling like I didn’t trust them. It led to burnout for me and frustration for them, which created a cycle that was hard to break.
What changed my perspective was a project where we had to restructure our entire client onboarding process. At the time, we were expanding rapidly, and our existing system couldn’t handle the volume of new clients. I wanted to oversee every detail, but the timeline was so tight that I had no choice but to trust my team. I assigned different parts of the project to team members, from creating workflows to implementing new technology, and let them take charge.
The results blew me away. They not only streamlined the process but also introduced features like automated client updates and better internal tracking, which improved efficiency across the board. These were ideas I hadn’t considered, and the project ended up being a huge success. It was eye-opening to see how capable my team was when given the opportunity to take ownership. It taught me that stepping back can lead to outcomes far better than if I tried to control every step myself.
Shaun Bettman, Chief Executive Officer, Eden Emerald Mortgages
Balance Compassion with Decisiveness
The need for balancing compassion with decisiveness, especially in a practice focused on personal injury and disability cases. Early in my career, I believed that being empathetic meant taking on every burden my clients and team faced, often to my detriment. I found myself overextended, trying to be everything to everyone, which ultimately risked slowing down the progress of my cases and my firm’s growth.
I realized that leadership in the legal field requires careful equilibrium. Empathy is vital—it’s the foundation of trust and the cornerstone of how I connect with clients navigating life-changing injuries or disabilities. But decisions must also be made swiftly and with conviction, especially when lives and livelihoods are on the line. Compassion isn’t about carrying every load yourself; it’s about creating systems, empowering teams, and guiding clients through their challenges with clarity and strength.
This lesson reshaped my approach to managing my firm. I now focus on creating an environment where my team feels supported and capable while maintaining a results-driven mindset. I ensure that each case has a clear path forward, and I empower my team to take the initiative while staying accessible for guidance. This has allowed us to recover millions yearly for our clients and consistently exceed expectations in the courtroom.
For other leaders in demanding industries, my advice is to lead with heart but never lose sight of the need for action. Build trust by showing you care and making the tough calls that drive progress. When you balance compassion with decisiveness, you serve your clients better and inspire confidence in your team and yourself.
Mia Mancinelli Cloud, Founder, Cloud Law Firm
Allow Room for Failure
One leadership lesson I learned the hard way is the importance of letting people fail. As much as I wanted to prevent mistakes, I realized that sometimes you have to let others experience the consequences to truly learn and grow. Of course, it’s essential to warn them and explain potential challenges ahead, but if they choose to proceed, fighting it often creates more tension than it’s worth. Instead, I’ve found it more effective to focus on helping them navigate through the failure when it happens. This approach not only fosters personal growth but also preserves trust and strengthens the relationship.
As the saying goes, there are two ways to learn: through mentors or mistakes. Mistakes are inevitable, so it’s vital to have a good mentor to help guide you through them. My advice to other leaders is to allow room for failure while being a steady mentor who can provide insight and support. This balance ensures that people not only learn but also feel empowered and supported in their growth journey.
Rizala Carrington, CEO, MyGrowthAgent.com
Engage in Customer Service
One tough leadership lesson I learned was the importance of personal involvement in customer service. Early in my leadership role, I delegated all client interactions, assuming that skilled staff would handle everything perfectly. When a major project went awry due to a lack of clear communication, I realized being hands-off led to a disconnection with client needs and project execution.
This experience taught me the value of being actively engaged and transparent with customers. Now, I make it a priority to personally check in with customers, ensuring their concerns are addressed promptly. This hands-on approach helped us earn over 200 five-star reviews.
For other leaders, my advice is to never underestimate the power of direct communication in building trust and preventing misunderstandings. Additionally, I recommend fostering a culture of open feedback within your team. During that project mishap, team members felt hesitant to address issues as they arose. Creating a safe environment for honest, proactive communication among staff can bridge critical gaps before they impact client satisfaction.
Matt Heinbaugh, CEO & Owner, Yeti Restoration
Never Surrender Control of Your Future
One leadership lesson I learned the hard way is that while trust is essential, you should never hand over full control of your future to someone else. Years ago, at a previous agency, I brought in a sub-manager to help lighten the load so I could finally take a well-earned two-week vacation. I trusted this person fully, assuming they had the team’s and the company’s best interests at heart. When I returned, I was blindsided—this individual had turned the company against me and I left the agency.
The fallout was catastrophic for the agency. Within 20 weeks, it went bust as clients, many of whom had trusted me personally, pulled their work. It was a harsh and painful lesson, but one that changed me for the better. I realized that as a leader, you can delegate responsibility, but you should never surrender control of your vision or your future.
That experience taught me two key things. First, leadership isn’t about being everywhere all the time—it’s about staying connected to your team and your business in a way that fosters trust but still allows you to keep a pulse on what’s happening. Second, it’s critical to hire carefully. Look for people who share your values, are aligned with your vision, and bring integrity and transparency to the table. Leadership is about empowering others, but you need to make sure they are the right people to empower.
When I started my own agency after that experience, I built it differently. I remained hands-on where it mattered, set clearer boundaries, and ensured that anyone I brought into the fold was someone I could trust not only professionally but personally. My advice to other leaders is simple: trust, but verify. Give your team autonomy and space to thrive, but don’t lose sight of the bigger picture. You can’t control everything, but you can control who you trust and how you lead. Ultimately, that hard lesson was a blessing in disguise—because it gave me the clarity to build something better and stronger.
Jm Littman, CEO, Webheads
Prioritize Professional Growth
It was the impact of prioritizing professional growth opportunities for my team. I focused too much on achieving immediate business goals before, overlooking the importance of employee development. This approach led to lower morale and increased turnover, which highlighted the need for change. I came to understand that when employees see opportunities to learn, grow, and advance, they feel more valued and become more engaged in their work.
To other leaders, I would emphasize treating professional development as an investment rather than a cost. Initiatives like training programs, mentorship, or support for certifications can significantly enhance team morale and productivity. When employees feel supported in their growth, they are more motivated to perform at their best, fostering a positive work culture and better overall results for the organization.
Ben Wieder, CEO, Level 6 Incentives
Maintain Work-Life Balance
One important leadership lesson I learned is the value of maintaining a work-life balance. At first, I was so focused on my professional responsibilities that I neglected my personal life and time for myself. This oversight led to burnout, decreased productivity, and strained relationships with both colleagues and loved ones. The constant pressure negatively impacted my well-being, which, in turn, affected my ability to lead effectively.
Leaders: always prioritize your health and personal life. Establish clear boundaries that allow for rest and recovery. When you take care of yourself, you can lead more effectively, make better decisions, and nurture stronger relationships. Balance is essential for long-term success in both your professional and personal life.
Aspen Noonan, CEO, Elevate Holistics
Delegate Effectively
One of the hardest lessons I’ve learned as a leader is the importance of effective delegation. When I first co-founded a climate-tech startup dedicated to creating sustainable fuels and materials, I assigned projects to other team members without clear expectations and realistic timelines, and I did not fully understand their capacities.
This became especially apparent during rapid growth; for example, we doubled the size of our team from 10 people in 2023 to 21 in 2024. When we launched our first demonstration plant at Oxford Airport in August, I realized that hiring the right people and knowing everyone’s strengths and weaknesses is crucial to maximizing the team’s performance, which ultimately can deliver the outcomes as planned.
Before people start their projects, they should know what outcomes they need to deliver and by when and why. Setting up a mission impossible task will frustrate everyone. If I have to delegate an important task to a person who needs training or additional resources, as a leader, I should provide enough support without micromanaging. Delegating allowed others to bring their expertise to the forefront, which not only strengthened our operations but also created a more engaged and motivated team.
Reflecting on this, I’ve learned that leadership is not about being involved in every process but about building a culture where people feel comfortable asking questions and seeking support where needed. My advice to other leaders? Trust your team and create a culture where mistakes are viewed as opportunities to learn and develop a new approach to challenges. As I’ve observed, staying open to new ideas and actively seeking feedback are essential qualities for any growing business.
Jane Jin, Co-Founder and COO, OXCCU
Adapt to Change Quickly
In 2020, we had to pivot fast. Lockdowns forced us to shift focus from offering long-term office leases (our bread and butter) to more flexible and virtual options. It wasn’t just a product pivot, though; it meant we had to re-educate the team, update sales scripts, and reshape our client relationships.
To get back on our feet, we started by listening—both internally and externally. Those on the ground, our sales and customer support teams, were critical in highlighting the drastically changed client needs, and thankfully, we were able to act fast on that feedback. We also invested in tools and training to help staff adjust to our new working model.
One thing I learned: adaptability is a team effort. Leaders don’t need all the answers, but they do need to create a space where others can share theirs. Trust your team, act on the data, and focus on providing solutions that align with emerging demands rather than holding on to what used to work.
Teresha Aird, Chief Marketing Officer & HR Lead, Offices.net
Understand Team Before Implementing Changes
Reflecting on my early days as a people manager, I learned a vital leadership lesson the hard way. At just 23 years old, I led a team of ten highly seasoned Field Salespeople. I was young, full of confidence, and eager to make an impact, so I dove headfirst into analyzing sales data and developing what I believed was a brilliant new commission structure. It was complex, designed to encourage the sales of less popular products, and even included a performance-based accelerator mechanism linked to customer feedback scores for each salesperson every quarter. I thought it was a great plan!
The MD presented my proposal to the board, which gained their approval and within a couple of weeks of becoming their line manager, I rolled out my new scheme to the field sales team. However, it was met with significant resistance and “went down like a lead balloon.” The sales team found the new scheme confusing, as it was complex and difficult to calculate, leaving them uncertain about their commission on each sale. While the scheme may have been fairer and more favorable for the business, my well-intentioned plan backfired spectacularly, as it had the adverse effect of being demotivational! Suffice to say we reinstated the old commission scheme within months.
Looking back, my enthusiasm outpaced my wisdom, and I failed to adequately consider the team’s perspective, needs, and established ways of working. What I learned was twofold. The first was that before implementing any changes, it is critical to take the time to “get under the hood” to understand the team and then communicate with them about their motivations and the problems a business faces before making any changes. Especially those impacting compensation! The second was that complex commission schemes breed confusion and ultimately undermine the motivation they seek to foster. I’ve subsequently helped hundreds of companies keep their commission schemes as simple as possible to be motivational.
Rob Scott, Managing Director, Aaron Wallis Sales Recruitment