New leaders often stumble through the same predictable traps, but the path forward becomes clearer when learning from those who’ve already made leadership mistakes. This article compiles 18 critical leadership missteps and the hard-won lessons that followed, drawing on insights from experienced leaders across industries. Whether you’re stepping into your first management role or taking on greater responsibility, these practical lessons can help you avoid common pitfalls and build stronger teams from day one.
- Pair Standards With Safety
- Quit Heroics And Grow Capability
- Favor Inquiry Over Solutions
- Make Yourself Replaceable And Elevate Others
- Hear Frontlines And Change Course
- Act Amid Uncertainty With Purpose
- Specialize Early For Distinct Value
- Prioritize People And Role Fit
- Protect Culture Over Star Output
- Measure What You Control
- Own The Frame With Clarity
- Ask Better Questions And Honor Expertise
- Explain Intent For Alignment
- Delegate Decisions And Authority
- Shift Spotlight To Your Team
- Lead With Why And Trust How
- Hand Off Work To Empower
- Set Structure And Step Back
Pair Standards With Safety
I was a fiery leader. High standards for myself. Even higher standards for everyone around me. And I’ll be honest, I was never, truly never, satisfied with the quality of work we produced.
Here’s what I didn’t understand back then: as a creator, as a leader, you develop taste before you develop skill. You can see what good looks like. You know what the work should be. But no matter how hard you try, you’re just not there yet. There’s a gap between your vision and your ability to execute it.
My teams had that gap. And I was relentless about it. I’d move the goalpost. I’d push for a higher standard. I’d express frustration when the output didn’t match what I knew was possible. It was tough love without enough love.
Looking back, I’d owe my early teams an apology. Not because the standards were wrong, but because I didn’t know how to build people up while pushing them forward. I had the intensity, but I lacked the empathy to communicate that the gap wasn’t a failure. It was just part of the journey.
Here’s what’s strange, though: years later, those same people come back to me. They say, “I did my best work with you. I learned the most when I was on your team. I held myself to a higher standard because of you.” And that’s the tension I had to sit with. The push created growth. But the way I pushed created pain.
What I’ve learned is that great leadership isn’t choosing between high standards and high support. It’s doing both. You can demand excellence and still make people feel like they’re enough right now. You can point to the gap and still celebrate the progress. The goal isn’t to lower the bar, it’s to help people believe they can clear it.
My advice to new leaders: Your intensity is an asset, but unchecked intensity becomes a weapon. Before you push someone, ask yourself: Have I built enough trust that this push will feel like belief in them, not criticism of them? Because the difference between a coach and a critic isn’t what they say. It’s whether the person on the receiving end feels lifted up or torn down.
Standards without safety create fear. Safety without standards creates mediocrity. Your job is to hold both, and that’s a skill that takes years to develop. Give yourself grace while you figure it out. I wish I had.
Fahd Alhattab, Founder & Leadership Development Speaker, Unicorn Labs
Quit Heroics And Grow Capability
Early on, I made the classic mistake of confusing being busy with being a leader.
When I first stepped into leadership, I thought my value came from doing more than everyone else — answering every question, fixing every problem, being the fastest responder in the room. If something went wrong, I jumped in. If someone struggled, I took the work back. It felt responsible. It felt heroic. It was also completely counterproductive.
The reality hit me when I realised my team had started waiting for me. Decisions slowed unless I was involved. People stopped thinking one step ahead because I’d trained them not to. I wasn’t leading — I was clogging the system. Multitasking is professional procrastination, and I was guilty of it.
What I learned is this: leadership isn’t about activity, it’s about impact. If you’re the smartest, busiest person in the room every day, you’ve built dependence, not capability. My job shifted from “doing” to setting direction, removing obstacles, and holding people to account — even when it was uncomfortable.
The advice I give new leaders is simple and often unpopular: stop rescuing. When someone brings you a problem, don’t solve it — ask what they think should happen next. Let them own the decision and the consequence. Stay available, but don’t stay in the middle.
You’ll feel slower at first. Your ego will itch. But if you want a team that can think, act, and lead without you, you have to step back early — not once you’re burnt out.
Sean McPheat, Founder & CEO, MTD Training
Favor Inquiry Over Solutions
Early in my leadership journey, I made a mistake that looked like strength but functioned like control: I believed my job was to have the answers.
I equated leadership with decisiveness, visibility, and problem-solving. When challenges surfaced, I moved quickly, sometimes too quickly, to provide direction, resolve tension, and keep things moving. On the surface, it looked like strong leadership. In reality, I was unintentionally limiting growth, both for my team and for myself.
The consequence wasn’t immediate failure. It was quieter. Team members became dependent instead of empowered. Good ideas stayed unspoken. People waited for direction rather than taking ownership. I remember a talented assistant principal waiting in my office to ask what I thought about a discipline issue, when he already knew the answer. That’s when it hit me: I wasn’t leading. I was bottlenecking.
What I learned, through frustration, feedback, and honest self-assessment, is this: leadership isn’t about being the smartest person in the room; it’s about creating the conditions for others to think, contribute, and grow.
The turning point came when I began shifting from telling to asking. Instead of jumping in with solutions, I slowed down and posed better questions. I paused. I listened. I gave people space to wrestle with problems and articulate their thinking. That change didn’t make leadership easier, but it made it far more effective.
Performance improved, engagement increased, and trust deepened, not because I worked harder, but because I stopped crowding the room with answers.
If I could offer one piece of advice to new leaders, it would be this: don’t confuse speed with effectiveness. Early on, the pressure to prove yourself can push you toward over-functioning. Resist it. Your role isn’t to remove every obstacle; it’s to help others build the capability to navigate them.
Ask more than you tell. Pause longer than feels comfortable. Let silence do some of the work.
The pitfall isn’t caring too little, it’s doing too much, too fast, for too long. Leadership grows when you shift from being the solution to building a system where solutions can emerge.
That lesson reshaped my leadership, and it’s one I wish I’d learned sooner.
Gearl Loden, Leadership Consultant/Speaker, Loden Leadership + Consulting
Make Yourself Replaceable And Elevate Others
One of the biggest mistakes I made as a new manager was trying to make myself irreplaceable. I took credit for successful projects, packaged my team’s insights as my own, and believed standing out to senior leaders would secure my role. In reality, it did the opposite — it slowed my growth and limited my team’s.
What I learned is counterintuitive: the fastest way to grow as a leader is to make yourself replaceable. The real leverage isn’t owning the spotlight; it’s building a team that performs without you. The first time I brought my entire team into a results review and made their contributions visible, two direct reports earned recognition. Within a year, one of them stepped into management. With a stronger bench, I was able to step back from execution and take on bigger organizational challenges.
My advice to new leaders is simple: resist the urge to hoard credit. Make your team the owners of outcomes and create opportunities for them to interact with decision-makers. When you do this, trust increases on both sides — your team trusts you for backing them, and senior leaders trust you as someone who develops talent.
If there’s one mindset shift that accelerates leadership growth, it’s moving from “How can I stand out?” to “How can I help others stand out?” That’s the shortest path to scaling your impact — and to earning the bigger opportunities you’re really after.
Scott Davis, Founder & CEO, Outreacher.io
Hear Frontlines And Change Course
One mistake made early on in my leadership journey was thinking leadership meant having a clear vision and pushing it forward without hesitation. Early in my leadership journey, my team was rolling out software for a large hospital. I had mapped out the approach and moved straight into execution. On the surface, things looked fine. Underneath, they were not. My team knew something was wrong, but I was not creating space to hear it.
The problem was that I focused on proving the plan rather than understanding reality. One of our engineers spoke up. He walked me through the daily friction users were facing and the workarounds the team had been quietly managing. This reality check made me stop right there. We paused, redesigned the solution around frontline input, and shipped again. The result was excellent as support tickets dropped by 30%. Customer satisfaction increased by 15%. The numbers mattered, of course, but the lesson mattered more.
One piece of advice I would give to new leaders is that leadership is not about having the correct answer from the beginning, but listening to the people closest to the work and acting on what they see. It requires asking uncomfortable questions and being willing to change course when the facts do not support the plan. When you listen carefully, invest in your team, and give them ownership, better outcomes follow. Leadership is not about proving you are right but finding the correct answer together.
John Russo, VP of Healthcare Technology Solutions, OSP Labs
Act Amid Uncertainty With Purpose
When I first became a line manager, I knew I wanted to lead by example, because all the good role models I had in mind did exactly that. Another strong belief I had was that good leaders were meant to be decisive.
The challenge was that seeing different sides of a decision or argument comes naturally to me. For every reasonable option, there are trade-offs. You gain some things, and you give others up. Who you hire, how you develop people, and what strategy is best. I wanted to be thoughtful and fair, but I was rarely 100 per cent convinced by my decisions, so I often took a long time to decide. I believed I was being responsible, but in reality, I was slowing things down and creating uncertainty.
It took me a while to learn that doubting a decision is human, and that being totally sure is neither normal nor healthy. Most meaningful decisions are made with incomplete information, and while taking time to think is important, waiting for full certainty can become a way of avoiding responsibility. In addition, most decisions are not irreversible or truly critical.
The advice I would give to new leaders is to accept uncertainty as part of the role. You do not need to be certain to be decisive. Make the best decision you can with the information available, explain your reasoning, and be open to revisiting it as new information emerges. This makes you human. I embody this approach in my role as COO at OXCCU, where we are scaling up new technology to produce sustainable aviation fuel. Every day, we navigate the uncertainty that naturally comes with turning science into engineering. Doubt never disappears, but learning to act responsibly in spite of it is what makes progress possible.
Nacho Gimenez, COO, OXCCU
Specialize Early For Distinct Value
Early in my transition from law enforcement to cybersecurity consulting, I tried to be everything to everyone. I’d take on any project — WordPress sites, network configs, general IT support — whatever came through the door. I thought saying yes to everything would build the business faster.
What I learned: I was burning out and not getting better at anything specific. My clients got decent service, but I wasn’t becoming exceptional at solving their real problems. And honestly, I was competing on price instead of value.
The turning point came when I lost a potential client to a firm that charged 3x what I quoted. They didn’t do more services — they just specialized in exactly what that client needed and could articulate the value clearly. That stung.
My advice to new leaders: Pick your lane earlier than feels comfortable. You don’t need to master everything before you specialize. Figure out what problem you’re uniquely positioned to solve — maybe it’s because of your background, your network, or just what energizes you — and get known for that one thing first.
For me, it was realizing my law enforcement background plus cybersecurity credentials meant I could serve public safety agencies and small businesses in ways others couldn’t. Once I narrowed my focus, everything got easier — marketing, pricing, client relationships, even hiring decisions.
You can always expand later. But trying to be a generalist when you’re building credibility just means you’re forgettable.
Edith Forestal, Founder & Cybersecurity Specialist, Forestal Security
Prioritize People And Role Fit
One of the biggest mistakes I made early in my leadership journey was not putting people first soon enough. Like many founders, I was deeply focused on our services, positioning, and growth. I treated team building as something that would “catch up” later. I quickly learned that this mindset can quietly stall a business, no matter how strong the strategy looks on paper.
As we began to scale, it became clear that growth doesn’t break systems; it exposes them. The biggest challenge we faced wasn’t market demand or execution, but building the right team in the right roles. I learned the hard way that a poor role fit can slow momentum, damage morale, and cost you great talent. I also learned that promoting top performers into leadership roles without considering whether they actually want or are suited to lead can hurt both the individual and the business.
The turning point came when I stopped viewing “team” as an HR function and started treating it as the core strategy. We became intentional about mapping strengths and gaps, designing roles around people rather than titles, and investing in clear communication, consistent feedback, and professional development. Bringing in strong talent leadership and involving department heads directly in hiring helped ensure alignment between role, culture, and capability.
My advice to new leaders is simple but often overlooked: prioritize people earlier than feels comfortable. Hire for strengths, not convenience. Don’t confuse technical excellence with leadership ability. Create an environment where people feel seen, supported, and challenged to grow. When you get the team right, everything else (performance, innovation, and results) follows.
Dani Peleva, Founder and CEO, Franchise Fame
Protect Culture Over Star Output
One mistake I made early in my leadership journey was tolerating a high performer who consistently created persistent friction within the team. The individual delivered exceptional results, so I justified the behavior longer than I should have. Over time, the cost became clear. Collaboration suffered, people became guarded, and the team started optimizing around the individual instead of the work. I learned that culture debt compounds faster than performance gains, and it is far harder to unwind once trust erodes.
The lesson was simple but uncomfortable: output does not excuse behavior. You can coach skill gaps, but you cannot outsource basic respect. Allowing exceptions, even for top performers, quietly resets the standard for everyone else.
My advice to new leaders is to define non-negotiable behaviors early and enforce them consistently. Give direct feedback quickly, set clear expectations, and act decisively when a line is crossed. In my opinion, protecting the team’s culture is a core leadership obligation.
Andrius Budnikas, Chief Product Officer, Gainify
Measure What You Control
One mistake that I made early on in my own leadership journey was worrying too much about whether or not people were happy. I have realized over time that employee happiness is not the responsibility of the leader or the organization; rather, each employee is responsible for their own individual happiness.
As a young leader, I was very focused on creating an excellent employee experience for the sake of having happy employees. I created opportunities for connection, encouraged colleagues towards personal and professional goals, and I often asked what would make them happier at work. No matter what I did, people would still express discontent or say that they were not happy with aspects of their roles. I invested a lot of time and energy into trying to create an environment with happy people, until one day I realized that I was striving for a result outside of my control. I learned that you can create the conditions for a great employee experience where employees can be happy; however, an employee’s own happiness is up to them.
I would advise new leaders to measure success by the results they can control. I recognize my responsibility as a leader is to achieve business results and to foster an environment where staff can be successful; however, it is the responsibility of each employee to decide if they choose to be happy in their role under those conditions. I can serve as a mentor, I can create opportunities for staff for development, and I can allow space for fun and levity in the pursuit of team objectives. I can continue to ask staff what they need to be successful, and I can encourage them to make it happen. And I can empower staff to take ownership of their own happiness.
Erin Gregg, SVP, The Nebo Company
Own The Frame With Clarity
Early in my leadership journey, I underestimated the power of framing. I assumed that if I was kind, responsive, and emotionally attuned, the work would naturally organize itself. I was wrong.
My misstep included sensitivity and kindness but not leadership. In an effort to be collaborative and supportive, I allowed my staff to shape the frame more than I should have. I listened deeply, but I did not anchor decisively.
Over time, this led to blurred authority, misalignment, and subtle but accumulating miscommunication. People were engaged, but unsure. Supported, but unclear. The absence of a clear frame inadvertently created more anxiety than it relieved.
What I learned is this: kindness without structure is not leadership; it’s abdication. And structure without empathy is control. The leader’s role is not to absorb everyone’s feelings or defer endlessly to consensus, but to hold the frame steady enough that others stay motivated, creative and can do their best thinking inside of it.
The way in which a leader frames a situation is powerful beyond measure. It is foundational, and without it, although you may be in charge, your leadership limitations simply won’t allow for the creation of a team. When framing is neglected or inconsistent, even highly capable people can become uncertain, reactive, or disengaged.
Effective framing is psychological containment: the ability to hold complexity, emotion, and ambiguity, while simultaneously directing and without collapsing into rigidity or chaos. Too rigid a frame can feel controlling or suffocating; too loose a frame creates confusion and anxiety.
Framing operates on multiple levels at once. It includes the narratives we reinforce about the work and the team, the emotional presence we bring into the room, and our ability to attune to what is actually happening beneath the surface. It requires empathy, but not indulgence; awareness of fear and desire, but not governance by them. Strong framing eases anxiety without removing responsibility. It grounds people while preserving freedom of choice.
The advice I would give new leaders is simple but demanding: own the frame. Your team doesn’t need you to eliminate discomfort; they need you to metabolize it and give it meaning. When you do that well, people feel safer, more engaged, and more empowered, not because you were nice, but because you were clear.
Louis Laves-Webb, Psychotherapist/CEO, Louis Laves-Webb, LCSW-S, LPC-S & Associates
Ask Better Questions And Honor Expertise
One of the mistakes I made early in my leadership journey was rooted in good intentions but caused harm. I jumped in with solutions far too often, solving problems for my teams. I told them what I would do, sometimes subtly, and sometimes more directly.
In doing so, I unintentionally stole their learning. I robbed them of the opportunity to wrestle with complexity and to grow into leaders themselves. I limited their creativity and stalled innovative problem-solving, not because my team lacked the ability, but because I didn’t know how to create the space for it.
What I’ve learned since is that leadership isn’t about having the best answers. It’s about asking better questions. Today, I lead with curiosity. I pause and ask open-ended questions. I invite perspectives that differ from my own and resist the urge to steer the room toward my conclusion.
My advice to new leaders is simple but not easy: when you feel the impulse to jump in, fix something, or smooth things over, pause. Surround yourself with people whose expertise is different from your own, and then let them use it. Growth doesn’t come from being rescued; it comes from being trusted.
Laurie Carr, Coach-Consultant-Connector
Explain Intent For Alignment
One mistake I made early in my leadership journey was assuming that clarity of intent automatically translated into clarity of execution. In the early years, I believed that if the goal was obvious to me, the team would naturally interpret it the same way. I focused heavily on outcomes and timelines, but spent less time explaining the reasoning behind decisions or the trade-offs involved.
The result was misalignment. Teams worked hard, but sometimes in slightly different directions. When challenges surfaced, people hesitated to flag them early because they were unsure whether deviations would be seen as resistance or incompetence. That hesitation slowed progress more than any technical limitation.
What I learned is that leadership is not about how clearly you think, but how clearly others can act based on what you communicate. Explaining the “why” creates ownership. It also gives people the confidence to raise concerns, suggest alternatives, and adjust intelligently when conditions change.
One piece of advice I would give to new leaders is this: do not mistake decisiveness for completeness. Making a decision is only the first step. Invest time in context, assumptions, and boundaries. When people understand the intent behind a decision, they can execute with judgment rather than instructions. That shift reduces dependency, improves resilience, and builds leaders at every level.
Payal Gupta, Co Founder, Tecknotrove
Delegate Decisions And Authority
One mistake I made early in my leadership journey was thinking delegation meant handing off tasks, while still keeping all the decisions to myself. In reality, I was just creating a longer feedback loop where everything still came back to me.
It slowed the team down. People would do the work, then wait. Or worse, they’d second-guess themselves because they knew I’d step in anyway. I didn’t realize it at the time, but I was quietly turning myself into the bottleneck.
Gradually, I started treating delegation as a transfer of ownership: being clear about outcomes, letting people decide how to get there, and being okay if their approach wasn’t exactly how I would’ve done it.
So, the advice I’d give new leaders is to trust your team with decisions, not just execution. It’s uncomfortable at first, but it’s the only way leadership actually scales.
Bob Schulte, Founder, BrytSoftware LLC
Shift Spotlight To Your Team
Growing up with a solid technical background, I always believed leadership meant being better than everyone else. One factor that may have contributed to this belief is that I personally didn’t like leaders who weren’t there for me when I needed them most to solve complex technical problems. So I mistakenly concluded that I don’t want to be one of them. I wanted to be someone who would be technically superior to avoid the same “eyeroll” from talented team members as my leaders did.
I couldn’t be more wrong with this assumption. Through ups and downs, I have learned the value of relationships. I have also learned that leadership is all about outshining, promoting, and highlighting others. It’s not about being technically superior, or for that matter, even superior. When you focus on being smarter than everyone else, you end up focusing on yourself. Leadership is all about shifting focus to others, their needs, their priorities, and their growth.
My best advice for new leaders would be to remove “I” from leadership and replace it with “YOU.” It’s all about them in leadership!
Lead With Why And Trust How
Early in my leadership journey, I thought being “hands-on” in every little detail made me a good leader. I was in the weeds all the time, fixing things, redoing things, thinking I was helping. What I didn’t realize was that I was actually slowing my team down and sending the message that I didn’t trust them. It’s a hard lesson to learn: being busy doesn’t equal being effective.
What I’ve learned is that leadership isn’t about doing everything yourself; it’s about creating clarity, trust, and space for others to own their work. My advice to new leaders is simple. Focus on the “why” and let your team figure out the “how.” You’ll get better results, and you’ll actually enjoy leading instead of constantly firefighting.
Biana Lerman, Co-Founder & COO, Your HubSpot Expert
Hand Off Work To Empower
I used to think that taking on more work myself was a sign of commitment. In reality, it just led to burnout and prevented my team from growing. I learned that true leadership isn’t about being the hero who does everything; it’s about empowering your team to succeed.
To new leaders: learn to delegate. Your job isn’t to do everything yourself; it’s to build a team that can. Trust them, give them ownership, and focus on clear communication. This is how you scale your impact and grow as a leader.
Janero Washington, Education Director, ACSMI I Cybersecurity Certification
Set Structure And Step Back
At first, I thought of leadership as a fire alarm that never went off. Every communication seemed important. I felt like I had to fix every problem. From the outside, it appeared like commitment, but on the inside, it was tiring and not possible to keep going.
The moment of clarity occurred without any alarm. I figured out that people had good solutions for themselves. They were just waiting for mine before they moved. That pause let me realise how much it cost to lead that way. I discovered that a leader who does everything teaches others to do nothing. Building the structure and then trusting it to hold is what gives you strength.
Here’s what I would tell new leaders. Make things clear. Give guidance. Step back on purpose. When you are the system, everything is up to you. The system stays up even when you take a break.
Zertashia Awan, Author- Toxic Resilience