This month at Omnia, we’re tackling the topic of common mistakes leaders make and how to grow beyond them.
Nobody steps into a leadership role and handles everything perfectly the first time. There are just too many moving parts, too many facets of personalities, and too many paths to take. Missteps are inevitable, and they are arguably the best way to learn. You can study leadership theories, books, and practices, but nothing solidifies a leadership lesson quite as much as having to conduct damage control after taking the wrong action.
For me, my mistake was saying yes in the first place. I was a subject matter expert in a law firm where expansion was sudden and explosive. As the firm brought middle managers on board, they looked for people to lead smaller teams. When they asked me, I said yes because I wanted to help and because I was honored to be asked. But I’m not a leader, and I had no real aspirations to be one.
I quickly found I didn’t have the assertiveness needed to stand firm where I needed to and push back against the impossible expectations set for my team. The new title and slight pay increase was not worth my suffering, and I quickly realized I was, in fact, not helping. I asked for a demotion and moved to training, where I excelled. I truly believe asking for and receiving that demotion was the best money I’ve ever spent.
As this incident suggests, I’m not the best person to speak about real-life leadership mistakes, so I asked a dear friend who has been in leadership for over 20 years about his experiences. Interestingly, his story started much like mine, but unlike me, he persevered.
Leadership stories start with ambition. Mine started with reluctance.
I was thriving in a role where I knew my craft, cared deeply about staff and customers, and had built a process that made our work faster, clearer, and more responsive. My team trusted me because I didn’t just design improvements, I lived them alongside my team.
When a new organizational leader arrived, she noticed that clarity, energy, and customer focus. Months later, she offered me a role leading service quality across the entire organization.
That’s when I made my big mistake: I said yes.
I wasn’t trained in organizational development. I wasn’t certified. I wasn’t even sure I belonged in the room. I accepted the job anyway, believing I could “figure it out” the way I always had. What followed was a period of painful learning. I had no clear goals. I didn’t know how to ask for direction. I didn’t want to seem critical or ungrateful. I worked harder and longer, thinking effort alone would make me worthy of the title.
Meanwhile, staff across the organization were quietly struggling with the same confusion and fear I was hiding. They didn’t understand the changes. They didn’t feel heard. They didn’t want to complain. And customers were feeling the ripple effects.
That’s when my accidental leadership journey finally clicked into place.
I realized I could serve in this new role the same way I had served in my old one:
– by listening deeply
– by representing the customer with data, not emotion
– by supporting staff without encouraging rebellion
– by building trust through clarity, not authority
I became the person who could translate pain into insight, confusion into direction, and frustration into improvement. I didn’t learn these skills from a textbook. I learned them because I had to, because the alternative was letting people suffer in silence.
Looking back, I never would have chosen this path if I had known how hard it would be. But I’m grateful for where it led. The mistake of saying yes forced me to grow into a leader who understands people, systems, and change far more deeply than I ever expected.
And that’s the story I want to share:
Sometimes the leadership mistake isn’t doing something wrong. It’s stepping into something you don’t feel ready for. And sometimes that’s exactly what makes you the leader people need.
In reading my friend’s story, I am so impressed by his perseverance and tenacity. He pushed through and committed in a way I didn’t feel comfortable doing. He stretched far beyond his comfort zone and found success for himself and his team.
I also can’t help but wonder if his own leaders made a few mistakes.
Could goals have been clarified and communicated more explicitly?
Could someone have arranged for the training he needed to start with more confidence?
Could his own leader have helped him explore what he needed when he didn’t know exactly what to ask for?
Was he listened to deeply and supported the way he listened to and supported his team?
All these questions coalesce into one common leadership mistake: Believing the acceptance of a leadership role marks the end of a journey, instead of the beginning of one.
No matter how senior they are, leaders need support, whether it’s from the next level up, peers, network members, or mentors. Nobody should be living the adage, “It’s lonely at the top.”
What can you do to keep new leaders from feeling like saying yes was a mistake?
- Normalize the learning curve. Let new leaders know that uncertainty is expected and that asking questions is a sign of good judgment, not weakness. Your reassurance can ease pressure and build confidence early on.
- Support their thought processes and exploration. Rather than giving answers or directives, ask thoughtful questions that help them develop decision-making skills and trust their own judgment.
- Offer consistent, visible support. Regular check-ins, timely feedback tailored to the individual’s communication style, and availability (especially during challenging moments) signal that they are not navigating leadership alone and that their growth matters.
- Provide opportunities for self-reflection. Behavioral tools, like the Omnia Leadership Development Profile, offer insight into people’s specific traits, strengths and challenge areas. Using the profile in conjunction with our Leadership Coaching Guide provides targeted insight into how to motivate, communicate with, and develop each new leader based on their unique behavioral traits.
Omnia is here to help you set your new leader up for success and avoid the mistake of letting them sink or swim. Contact us today for more information about Leadership Development tools.
