High performers often fail in their first leadership role because the skills that earned them the promotion are not the skills the role actually requires. The transition from individual contributor to leader is an identity shift, not a skill upgrade, and it comes down to three things: redefining what hard work means, treating kindness as a leadership lever, and learning to blend candor with care.
All the way back in 2013, I interviewed for the IT Director role of an emerging oil and gas company. Walking up to the Chase tower in Downtown Houston I asked myself, “What am I doing?… I’ve never been a Director before…” As much as I would love to say the fear and doubt subsided when sitting down with the CEO and CFO… it didn’t.
Once we got started, I walked them through everything I had done up to that point. Building out the global IT infrastructure for another oil and gas company, around 32 acquisitions and integrations, an IPO, years of consulting work, and a team of about 23 people that I had led. Everything they were planning to do over the next decade lined up almost perfectly with what I had already been a part of, and on paper, I was the perfect fit for what they needed.
The problem, the real truth of it, was that I only understood the technology. I was not the leader that I had thought I was. Whenever I actually stepped into the role and started to truly wrap my arms around what it meant to lead as an executive, things changed overnight.
This was around that season of my life when I first started paying attention to people who were putting content out online, and one name that kept showing up for me was Gary Vaynerchuk. Most people know him for the hustle culture, the grind, the entrepreneurship stuff and on and on and on, but there were a few key lessons that he spoke on during that window of my life that resonated with me beyond belief, and they ended up stacking on top of each other to become the foundation of how I have led every team since.
I’m going to walk you through the three that mattered the most, because the leap from being the best IT engineer or the fastest individual contributor into actual leadership is more challenging than most people realize. A lot of the time your old identity (the one that got you here) is the very thing working against you.
How Hard Work Changes When You Move into Leadership
The first thing that I had to come to terms with was hard work. I want to be careful here because I am not saying hard work stops mattering when you step into a senior role. It absolutely matters, probably more than ever. What I am saying is that the nature of it shifts entirely, and if you do not recognize that shift, you are going to keep grinding at things that no longer move the needle.
For the first decade of my career, hard work meant output. How many systems I could design, how many projects I could push across the finish line, how many late nights I could grind through before everybody else in the office had even logged on. That was my whole identity. When I stepped into the IT director seat I tried to just do more of the same, but at a larger scale. It did not work. Honestly, there was no way it could, because the work that actually matters at this level looks completely different.
The hard work at this level is harder, and it is also far less visible. It is developing the people on your team. It is building accountability inside and outside of your function. It is sitting with uncomfortable conversations that you would rather escape into your inbox to avoid. Maybe the toughest part of all of it, it is the work that you have to do on yourself, learning to step outside your comfort zone, questioning the assumptions you have been carrying for years, and accepting that your job is no longer to be the strongest force on the team but to become a force multiplier for everyone around you.
So yes, you are still going to work hard, but it is going to be a different kind of hard, and the sooner you make peace with that, the sooner you start operating at the level the role actually requires.
Why Kindness Is a Leadership Lever, Not a Weakness
The second lesson was kindness. This one took me a while to come around on. Up to that point in my career, I genuinely viewed the people on my team as cogs in a machine. They had specific skills, I would deploy them when I needed to, and that was the system. That kind of philosophy will absolutely get you results for a while, but there is a hard ceiling on it, and the thing you never get to tap into is discretionary effort. The extra mile that people will only give you when they actually believe that you care about them as human beings.
Kindness is not weakness. It is a leadership lever. The more you lean into it, the more you start to realize just how much of an unlock it really is. When you operate from a genuine place of kindness, you earn the ability to be incredibly direct without it ever landing as aggression.
We have all seen the version of the toxic boss who screams at people and then defends himself with, well, I am just being direct. Yeah, and look at the wreckage left behind him. You absolutely can be direct, and at this level you have to be, but when that directness comes from a place of actually caring about the person sitting across from you, they are going to be open and receptive instead of bracing for impact. That is the difference, and it is enormous.
How to Have the Candid Conversations Most Leaders Avoid
This third lesson is the one that ties the first two together, and it is candor. This is the thing that most directors and vice presidents, and even C-level executives, find ways to avoid. They go quiet. They sidestep. They schedule around it and they hope it resolves itself. For years I genuinely could not understand why. I figured these were the strongest leaders in the building and surely they would be the most comfortable with the hard conversations. The reality I came to learn is the exact opposite. Most leaders are not avoiding the conversation because they do not want to have it… they are avoiding it because they have never actually been taught how to have it.
And this is exactly where kindness becomes the unlock, because when you blend kindness with candor, the entire dynamic of the conversation changes.
Think about the difference between walking up to a member of your team and saying, Jason, you are really screwing things up and I need you to get your act together, versus saying, Jason, I have been getting some feedback from people in the business and I am genuinely worried about you, I am wondering how you are feeling about all of this, are you aware of the dynamic that is showing up, and how can I best support you through it? It is the same underlying message, but the experience on the other end could not be more different. The person across from you knows that you are still being honest with them, but they also know that you actually care, and that is what makes them willing to actually hear what you have to say.
How Senior Leaders Manage Pressure Without Burning Out the Team
There is one more piece that I want to add here, because it ties everything I just walked through together. When you are operating at the senior level, especially inside of publicly traded companies or anywhere with a board and outside investors, there is a layer of external pressure that the vast majority of the people on your team are never going to see or feel. It is real, it is constant, and at times it is enormous, and you have to figure out how to reconcile that pressure with the long game that I am describing here.
The way I have come to think about it is that leadership at this level operates like an accordion. You lean in, you apply pressure, you ask the team to push a little harder for a defined sprint, and then once you clear the hump, you take a breath, you let the team take a breath, you rebuild the trust and the relationships, and you get ready for the next push. If all you ever do is squeeze, eventually there is nothing left to squeeze, and the leaders who invest in kindness and candor during the calm seasons are the exact same leaders who get the discretionary effort when the storm finally hits.
Why the Leadership Identity Shift Matters More Than the Title
Here is where this all lands for me more than a decade later. The real change was never about the title. It was about the person that I had to become in order to operate at that level, and you simply cannot brute force your way into senior leadership by doing more of what got you the director role in the first place. Your old identity will work against you every single time. The people on your team are not going to remember the projects you delivered or the systems that you stood up.
They are going to remember how you made them feel. They are going to remember whether you cared. They are going to remember the hard conversations and whether you actually had them, or whether you just quietly avoided them and hoped that nobody noticed.
So the question I want to leave you with is this. Of the three lessons in this article, the deeper hard work, kindness, and candor, which of these are you quietly depriving your team of right now, and what do you think it is actually costing them?
Frequently Asked Questions About the Leadership Transition for High Performers
Why do high performers often fail when promoted to leadership?
High performers fail in leadership because the skills that earned them the promotion (technical depth, individual output, raw work ethic) are not the skills the role actually requires. Leadership demands developing other people, having uncomfortable conversations, and operating as a force multiplier rather than the strongest individual contributor on the team. Most new leaders try to brute-force their way through using their old playbook, and it does not work.
What is the biggest mindset shift for new leaders?
The biggest mindset shift for new leaders is recognizing that hard work does not go away, it changes shape entirely. Output is no longer the primary measure of value. The harder and less visible work becomes developing people, building accountability across functions, sitting with uncomfortable conversations, and doing the internal work on yourself to step outside your comfort zone.
Is kindness a weakness in leadership?
Kindness is not a weakness in leadership, it is a lever. Leaders who operate from genuine kindness earn the right to be direct without their feedback landing as aggression. Kindness also unlocks discretionary effort, which is the extra mile team members only give when they believe their leader actually cares about them as people.
Why do most leaders avoid difficult conversations?
Most leaders avoid difficult conversations not because they do not want to have them, but because they have never been taught how. When candor is delivered without kindness, it lands as aggression. When kindness is delivered without candor, nothing actually gets resolved. The skill is blending the two so the message is honest and the person across from you knows you genuinely care.
How do senior leaders manage pressure without burning out their teams?
Senior leaders manage pressure through an accordion approach. You apply pressure for a defined sprint, then deliberately ease off, rebuild trust and relationships, and prepare the team for the next push. Leaders who only squeeze eventually have nothing left to squeeze. The leaders who invest in kindness and candor during calm seasons are the same ones who earn discretionary effort when the storm hits.
Ready to Make the Leap?
If any of this hit close to home, you are not alone. The vast majority of directors and senior leaders I work with at Wolf Executives are wrestling with this exact transition, and the ones who break through are the ones who treat it as the identity shift it actually is, not a skills problem to grind their way out of.
I am Sean Barnes, founder of Wolf Executives, based in Houston, Texas. I help directors and senior leaders make the leap to vice president and beyond, drawing on twenty years of operating experience across IT, HR, project management, ESG, safety, transportation, and leadership development, including dozens of acquisitions, integrations, and two IPOs. If you are ready to have a real conversation about where you are stuck and what it would take to get to the next level, reach out and lets talk.
