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Senior leaders plateau not from lack of ambition but lack of support. The October Group unpacks why — and what the leaders still growing are doing differently.
There is a conversation most organizations are not having. Not because they do not know they should be having it. But because having it out loud would require admitting something uncomfortable.
The leaders at the top are not getting what they need.
On May 20, The October Group brought together three of the most experienced practitioners in our network for a live panel on exactly this. Dr. Steven Jones, who has spent 25 years working with leaders inside the World Bank, NASA, the FDA, and the IRS. Dr. Yasemin Gokalp, a performance psychologist and emotional intelligence specialist who has built award-winning leadership development programs for executive teams in high-stakes environments. And John Ryabik, a strategist and executive coach with 20 years of experience in complex, high-accountability organizations including the Federal Aviation Administration.
What follows are the most important things that conversation produced. Not a summary. The actual insights, in the words of the people who said them.
Harvard Business Review calls it the invisible drop-off. The moment a leader reaches the senior level and the support structures around them quietly disappear. BCG puts it more bluntly: organizations stop investing in leaders at the very level where that investment is needed most. McKinsey's research on CEO performance found that leaders plateau not from lack of ambition, but from lack of intentional renewal.
The question we opened with was simple. Why does this keep happening?
Dr. Steven Jones went first.
“Every five to ten years, every leader should be in some level of shift and some level of learning. When we stop learning, we often create a bind for ourselves and disrupt the lives of the people we work with.”
He named the trap that most senior leaders fall into. They get good at what they know. They build systems around what they know. And somewhere in that process, the question of what they do not know stops feeling safe to ask.
The second part of the problem, which I added, is that we are all complicit in it.
We collectively hold an assumption that the leader knows. And because we hold that assumption, we do not offer executives development programs. We do not resource for it. We do not build structures to support it. And so the leader is placed in the spotlight where they are expected to know everything and never ask for help. And the system does not build it for them. And they do not ask for it. And we all participate in their isolation without meaning to.
Dr. Yasemin Gokalp brought the culture lens.
“The mastery myth is very dangerous for both team culture and organizational culture. It creates isolated leadership environments where executives carry the pressure alone. And employees look up to their leaders. When they see that their leader is isolated and supposed to know it all, they mimic that. It creates a cultural shift toward more defensive and less adaptable.”
When the leader performs invulnerability, the team learns to perform it too. The culture of the organization starts to reflect whatever the leader models. If the leader never admits uncertainty, neither does anyone else. If the leader never asks for help, the organization quietly learns that asking for help is a sign of weakness.
John Ryabik named the systemic dimension.
“Fear and scarcity thinking is driving a lot of inaction and investment right now. Many senior leaders do not believe they can or even should be focusing on their own learning, especially when the competitiveness and survival of their organization may be at stake. And they are really shooting themselves in the foot.”
He added something that nobody in most organizations wants to say out loud.
“I do not think we all believe that our senior leaders truly can or want to learn and change. So development gets focused elsewhere, hoping the problem will correct itself over time.”
Then he delivered the number that stopped the room.
Organizations in the United States collectively spend one to two hundred billion dollars a year on leadership development, and 75 percent of them would say it is not very effective.
“We are not doing something right here.”
The second thing the panel produced is a distinction that I believe is the most important one in leadership development right now.
Competence versus capacity.
HBR researcher Annie Peshkam makes this distinction with precision. Competence is the bundle of skills and frameworks a leader is expected to have. Strategy, vision, execution, communication. The things that got most leaders to where they are.
Capacity is different.
It is the ability to remain present when action will not resolve the tension. To connect with humans. To hold complexity and sit with uncertainty long enough for something new to emerge.
Most leadership development programs build competence. Almost none of them build capacity.
Dr. Yasemin Gokalp explained what that costs at the cultural level.
“Many organizations culturally reward capability over capacity. They reward speed, certainty, control, and technical expertise. So leaders build those things and get really good at them. And then the culture starts to reflect those same values. And the capacities that actually drive high performance end up in the second row.”
She cited research that stopped me cold.
A study of 48,000 leadership 360 reviews collected over 20 years found that leaders consistently overestimate their emotional intelligence skills the higher they climb.
Their technical skills are measurable and developing.
Their emotional intelligence is quietly decreasing.
And they do not know it.
Their self-reporting says they are strong on these skills. Their reviewers disagree. And the gap between what the leader believes about themselves and what the people around them actually experience gets wider and wider as they rise.
John Ryabik connected it to strategy.
“The hallmark of the most effective leaders is not their charisma, their vision, or their know-how. It is really their ability to understand and connect with their people, to help them sense emerging possibilities around them, and to co-create the future together.”
“It is that capacity that enables leaders to instill what I call strategic coherence in organizations, where they can align strategy, action, resources, and culture to make the team and the organization successful, even under pressure.”
He went further.
“A leader who does not have capacity rushes to decide. They sidestep difficulty to alleviate their own discomfort. And what you get as a result is fragmentation, inefficiency, tension, and disengagement in strategy formulation and execution.”
Dr. Steven Jones named what growing capacity actually requires.
“Executives get to hold the hole. Not solve it. Hold it. Thinking with people rather than for them. Creating containment around the unmanageable experience. Being willing to move what feels impossible into something thinkable and shareable with others.”
He offered a reframe on curiosity that I keep returning to.
“If I act as if I don't know, and that not knowing is okay, it helps the executive begin to open up more space. For themselves and for the people they work with.”
This is the thing the old model of leadership gets exactly backwards.
The assumption is that the leader's value is in having the answers.
The research and the practice both say the opposite.
The leader's value in complexity is in holding the space for the right answers to emerge together.
The third thread the panel pulled came from McKinsey's research on the CEO journey.
McKinsey maps the leadership journey into four seasons.
Stepping up, where the leader prepares for the role and begins to understand why they want it and what it actually demands.
Starting strong, where they transition into the role and build initial momentum.
Staying ahead, where they work to sustain success over an extended period.
And sending it forward, where they build the leaders around them and begin to think about succession.
The critical insight from the research is that the skills and behaviors that make a leader successful in season two are not the same ones that keep them ahead in season three.
There is a different set of capacities required.
And most leaders do not know that.
Nobody tells them the rules have changed.
John Ryabik described what season three looks like when a leader does not navigate it well.
“Leaders can get captured by their own success. They become overconfident and comfortable. Then, almost inadvertently, they wall themselves off from other people's input and feedback.”
“In strategic conversations, they may be paying less attention, asking fewer questions, getting impatient with the process. They start proposing or relying on outdated approaches. They stop reflecting.”
He quoted Adam Grant, professor at Wharton.
“Mental horsepower does not guarantee mental dexterity.”
The best leaders need to be able to rethink. To maintain versatility. To keep thinking like an outsider even after they have been inside for years.
Dr. Steven Jones offered a coaching perspective on what usually goes wrong.
“There is often a missing piece, which is: where is the leader really at? Getting clear about what the leader needs at this time.”
“Because when coaching stops after a year when people need it for five to six, they get left at stage two. And we do not want them to stay lost there.”
He said something that I think is the most honest description of what great leadership development actually looks like.
“There is not a universal excellence. There is the form that works best for that leader doing what they are meant to do, and doing it well.”
Dr. Yasemin Gokalp added a data point from her culture research.
“In a study of 48,000 leadership 360 reviews collected over 20 years, they found that leaders often overestimate the importance of emotional intelligence skills, such as understanding others, team-building, adaptability, and emotional awareness, the higher they go up in the organization.”
“Their blind spots increase. Their technical skills develop. Their emotional intelligence decreases. And they are not aware that is happening.”
Near the end of the panel we arrived at what I think is the hardest piece.
Unlearning.
Most of what senior leaders have built their success on, the confidence, the decisiveness, the willingness to act, has to be examined.
Not abandoned.
Examined.
Because what got them here may not be what is needed now.
Dr. Steven Jones described unlearning as:
“Choosing to release something that does not have value for us anymore. And as we determine what that looks like, we decide there is something we need more.”
Dr. Yasemin Gokalp was direct about what the most important unlearning is at the senior level.
“The mastery myth. I know it all. I have learned it all. I am supposed to be all-powerful.”
“We know it is lonely out there. You know it is lonely. And you need support. People's ability to feel vulnerable dictates how much they can combat this mastery myth.”
She quoted Rumi.
“The heart is a sea, the language is the shore. Whatever is in the sea hits the shore.”
Whatever is inside the leader eventually shows up in the culture. In how people speak to each other. In how decisions get made. In whether a team feels safe enough to bring the real problems to the surface.
John Ryabik named what unlearning looks like in practice.
“What can you stop? Where could you hand something off? Where could you make more time for yourself so you can actually think about who you are, who you are becoming, what impact you want to have, what you need to let go of?”
“You are never going to be able to explore that if you are constantly in motion.”
He brought in Marshall Goldsmith.
“Consider picking one potentially annoying behavior you have and just stop it.”
“Maybe it is always feeling the need to respond. Giving your two cents when someone asks for your opinion and then immediately offering it before they have finished processing. Let it land. Stop filling the silence.”
The panel closed with the most practical question.
With everything we have discussed, what could a leader actually do differently starting this week?
Three answers. One from each panelist.
Dr. Steven Jones said start with a personal inventory.
“Where am I at in my life at this point? What are three things that are calling to me about the life I have and the life I want?”
“And then think about your people. What do they need to know so that they can support you?”
“Have you thought about who the people are in your life who hold the space for you on a regular basis? If you have not started building those relationships, start seeking them out.”
Dr. Yasemin Gokalp said go back to your last 360 review.
“Read it again, this time paying close attention to the blind spots.”
“Not the scores that made you proud. The ones that were easy to brush under the rug.”
“The research is very clear. Those blind spots are real. And if you have a blind spot on a particular competency, you are setting the culture of your organization with a low threshold on that competency.”
John Ryabik ended with a set of questions he recommends every leader ask regularly, not once.
Ask your direct reports, your employees, your customers.
“What are our customers asking for that we currently deliver?”
“What needs to be true for us to win?”
“What data proves our current assumptions are wrong?”
“What changes in the market require us to pivot?”
“And, most importantly, what is no one telling me that I need to hear?”
That last question is the one I want to leave you with.
What is no one telling you right now that you need to hear?
Not the version you would share in a board meeting.
The version you sit with at the end of a long week when you are being honest with yourself.
That question is where the work begins.
Dr. Philipia Hillman is the Founder and CEO of The October Group, a Washington DC-based firm that partners with C-suite leaders and their teams to align leadership, strategy, and culture so growth becomes sustainable.
The October Group panel “The Leadership Development Gap No One Talks About - And What Actually Closes It” took place on May 20, 2026.
The replay is available at https://www.theoctobergrp.com/the-leadership-development-gap-replay.
The October Group panel drew on research from Harvard Business Review, Boston Consulting Group, and McKinsey. The four source articles are available upon request.
