People rarely put “leadership roles” at the top of the list of jobs AI is transforming. But the reality
is, AI is now changing more than how leaders work – it’s changing how they develop.
A growing number of CEOs and other executives are turning to ChatGPT and other Generative
AI tools as a kind of digital coach for guidance on everything from layoff announcements to
diversity communications to executive promotions. But this trend is creating a new kind of
leadership blind spot: leaders who sound polished, articulate and “on message,” yet operate
without true conviction.
The risk is subtle but profound. When executives start outsourcing reflection to algorithms, they
lose the discomfort that fuels growth: the hard questions, the uncomfortable accountability. The
human judgment-based challenge that turns insight into actual change.
Here is the truth: AI can accelerate preparation. It cannot replace the emotional intelligence,
intuition and human tension that define transformational leadership.
The AI Appeal Is Obvious… and Dangerous
Leaders gravitate towards AI coaching because it’s available 24/7, and never judgmental. It
provides immediate, articulate responses to complex situations. For time-starved executives
facing relentless pressure, the convenience is seductive.
Need to craft a message about restructuring? ChatGPT will draft it in seconds. Wondering how
to handle a difficult conversation with your board? The AI will offer frameworks and talking
points. Trying to articulate your leadership philosophy for an all-hands meeting? It’ll generate something that sounds visionary and polished.
The problem emerges in what gets lost in translation. AI optimizes for coherence and safety,
smoothing edges, avoiding controversy and producing outputs that sound professional but lack
the very qualities that make leadership transformative: courage, authentic vulnerability and the
willingness to stake a position that might be uncomfortable.
In coaching rooms worldwide, a pattern is emerging: leaders show up with AI-polished scripts
that read well but ring false. Because the algorithm that produced them has never had to look a frightened team in the eye, shoulder the consequences of a decision, or sit with the discomfort
of not having all the answers.
When “Perfect” Communication Backfires
Consider the CEO who used ChatGPT to prepare for a town hall addressing why the newly
announced executive team was entirely male. The AI’s version was carefully constructed: it
acknowledged the lack of representation, emphasized the company’s commitment to diversity, outlined existing programs and projected optimism about future progress.
It was perfect. And it was wrong.
When this CEO brought me the script, my feedback was blunt: I told him it sounded like you’re explaining why it’s okay. It’s not okay. You need to name that directly, commit to a specific timeline for change, and then get out of your own way.
The revised approach was uncomfortable. It required the CEO to sit with the inadequacy of the
current situation rather than buffer it with corporate speak. But when delivered, it created instant credibility. No backlash. No skepticism. Just a team that believed their leader was being honest about a real problem.
That’s the difference. AI can help you defend a position. Human coaching forces you to examine
whether it’s the right position to hold in the first place.
This is where trust is actually built. Leaders create and accelerate trust through uncomfortable,
challenging, and real conversations, not polished ones. The team didn’t need perfect messaging; they needed to see a CEO willing to acknowledge reality without deflection. That vulnerability and directness is what builds credibility with teams, boards, and stakeholders alike.
Three Ways AI Coaching Goes Wrong
I’ve had hundreds of coaching engagements, and three patterns keep surfacing in leaders
who’ve leaned too heavily on AI for development:
1) Executives outsource reflection instead of building peer relationships.
Real leadership development happens in the collision between your perspective and someone
else’s. When leaders use AI as their primary sounding board, they get pattern-matched advice instead of the specific challenge that comes from someone who knows their blind spots.
One executive used ChatGPT to process a difficult promotion decision involving an underperforming but politically connected leader. The AI provided a balanced framework. I
asked him, “Are you optimizing for politics or performance?” and that discomfort created movement.
2) Teams develop AI-generated “vision statements” that can’t imagine futures beyond
what’s already known.
AI is trained on the past. When leadership teams outsource visioning to AI, they end up with
statements that sound like every other company’s vision: coherent, comprehensive, and
completely uninspiring
3)High-potential leaders follow AI career advice so broad they burn out trying to ” do it
all “
Ask ChatGPT for career development advice and you’ll get an endless list. It”s all technically true and completely paralyzing. Human coaches help leaders make choices. AI democratizes
advice but dilutes focus.
.What AI Can”t Do, and Why It Matters
The fundamental limitation isn’t about AI’s capabilities. It’s about what leadership development actually requires.
ChatGPT can”t sit in weighted silence while you process a realization. It can’t read the micro-
expressions that signal you’re not being fully honest. It can”t build the relational trust that allows someone to tell you that your blind spot is showing.
Leadership development isn’t about information transfer. It’s about identity transformation. And
that requires human witness, human challenge, and human accountability. The most powerful
coaching moments happen when someone asks the question you have been avoiding and refuses
to let you off the hook when you try to intellectualize your way out of discomfort.
AI can accelerate your thinking. It cannot accelerate your growth.
The Path Forward: Integration, Not Replacement
Heading into 2026, the strongest leaders are using AI as a starting point and a first draft, not a
final answer. They’re leveraging AI to clarify their thinking, then using human coaching to deepen it.
The risk isn’t that AI will replace human coaches. The risk is that leaders will use AI to avoid the
very discomfort that creates transformation, and in doing so, become technically proficient but
emotionally disconnected from the people they’re meant to serve.
The next generation of standout leaders won’t be the ones who optimize every message
through an algorithm. They’ll be the ones who understand that real leadership still requires real
humans who are willing to challenge them, sit with them in discomfort, and hold them accountable.
