Gregory Frye
Strategic Advisor to Leadership Teams
I work with CEOs and leadership teams facing transition, rising complexity, or stalled momentum.
Transitions raise the stakes. Complexity multiplies the variables. Progress becomes harder to sustain.
Most leadership teams don’t stall because they lack intelligence, effort, or vision.
They stall because:
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critical assumptions go unchecked during moments of change
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teams interpret the situation through different mental models
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priorities compete instead of reinforcing a shared direction
The result is predictable:
momentum slows, trust thins, and execution becomes noisy instead of effective.
That’s when I’m brought in.
When Leaders Typically Call Me
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Leaders usually reach out during moments where pressure increases and the old ways of working no longer hold.
This often follows:
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rapid growth and rising complexity
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a funding round, acquisition, or leadership change
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a strategy that makes sense, but isn’t translating into action
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teams becoming defensive, siloed, or stuck in circular conversations
These aren’t communication issues.
They’re structural challenges in decision-making and alignment.
What I Actually Do
My work focuses on three things that matter most during periods of transition and pressure:
Surface what’s missing
Unchecked assumptions, conflicting interpretations, and strategic blind spots that distort direction.
Reframe decisions so teams can move forward together
Clarifying how choices are understood, discussed, and reinforced – so leaders act with coherence instead of friction.
Restore trust and momentum
Helping teams deliberately reassess and strengthen strategic choices as conditions change.
I give leaders a space to think without performing, while sharpening the questions that shape decisions, alignment, and follow-through.
The Advisor Leaders Keep Close
"I would hire Gregory any day of the week."
Scott DeMoulin - Founder & CEO at Destiny Training Systems
How I Work
I don’t enter leadership teams with predefined answers, playbooks, or frameworks. I enter through questions designed to surface signals organizations often overlook.
I pay close attention to how decisions are discussed, how leaders engage with each other, and where conversations reveal hidden assumptions, missing feedback loops, or priorities quietly pulling in different directions.
I look for patterns between behavior, strategy, and decision-making that usually only become visible after problems surface – often months or years later.
Strong leaders experience this process as clarifying and grounding. When integrity or incentives are misaligned – or hidden agendas are at play – the work can feel confronting, and it brings critical risks into view before they harden into structural failure.
This perceptual discipline is what I call Narrative Intelligence.
Engagement Style
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I work directly with founders, CEOs, and senior leadership teams during moments that require clarity, disciplined thinking, and deliberate decision-making.
Engagements are structured to create high-trust, focused working environments where complex challenges can be examined honestly and leaders can make strategic choices with confidence.
I work with a small number of leadership teams at a time.
Most engagements begin with a short diagnostic phase and continue as a 30-day or project-based advisory partnership, shaped by context and level of support required.
"Don't Hesitate."
"If you have a chance to work with Gregory, don't hesitate for even a moment to move forward. He will surprise and delight you in more ways than you could imagine."