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Executive Advisory for When
the Right Direction Isn’t Obvious

Clarity of direction and decision confidence for navigating growth, change, and your next chapter.

Managing uncertainty

without losing confidence

When decisions carry real consequences, speed alone isn’t the advantage.
Clarity is. Today’s leaders are expected to decide faster, with more information, more tools, and more opinions than ever before. AI accelerates analysis. Dashboards multiply. Options are endless. What doesn’t increase at the same pace is confidence in which direction actually makes sense.

Most leaders don’t struggle with capability or accountability. They struggle with the quiet gap between what looks reasonable on paper and what feels comfortable to commit to.

That gap shows up as hesitation, second-guessing, or defaulting to the most familiar option while telling yourself it’s the rational one.

My approach is about closing that gap.

Not by replacing your judgment.
Not by giving you answers.


But by helping you find clarity so you can make decisions you can stand behind, even when certainty isn’t available.

My role is to create the space and structure for that kind of thinking.
To pressure-test assumptions, surface blind spots, and slow the moment down just enough so you’re choosing deliberately, not reactively.

Because when clarity is present, confidence follows. And decisions move forward without spirals or shortcuts.

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Bespoke Advisory

Clarity Is Worth Investing In

Having an experienced leader to rely on for experience and provide the clarity to see what you are missing can help avoid months of wasted time and energy. This is exactly why my approach is a partnership. This is bespoke, intensive guidance from someone who has successfully scaled global businesses, and redesigned a portfolio career after 25 years in the global business world. No video courses. No surface-level fluff. Just the clarity you need to decide your next direction.

Custom Advisory Partnerships

Retainer Based

Unrestricted access for leaders who need a strategic sounding board in real-time. Zero friction, total availability. Length of retainer flexible based on needs.

30-Day Recalibration

A focused, thirty-day sprint to surface critical decision patterns and clarify key action items. Intensive, milestone-driven, and highly tactical.

The Inner Council

The ultimate network accelerator. Combines private 1:1 mentorship with vetted introductions to an exclusive leadership network.

What you get

  • Live 1:1 sessions to clarify your situation, pressure-test your thinking, and lock your direction

  • Identify the barriers driving indecision and inner conflict

  • Weekly check-ins and async access

  • Clarity on your new direction, and what you are building next

  • Proven methods for making effective decisions faster and stop second-guessing

  • Right sizing ambition and expectations for your next chapter

  • Accountability that quickly addresses your core challenges, identity blocks and a blueprint for what to build next with the steps required to make it a reality.

  • Customized approach to suit your specific situation, needs, and goals.

  • Typical retainer length is between 2-6 months with longer partnerships available.


Who it’s for

  • Senior leaders, founders, former founders or executive leaders

  • You feel stuck in indecision, uncertainty, or “what now?” ambiguity

  • You want a clear plan and personal guidance, not content to consume

  • You are willing to do individual work between sessions to build real clarity & momentum

  • You believe decision clarity in your next chapter is worth investing in long-term instead of a quick fix

  • You're looking to build a portfolio approach to what's next (Board membership, angel investing, passion projects, philanthropy, advisory, mentoring, or entrepreneurship.)


Who it’s not for

  • Anyone looking for therapy, crisis support, or emotional processing without decisions

  • People who want a done-for-you solution without doing the reflection and follow-through

  • Anyone expecting everything to be solved in 30 days

  • Leaders looking for help getting another job or start a job in a new industry


Why this is the right fit
This isn't generic advisory or mentorship. This is different. You get a true partner invested in what you're building, meaningful 1:1 support and guidance, plus a clear direction built around your real constraints, patterns, and priorities. If you want a grounded approach that restores confidence and momentum quickly, this is for you.

Limited Availability

Due to the high level of commitment required to ensure each of my clients receives the dedicated support they need to succeed, the number of available mentorship opportunities is limited. Typical openings are available every 2-6 months. 

Inner stability When faced with uncertainty

This is not therapy.
This is not generic life coaching.
This is identity work and legacy building.

I help people:

  • Allow doubt without collapsing into indecision

  • Provide guidance without you surrendering ownership

  • Navigate loss of status, structure and identity

  • Design a sustainable rhythm to avoid burnout

  • Find clarity and direction in the path forward and what's next

  • Detox beliefs of worth tied to productivity

  • Alignment of values to your authentic next chapter

  • Maintain decision ownership under uncertainty

  • Build a portfolio career (board membership, fractional roles, advisory, entrepreneurship, angel investing, philanthropy and mentorship)

  • Right‑sizing ambition and expectations

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Modern Meeting Room
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180 John St, Toronto, ON M5T 1X5

©KevinSimcock 2025. All Rights Reserved

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