#44 – From the Trenches: Trusting Yourself in an AI World (Cass Cooper)

In this From the Trenches episode of the BMK Vision Podcast, Josh Peterson sits down with Cass Cooper—an interdisciplinary leader working at the intersection of organizational development, leadership development, AI, and cybersecurity—to explore a problem most MSP owners can feel but rarely name: in an always-on world, it’s easy to lose the ability to trust your own judgment.

This is not a conversation about “using AI better.” It’s a conversation about leading better—because the moment you outsource your decisions, your calendar, your boundaries, and your self-concept to whatever is loudest (clients, staff, inbox, social media, or now an LLM), you don’t just lose focus. You lose signal. Cass makes the case that what leaders actually need is not more output, but more white space—intentional room to reflect, recover, and recalibrate—so you can hear what you already know and execute it with discipline.

If you’re an MSP owner trying to build a healthier culture while also navigating AI, growth pressure, and constant operational noise, this episode will resonate. It reframes AI as a powerful partner—but warns against using it as a surrogate for identity, confidence, or leadership clarity.

What does it mean to “trust yourself” in an AI world?

For MSP owners, trust is usually framed as external: client trust, team trust, vendor trust, market trust. Cass pushes the conversation inward: leadership is also self-trust—the ability to make decisions without constant outsourcing, to hold boundaries under pressure, and to act on what you already know to be true.

AI can accelerate thinking. It can also quietly erode judgment when it becomes the default “validator” for every uncertain moment. The risk isn’t that AI gives bad answers. The risk is that leaders stop practicing discernment.

• Self-trust is a leadership capability, not a personality trait
• Decision clarity requires space—not just more tools
• AI works best as augmentation, not identity or authority

The real constraint isn’t time—it’s white space

Cass draws a sharp contrast between work cultures that normalize exhaustion and cultures that treat rest as part of the operating system. MSP leadership often rewards the opposite: heroics, over-scheduling, and constant reactivity. It “works” until it doesn’t—because the cost shows up as degraded judgment, short tempers, misaligned hiring, and leadership drift.

Her prescription is simple but uncomfortable: schedule blank space on purpose. Not to fill it with more tasks—but to restore the conditions where you can think clearly.

• Block time for reflection the same way you block time for client meetings
• Outsource low-joy work to reclaim energy—not to pack the calendar tighter
• Design rhythms that reduce leadership “noise” and increase signal

External validation is a leadership tax (and AI can amplify it)

One of the most important dynamics Cass names is the cultural habit of seeking external validation—especially for women, who are often socialized to defer to others for permission, certainty, and identity. For MSPs, the parallel is obvious: leaders who live in client approval, team approval, peer approval, or tool approval eventually build businesses that cannot hold a coherent point of view.

AI adds a new layer: it’s now possible to outsource not only decisions, but communication itself—emails, scripts, responses, positioning language—until you’re no longer sure what you believe versus what the machine produced. Cass’s warning is not anti-AI. It’s pro-agency.

• Validation loops create leadership fragility
• Over-reliance on prompts can replace clarity with plausibility
• Strong cultures require leaders who can decide, not just optimize

A practical “decision hygiene” framework for MSP owners using AI

If AI is part of your operating environment (it is), then the goal is to use it without surrendering leadership. Here’s a practical framework MSP owners can apply immediately:

• Use AI to expand options (brainstorming), not to pick your values (decision authority)
• Ask, “What do I already know?” before you ask a model
• Separate signal from noise: protect quiet time where your brain can integrate
• Keep a “human check”: major decisions require context a model doesn’t hold
• Build boundary defaults: do not let urgency dictate your calendar design

If you want a structured execution cadence that supports these habits—especially around leadership clarity, client experience, and operational consistency—BMK’s Vision platform is built to help MSPs align people, process, and performance without relying on heroics.

Episode highlights

• 00:00:11 – Cultural differences in work-life balance and how overwork becomes “normal”
• 00:01:12 – Cass’s multidisciplinary work across organizational development, AI, and cybersecurity
• 00:06:48 – What other cultures teach about rest, belonging, and sustainable rhythms
• 00:09:17 – Why leaders must schedule white space (and not backfill it with more work)
• 00:12:01 – How social conditioning shapes external validation and self-trust
• 00:21:08 – The upside—and the subtle risks—of using AI as a social and decision proxy
• 00:24:00 – Introducing Empressa AI and the idea of AI that supports (not replaces) inner knowing

About the guest: Cass Cooper

Cass Cooper is an interdisciplinary strategist focused on how modern work and technology shape identity, power, and belonging. With deep roots in organizational development and leadership development, she helps leaders create the self-awareness and operating rhythms needed to perform sustainably—without sacrificing health, clarity, or humanity.

Cass is also a collaborator with Empressa AI, a platform designed to blend expert human guidance with AI in ways that amplify agency rather than replacing it. Her work challenges leaders to “know better, do better” by building intentional space for reflection, decision-making, and boundary-setting—especially in environments where everything pulls attention outward.

🌐 Connect with Cass on LinkedIn →
🌐 Visit Cass’s website →

Frequently asked questions

How should MSP owners use AI without losing their leadership voice?
Use AI to generate options, structure information, and accelerate drafts—but keep values, judgment, and final decisions human and principle-driven.

What is “white space” and why does it matter for MSP leadership?
White space is intentionally unstructured calendar time that allows reflection and recovery. Without it, leaders become reactive, decision quality declines, and culture degrades.

Is relying on AI for decisions always bad?
No—AI can be useful for research and ideation. The risk is using it as a substitute for discernment, confidence, or identity, especially in high-context leadership decisions.

Why do MSP leaders struggle with boundaries?
Because urgency becomes a cultural default. Without an operating system and clear expectations, leaders absorb every escalation and train the organization to depend on heroics.

How does external validation show up in MSPs?
Leaders over-index on client approval, peer opinions, tool recommendations, or “what the market says,” instead of holding a clear internal point of view and executing consistently.

What’s a practical first step to rebuild self-trust?
Create a weekly block of protected white space, write down the decisions you’re avoiding, and start by answering: “What do I already know?” before seeking outside inputs.

Related resources from Bering McKinley

• Client engagement strategy for MSPs: from onboarding to QBRs
• The role of MSP sales consulting in revenue growth
• Support your support team by hiring a dispatcher

Want to continue the conversation?

If you’re an MSP owner building a culture that can scale—and want help creating clarity, discipline, and execution without sacrificing the humans inside the business—explore Vision or apply to be a guest on the podcast.

👉 Apply to be on the BMK Vision Podcast
👉 Learn more about Vision