Episode #971 of the MSPi PrimeCast
Building a successful MSP requires more than technical expertise. Strong leadership, sound decision-making, financial awareness, and disciplined execution all contribute to long-term success.
In his conversation with Joey Pinz, Rob Gregory, Chief Information Security Officer (CISO) at Optiv, shares insights from his military service and cybersecurity career. His experiences offer eight practical lessons MSP owners and executives can apply to their businesses.
1. Lead People, Don’t Just Manage Tasks
Gregory distinguishes leadership from management. While managers oversee tasks and processes, leaders motivate people, provide direction, and help employees understand the purpose behind their work.
Drawing from his military experience, he emphasizes selfless service and the importance of helping teams understand organizational changes rather than simply directing them to follow instructions.
MSP Action: When introducing changes, communicate the business objectives and expected outcomes. Help employees understand why their contributions matter.
2. Invest in Employee Development
Gregory believes leaders should support employees’ long-term ambitions, even when those goals might eventually take them outside the organization.
He encourages development beyond technical expertise, including communication, public speaking, and leadership skills. Understanding where employees hope to be in five or ten years helps leaders support their professional growth.
MSP Action: Include career development conversations in employee meetings. Identify training and leadership opportunities that align with individual goals.
3. Make Decisions Without Perfect Information
During his military career, Gregory encountered a serious cybersecurity incident at a major military installation. With approximately 65–75% of the situation understood, he and another shift leader decided to temporarily shut down the affected environment.
Although the decision initially faced criticism, subsequent information supported their actions and demonstrated the importance of responding before a threat escalated.
His experience illustrates that leaders sometimes must act without complete certainty.
MSP Action: Establish clear incident-response authority and escalation procedures. Prepare team leaders to evaluate risks and make timely decisions when information is incomplete.
4. Use Backward Planning to Achieve Goals
One military practice Gregory continues using is backward planning: identifying a desired outcome and working backward to determine the necessary steps.
He describes applying this approach when pursuing a chief warrant officer position in the Army, identifying qualifications and milestones well before reaching his goal.
MSP Action: Choose a strategic objective, such as expanding services or developing future leaders. Work backward to establish milestones, resources, and deadlines.
5. Recognize Human Behavior as a Security Risk
Gregory identifies human behavior as a persistent cybersecurity vulnerability. Even sophisticated defenses can be undermined when employees unknowingly provide attackers with access or credentials.
He also explains how AI can strengthen social engineering by helping attackers create more convincing campaigns.
MSP Action: Reinforce security awareness, credential protection, and suspicious-request verification through ongoing employee education alongside technical safeguards.
6. Make AI Governance Practical
Gregory advocates involving technology, cybersecurity, legal, and operational stakeholders in AI governance.
He also warns that complicated approval processes can encourage unauthorized AI usage. Employees who cannot easily access approved tools may seek alternatives that bypass established safeguards.
Effective governance, in his view, requires balancing security with practical business needs.
MSP Action: Simplify AI tool requests and approvals while involving the appropriate stakeholders in evaluating security, compliance, and operational risks.
7. Understand the True Cost of AI
AI expenses can extend far beyond initial subscriptions or implementation.
Gregory shares an example involving a client’s engineer whose automated AI process accumulated a five-figure bill over a weekend while performing relatively basic checks.
He emphasizes the importance of understanding usage-based charges, governance expenses, and additional security requirements before evaluating AI’s financial benefits.
MSP Action: Monitor AI consumption, establish spending visibility, and evaluate total costs against measurable business outcomes.
8. Build Discipline Into How You Allocate Time
For Gregory, discipline involves intentionally balancing professional responsibilities with family, hobbies, volunteer commitments, and personal well-being.
Despite a demanding career, he emphasizes making deliberate choices about where his time goes rather than allowing competing responsibilities to dictate his priorities.
MSP Action: Review how leadership time is divided among operations, employee development, strategic planning, and personal priorities. Make adjustments that support long-term goals.
Applying Rob Gregory’s Lessons to MSP Success
Rob Gregory’s experiences reinforce an important principle: successful businesses depend on more than technology.
Developing employees, making informed decisions, planning ahead, understanding emerging risks, and managing resources deliberately can help MSPs build stronger organizations.
For MSP owners and executives, these eight lessons provide a practical framework for evaluating leadership practices, operational priorities, and future business decisions.
Catch the full conversation on MSPi PrimeCast Episode #971 and connect with Rob at https://www.linkedin.com/in/robcgregory/