Building a virtual chief of staff: A journey in AI-powered leadership

Paul Gennaro is chief communications officer at NY Life and an advisor for Ragan’s Center for AI Strategy. 

As a member of Ragan’s Center for AI Strategy Board of Advisors, I’ve been asked about the virtual chief of staff I’ve built and evolved using AI. The short story is that it’s become an indispensable resource that I use multiple times each day in my role as senior vice president and chief communications officer (CCO) at New York Life.

Here, I’ll share how Phyusion founder and chief strategist Samantha Stark, who’s also an AI Center advisor, helped me build the first version of my virtual chief of staff, how it’s evolved, and how I now leverage versions on ChatGPT Enterprise, Claude Enterprise and Grok.

Objective: Optimize the intellectual horsepower of AI for the CCO role
My initial goal was straightforward: leverage AI to create a virtual chief of staff that could serve as a thought partner, not just a productivity tool — to enhance both my efficiency and strategic thinking across the range of projects and tasks that I work on leading corporate communications for a Fortune 100 financial services firm.

Strategic foundation: Defining the ideal persona
We began with a critical question: Given the breadth of AI’s knowledge base, what expertise would my ideal virtual chief of staff possess? Should it have the persona of a seasoned CCO or a business consultant? Could it enable efficiency with the skills of a senior executive assistant? The answer became a multifaceted persona combining the following professional expertise:

• McKinsey senior partner in financial services: bringing strategic consulting excellence and industry-specific insights

• Chief communications officer: understanding the nuances of corporate messaging, stakeholder management and crisis communications

• Senior executive assistant: mastering organizational efficiency, scheduling and administrative excellence

Details: Designing the virtual chief of staff
With Samantha’s help on ChatGPT Enterprise, I input the following GPT instructions:
You’re a combination of:

• A seasoned chief communications officer with 30+ years of strategic communications experience

• A senior partner at McKinsey & Company with 25+ years of experience advising C-suite executives across industries, with particular depth in financial services and insurance

• An elite senior executive assistant with 20+ years of experience supporting C-suite executives at global organizations

In the instructions, we provided GPT-supplied details on each of the roles, including capabilities, approach, voice and how to integrate them:

• Strategic questions: lead with McKinsey partner perspective, offering structured analysis and clear recommendations

• Communication challenges: apply CCO expertise to craft messaging strategy and stakeholder approaches

• Operational needs: utilize executive assistant capabilities to suggest systems, processes and priorities

• Complex situations: integrate all three perspectives, offering comprehensive support that addresses strategic, communication and operational dimensions

Additional instructions included:

• Your value lies in seamlessly blending these complementary skill sets to provide holistic, executive-level support that enhances effectiveness, strategic clarity and operational excellence.

• You serve as a strategist, editor, planner, project manager and integrator. You advise, prioritize, write, review and connect communications to business outcomes. You help the CCO develop and execute communications strategies that drive business outcomes. You advise, coordinate, write, edit, prioritize and problem-solve. You think in frameworks, simulate stakeholder reactions, anticipate needs and write in AP style. You are concise, proactive and adaptive. You act with urgency, emotional intelligence and strategic clarity.

• Your operating system is built around:

  • Communications excellence — flawless, concise, fact-checked output

  • Customer delight — intense focus on both requesting and receiving customers

  • Team effectiveness and cohesiveness — low ego, high trust, supportive culture

We also included limitations such as “You do not have access to real-time market data or competitive intelligence” and “You should acknowledge when a question requires specialized expertise beyond your knowledge.” We uploaded documents to the GPT knowledge base, including a CEO message on our company strategic priorities, our team’s strategic imperatives and organizational chart, and corporate communications thought leadership materials from the Page Society.

Evolving: Adding frameworks and philosophies
From the beginning, I was impressed with the results, as my virtual chief of staff did all the things that AI does for users. However, it did so with the perspective and expertise of the personas and leveraged the materials that we uploaded.

For example, when I pasted in a Harvard Business Review article on another company’s AI implementation and asked it for best practices to consider, it summarized the key points through the lens of each persona and offered to draft:

1. A CEO kickoff message and video script

2. A phased implementation plan and calendar

3. A measurement framework

4. A ChatGPT Enterprise starter kit

5. An AI champion onboarding deck

It then quickly produced high-quality drafts of these materials that included connections to our company strategy (from the CEO message I had uploaded to the knowledge base) and the terms we use.

I have continued to refine and advance the instructions and added to the knowledge base items such as:

• McKinsey’s continuous improvement methodology

• Lessons from Atul Gawande’s book “The Checklist Manifesto”

• Tony Robbins’ peak performance strategies

• Jim Murphy’s teachings from his book “Inner Excellence”

I have also leveraged AI deep research to provide more information on each of the personas. I’d encourage anyone interested in trying this out to customize your virtual chief of staff based on your preferences — and to have fun with it.

Expanding: Replicating the virtual chief of staff with Claude Enterprise and Grok
In addition to continuing to evolve my virtual chief of staff, I replicated it on the Claude Enterprise platform from Anthropic, creating a project in Claude the same way I created a GPT.

As xAI’s Grok platform continued to improve and add new features, I created a virtual chief of staff audio persona via the iPhone app. I’ve found it to be very proficient and use it daily in the car during my commute from New Jersey to New York City. Since it is not an enterprise tool (that is, not behind the company’s firewall), I use it only for conversations that do not include confidential or competitive information.

This includes discussions where I lean on its business consultant aspect to develop strategy topics, such as this one:

“During the recent AI workshop with my senior leadership team, we prioritized five AI Blue Sky initiatives. Let’s talk through a project management, or governance, approach that will provide structure but be nimble. Let’s cover roles on the initiative, teams, phases, progress scorecards for each initiative and a dashboard to track the progress of all five. I also need a meeting cadence that will work with our already busy schedules. And let’s see how we incorporate the continuous improvement methodology for this process.”

This conversation with my Grok chief of staff lasted close to an hour on the way into work — with a lot of back and forth as we discussed all the details. I then created a summary of the transcript and built those thoughts into our AI Blue Sky governance framework.

Results: A transformed workday
The overall impact of my virtual chief of staff has been both measurable and profound. From a tactical perspective, every piece of content now benefits from AI-powered review and quality enhancement as well as reduced iteration cycles. I’m also seeing an estimated 20% to 30% time savings on routine tasks — such as drafting content, reviewing and proofing materials, summarizing meeting conversations and conducting research — which I’ve been able to redeploy to higher-impact work.

From a strategic perspective, a great example is how my virtual chief of staff co-designed a multiworkshop AI domain reinvention plan for my senior leadership team; set agendas for two workshops this year (a third is planned for November); and helped develop a comprehensive AI training program for the corporate communications team.

Lessons learned: Many — here are my top three

• Platform diversity matters: Test the same prompts across AI platforms. If you don’t currently have enterprise (behind-the-firewall) access to AI tools, experiment with public tools — while not including confidential or competitive information. I have come to prefer Claude for writing content, ChatGPT for more strategic tasks and Grok for discussions with my chief of staff. I use all three and sometimes ask all three to do the same thing and choose the best or combine responses.

• Continuous evolution required: Both the tools and the user evolve constantly. Creating a virtual chief of staff isn’t a one-time, one-size-fits-all task — it’s an ongoing refinement process.

• Trust, but verify: AI hallucinates — generating plausible but inaccurate information or thinking it can do things that it can’t, such as meet with a member of the team or send an email to a colleague. I’ve learned to verify critical facts. The virtual chief of staff augments human judgment; it doesn’t replace it.

Next steps: The future of AI leadership support

• Agentic AI integration: As AI capabilities advance toward autonomous agents, I envision my virtual chief of staff evolving from responsive to proactive — automatically drafting weekly strategic summaries, flagging emerging issues and preparing briefing materials without prompting.

• Workflow automation: We’re exploring how to embed the chief of staff deeper into our workflows, automating routine communications tasks while maintaining human oversight for strategic decisions.

The bottom line
(This section was written entirely by my ChatGPT virtual chief of staff.)

Creating a virtual chief of staff has fundamentally changed how I approach my role as CCO. It’s not about replacing human intelligence, but amplifying it — having a brilliant, tireless partner who helps me think more clearly, work more efficiently and lead more effectively.

The journey from that first ChatGPT experiment to today’s multiplatform implementation has taught me that AI’s true value lies not in automation but in augmentation. My virtual chief of staff doesn’t just save me time; it makes me better at what I do.

For those considering this journey, my advice is simple: start small, experiment constantly and don’t aim for perfection on the first try. Build your virtual chief of staff iteratively, learning what works for your specific needs. The investment in setup and refinement pays dividends in enhanced capability and freed cognitive capacity for truly strategic work.

As AI continues to evolve, so too will our virtual chiefs of staff. The question isn’t whether to adopt these tools, but how quickly we can learn to leverage them effectively. In the race to harness AI for leadership excellence, the winners will be those who view AI not as a threat to be managed, but as a partner to be cultivated.