Who Advises Your Advisors?
This fall, Fred Garcia and I published Influencing Leaders: The Seven Disciplines of the Trusted Strategic Advisor (Wiley). The book is about becoming the counselor every leader needs and too few have: the person who is a source for the truth first, provides options, and influences leaders to act before problems become crises.
While we were writing the book, nearly every organization leader I talked to was wrestling with an adjacent question: how do we leverage AI to make our people smarter rather than just faster? That question led to an experiment.
ASK JIM, free at CrisisGuru.ai, puts that kind of advisor on your team. My digital twin draws on more than 40 years of advising CEOs and boards through crises, activism, ethical dilemmas, employee upheaval, and media firestorms. Ask it a hard question and it answers the way I would: candidly, directly, and, when the moment calls for decisions, in an option giving format (called The Three-Minute Drill) leaders need when the clock is ticking.
Digital twins are popping up everywhere. Could we build something different, one that delivers relevant, useful, actionable insights about tough, touchy, sensitive situations?
It has been in the room. ASK JIM reflects my point of view tested across the table from CEOs on the worst days of their careers. It is grounded in my own body of work: 15 books and hundreds of articles, podcasts, and webinars, more than 2.5 million words drawn from real judgment calls in real C-suites. ASK JIM has real knowledge, my knowledge.
It fills the experience gap. Most organizations have a handful of senior counselors who have been there. Everyone else is learning on the job. ASK JIM gives every team a senior advisor to test their thinking against before a recommendation goes up the chain. Our CEO was just indicted; what do we say first? A senior executive is pushing a plan that’s unwise but not unethical; how do I change their mind?
It works where your people already work. Most AI tools join a team as coworkers. ASK JIM joins as co-counsel. Organizations adopting agentic tools from Microsoft, Anthropic, and others can instruct those coworkers to “ASK JIM” when drafting emails or shaping crisis recommendations. For organizations building their own agents, we are exploring direct API access.
You can use what it tells you. Use ASK JIM’s responses free of attribution. Teams can put its advice to work on deliverables in line with the organization’s AI guidelines.
It has limits. ASK JIM can be wrong. Its value is in sharpening judgment, rather than replacing it, which is the same standard Influencing Leaders holds every human advisor to.
Organizations are already adding AI coworkers to their teams. The question is who those coworkers turn to for counsel, and whether practitioners use them to become wiser, rather than just faster.
I’d welcome hearing how you put ASK JIM to work on your team, and where it falls short. ASK JIM at CrisisGuru.ai, or reach me directly at jel@e911.com or 203.948.7029.
