Real Questions. Real Leadership.
Have a question about AI, business, teams, or the kind of leadership that still holds its value in an age of automation and acceleration? Join the conversation by posting your comment below. I look forward to your insights.
Leadership and AI
Q: What decisions should leaders never delegate to AI?
A: Anything involving moral judgment, accountability, or long-term identity must stay human. AI can model outcomes, but it can’t carry responsibility or context across time.
Q: How do you lead when AI sees more than you do?
A: You lead by asking better questions. AI can reveal patterns, but it can’t assign meaning or set direction. That’s your role interpret, decide, and take responsibility.
Q: Can a leader rely on AI and still be trusted?
A: Only if they stay transparent about how AI is being used. Trust breaks down when decisions feel outsourced or opaque. Leaders must keep the human layer visible.
Q: What’s the biggest leadership risk in adopting AI?
A: Speed without reflection. Many leaders rush to implement AI tools without asking what values or trade-offs they’re embedding. That’s not strategy—it’s abdication.
Q: How does AI expose weak leadership?
A: It removes the noise. With AI handling routine work, what’s left is pure judgment, vision, and ethics. If a leader lacks those, the gap shows fast.
AI and Business
Q: How is AI changing what gives a company a competitive edge?
A: Data and automation used to be differentiators. Now they’re baseline. The edge comes from how wisely leaders integrate AI with human judgment.
Q: What business functions are most at risk of AI overuse?
A: Anything involving people HR, marketing, decision-making. Over-automation here leads to tone-deaf culture, generic messaging, and poor moral choices.
Q: Can AI improve strategy, or just execution?
A: AI enhances execution first, but it also surfaces insights that can inform strategy. The risk is leaders mistaking correlation for causation and skipping critical thinking.
Q: Should CEOs personally use AI tools?
A: Yes. Leaders who don’t engage firsthand lose perspective. You can’t evaluate tools or challenge outputs if you’re relying on secondhand summaries.
Q: How should boards hold leaders accountable for AI decisions?
A: By asking who made the final call, what risks were considered, and what human oversight was involved. Delegating to AI doesn’t remove human accountability.
AI And Teams
Q: How does AI change what teams need from their leaders?
A: Teams need more interpretation, not just instruction. They want leaders who can translate what AI says into what matters, and protect what shouldn’t be automated.
Q: What happens when teams follow AI without questioning it?
A: They lose critical thinking. Over time, the team gets faster but less thoughtful. Leaders must model how to pause, challenge, and reflect.
Q: How can leaders keep collaboration strong when AI handles most tasks?
A: By shifting the focus from task to meaning. AI can do the work, but humans need to connect, debate, and align on why the work matters.
Q: Is it ethical to use AI to monitor team performance?
A: Only if it’s transparent and used for growth, not punishment. Surveillance breaks trust. Insight builds it—if it’s shared and co-owned.
Q: How do you lead a team that resists AI tools?
A: Don’t sell the tool. Clarify the value. Show how AI supports their thinking, not replaces it. Resistance often comes from fear of being made irrelevant.
Artificial Intelligence
Q: How should leaders stay informed about advances in AI?
A: By choosing a few trusted sources and setting regular time to review. The goal isn’t to know everything. It’s to stay literate enough to ask the right questions.
Q: Can AI fully understand human context?
A: No. It can analyze patterns in language and behavior, but it lacks lived experience, emotion, and moral perspective. That gap is where human leadership remains essential.
Q: What’s the risk of relying too much on AI-generated insights?
A: The risk is mistaking correlation for truth. AI can surface possibilities, but leaders must test for relevance, integrity, and long-term impact.
Q: How do I know if my organization is using AI responsibly?
A: Start by asking: Who has oversight? What biases are we accounting for? Are outcomes being reviewed by humans? If you can’t answer those, you’re not leading. You’re outsourcing.
Q: Should leaders use AI to guide people decisions?
A: AI can assist with data, but people decisions demand more than performance metrics. They require empathy, judgment, and the ability to weigh potential, not just output.
Leadership That Still Matters
Q: What makes a leader essential in the AI era?
A: Leaders matter when they bring what AI cannot. Moral judgment, emotional insight, and the ability to lead through complexity set them apart. The more technology accelerates, the more teams look for human clarity, not just algorithmic precision.
Q: Has AI changed the definition of leadership?
A: It’s clarified it. Leadership isn’t about being the smartest in the room anymore. It’s about being the clearest, most responsible, and most human.
Q: Are traditional leadership models still useful?
A: Only if they evolve. Hierarchies built for control don’t work in an environment that rewards adaptability, transparency, and speed.
Q: What will future leaders be measured by?
A: Their ability to navigate complexity, hold ethical lines, and lead teams through uncertainty—often with imperfect data and AI-driven ambiguity.
Q: What’s the most overlooked leadership trait right now?
A: Discernment. Not just knowing what AI can do, but knowing what it shouldn’t do—and having the courage to draw that line.
Ask Lolly
Have a question about Leadership and AI? Post it in the comments and I’ll respond directly.
Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR, Inc.com, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness has become a national bestseller.