Simon Sinek: AI Can’t Struggle for You

In The Diary Of A CEO episode titled “Simon Sinek: You're Being Lied To About AI's Real Purpose! We're Teaching Our Kids To Not Be Human!”, world-renowned entrepreneur and optimism expert Simon Sinek delivers a passionate wake-up call. AI is not the danger. Forgetting what it means to be human is.

Simon Sinek, founder of The Optimism Company and bestselling author of Start With Why and Leaders Eat Last, argues that leaders today must protect and model the emotional, imperfect, and deeply human skills that machines will never replicate.

Here are five key themes from his conversation with host Steven Bartlett and why they matter more than ever in the age of AI.

1. AI is a mirror, just a reflection

“AI is a mirror, it reflects who we are,” Simon says. As AI shows up in meetings, messages, and management systems, the risk is not in the tech itself. The real danger is when we start believing it is more than a tool.

“AI does not have courage, or insecurity, or ambition,” he explains. “It does not have a sense of responsibility.” It can calculate. It can mimic. But it cannot care.

This is especially dangerous in leadership, where wisdom and ethics are shaped by lived experience, not algorithms. “We do not want to confuse intelligence with wisdom,” Simon says. “They are different things.”

2. You can’t delegate being human

Simon warns that AI is quietly permitting people to avoid hard emotions. “We can delegate heartbreak. We can delegate listening. We can delegate difficult conversations,” he says. But these are the very things that make us human.

Younger generations growing up with curated digital lives and AI companionship may lose their tolerance for real, messy, emotional experiences. “The goal is not to avoid the human experience,” he says. “The goal is to go through it.”

And as AI accelerates, human skills must be relearned. Listening. Apologizing. Feeling. These are no longer optional. They are the essential currency of trust and leadership.

3. Discomfort builds connection and growth

We often think of discomfort as something to design away. Simon flips that belief. “We grow muscles by creating micro-tears,” he says. “Progress requires strain.”

This is true for teams and leadership, too. People do not bond through comfort. They bond through challenge. Leaders are not built in perfect conditions. They are shaped by adversity, uncertainty, and emotional exposure.

Simon shares a truth we often overlook. “Wrong is easier.” When we make mistakes, we feel more real. And so do the people around us. Trust is not formed by perfection. It is formed through shared struggle and visible humanity.

4. Purpose comes from imagination

Simon shares a story of an airline employee working late during a flight delay. When asked why he cared, the man said, “Because I imagine my own family stranded at the airport.”

That is purpose. That is empathy. That is imagination. No AI can simulate that because it has not lived. It has not been fired. It has not been dumped. It has not been scared.

We connect to meaning through our stories, not our systems. You cannot code purpose. You have to feel it, imagine it, and live it. And that only happens when people are empowered to care.

5. Courage, not perfection, defines leadership

“The most important human skill AI cannot learn is courage,” Simon says. Courage is acting without certainty. It is choosing to lead through vulnerability, not control.

Simon makes a powerful point. People follow those who struggle visibly. It is not flawlessness that inspires trust. It is realness. “We connect through imperfection,” he says.

Leadership means going first. Not having all the answers, but being willing to speak up, show up, and be seen. “AI will not go first unless you tell it to,” he says.

In cultures shaped by automation and optimization, real leadership will be defined by emotional labor. Empathy. Listening. Apologizing. Setting boundaries. These are not soft skills. These are survival skills.

This is why authentic relationships, personal or professional, are built through shared experiences, not polished outcomes. That typo in the email. That awkward conversation. That moment of doubt. That is where the leader shows up. Not above others. But among them.

Bottom Line

Simon’s message is not about resisting AI. It is about remembering who we are.

In a world that optimizes for scale, speed, and safety, leadership still requires something unscalable: emotional courage.

Courage, empathy, imagination, and struggle are not outdated. They are the future of leadership. The workplace does not need perfect efficiency. It needs people willing to go first, to feel deeply, to own their mistakes, and to keep struggling.

Because that is how leaders grow.

​Watch the full conversation and see why Simon says struggle is what makes leaders truly human 👉​

🧠 Exercise for Leaders: Human Signal Audit

Look at your current workflows and AI tools across hiring, meetings, feedback, performance, and communication.

Ask yourself and your team:

• Where are we outsourcing emotional labor?
• What human signals are still present?
• What discomfort are we avoiding that’s actually meaningful?

Then: Run one meeting this week with no AI. No summaries. No prompts. No automation. Just people. Afterwards, reflect: What felt different? What felt more human?

I keep a close eye on what our Future Work Experts are thinking, saying, and questioning. I break down the key conversations and brainstorm practical steps we can take to move forward.

This week:

FLEXIBLE WORKSPACE

​Phil Kirschner: Lessons from a $500 Million Empty Office​

• Surat Diamond Bourse is the largest and emptiest office building in the world. With 6.6 million sqft and space for 150,000 workers, only 150 offices are in use.
• The solution? Future-ready workplace design: build for multiple futures, test before scaling, distribute decision-making, and prioritize agility over ambition. The winners are not those who predict perfectly, but those who can pivot quickly.

📝 Prompt: Before your next major workplace initiative, ask as a team:
- Reality Check: What assumptions are we making that felt bulletproof just a few years ago?
- Voice Check: Who will actually live and/or work in this space, and what do they really want?
- Escape Hatch: If our core thesis proves wrong, what’s Plan B?

​Explore how to avoid building the next $500M mistake 👉​

WORKFORCE TRANSFORMATION

​Sophie Wade: Your New Workforce Formula​

• Referencing the WEF Future of Jobs Report 2025, she notes 39% of current skills will be outdated by 2030, 70% of employers plan to hire for new ones, and 40% expect staff cuts tied to skill gaps.
• Her solution: build a fluid workforce blending employees, contractors, freelancers, fractional execs, and AI agents. Sophie’s 90-day blueprint moves from Assessment (skills audits, task redesign), to Strategic Design (role remapping, AI-human pilots), to Implementation (culture alignment, retraining).
• Companies like Ocado, Aviva, and AT&T are leading—automating processes, building digital fluency, and upskilling for resilience.

📝 Prompt: Today, schedule a 2-hour executive session to answer:
- What percentage of our workforce is full-time, freelance, or fractional?
- Where are our most urgent skill gaps?
- Who is accountable for AI integration and workforce strategy?

​Get Sophie's 90-day transformation blueprint 👉​

EMOTIONAL INTELLIGENCE

​Jason Averbook: Anxiety Signals We’re On Track​

• Anxiety is a signal, not a weakness, it highlights what matters most amid AI-driven change. Jason reframes AI anxiety as an identity crisis for leaders, not just a tech shift. Left unaddressed, it fuels quiet quitting, fake alignment, and contributes to the $300B stress-related loss in U.S. workplaces.
• His playbook: normalize uncertainty, create space for fear, and empower managers as emotional translators. Emotional intelligence is now a survival skill, essential for navigating fast-paced transformation.

📝 Prompt: Run a reflection session with your leadership team. Ask:
“What excites us about this shift — and what scares us?”“Where might fear be masking values, priorities, or care?”
Use those insights not to calm fear, but to move with it, because discomfort is often a sign you’re headed somewhere meaningful.

​Read Jason’s take on turning fear into fuel for real transformation 👉​

🔥 QUICK HITS:

​(Workforce Platforms) UKG Isn’t Playing Small Anymore // By Jess Von Bank​

• Jess Von Bank breaks down how UKG, under CEO Jennifer Morgan, is transforming into a global AI-first workforce platform. Beyond HR, UKG now supports planning, scheduling, and frontline enablement with conversational AI and predictive guidance at the core.
• With ServiceNow and other key partners, UKG expands reach and adaptability across large enterprises. This transformation positions UKG alongside Workday, SAP, and Microsoft as a true workforce operating system.

📝 Prompt: If your company were to operate like an AI-first platform tomorrow, which legacy habits, tools, or mindsets would need to be unlearned — starting with you?

​Read Jess’s full breakdown of UKG’s transformation 👉​

​(Real Estate Disruption) Agent Bosses Reshape Office Needs // By Antony Slumbers​

• AI agents automating workflows will reduce execution-role office demand by 30–60%, replacing rows of desks with collaborative, tech-enabled environments like project rooms and mentoring hubs.
• As agent boss models take hold, workspace strategy must shift toward supporting creativity, culture, and human-AI coordination.

📝 Prompt: How would your workplace look if 60% of execution work disappeared? Audit your space for what supports thinking, collaborating, and evolving, not just sitting.

​Explore how agent bosses are shrinking desk demand 👉​

​(AI Culture Shift) Who Are Your AI Champions? // By Anthony Onesto​

• GitHub Copilot boosted coding speed by 55.8%, Weave’s eNPS jumped 95%, and product quality rose by up to 60%—but many teams still stall on adoption.
• Anthony’s fix: appoint AI Champions, tailor literacy programs, embed AI into daily work, and launch internal hackathons. Culture change starts when early adopters are empowered and ROI is tied to productivity, satisfaction, and innovation.

📝 Prompt: Run a “Culture Check” workshop. Identify natural AI Champions, map excitement and resistance by role, and co-redesign one daily workflow with AI. Celebrate one small win weekly.

​Learn how to activate culture-driven AI adoption with Anthony 👉

I track what’s worth your attention—bringing you the news and updates that matter most to how we work, lead, and grow.

This week:

SKIP-LEVEL MANAGEMENT

​Managing Managers at Scale​

Former Square CPO Saumil Mehta shares how skip leads—those who manage other managers—are the backbone of scaling organizations.

• API Endpoint Experiment: Leaders should operate only through their managers to expose delegation gaps and avoid overreach.
• Avoid the Traps: Don’t undermine (overriding managers) or cover (hiding performance issues).
• TRM Framework: Use Task-Relevant Maturity to delegate based on context, and apply a 2x2 matrix (impact × uncertainty) to decide where to get involved.

A must-have blueprint for high-output leadership in complex orgs.

📝 Prompt: Run the “API Endpoint Experiment” with your leadership team:
Imagine you’re no longer allowed to speak directly with any individual contributors (ICs). For one week, all of your input, feedback, and strategic direction must flow exclusively through your direct-report managers.

​Learn how to level up your leadership by managing managers — start with Saumil’s API experiment 👉​

RELATIONAL LEADERSHIP

​Great Leaders See People​

• Only 39% of employees feel someone at work cares, and nearly 1 in 3 feel invisible—driving disengagement despite a booming $1B engagement industry.
• Noticing matters: Real leadership is built in small, consistent acts of attention and care—like how airline coordinator Tanya builds trust through real connection, not perks.
• Slow down to connect: Hurry and autopilot sabotage culture—leaders must be fully present, gather meaningful cues, and practice proactive compassion to show: “You matter.”

📝 Prompt: Whenever you’re checking in with a team member, anchor the conversation with a specific detail they’ve mentioned before.
For example: “Is the Q3 rollout going okay? I remembered you said prepping that deck was intense last week.”

​Read the full story on noticing better 👉​

WORKWEEK REDESIGN

​100-80-100 Productivity Model​

Juliet Schor’s study of 245 companies and 8,700 employees proves the 100% pay, 80% time, 100% output model delivers real gains—without added stress.

• Results: 20+ well-being metrics improved, burnout and resignations plummeted (some from 40% to 0%), and 90% kept the four-day week.
• Insight: Success didn’t depend on structure—deeper time cuts meant better results, no matter how the schedule was arranged.

📝 Prompt: If productivity could remain the same (or rise), what internal inefficiencies could you eliminate today to give your team back a full day each week?

​Read how less time drives better work 👉​

WISDOM WORK

​Beyond Knowledge, Toward Wisdom​

Joe Hudson highlights 3 human skills AI can’t replace:

• Emotional Clarity – feel, process, decide
• Discernment – clarity amid data overload
• Connection – trust via the VIEW framework (Vulnerability, Impartiality, Empathy, Wonder)

Companies like Microsoft and Google embed inner work:

• Satya Nadella's empathy-first culture → 10x market cap
• Google’s mindfulness training → boosts innovation & retention

Wisdom, not knowledge, is emerging as the strategic differentiator in the AI-native economy.

📝 Prompt: Which of these three capacities—emotional clarity, discernment, or connection—feels weakest in your leadership today?
Design one 30-day experiment to strengthen it using a real team context.

​Read why wisdom beats knowledge now 👉​

INTERNAL INNOVATION TEAM

​Breakthroughs Start With People​

Breakthroughs scale when CHROs treat innovation as a talent orchestration challenge, not just idea generation.

• Nestlé built Nespresso into a $6.5B brand by redefining competition and backing intrapreneurs.
• Collins Aerospace turned cockpit upgrades into a connected aviation ecosystem.

Empowering full-time innovators with capital, clarity, and startup-style speed lets legacy firms repeat success—not just stumble into it.

📝 Prompt: Which existing leaders in your org have the mindset and resilience to drive a zero-to-one innovation, and are you giving them the space and incentives to try?

​Read how CHROs unlock repeat innovation 👉​

🔥 QUICK HITS:

• ​New Rules for China Trade: Geopolitical tension is reframing Western policies toward Chinese companies into three types: techno-nationalistic (exclusion), techno-localistic (localization demands), and protectionist (tariffs/subsidies). U.S. and EU restrictions on Huawei, TikTok, and EV imports reflect rising concerns about national security, IP transfer, and innovation gaps. To adapt, Western executives must realign supply chains, leverage incentives, and consider selective Chinese partnerships—not decouple blindly.
• ​Musk Returns to His Companies: After a polarizing stint in government, Elon Musk has stepped down from DOGE and is now refocused on Tesla, SpaceX, and xAI. Tesla plans to launch a robotaxi ride-hailing service in Austin amid falling sales and shrinking market share, while SpaceX pushes toward a Mars test launch. Tesla stock rebounded above $1T market cap on news of his return, despite earlier board-level CEO succession concerns.