The future of work is being shaped by two massive transformations: the shift to flexible work and the rise of generative AI. But how do organizations successfully navigate these changes without losing talent, productivity, or trust?
To answer this, we sat down with Brian Elliott, CEO of Work Forward, former Slack executive, and a thought leader in workplace transformation. With over 25 years of experience—from leading startups to driving innovation at Google and Slack—Brian has seen firsthand what works (and what doesn’t) when it comes to scaling distributed teams, embracing AI, and rethinking leadership.
In this conversation, Brian shares his biggest insights, why many companies fail at implementing change, and what leaders need to do to stay ahead.
And if you want to go even deeper, don’t miss his session at Running Remote 2025 (April 29-30 in Austin, Texas), where he will break down a step-by-step framework for adopting flexible work and AI successfully.
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Brian Elliott’s Journey: From Executive to Flexible Work Advocate
Q: Brian, you’ve had a fascinating career. What made you shift from being an operating executive to a leading advocate for flexible work?
“I sucked at being a manager,” Brian candidly admits. “One of my team members once pulled me aside and told me I was, well… let’s just say, not the best leader. That moment made me rethink everything.”
Brian’s turning point came from realizing that results matter more than physical presence. His early leadership struggles helped him develop a new mindset—one that prioritizes trust, flexibility, and clear outcomes over rigid work environments.
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How Enterprise Companies Can Successfully Implement Distributed Teams
Q: Enterprise companies have unique challenges when it comes to flexibility. What are the most effective ways to integrate distributed teams and foster collaboration across time zones?
Brian breaks it down into two major strategies:
✅ Episodic in-person connection – Instead of mandating office time, successful companies bring teams together quarterly to align on goals and strengthen relationships.
✅ Rethinking time zones – Teams should be intentionally structured to avoid extreme time zone gaps, and companies should invest in asynchronous collaboration tools to reduce meeting fatigue.
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RTO Mandates vs. Flexibility – Finding the Right Balance
Q: Your newsletter “Your CEO Wants to RTO” resonated with many. How can companies balance leadership’s desire for in-office work with employees’ need for flexibility?
Brian argues that rigid return-to-office (RTO) mandates fail because they don’t drive productivity—they drive talent away.
“No research has found that RTO mandates improve business performance. What we do see is that they increase attrition—especially for top talent and working parents.”
Instead of mandates or chaos, companies should develop team-level agreements that match the needs of their employees and business outcomes.
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Why Generative AI Adoption is Failing & How to Fix It
Q: In “GenAI’s Missing Ingredient,” you highlight the emotional aspects of AI adoption. What steps can leaders take to make AI work for people?
The biggest problem? Fear and lack of trust.
🔴 48% of employees are afraid to tell their boss they use AI – Many fear they’ll be seen as lazy or replaceable.
🔴 Companies are mandating AI use but failing to train employees – Employees aren’t sure how to use these tools effectively.
The fix? Creating clear team agreements on AI use. Brian suggests establishing norms for when AI can be used (e.g., for editing reports but not for writing performance reviews).
“Leaders need to make AI feel safe and beneficial—not like a threat.”
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The Leadership Shift: From IQ to EQ
Q: With AI and flexible work becoming dominant, how must leadership evolve?
Brian sees a fundamental shift in leadership:
- Less about IQ, more about EQ – AI can handle information overload, but only humans can build trust and culture.
- Clear decision-making is key – Leaders must be crisp about goals and priorities to keep teams aligned.
- Managers need real training – Only 25% of managers have been trained to lead remote teams effectively.
“Good leadership isn’t about watching over people’s shoulders—it’s about empowering them to do their best work.”
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The Key to Staying Ahead: Continuous Learning & Trust
Q: You’ve spent years researching and shaping the future of work. What are the biggest insights you’ve gained, and what must enterprise leaders do to stay ahead?
Brian boils it down to two critical elements:
- Continuous Learning – Companies need to embrace experimentation rather than waiting for a “perfect” model of remote work or AI adoption.
- Building Trust – Employees perform best when they trust their leadership, and leaders trust their employees in return.
“If you lose trust, you lose engagement. And once engagement drops, business results follow.”
At Running Remote 2025, Brian will dis
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The Link Between AI & Flexible Work: What Companies Are Missing
Q: Your Running Remote 2025 session explores the link between flexible work and AI adoption. What are the biggest parallels in how companies struggle (or succeed) with both?
Brian notes that companies make the same mistakes with AI and remote work:
🚫 Top-down mandates – Telling people to “return to office” or “start using AI” without investing in training leads to frustration and failure.
✅ Success starts with talent strategy – Companies that invest in employees (not just tools) are the ones that get results.
At Running Remote 2025, Brian will break down the four-step process for successfully implementing both flexible work and AI.
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Why Running Remote 2025 is a Must-Attend Event
Q: Brian, you’re a longtime Running Remote speaker. Why should people attend in April?
“This event isn’t just for thought leaders—it’s for the people actually making change happen.”
✅ Learn from top experts – Join leaders from Zillow, Twilio, Airbnb, Allstate, and more.
✅ Get real-world strategies – Walk away with actionable insights on remote, hybrid, and AI adoption.
✅ Connect with like-minded leaders – Build relationships with top HR, operations, and tech executives.
💡 Join us at Running Remote 2025, April 29-30 in Austin!
Register Now and secure your spot before tickets sell out!
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Your Journey Starts Here
Running Remote 2025 isn’t just a conference — it’s a movement. It’s where leaders like you come to find inspiration, build connections, and take actionable steps toward creating a better, more adaptable workplace.
By attending Running Remote 2025, you’ll position yourself as a leader ready to embrace change, foster innovation, and drive growth in your organization.
Join us in Austin on April 29-30, 2025, and be part of this transformative journey. Let’s shape the future of work together. Secure your Spot
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Register Now for Running Remote 2025 and Save 15% on your Tickets.
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