Welcome back to Snafu w/ Robin Zander.
In this episode, I’m joined by Brian Elliott, former Slack executive and co-founder of Future Forum.
We discuss the common mistakes leaders make about AI and why trust and transparency are more crucial than ever. Brian shares lessons from building high-performing teams, what makes good leadership, and how to foster real collaboration. He also reflects on raising values-driven kids, the breakdown of institutional trust, and why purpose matters. We touch on the early research behind Future Forum and what he’d do differently today.
Brian will also be joining us live at Responsive Conference 2025, and I’m excited to continue the conversation there. If you haven’t gotten your tickets yet, get them here.
“Senior leaders sit on polar ends of the spectrum on this stuff. Very, very infrequently, sit in the middle, which is kind of where I find myself too often.”
Robin notes Brian will be co-leading an active session on AI at Responsive Conference with longtime collaborator Helen Kupp.
He tees up the conversation by saying Brian holds “a lot of controversial opinions” on AI, not that it’s insignificant, but that there’s a lot of “idealization.”
Brian says most senior leaders fall into one of two camps:
Camp A: “Oh my God, this changes everything.” These are the fear-mongers shouting: “If you don’t adopt now, your career is over.”
Camp B: “This will blow over.” They treat AI as just another productivity fad, like others before it.
Brian positions himself somewhere in the middle but is frustrated by both ends of the spectrum.
He points out that the loudest voices (Mark Benioff, Andy Jassy, Zuckerberg, Sam Altman) are “arms merchants” – they’re pushing AI tools because they’ve invested billions.
These tools are massively expensive to build and run, and unless they displace labor, it’s unclear how they generate ROI.
believe in AI’s potential and
aggressively push adoption inside their companies.
So, naturally, these execs have to:
But “nothing ever changes that fast,” and both the hype and the dismissal are off-base.
AI is materially different from past tech, but what’s missing is attention to how adoption happens.
“The organizational craft of driving adoption is not about handing out tools. It's all emotional.”
Adoption depends on whether people respond with fear or aspiration, not whether they have the software.
Frontline managers are key: it’s their job to create the time and space for teams to experiment with AI.
Brian credits Helen Kupp for being great at facilitating this kind of low-stakes experimentation.
Suggests teams should “play with AI tools” in a way totally unrelated to their actual job.
Example: take a look at your fridge, list the ingredients you have, and have AI suggest a recipe. “Well, that’s a sucky recipe, but it could do that, right?”
The point isn’t utility, it’s comfort and conversation:
What’s OK to use AI for?
Is it acceptable to draft your self-assessment for performance reviews with AI?
Should you tell your boss or hide it?
Robin brings up Ezra Klein’s podcast in The New York Times, where Ezra asks: “What’s the purpose of writing an essay in college?”
AI can now do better research than a student, faster and maybe more accurately.
But Robin argues that the act of writing is what matters, not just the output.
Says: “I’m much better at writing that letter than ChatGPT can ever be, because only Robin Zander can write that letter.”
Example: Robin and his partner are in contract on a house and wrote a letter to the seller – the usual “sob story” to win favor.
All the writing he’s done over the past two years prepared him to write that one letter better.
“The utility of doing the thing is not the thing itself – it’s what it trains.”
Robin’s fascinated by “skills that train skills” – a lifelong theme in both work and athletics.
He brings up Josh Waitzkin (from Searching for Bobby Fischer), who went from chess prodigy to big wave surfer to foil board rider.
Josh trained his surfing skills by riding a OneWheel through NYC, practicing balance in a different context.
Robin is drawn to that kind of transfer learning and “meta-learning” – especially since it’s so hard to measure or study.
He asks: What might AI be training in us that isn’t the thing itself?
We don’t yet know the cognitive effects of using generative AI daily, but we should be asking.
Brian brings up early research suggesting AI could make us “dumber.”
Outsourcing thinking to AI reduces sharpness over time.
But also: the “10,000 repetitions” idea still holds weight – doing the thing builds skill.
There’s a tension between “performance mode” (getting the thing done) and “growth mode” (learning).
He relates it to writing:
Says he’s a decent writer, not a great one, but wants to keep getting better.
Has a “quad project” with an editor who helps refine tone and clarity but doesn’t do the writing.
The setup: he provides 80% drafts, guidelines, tone notes, and past writing samples.
The AI/editor cleans things up, but Brian still reviews:
“I want that colloquialism back in.”
“I want that specific example back in.”
“That’s clunky, I don’t want to keep it.”
Writing is iterative, and tools can help, but shouldn’t replace his voice.
Robin shares a trick: he used em dashes long before ChatGPT and does them with a space on either side. He says that ChatGPT’s em dashes are double-length and don’t have spaces.
If you want to prove ChatGPT didn’t write something, “just add the space.”
Brian agrees and jokes that his editors often remove the spaces, but he puts them back in.
Reiterates that professional human editors like the ones he works with at Charter and Sloan are still better than AI.
Robin references The Gap by Ira Glass, a 2014 video that explores the disconnect between a creator’s vision and their current ability to execute on that vision.
He highlights Glass’s core advice: the only way to close that gap is through consistent repetition – what Glass calls “the reps.”
Brian agrees, noting that putting in the reps is exactly what creators must do, even when their output doesn’t yet meet their standards.
Brian also brings up his recent conversation with Nick Petrie, whose work focuses not only on what causes burnout but also on what actually resolves it.
He notes research showing that people stuck in repetitive performance mode – like doctors doing the same task for decades – eventually see a decline in performance.
Brian recommends mixing in growth opportunities alongside mastery work.
“exploit” mode (doing what you’re already good at) and
“explore” mode (trying something new that pushes you)
He says doing things that stretch your boundaries builds muscle that strengthens your core skills and breaks stagnation.
He emphasizes the value of alternating between
He adds that this applies just as much to personal growth, especially when people begin to question their deeper purpose and ask hard questions like, “Is this all there is to my life or career?
Brian observes that stepping back for self-reflection is often necessary, either by choice or because burnout forces a hard stop.
He suggests that sustainable performance requires not just consistency but also intentional space for growth, purpose, and honest self-evaluation.
On AI, Brian argues that most people get it wrong.
“I do think it’s augmentation.”
The tools are evolving rapidly, and so are the ways we use them.
They view it as a way to speed up work, especially for engineers, but that’s missing the bigger picture.
Brian stresses that EQ is becoming more important than IQ.
Companies still need people with developer mindsets – hypothesis-driven, structured thinkers.
But now, communication, empathy, and adaptability are no longer optional; they are critical.
“Human communication skills just went from ‘they kind of suck at it but it’s okay’ to ‘that’s not acceptable.’”
As AI takes over more specialist tasks, the value of generalists is rising.
People who can generate ideas, anticipate consequences, and rally others around a vision will be most valuable.
“Tools can handle the specialized knowledge – but only humans can connect it to purpose.”
Brian warns that traditional job descriptions and org charts are becoming obsolete.
Instead of looking for ways to rush employees into doing more work, “rethink the roles. What can a small group do when aligned around a common purpose?”
The future lies in small, aligned teams with shared goals.
Robin reflects on durable human traits through Steve Jobs' bio by Isaac Walterson.
Jobs succeeded not just with tech, but with taste, persuasion, charisma, and vision.
“He was less technologist, more storyteller.”
They discuss Sam Altman, the subject of Empire of AI. Whether or not the book is fully accurate, Robin argues that Altman’s defining trait is deal-making.
Robin shares his experience using ChatGPT in real estate.
It changed how he researched topics like redwood root systems on foundational structure and mosquito mitigation.
Despite the tech, both agree that human connection is more important than ever.
“We need humans now more than ever.”
Brian references data from Kelly Monahan showing AI power users are highly productive but deeply burned out.
40% more productive than their peers.
88% are completely burnt out.
Many don’t believe their company’s AI strategy, even while using the tools daily.
There's a growing disconnect between executive AI hype and on-the-ground experience.
But internal tests by top engineers showed only 10% improvement, mostly in simple tasks.
“You’ve got to get into the tools yourself to be fluent on this.”
One CTO believed AI would produce 30% efficiency gains.
Brian urges leaders to personally engage with the tools before making sweeping decisions.
He warns against blindly accepting optimistic vendor promises or trends.
Leaders pushing AI without firsthand experience risk overburdening their teams.
“You're bringing the Kool-Aid and then you're shoving it down your team's throat.”
This results in burnout, not productivity.
“You're cranking up the demands. You're cranking up the burnout, too.”
“That’s not going to lead to what you want either.”
Robin raises the topic of returning to the office, which has been a long-standing area of interest for him.
“I interviewed Joel Gascoyne on stage in 2016… the largest fully distributed company in the world at the time.”
He’s tracked distributed work since Responsive 2016.
Also mentions Shelby Wolpa (ex-Envision), who scaled thousands remotely.
Robin notes the shift post-COVID: companies are mandating returns without adjusting for today’s realities.”
Example: “Intel just did a mandatory 4 days a week return to office… and now people live hours away.”
He acknowledges the benefits of in-person collaboration, especially in creative or physical industries.
“There is an undeniable utility.”, especially as they met in Robin’s Cafe to talk about Responsive, despite a commute, because it was worth it.
But he challenges blanket return-to-office mandates, especially when the rationale is unclear.
According to Brian, any company uses RTO as a veiled soft layoff tactic.
Cites Elon Musk and Vivek Ramaswamy openly stating RTO is meant to encourage attrition. He says policies without clarity are ineffective.
“If you quit, I don’t have to pay you severance.”
Robin notes that the Responsive Manifesto isn’t about providing answers but outlining tensions to balance.
Before enforcing an RTO policy, leaders should ask: “What problem are we trying to solve – and do we have evidence of it?”
Performance data should guide decisions, not executive assumptions.
For instance, junior salespeople may benefit from in-person mentorship, but… That may only apply to certain teams, and doesn’t justify full mandates.
“I've seen situations where productivity has fallen – well-defined productivity.”
The decision-making process should be decentralized and nuanced.
Different teams have different needs — orgs must avoid one-size-fits-all policies, especially in large, distributed orgs.
“Should your CEO be making that decision? Or should your head of sales?”
Brian offers a two-part test for leaders to assess their RTO logic:
Are you trying to attract and retain the best talent?
Are your teams co-located or distributed?
If the answer to #1 is yes:
People will be less engaged, not more.
High performers will quietly leave or disengage while staying.
Forcing long commutes will hurt retention and morale.
If the answer to #2 is “distributed”:
Brian then tells a story about a JPMorgan IT manager who asks Jamie Dimon for flexibility.
“It’s freaking stupid… it actually made it harder to do their core work.”
Instead, teams need to define shared norms and operating agreements.
“Teams have to have norms to be effective.”
RTO makes even less sense.
His team spanned time zones and offices, forcing them into daily hurt collaboration.
He argues most RTO mandates are driven by fear and a desire for control.
More important than office days are questions like:
What hours are we available for meetings?
What tools do we use and why?
How do we make decisions?
Who owns which roles and responsibilities?
The Bottom Line:
The policy must match the structure.
If teams are remote by design, dragging them into an office is counterproductive.
“We’re living in a more chaotic time than any in my lifetime.”
Robin asks how leaders should guide their organizations through uncertainty.
He reflects on his early work years during the 2008 crash and the unpredictability he’s seen since.
Observes current instability like the UCSF and NIH funding and hiring freezes disrupting universities, rising political violence, and murders of public officials from the McKnight Foundation, and more may persist for years without relief.
“I was bussing tables for two weeks, quit, became a personal trainer… my old client jumped out a window because he lost his fortune as a banker.”
Brian says what’s needed now is:
Resilience – a mindset of positive realism: acknowledging the issues, while focusing on agency and possibility, and supporting one another.
Trust – not just psychological safety, but deep belief in leadership clarity and honesty.
His definition of resilience includes:
“What options do we have?”
“What can we do as a team?”
“What’s the opportunity in this?”
Brian recalls laying off more people than he hired during the dot-com bust – and what helped his team endure:
“Here’s what we need to do. If you’re all in, we’ll get through this together.”
He believes trust is built when:
Leaders communicate clearly and early.
They acknowledge difficulty, without sugarcoating.
They create clarity about what matters most right now.
They involve their team in solutions.
He critiques companies that delay communication until they’re in PR cleanup mode:
Like Target’s CEO, who responded to backlash months too late – and with vague platitudes.
“Of course, he got backlash,” Brian says. “He wasn’t present.”
According to him, “Trust isn’t just psychological safety. It’s also honesty.”
“When trust is there, the work is more fun, and the results are better.”
Robin offers a Zander Media story:
Longtime collaborator Jonathan Kofahl lives in Austin.
Despite being remote, they prep for shoots with 3-minute calls instead of hour-long meetings.
The relationship is fast, fluid, and joyful, and the end product reflects that.
He explains the ripple effects of trust:
Faster workflows
Higher-quality output
More fun and less burnout
Better client experience
Fewer miscommunications or dropped balls
He also likens it to acrobatics:
“If trust isn’t there, you land on your head.”
“Seldom wrong, never in doubt – that bit me in the butt.”
Brian reflects on a toxic early-career mantra:
As a young consultant, he was taught to project confidence at all times.
It was said that “if you show doubt, you lose credibility,” especially with older clients.
Why that backfired:
It made him arrogant.
It discouraged honest questions or collaborative problem-solving.
It modeled bad leadership for others.
Brian critiques the startup world’s hero culture:
Tech glorifies mavericks and contrarians, people who bet against the grain and win.
But we rarely see the 95% who bet big and failed, and the survivors become models, often with toxic effects.
The real danger:
Leaders try to imitate success without understanding the context.
Contrarianism becomes a virtue in itself – even when it’s wrong.
Now, he models something else:
“I can point to the mountain, but I don’t know the exact path.”
Leaders should admit they don’t have all the answers.
Inviting the team to figure it out together builds alignment and ownership.
That’s how you lead through uncertainty, by trusting your team to co-create.
Brian recalls the early days of Future Forum:
Slack was deeply office-centric pre-pandemic.
He worked 5 days a week in SF, and even interns were expected to show up regularly.
Slack’s leadership, especially CTO Cal Henderson, was hesitant to go remote, not because they were anti-remote, but because they didn’t know how.
But when COVID hit, Slack, like everyone else, had to figure out remote work in real time.
Brian had long-standing relationships with Slack’s internal research team:
He pitched Stewart Butterfield (Slack’s CEO) on the idea of a think tank, where he was then joined by Helen Kupp and Sheela Subramanian, who became his co-founders in the venture. Thus, Future Forum was born.
Christina Janzer, Lucas Puente, and others.
Their research was excellent, but mostly internal-facing, used for product and marketing.
Brian, self-described as a “data geek,” saw an opportunity:
In mid-2020, Future Forum launched its first major study.
Expected finding: employee belonging would drop due to isolation.
Reality: it did, but not equally across all demographics.
For Black office workers, a sense of belonging actually increased.
Future Forum brought in Dr. Brian Lowery, a Black professor at Stanford, to help interpret the results.
Lowery explained:
“I’m a Black professor at Stanford. Whatever you think of it as a liberal school, if I have to walk on that campus five days a week and be on and not be Black five days a week, 9 to 5 – it’s taxing. It’s exhausting. If I can dial in and out of that situation, it’s a release.”
Brian, Helen, and Sheela co-authored a book that distilled lessons from:
Slack’s research
Hundreds of executive conversations
Real-world trials during the remote work shift
One editor even commented on how the book is “more like a philosophy book disguised as a playbook.”
The key principles are:
“Start with what matters to us as an organization. Then ask: What’s safe to try?”
Policies don’t work. Principles do.
Norms > mandates. Team-level agreements matter more than companywide rules.
Focus on outcomes, not activity.
Train your managers. Clarity, trust, and support start there.
Safe-to-try experiments. Iterate fast and test what works for your team.
Co-create team norms. Define how decisions get made, what tools get used, and when people are available.
What’s great with the book is that no matter where you are, this same set of rules still applies.
“My job was to model the kind of presence I wanted my team to show.”
Robin recalls a defining moment at Robin’s Café:
Employees were chatting behind the counter while a banana peel sat on the floor, surrounded by dirty dishes. It was a lawsuit waiting to happen.
His first impulse was to berate them, a habit from his small business upbringing.
But in that moment, he reframed his role. “I’m here to inspire, model, and demonstrate the behavior I want to see.”
He realized:
Hovering behind the counter = surveillance, not leadership.
True leadership = empowering your team to care, even when you’re not around.
You train your manager to create a culture, not compliance.
Brian and Robin agree:
Rules only go so far.
Teams thrive when they believe in the ‘why’ behind the work.
Robin draws a link between strong workplace culture and…
The global rise of authoritarianism
The erosion of trust in institutions
If trust makes Zander Media better, and helps VC-backed companies scale —
“Why do our political systems seem to be rewarding the exact opposite?”
According to Robin, “We’re in a world where trust is in very short supply.”
Brian reflects on why authoritarianism is thriving globally:
The media is fragmented. Everyone’s in different pocket universes.
People now get news from YouTube or TikTok, not trusted institutions.
Truth is no longer shared, and without shared truth, trust collapses.
“Walter Cronkite doesn’t exist anymore.”
He references Andor, where the character, Mon Mothma, says:
People no longer trust journalism, government, universities, science, or even business.
Edelman’s Trust Barometer dipped for business leaders for the first time in 25 years.
CEOs who once declared strong values are now going silent, which damages trust even more.
“The death of truth is really the problem that’s at work here.”
Robin points out: Trump and Elon, both charismatic, populist figures, continue to gain power despite low trust.
Why? Because their clarity and simplicity still outperform thoughtful leadership.
He also calls Trump a “marketing genius.”
Brian’s frustration:
Case in point: Trump-era officials who spread conspiracy theories now can’t walk them back.
Populists manufacture distrust, then struggle to govern once in power.
He shares a recent example:
Result: Their base turned on them.
Right-wing pundits (Pam Bondi, Dan Bongino) fanned Jeffrey Epstein conspiracies.
But in power, they had to admit: “There’s no client list publicly.”
Brian then suggests that trust should be rebuilt locally.
He points to leaders like Zohran Mamdani (NY):
“I may not agree with all his positions, but he can articulate a populist vision that isn’t exploitative.”
Brian expresses frustration at the silence from people in power:
“I’m disappointed, highly disappointed, in the number of leaders in positions of power and authority who could lend their voice to something as basic as: science is real.”
He calls for a return to shared facts:
“Let’s just start with: vaccines do not cause autism. Let’s start there.”
He draws a line between public health and trust:
We’ve had over a century of scientific evidence backing vaccines
But misinformation is eroding communal health
Brian clarifies: this isn’t about wedge issues like guns or Roe v. Wade
The problem is that scientists lack public authority, but CEOs don't
CEOs of major institutions could shift the narrative, especially those with massive employee bases. And yet, most say nothing:
“They know it’s going to bite them… and still, no one’s saying it.”
He warns: ignoring this will hurt businesses, frontline workers, and society at large.
Robin brings up the Doomsday Clock:
Historically, it was 2–4 minutes to midnight
“We are 89 seconds to midnight.” (as of January 2025)
This was issued by the Bulletin of Atomic Scientists, a symbol of how close humanity is to destroying itself.
Despite that, he remains hopeful:
“I might be the most energetic person in any room – and yet, I’m a prepper.”
Robin shared that:
And in a real emergency?
You might not make it.
He grew up in the wilderness, where ambulances don’t arrive, and CPR is a ritual of death.
He frequently visits Vieques, an island off Puerto Rico with no hospital, where a car crash likely means you won’t survive. As there is a saying there that goes, ‘No Hay Hospital', meaning ‘there is no hospital’. If something serious happens, you’re likely a few hours’ drive or even a flight away from medical care.
That shapes his worldview:
“We’ve forgotten how precious life is in privileged countries.”
Despite his joy and optimism, Robin is also:
Deeply aware of fragility – of systems, bodies, institutions.
Committed to preparation, not paranoia.
Focused on teaching resilience, care, and responsibility.
Robin asks:
“How do you counsel your boys to show up as protectors and earners, especially in a capitalist world, while also taking care of people, especially when we’re facing the potential end of humanity in our lifetimes?”
Brian responds:
His sons are now 25 and 23, and he’s incredibly proud of who they’re becoming.
Credits both parenting and luck but he also acknowledges many friends who’ve had harder parenting experiences.
His sons are:
Sharp and thoughtful
In healthy relationships
Focused on values over achievements
Educational path:
“They think deeply about what are now called ‘social justice’ issues in a very real way.”
Example: In 4th grade, their class did a homelessness simulation – replicating the fragmented, frustrating process of accessing services.
Preschool at the Jewish Community Center
Elementary at a Quaker school in San Francisco
He jokes that they needed a Buddhist high school to complete the loop
Not religious, but values-based, non-dogmatic education had a real impact
That hands-on empathy helped them see systemic problems early on, especially in San Francisco, where it’s worse.
“We were terrified our kids would take their comfort for granted.”
Brian’s kids:
Lived modestly, but comfortably in San Francisco.
Took vacations, had more than he and his wife did growing up.
Worried their sons would chase status over substance.
But what he taught them instead:
Family matters.
Friendships matter.
Being dependable matters.
Not just being good, but being someone others can count on.
He also cautioned against:
“We too often push kids toward something unattainable, and we act surprised when they burn out in the pursuit of that.”
The “gold ring” mentality is like chasing elite schools, careers, and accolades.
In sports and academics, he and his wife aimed for balance, not obsession.
Brian sees promise in his kids’ generation:
But also more:
Purpose-driven
Skeptical of false promises
Less obsessed with traditional success markers
Yes, they’re more stressed and overamped on social media.
Gen Z has been labeled just like every generation before:
“I’m Gen X. They literally made a movie about us called Slackers.”
He believes the best thing we can do is:
Model what matters
Spend time reflecting: What really does matter?
Help the next generation define enough for themselves, earlier than we did.
Brian references Clay Christensen, famed author of The Innovator’s Dilemma and How Will You Measure Your Life?
Clay’s insight:
“Success isn’t what you thought it was.”
Early reunions are full of bravado – titles, accomplishments, money.
Later reunions reveal divorce, estrangement, and regret.
The longer you go, the more you see:
Brian’s takeaway:
Even for Elon, it might be about Mars.
But for most of us, it’s not about how many projects we shipped.
It’s about:
Family
Friends
Presence
Meaning
“If you can realize that earlier, you give yourself the chance to adjust – and find your way back.”
WorkForward.com
Newsletter: The Work Forward on Substack
“Some weeks it’s lame, some weeks it’s great. But there’s a lot of community and feedback.”
And of course, join us at Responsive Conference this September 17-18, 2025.
How Will You Measure Your Life? by Clayton Christensen
The Innovator’s Dilemma by Clayton Christensen
Responsive Manifesto
Empire of AI by Karen Hao
The Gap by Ira Glass
The Ezra Klein Show
Andor
Slackers
Bulletin of Atomic Scientists
McKnight Foundation
National Institutes of Health (NIH)
Responsive.org
University of California, San Francisco
