The Transform Dialogues: People, Culture & The Future of Work with Brian Elliott

Original Event Date:
October 30, 2025
5
minute read
The Transform Dialogues: People, Culture & The Future of Work with Brian Elliott

In this Transform Dialogues conversation (recorded live at Transform), Zech and Amy sit down with Brian Elliott, a seasoned tech leader and workplace strategist who’s led product teams and business units at Google and Slack, founded a 2020 think tank on flexible work, and now advises companies through Work Forward.

Together they unpack the hard truths of return-to-office mandates, the realities of hybrid at scale, and what it actually takes to unlock performance and belonging in a distributed world. Brian cuts through myths with data and practical examples, showing why outcomes beat mandates, why frontline managers are the make-or-break layer, and how to drive real adoption of generative AI without spooking your workforce. If you’re steering culture, talent, or transformation in 2025, this one’s a masterclass in building a modern operating system for work.

What we cover

  • RTO vs. reality: Why top-down “back to the office” edicts often fail—and how to design office time around specific outcomes (collaboration, onboarding, mentorship) instead of nostalgia for 2019 floor plans.
  • Hybrid at scale: When co-location helps (e.g., junior sales teams) and when it slows you down (time-zone-spanning teams); why regional patterns beat one-size-fits-all rules.
  • Manage to outcomes, not presence: Shift from activity monitoring to clear goals, shared rituals, and visible progress; make the office a tool, not a proxy for performance.
  • Frontline managers as force multipliers: The critical (and underinvested) layer—equip them with coaching skills, facilitation tools, and lightweight operating rituals.
  • AI adoption that sticks: Many orgs see only ~⅓ of employees using gen-AI regularly, with a silent segment afraid to disclose usage. Create safety, clarity, and incentives tied to real work outcomes.
  • Trust, well-being, and resilience: How leaders model psychological safety and set “floors” for ways of working—especially during prolonged uncertainty.
  • Practical playbook moves: Pilot-then-scale, publish team working agreements, time-box experiments, reward outcome achievement, and measure what the office (or AI) actually improves.

Why it matters

Performance in modern orgs isn’t a place; it’s an operating system—clear outcomes, empowered managers, intentional in-person moments, and AI embedded where it creates unmistakable value.

Click here to read the full program transcript

Transform Dialogues — Featuring Brian Elliott

All right.

We are here for the Transform Dialogues, part of the People Strategy Leaders podcast live at Transform.

My name is Zach.

I'm Amy, and we're joined by Brian Elliot.

Brian Elliot.

Yep.

Thank you for being here with us.

Thanks For having me.

Guys, This is, uh, a really exciting day here at Transform.

There's a lot of things going on within the world of work.

I feel like the conversations have been pretty wild here so far.

Yeah.

And, uh, yeah.

What the hell is going on?

What are some of the things you're experiencing seeing and Talking about?

Yeah.

Give, I'll give you the quickie background, just so all know who I am more broadly.

So I lead a group called Work Forward.

We're an advisory firm on future work topics.

I spent 25 years in tech myself as a leader like startup, CEO, Google, and Slack leading product teams and business units, and then started a think tank in 2020 that studied flexible work.

I spent a lot of time with like chief people, officers, heads of workplace, heads of it, talking about like, how do you enable your teams to get through change and turmoil?

So that's been return to office and where are we on that battle on a nonstop basis for five years.

Basically, it comes and goes, uh, last year plus it's been generative AI and what actually works from an adoption perspective.

And then both of those things that were sort of super hot and topical still at the end of the year have kind of a little bit fallen by the wayside, even in these conversations here to kind of go, what the heck is going on in the world around us?

Right?

So a lot of chaos concerns about a recession that are moving into concerns about stagflation and real deep concerns about how my employees doing through all of this because it's major turmoil.

So glad to talk about any of those three themes and more.

Let's start that back.

I'd love to start with maybe the return to office piece.

Sure.

And right.

'cause we've been, through the last five years, COVID opened up this incredible opportunity for companies to evaluate remote work Yeah.

And force them into it.

Right.

And, and it opened up now this whole potential for companies, right?

Yeah.

And now we're also seeing this wave now of return to office.

Yeah.

In some ways it feels very forced and, uh, uh, I, I don't know the, maybe the, maybe we can speak to this, like where are some of the reasoning or urge to return to office is coming from Yeah.

When we have found that it's a pretty engaging strategic move to stay hybrid or remote.

Yeah.

So it's like, why are some of these mandates or like at a return to office, uh, push happening so aggressively for some companies?

Yeah.

Um, are we unaware of some type of like, strategic advantage that this comes with?

Or am I simplifying it where it's like, yeah, I don't know.

Like what Yeah.

What's going on?

Mess of the, the headlines get, tend to get written by the people who are being the most extreme and changing their minds the furthest, right?

Yeah.

So Amazon coming outta the pandemic said, Hey, we're gonna be virtual first.

We're gonna let, uh, directors figure out what's the right pattern for their team.

Then they went to three days, then they went to five days, right?

Uh, Jamie Diamond may have all their ulterior motives to some degree.

I actually believe him gen that he believes genuinely it's the right answer.

But that's part of what you're seeing is it's CEOs, especially when it's a five day mandate, it's very often the CEO themselves who's saying, this is the right answer and it's the right answer because this is how I came through the system.

This is what made me successful.

And there's also some underlying issues and challenges that we can get into.

But that's a big part of this is like, I want the, I, I actually genuinely may believe it, but it's also based on my understanding of how work worked for me.

I've had board members of companies say in the 1980s when I was coming up through the system, this one lunch that I had with the guy who turned out to be my mentor, made my career like, uh, dude, you were highly successful.

And that was the 1980s.

Right?

So let's think about this more broadly.

What's happening overall, about two thirds of firms still have a flexible work policy.

Like flex Index tracks literally 9,000 companies in the United States last year.

That didn't change much more people are moving towards like three days as being the right answer.

And for most people, if your team is co-located, meaning the three of us are on the same team and you live in the same city two or three days a week is fine.

And most people are accepting of that.

The challenges, a lot of organizations are now, the teams are distributed.

So you see this in like Microsoft's data, 75% of Microsoft teams, the manager and the people who work for the manager don't live in the same city saying, I have to be in the office three, four, or five days a week to be with my team.

Right.

It just doesn't make logical sense.

And it actually slows things down if you are across time zones, because then like, so you want me on the west coast to come into an office at 9:00 AM that means I lose an hour commuting that I could have been on a call with my East Coast counterparts.

Yeah.

So there's no right solution here, but a top down mandate generally doesn't work and neither does complete individual chaos.

It's finding that solution in the middle that works on the basis of things.

Like, is my team co-located or are we distributed?

We had a conversation, um, with another guest where we were talking a little bit about like return to experience Right.

Or in turn to intentionality.

Yeah.

So if there is going to be a reason for people to meet together in person, let's have a very clear agenda and That's right.

Take something away from it.

Are you seeing companies take that approach too?

Absolutely.

I've actually got about, uh, 15 companies that are actually in a, in a work sort of working groups with me that basically have gotten over the hump of like, how many days a week is a magic number and are thinking about how do we actually invest in learning and iteration to make it work?

So Zillow is a great example.

Zillow has a small central group of, I think four people that orchestrate gatherings across the, the entire organization.

The product engineering and marketing teams get together four times a year, and they do it for project kickoffs and mentorship and belonging and relationship building.

But most leaders aren't very good at, like, I've been in C-suite conversations where I've said, Hey, you guys have to actually get your people together and spend half the time on relationship building.

And I get these like panic looks of like, what would we do during that time?

So they also help people build an agenda, think about the activities, who are people you could bring in to do that?

That type of even poorly engagement, there's data that shows it actually is a better boost because it's purpose driven.

Right.

To your point, rather than the random chance encounter in the office.

Yeah.

I think people are more willing to invest the time if they know that there is an impact coming out of it.

That's right.

That's right.

And there's, there's patterns around those moments that matter.

And it depends very much on like how does your function or your team work, right?

So product design and product engineering coming together around projects makes sense.

Junior salespeople being together more frequently also probably makes sense, but those are very different patterns that you have to establish.

Yeah.

But if we're gonna come back to the office, sit in our cubicles, not talk to each other and do the same thing I could have done in my home office.

Absolutely.

And especially if I'm coming back to an office that looks like it did in 2019 Yeah.

Where I can't find enough meeting rooms.

Mm-hmm.

And by the way, I'm spending my day on calls and all I'm doing is hearing everybody else's calls.

That's why people basically bodily reject it.

Yeah.

'cause they aren't as productive.

Yeah.

Those o open office spaces, please go away forever.

Yeah.

And there's a lot of workplace people that I work with who've actually successfully made the case for shrink the footprint, but redesign what we're, what we're leaving behind and in verdict from being like 70% about individual space to 70% collaborative space.

And there's a lot of other workplace leaders who are still trying to convince leadership that, Hey, look, the economic trade off works.

We're not gonna spend any more money, but I need you to free up the opportunity for me to do this, which means I need you to get off the belief that we're all going back to what things look like in 2019.

It makes me also reconnect with the strategic plans that we're rolling out and adding the office as a tool to execute and achieve that strategic plan versus it being maybe more like phrased or approached in the outcome base.

Like we just need people to, the goal is just to get people here, and that's the outcome we're going for.

That's right.

Just to be in the office and, and how do we realign it to be more of an input towards achieving our goals as a company.

Right?

Yeah.

Technology is a tool.

Yeah.

Shared space is a tool, right?

Yeah.

It can be your office.

It can also be flexible space provider, because a lot of these firms have realized I don't have a big enough body of employees in the city to take a lease, so I should use a flexible, uh, work provider for the monthly gathering or the five people that need it every day.

So speaking of technology and tools that are, are coming into our, our workforce, into our employee experience, uh, obviously I think AI is a hot topic here at Transform this year.

Oh, yeah.

Uh, and outside of Transform Everywhere, and now we're at a point where agentic AI is making its way into our workforces.

Yeah.

What are you really excited about or seeing with this?

So huge amount of potential meaning, and then things that I think people are starting to get over the fact that this isn't just a productivity or an efficiency game.

Matter of fact, that's actually problematic in how it's positioned, but you've got the potential to do things like provide people with better coaching and mentoring tools, which actually can do things like close a gender gap that exists like 26%.

Um, fewer women get a coach or a mentor at work.

Right?

It's been persistent for decades now, and we're not fixing it by actually addressing the human causes, but you might be able to make it a little bit better by giving people access tools that will at least help them in the early stages of, and, uh, ways of working.

The, the bigger broader issue is like if, if flexible work, if the return to office thing doesn't work because of the top down command, top down command to use generative AI to get more efficient, also doesn't, you can see it, we're now like a year into the same stinking data.

About a third of employees have adopted these tools and are using 'em pretty regularly.

15 to 20% have adopted them and aren't telling you about it because they're afraid that they'll be seen as a cheat or that their job is at risk and the other half are sort of sitting on the sidelines.

Right.

But if you can't get people to, to understand like what the ultimate goal of the business is, what are the outcomes I'm trying to drive?

When they hear efficiency, they think layoffs.

Yeah.

It's the same problem as when I hear, get back in the office, even though I've been productive at home, what I hear is you just wanna monitor me.

Right.

Uh, in order to have me generate more, you know, visibility.

So the better answer on both of these is what are the outcomes we're trying to drive?

And it has forced a lot of companies to get crisper about that.

Like Synchrony Financial, outta Connecticut, FinTech firm that basically did away with the annual performance review, moved to a lot of other people are starting to move to, which is a quarterly goal setting and assessment process.

Every management, every employee, it's a heavy lift.

You have to invest behind it.

But if you can do that, you're starting to have more frequent interactions that are about what are the business results we're trying to create.

If you can do that, you also get away from presence as being the indicator of performance.

And you get away from fears about generative AI stealing my job.

Because you know that the objective is to generate more revenue, bring in more customers, build more product.

That's a mutual game, right?

It's better for the company, it's better for the individual, and it helps get rid of some of the fears that what you're actually after is pushing me out of the business.

Right.

How am an organization start to approach that conversation within their company, right?

Like, if we want to really embrace this technology, make it a part of our people's roles, and enable them to leverage it as a tool.

And I think it's interesting the stats that you shared, right?

Like whether we're pushing it or not, people are still using it.

So That's right.

How do we help them be intentional and more strategic effective with it?

Uh, we don't wanna cross the communication with, uh, creating this narrative.

Well, they're probably just making me do this to replace me at some point, right?

Yeah.

So we want it to be a people first productive strategy.

What, like how does the CEO or company approach that?

Like, what are some ways they could do that?

So, a big thing to do there is to think about that not as being a CEO's job and CHRO's job.

It's actually the individual leader's job.

And that's hard because we've often underinvested in our frontline leaders and managers.

But the, the, there's actually good evidence that's starting to show up about the fact that if you actually talk about this as a team, if your manager sits with you and experiments with these tools together, and don't make it about work at first, actually make it about, you know, what can we, how do we actually get you used to using some of these tools for things like build a recipe mm-hmm.

Or something.

You actually get people talking about it.

What you're actually then doing is you're creating a permission structure.

You're talking about norms.

What's acceptable use with N Teams.

A friend of mine, Helen Cup, runs a group called Women Defining ai.

They're trying to help close the gender gap in, in technology adoption.

They actually have started running these programs where people do five to 15 minutes snippets of hands-on activity every day for three weeks.

And it starts with the most basic things of prompting.

It works its way up to custom app building.

Right?

And if you do that as a team, you're not only learning, but you're actually having a conversation about what's okay for us, what's not okay for us?

And you're having the open discussion about what's our, what are our norms in it?

And you're getting people involved in it that requires investment of time, energy, and resources at the frontline level, not just a memo from, you know, the CIO that says, here's the new tool we've rolled out.

Right.

Um, you also talked about how these AI conversations, while still very relevant, have taken a little bit of a backseat to the world just being what it is today.

Yeah.

Um, how are you seeing CPOs CHROs lead the conversations within their organizations?

Um, I don't know if you're familiar with Edelman Trust Barometer?

Oh, yeah.

Oh yeah.

Yeah.

Came out workplace still.

Yeah.

But it's still one of the places that is most trusted Yeah.

By individuals.

Um, so they're looking to those leaders to guide them.

How are, how are they taking hold of that?

Yeah.

So being a a Chief People officer has been hard every year for the past five years.

And it got worse.

Again, this a lot of ways, and so a lot of the conversations I've had with people here today are how are we taking care of ourselves and our, and our own leadership teams?

So I'll give, I'll give you a really concrete example.

And that goes back to like that team building and engagement and trust.

You're probably cons familiar with the concept of first team.

Mm-hmm.

Like who's my first team, right.

And at the executive level, you've really gotta make sure that you are building trust within that executive team today, because the year ahead of us is going to be rough.

And if you don't have trust within that group, then things can fragment and fracture and fall apart.

So you'd need to do it with your, your leads and your directors within your people team, but you also need to do it across that.

And so that kind of comes back even to like the Zillow example I was giving you, but like getting that group together, because they probably live in different places at least a couple times a year, and spending time getting to know each other so that I know that I can trust you, Amy, so that I know something about you so that when something goes awry, I'm not gonna, you know, misinterpret something you said, but if I do, I'm gonna call you up and talk about that.

Right.

So there's just, we're in a time of high stress resilience is gonna be a really important thing to develop individually and in your teams, but if it doesn't have a foundation of trust among your leadership team, it's gonna be even harder.

Yeah.

I a hundred percent agree with that.

And how are you seeing it impact the individual employees too?

Because, you know, I think we all kind of originated and aren't working where you check personal at the door.

Right.

You walk in, you turn into the, you know, stone face.

Nothing bothers me.

Yeah.

Um, and that has evolved a lot, certainly since COVID.

I think that there was suddenly this opening that happened.

Yeah.

Um, and now it's with 24 7 access to information, it's pretty much impossible to check anything personal at, at the door to work.

So it is how are we helping employees stay a little bit focused, feel safe, feel that they're in a, an environment that is going to help them continue to grow and succeed.

Yeah.

It's really hard.

Um, like burnout hit new highs last year also.

It's not gonna get any better this year between the, like do more with less mantra.

We're like the third year of efficiency.

Um, so the, the pressures on people have been really high, folks now rightfully concerned about a recession or stagflation as of 24 hours ago.

And that's got people concerned about, you know, the economy, their personal lives and what's happening and layoffs and all the rest of it.

The war on DEI also impacts roughly speaking, half of the working population.

Yeah.

And that's hard.

I think the challenge as leaders is the bring your whole self to work, understandably, may have swung too far in one side of the pen.

Right.

I worked in tech for 25 years.

Tech tends to go from one pole to the other, to the other.

Tech went, you know, excessively pro employee, plenty of people who sort of took advantage of that system.

Now they've gone all the way to the other end, which is, um, sit down and do your work and your goes back on the grinds stand.

There's a medium in between that we need to fin, which is vulnerability with boundaries to, you know, take Brene Brown's, uh, term for it, which is how do you and I have a conversation that says it's okay for you to say, Hey, I'm having a hard time at home.

I'm gonna, it's gonna be a rough week.

Can somebody help me out on a couple of things?

I need you to be able to do that.

That doesn't mean that I'm your therapist.

Mm-hmm.

And that I'm here to help you solve that set of problems.

But if you, if you don't, if you don't help people figure out how to have those conversations, then people will hit that burnout break point.

And I think this year we're at risk of pushing that over the cliff.

And so that's, that trust issue again, is gonna come really into the forefront, I think, for a lot of people.

Yeah.

I agree.

So we're obviously at transform.

Yeah.

The ethos of transform is very much on the transformation of work.

The big disruptors changes in both people's strategy, but also even technology and people tech.

Yeah.

Uh, yeah.

I'm curious of like any bold predictions, thoughts, strategies that you feel organizations should be on top of or aware of to stay ahead of the curve.

Like what are, what's your bold prediction or thought We're, we're seeing this big, uh, search back to command and control, right.

There's a big push back to command and control and whether it's return to the office or do more with less or all the rest of it, I think that's gonna backfire on a number of large firms.

And it's not necessarily gonna backfire because some of their people won't do it.

But I think the, there's such a huge opportunity for the innovator's dilemma that's coming out of all this, right?

That mid-size and smaller, more nimble organizations can do a lot more with generative AI to go a lot further, a lot faster.

I see this in my own industry that I've been in for years in SaaS, right?

The newer innovators can actually build more capability and functionality.

And if you are a 70,000 person, 150,000 person organization, it's just harder for you to make those changes and adapt.

If your answer to that is, I'm gonna command you into adapting it, you're not gonna get as far as these guys are who are gonna sit there and say, Hey, look, here's the outcomes we want to drive.

Here's the rewards you get and will allow you some freedom and flexibility to get there.

And that kind of engagement, I think will win long term.

Yeah.

So it, it is gonna be hard to prove, but I think the command and control thing is gonna push some people into underperforming.

Yeah.

And I think it's gonna increase the odds that they get increasingly displaced over the next five years by an even faster generation of new capabilities and technology to come up, uh, from underneath them.

Yeah.

And that's a pretty exciting future for those companies that embrace that more.

I it sounds more playful, right?

It's like more playful experiential, agile, like agile approach to saying, Hey, I'm, I'm a high level of talent, I want to experiment and I want to achieve outcomes too.

Right?

Like, people are energized by that.

That's right.

But let me have a more, uh, a playful, flexible approach to how I do that.

Yeah.

Like, that sounds really exciting for me.

Yeah.

I mean, I, I was a startup CEO for a dozen years, and what I learned over the course of that was in often food school of hard knocks is this whole culture and strategy for breakfast thing is absolutely true.

Mm-hmm.

You'll, I was at another event recently where somebody asked a group of senior leaders like, would you take the C strategy with the A team?

Or would you take the A strategy with the C team?

Right.

And the A versus the C on the team isn't necessarily the talent, it's can you actually get them aligned?

Yeah.

Can you get them actually focused on the job and on what you're trying to build and, and, and understanding each other and their strengths and weaknesses.

And that's what I learned, right.

That if you can do that, then you don't have to have the world's greatest strategy, but you're still gonna outperform somebody who's like telling everybody to get into the same square boxes.

Yeah.

Well, that's exciting.

I'm, uh, I hope so.

I feel, I feel, yeah, I feel very, uh, energized by that vision for, for those companies that embrace that type of, I guess, mindset or philosophy on how to run a team and an organization.

And, uh, uh, so yeah, I appreciate you sharing that with us.

Appreciate you coming and sharing your perspective and, and your thoughts with our network.

And this is, uh, this has been a wonderful conversation.

Thanks.

Thanks so much.

Thanks.

Appreciate it.

Good meeting you.

Thank you.

Thanks.

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