7: Leading From Home

In which we discuss the challenges of relationship management when leading from home, and then start a potentially promising discussion on the subject of trust.

Keywords: #OaklandSlowStreets, symbolic analysts, listservs, working from home, intent, distributed teams, serendipity, thresholds, conscious incompetence, improvisation, vision, galvanizing, trust, trust, trust.


Peter: Welcome to “Finding Our Way,” the podcast where Peter and Jesse welcome you to their journey as they navigate the opportunities and challenges of design and design leadership. I’m Peter Merholz and with me is Jesse James Garrett.

Jesse: Hello, Peter.

Peter: Hi Jesse.

We’re about in our first full week of #OaklandSlowStreets, and that one act that the city has done has measurably increased my mood positively. The major street that is nearest to us, which is this pass through street for a lot of cars because of freeway access, is now a slow street. And it is, throughout the day, overtaken by bicyclists and pedestrians.

And it is like a little town square and it is awesome and it just makes me very happy and I just walk up and down it. And I want this to always be there. There are things that we are learning about our neighborhoods and communities in what is otherwise a dark time. I get nervous glowing about some of these things ‘cause I know for a lot of folks that there is almost no upside but there are things we are developing in our communities that I hope we are able to learn from and maintain.

Jesse: I agree with you. I think that, despite all of the darkness, despite the, really the, the scale of senseless tragedy unfolding in slow motion all around us, yeah, it is forcing all of us to take a step back from all of the routines and all of the assumptions and all of the scripts by which we have organized our lives and the systems around us.

And Oakland Slow Streets is really interesting because it’s an example of the kind of thing we talk about in design all the time, which is, the emotional or psychological effects of system choices on the people who move through those systems. And, we have gotten to a certain level of baseline tolerance of a lot of systems that maybe when those systems come back online, we’re not going to be so tolerant of anymore and we’re going to start asking for different things. And that, I think, is going to potentially create a lot of exciting system-level design opportunities across a wide range of different fields and disciplines and areas of enterprise.

Peter: Well, yeah, for all of us symbolic analysts who find ourselves working from home when we would otherwise be in offices, it is unclear why anyone who is a symbolic analyst would be expected to go into an office again, at least every day. The amount of money companies spend on housing people in commercial real estate, that they could probably spend half of that, and just literally hand employees money and say, kit out your house how you see fit. And people could buy nice cameras and secondary displays and standing desks with treadmills or whatever they want. And it would still be far cheaper than housing them with commercial real estate. And that’s one of those where I don’t see how we go back to those assumptions.

And it’s funny because in design, so I’m on all these design leadership mailing lists, or community slacks. No one’s on a mailing list anymore. Sorry, I’m showing my age. I’m on listservs. I’m on all these leadership listservs,

Jesse: ”design leadership-l”

Peter: Hyphen L, of course. You know, that one. And, I’m on all these design leadership community slacks where people are still hiring and people are interviewing and one of them has a channel called a job-search-vent.

And right now, the biggest job search vent is how these companies are still expecting folks to live in a particular area, to go to an office every day when we come back from this experience, even though we know folks, at least with the kind of work we’re doing, are doing actually pretty well without going to an office.

Jesse: One factor behind the historical insistence on physical colocation is in part because what it would have taken to make that change would have been so disruptive to any organization that attempted it that what would happen would be it would get a bunch of people fired before it actually killed the organization. In this case, the disruption has already happened. So the question is simply, Where do we go from here?

Peter: Right, right.

Jesse: And I think in a lot of cases, the cultures and the processes of these organizations were so embedded in that physical context that the flexibility to evolve toward the digital and virtual wasn’t there.

But having cut all of those processes off rather abruptly, there’s now the opportunity to create something new in their place.

Peter: I use the phrase symbolic analysts, and I’m being both, silly, but, particular ‘cause a symbolic — 

Jesse: What we used to call knowledge workers,

Peter: –workers well and knowledge workers were symbolic analysts. I remember it was like the mid nineties that was the generic term for the kind of work we do. All now the people working on computers doing this type of stuff.

And often before this pandemic, there were folks who still worked remotely or would promote their perspective that we should do much more to enable distributed work.

And this was my experience when I was leading design at Groupon, I would drive an hour to an hour and a half to Palo Alto to not sit at a desk. I had a desk there, but I wouldn’t sit at the desk. I would go from conference room to conference room to sit on a video call with people in Chicago, Seattle, the cities that we operated, and my entire day from nine to five would be moving from conference room to conference room to be part of conversations where a significant portion of the folks we’re not in the room with me. 

Jesse: Right. 

Peter: And so work had already gotten to this distributed notion. People–

Jesse: And I’ve seen many organizations that work exactly that same.

Peter: Yeah. If you, if you look at even people at their desks, they’re often staring at a screen on a call with other people. We were operating in this distributed fashion. We just sat near one another. I’ve come to believe that the reason we were still using offices is because we’d stopped being intentional about that. That was not an intentional decision. In the same way that we work in these bureaucratic hierarchies because it’s how we always have, we worked in offices because that’s how we always have, and we do a bunch of things because it’s how it’s always been done.

And now we have a break point. My concern is that too many people will try to return things to the way they were, as if that was better, or superior or natural, instead of really taking stock and taking advantage of how we can operate in new ways that are better suited to our current reality.

Jesse: I completely agree with you. And, as this has gone on, I’ve heard that sentiment from more and more people that people are, in their own lives, taking stock and reassessing how they’ve structured their lives and the priorities that have been, to your point, unintentionally, or at least unconsciously, built into those choices.

And I can see organizations doing the same thing for sure.

Peter: I’m working for a 150 year bank right now, and they’re all having to work from home.

And it has been clearly a painful transition for them from an infrastructure standpoint. But I have to imagine that they now are realizing that there are new and potentially better ways of working that they will need to adopt. 

Jesse: I want to come back to the cultural issue, around presence in the office because I think this is one that has a particular meaning for leaders in organizations, in that presence in the office for leaders often is about maintaining a certain level of visibility, especially visibility among people that you don’t directly interact with.

Maintaining a degree of visibility with your weak ties, with those peers whom you may not be collaborating with day in, day out, but who you see once a month, once a quarter, and who you need to maintain relationships with.

Peter: The most obvious casualty of distributed work is serendipity, is the hallway conversation, is running into someone in the break room. And leaders more than other folks within an organization benefit from that, given the nature of their roles.

Something we’ve talked about in earlier episodes is how the medium of leadership is relationship. Those relationships are built both through scheduled and intentional interaction, but also through passive serendipitous interaction. And we’re now carving out a significant chunk of that, when you’re looking at things in a purely distributed fashion. That said, in my experience… So my last full time role, at Snagajob, I was part of an office of 30 people in Oakland, and the other 470 people in the company worked in Virginia and South Carolina. And I still felt I had a decent leadership relationship. You know, part of that was, five days a month, I traveled to the largest office and like literally just kind of hang around, sit around, see…

Jesse: That’s what I’m talking about though. Like that hanging around has value…

Peter: And I made serendipity happen just through my presence. And I would let people know when I was there, “I’ve cleared my calendar, don’t need an agenda, just here to hang out.” But, being distributed doesn’t mean being physically isolated. And that’s where intent becomes important, right? There’s opportunities to pull people together. So as a leader, you can say, “Hey, let’s get everyone together in your org, to meet, and in those company-wide gatherings, you reintroduce those opportunities for serendipity and for unintended connection.

Music break

Peter: The companies I know that have distributed teams, offhand, the design isn’t great. What ends up happening, I think is, it is harder to build a design culture. And in those distributed workforces, the work gets highly atomized. You get a lot of little product teams doing a lot of stuff. And so the overall quality of design throughout an organization is, on average, lower than I’d like. There might be spikes where certain teams are doing it well, because there’s a good design leader, good designers in that area. But it’s not something that you can generally, across the board bring up. 

Jesse: Well, the distributed context places so much emphasis on the communication skills of the team and the ability to clearly get an intent across to a collaborator and be able to receive and incorporate and integrate whatever feedback you get from that.

And to be able to handle those volleys of ideas within a team more smoothly. In a physical context that often is a matter of interpersonal attunement, right? So you’ve got a group of designers around the table that are all working together on a problem and everybody is sort of tracking everybody else in these really subtle ways in terms of, “Is everybody on board with this idea? Is there somebody who’s like, maybe resisting it a bit? You get all of this stuff from body language and all of these micro cues that are more available to us in a physical environment that I think leaders are struggling with right now, especially if you’re the kind of leader who makes decisions from a place of synthesizing and integrating these signals of attunement and alignment from your team to be able to say, okay, this feels like the direction that is going to best address the problem as I understand it from the perspectives of all the people in this room right now. When they lose access to that rich real time information source about their collaborators, it becomes a lot harder, and it’s a lot harder to do that over a video conferencing app like Zoom, and it’s even harder to do that when everybody’s attention is focused on something like a virtual whiteboard, and you may only be hearing voices in your head and seeing little pointers flying around on a screen.

Peter: The voices. The voices.

Jesse: Yes.

Peter: In my last role, there was a problem that ended up being localized to the Oakland office. and we addressed it because we were all there and I could be pulled into a conference room in a moment’s notice and say, “Hey, this and that and the other thing isn’t working. There’s some sensitivities. There’s some, personality clashes,” et cetera, et cetera.

And you could do five minutes here and five minutes there and you can kind of feel your way through addressing this problem in the moment.

Whereas problems that arise among a distributed team, because you need to be so much more intentional and much more explicit in your communications, well, now you need to grab time on someone’s calendar, and when you talk to them, you need to like have your case made about here’s the nature of this problem.

And now as the leader, in order to resolve the problem, you can’t just pull people aside. You now have to set up a series of meetings yourself and it just turns everything that could have been handled in a humanistic rhythm….

Jesse: Yeah, and in a graceful and informal and humane way, rather than turning it all into these formalized artificial structures that feels like you’re being sort of fed into this big machine instead of just having a conversation with the person.

Peter: And so my concern is that there is going to remain a set of lower-lying problems that don’t hit that threshold, that you as a leader might not even realize are happening, right? That just don’t break through the surface. And then once it does hit this threshold, it becomes this thing that now has to be projectized.

Jesse: Yeah. Triggers a whole bunch of sort of formal processes around it that may be totally ill-suited to the nature of the problem at hand. I completely agree with you and I think that this environment makes it particularly important for leaders to be continually pushing down that threshold of how big a thing needs to be in order for their people to come talk to them about it, and for them to be able to feel like they can casually shoot you a DM in Slack and feel like that’s not going to spin up into something that’s completely out of scale with the scale of the problem itself.

Peter: Yeah. It might not align appropriately given the nature of the challenge that you’re trying to address.

Jesse: I think also for design leaders, this technology introduces new challenges, as remote facilitators of processes and as orchestrators of conversations. And running people through exercises and taking them through the process of generation and synthesis and driving decision making, doing all of those things, in the context of virtual environments is another skillset that most of us are still learning. And, as the tools evolve, we’re going to have to evolve to keep up with them.

Peter: Definitely. One of the skills that help designers facilitate those types of conversations is a certain empathetic quality, but also a certain ability to improvise. And one of the challenges, is you still need to improvise.

You need to be able to realize in a context of a conversation like, “Oh, we should go in this direction. And I have to put aside the plan that I had and pursue it.” 

Running these types of workshops virtually, I find requires me to be way more prepared ahead of time, and understanding what the activities are going to be, how they’re going to proceed. And the challenge is you have to be both more explicit upfront in terms of how you structure the sessions, but you still, you don’t want to be rigid and you still need to have that ability to flex, and that, that’s just harder. I think it’s just harder.

Jesse: Yeah, it is harder. And part of it I think, again, comes back to how closely are you able to stay in tune with the other people that you are collaborating with? And how, are you able to track their reactions moment to moment to the evolution of the ideas? And, that improvisation is such an important skill.

Peter: Design leaders are kind of being thrusted back almost into conscious incompetence like they’re having to start over their practices and what works and the things that they had internalized that they could kind of rely on. They’re now having to call into question, much as we said at the very outset like how businesses are having to call into question some fundamental aspects of how they operate. And it would be interesting to consider what are those aspects of leadership practice had become unconscious or subconscious that are now needing to be made explicit again. And I think one of them is this ability to improv. It’s this ability to flow. It’s this ability to react and realize something that has bubbled up, an issue has developed or an opportunity has arisen, and now you’re going to lean forward and tackle that.

Jesse: You got me thinking again about this great reset that is happening at all scales. It’s happening at the scale of the individual as individuals are reassessing how they relate to their lives and the world and purpose and meaning and all those kinds of things, that’s happening at the scale of small groups of people, whether those are families or teams or whatever and the whole reconsideration of how those interaction patterns work. And then it’s happening at the larger scale of larger organizations and eventually institutions and governments and whole societies. So, I think that what you’re talking about is one expression of a larger reconsideration of everything that is happening. I think that this may be an area where a newer leader has certain advantages in that they haven’t yet had the opportunity to build up a lot of habits and practices that are rooted in the pre-distributed context.

Music break 2

Peter: So I’m thinking about this in the context of a particular initiative that I ended up being responsible for when I was at Groupon, about six months into my time there, I was told by my boss, the SVP of Product, that in six weeks time he was expecting me to present at the company all hands to all 12,000 employees a vision for the future Groupon shopping experience. It’s one of those things, it wasn’t out of the blue. It had been bubbling, but it was like, now is the time. Because he was looking at the whole calendar of 2013. We show a vision in April, and then by October of that year, five months later, we start launching the first steps towards realizing that vision. And we wanted to get those first steps out before the holiday break. as eommerce, ecommerce is very seasonally minded. And we did a code freeze, basically, right before Thanksgiving.

And so, he had done a lot of work to develop a product strategy. And so it’s like, we know the product strategy. Make that go. And he was looking to me to lead that. I, in turn, thankfully had hired an extremely capable design director, who’s now the head of design at Doordash, Helena Seo, I leaned on her and I’m like, I’m still running a design organization, so I can’t spend all of my time doing it.

I think I was able to devote about a quarter of my time over those six weeks to this, but I tasked her and she in turn had one or two other designers supporting her, and it was kind of their 50% plus job building this vision, and the vision was simply going to be essentially a series of comps that told a story of a future experience.

Part of why we were able to succeed is after that conversation with my boss, I could go over to her desk and say, “Hey, I need to talk to you about a thing.”

We could start that planning. She could go to two people who worked near her and she could say, “Hey, we’re going to be doing this together.” And the bulk of the effort took place between the four of us, co-located working every day, moving this thing forward. 

Now I’m coaching, this design leader who wants to prepare a similar vision, his ability to pull together a skunkworks, a strike team to do that is just way compromised because now all of this stuff, again, has to hit that threshold of “It’s a project” and, it was a project for us, but we were still able to be kind of off the books and scrappy about it.

Jesse: It’s hard to feel scrappy when you’ve got an official Jira board. Right.

Peter: Yeah. And, as I’m thinking about what this leader is going to try to do, it’s just not going to be as flow-y as I had it when I was in a similar situation six or seven years ago, and I could just pull together this little strike team to make it happen.

Jesse: Yeah, I agree with that. It seems like for design leaders it’s going to be really key to find ways to create those opportunities for serendipity, opportunities for serendipitous interaction, whether with their peers or amongst the members of their teams. And also to try to find ways to culturally encourage and technologically enable more kind of looser ad hoc conversations, you know? There was a time not too long ago when people would just pick up the phone and call you without having scheduled anything to have a three minute conversation about something and then hanging up the phone when they’re done. And this was a common way that a lot of human interaction happened in the 20th century in business. And we managed to have those ad hoc conversations in these relatively informal ways, still using distributed technological tools.

Peter: Slack is not a means for galvanizing, I don’t think.. That, that doesn’t mean…

Jesse: …Tell me what you mean by galvanizing in this way…?

Peter: Galvanizing, right? How do, how do I get two, three, four people together and light a spark and make work happen and seed…

Jesse: You’re talking about activating groups of people as opposed to individuals.

Peter: Yeah. Slack is great once those groups have been identified and you need to give them a tool to enable their ability to work together. But to spin up, I don’t know, maybe I’m wrong, maybe people are doing this on Slack, but, to me, that feels very much like a face-to-face, that could be distributed-face-to-face, but face-to-face set of interactions or, or at least voice-to-voice interactions.


Jesse: It sounds to me like what you’re yearning for is a way to gauge and help create buy-in for people that you want to get motivated, get excited, get engaged, pour their energy into what you’re putting forward. And what I hear you saying is that that’s a lot more difficult to do in a text chat environment as opposed to face to face or even a phone call.

Peter: I suspect so. A few episodes ago, we talked about leadership rarely has authority. Leadership is about influence. Management is about authority. And so the manager approach to activating and galvanizing is, “John. Mary. Joseph, you are now working on this thing, go!” and they’re like, “Okay, it’s my job. This is what I do.” You’re not going to get the best work out of John, Mary and Joseph in that context. You know, we know that people work best when they feel that connection to purpose. That’s why we spent so much time talking about purpose.

We know that people work best when they feel like there is a higher order mission, and opportunity that they are realizing. People work best when they feel self-directed, when it doesn’t feel like someone has told them what to do, but someone has said, “Hey, here’s this really amazing opportunity to make significant change.” And that person now is like, “I’m in because I want to be part of an amazing opportunity.” And that’s what I mean by galvanizing. That type of galvanizing is done through, I mean, you’re now starting to speak to their emotions. You’re trying to speak to their higher selves.

And I think, you know, an all-caps shout out on Slack doesn’t spur that kind of followership that’s that passionate, engaged, “I’m in” quality that face-to-face does.

Jesse: I think that trust is an element in this too, that the real-time, face-to-face interaction provides for the opportunity to build some trust in the relationship. That is, again, not impossible to do through other channels, but just harder because we have less access to the physiological cues of emotional states that help us stay attuned to one another from moment to moment.

And in the absence of that, it can be hard for team members to really fully buy into a leader’s vision at a deep emotional level because the leader doesn’t have the ability to calibrate the communication of that vision to the emotional responses that the leader is getting to in that improvisational fashion.

So the ability to have an improvisational conversation with somebody where you are responding moment to moment, to their emotional reactions, to what you’re saying, is how you build that baseline of trust that is going to allow both the team member and the leader going forward to trust in each other’s intentions.

For the team member to feel like the leader has a vision that they can invest in, that they can believe in and for the leader to feel like the team members get it enough that they can turn their back and trust that that thing is going to go where they wanted it to go.

Peter: All I have to say to that is, is yes to all that. 

One of the things that we don’t do enough within organizations is earn our team members’ trust, earn our employees’ trust. Oftentimes we approach things from a stance of assuming trust, that if I am engaging with you, I assume you trust me. And in fact, trust has to be earned. It has to be earned over time, particularly when you’re dealing with these types of sensitive emotional aspects of meaning, of purpose, of connection, of engagement, you can’t assume trust. If you start by assuming trust, you’re not going to get anywhere almost from the outset. And it’s funny cause trust has to be two ways, right? The individual needs to trust the organization, that the organization is living up to that purpose that it is talking about. And that their effort is connected to that higher purpose. It’s one thing when a company is selling these humanistic values of community and neighborhoodliness and all that. And then you find out that they treat their workers terribly. If anyone’s trust is to be assumed, it is the employee’s trust. Whereas the company tends to think their trust is the one to be assumed and that employees…

Jesse: Right… 

Peter: … have to earn the company’s trust, right. Through their performance and through their effort. And I would argue it’s exactly the opposite… 

Jesse: …Showing up at the office…

Peter: Yeah. And I would argue it’s the opposite, that companies need to earn team members’ trust because so often team members have been taken advantage of by the companies that they work for.

Organizations, companies, individuals, leaders don’t pay nearly enough attention to trust that they should. Even more than purpose and meaning, and some of these other things, trust is as, if not more, important and far less well understood.

It’s almost never made explicit. It’s almost like we’re wary of bringing trust into the work environment because, my guess is, because we think we fear we will have to break it. At some point, we are going to have to make a decision that breaks that trust. And so we almost don’t want to start that conversation for fear of where it will go. But in order for us to make the….

Jesse: Wow. That’s just, well, I want to, I want to allow some space for that. Cause that’s a pretty powerful statement, what you just said. And, the notion that leaders are carrying around with them, this burden all the time of the knowledge that whatever trust they build, they might at some point have to destroy as part of doing their job it’s a challenging place to be.

It’s interesting that we came to this place just because, trust actually was a big component of the work that I was doing in the last couple of years at Capital One. And, it’s an area that I’ve been digging into and trying to figure out how to bring greater understanding of to my practice with leaders. So I have a lot of things to say about it.

Peter: Well, maybe that becomes the subject for our next conversation… 

With this strange fractured conversation that I think reflects a certain reality of our world today. Trying to keep on top of a bunch of different threads in new ways, in new contexts. That wraps up another episode of “Finding Our Way.” We thank you for taking the time to listen to what we have to say. We look forward to your thoughts and input. We are happy to announce that as of this recording, we actually have a website, https://findingourway.design/ Probably the best way of getting a hold of us. There’s a contact form there. It’s also where you can find all past episodes and, links to podcatchers and all that kind of good stuff, how to subscribe. So, find us there, send it to your friends.

And, we look forward to having you join us on our journey as we continue finding our way.

Jesse: Finding our way. Thanks Peter.

Peter: The sound is so much warmer now. Can’t you tell?

Jesse: Yeah. It’s like you’re right inside my head.

Peter: Either that or it’s because I’m using my FM DJ voice?

Jesse: You seem to be in good spirits today. They are all computers now. I think, actually that’s not true. I know someone who was an FM DJ, so…

Peter: But, but at this point, Alexa could basically run radio across the country and most people wouldn’t care.

Jesse: No. Most people wouldn’t notice. Yeah.

Peter: I guess I’m in good spirits. I find that my spirits track with the quality of sleep. I had a good sleep, so I’m in good spirits.

Jesse: Mm. Excellent. Well, that’s good.

Peter: Yeah. I’m pretty simple.

Jesse: Yeah. Well, you know, on some level we all are. Right.

 Peter: if we had known where we were going with this conversation, we could have invited that design leader focused on distributed teams and… 

Jesse: if we had known where we were going for this conversation, we never would have gotten here.

Peter: And maybe that’s for next time.

2 thoughts on “7: Leading From Home

  1. Your thread on Trust at the end is a great segue towards your next journey. I’m seeing Trust and Safety being one of the new(er) and more rapidly growing teams at technology companies.

    Technology is wonderful at masking the flaws and reality behind the processes that magically make content or objects appear on our screen or on our doorstep. Emphasizing trust also reveals humanist vulnerabilities. Over the last few weeks and months, we’re seeing the differences in the level of perceived trust between say, Twitter versus Facebook. I trust that the content on this platform is either representing my ability to speak freely, or representing my ability to know the truth. Take your pick.

    I would love to hear more on your discussions of trust in terms of employees and their corporations as well. Design and their “seat at the table”, and trusting that you’re being heard.


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