Navigating Uncertainty: Adapting to Rapid, Inclusive Change in The Workplace

Jennifer Brown | | , ,

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Aaron Dignan, founder of The Ready and co-founder of, shares his own diversity story and why he always felt different growing up. Aaron discusses how companies can move away from command-and-control bureaucracy towards new forms of self-organization, dynamic teaming, and empowerment. He also gives examples from his own company about the practices that he uses to create trust among diverse teams, as well as an overall culture of inclusivity.

In this episode you’ll discover:

  • Aaron’s diversity story and why he felt different growing up
  • A new model of organizational structure that is more responsive
  • What successful companies have in common
  • How to build trust in diverse teams
  • Why men often struggle with a more responsive organizational model
  • How allies can be most supportive in the workplace
  • How to speak openly in a diverse team with offending others
  • A communication channel that Aaron uses in his own business
  • How to focus on what matters most when it comes to diversity and inclusion
  • What’s missing from most organizational structures
  • A major problem with mentoring and what to do about it
  • How to create a culture of inclusivity
  • How to access additional resources for creating a responsive organizational culture


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Listen in now, or read on for the transcript of our conversation:

JENNIFER BROWN: Welcome to The Will to Change. This is Jennifer Brown. My guest today is Aaron Dignan.

In 2007, obsessed with the way exponential technologies were growing and shaping our daily lives, Aaron co-founded the internationally recognized digital strategy firm Undercurrent. Based in New York City, the firm served the Fortune 500 for over eight years.

His latest venture is The Ready, an organization design and coaching practice based in New York City. The firm focuses on helping companies large and small move away from command-and-control bureaucracy towards new forms of self-organization, dynamic teaming, and empowerment.

Dignan is an active angel investor, and helps build partnerships between the startups and “end-ups” he advises. He sits/sat on advisory boards for GE, American Express, PepsiCo, and Cooper Hewitt, as well as the board of directors for Smashburger. He is the author of Game Frame: Using Games as a Strategy for Success, (Free Press, 2011) and an upcoming book on organization design.

Aaron, welcome to The Will to Change.

AARON DIGNAN: Thanks for having me. I’m excited.

JENNIFER BROWN: Yes, me too. Let’s start as we always do on The Will to Change. Our theory is everybody has a diversity story. I’ve heard you talk plenty of times, and I am confident that diversity, inclusion, exclusion, all of those things have played a role in your journey in various ways. I’d love to have our listeners hear where you came from, and more generally, what was remarkable about your early years that holds the ingredients to the kind of leader you are and the work you do now?

AARON DIGNAN: Sure. Sure. It’s funny because I think I have an origin story that is both extremely homogenous and extremely about difference.

I grew up primarily in Colorado among a gaggle of homogenous, white, upper-middle-class kids. I did not experience a lot of diversity or difference, as we would now talk about it, in my formative years.

I didn’t experience the lack of it in the sense that there wasn’t outright racism or sexism or anything like that present either, but it was a washed kind of bubble. And that left a space in me that I didn’t know was there in terms of exposure and experience.

At the same time, I was very different myself. I thought very differently, I was interested in different things. I never went to parties, I never went out for sports, I never participated in the way that normal people did. In fact, it’s somewhat known about me that I went to first grade dressed as Batman for about 180 days. (Laughter.) And people just thought, “Something is wrong with this kid, he’s different.” I was ostracized, in a way, for being a different sort of thinker and a dreamer to a certain extent. I felt that. I felt being part of the “out” group, but I built my identity around that, around thinking differently and being an iconoclast. That has stuck with me.

Meanwhile, when I did finally move out of there and come to New York and start to experience a more diverse environment, it was so new and novel that I jumped in with both feet and have been making sense of it as best I could ever since, and trying to be comfortable in places where I’m uncomfortable.

JENNIFER BROWN: I love that. We share that. I grew up in a really homogenous place as well. Definitely felt that something else was going on.


JENNIFER BROWN: New York saved my bacon too. (Laughter.)


JENNIFER BROWN: Right? Just coming here and feeling, “Wow, I can breathe and explore and I’m not going to stick out.” But at the same time, I’m going to be able to meet anyone I want to meet and be stimulated in the ways that we’ve always been curious about in our various small-town communities that we grew up in. I know, it’s a life-saver.

AARON DIGNAN: It really is. It really is.

JENNIFER BROWN: I have been intrigued in watching how you explain culture in the workplace. I thought we could just get right into it. You’re a specialist. You deploy teams, just like we do at my company, to create organizational change, to partner with our clients on creating that, to overcome all that lovely resistance that we face in doing that, and wanting change to be rapid, inclusive, and participatory.

I talk a lot about being seen and heard and needing the voices in every organization or entity to be heard.

You talked about actually having those voices also be participating and inputting. You have your favorite org chart you show where you show the class, “What year is this org chart from?” We all guess 1980, 1990, 2002. And you say, “1920, and it looks exactly the same as our companies’ org charts today.”


JENNIFER BROWN: It’s true. We’re working in these outmoded structures that aren’t good for feeling seen and heard, or facilitating the participation and the input that’s so critical.

First of all, dive into that a little, define it for our audience, and then tell us what you observe about why cultures are so slow to change.

AARON DIGNAN: Yes. I think at the highest level, the systems that we’re in still reflect the systems that we came from. We have this inherited way of working, this inherited way of organizing that the org chart nicely summarizes. It’s very hierarchical, very top-down, the control and the decisioning is happening in one place – at the top.

That was fine, I guess, maybe not from a humanist perspective, but it was fine from an operational and strategic perspective in a time when there were relatively low dynamics. But now we work in this world where there’s high uncertainty, high volatility, lots of change, and you don’t have to pick up a newspaper to even sense that.

In many ways, we’re trying to navigate uncertainty, which in my view is like anything else. Whether you’re piloting a boat or walking around in a room that’s poorly lit, navigating uncertainty means sensing. And sensing requires sensors. At some level, the organization now needs to become rich with sensing and rich with sense-making. That requires participation.

We get very quickly to this place of, wow, we need everyone in the organization to participate, and the more different the participation is, the more divergent the thinking, the more cognitive diversity we have, the more accurate and powerful that sense-making will be. That would lead to a kind of group cognition and learning at the system level. That’s how you get businesses, organizations, nonprofits, and governments that learn and adapt to change rapidly and successfully.

It’s almost a prerequisite, in a way. I love when things that are right from a humanist perspective are also right from a systems perspective because you win on both sides. I think this is one of those cases where it’s just nice to be in an environment that’s inclusive, diverse, warm, welcoming, and holds space for everyone, but it’s also just better from a pure business, operational, goal-setting, or purpose-driven standpoint. It’s just better.


AARON DIGNAN: I think that’s the context. In terms of what we see, the biggest thing I’ve noticed is that there are habits and deep grooves in the record that’s spinning about how we show up, how we work, and the norms that surround us. Just like any habit, they’re hard to change because we’re not even really aware of them. There is a lot of just building awareness and just noticing bias and noticing participation that has to go on before you can even change it.

Frankly, there are a lot of different ways to perceive what’s happening. There’s a lot of power that’s threatened. There’s a lot of ego that’s challenged. And so you get a lot of muscle memory and a lot of antibodies that fight that awareness as soon as it starts to crop up. So you’re managing this battle on a couple fronts.

JENNIFER BROWN: I couldn’t agree more. You’re describing every moment of —

AARON DIGNAN: –your life, right?

JENNIFER BROWN: (Laughter.) Pretty much. It keeps me intellectually challenged and challenged on a heart level because there is such an emotional undercurrent. Sometimes it’s in your face, it’s not just an undercurrent.

AARON DIGNAN: Correct. Yes.

JENNIFER BROWN: Resistance, patterning, habits, and protection of power. Unwittingly, by the same people who will tell you, “I believe in equality. I believe in diversity.” Yet, the behaviors show something different, especially when somebody like me is not in the room. Right?

AARON DIGNAN: Yes. There are triggers. I mean, I believe in diet and exercise, but I still want a doughnut. There is going to be a lot of that. (Laughter.)


You have something called the “OS Canvas” that you developed. You looked at some of the companies that are known for speed, resilience, purpose, participation, and how they operate differently. Could you mention what those are? Perhaps you could highlight a couple that have particular relevance to the conversation about diversity and inclusion as you go.

AARON DIGNAN: Yes. We basically just went out and spoke to or looked at the case history for dozens and dozens and dozens of companies known for these positive traits and just asked, “What’s different about you?”

As we heard answers that ranged from the way they meet to the way they decide to the way they develop people to the way they talk to each other, et cetera, we just pinned them to the wall and grouped them. They became these clusters, and nine clusters arrived. Then we put the most generic name we could at the top of each cluster that would hold all the different behaviors in that space.

An example was “authority and decisions.” You could have a system that’s highly hierarchical and command and control and that’s how they approach authority and decisions, or one that’s very much about cult of personality, et cetera. Or you can have a system that’s highly distributed and totally free and fluid in the way it makes decisions. You could have one that’s more based on data or less based on data. Each bucket became a generic holding place for the spaces we think the future of work is being unfolded in.

The nine were as follows: Structure in space, basically how teams are formed and how you inhabit the physical environment. Authority and decisions, which we just discussed. Information and communication, which I think is a huge one for what we’re talking about because it’s so much about how information is transmitted, who gets to transmit it, and what participation looks like from an info standpoint.

Policy and governance, so how do we think about setting rules and norms, and how do we steer the organization towards its purpose? Purpose and values, which is right in the center and I think also connects at a values level, and to some extent at a purpose level, if your purpose is societal or communal in nature to these ideas that we’re talking about today.

Meetings, rhythm, and coordination, which is how we meet, how we align, how we keep multiple teams all moving in a somewhat similar direction. Again, very important for how people show up, how they’re received, how they inhabit those moments and participate or don’t, steer or don’t, show up as a whole person or wearing a mask, et cetera.

And then strategy and innovation, which needs no explanation. Resource allocation, targets, and forecasts, which is really all about how we move money and people around and how we think about what we are striving for from a budget and a goal-setting standpoint.

And then, finally, the last one, which really could be a canvas all on its own, which is people development and motivation. How do we think about people as human beings, how they’re developed, how they develop themselves, how they’re motivated in a system, how they’re paid, how they’re incentivized, how feedback works? All those sorts of bells and whistles, which I think are intimately connected to the conversation we’re having.

I think you see it show up in all of them, but certainly some more than others. And as we’re working, we’re just trying to help cultures navigate. What are the tensions you hold with the way you work in an organization today, the way you feel in the system today across these dimensions? And how could these work differently? If you don’t like the way you do strategy today, how could you do it? What works? What have we seen? How does that connect?

Obviously, if having a different level of agenda on diversity, on inclusion, on participation, on sense-making, et cetera, if that’s part of it, then you’ll see that show up in all the ideas themselves.

JENNIFER BROWN: Agreed. It’s interesting, we have a whole chapter on purpose. You probably know Aaron Hurst, who wrote The Purpose Economy, and the Imperative Index, the index which measures purpose.


JENNIFER BROWN: One of the most startling facets of their research findings is that 50 percent more women identify as being purpose driven. I thought it was fascinating because the gender difference is, perhaps, something you would suspect, but to see it laid out like that, this is women of all ages, too. Those who are purpose driven don’t necessarily just inhabit one generation, as we might expect they would. The millennials don’t get all the cool stuff all the time.


JENNIFER BROWN: We see it throughout all generations. Each one of these that you listed off, I could imagine it is fundamentally defined so differently for what I might call “majority culture” if we’re talking about mostly white, male culture, and everyone else if I can call it that.


JENNIFER BROWN: Maybe women, people of color, LGBT people. For example, you and I were talking about the different sets of skills that you think each gender needs to move into that are fundamentally different learning plans for each gender. We have different journeys that we are going on in order to meet in this participatory, flat, agile, welcoming, open environment where we feel all of our voices are head.

I’m curious. What is different? What different coaching do you give your male clients versus what you would give women stepping into this new space that you’re trying to create?

AARON DIGNAN: Obviously, these are generalities, but you definitely notice patterns. When you talk about masculine energy or feminine energy through this change process, you see a lot of different patterns and habits show up.

Certainly, it’s much more common for men to have challenges with being vulnerable at work, listening rather than talking, giving up control to the system. Even to your point about purpose, spending time with the self. Self knowledge, looking within. I don’t want to do that. I’m going to go out and knock down these goals, as opposed to asking, “What do I really want?” Do I stop and listen to that, or am I afraid of listening to that?

You see those things come up a lot because a lot of the systems we work in are either male dominated or have a disproportionate number of men in power versus women, a lot of our techniques are about holding and protecting space, creating vulnerability, creating psychological safety, learning how to listen, perspective taking all that kind of stuff. That’s what’s most needed.

In many ways, we find that our female clients, or our clients who show up with a more feminine energy, can meet us right there and can just play because they’re much, much better at equal talk time, empathy, emotional intelligence, and participation being the norm. That means that we can step right into that. There’s an ease with that audience.

However, what we find is that because these systems have been imbalanced for so long, when you start inviting everyone into the change to try experiments, to take risks, to fail, et cetera, the reality is that a lot of women or people of color, people of any kind of difference who have been sidelined in some way, shape, or form, are typically a little bit more risk averse. They’re going to wait to act, they’re not going to jump in fully, they’re not going to show up whole at the drop of a hat because maybe they’ve been burned before. There’s a little bit of just being suspect about these invitations to lead and to be part of an emergent phenomenon.

We don’t necessarily always get earnest participation right away, we get a little skepticism as well, and then that can even be validated by the unconscious behavior of the leaders, or invalidated by how they follow through. So we have to pay very careful attention to the early signals and feedback on experiments people take, risks people take, and how they show up.

There is definitely a difference that we see, and a lot of it is allowing both sides to show up with their natural gifts, and also be self-aware about the things that maybe are holding them back and come in with a fresh slate or a clean slate to meet in the middle, essentially.

JENNIFER BROWN: Yes. You just articulated that. You describe the trust that is needed in the changing of an institution. All of a sudden, we’re going to do something a different way, why would I believe that my experience is going to be any different?


JENNIFER BROWN: When you’re on the receiving end and perhaps nobody has called out institutionalized biases, whether overt or not, whether intentional or not, it is the experience for so many people every day. And to say, “We’re going to do things differently, I’m going to show up differently as the leadership of a company.” Show me. Show me. I’ll believe it when I see it, and I’ll believe it when I see it consistently practiced over time. Then I will come to the table and feel like I can learn to trust again.

AARON DIGNAN: There is a level of trust that needs to be achieved where face-value behavior is not perceived as inherently negative or misrepresenting what’s going on. So someone can, out of pure muscle memory or habit, say something or do something in a meeting that smacks of old-guard, old-world, non-inclusive behavior, but they’re earnestly trying to worrying on it. They’re there. There has to be a level of trust and awareness to notice, name these things, talk about them, and not to get too wrapped up in any one behavior that we then lose the trust, lose the plot, and it becomes a “you said, you did” kind of accusation. It should be more about, “We’re all working on this, we’re all navigating this together, and the only way to get there is through constant feedback, communication, and openness.”

JENNIFER BROWN: I love it. How have you instituted this? You’ve run several companies. At The Ready, your current project, how have you built in that feedback mechanism for open conversation – difficult conversations that require trust? I couldn’t agree more. Both sides need to come together and say, “That comment or choice wasn’t negatively motivated, it’s a byproduct of habit and a lack of awareness,” which is not a crime. If we cannot elucidate those things and talk about them openly, there’s going to be no learning, and everyone just goes into their corner.

AARON DIGNAN: Right. Then they just close down.

JENNIFER BROWN: What techniques do you use internally with the team to perform that hygiene, if you will?

AARON DIGNAN: Some of it is built into the system itself, some of it is built into how we meet, et cetera. At the highest level, one of the biggest changes I made in building this system – the last system, I basically hired for comfort. I hired people who felt like me. What I ended up with was a lot of people who were not entirely like me, but we were very homogenous as a culture.

It was great. It felt great to us, but it wasn’t necessarily inviting to everyone else, and it became a limiting factor later in the company’s history.

This time around, the thesis was: If you’re looking at two or three candidates, options, or things you can do, and one of them feels more uncomfortable because there’s something about it that you don’t understand or that’s not as common to you or usual and typical to you, then go with that.

Generally speaking, just trying to invite in more difference through that sense of discomfort, frankly. I don’t really know exactly how I feel about this, I like that. I’m going to lean into it and find out how to become comfortable with it, understand it more, and how to be part of it.

That gave us a system of people. Obviously, we’re always working on this, but we have a lot more present diversity than I’ve had around in my companies in the past. That gives you a place where now you have more noticing. Right off the bat, there are things happening now where people are calling out, “We’re talking about this in a very gendered way,” or “Half of the room hasn’t talked right now.” I was in a meeting the other day where one of the gentlemen I work with said, “Hey, did you notice how the men sat on one side of the room and the women sat on the other side of the room?” Just noticing.


AARON DIGNAN: That’s one thing. The second thing is defaulting to open, which we talk about, and which a lot of my former colleagues talk about, which to me means when I hear a one-on-one conversation come to me about a tension or a concern that might be very private or personally felt or isolated, I invite people to bring that back out to the group. And so we have a whole channel for generative difference that we use on Slack. We have meetings during the week where we have opportunities to bring up these kinds of conversations. I try to funnel things back to the shared consciousness rather than deal with them in one-off capacities as much as possible. That creates a habit of sharing.

The third thing is that there are components built into the way we meet and work together that require participation and voices. We check in and out of every meeting, we work a lot of our meetings in rounds, we meet in spaces during the week where we talk about what we learned, what we noticed, what went well, what didn’t go well. We really try to encourage those conversations to steer towards these issues as well as just the work itself. It’s just about having trust and a safe space and having a trigger of, “Let’s just remember to talk about this stuff on these occasions or with this frequency.” It becomes a habit on its own.

JENNIFER BROWN: I love it. I know you’re seeing and encouraging what I would call in my world “ally behaviors” on behalf of men, which includes things like listening, noticing, building awareness, saying something. To use your example, redirecting a private conversation to a public one. Even that hits a nerve for a lot of women, in particular in large corporations who always have that sense that they’re outside of the power structure, that they’re outside of the decision making because of their social networks, because they’re not invited in, because it’s the guys – fill in the blank. That’s still rampant in a lot of my clients anyway. Maybe not your clients, because your clients are ready for change.

What are the key behaviors that men can employ? You’ve listed some already, but how can they learn to be better allies? What is some of the hesitation to do that? If you can imagine an old-school corporate environment, which is probably more of our audience, they’re not as evolved. How can we get more men to step up and use that platform and their voice, and frankly, their social capital and power to challenge the norms, versus the women always being the squeaky wheel?

AARON DIGNAN: That makes sense. Part of it is at some level, people need to have a personal awakening about what they care about and what matters to them. We’ve designed different kinds of ordeals and experiences. We are even talking about rights of passage right now with one of our partners on the west coast to get people out of their element and doing more considering of what they value and how they wanted to show up.

The second thing that I talked about before is once you recognize that a lot of these practices and principles and habits that are typically more associated with a female perspective are beneficial in the work environment, then you want to step into them. A lot of it is about making these things safe by demonstrating their viability and the reality that we’re in that world now where we need those skills.

In terms of ally behavior, a lot of it is listening and a lot of it is listening carefully, thoughtfully, and noticing regularly. When you hear a piece of feedback, putting it somewhere where you can access it again, notice it again, and start to become part of being watchful over that particular thing.

It’s funny because sometimes it folds in on itself. So we have this channel I mentioned in Slack where we talk about these issues. One of our men noticed, he said, “The last 12 posts have been from men.” Different links to articles and things that all are about this issue. And what does that tell us? We are now not inclusive in our inclusion channel. (Laughter.) What’s going on? That level of meta analysis goes on, which is interesting.

The hesitation for a lot of the men we counsel and coach in our client systems is that these things become hot so quickly and dangerous. The uninitiated man doesn’t know where the edges are and where is it important to stand strong or to listen or participate? And if we were to challenge an idea or challenge something, does that immediately make you the bad guy, the other, the one who doesn’t get it, who’s not “woke”? It’s very easy for it to become an “us versus them” thing.

I’ve met a lot of guys, myself included, who have been in systems or moments where you think, “I literally don’t know what I can say or how I can say it and not offend somebody.” I purely come from a background where I built up this whole way of perceiving and participating that is inherently biased. And I don’t have a way to navigate that. Now I feel completely neutered and neutralized by the awareness that that’s all bad, but without the skills for how to participate in a positive way.

Sometimes I think the energy around this stuff actually exacerbates that. So people feel like, “Well, fuck it, then I’m just not going to play or I’m not going to talk or I’m just going to wave this off as nonsense.”

In some cases, I even feel that it can become that. It can become this game of which words are we going to use? Every word has meaning, and we argue to the point where I feel like I’m in an academic environment rather than a workplace, and I’m waiting for the group to say, “When does this stop being productive and start becoming cyclical and recursive? And when does it become helpful, educative, and we’re actually learning as a system?” I feel like sometimes we don’t have a good sense for that, so that can also derail this stuff.

JENNIFER BROWN: Again, very interesting, and so true. Trust is built with many steps, and broken with one. These things can go off the rails if there’s not a lot of good intent, if there’s not a lot of openness, a little bit of policing, creation of ground rules, safety, and all those things. Then both sides can say, “Look, I don’t have all the answers. I need to be coached, and I need to be able to ask questions that I have without, quote/unquote, triggering others.” This is such a tricky spot. We’re seeing it play out on campuses, right?


JENNIFER BROWN: People saying, “I don’t feel safe because you’re a speaker on The Bell Curve.” That was my alma mater. The whole thing happened when the guy came and everybody walked out and he was physically attacked just for coming on campus.


JENNIFER BROWN: It makes me wonder, “How would I be playing that if I were 20 again?” I’d love to know where I would stand on the protection of free speech. As this election showed us, it’s very important to learn that turning a blind eye to other people’s experiences that trigger us, make us uncomfortable, or that we don’t agree with – that’s not the solution. How can we build more inclusive conversations without doing that? Because we’re truly being exclusive.


JENNIFER BROWN: It was a big wake-up call for a lot of us who do this work to say, “Have we really been inclusive or have we been practicing our own style of being the inclusivity police, if you will?”

AARON DIGNAN: Right, which is, in and of itself, also separating everybody into groups. It’s funny, at the highest level, it’s really just about prioritization and understanding as a collective, “Where are we going to focus? What matters most right now? What unlocks a future thing that matters?”

It’s silly if we’re an environment where we don’t have equal representation or distributed power and we’re arguing about this object in the boardroom feels like it has too much of a masculine energy, well, that’s interesting, but maybe we should get on those recruiting policies. Maybe there are some bigger fish to fry. Sometimes we throw this energy that we have for this topic at the wall, shotgun style, rather than starting as a group that is committed, and that obviously is its own first step, but as a group that is committed, let’s be deliberate about where can we focus? Where can we change behavior? Where can we make some headway to unlock some of the deeper and more nuanced stuff as well?

JENNIFER BROWN: Totally agree. Tell me, you co-founded a community with another Will to Change podcast guest, Adam Pisoni, which is so cool. You started You wrote a manifesto. Can you tell us about that manifesto for the future of work? It’s launched several conferences now, which I never miss, speaking for myself. I find it so fascinating, stimulating, and it gets to the heart of diversity and inclusion because I think the future of work, if it fulfills its destiny, is going to be inclusive, participatory, and hopefully something that truly inspires all of us, versus feeling like drudgery. That’s my deepest wish for everyone, that they feel aligned in their work and feel their work as a calling. Right now, that is so far from the reality for so many people.

Why did you begin that community with Adam? What excites you most about where that conversation is going in the Responsive community?

AARON DIGNAN: What’s funny is that Adam and his colleagues, and my colleagues and I started two different Responsive.orgs basically at the same time. They actually became one when we found each other and realized, “Oh, wow, we have the exact same intent here.”

JENNIFER BROWN: Great minds.

AARON DIGNAN: The intent was to create a more decentralized platform for this conversation. There wasn’t a lot of shared language and there wasn’t a lot of community at the time, at least from our view, around these new ways of working and organizing and this future of work that was allowing people from a lot of different walks of life to come together and learn and share what they were trying and how it worked, et cetera.

We felt that one way to do that was to create a common language, a brand, and a community that people could gather around. We modeled it after the Agile manifesto that created the first kind of Agile software development movement or at least put a pin in it.

We made a set of statements. From profit to purpose, and thinking about basically this move from efficiency to adaptivity at scale and how that would change the way we work and change the way we show up.

What was interesting was we did it fairly clinically and fairly scientifically. It was mostly about adaptivity and being human at work and having meaning and purpose in the work.

As people flocked to sign the manifesto and become part of the Slack channel community, and ultimately the conference community, they imbued it with a lot of other meaning around the issues like what we’re talking about and a lot of other things as well. Now it’s a pretty broad, open tent in terms of what you can bring to the table because it’s just about, “What’s the future of work that works for everybody, that works for all of us?” And it can hold a lot of different expressions of that.

But the idea is to get people trying this stuff, talking to each other. It is a long and lonely road if you’re trying to implement these changes in your system or client systems and you don’t have people to talk to about it.

JENNIFER BROWN: Yes, I know. I have noticed in the Responsive conferences, especially, things that I’m looking for, like gender diversity, are very well represented. Diversity of ethnicity, et cetera, amongst speakers, for example, these are the kinds of things I notice. There’s so much effort being made around that, which makes sense. If we talk about the balancing out of that patriarchal management style with the historical absence of women’s voices from a leadership position, we have been out of balance. Any grouping or gathering that is talking about the future of work, I’d be surprised, although not shocked, that it wouldn’t have diversity as one of its core tenets. Honestly, that’s one of the big things that we’re missing in so many institutions. It’s not the root of everything, but certainly one of the main reasons that some companies have gotten into major trouble.

I want to segue and ask you a quick question about the scandals we read about. Whether our friend Travis at Uber and that whole story with the female employee who blogged about what it’s like to work there.


JENNIFER BROWN: Whether it’s banking scandals like what Wells Fargo is going through. You must be having a field day thinking about these old-school companies, but also these new, fast-growth companies making the same mistakes in a way. What is going on? Why do we keep reading these headlines? What is it about organizational structures that are not nipping these kinds of things in the bud and building things fundamentally differently from the very beginning? Why are they still continuing to build dysfunctional organizations which result in these kinds of stories?

AARON DIGNAN: It’s a fascinating and depressing topic.


AARON DIGNAN: A few years ago, we were all thinking of the Valley as this great hope for mankind where the way they work is so great, right? It turns out, that’s not the case.

I think there are two things going on: One, a good friend of ours, Doug Rushkoff, wrote this book, Throwing Rocks at the Google Bus, which was all about how the economic operating system is addicted to growth at the detriment of prosperity. Actually, we do a lot of extracting capital and trapping capital in the system that basically slows down the wheels of progress and prosperity for a lot of people.

One of the things that’s happening is that those systems, those venture-backed systems, are part of our economic OS. And so the mission and the message to them is: Grow at all costs. Very proto-masculine ideals of domination, monopoly, destroy the industry. We use words around how these startups operate that are very, very much about control and domination.


AARON DIGNAN: Of course, then, they go make decisions to do that stuff, because that’s the message. Worst of all, they’re all about exiting and getting out of those systems once they’ve become extractive. So you have people who pass the bag on to the public in the form of a publicly traded stock that now is governed, but it’s already lost its soul, and it’s lost its connection and it’s done a lot of, frankly, semi-destructive things to the economy along the way.

That’s the darkest way to look at it, right? There are a lot of positive examples out there. There are Kickstarters and systems like Airbnb that are trying to meter that and measure that with some meaning and connection to community, so I don’t think that it’s inherent in the system, but it is a strong undertone that the economic OS says, “Grow, grow, grow at all costs, and do any kind of dominant behavior to get there.” That means that when you have a great engineer who’s accused of abusing someone or abusing their position and taking them out would mean it might hurt growth, well, we can’t do that. Then it becomes this battle between those two ideals. That’s one thing that’s happening.

The second thing I think is a lot more curable. We inherit so much of our operating systems from the people we bring to the table. And what happens with systems that we see in the Valley or startups around the world is they start with a pure energy and a set of founders and participants who are highly engaged, highly plugged in, values driven, et cetera. As they scale, they require the need to bring on, quote/unquote, adults or they feel the need to bring on adults, or their investors tell them to bring on adults.

What those “adults” bring is decades of muscle memory from old operating systems. So when you hire the VP of sales from Oracle to come into your system, they bring Oracle’s operating system with them. And as much as there’s a melding of the two that goes on, a lot of bad habits get imported, and a lot of things that maybe no longer apply, et cetera. So you get a watering down of the operating system of the startup, and you get a watering down of some of those values and that participation. That is, ultimately, what screws things up as you get that combined with the drumbeat of that economic growth OS. It creates a really tough environment to get it right. And the ones who do, you can fit on the head of a pin.

JENNIFER BROWN: I know. You’re reminding me of a point that Jack Myers made on an earlier episode of Will to Change. It’s provocative, but he says as a baby-boomer man, he’s a specialist, The Future of Men is his book. One of the things he says is, “I would never want the older generation of men mentoring and coaching the younger generation of men.”


JENNIFER BROWN: He said, “That is not what we need.” We don’t need more of that because they will imbue this younger generation with this supposed advice that is literally passing on this imprint and this toxic masculinity, which is what he calls it. We have these younger generations of men, of course, coming up who have been raised in a very different world. They’ve seen different gender roles, they believe in inclusiveness as one of their top organizational values. They already come into companies and are dismayed and confused by the behavior they see tolerated by what the masthead looks like and the lack of diversity in leadership. Maybe the rolling of the eyes when the conversation about diversity is had. A lot of them are surprised, shocked, and feel like they’re in a foreign world when they walk into the business world.

That’s related, of course, to the rapid turnover that we see for that generation. They say, “Not only are my values not aligned with this company, but the company doesn’t value inclusiveness and really walk the talk when it comes to valuing. They may get awards, but my lived experience every day does not square with that.” So they’ve always got one foot out the door.

That’s for men and women. It’s for younger men who, because of the way they were raised, are naturally more ready to be gender champions and champions for diversity.

An interesting side note: Millennial men do answer the question differently than millennial women about opportunities for women in the workplace.


JENNIFER BROWN: When asked the same question, they definitely have a rosier view that things are more equal than the women. I think that’s interesting. I was surprised by that. I wonder if some of that older generational thinking is reaching that younger generation, notwithstanding our efforts.

AARON DIGNAN: Well, we’re chameleons, right? People are incredibly good at absorbing the culture that’s around them and becoming a part of it. That’s what we do. We’re tribal. I think one of the dangers is you take somebody who has come up through the system and is a young man who has a wider view and brings a lot of good habits to the table, and then you put him through a decade of systems that are still stuck 20 years ago because that’s the rate of change inside these systems, and yeah, you’re going to get weird rub-off and weird new habits forming, and even incongruent feelings that become a malaise, lack of purpose, or a lack of meaning at work and things like that. I think there’s a lot of that, and not just with diversity and inclusion, but with the operating system in general empowerment, connection, transparency, purpose, meaning value all of it. We show up to these systems and think, “Huh, this doesn’t look like what I thought it was going to look like. I’m not sure I like it.” And then once they have enough self-awareness to see what that’s doing to them, they bounce and get the heck out of there.

JENNIFER BROWN: That’s right.

AARON DIGNAN: The great irony, though, is then they go found startups that slowly inhabit and acquire those same traits sometimes as they scale. We have to break the cycle at a fundamental level, and that comes through being deliberate about it and not ever forgetting that. That’s where we are.

JENNIFER BROWN: Hear, hear! Oh, my goodness. Well, we’re out of time, but this has been super rich. I love it. My brain is firing, there are a lot of lights going on.

Aaron, it’s so cool to talk to you. I want folks to be able to find these Slack channels and conferences for the Responsive community. Tell us what we need to know to find you, more information about your work at The Ready, and also the Responsive dialogue that’s going on.

AARON DIGNAN: is a good place to start. That’s where you can see the manifesto and join the community there. Responsive Conference is another one, that’s a Google search away, and I think the next one is here in New York in September.

JENNIFER BROWN: Yes, exciting.

AARON DIGNAN: has all the links you need for our work, so you can get to our writing from there, you can get to the OS Canvas from there, videos, et cetera. That’s the one stop for what we’re doing in this change work. I’m @AaronDignan on Twitter if you want to shout at me there.

JENNIFER BROWN: That’s great. And we need a book from you soon, yes?

AARON DIGNAN: Yeah, there is a second book. My last one was four or five years ago. There’s a second one in the works now, so that will be fun. I’m finishing up the basic structure of that as we speak. That’s probably a year away or so.

JENNIFER BROWN: Good. I’m glad to hear it. Very important that your voice is in the mix.

Thank you so much for joining us today. I appreciate your time, Aaron, and keep up all the amazing work.

AARON DIGNAN: Likewise. Thanks for inspiring us.


Aaron on Twitter

The Ready


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