Building the New Workplace: Leading Change through Turmoil

In an environment fraught with social injustice, environmental degradation, and uncertainty around the future of work, how do change-oriented leaders remain positive and continue to lead the charge in creating a more equitable and ethical world, both in the workplace and more generally? Innovative strategist and change management expert, Caleb Gardner, joined The Widest Net Podcast host Pamela Slim to provide his personal and career insights into this question, including drawing on his experience running former President Barack Obama’s Twitter account.

Here’s the full transcript from the episode:

Introducing Caleb Gardner

Pamela Slim  00:04

Welcome to The Widest Net Podcast. I am extra excited to welcome Caleb Gardner to the podcast, who is my friend. His career has spanned from consulting with Fortune 100 CEOs to running President Obama’s Twitter account, including respected companies such as Bain and Company, Edelman, and OFA. As a thought leader in digital innovation, Caleb has been a featured speaker at Social Innovation Summit, South by Southwest, Inbound Marketing Summit, among many others, and he has been quoted in Wired Strategy magazine, NBC News, BBC Radio, and others. His brand new book, No Point B: Rules for Leading Change and The New Hyper-Connected Radically Conscious Economy was released this year through Ben Bella Books. Welcome to The Widest Net Podcast, Caleb.


Caleb Gardner  00:56

Thank you so much for having me. I’m excited.


On Working for Former President Obama

Pamela Slim  00:58

Me, too. Well, I am not going to bury the lead, because anybody who heard your background was like, “Hold on. Wait a minute. How in the world did you end up running President Obama’s Twitter account?” So, let’s just start there.


Caleb Gardner  01:11

How in the world? Well, I mean, being at the right place at the right time is honestly the unsexy answer. I just…I was working in digital strategy and social media at Edelman, which happened to be across the street from the 2012 presidential campaign for Barack Obama. And so, we just happened to cycle through talent with people who went from the campaign, who came from the OA campaign to Edelman and then went to the 2012 campaign because we were literally across the street. And so, you know, I got to know the chief technology officer on the campaigns and people that were in this social media team. And then afterward, they were like, “Hey, we’re causing…we’re building this version of OFA that’s going to be post-presidential. It’s going to help with, you know, policy implementation for the second administration. I think you should apply for this job.” And I was like, ‘Wait, you want me to apply for what?!’ I was like, ‘That’s the most insane job I’ve ever heard.’ And so, I did, and the rest is history.


Pamela Slim  02:16

And OFA, for those who don’t know, is what? Because I think it’s interesting for people to know just what the acronym means but also the nature of the organization.

Caleb Gardner  02:25

Yeah, so the OFA is the umbrella acronym for what started as Obama for America, and then was Organizing for America, and then was Obama for America again, and then was Organizing for Action. And then eventually – I don’t know – there was also a post-presidential OFA, and I don’t remember what it stood for. But it basically…that became the political advocacy slash campaign side of Obama’s political engagement for many, many years. And I just happen to be part of, you know, Standing on the Shoulder of Giants, part of one segment of that, basically.


Pamela Slim  03:02

For sure, and just what, like…what did that involve on a day-to-day basis?


Caleb Gardner  03:07

It involved a lot of content creation and approvals. I think we went through…because I was running the social media team, and then the social media and email team, and then eventually the entire digital department. A lot of content had to be written and come through me every day. And so, what it required of me was just trying to look at every single thing we were Tweeting, and writing in emails, and all the content we were producing every day and just saying, ‘Is this going to get me in trouble with Josh Earnest because he’s going to get asked at the White House press briefing why this Tweet was phrased this way?’


You know, like, it was a lot of very stressful content approvals on top of just campaign strategy, trying to figure out, okay, we’ve got this policy agenda we’re trying to help, you know, help get across the hill in terms of the minimum wage, or climate change, or any of the issues the president cared about. Like, how are we going to rally people to care about it as well, and really step up and donate to issues, you know, support people in office who were actually supporting those issues, and generally kind of support what the president was doing every day?


A lot of reacting to news cycles, you know, obviously. There was…we could not plan too far ahead. We knew what the president’s plans were. We knew what our friends on the Hill, what their plans were. But then things happen. There are school shootings. There are, you know, international crises. There are lots of different things. And so, we had to be prepared to, you know, turn on a dime and really react to that day’s news cycle.


Content Creation for a Global Audience: Being Researched while Remaining Nimble

Pamela Slim  04:45

And I’m just curious, because in that role, it just fits so well with so much of what you talk about in the book and just your work day-to-day since that time. But just imagining needing to synthesize information, needing to address real-time information that was coming in, I’m just curious from an actual team perspective, did you lay out knowing, for example, some of the key elements of President Obama’s platform? And did you have, like, team members that were going off and researching different things? Did you have like some Iron Man dashboard in front of you with, like, things flying in? Like, what did it actually look like on a day-to-day basis to both have some research but then also be responding to real-time information?


Caleb Gardner  05:34

That was what was so interesting about being in the role that I was in, because you actually got to learn the limitations of big data. I mean, we had access to some of the biggest datasets you could imagine, and only so much of it really helped us make day-to-day decisions. The rest was interesting and might help us think about long-term strategy, or new ideas, or whatever. But in terms of what we would pay really close attention to, I mean, it was a relatively small set of numbers and data points.


But to go back to your question about team structure, we had people that were on research, people that were on policy. Those were the people that we relied on a lot, just can we phrase this in a way that is capital-T true or if we change this particular type of phrasing? Especially when you’re trying to get something into 280 characters, right? We had a lot of…we need to condense this so people understand it or tell it across different pieces of content to where it’s a cohesive story. But if we change the narrative in this way, is it still going to get at the policy goals we want to get at, or is it going to, you know, change the truthiness of it? You know, is it really going to not be what this study that we’re citing, for instance, actually says anymore?


And so, we had people gut-checking us on that, people gut-checking us on just our relationships with, you know, people in the Senate, and people on the House, and people in the White House. We had, you know, people that just understood, you know, the political environment that we were operating in in Capitol Hill – and not just Capitol Hill, all of DC – and how people are going to react. So, we had people that were smarter than us really keeping us up-to-date.


But to be honest, a lot of those day-to-day decisions, only about 20% of what we were producing on any given day I would estimate needed that kind of extra level of attention. And not only did only about 20% need it, but only about 20% could have it, because we just had such a content burden in terms of what we had to produce every day. So, 80% of what got produced and published on any given day basically went through our writers. And there was a peer review process, and then it went through me, and then it went live. So most of what came on the Barack Obama accounts in those days was, surprisingly, from the standpoint of my corporate friends, you know, didn’t have as much governance as you would expect. It was only the, like, super sensitive things that really got a little bit more eyes on the ball.



Pamela Slim  08:09

For sure, I remember the first time we met in Chicago, and we were having lunch, there was something that happened. You’re like, “Excuse me. Like, let me just look at my phone and make some adjustment or response.” To that I was like, ‘Did he do what I just thought he did, which was hold the President’s you know, Twitter in his hand?’ So, that just…it boggles the mind when we start to think of – and you know this well as an individual business owner – just the difference sometimes between how overwhelming it is to be creating content and sharing for not just your own platform, but to be thinking about doing it on really the global scale, knowing who was paying attention, must have been just quite awe-inspiring and challenging.


Caleb Gardner  08:48

Yeah, definitely. I was less gray when I started that job than I am now. It was a high, high pressure situation. But on the opposite end, you just mentioned being a business owner. Now I have people who are like, “Oh, you’re an entrepreneur. That must be so stressful.” I’m like, ‘Yeah, I’ve had stress before. This is not stress.”



On The Radically Different Communications Approach of the Trump Administration

Pamela Slim  09:09

This is not it. The last follow up I’ll have…and it’s interesting and so many people who do really amazing work…you’re talking about some of the infrastructure and processes and everything you went through on Twitter, in particular for the President. All of us know, having lived through the cycle of the president who followed, that it really was quite different, quite a different experience. And I’m just curious, for you personally, was there any part of you who just withered, was disappointed, was like out of sorts with what was happening? Because sometimes when change-makers like yourself, like, do something really big and substantial, and then maybe you see it immediately dismantled, you know, with a shift, how did you feel when you saw what was happening, with Twitter in particular?


Caleb Gardner  09:55

Out of sorts may be the most mild way to put it, I would say. I mean, a completely different approach, both in terms of, I mean, just substantive policy differences, of course, but also in terms of just infrastructure and how they thought about, literally how they thought about the law around how you engage in communication mediums from the White House. I mean, there’s something called the Hatch Act, for instance, which is supposed to prohibit people who are in specific political positions from advocating for electoral – I don’t know exactly what it says – something about, like, you’re not supposed to basically advocate that specific people get into office from a seat at an administrative position like the presidency. I’m going to butcher…there’s going to be people who are going to leave in the comments, “That’s not what the Hatch Act says.” It’s something like that.


Regardless, we thought about it a lot from our communication mediums in terms of what even could be perceived like the President was advocating for specific people to be elected or specific people not to be elected. Most Trump administration officials not only didn’t care, but they didn’t really get punished for it. Like, obviously, the President himself kept his own personal account as part of the his official office communications. They still had the @POTUS account, but really the @RealDonaldTrump account was the official account of the president for that entire time. And all the administration officials pretty much just Tweeted whatever they felt like, and they got slapped on the wrist for it a few times in terms of the people that would actually investigate it. But, I mean, we have learned a lot about the boundaries between what we consider just norms and expectations for people, around what will be enforced.


But I think they took a lot of advantage of the fact that a lot of our newest digital communication mediums are so new that there are not a lot of guidelines or, you know…like, we’re operating on a, you know, legal infrastructure that is based on Telecom, you know, infrastructure that’s decades old. Like, we’re not…we’ve got yesterday’s tools to solve tomorrow’s problems. And, you know, there’s a lot of ambiguity there.


Building a Socially Conscious Business

Pamela Slim  12:16

Yeah, I so appreciate that. Well, it dovetails into one of the core reasons I was excited to bring you in, knowing that your book and your body of work, it definitely intersects with mine. I know I’ve always felt a lot of synergy in the way in which you describe the work you do from completely different perspectives in terms of client. It’s like looking at it from different angles, from different client bases.


One of the things that you said in No Point B is, having been in rooms with both CEOs and political activists over the last decade, I become increasingly fascinated with the idea of a socially conscious business, one that tries to operate in a complex and connected world with some degree of ethical decision-making. So, for you, how do you approach answering that question when making choices about what work that you do? In what order?


Caleb Gardner  13:10

Yeah, I mean, let’s stipulate that it’s hard. And I think it’s harder than a lot of people give it credit for. I mean, I think there’s a lot of, let’s say, Twitter users – since we were just talking about Twitter – who will kind of bash company leaders and bash, you know, entire industries, really, for not doing the right thing or not doing better. And, actually, sometimes better is hard to navigate. And I think it’s harder than a lot of us who aren’t business leaders give it credit for.


And so, part of why I love doing the work that we’re doing, and honestly, I think part of the reason why my whole career has kind of pointed in this direction, is because I do think that we have the opportunity to use the engines of economic progress – both individually as business leaders in terms of how we do business but also kind of corporately, as you know, we’re redesigning the economy coming out of COVID – to do it in a way that is more inclusive, and circular, and regenerative, and not exploitative, like it has been. I think that that could make a huge difference to a lot of people’s lives, and I think a lot of business leaders, to be honest, want to do the right thing, and they want to do it in a way obviously that helps them be profitable and helps them, you know, still be innovative in the way they do business, but I don’t think anyone – most people; I shouldn’t say not anyone. There are some people out there –most people don’t want to be exploitative, or they don’t want to be about profit only. It’s just a matter of how. How do we actually do it? And I think that “how” question is a fascinating one with not a lot of easy answers. So, we have to find the answers together.


Holding Onto Optimism Through Dark Times

Pamela Slim  14:56

Yeah, do you hold hope and optimism in the face of such gigantic challenges that we face in pretty much every single aspect of our life and planet?


Caleb Gardner  15:15

Woah, woah. That went downhill really fast. Do you hold optimism in the fact that everything is terrible? I do. I do.


And you know, I think it’s, for a lot of us, to find the context in which we can, like, find hope, right? Like, I think it’s…we look at all of the world’s brokenness at once; it’s very easy to feel hopeless. But if we can find the context where things are good and things are moving forward, and we can see progress, I think that makes a big difference in terms of our ability to be optimistic. Because the world is always going to be broken in a thousand different ways. That’s just…that’s part of how it atrophies. It’s part of the chaos of living in a modern world. But finding our own context is how we both make a difference – you know, the only way we can make a difference is by carving out a piece of the world that we can actually influence – and it’s also the way that we can feel more hopeful, because we can see micro areas of progress without having to be overwhelmed by everything else.


Pamela Slim  16:19

The book that just came out, that was your first, correct?


Caleb Gardner 

It was.


Enacting Positive Change at the Corporate Level

Pamela Slim

Yes? Okay. So, how did you approach writing it? I’m imagining that, like, as we do with many books, it’s not necessarily the entire answer but, like, a framework, maybe, for thinking about how to make positive change, right, in the world. Who did you write it for? And, you know, you can help describe kind of the core premise and especially what you hope that people will take away from the book.



Caleb Gardner  16:51

Yeah, I had, in my mind, a future business leader that was tackling things like DEI initiatives, or ESG, or any of these kinds of big, meaty intersection of social impact and business type issues that tend to be really sticky, again, that we talk about, like, as if they’re really easy, and we just have to go do them. But actually in implementation, they’re really hard. And they’re hard because we don’t have a lot of good shared definitions of what a lot of these things are. They’re hard because they have an emotional resonance and a political resonance that sometimes is underappreciated and in workplaces are messy, you know, intersections of human dynamics, of people that believe lots of different things.


And then they’re hard for the kind of traditional change management reasons, which is that people don’t want to change. They have a job that they like doing. They don’t want to be told that they should operate differently. And trying to get any kind of big bureaucracy moving in a different direction is super hard. So, taking that kind of base-level change management expertise, and then you add in all these emotional and political and all these things that make doing something like ESG really hard –


 Pamela Slim  18:03

And define just what ESG is, for those who don’t know.


Caleb Gardner  18:06

Yeah, it stands for Environmental, Social, and Governance. It’s basically, like, an operating framework for trying to report, especially for financial purposes, the social impact of a company. You know, a lot of companies are looking at it for thinking about things like net zero impact, for example. But I think increasingly, their efforts toward diversity, equity, and inclusion are going to start being reported out as part of the ESG framework. But don’t…


Pamela Slim  18:44

Oops, you just froze for a second. Let me see. All right. So what we’ll pick up for Jose: I heard you say with for ESG. And then you froze, and then we went away.


Caleb Gardner



Pamela Slim

I know. So, it’s kind of picking up on, yeah, the reasoning for the book and really, like, what you hope people will take away from it. So, you could just pick up with what you hope people take away.


The New Rules for Leading Change

Caleb Gardner  19:10

Yeah. So, I really hope that…you know, I structured the book, like the new rules for leading change. And the reason why I felt like we needed new rules is because we’re operating in an environment where the amalgamation of the political environment we’re in, the social environment, the technology environment is creating different kinds of change challenges within an organization that make it hard to do traditional change, like any kind of traditional transformation, but then make it especially hard if you’re trying to do something like learning about ESG, environmental, social, governance. DEI, you know, how do we bring all our people along, make them feel included? You know, some of these things that have a little bit more emotional resonance and that are a little bit harder to define because we don’t have shared definitions or shared standards.


And so, I was really trying to write a book for people who were looking to kind of that future of business, looking to do business more inclusively, more regeneratively. More, like, you know, the economy that we need to build, not the economy we have had.


Pamela Slim  20:26

Well, congratulations for writing it, because I know we were checking in a little bit through the writing process, but it is not easy to create.


Caleb Gardner  20:34

Tell me about it. I respect anyone who has written a book now. Even if it’s a terrible book, even if it’s something I’ll never want to read, anyone who has sat down and done the work and, you know, produced, I’m like, respect. You know, it’s a process.


Pamela Slim  20:51

Well, you did a great job. And it is something, I think, that I’m always looking for in somebody’s body of work and just looking at tools that we can use to have frameworks and different ways of thinking. Because it is just…it doesn’t work to be looking often at the tools that we’ve used in the past.


Caleb Gardner  21:09

Yeah. And I would say, not only does it…I had to – I’m sure you’ve done this when you’ve written books, too – basically, like, shut down for the writing process my, like, intake of other people’s ideas, because I found myself, like, being influenced by them. And I’m like, ‘No, I can’t.’ Like, the more, like, while I’m doing this, producing this book, I can’t, like, take in new ideas, because it keeps getting muddier and muddier.


At the Intersection of Digital Disruption and Social Disruption

Pamela Slim  21:34

It is 100% true. One of my past colleagues and current friends, Charlie Gilkey, who was on the podcast a couple episodes ago, has a framework that he calls “Create, Connect, Consume.” And it’s when you’re creating content, there’s a time where you’re consuming and gathering ideas and connecting with other people to share, bounce ideas, do research. But then when it comes to the creation, you need to cut those things off. 100%.


In the middle of writing, people would be like, “Oh, this person read a book on ecosystems.” And I was, like, putting my fingers in my ear, not wanting to hear it, because you have to hear your own voice. And, you know, for good, bad, or otherwise, once it’s done, then you can do a little double-check sometimes, right? It’s really quite an endeavor, especially something that is such a big-picture, strategic kind of book. So, well done.


Just a couple more questions. I wanted to ask you about the company that you co-founded called 18 Coffees, which was, I think you were in the middle of doing or had done for a little bit when we first met in Chicago. What was the original intention of 18 Coffees? And how has it evolved over time?


Caleb Gardner  22:43

Yeah. I mean, it’s funny to think about the moment that we’re in and a lot of the work we’ve been talking about in terms of the impact of, or the intersection of, social impact and business. Because our vision at the very beginning of starting 18 Coffees was that there was something really meaty and interesting at this intersection. And my business partner and I came from a digital strategy background, and I think that it really informed how we saw the impact of technology in terms of allowing people to have their voice, to be able to speak about their values, and to be able to say, “This is the kind of business I want to buy from. These are the kind of services and products that I want. I want them to reflect who I am and reflect my values, reflect my political beliefs.” Sometimes pretty explicitly.


Coming out of working for Obama and having done some of that work and having seen, you know, how terrible most companies already were at technology integration and digital strategy in terms of not being big-picture enough and imaginative enough, we were like there’s something really meaty here at the intersection of digital disruption and social disruption. Like, it’s not…there’s something coming where companies are going to need to have tools to be able to navigate that kind of big change. And I think we were, actually – it’s funny, because from a market perspective – I think we were actually a few years early, like we were kind of pointing a little bit toward it coming.


But then, of course, the pandemic hit, and the Trump administration, and all of these things, and all of a sudden it was in everyone’s faces. We’re, you know, thinking about digital disruption, because we’re literally being forced into a Zoom environment and a hybrid work environment. And, you know, technology is becoming even more integrated into our lives. We’re forced into social disruption because we’re looking at a really disruptive political environment. We’re talking about not only Donald Trump, which we’ve talked about, but George Floyd, and all of these other really disruptive moments. We’re forced to think about the future of work in ways that we realized we hadn’t really acknowledged. Like, as much as we had talked about the future of work, it wasn’t really until the pandemic that the future of work really started to arrive, because we were forced to reconcile with why did we structure work like we had structured it before? A lot of it was just, we kept doing it because that’s how you do it.


And so, there’s been so many kind of transformative things that have happened; we just…we found that our clients needed people who could think through it with the kind of experience we had, who could look at it from you know, that Obama-style community organizing background and say, “We need to have ways that we can get everyone on the same page and moving in the same direction.” And I think we’ve kind of arrived at a moment where things like ESG are starting to codify some of that thinking, but it’s still very new and it’s still, we think, a big market opportunity for us.


Looking Towards the New World of the Future

Pamela Slim  25:40

It’s one of the curses sometimes. I see that for myself having written Escape from Cubicle Nation in 2009. And then I think of, before the Great Resignation, Kelly and Jody, some friends who wrote Why Work Sucks and How to Fix It, which was basically all about a results-only work environment where people didn’t have to physically be in offices. And I don’t know if you remember that one from way back in the day, but it’s wonderful when you can have that instinct and a bit of the vision for the future. Of course, we didn’t see a whole bunch of things coming.


But that I find sometimes can just be to have that patience, of knowing when you have that instinct of what it is that you want to build. Sometimes it’s just this intuition of what the world needs. I work with a lot of people – and I include you in this designation – which I call architects of liberatory change. And for me, it’s really people who specifically want to build the infrastructure of the future that is more equitable, human, less destructive to people and the environment. Do you have a sense of the kinds of things that you want to build in the future toward this mission? 


Caleb Gardner  26:49

Yeah, I mean, I want to…so many things I want to do toward that mission. It’s hard to narrow it down. I mean, I want to first and foremost, empower individual contributors, employees, individual managers, and leaders, to be able to not only have the tools to be able to push their organizations in that direction but know how to have the kind of change leadership that can, you know, really be transformative. And that’s a lot what the book is about.


And then from our company standpoint, I think we really want to be a part of putting on paper what that next generation of business looks like. Like if the last, you know, whole business cycle of thinking in terms of frameworks and strategies and how you think about different parts of business built the kind of exploitative environment that we had before, I think we want to be a part of codifying, okay, if you want to do customer strategy, or you want to do organizational development in the new generation of business, what should that look like? Like, let’s put some thoughts down on paper and have, like, have our clients at the table with that helping us create that new, you know, kind of next-gen economy.


And then eventually, I think, either from an individual kind of investor advisor or from a company standpoint, like, look at the technology side of that, too, and say, like, how do we build systems and infrastructure from a tech standpoint that we can be proud of, that can enable and, you know, and help us create a platform for that economy in a way that’s not, you know, having people doing really great work but having to use tools themselves that are actually exploitative, or breaking democracy, or making the environment worse, you know what I mean? Like, I think a lot of us in the last few years have said, “Oh my god, we’re doing such great work with X,Y, Z tool – and Facebook. But maybe we don’t actually feel great about it.”


Additional Resources to Continue the Conversation

Pamela Slim  28:54

I love that. Well, I can’t wait to see what emerges. So, you can find your amazing book, No Point B, everywhere books are sold, in stores, and online, and so forth.


Caleb Gardner  29:06

Audiobooks, ebooks, and all those versions.


Pamela Slim  29:10

Kindle, everything you can imagine. Where can people find you and connect with you?


Caleb Gardner  29:15

Yeah, the easiest way is Or I’m pretty much at Caleb Gardner anywhere. So, you know, find me. Chat with me. I love talking about this stuff.


Pamela Slim  29:25

I appreciate you so much. Thanks for spending time with us.


Caleb Gardner  29:28

Thank you. Always great to spend time with you.

Reader Interactions

Leave a Reply

Your email address will not be published. Required fields are marked *