17. Alex Shootman, CEO of Workfront discusses the weariness of the workplace and how to survive working remotely during Covid19.




Alex Shootman shares the important lessons that cycling and the highs and lows of raising children have taught him about work.


Man clean shaved and in a suite smiling

This week we’re picking the brains of President and CEO of Workfront, Alex Shootman. Workfront is a web-based work management and project management software company that focuses on helping its customers transform their work experience.



[00:00:00] – Alex Shootman
You know, maybe the biggest benefit that’s going to come from us all going through this pandemic together is a realization that we actually like to be around other humans. Hope is being sure of something that you cannot yet fully see.

[00:00:26] – Doug Foulkes
Welcome to The Future of Work, the podcast that looks at, you guessed it, the future of work. It’s brought to you by WNDYR for their blog, Chaos and Rocket Fuel. WNDYR are productivity and human behavior specialists who use technology to help us humans on our digital journey from disruption to transformation. I’m Doug Foulkes, and along with WNDYR CEO Claire Haidar, we regularly meet up with industry experts and mavericks to get their take on work in the future. This week, we’re picking the brains of president and CEO of Workfront, Alex Shootman.

Workfront is a web based work management and project management software company that focuses on helping its customers transform their work experience. Alex himself has over 25 years experience developing and leading tech and noticeably SaaS companies (that’s software as a service). He is also an author and as well a keen cyclist and dedicated family man.

[00:01:29] – Claire Haidar
I’m curious. I’m jumping right into the piece that interests me most. What sport is occupying your time at the moment and what lessons are you learning from it?

[00:01:39] – Alex Shootman
Well, the sport that occupies my time right now is road biking. I moved a few years ago from running to road biking. And, you know, the thing about road biking that I’ve learned is the most fun part about road biking is flying downhill, and especially if you get to fly downhill with lots of S-turns. But to really go downhill, you have to go uphill and I think would have been taken away from road biking is in the toughest moments, when you’re climbing your hardest hills, the hills that have been the boogeyman in your head for years, what you can tell yourself is if I get to the top of this, I’m really going to enjoy the downhill. And so that’s what I take away from road biking, is when when things are really tough, you can say to yourself, look, when I get through this, I’m going to really enjoy the other side.

[00:02:44] – Claire Haidar
I’m going to move to a very, very personal side of your life. Alex, about Tara and Remi, they’re a significant part of your journey. How has adoptive parenting shaped your view of work?

[00:02:59] – Alex Shootman
You know, prior to adopting our two daughters, we had and we have two biological sons. And we when we adopted our daughters, our sons were 15 years old and 12 years old, and the girls were eight and five years old. And, I had a boss once tell me you can’t learn to swim in the front yard. And, you know, we’ve been through all the classes. We’ve been book educated and we thought we knew what we were doing. And then all of a sudden, you’re trying to essentially stitch two families together and everybody’s their own person. Right. And so your biological kids may not have the same level of enthusiasm in the moment. Your adoptive kids, they didn’t really have a choice in the matter. They got adopted. But what I learned is that in all of our lives, every single year, we have joy and we have pain. The first few years of putting our family together, the joy was, was “joyier”, if that’s a word. And the pain was “painier”. But but it was still the same cycle that we all go through that in our life we have joy and in our life we have pain.

And what I learned is that those really significant moments of pain when we put the family together also came with very, very special moments of joy. You know, when you have a biological child, your child attaches to you before they’re really a sentient being. They attach to you when they’re an infant. And so a particular moment of joy for me was experiencing my younger daughter attached to me as a sentient being. She was she now has no accent, but she would sit in my lap and I was reading a magazine and she looked up at me and said, “I love you, Dod.” She used to call me “dod”. She said, “I love you, Dod.” And, you know, we would say I love you. But they didn’t come speaking English. And so it was it could be a form of a greeting for all I knew. And I kind of looked and said, “I love you too” to her. And then she looked up at me again and she said, no, “I love you” like she had just had this feeling of human attachment that once again we experienced with our biological children, but we don’t see them experience it.

And so you would get these very amazing moments of intense joy like that, but also intense pain. And so really what it’s taught me, Claire, is that that’s just part of life. A part of life is, during the year, we’re going to have some pain. We’re also going to have a lot of joy in what we know is that there’s joy on the other side of pain and that can give us the endurance to go through the tough moments.

[00:06:36] – Doug Foulkes
Alex, I’m going to add my welcome. Nice to chat to you today. And you spoke about joy there. Something else that you talk and you write a lot about his pride, maybe because of the multiple experiences that you’ve had with various people along the way. Do you still believe that modern work has to embody pride as an essential part of the experience?

[00:06:58] – Alex Shootman
Doug, I do. I think that human dignity is fulfilled by working. I think that work is good. When any of us look down at something that we’ve created, that we’ve created with our own hands, created with our mind and see that it’s good, it’s just it’s hard to avoid feeling proud of that and not the bad kind of pride. You know, the pride goeth before the fall kind of pride, but just the the very good feeling about yourself when you’ve done good work.

And so because of that, what I’ve long believed is if we can just barely accomplish three things in an organization, we’ll release people. The first is, do people understand what their role is? The second is, do they do they believe that their role matters? Do they believe that the role is connected to something? And then finally, do they have the opportunity to be proud of their work? I saw it just last night with my youngest daughter doing homework. She was struggling with algebra. We worked through a problem. She did the second problem all by herself. And then she checked the answer in the back of the book and she saw that it was right and it was impossible to take the smile off of her face. It’s just, in a moment like that, when you watch a human, it is impossible to remove the smile from their face. And so I just think that’s our obligation at work, is to figure out how we can help people feel proud of their work.

[00:08:35] – Claire Haidar
When I read your thoughts about pride and when I actually went back into the archives of your blog and saw how often you spoke about it, it connected the dots in my millennial brain in that we actually need to remove all of that fluff and that extra that we’ve brought into the world of work today, and we just need to go back to the basics of that very, very simple component, just work no matter what work it is. If I am doing good work, there’s an element that fulfills my human dignity. And I think we we’ve lost sight of that and we need to come back to it.

[00:09:16] – Alex Shootman
What’s interesting is we did a study with the Center for Generational Kinetics, Jason Dorseys, the CEO of that organization. And we were studying generations in the workplace. And I’m happy to share all of the detail with you on that. Claire, there were a couple of myth busting moments for us. One of the questions that we asked is what is the most appealing work culture value? So we expected, based upon the histrionics that are in the press, we expected that it would all be about purpose and personal enjoyment and social responsibility. But it turns out, by far, the most important work culture value was caring. Does an organization have values that promote positive working relationships, collaboration, teamwork, and loyalty? Twenty-five percent of millennials said that that was most important. The second biggest was learning, which is seventeen percent of millennials. The third was purpose, which was fifteen percent. So that was one of these myth busting questions.

And what I’m saying is I personally think that most of what we read in the press is just flat wrong. I see so much more commonality across generations in terms of people wanting to do great work, people wanting to have a purpose in their work, people wanting to have collaboration and teamwork and build things with other people. I think that’s timeless.

[00:11:01] – Claire Haidar
In many ways, the current environment that we find ourselves in this pandemic-era has so significantly brought both of our collective visions to life. I want to move a little bit away from the excitement of that and the fact that the future of work is now our new reality. And I want to talk to you and ask you whether you are also sensing the deep weariness that a lot of people are feeling right now.

[00:11:27] – Alex Shootman
I do see that. And I think there are two causes to that, Claire. One is human and one is technology. On the human side, maybe the biggest benefit that’s going to come from us all going through this pandemic together is a realization that we actually like to be around other humans, you know? And so whenever you see weariness that I think that comes from a lack of joy. And I do think that working day in and day out without having the opportunity to be around other people in three dimensions, just robs a sense of joy, and that contributes to some weariness.

In addition to that, though, clear, what I’m seeing happen is that people are trying to use the wrong tools to do the wrong things. And just like if you try to cut down a tree with a hammer, it’s just going to make you really tired. If you think about when the pandemic first hit, everybody bought what I would call their crisis tech stack. They bought at Slack and Zoom or they activated Teams if they had Teams inside of their Microsoft license agreement. And those are all fantastic technologies we use Slack internally, fantastic technologies. But they’re made for synchronous work. They’re made for what you and I are doing right now where we’re interacting with each other. They are not made for asynchronous work. And so when we fill our days with trying to do work that’s better done with technologies that help do asynchronous work, like a work management platform—when we fill our days trying to do that work with platforms that are built for synchronous work, it’s like trying to cut down a tree with a hammer and it just makes us tired. And I think that’s one of the things that is creating weariness is picking the wrong tool for the job

[00:13:34] – Doug Foulkes
I’m going to jump in. Alex, I’m going to just keep it on the global pandemic, if you don’t mind. I know at Workfront you’ve got a very strong leadership team. Can you sort of share with us if you use a specific framework or model to help guide your team members through this whole situation we find ourselves in?

[00:13:51] – Alex Shootman
Doug, I don’t know if it’s a framework, but it’s a couple of words. Napoleon once said that a leader is a dealer in hope, and if you think about what hope is, a hope is being sure of something that you cannot yet fully see. The first part of the framework that we’ve used is, is to just focus on that. Look, we need to be dealers in hope. That’s not false hope, so that’s not saying we’re not in a difficult situation. That’s not saying the world is not in a difficult situation. It’s not being Pollyanna, if you will. But it is very consciously speaking to the things that we can control and speaking to the good outcomes that we believe are going to happen because of the people that we are, the culture that we have, the company that we have, the customers that we have. The second is transparency. We’ve just been really up front the whole way about the company, what’s working within the company, the financials of the company. And so really, our framework has been those two words, if you will, Doug. The words, how do we speak to an authentic hope and then how do we make sure that we are transparent about what’s going on?

[00:15:20] – Claire Haidar
Alex, on that note, I’d like to take the conversation from the specific, to that is, has your typical work day changed because of this framework that you guys have instituted and because of the need for full hope has has become so critical in this period?

[00:15:40] – Alex Shootman
Claire, I spend a lot of time with other CEOs and we compare notes about what’s going on. My workdays, changed—maybe not specific “day”, but my work has changed a couple of ways. You know, if you think about the Monday after George Floyd was killed was measurably—I forget the name of the organization, but they measure emotions on Twitter and that Monday was the saddest day in the history of Twitter.

What what several of my peers and I have had conversations around is, at least in the states, in any case, many of the institutions that people turn to in moments like George Floyd getting killed, Breonna Taylor getting killed, Ahmaud Arbery getting killed—in moments like that, people had institutions in their lives to go to to have conversations about that, to sort out their own feelings, to understand what can be done, some of those institutions have maybe faded in terms of importance in the communal life, at least within the states. And in a lot of cases, our companies are not feeling all of that because we can’t, but our companies are filling some of that. And so we have a responsibility, if we’ve been blessed to be asked to be in a leadership position, we have the responsibility to step up in those moments and try to build somewhat of a community that can process these, you know, incredible, sad moments for all of us.

[00:17:46] – Claire Haidar
That segway so well, because what you’ve just said in terms of creating those spaces where teams can mourn, process, talk about, etc., it’s a type of transparency. And this is something that’s critical to the book that you wrote about two years ago. You talk about five types of transparency and how those interplay to create meaningful work. I personally feel that transparency is a very misunderstood concept and therefore not harnessed the way it could potentially be. So can you maybe take us right back to definitions and talk to us about what your definition of transparency is, but then also lay out for us what these five types of transparency are and why they are so important in creating meaningful work.

[00:18:36] – Alex Shootman
Maybe the easiest way I can define it is for anybody that has seen the movie A Few Good Men. There is the climactic scene in the courthouse between Tom Cruise’s character and Jack Nicholson’s character. Jack Nicholson plays Colonel Jessup. And in the moment, he basically says “You can’t handle the truth.” And so there can be a fundamental bias that you start to have as a leader, where you start saying to yourself, I really can’t tell them the truth. I need to shape the truth for them. And that’s actually a pretty demeaning attitude, if you think about it. That’s basically saying that I’m smarter than you. I’m better than you. And so I’m going to have to give you less information because you can’t deal with all the information. And what I found is the opposite is true, Claire, that secret strategies don’t work really well and people can handle the truth. People can handle what’s going on in a business. And frankly, there’s more ownership about the mission. There’s more ownership about the business objectives, there’s more ownership about the task. There’s more ownership in the work. If you share with people why you’re trying to accomplish something, what it means to the organization, what it means to them, how they plug into it. And that notion of transparency drives our technology investment.

We just released a product called Workfront Align, which is a product that allows for goal visibility and goal transparency and goal cascading throughout the organization. And I’ve had customers and prospects asked me, so you actually open up your goals to the whole company? Like, absolutely. It’s their company too, they should see what’s going on. So for me, it comes back to that Colonel Jessep statement. And when you listen to Colonel Jessup, do you agree with him or do you not agree with him? And whatever side you fall on drives how you think about transparency.

[00:21:10] – Doug Foulkes
How does that—relate that into a typical day for you? Alex, what’s your day look like when you’re being transparent and leading?

[00:21:19] – Alex Shootman
I’m spending more time now than I used to in purposeful, more broadcast communications. For example, we have three strategic pillars for our company. The first is to serve the enterprise. The second is to build a enterprise application platform that we call an operational system of record. And the third is to multiply advocates. And I’m right now, I’m shooting a video series that’s, you know, three to five minute videos on each one of these strategic pillars kind of going back to what does it really mean to serve the enterprise?

And I think in the past I would have done a lot of that in various town hall meetings, or one- on-ones, or when I’m walking the hall and stuff like that. And so what I’m finding, Doug, is that there’s more of my day that is spent trying to keep us as a team together on what we’re trying to accomplish using various communication tools. What I’m doing less of, which I miss, is getting on an airplane and going and seeing customers. So, I’m seeing customers on Zoom calls. But there is something different about being able to be with customer in their location. There’s a level of intimacy where you get to learn more about their organizational dynamics, what they’re trying to accomplish, what’s getting in the way. And so I miss that. I look forward to that coming back because there’s a texture to customer intimacy that I’m personally missing right now with this work environment.

[00:23:02] – Doug Foulkes
That is interesting because it sort of leads a little bit, could be the answer to my next question, because work has changed considerably for just about everyone the last few months. If you had a magic wand, what would you change again in a fundamental way moving forward? And is it going to visit more clients or customers?

Well, certainly, I would do that. I’ve been thinking about buying an airplane seat and just putting it in a room in my house because I used to be able to do some good thinking in an airplane seat. I tell you if I could wave a magic wand, what I would want to get rid of is conspiracy theories at work. I talk about this in the book that we wrote in terms of the transitive law of conspiracy theories, which goes as follows: all management activity in a company is mysterious and all mysterious activity in a company creates conspiracy theories. Therefore, all management activity creates conspiracy theories. And it’s just most of the stuff that people make up that happens in a company, or they make up, that is happening in the company is actually not even happening at all.

[00:24:18] – Claire Haidar
So we’re doing something very interesting in WNDYR. We’re actually rolling out—I’m not sure if you’ve read this book—Lencioni’s The Advantage?

[00:24:27] – Alex Shootman
Ironically, I’m talking to Pat later today. So we’ve we’ve actually had a long relationship with the table group. They helped us do our work around culture. So, I know the advantage very well. And if you actually look down, Claire, interesting that you say that, because if you looked at the book that we handed out to our employees at the beginning of the year, you’d see if these words sound familiar to you. So the book walks through and it says, “Why do we exist?” Then the next question says, “How do we behave?” Then the next question says, “What do we actually do for a living?” Then the next question asks, “How are we going to succeed?” And those are the three strategic pillars that I just shared. And then we talk through our defining objectives. So we actually used the advantage methodology in building our business plan.

[00:25:31] – Claire Haidar
So those six questions that Pat lays out in his book, we actually have it in a one pager. And it’s part of our company onboarding. It’s part of everything that we do in the company. But what I wanted to share about what we were doing is, we’ve actually tiered our entire team because the book has had such a big impact in our company that we’ve now adopted the attitude of every single person in the company needs to be a leader. And so we’re actually rolling it out across the entire company.

[00:26:02] – Claire Haidar
I’m hoping in our case that this experiment that we’re running, where we’re developing this radical transparency around even opening up like the financial model and how it’s built, we’ll enable our team to understand grey and therefore minimize those conspiracy theories that do come up in companies.

[00:26:23] – Alex Shootman
I think that’s fantastic that you are doing that, and I predict it’s going to be a huge lift in performance for the organization. And that gets back to the Colonel Jessup statement. Right. You’re basically saying, “I think people are smart enough to figure this out.” And if they all understand it, they’re going to make better decisions.

[00:26:42] – Doug Foulkes
Talking about your book again, you reference the military term “embrace the suck.” Do we as a modern workforce do this enough, in your opinion?

[00:26:5] – Alex Shootman
I don’t think so. I really don’t. I got the notion of “embrace the suck” from talking to Mark McGinnis, who is a retired SEAL commander. And what he was sharing with me is, you know, if there’s a team and they’re neck deep in muck crossing a body of water. And if one person starts talking about how this really sucks, it starts to get infectious with everybody else. But if instead the entire team just embraces that it sucks and that they have to go through it, then the team will get through that moment in a much healthier manner. And, you know, we complain about the tools that we’re using or we’ll complain about a lack of information or we’ll complain that somebody didn’t update us on something. And so, you know, we’re offended by that. If you think about the the things that send people sideways in most most white collar work, they’re massive first world problems. And instead of us just letting it run off our back, like water off a duck’s back and moving on to more important things, we just get completely wrapped around the axle on it. So I don’t think that we do embrace the suck that well, Doug, in modern work. I think we let little things knock us off our game quite a bit.

I have noticed, however, that one of the odd blessings about us all going through this pandemic is things that used to bug people, little things that used to bug people, aren’t bugging them that much anymore because they’ve gone through some big things.

[00:28:51] – Claire Haidar
Moving onto you again, Alex. What new skills are you working on and learning at present?

[00:29:00] – Alex Shootman
For me, it is in using the different communication mediums to match the needs of folks in the organization. I’ll give you an example. We’ve got a project going on internally where we’re completely reimagining how to do sales and marketing. How do we create this amazing buying experience that’s such a great buying experience that people just tell other people about the buying experience? And we’ve put together a cross-functional team that are focused on that. And I’m watching generational differences in terms of media consumption, where in some meetings the team will go ahead and record the meeting for their other team members. And those team members may watch that video at 2x speed. If you look at my generation, we would have never considered that the way that we were going to consume information is to take a video and watch it at 2x speed. And that’s how we were going to get the information imparted into our brain.

What I’m learning a lot right now is how do I learn these different communication mediums? If it’s my responsibility to meet somebody in the organization where they are, that means I need to understand their communication preferences and I need to deliver information in their communication preferences. So that’s probably one of the biggest things for me is learning different communication channels and how to take advantage of them.

[00:30:38] – Claire Haidar
Alex, I could honestly carry on talking to you for a very long time and I will say in many ways, I wish I could be a fly on the wall in your conversation with Pat today. But, in closing, I really do want to have a conversation about Workfront specifically. It’s all about modern work management. This is an area that both you and I are very passionate about. Can you, to wrap this podcast up for us, define what modern work is and why it’s so important to understand that it is significantly different from work as we knew it in the past?

[00:31:14] – Alex Shootman
You know, if you if you think about it, the question is, why is work so hard right now? What challenges productivity right now? And you have to start by thinking about the five elements that have always been in work, right? The first is there is somebody who has to do the work. The second is the work has some time boundaries to it. The third is the work has some location boundaries. The fourth is that you have some tools that you need to accomplish the work. And then the fifth is what is the level of interdependence? And so if you put all that together and you go back hundreds of thousands of years or millions of years to our earliest ancestors, and you think about the work at that point in time of somebody hunting. That work was it was clear who the worker was and it was clear what their job was. The time was very specific in terms of when you could do the work. There was only one location to do the work. There was one tool to do the work. And the interdependence was pretty low. I mean, maybe there were parts of the tribe that was fleshing out the game and there was parts of the tribe that was hunting the game. But the interdependence was pretty low. Now, when you think about all what’s making work hard right now is all five of those things are changing all at once.

Time: it’s not nine to five work. It’s it’s not even just-in-time work. It’s all the time. The location, the work can be done anywhere. The tools are infinite and they’re changing every single minute. And when you think about interdependence, there’s very little work that one person can complete all of the work. So modern work was hard already because all five of these things were changing all at once. And then the pandemic, we just poured gasoline on the fire and made it even harder.

So that’s really what’s happening, Claire, is the five elements of work have never changed. When any single one of them changed, it made work hard. And now all five of them are changing all at once. And that’s why it’s hard to manage modern work. It’s the old acronym that came from Warren Bennis. When we talk about what is a VUCA world: volatility, uncertainty, complexity, and ambiguity. And that’s what we’re leading through right now.

[00:34:17] – Claire Haidar
Yeah, exactly that. Alex, this has been an amazing conversation. Thank you to both you and Doug for joining us today. And I really am sure I mean, just from the conversation, there’s so many more follow up conversations that we can have. So thank you for taking the time. Thank you for sharing your profound wisdom with us. And thank you for the impact that you’re making in the world right now. It’s important. And we need leaders like you.

[00:34:44] – Alex Shootman
Claire, thanks for the opportunity and thanks for what you all do at WNDYR. We get a lot of joy working with y’all and your level of thought leadership and capability makes a huge difference to our customers. So I’m very appreciative that y’all decided to be business partners with Workfront.

[00:35:05] – Claire Haidar
Thank you so much.

[00:35:07] – Doug Foulkes
Thank you, Alex from my side. It’s been great meeting and chatting with you.

[00:35:11] – Alex Shootman
All right. Great to meet you too, Doug.

[00:35:13] – Doug Foulkes
And there you have it, a real hands on look at what modern work is all about today. If you’ve enjoyed this podcast and found it of value, please don’t be a stranger. Make sure you pop back for more top of mind conversations. Just a reminder, for more information about WNDYR and the integration services that they supply, you can visit their website at WNDYR.com. And so from me, Doug Foulkes, and from Chaos and Rocket Fuel, stay safe and we’ll see you soon.


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