Done Right Podcast
Episode 10

Leading with Purpose with Mike Kilbane

 

Welcome to the Done Right podcast. I'm Jordan Staples and over the past decade and a half, I've been studying how people live successful and satisfying lives, both in and outside of work. And here's what I've learned. People in the workforce who are successful and satisfied are the ones that show up, pitch in, and make an impact in their companies. They are the ones who know how to get stuff done but do it right. So our mission for this podcast is to deliver insight and inspiration to fuel the way you show up at work today. 

[Jordan] Mike Kilbane, we're glad to have you on the podcast. 

[Mike] Jordan Staples, I couldn't be happier to be on the podcast. 

[Jordan] Glad we're making this happen, my friend. Before we dive in, why don’t you give us a little bit of your background to give us some context for your experience. 

[Mike] Yeah. I grew up most of my life in Southern California and had three brothers and was raised by a very disciplined Irish Catholic mother. So following high school, I went to West Point, and I like to comment that I was actually getting a break at West Point from living with my mom. So I enjoyed a lot of structure and discipline through most of my life. When I graduated West Point, I went on to be an officer in the aviation branch of the army and flew helicopters with the army for seven years, spent time in Korea, in Texas, Alabama, and then ended my career in a special operations unit at Fort Campbell, Kentucky. 

Following that, I did a lot of consulting. I spent time with KPMG, with IBM and then had my own consulting business on a couple of different occasions. I spent about seven years at Western Union in a variety of strategy roles. I also served as the chief of staff to the CEO Western Union, as well as the COO and head of strategy at their national payments business. Prior to taking this role at Workfront, I had my own consulting business and in that role, I was doing some consulting with the executive team here at Workfront as well as with other clients in the financial services industry and the energy business. 

[Jordan] So, you've got a pretty unique role, I'd say, at Workfront, and we have a chance to work together. But why don’t you tell us a little about your role as the guy who's here at this company to help us get it done and do it right. 

[Mike] Right now, I'm really excited to be here. I was brought on as the senior director of Modern Work Management, which includes the initiative currently known as Workfront at Workfront. So it is about getting it done and doing it right and encompasses, how we use our own platform, how the employees get stuff done here and hopefully taking those lessons learned and best practices we discover and create, and sharing them, you know, with customers and potential customers. So really excited to be here, excited to be part of a great culture and certainly not starting from scratch. It's building on the great work that's been done over the past 10 plus years here in terms of, you know, the software and the platform that's been built, but also walking into a great culture of enthusiastic people who are eager to get stuff done. And hopefully, by applying the principles from the book as well as some other best practices, we're gonna help people do it even better. 

What does it mean to lead?

[Jordan] Cool, that's awesome. All right, so my first question for you is around leadership. We had a bit of a conversation yesterday around leadership. Mike, tell me, who in your career has been kind of that standout or that leader that has taught you about what it means to lead? 

[Mike] Yeah, I think, you know, the best leaders I've had and I've been fortunate to have some great ones. They were always the leaders that put you out just far enough over your skis that you were forced to grow and stretch. They didn't ask you to just continue to do what was easy to you. They put you in positions or situations that required you to stretch and, you know, as a result, took risks that may not have ended up completely successful, but would learn from it. And I think they were wise enough leaders to recognize they were putting you in that position and gave you the opportunity to succeed or fail on your own merits. But then, you know, not look at a situation where they put you in something that would be a career-ending or career-threatening move. It was really a deliberate opportunity for you to grow. 

So there was a great battalion commander when I was in the army who allowed me to do some really creative things, both in terms of missions and exercises. You know, that was well beyond my role and gave me the chance to be really creative. He wouldn't really define things specifically about how he wanted to get done. He really just explained what needed to get done. Commander's intent from the book. Then gave me the creativity, authority and freedom to go get it done, so as a result, I got to really understand how to leverage networks and connections and resources and really use my strengths and, you know, things that I was good at to make something happen in the way that I saw. 

[Jordan] I don't think I usually put the words creativity and the military together. 

[Mike] Yeah. It’s interesting.

Creativity in leadership:

[Jordan] Tell me when you felt like you were able to be creative. What did that look like specifically? Maybe there are missions you can speak to. 

[Mike] So creativity I think is involved. You know, creativity in the business sense often, you know, would involve marketing departments or agencies or things like that. And that's typically where we go in terms of creativity or with a product. But, you know, especially as it applies to work and getting things done is there can be creativity in process and creativity in resources. If you have limited resources, you have to be creative about how you use people, how you connect with people. You don't always have all of the resources at hand. So maybe you rely on favors for people. Maybe you have to be persuasive in how you get people to do things because you can't just pay them or they don't just work for you. 

So in terms of creativity and processes, if you have a mission to get done, it may be pulling somebody, in this case in the military, who's in a role that, you know, this may not be in their job description but by their personality and their attitude, they're interested in trying to do new things. So you pull them into the mission or into the operation and say, hey, I know you're not typically a driver who goes out and sets up communication retransmission sites. But you're a good guy. You're eager to do things. So come and join me and we're gonna go drive out to the middle of the desert and set this thing up, not in their job description at all, but it's creative. So you go to your network, find people who, you know, who are eager to do the job and you pull them in to do things. So in terms of the military, a lot of creativity involves sort of improvising when things don't go right. 

Going back to the book, and I think I've jumped ahead here a little bit. That's really what the commander's intent allows you to do, is it encourages and allows creativity in subordinates and subordinate leaders to go accomplish the mission or get the job done when things don't happen as expected. So you tap into your people's strengths, you tap into just kind of their initiative and they know what the end result needs to look like, even if now they have to go by a different route because, you know, a bridge is blown up or, you know, any of those kinds of things, they still know where they need to go. They don't, you know, have to say, hey, the bridge was blown up. You told me I had to drive on this road. And so, you know, now things don't get done. They go and they find a different way around it. So the creativity really comes in the how and, you know, the resource employment and how you pull those kinds of people in. So I think that's where creativity comes in. And that can all apply to, you know, business as well. You don't always have the resources or people on your team rather than throw up your hands, you just you kind of go beg, borrow and, you know, convince people to help you out and you get it done. 

Building influence and persuasion:

[Jordan] So one thing I’m hearing from you is influence and persuasion. So I think a lot of people probably have had an assumption that people are born persuasive, maybe born more influential just by personality, they're more charismatic, more likable or something like that. Is that something you buy into? And if not, are there ways you've seen people build influence with others? 

[Mike] Yes, I think influence. You know, the folks you talked about with tons of charisma, you know, guys who will jump up on stage and, you know, kind of be a rabble-rouser to get people up. I think that works once for people. You know, if they are willing to sign up and follow somebody because they get them all amped up, excited, and enthusiastic, but then it doesn't pan out. You know, you kind of have one shot to do it. The better way that I have seen and experienced in terms of influence and persuasion is really by character and competence. You know, I think Covey talks about in one of his books that those are really two of the key elements in both leadership and, you know, getting things done. When people look to a leader, they want to say, are they competent? Do they know what they're talking about? Are they, you know, skilled in their job, are they somebody I can trust and believe in? And then character is, what is the integrity of this individual? Do I believe that they're going to do what they say and follow through? So, competence and character. I think two key things. You know, the charisma can be nice, and I think that kind of is sort of the cherry on the top. But I've seen great leaders who don't have that kind of a wow factor, but people will follow them wherever just because, you know, they're rock solid in terms of competence and character. 

Defining leadership through development and outcomes:

[Jordan] That's great. One of the books I'm reading right now is Dare to Lead by Brene Brown. Are you familiar with Brene and her work? 

[Mike] Yeah.

[Jordan] So she talks about and she defines leadership, and she says, “leadership is not about titles, and status, and wielding power. A leader is anyone who takes responsibility for recognizing the potential in people and ideas.” And she gives another definition where she says “people and process”, and “has the courage to develop that potential.” From your experience, is that how you would define leadership or how you think about leadership? 

[Mike] Yeah, I think, you know, and Brene Brown is great, especially when it comes to kind of authenticity, vulnerability and really connecting with people. And I think her comments on leadership are really important just in terms of the developmental aspect about what great leaders or great coaches do. The part that I would add to her definition is really about getting things done. You know, a leader who can develop their people and inspire them and all of that is awesome. And a coach would be awesome. But if they go 0 and 16, they're not a great coach, you know? So I think the leadership element that I would add to Brene’s is not just you have to be able to develop your people, but you also have to achieve outcomes. So I think those are both parts of the equation. And it's why I think here at Workfront, the idea of getting it done and doing it right is so important. 

What Brene Brown is talking about is the “doing it right” part, which is, hey, there's a culture here. We believe in people's potential. We want to see them enjoy their work, do their best work and all of those things. But the “getting it done” is we still have outcomes that we need to achieve. Just because, you know, we're a business, we're expected to generate profit for our investors. We're supposed to deliver a great product for our customers and have a fantastic place for our employees to come to work. So, you know, I think there are two elements to it. She talks about, you know, a really important part of the development. And I think that separates a leader from a manager. But the part that I would add on to hers is really about delivering the results as well. 

How to be a leader without a title:

[Jordan] That makes a lot of sense. I think a lot of people––like she mentions in that definition––believe that you have to have a title, like you have to be a people manager to be a leader. And you and I talked about how that's really not the case. So maybe what you can share is, Mike, you've had the opportunity to look at work and getting stuff done and doing it right in a lot of different contexts, from military to consulting, and now even here Workfront. From your perspective, those that don't have the titles, how can they be a leader in that sense, know where they are getting it done and doing it right? 

[Mike] Yeah, great point. I think there are so many elements of leadership that are independent of title. And if you are in a leadership role, there are certain things that you should be doing. But you can also do them as we talked about when you're not a leader. One of them is really about accountability and taking responsibility for your actions. You know, a leader doesn't blame failures on his team or her team, they take responsibility for their team's performance. And we can do that as individuals even when we're not in a leadership role. You know, if you mess something up, you step up and kind of take accountability for it. You know, own the mistake and you take steps to fix it. You know, and I think that's a key part of it. 

We also, I think, talked about yesterday, leadership is about taking initiative and not just sitting around. If you see something that needs to be changed, improved, or just done. A leader will do that whether or not that's kind of in their job description or role. Now, that's not kind of stepping out of your swim lane and stepping on other people's toes. But if there's something that, you know, has just been kind of sitting around being broken, a leader doesn't just say, “well, this sucks”. Somebody should do something about that. A leader would say, “that's not really right. I think we can do that better. Let me go explore ways that I can do it,” you know, within the context of their environment, whether it's making a suggestion to somebody, whether it's volunteering to help somebody with it, but I think leadership, again, is very independent of title and it's more about behavior. And that's, you know, accountability and taking the initiative and those kinds of things. 

[Jordan] So to sum it up, talking about leadership here. What is the skill that a leader needs to have? Number one skill. 

[Mike] I had reviewed it based on our discussion yesterday, but, you know, West Point graduating from there, you're just surrounded by and sort of immersed in a leadership culture for four years. And it's so prevalent, I think, in the military, you're exposed to leaders both good and bad everywhere you go. And West Point, a long time ago, came up with about eleven principles of leadership and they kind of list out what leaders should do. And I think the first one is really telling, and it's about “know yourself and seek self-improvement”. So a key part of being a leader is really that self-awareness and knowing these are the things I'm good at and these are the things that I can do. And conversely, these are the things that I'm weak at or need help at, and I am aware enough to go ask for help in that. Or I know that this is a blind spot and I know that I need input or perspective from somebody. So it's really, I think, having the courage to take a hard look at yourself, what your strengths are, what your weaknesses are, and really be ok with that, and then go for it. And I think that principle, even with, you know, other things I've read from Brene Brown that you mentioned, that's a key part of her message as well, is, you know, there's certain things either that you've done or experienced or been a part of in your life that you just have to own and I think being willing to own those things––good or bad––really makes you a more whole person. And I think that's really what people are looking for in a leader is are they authentic? Do they know themselves and, you know, those kinds of things. So I think what I would say is the number one thing to lead, whether it's in a formal way or an informal way, is really understand who you are and then find ways to be better. 

Defining moments that bring out leadership:

[Jordan] So can I ask you in your personal experience, what maybe a formative or defining moment was, where it was that kind of awakening or aha from a self-awareness standpoint? 

[Mike] Yeah, and I remember distinctly, I was over in Korea early in my Army career. There was another officer over there. She was in the unit and we had gotten to be good friends. And, you know, I really enjoyed joking around. I had always been part of sports teams, and, you know, there was always kind of the locker room ribbing and, you know, all of that. And I could get pretty harsh with a lot of it. And I just continued that, you know, early on in my career. And it was just sort of what I was always used to. And I remember we came out of a meeting one time and she made a comment to me and she said, “you know, you'd be a lot more effective if you didn't make the people around you feel crappy all the time.” And, you know, she said it in such a way that it was kind of joking, kind of not. But it really hit home that, you know, in some environments it's great to be the funniest guy at the table. But when you're a leader, you know, people aren't paying you for your sense of humor, you know? So probably one of the formative things for me was to bite my tongue sometimes and resist the easy joke or the quick crack to make people laugh, and just kind of step back and try to think about how it's going to land on people. So that was something that has stuck with me. It doesn't always stick with me. There's times that I'll slip and, you know, make comments about you or make comments about other people. 

And I've done that differently throughout my career, but, you know, one of the big formative things is recognizing that. And I think, you know, back to leadership, I think the further you progressed up in an organization, what you have to realize is, you know, for me, I was no longer Mike to people. I was actually a title. So when you come into an organization and when I was the chief of staff, at Western Union and, you know, we'd go into, you know, another country and I'd walk into the office and there's the whole country team. They didn't see me as Mike. They saw me as the chief of staff. So anything I said that could be a sarcastic comment about, “hey, you guys didn't make your number last quarter” or “hey, you guys were a little slow on this”. They don't take that as me being sarcastic, they take it as a really sharp stab from somebody who's in a position of authority. So being aware of when you're being your person or when you're being a position is really important. 

So I think combined with, you know, kind of the lesson I learned early on about, you know, be careful of what you say. Also with, you know, the amplification effect that takes place when you're in a position or role of authority are things that I really continue to have to remind myself; there a lot of times that I want to make a quick sarcastic comment, but hold back because, you know, realizing it will have an outsized impact over what I want to make. 

Being a leader with a title:

[Jordan] Yeah, so I want to talk about that for a minute, because I think we were talking about, ok, you don't need a title, you don't need authority to be a leader. We talked about some of the traits there. Let's talk about the other side of that. When you are in a leadership position––because I felt this as well––especially when I stepped into my role today as a director, you are a title. You are in that role, especially when you have a certain number of direct reports, or you have certain peers you're working with. What have been the lessons learned? And maybe just to keep extrapolating on this, what are some lessons on when you are in that position of authority, if you will, what does good leadership look like? 

[Mike] Yeah, I think the number one habit is listening to people. That's the number one thing that I've recognized because you have been... and sometimes it's harder when you're promoted from within an organization because people who on Friday were your peers, and now on Monday, they report to you. It creates a dynamic that will be challenging for both people. But I think listening and really giving people equal voices and things, even if they don't have the same vote, is important, you know, because what I think you have to show to people is just really respect for them as people and their opinions. You don't have to necessarily follow it, but letting people know that they're heard, that whether they're a an associate, whether they're a manager, whether they're a director or whether they're a V.P., you know, they all have opinions, they all have feelings. They all have their perspectives, and they're important to hear and they're all valid. You know, what you do with them is your decision as a leader. But what you should always be willing to do is certainly listen to them. 

[Jordan] So there's this really great concept that Alex Shootman brings up in his book, Done Right. And it's this idea of making work matter. And he gives a couple of tactics on how to do that. One being, having a vision and being clear about that vision and really giving people a “why” to their work. There are a few questions that he says like your people will know that their work matters when they understand their role, they believe that it matters and that they've had a chance to be proud of their work. So my question is, this idea of making work matter, and I know that we're both kind of biased because we both work for the guy that wrote the book, we know him well, but the concept of making work matter and I'm just feeding off of this idea of really listening... How has that concept played out in your career?

[Mike] I think, you know, whether I felt listened to, you know, the decision may have gone another way, but it's, you know, it's reaffirming as a person that you matter to the organization. I think when you feel listened to and really heard, and then if the leader has the courage to talk to you about, you know, “I made this decision, it's not what you recommended, and here's why…” And at least you're given the opportunity to hear the explanation about why you went the other way; it becomes something that you can support. I think leaders can go ahead and dictate a decision, and as long as is they explain, “here's why we're doing it,” and it might be something as simple as, you know, “my gut instinct and experience tells me that in spite of maybe your recommendations or your perspectives, I'm going a different direction.” I think people will respect that a lot more than somebody who makes an edict type of decision and never wants to hear from anybody that they're threatened about being challenged. When you have a leader who doesn't want to at least be able to answer a question about why something was done or not, what it comes across as, is a lack of security. And I think people are hesitant to follow insecure leaders. You know, for a number of reasons. Now, that doesn't go to say, you know, in a lot of situations that leaders sometimes have to say, “you know, guys, the time for debate and discussion is behind us,” you know, and when we say “done right”, a phrase we used to use in the military a lot was, you know, “the good idea cut off point has passed us.” You know, at some point you just have to move on and say the decision has been made, we're going to execute it. Otherwise, organizations or teams get paralyzed because they think, you know, every week we can revisit a decision and say, well, let's look at it again, and let's look at it again, and then the organization doesn't go anywhere. So I think, you know, as a leader, you have to be clear that we're in the discussion point and then, you know, you kind of draw the line and say, ok, guys, the good idea time is behind us, now we're in execute mode. So that doesn't mean you don't listen still to, you know, maybe comments or input. But, you know, you have to make it clear to your team that we've made the decision, now we're moving forward with this. 

[Jordan] The next step in the process. 

[Mike] Exactly. 

Providing role clarity for your team:

[Jordan] So specifically one of the questions in there about roles, I don't know if you've had this experience with previous roles, but this is kind of a new type of role for you; the modern work management senior director. You've got a team of people and they're in new roles as well. So how do you go about providing role clarity for members of your team, whether it's a new team like you have today or new kind of team function is different or new or even just you're coming into a leadership position? How have you made roles clear to those on your team and helped facilitate their belief that their role matters? 

[Mike] Yeah, I think, you know, one of the key things and it's talked about in the book, and they're all principles that I certainly, wholeheartedly agree with, is around being focused on the end result. And roles, whether it's my role or, you know, people on my team have always tended to be a bit open-ended just from my experience that you can't define: “here are the six things that you'll do in your role.” I mean, those are roles that I typically haven't had or haven't gravitated to. I always appreciate roles and I'm drawn to roles with a certain amount of ambiguity or improvisation required. And I kind of know that going in. And I think certainly this current role is a lot like that. You know, it was the senior director of modern work management, we want to help the company really transform and become, you know, kind of the world's leading example of what modern work management looks like by using the Workfront platform as well as principles and, you know, updating processes. You know, nobody's really done that before. So to come in and say to me, “here are the five things specifically you have to do in your role, Mike,” and then to my team and say, “I want you to do these six things and these four things,” you know, we're doing a lot of trailblazing here, and so I think the most important thing you can do with your team is continue to remind them of the end result. This is what “done” looks like, this is what we want to create at the end. 

And then continue to set milestones along the way that kind of say, hey, we know that we want to be this kind of world-class organization in terms of modern work. We think it's roughly in, you know, this northern direction. The best next action we can take is, you know, we're going to clean up some of the technical environment and we're going to work with the modern work enablement team and get people to start learning these principles. We're going to reassess in three months, and once we're there, then we, continue to go. We always know we're heading sort of in the right direction. So I've created a bit of latitude in my team's roles just because, you know, I know at a high level what I want them to do in terms of improving the technical environment and platform here, identifying and creating best practices. And, you know, how are we going to make sure that Workfront adopts them and that we can share them with our customers. But beyond that, to get down to specific, “here's the 32 bullet points of what you have to do,” again, I want to create an environment where, you know, my team can be creative and use their strengths because they have a lot of strengths in so many ways that I don't. But I want to rely on them and not box them in. 

Defining modern work:

[Jordan] That's great, ok so we've been using this phrase “modern work” and “modern work management.” I'm really curious because I've had conversations across the company, this is a phrase that's been used outside of our company. I've seen Microsoft use it, I’ve seen some others use it. But, Mike, I want to know, when we talk about modern work, what is that? What defines––in your mind––what is modern work? What's the difference between modern work and say, traditional work. I don't know, like, what's the distinction there? Why modern work? 

[Mike] I think one of the things that makes it distinctive to me when I think about modern work in many ways is, you know, kind of a blurring of boundaries. And it goes back to even in our job descriptions that we had before is, you know, some of the boundaries that are blurred today is where people do work. And I think one thing we've heard Alex say, and others say, “work is not a place, it's a thing we do.” In modern work, that's one thing that has changed. People don't show up at the office at 8:30 or 9:00 and then go home at 4:30 or 5:00 and leave their laptops on their desk. They kind of bring them with them, they have their phone. And, you know, if they're at their kid's soccer game or if they're at, you know, a meal on the weekend, they're kind of blurring the distinction between life and work. And we expect people to kind of have an aptitude with that because they have the devices and they're able to do it. So I think modern work is some blurring of boundaries in terms of where that work happens. 

But it's also boundaries between departments, between organizations, between partners, customers, and vendors and suppliers. Things happen much more real-time. So the need and ability to collaborate, you know, on work products where it's not just I ask you for something, you do it and you give it back to me. There's a collaboration between us and maybe between other people that needs to take place. So the skills that are required in that is a certain agility and dexterity to be able to, you know, continue to do work at different times and different locations and with different people in a way that it's not just kind of a binary, your on or you're off, there's a blending with it. So I think modern work is really much more transient in terms of locations and who you partner with and that it's much more collaborative. And it's not just, hey, what's Jordan's idea on X? 

Stakeholder management as a leader:

[Jordan] That's great. I want to segway, I think this is a good Segway into our next topic because, you know, when you think about blurring the boundaries between departments or teams and it being much more collaborative, and I'd say even creative. I think that there's a lot of unknown in front of a lot of companies in terms of what they're trying to figure out, and maybe what products they're delivering, and how they deliver it. So when it comes to these stakeholders and this concept of stakeholder management, we talked about that a little bit yesterday in our conversation, warming up for the interview. But, in your mind, when we think about the different stakeholders that are involved with getting something done, something that we’re trying to accomplish, what's the proper way to go about managing those stakeholders that are involved? 

[Mike] Well, it's a great question, because I think the most important part of it is when we talk about stakeholder management, I think a lot of people stop at stakeholder identification. They kind of identify, hey, here's the group of people who are interested in, involved in, or impacted by this particular product, or project, or initiative. Stakeholder management implies an ongoing process. So it's more than just saying, here's the five people who are stakeholders in the project. It's going out and identifying what's important to them. What issues do they have? What concerns do they have? You know, how do they want to be informed? How do they want to participate? And then following through with that. If you're on a one year project or a new product that's going to take, you know, 12 or 18 months, you know, stakeholder identification and what somebody wants in January may look very different in April, June or September. So if your stakeholder management process doesn't involve ongoing discussions, updates, input from these stakeholders, you're really failing and falling down with stakeholder management. Then you've just done stakeholder identification because needs change, and requirements change, and interests change. And if you haven't checked with somebody in March or April after you told them about it in January, and September comes around and they're no longer interested, you know that's something that you should have understood in April or March, you know, and understand how to get them involved. So I think the biggest part of stakeholder management that I have seen kind of get dropped is, you know, either an incomplete identification at the front, you identify one or two people. But the bigger kind of dropped ball is, you know, ongoing management throughout the project. You can't just touch base at the start of the project and then wait till, you know, another 12 months to talk to somebody again. 

[Jordan] Isn’t it easier though, to just kind of do your thing? 

[Mike] A lot of times! In terms of being a leader, I mean, we go to it and sometimes, you know, people will hide behind it. And they said, “Hey, this is what you told me in January.” You know, it's easy to go to a leader and say, “Hey, you approved this in January and now it's 12 months later.” You know, leaders have lots of things going on. And we talked about earlier, what are some of the characteristics of a leader that are independent of the title? And one of them is kind of taking accountability and taking the initiative. And that involves going back for 15 minutes to the leader, you got approval or support from in January, and going back to them a few months later and say, “here's where I am, here's where we're going. Any other input?” And at that point, you know, if you've kept them updated throughout, it's a very different discussion in December. If they say, “well, this isn't really what I wanted,” then if you hadn't talked to him for 12 months and they say, “well, I didn't see it for 12 months, you know, I had all these other things change.” It's incumbent on really the leader of that initiative, not the sponsor to say, “Hey, I changed my mind.” I mean, they should both have responsibility for it. But if you're accountable for the delivery, it's not enough to say, “well, my boss changed their mind,” because that's something you should have anticipated earlier on. 

[Jordan] I've heard a lot of people talk about how sometimes, maybe often, it's challenging to get executive buy-in. Well, let me just back up. So when I think stakeholder management, it's very much like the project management kind of term, you know, in terms of when I hear it. And I think that for me, when I hear you talk about it, identifying stakeholders and managing those stakeholders, for me, the whole reason why is to maintain buy-in and to maintain alignment, perhaps throughout the execution of whatever that initiative might be, right? Am I off?

[Mike] No, I mean, I think that's a big part of it. And I think, you know, people look at it as a chore. You know, sometimes it's you know, I identified them. Somebody told me to do this project. It must be important. I'm just doing what I'm told. And that goes, you know, I think to what we talked about earlier, which is of some sort of intrinsic value to the person leading the project. Are you doing the project just because somebody told you to and because you're checking an item off an agenda, or do you really want it to be successful? You know, if there's a personal project you have, whether it's, you know, is it painting your house, is it raising your child? Is it, you know, doing things, things that matter to you, you will do what it takes to make sure that it's successful. You know, and having people bought-in and having them support it is how you make sure your project is successful. You know, you've taken ownership in what the outcome is. 

You know, the people who will go in and identify stakeholders and then don't get the buy-in and at the end kind of throw up their hands and say, well, you know, it's the organization's fault; they didn't do it. They never really made the leap to say, I own this. I really care about this. And, you know, if you care about it, you want to know early on if people aren't supportive because then you can't be successful. You know, I think coming in with the Workfront at Wrokfront project and, you know, some of the work we're doing around modern work, I wouldn't have accepted the role and come into Workfront if I didn't feel a strong sense of conviction that, you know, Alex and Sue and the rest of the ELT were really, you know, bought in that this was something important to them. You know, without that, it would have been a silly risk on my part, and I would have been, you know, kind of pushing things uphill the whole time. With any project, getting buy-in upfront really gives you the confidence that what you're doing matters and it lets you care more about your job. Because if people aren't buying into it, then you should really question, why am I doing this? What’s the purpose of it? So when you get it. it almost goes back to the first principle, which is making work matter. If people aren't buying in, then you really have to question, does this work really matter? 

[Jordan] Yeah, I think it's interesting. So one of my favorite books is by Ray Dalio called Principles. And one of the concepts he talks about is this idea of meritocracy, where the best idea in the room should win. And, that to me, can fly in the face of what you were just talking about. Because if someone believes, and maybe it's true, but if someone believes that theirs is the best idea in the room; it is really the best way for us to go about doing this. Them holding onto that and kind of, you know, dismissing maybe what some of the stakeholders may think of or even their buy-in to executing that idea. Some people, I think, will lean in like, yeah, I know this is probably a great idea. Maybe they have like a key stakeholder that's bought into the idea and they just kind to run with that. 

Is there ever a situation where that sort of cavalier approach to work is worth it? Or do you always need the stakeholders, I mean, whether that’s the team and, you know, the shareholders or executives or your customers, like, is it always having everyone bought into the idea from beginning to end? 

[Mike] Well, I don't know, I think it's not something that lends itself to a total prescriptive approach because there's always various constraints in something. And in terms of timing, some projects are time constrained, so you can't go around and build consensus with 20 people to get something done; there's a sense of urgency. In terms of the idea of meritocracy, somebody may have a great idea, but imperfect information. So it may be a great idea in the absence of some external conflict or requirement that somebody else knows, you know, maybe there is an existing agreement with a supplier that says they have to buy a certain volume of product from us each year. Somebody has a new idea and they say, hey, I think we should go buy from this vendor. They rally up all the support and everybody goes, “ok, yeah, we should go buy from vendor X.” And that sounds like a great idea. Until you realize the legal department in procurement signed this deal that we're gonna buy from vendor Y because these are the other benefits we get. We get to co-lease their warehouse and we get this and we get that. And so, I think an important part of kind of the idea meritocracy is when people disagree or when stakeholders disagree, usually, it's not because people are stupid. You know, sometimes they are and they disagree. But sometimes it's just because you have different perspectives, ideas and information about why something won't work.

Now, where I think Dalio does a good job is in terms of, you know, probably radical transparency in terms of letting everybody see if everybody has the same information, you have a much better chance of getting to a consensus and agreement and buy-in than if, you know, people are in a culture where, you know, there's informational power, where I know something that you don't, Jordan, and I'm going to maintain my power over you by not sharing it with you in that kind of environment. You can't have idea meritocracy because, you know, we're not going to reach the same conclusions because of that. So, you know, the cavalier approach that you talked about is sometimes you need people to take an aggressive approach to really change things, and change agents have to do that, whether, you know, it's in business or in nonprofits or in politics or in, you know, families, when things need to be kind of shaken up or, you know, any kind of environment, change agents are not going to generally make people happy because they make them uncomfortable. So sometimes, you know, having to push change like that, you know, happens. But people have to understand, I think, you know, the intentions of somebody coming in and, you know, somebody who's being cavalier just to make a point. People aren't going to respect them. But if they trust the intention that this person is being kind of cavalier or aggressive or whatever, you know, because they're really trying to do what we want to do or make the company a better place. I think, you know, reasonable, rational people will say, ok, well, that's probably the right thing to do. 

[Jordan] Yeah. Yesterday you brought up this concept of hustle fouls. Tell me more about that. 

[Mike] Yeah. So I think in relationships, in business and, you know, just in life, if people make mistakes as a leader, what you want to see is fouls or mistakes that are made because people are hustling, they're trying to do the right thing and maybe they travel, maybe they get a charging foul, you know, or something like that. But they didn't get something done or they didn't make a mistake because, hey, I was waiting for approval or, you know, I wanted to wait until, you know, Thursday, because today I just wasn't in the mood for it or whatever. I think as long as people are taking steps, and if they make a mistake, but you go back through and you say, well, you know, you thought X and Y happened, but at least you were trying to make the right thing happen. I will take that 100 times out of 100 over somebody who says, well, I didn't do it because I was afraid I might fail. 

[Jordan] It's kind of like at Workfront, we do performance reviews or kind of performance coaching against getting it done and doing it right. And there's sort of four quadrants there. You know, of someone who is getting it done, but not doing it right. It’s kind of what you’re talking about, like even if they're––this is something that you hear in sports a lot––it's like you could have the best player in the league or a really talented individual on your team, but if they're toxic right now, then they're the first person that needs to be out of there. 

[Mike] Yeah, exactly. You know, I think the work ethic people often talk about when things aren't getting done, is it a skill issue or is it a will issue? You know, skill issues are generally easier to correct than a will issue. So when you talk about hustle fouls, that would be somebody who definitely has the will to do something, but they made a mistake because they either didn't know, they weren't trained, they didn't have the resources or whatever, but they were trying to get it done. So that kind of in the two by two you're talking about, that's somebody who's, you know, doing it right. Which is you've got the will, but, you know, we need to coach them. We need to give him some additional support. We need to get him some mentoring or partnering with somebody. And that's somebody you always want to have on the team because teaching people stuff is much easier than trying to change a person's motivation or different things like that. 

Defining commander’s intent:

[Jordan] That's great. So I want a transition to cover our final topic. And I think we started off with it talking about this concept of a commander's intent. Yep. We've introduced it in previous episodes. But this is a military concept, and as you were talking about it earlier, the commander's intent is supposed to be providing clarity of purpose, and also providing a set of parameters so that that team, like you were describing earlier in the episode, can kind of just do their thing, be creative and figure out how that outcome is going to be obtained. So let me ask you this. When it comes to commander's intent in business and regardless of the size of the initiative, when have you seen the commander's intent go wrong? Have there been situations where commander's intent goes wrong?

[Mike] Yeah, I think where it goes wrong is where a commander believes, or a business leader believes that they're giving intent, but it's ambiguous; it can be interpreted in different ways. You know, one of the things in the military when they're teaching commander's intent and training people on how to do it. You know what'll happen? The military will go do an exercise. And as part of the after-action review, they look at what happened during this mission and where could we have done better. And one of the very first things they do is they go back to the commander's intent in the planning and they actually begin to do some wordsmithing, you know, and they will ask the commander, “ok, this is what you wrote. Does that make sense to you? Could you have been more clear?” And then they'll turn to different people in the organization and say, “when they said do X, what did that mean to you?” And so there's a lot of work done on vocabulary and clarity and being explicit with expectations. And I think you really have to be clear in that and not presume people understand. 

One of the examples I like to use in it, in terms of setting expectations is if we were in a marketing organization and we wanted a partner to do something for us and we say, “Hey, we want you to do a customer brief for us, and we want it by next Friday.” In my mind, that's pretty clear. You know, I would say that's my commander's intent. I want a customer brief by next Friday. Well, to the agency, what that may mean is, a, when we do a customer brief, it is a 25-page word document and it goes into all of these different things. And it's going to cost us, you know, twenty-five thousand dollars. And this is what it's going to be. To me, where I came from, a customer brief is a two page PowerPoint with some demographics and what it is. And it shouldn't cost me any more than fifteen hundred dollars. So really pushing the limits to say, how clear am I? Am I clear about format? Am I clear about what the deliverables are going to look like? Am I clear what you know, everybody's going to feel or get out of it? And those kinds of things. 

So I think where commander's intent can go astray is when you leave too much ambiguity into what is really important to you. So that's why I think the way in the book that commander's intent is described is really strong because you don't only talk about what you want it to look like at the end, you say this is the single most important thing. So if you have to make tradeoffs, this is really what I want you to prioritize. And then talking about operational constraints, you know, I don't want it to cost more than X. I don't want you to work with this partner or, you know, you can't go into this geography or whatever the case may be. You allow people to be creative, but you also kind of say these are kind of really the guardrails. I don't want you to go left or right of this. But as long as you stay between those two, go and do whatever you want. 

[Jordan] Let me kind of recap that just to make sure I'm understanding. So we talk about being crystal clear on expectations. I mean, really what we're talking about is being crystal clear on what “done” looks like, what the outcome should be. And yesterday we were talking about this a little bit. It's like if there is any clarity you want to provide on the “how” you're flirting with this micromanagement thing. But really, when it comes to this concept, the commander's intent, how the military approaches it, it's just how clear are you on what the deliverable, what the outcome should be, what the constraints are around that project. But really, the “how” leaders like you're saying, you know, are simply providing that latitude to let their team do their thing. 

[Mike] Well, and in some cases, you know, “how” is important, you know, if you're in a regulated environment or there's something, you know, contractual or whatever that needs to go on, you need to be specific about that. So it's not that in a commander's intent, you avoid the how. It's just you need to be very mindful and deliberate about how much “how” you interject in that, you know, and you generally can give guidance upfront in terms of, hey, I think this is the way you should go. But what the commander's intent allows people to do is, you know, maybe they proceed down that path. And if they run into a roadblock, they don't just stop. Then they go around. 

The part of the context of commander's intent that's important to understand is in the military. The commander's intent is always part of what they call an operations order. So the commander's intent sits in front of an operations order, which really goes into pretty painstaking detail about how people expect the operation and the mission to take place. And so the commander's intent doesn't just say, I want you to go take this hill and, you know, do whatever, that kind of describes what the end result is. But there's a whole long approach built out after that that people going into the mission kind of know in their mind. Ok, this is our plan. This is where we're gonna get food. This is where we're going to drive. This is what we're going to do. And all of that is still laid out for people. 

What the commander's intent does is when a vehicle breaks down, when a bridge, you know, is closed or when something else happens, they still know, I still need to get to the top of this hill at the end of the day, you know the plan. You know, you keep doing the plan until it doesn't work. But then you still know what the end result is. You know, your mission isn’t just to drive down this road. Your mission is to get to the top of the hill. And if for some reason the road is unavailable, figure out another way to do it. So there's always an element of “how”, you know, the commander's intent generally doesn't absolve the leader of coming up with a “how”. But what it does is it gives, you know, his or her team the freedom and latitude to make decisions on their own without constantly having to call up and say, “Hey, Jordan, the bridge is closed. What do we do?” Or, you know, “Hey, Sue, these people weren't available. What do we do?” You know, by giving the commander's intent, it gives them creativity. But then it also frees up the leader to kind of manage bigger things and not have to go down and, you know, can continually hold somebody's hand on how things get done. 

So I think that that's an important part is, you know, the commander's intent shouldn't be micromanagement, but it doesn't mean that you don't do planning, that all you do is write out kind of a commander's intent and then you're kind of hands-off. What that does is it helps guide the organization that if in the course of executing what our plan is, something comes up, know that at the end of the day, this is really what we want. So you may have a customer support process that you follow, but if at the end of the day, the commander's intent is that we have, you know, incredible fans and delighted customers and all of that, then when the customer support rep is on the phone with a customer and they say, “Hey, I really don't like this.” And your process says you can't do X, the commander's intent gives you the freedom to respond or, you know, do something in a different way because, you know, the end result is I really want somebody happy. It's not, you know, the process is I have to be off the phone in a minute. I'm at 45 seconds now, so I’ve got to hang up quickly. You know, it helps you prioritize what you're going to do. 

Today’s best next action:

[Jordan] One last question for you. Let's say that this is a question I want to ask a lot of our guests or all of our guests. Let's say that you have a group of young leaders that are coming to you for one piece of advice on what they can do today to be a better leader on, say, some initiative that they're part of today. What would that one piece of advice be? 

[Mike] How can they be a better leader on one initiative they're on today.

[Jordan] Like there's a lot of nebulous advice we could give. But if someone is walking into their job today or maybe tomorrow, what is the one piece of advice you would give for them to be a better leader? 

[Mike] Well, I think, you know, being a better leader and really being a better teammate can end up being kind of the same thing. And I think it goes back to what we almost started with. It's, you know, take the initiative and take ownership. You know, I think as a leader what I most look for in my team and in other people is who's willing to take ownership for the outcome for something and who is willing to take the initiative. They don't wait around and wait for me to come up with an idea. They come back to me and say, “Hey, I did X, Y, and Z. And I think we should do this.” And, you know, those people rise to the top all the time. And so I think, you know, the best way to be a good leader, the best way to make a good impression on any team is, you know, don't just be a spectator. Get down and get in the game. Take some ownership and take some initiative. 

[Jordan]  Mike, thanks for being on the podcast today. 

[Mike] Thanks for having me Jordan!

[Jordan] Thanks for your time. 

[Mike] Take care. 

Thank you so much for listening to today's episode. You can find more information about the topic and continue the conversation at donerightpodcast.org. The Done Right podcast is hosted by me, Jordan Staples, the show is produced by Workfront. Our team includes Jeremy Tippetts and Marc Hansen. 

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