Workplaces need to become entrepreneurial networks, where I bring my ideas and creativity, and you bring yours, and we collaborate. No one owns us, we are all just working towards a common goal. In today’s economy, workplaces that don’t work that way are not going to get anyone to work for them.
In this episode, Richard and Peter talk with leadership coach and speaker Melissa Boggs. We dig into a range of topics, including her former role as Chief ScrumMaster at Scrum Alliance, the lesser-known challenges of leadership, coaching and being coached, and the ways the rules of work need to change to create more human-centric organizations.
Mentioned in the episode
Melissa Boggs Speaking & Consulting
Menlo Innovations’ Hiring Process
Episode Transcript
Richard Lawrence
Today we’re delighted to welcome our friend Melissa Boggs to the Humanizing Work Show. Melissa is a leadership coach, keynote speaker, and what she calls an “employee experience designer,” which we’ll dig into more later. We got to know Melissa originally as a fellow Scrum Alliance certified coach and trainer, and for a while she was actually co-CEO of Scrum Alliance.Melissa hosts the Wild Hearts at Work Podcast. Peter and I are really excited to dig into the stories behind all of this and more so, Melissa, welcome to the Humanizing Work Show.
Melissa Boggs
Thank you for having me. It’s always fun talking to both of you, so this is going to be a good, fun time.
Richard
We think so too. What does the typical bio, like what somebody might get from your website or your LinkedIn profile leave out, that’s important about your story?
Melissa
Ooh. What a juicy question. This is not what you’re asking for, but, um, I am an avid roller skater. I roller skate three times a week, and it should be in my bio because it is such a huge part of my life. So, um, that’s not the business thing that you were looking for, but… No, that
Richard
No, actually that is one of the things in our notes about what you might say. So I knew about this.
Melissa
It has been my sanity through the pandemic, and my exercise, my community. So it is a huge part of what I do when I am not sitting at this very desk.
Richard
Other than roller skating, what else should people know about you?
Melissa
I had an interesting conversation with my husband the other day actually. We were talking about our youth and our kids. We have two teenagers, and we were talking about rule followers and rule breakers, right? Our son is very much a rule follower.
He likes rules, he follows them to the T. We used to have conversations with his teachers about how he does not need to enforce the rules in other children, that the teachers can handle that. My husband, on the other hand, would tell you that he was a rule breaker in school when he was a kid–just a lot of mischief, like kids do.
He was a rule breaker. And I was sitting there in this conversation not relating to either one of them because I was definitely not a rule breaker; I’m not now a rule breaker. However, I find myself feeling very rebellious against rules, and I honestly don’t remember whether it was me or my husband, but one of us hit on it and said, “No, actually what I am is a rule changer and I will follow the rules until I’ve convinced someone that they can be changed– until I convince someone that things would be better if we had a different set of rules. And when I look at my entire life, I have always been that way. Like I will follow it because I was taught to: you know– military father, religious upbringing– but I will also push against it until it is, in my opinion, a fairer rule or you know, a more open, freer set of rules.
And so I think that’s a pretty descriptive thing that is missing from my bio . Maybe it needs to be in there though.
Richard
If you look back at just the kind of resume version of your bio, what were the job titles? You see this move from process analyst and systems analyst to, ultimately, the people-centric leader, coach, and speaker that we’ve come to know.
What caused that change for you? And maybe how is that connected to what you just described?
Melissa
I would say what I just described is what caused that change. I started out, even in those roles though, like as a process analyst, a systems analyst, I was always sort of looking for what’s the better way.
Like what’s the way that we haven’t thought of yet? What’s the path through this that leads us to, you know, more creativity? Um, at one time I was focused on more efficiency, although I would not claim that now. Um, it was always like, what are we missing? What’s the different pattern here that we could find?
And so I think that just threaded its way through the rest of my career. You know, I found myself in the Agile space and there’s a lot of that, right? A lot of that just in our values and principles in the Agile space. But I think I’ve threaded that even further beyond, and it’s “Agile plus.” So yeah, I think that’s always been a thread that I just only recently would put my finger on. I’m looking to change the rules to a better way, a more humanizing way, if you will.
Peter
I like that phrase. A lot of that culminated in your role as the co- CEO of the Scrum Alliance, and I’ve always wondered how that came about. How did you land that gig? Did somebody reach out to you? Did you hear about it and apply? I’ve always been curious about the backstory for how you ended up as the co-CEO.
Melissa
It’s so funny. People always think it’s so mysterious, but actually there’s a little bit of a backstory, but frankly, I applied for the job and interviewed for the job. There’s always, of course, timing; and time and place types of things that always happen. I happened to move to the area, quite close to the Scrum Alliance office the year before this job came to be. I had had a lot of interactions with the Scrum Alliance staff, as a certified enterprise coach, as a member of the guide community.
I knew a number of them just from having been a speaker at that point, running into them at conferences. I had actually (a lot of people don’t know this), applied for a job previously– a different job. They had a sort of learning and development, people and culture job available when I first moved here.
So that was probably a year– a little over a year prior and I did not get that job. And I always use that too, by the way, as a “one door closes, another door opens” kind of thing when I’m speaking with people who are upset about not getting a certain job, I’m like, “Well, let me tell you, I didn’t get the first job.”
And then I got the job’s boss. I say that very lightly in jest, but ultimately they hired a chief product owner and then also wanted to hire a chief ScrumMaster, which was initially kind of the main point of that job. So I was the co-CEO in terms of traditional titles, but really our jobs were to be the chief product owner and the chief ScrumMaster.
And when I read the job description for this company that had essentially raised me (I mean, I went through all of the different journeys of Scrum Alliance), my community was Scrum Alliance. I had become a speaker in this community, and I felt a great debt of gratitude to Scrum Alliance as a whole, like as a community, as the staff.
And when I read the job description, it was one of those moments where it was like, “Oh, I might actually be qualified for this job.” Quick side note, but it’s just a funny story: I learned that my doctor is only like eight weeks older than me, and it was one of those like, “Oh, we are the adults now.” Like, “We are the doctors, we are the CEOs, we are the, the big kids.”
You know, we’re at the adult table. We’re not at the children’s table anymore. And it was kinda one of those moments where I was like, “I am qualified for what they’re looking for.” And I would tell anybody–I wouldn’t have said at that time that I would be qualified for any CEO job, but I was uniquely qualified for this one.
They wanted someone who had depth of agile experience, who had coaching skills, who had, you know, sort of been in the community and in this space. And that was me. And I literally lived seven minutes away. I put in my resume and a cover letter, just like any other job, and I was interviewed by the board a couple of times. I flew to Miami, where they were having their typical quarterly (it was quarterly at that point), board meeting and were doing interviews. And I believe at that point I was in the top two and we had to do a presentation, and then go through kind of an interview process.
The one thing I will say about that, and I’ve talked about this in a couple other situations, but I think it’s so important, I decided going into that interview process, especially in Miami, where I had to stand in front of them and present, that I was going to be the most me that I could possibly be, like almost to the extreme.
Because I didn’t want them to hire me if it wasn’t me that they wanted, if they hired someone that I was pretending to be in an interview like we all do, or we at least have all done– that I wasn’t going to be able to lead the way that I wanted to lead.
Richard
What’s an example of that, Melissa?
Melissa
Well, here’s an example from the interview: The very first thing that I asked them to do– and these were the board of directors and some of the executive leadership in the company at the time. There were probably a total of about 20 of them in the room. I asked them to get up and do a rock paper, scissors tournament at a stuffy conference room in a hotel.
And I did it on purpose. I wasn’t trying to be manipulative, but I was like, “I’m going to come into board meetings and ask you to do crazy stuff because this is who I am and this is what I bring to the table.” And it lightened the room because it really was like a stuffy conference room in a U-shape.
In fact, I walked into the room and I was like, “Oh God, how am I going to make this work?”
But you know, the energy was different after that. And you know, I used post-it notes and sharpies throughout my entire interview and presentation. And then even in my slide deck, I intentionally used a picture of myself and my family where we looked completely goofy and I was in very casual clothing.
And again, it was the first time I ever interviewed for a job that I was serious– when I was like, “I need you to hire me for who I am and what I bring to the table. Because if you want someone who is traditional and a rule follower and a stuffy suit person, that is not what you’re ever going to get from me, and we are going to have a fight the entire time I work here if that’s what you think you’re getting.” And I was so appreciative because they called me within a couple of hours the same day and offered me the job. And I knew from that moment, like it gave me such confidence. This is what I always tell people when they’re interviewing for a job: If you can do that for yourself, then when you walk in on day one, you know that they know what they’re getting. You know that what you have offered is what they want. and it gave me the courage to do so many things that I may have not otherwise felt confident in doing or asking of them because I asked the board to change at times too.
And again, they knew I was going to do that. I asked them to play rock, paper, scissors, so they knew I was going to do that.
Peter
Where did the courage come from? It sounds like it was an evolving process, like you mentioned earlier, maybe you didn’t live into it as fully in previous interviews as you did in that one. And I’m curious if you can trace that. Like what gave you the courage, what gave you the confidence to say, “You know what, I’m just going to be me”?
Melissa
It’s a great question. I think it was two things. I don’t know if I can trace it back very far. I think this was a very pivotal moment for me as a human. The stakes were really high for me, not in the interview, but in the job itself.
And so, again, like with stakes that high, I want this job, but I want it for the right reasons, and I don’t want to get stuck in a place where they don’t want what I have to offer. And now I’ve got this job and I don’t want to be someone else. I also have a very close friend that really just sort of hit it home for me.
He was helping me with some of the slides and he has always pushed me to be the most me that I can be. And there was just something about that moment when I was working on the slides and I think it was about the picture. I think I was using like a more, you know, normal headshot picture. And he said, “Who are you trying to be?
And I was just like, “Hmm, okay. You’re right. I really should just be who I’m going to be every single day.” And so I give him a lot of credit. Shout out Simon for making that turning point before I walked into that room.
Peter
Hmm. It’s interesting that we’re all coaches. We all try to have that kind of impact in other people’s lives and it’s still so powerful when we have a great coach ask us a question like that. That just totally shifts our perspective.
Melissa
He’s done that for me at a number of points and even while I was at Scrum Alliance, he was often the one who asked the question that made me go back to myself. It wasn’t always some coaching question; it was always directing me back to me, directing me to trust in myself, and to trust my instincts and to trust that what I bring to the table is enough or not too much. I tend to actually believe that I’m too much more than not enough. He has done that for me many times over the years.
Peter
I think that’s a lesson for all of the coaches that are listening. Great coaches don’t bring in, necessarily, you know– the different perspective, although they can. But it’s really how do you tap into who this person really is and the stories we tell about ourselves and what stories are going to serve us and what stories might be limiting right now.
Melissa
I feel that in my bones, as a coachee and as a coach, uh huh.
Peter
So, as you reflect on the time that you spent at the Scrum Alliance, I’ve got three questions for you and you can kind of answer in any order, but I’ll give you all three, and then we can go. So I’m curious what you want to brag about at the Scrum Alliance. I’m curious what your biggest surprise was in your time there, and I’m curious in what ways your time at the Scrum Alliance helped you to grow.
Melissa
Oh my!
Peter
So, “brag about,” “biggest surprise,” and “What caused you to grow.”
Melissa
All right. Brag about is easy. So easy. The human beings that worked at Scrum Alliance for the two years that I was there, I will brag on until the day that I die. We went through some stuff, I mean some real stuff. There was a restructure of the entire organization.
There was totally upending– talk about changing rules– we changed all the rules for ourselves internally. There was a lot of change in the two years that I was there, and I saw these folks just get closer and closer with one another instead of allowing the change and the conflict to push us away from one another.
And mind you, the second year of this was Covid. Instead of allowing it to push us away from one another, we allowed it to bring us closer together because we had curiosity and we had struggle. And when you struggle, if you allow it to bring you together, then you’re closer knit and you’re bonded.
And those folks know they will be my people for life. So, I mean, I could brag on all of the different things that we actually did that would be like six episodes all in itself. But at the end of the day, the thing that I brag on is that it became like this close-knit group of people who accepted one another, who challenged me and challenged each other.
When it came to “Should we do this because we’ve already always done it or should we do it because it’s the right thing to do?” And generally speaking, we always believed that we could work things out. Now, trust me, there were moments; there were moments of doubt, there were moments that everyone has in transformation.
But at the end of the day, I believe that the people that were there felt that we could work it out. Like we could figure things out– and that’s what makes it work. So I will always brag on those 50 to 60 plus people that were there during my time there. And I love them with my whole heart and they know that.
Peter
So I have a follow-up question on that before we move into the other two questions. We see this unstated bias in a lot of companies, and one that I’ve heard you talk about in your podcast. If we take a human-centric approach to work, we focus on the people, on the employees, we’re somehow decreasing the likelihood of business success.
And I’m curious how you think about that trade off, or if you even see it as a trade off or how you address that common bias.
Melissa
I don’t think it’s a trade off. I think it depends on how you define success. And I’m not trying to be coachy, and I’m not trying to be, you know, like Woo Woo-ey. But I do believe that by handing over choice and clarity and context to the people that I worked with, they had more creativity, they had more engagement in the work that we were doing because they felt ownership of it. And I defined success by our progress toward our mission, by our ability to serve the people of the Scrum Alliance community. and not by money, not by revenue. It’s important, I’m not discounting it, but especially in our case where we were an association, we were there to support our members.
I believe that we did that regardless of what money looked like. And I’m not saying money was bad, because it wasn’t. But that’s not what I was interested in. I think if you serve your customers, if you serve your members, the money will come, right? People will show up as members or as customers because you’re serving them.
Why would they otherwise? They might show up from your marketing, but they don’t necessarily stay. If you serve them, they will stay.
Peter
So, biggest surprise, how did you grow?
Melissa
The biggest surprise was what we were able to accomplish in terms of change in the organization. This sort of harkens back to the bragging, so maybe now I’m doing the bragging part too.
We restructured the organization into fully cross-functional teams that supported personas. We had a system of essentially communities of practice, so we called them co-ops. We hired in a completely different way than any, almost anyone I’ve ever heard of. It was inspired by Menlo and how they do extreme interviewing, but we really did take it in our own direction with our own flavor.
We had an entirely new compensation system designed that was divorced from the job market, that we didn’t actually fully get to implementing before I left. But it was absolutely different from anything I’d ever seen. And so the surprise comes that we were actually able to do all of those things. And I think I was only surprised because I had never been in a position before where I had the amount of influence and authority to make those things happen.
I mean, as a coach, all you can do is sort of like, “Well, have you thought about this?” You know? And suddenly I was in a role where I was not only allowed to implement things in cooperation with our team, but encouraged to, like literally it was my job to do those things. And so I think I was just surprised by what you actually can do when you have a leader who’s invested in creating a human-centric organization.
And it just so happened that that leader was me. But also with the support of the board, I have to say, there wasn’t anything that I brought in front of them– you know, I had a lot of authority and leeway in my role, but also when you’re making huge changes like that, you bring them to the board and they always asked me a ton of questions for sure– but they supported me.
I cannot think of a major thing like that that I brought in front of them that they said, “No, you should not do that.” They gave me great feedback. I definitely changed things with their feedback, but I was surprised by their support, frankly, because there were definitely times I was prepared to fight and rarely did I have to fight. I just had to be able to justify and explain why it was the best thing. So I, I will always appreciate that.
Peter
So we’ll drop a link in the show notes to some literature about Menlo’s hiring process. I’m really curious to hear just a high level overview of the compensation model that you were in the process of putting in place because, divorced from the job market, I’m sure you would have many compensation experts saying, “Ah, how are we going to hire without Radford codes?” And Sure. Those types of things. So maybe you could just give us some of the principles behind it.
Melissa
I will. And I also, this is a thing that I have continued to build on and talk about with clients. So the bottom line premise is, especially in organizations that are intending to be more agile, we talk about T-shaped skills, right?
But rarely have we ever discussed that we need to compensate differently for T-shaped skills than we would for someone who was like, “I was hired to do this job and this is the job that I do.” So an example that I’ll give is that when we started becoming a lot more cross-functional at Scrum Alliance, there is a difference in compensation between someone who is hired into, say, our customer support team and someone who is in marketing.
But what we’ve now done is created cross-functional teams, and– for everyone listening– when I talk about cross-functional in this organization, every team had someone from our customer support, co-op, marketing, development, education. Every team had those components. We no longer had these siloed departments, but what that meant is if you’re in this team, then you’re no longer only doing customer support, right?
You are doing little pieces of everything. I remember one of our ScrumMasters talking about learning a little bit of just web development. Not a ton. He didn’t become a developer, but, you know, enough to kind of help out. We can’t continue to compensate someone solely based on what the job market says that customer support is compensated for when they’re doing all of these other tasks.
So the system that we had designed was essentially stacking skills and saying like, there’s a base salary for everyone. And then on top of that base salary, you are stacking your skills based on your skill and experience in each of those capabilities. So I don’t want to give away too much, but sort of like if you think about how some organizations do banding, right?
But imagine doing banding not just for one skill, but for multiple skills. So you’re adding on “My annual salary is a composite.” That was a word that we used a lot: My skill level for this skill; my skill level for this skill; and my skill level for this skill. And it really encouraged both trying new skills and also becoming like a teacher, and other skills, right? So you’re compensated differently if you’re at the point where you’re not necessarily doing that job every day, but rather you’re mentoring people who are, but you also might be compensated for just dipping your toe in this, you know, like the example I gave you about web development.
He’s not going to be compensated the same as a developer who does it all day, every day. But we want to recognize that you’re putting in work there and you’re learning and you’re contributing in that skill. And so it’s almost like Lego, like you’re stacking these things together. And we even got to the point of presenting it to the board and we’re starting to do the floor, the foundational work of “Where is each person,” you know, “What would their compensation look like if we rolled this out?”
And that’s when I ended up moving on and they didn’t continue with it to my knowledge.
Peter
Mm-hmm. Yeah. Really interesting. In what ways did it cause you to grow?
Melissa
In every possible way that you could imagine
It really is hard. Like I grew professionally, I grew personally. I’m still growing. I’ve been gone now almost two years, and I feel like I’m still growing from that experience. It was the most challenging and rewarding two years to date– at least in my professional life. I certainly found a courage I didn’t know I had, starting with that interview, I stopped trying to lead like other people and led like myself. Because I came up in the tech world, I spent a lot of time being the only women on a management team of all men. Or being sort of like the empathetic one, the soft one, and for a long time saw that as a challenge to overcome rather than, no, that is literally my superpower.
My superpower is my ability to see people and to help them see themselves. And I think as a coach, it’s easy to see that as a superpower, but when you step into a leadership position, especially one like that, it would be easy to see it as a challenge to overcome. So I really learned how to lean into that and to accept myself and lean into that superpower.
Also, just logistically and tactically, there were things that I did not know how to do before and I was really surprised how quickly I was able to grow in things like budgeting. And that might sound silly, but when you’ve never managed the budget for an entire company and you want to do it in a very distributed way, at first that was super intimidating; but I learned that pretty quickly. And then just in my own personal growth, I think the biggest one that I didn’t really recognize until I left, I loved that job so much, and I was so invested in the company before I even worked there that frankly I allowed it to become my identity. I was so invested in being successful for the sake of the people that were on my team and the people that depended on us from the community that I became really sort of surrounded by it. I don’t know if that makes any sense, but when the time came, it became apparent that I was probably going to have to exit by my own choice.
I recognized how part of it was so hard because that had become who I was. Like who was I if I wasn’t the leader of Scrum Alliance? And I did recognize upon my exit how unhealthy that was and how I can deeply love something and still need to have a sense of identity outside of that. And that took a long time to heal from.
It really did. I knew what I did was the right thing. I knew I had to leave for many reasons, but that didn’t make it easy by any stretch. And I really had to come to terms with like, who am I now after that? And I have, and I still have so much love for them, but that was a really big growth opportunity for me.
I had never been so invested in something that I didn’t know who I was later. That was a really big deal.
Peter
I think our listeners would be curious a little bit about kind of the shared leadership experience. And I would almost call it an experiment–and some of the potential benefits or challenges to having kind of a shared leadership role.
And I know that there was some role separation, a little bit between Chief Product Owner, Chief ScrumMaster, but if you just think of sharing leadership responsibility as a general idea, I’m curious on your take on some of the potential benefits, some of the potential challenges of that in terms of benefits.
Melissa
There were definitely moments where my partner and I looked at each other and said, “Oh my gosh, I’m glad I’m not doing this alone.” You know, there were hard moments where we had to make hard decisions when it was nice to have someone, you know, sitting there with you validating or not, you know, or kind of going back and forth on decisions.
But ultimately, coming to it together and saying, “Okay, this is what we’re going to do.” That was a huge benefit. And there were even times that literally big things were going on in the company simultaneously that otherwise, if I were one person or he was one person, we could not have done those things at the same time.
I remember we had a big teaming workshop going on. There was a time that Scrum Alliance had two buildings and I was in one building doing the teaming workshop, which was very much in my role. And he was in the other building, meeting with some partners, which was very much in his role. And we were both doing exactly what we should be doing.
But if that had been one person, you could not have been doing those things at the same time. And so there was definitely some benefit in that. And then there’s this crossover like benefit and challenge. I don’t think you can step too far away from the fact that it wasn’t just shared leadership. We were in very specific roles that even on teams, people have this designed inherent conflict, right?
My role was to advocate for our team and to make sure that the team wasn’t biting off more than they could chew and making sure that they had distributed authority. My partner’s role was to be a Product Owner, so he was there to advocate for getting things out the door and what the customer needed, et cetera.
And so there’s an inherent conflict that Product Owners and ScrumMasters have on a team level that we had at our level. And I think one of the biggest moments was when we realized that that was happening and it was difficult but important to go, “I’m not arguing with you, the person; I’m arguing with you the Product Owner, and they’re doing their job. but I am doing my job and it is okay for me to do my job too. And to kind of like depersonalize that, in some moments, was really useful. And I do believe some of that made it better because then we were advocating for both and recognizing there is some amount of conflict in that– we can’t give the customer everything they want all the time, but we can do our best to balance that with the emotional and mental wellbeing of the team.
I think that was both a benefit and a challenge at the same time.
Peter
And I think that there’s a, long-term/ short-term, trade off that often happens in companies where if you just think in the short term, the Product Owner’s going to advocate to get just this next thing out the door. And the ScrumMaster might be advocating for “Yes, but , if we do that, then that means we’re going to have to slow down on the thing after that.”
And it’s not like the customers are going to stop requesting more things now. So are we actually setting ourselves up to be successful over the long term? Or are we making a trade off on short term benefit now where we’re kind of shooting ourselves in the foot for how we can deliver over time? So this may be just another way to describe the inherent tension is a short-term benefit /long-term benefit.
Melissa
And you see that a lot too, even just with non co-leaders, just with leaders. It’s not just a matter of like getting this one thing out the door, but you’re breaking trust with your team who is telling you they can’t get that thing out the door. And so not only are you, you know, trying to like push them to do something, but then the next time they’re not going to trust you to tell you that they can’t do it.
And you’re going to continually fall short and be wondering why. Well, because they tried to tell you the truth a couple times ago. and you struggled to listen and so now they’re not going to tell you anymore, but they’re still going to have a hard time, you know, meeting these exceptional goals.
Richard
You describe one aspect of your current work as employee experience design, which is not a phrase we see very often; tell us more about what that is, what that looks like in your work.
Melissa
So the way that I describe this is that I help leaders close the gap between them and their teams. This is like the perfect segue from what I just said, because I’ve been on both sides of it now, right? I’ve obviously been an employee many, many times in my life, and after having been a C E O, I have a whole new perspective.
There’s also a whole bunch of things that people don’t understand about that role and how difficult it can be and how constrained it can be. And so now I feel like I have this empathy that not everyone has about “Oh gosh, I see where you’re coming from and I also see where you’re coming from.”
So how do we close this gap? When I say “employee experience design,” I do that in a bunch of different ways. Sometimes that is workshops with the leader and their team. Sometimes it’s org design and sort of culture design where we talk about what are the values of the company and how do we set up structures that allow that culture to flourish?
Because culture is just behavior. I mean, it’s tradition, it’s habits, it’s behavior. So we can’t force behavior, but you can set up the right experience that leans into the behaviors that you want to see. And then also I speak, I do keynotes around the same topic, and that is part of the employee experience design as well.
Because if you put someone in front of your employees, and that person is talking, I have a model, I have a kind of a Maslow inspired model, and it talks about context, clarity, craft, choice, and co-creation. If you put that person (me) in front of your employees and they’re talking about the importance of this, you are sending a message to your employees and you are creating an experience for them that this is important to you too.
And that, even if you’re not there yet, you’re willing to try to get there or you wouldn’t be putting this person in front of them. And so all of it is in service of how do we create this humanized work, [“I’m pandering,” Melissa jokes.] experience of this place where people feel like they have ownership of the future of their company regardless of where they are in the organization. And how do you as a leader communicate that, if that’s how you feel, that they do have ownership, and close that gap.
Richard
How often do you talk with leaders and discover that you’re misaligned on that? Like it would not be honest for you to put me up in front of your people because you don’t seem to value these things.
Melissa
That’s a great question. I think there’s a time that my answer would’ve been “All the time,” but this is going to shock you. When I went into my own practice and my own speaking business and I built my website and I built all my collateral, I was very, very intentional about understanding who my target audience was and intentionally use language that is going to bring those people in and scare away everyone else. And I don’t mean that to be facetious in any way, but I am a very niche practitioner and speaker and you only do want me if these things are important to you– otherwise you’re sending a very confusing message. I actually had a speaking client recently that on paper, might not have been a great fit.
So when they first reached out to me and wanted me to come speak, it was an association. I was like, “I think we need to walk through this talk with the point of contact, the chair of this association.” And I said, “I just want to make sure that this is what you want.” And then it was the talk with that model about the five things that employees need to increase their own engagement. We walked through it and surprisingly she was like, “No, that’s exactly what they need to hear.” And it’s a little different maybe when it’s an association and not your employees. But yes, we want to send these people out into the world with this message, and that was great. But certainly I do try to vet it because I want to be aligned.
I don’t want to create frustration or confusion in an organization, but there are plenty of them out there who want to close this gap, especially in the wake of the pandemic, recognize that we can’t work the way that we used to. And so I just get really excited when I get those calls because sometimes they know exactly what it is, they just don’t know how, or sometimes they bring me in to speak because they need it to come from someone else. Like, “See, I’m serious, I’m not spewing things that leaders say, I mean it. I even brought this woman in to talk about it, see?” Sometimes it’s just a validation of the message that they’re already giving.
Richard
A moment ago, you mentioned that there are things people don’t understand about the CEO role and what’s hard about it. What should people understand? What are the three or four things you wish people knew about what it’s like to be a CEO?
Melissa
I think the biggest thing that I felt at times misunderstood was that I didn’t have endless power.
Like even the CEO doesn’t have unlimited budget, unlimited authority. I still reported to the board of directors and I still was responsible to the community of Scrum Alliance and so, and I was responsible to everyone in the company. And so, you know, I, there were definitely times when. There was something that someone on the team either suggested or wanted that generally speaking, yeah, that makes sense, but it doesn’t meet the needs of everyone, or it may not seem fair, or I literally just can’t do that for whatever, like legal reason.
And so, yeah, just the idea that, um, that the power is not endless. The authority is not endless. That in fact the CEO has so many stakeholders, and that was, I’m not sure if that was a surprise to me, but I’m not sure I had the amount of empathy that I should have had. I always, I tell the story, I actually have a talk that I had done for a while called from coach to CEO and back, and I talked about this very thing and I told this story about how when we did the big teaming workshop that I was talking about before. There was a moment about halfway through the workshop that it was a little bit dark, like people were scared, the employees were scared. Um, we were basically doing like a dynamic reteaming where people could choose their own team. There’s a lot of fear.
What if I choose the wrong team? What if I choose a team and I don’t like the people on my team? You know, there’s just a lot of like angst that was happening about halfway through. And I was in a room during lunch with some of the coaches that were helping us facilitate. And I am literally like have my head in my hands, like my head’s down.
I am like, not crying, but close and just like, is this going to work out? Like, have we made a huge mistake? And one of them looked at me and said, “Look, all I gotta do is blah, blah, blah.” And they were trying to be encouraging and they were trying to be kind. And it was such a moment, like one of those, like out of body moments because there was like the reaction that I was having to them and then the recognition that I had been them.
And I looked at that person and I said, I know you love me and I know that you were trying to help, but this is a lot harder for me than it is for you right now. And of course, you know, they were like, oh no, you’re so right. Like, I, I’m sorry. But again, at that same moment, I was like, I have said that I have been there.
And it wasn’t until this very moment that I realized how naive that could be and how I did not know the gravity of what that person was feeling in that moment. And for the record, everything turned out fine. That coach was amazing. But it was such a pivotal moment for me to realize like, sometimes you can’t understand until you’re there.
Peter
Because not every coach out there is going to be a CEO, has that chance, or might even want that.
I’ll just share that in my time as a coach, I did have this moment where I kind of flipped the same way that you did, but without being the CEO. And there were a lot of things that led up to it. But for many years I was really frustrated with the CEO of the company saying, why don’t they just, why don’t they just, why don’t they just, and I think it was probably in a coaching session around, like leadership circle profile or something, where I had this moment where I said, “Oh, that CEO is a human being who is dealing with huge challenges.”
Like, their identity is on the line. They’re taking a huge risk trying to make this transformation. Who am I to tell them how to do it? I don’t have that weight on my shoulders. And it was the coolest experience because all the frustration just floated off my shoulders with that person, and the empathy just evaporated it.
So for people who are listening that are coaches, it’s super valuable to be in that chair to really experience it like you did. I also think it’s possible to let your empathy get you as close as you can get without actually sitting in the seat. And just to realize there’s a tremendous amount of weight on a CEO’s shoulder or any leader’s shoulder.
They’re human beings doing their darnedest to get the right results. And they probably deeply care about the people as much as you do. And they just have a lot to deal with. And if you can get rid of the anger and just stop judging and saying, “Oh, they should do it this way, they should do it this way,” and replace “should” with “Wow, what a hard job they have right now.” For me, that was transformational in how I thought about coaching, and it switched it from being a somewhat adversarial relationship where I was trying to poke it, poke it, poke it, poke it, provoke it, do what I could to advocate, change to “how can I work with them and be in service to them as much as I’m in service to the team?”
And that for me was career-changing for sure. And life-changing in a lot of ways as well.
Melissa
Yeah. You kind of said it. There are two key words that always stand out to me in my own thinking, if this starts to come up: “should,” like you said, and then earlier you said, “just,” cause what that coach said to me in that moment is, “why don’t you just, or you can just,” so anytime that I catch myself with the word, “just” even “just,” I mean, not even with my family. Like, now that word is kind of like a flag to me. Am I being very empathetic if I am minimizing something to “just?” “Why don’t you just do this?” You know, it always has like a tone to it too.
Peter
Like there should be a comma, “you idiot” after it, right?
Melissa
Right. Or you a wimp, or…
Peter
Yeah.
Richard
We have a saying in our house. You know, “just” is doing a lot of work there.
Melissa
Yes…
Richard
My wife works for an event center and she always gets these requests from clients like, “Oh yeah, we’re just going to need you to live stream this whole thing.”
Melissa
No big deal.
Richard
“Just” is doing a lot of work there.
Melissa
I do know that it was a pivotal moment for that coach too, because we had a very close relationship and the fact that I was able to actually just kind of clap back in that moment and be like, you know, most leaders probably wouldn’t say that back in that moment. So it was actually like a really cool moment for everyone, I think. A learning opportunity. And they have since apologized. I’m like, you don’t have to apologize. I’m not telling that story so that you apologized. It was me. Like I was the one that was like, “Oh, I see.”
Richard
Like many effective coaches that we know, we know you’ve been coached yourself in various contexts, like you’re describing here. How else has being on the client side informed your own coaching?
Melissa
It’s taught me a lot about stances. I’ve been very fortunate that the coaches that I have had, have also been friends in the sense that I could be very direct with them if the stance that they were taking was not working. And that has caused me, now, to always create a coaching agreement or a working agreement with my clients, and one of the first things I say is, my request of you is that you tell me if I need to change stances; that you tell me if I am advising when really you just need a sounding board or the opposite.
If I’m coaching and you are like, “Look, you’re clearly leading me somewhere, will you just tell me the answer?” So it’s given me the—I don’t know that “permission” is the right word. I want to give them permission to give me that feedback in that moment, because sometimes we know what we need and sometimes we don’t.
But if you know that you just need a place to safely vent, then I don’t want to be giving you advice. I know I’ve had these moments, too where it’s like, “I know I have the answer. I know it’s in here. I just need to untangle the spaghetti, you know, so just help me untangle.” So I think that’s probably the biggest way. It’s knowing that I need to give permission and ask for them to do that.
Peter
Let’s talk a little bit about your podcast, Wild Hearts at Work, which is an awesome name by the way. A couple of standout episodes for me were the interview you did with Rob Krecak, uh, Tiffany Farriss…
There are some great episodes on there that were packed with insight and important messages and heart and all the great things. And I know this question is kind of like asking somebody “Which kid is your favorite,” but what moments or episodes particularly stand out to you as you reflect on it now? I mean, we all have favorite attributes about our kids, so, what are some moments that stand out to you?
Melissa
Peter’s trying to blaze a path for me so that I don’t upset any of my guests. There are definitely a couple that stand out. The very first episode was the CEO of the company that I always say I grew up in. I started working at the scooter store when I was 20 years old. I worked there for 12 years. It was one of the most human-centric companies I have ever heard of. And they were so far ahead of their time because, and y’all can do math and figure out how old I am, but that was over 20 years ago. And so it was such a full circle moment to have him on the podcast and to just talk about the company.
And sadly, the company is not in business any longer for other reasons, but I think it was good for me. I think it was healing for him. And we just got to talk about it from –it was interesting– I was an employee, and again, I was 20 when I started there, but I grew up there. He knew me.
And to hear about it from his perspective, you know, something that was 20 years ago, but like, why did you do the things that you did? Why did it matter that we all knew what our core values were? Why did it matter that literally everyone in the company could recite the mission? At any given moment. I think it was good for him too, to hear.
Yeah. That mattered to me. Like when we rewrote the core values and you asked everyone in the company for their input and I could see myself in the new newly written values that mattered to me. And so that was such a cool, like full circle, kick off this podcast in like the wild, hardest way. So that was a big one.
I loved Rich Sheridan. Everyone loves Rich Sheridan. It was really neat to talk with him because again, a lot of the things at Scrum Alliance that I did were sort of seeded by some of the work he did. And then I would take it and like blow it up in a colorful way and do it differently. And then I had two episodes (first, second) in the second season where I actually brought back people from the first season and we did them live on LinkedIn.
That was really fun to bring people together that didn’t really know each other but had shared values because if you’re on my podcast, you probably have a set of shared values and I just let them go and let them talk. I posed a single question to each of those trios and just let them go after it.
And that was so much fun; to just see them kind of banter and agree on things. So yeah, it’s been a wild ride, pun intended.
Peter
Nicely done. What are you learning as you do the podcast?
Melissa
That we’re not alone. That was my intent and so I’m glad that that’s what I’m learning. In the trailer episode when I first kicked it off, I told everyone that the reason I was starting the podcast was that when I was coaching, I often had people say to me, well, in the real world, that’s nice in theory, but in the real world… And so my intent was to bring a bunch of people on this podcast to prove that the real world is more than you think it is. That people are doing off the wall crazy, amazing, successful things that are bighearted and wild and they’re working. And so I wanted people to feel less alone if they were that person in their organization that was feeling like, “Oh, I want to try something different.” You’re not alone in that. There’s lots of us out here.
So I’m glad that I was right, that I was, you know, that I’ve been able to find guests –that we are not alone. There’s lots of cool stuff happening out there. I think that’s the biggest thing. Yeah.
Peter
You’re doing a lot of keynote speaking now and that’s kind of a different beast from coaching, from advising. What got you into keynote speaking and how do you see it as a different way to accomplish your mission?
Melissa
So how did I get into it? I started speaking at Agile conferences in 2017, maybe even 2016 was my first talk at an Agile conference. And you know, I actually grew up since this is like the culmination of your whole entire life.
You look back and you’re like, “Yeah, that makes sense.” I started singing on stage when I was four with musician parents. I was in speech and debate in high school. People who know me who are listening to this or even you guys, are like, “Oh, this all makes so much sense.” And so when I started speaking, it was really just to give back.
I mean, I had taken so much from the conferences that I had been to, and it had shaped my career. And so, you know, I wanted to share the things that I was learning at the time. And then I just began to realize what a connection you can make with people that you don’t see every day. And how this was really the combination of my one-on-one work, but then reaching a whole bunch of people at the same time.
I mean, it’s very similar to the podcast, right? The things that I speak about are things that are intended to help people feel like they’re not alone, that they are not (you know) wrong or crazy for thinking that things could be possible. And I don’t know– actually, I think it always comes down, for me, to helping people feel like they are not alone. I actually went to lunch today with one of my folks from Scrum Alliance and he asked me what mattered to me when I was in that role as a leader. And I said I wanted to be the leader. That in some areas I had and in some areas I didn’t have, I wanted people to not feel alone.
And so if I can talk about things like the importance of context and clarity and it can help people in the audience to either as an employee go, “Yes, I need that” or as a leader to go, “Yeah, I can give that. I just need to know how. and I need to feel like I’m not kind of like out on a plank by myself trying to do that.”
That’s what I want to do. So it’s this extension of the one-on work that I do, but in a much bigger way.
Richard
What are some tips or advice you have for other people who want to get into speaking more, like you’ve done?
Melissa
Ooh, just do it. And I know that sounds so, like, there’s that word “just,” I know, right?
I used it. But we’ll use it in like the Nike sense; like you can do it. “Just” says you can do it. There’s kind of two parts to getting into speaking. One is the actual speaking part. It’s developing the content, getting up on the stage, and having a message to share. And the other part is convincing people that you are someone who should speak
And so it was quite funny because when I first started speaking, I submitted a whole bunch of calls, you know, call for speakers, a whole bunch of submissions to different conferences. And one by one they were getting accepted. And I had only spoken at like one conference at that point, like this is way back in 2017.
And I had a friend say something silly, like, “Oh, you have the golden touch. Everything that you submit is getting accepted.” And I was like, you realize it doesn’t mean I’m a good speaker. It means I’m a good writer; because my submissions were good. “And you know,” I went on, “I hope to prove that I am a formidable speaker.”
But at the time it was all about having clarity of message. And if you can clearly convey your message on paper, that’s at least half the battle (now that I’ve also been on program committees). If someone can convey on paper, then at least you know they have clarity of thought, and then can they take that clarity of thought and put it on the stage?
So it really does require both. I mean, it requires you to be able to convey that you have good ideas, they’re clear, and I can get on stage and share them succinctly and help people in the audience to take away something from that message. So, um, focus on writing and focus on speaking and start small.
Like, I mean, my very first talk was at a– I joke that I had to go all the way to Canada at that point to get my first talk– because I spoke at a user group in Calgary, frankly, because I had a good friend who was one of the organizers of that user group. And so he’s like, “Hey, if you’re willing to come visit, you can share about mission, vision, values at this user group.”
And so it’s okay if it starts with 20 people. Start somewhere. Talk about something that you’re passionate about, and again, have clarity of what do you want people to walk away with? What do you want them to be inspired by? And focus on that. Cause it’s really easy to just write an hour’s worth of stuff to talk about.
But what’s going to matter to them and what matters to you? Because that’s what’s going to allow you to really, passionately speak about whatever that is.
Peter
I would even emphasize that people might benefit from speaking at smaller groups first, [Richard comments, “I recommend that.] because I recommend that when we’re developing new skills, there’s this rule that comes from the research on flow states that you get into a flow state if something is about 4% harder than you feel comfortable at. Right? So you need to stretch a little bit. But if I haven’t spoken before and I get accepted to do a 2000 person keynote, the stakes are so high that it’s probably not going to be a great skill development experience for me; whereas speaking in front of 20 people is a stretch, but it’s not like it’s going to make or break my career. I’m not like standing on the TED stage, right, where it’s like, if this goes well, I’m a superstar, and if it doesn’t, I’ll never speak again. The stakes are just too high. So I think that there’s something in that, and the other thing that you do really well, and maybe even intuitively, that I’ve really learned over the last few years as I’ve spoken more and more is tell stories.
If you don’t have stories, like personal stories for every point you’re making, it just is not that interesting to say, here’s an interesting model and let me explain logically why this model makes sense. It’s like, what’s the story behind the model? What’s the story on that part of it? And you’ve gotta find your stories.
Melissa
Absolutely. That is why I will always coach, you know, my speaking career is growing and I’m being asked to do more and more, and I love it. Again, to me it’s a culmination of a lot of things that I love, and getting my message out to a broader audience. But I will always coach because I never want to be that person who coached five years ago.
And I’m telling stories from back when the iPhone 11 was out and now we’re on the iPhone 16. And you know, I mean, you want to be current and be telling stories that matter now, and you can’t do that when you are so siloed off into only speaking. So I’ll always coach. I have a very quick, very funny story about my second talk, just talking about small groups.
My second talk was also at a user group, but here in Denver, same talk. I’m doing mission, vision, values. I’m super passionate about that. Still am. I’m giving this talk and the room is in a large U-shape. There are probably about 20, 25 people in the room, maybe more. And there’s this woman at the back of the room and the entire time that I’m talking, she is sort of like glaring. Like she’s like squinting her eyes at me and I am convinced–now I am one of these people that really, really reads the room whether I want to or not.
I’m just very aware of people’s faces and I am convinced this woman hates me. I am not kidding. I’m like this woman, why does she hate vision statements so much? Why does she hate me? Like what is going on? Is she just glaring? I finish the talk, everything’s fine. And she comes up to me afterwards and I’m bracing myself.
This woman is about to scream at me like, what did I do? And she asked me to go to coffee later in the week. She’s like, could we go out for coffee later in the week? And I’m like, “Are you going to kill me? Um, sure.” And she said, “I really loved everything you had to say, but I didn’t bring my glasses so I couldn’t see all of your slides; but I would really love to talk more and, and learn more about what you were talking about because I couldn’t see all of the content.” The woman was squinting because she couldn’t see, but I was convinced that she hated me. And so a cautionary tale: It is good to read the room. That is a good thing and a thing that most of us do sort of inherently. But don’t write too much of a narrative in your head about what people are thinking, because often you only know 2% of it, and they might have just left their glasses at home.
Peter
I’d love to know, what do you hope work looks like a generation from now?
Melissa
Do you have six hours?
Peter
Sure I do. I’m a night owl.
Melissa
I’m so excited by this question. Okay. I’m going to answer your question with a quick anecdote, and I don’t mean to be pitching, but there’s a talk that I give called “The Truth about Agile” and I start the talk describing how my husband’s classroom looked.
My husband was an 18 year English teacher and his final five years, he used Agile values and principles and a lot of scrum practices in his classroom. And I start by telling the story about these kids. These are 15-year-olds, and they come to the room excited. They had done sprint planning earlier in the week, so he didn’t even have to say, “Here’s what we’re going to do today,” because they already knew.
They go into these teams. The work to get there was not effortless. But at the point that I am describing this classroom, work was effortless. These kids had all of the things that I talk about, context, clarity, choice– they had those things in their classroom. And I use this to lead into talking about the Agile values and principles because it is the purest application of those values and principles that I have seen.
And then I end the talk by saying, we have some work to do because these kids are in high school right now. By the time they reach us– to your question, Peter– we have a lot of unlearning to do and a lot of learning to do because they are going to have certain expectations about what work looks like and it all does come down to autonomy.
I mean, let’s quote Daniel Pink; autonomy, mastery, and purpose. These kids have that expectation. My 16-year-old daughter is not going to walk into a traditional workplace and just accept it. And the funny thing is, we have done this to ourselves, and I mean that in a good way, but I remember my parents telling me I could be anything I wanted to be.
I remember my parents telling me to work hard but stand up for yourself and don’t let the man get you down, blah, blah, blah. And so, of course, the children of those parents are going to teach our kids even more of that. And so we don’t have a choice but to change the way that we work. And I think the pandemic accelerated that in a big way because it actually forced some of these things to come to fruition by necessity.
And so I think we’re going to see workplaces that are a lot more entrepreneurial in nature. Where here is the mission, here’s what we are trying to accomplish, but there are many, many ways to get there. And I want to activate your entrepreneurship in this organization. And I want organizational cultures and structures that support it.
My second guest, Dr. Allie Hill, used a term that I’ve been using ever since, which is “workplaces should become these entrepreneurial networks” where I bring what I have to bring to the table and my ideas and creativity and you bring yours and we figure out how to collaborate and cooperate in that way.
But no one owns us. And, you know, we are all sort of working toward this common goal, all of which we’ve been talking about in management books for years, but we don’t actually do. And so yeah, I think that’s where we’re headed. And before, in the before times, it was a nice idea. Now it’s a necessity.
I don’t see another way around it; because the workplaces that don’t work that way eventually are not going to get anyone to work for them.
Richard
Melissa, thank you so much for spending this time with us. So much good stuff. Where can people go to learn more about what you’re doing and connect with you?
Melissa
I have a website (shocker). It’s just melissaboggs.com. Also, I am fairly active on Twitter @MelissaDBoggs. And you can always email me at melissabogs.com.
Richard
Listen to the podcast and the show. Yes we’ll link to your website and the show and your Twitter account on the show notes so people can go to all those places.
Richard
Thank you. It’s been a pleasure.
Melissa:
Thanks guys. Always a pleasure.
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