Stepping Into Transformation: Lessons in Designing Management Training That Sticks

I feel like I kind of knew it. But I was maybe denying I was a little bit in denial that I was the type of person who feared conflict. I mean, I grew up playing, I was the CO captain of my football team. I’m six feet 290 pounds, like I’m not like a small person. And I feel like I could kind of hold my own, if you will. But in reality, there was four, when I saw this thing about that I scored higher on avoiding conflict, I really had to think about, actually I do, and there are little ways that I can get stubborn or that can be passive aggressive, and how I handle interpersonal interactions. Sometimes in a first I felt like that kind of didn’t feel great. But the more I learned about it, the more I realized, I’ve got natural strengths that relate to my fear of conflict, things around being a great mediator, I can mediate conflict, being a great listener being just a friendly, kind person, wanting there to be harmony amongst a team. A good harmony, like harmony, as in, we’re all working well together toward mutual outcomes. So yeah, it was definitely something I had to embrace and learn how to navigate. This is

Aydin Mirzaee  07:34

really interesting, because especially in this case, you’re saying that maybe you could have said that I knew this in advance, but it was really the test that made you think about it. And then as you thought about it, you may be kind of leaned into what it actually meant. So for people out there that maybe have an inkling that this is an area of strength and weakness at the same time, every characteristic has a little bit of both. What are some of the symptoms? Like how did you know that this could be something that is true? Like are there situations that would happen, that you think that really validated for you that conflict might be something that you avoided, when

Justin McSharry  08:13

it came time to have a difficult conversation with maybe an underperforming team member, maybe even friends and family members outside of work, I would always get very uncomfortable, I would feel a lot of kind of flushed and my head and my face, I would find myself squirming out of those situations, through humor or through things would after a while be left unaddressed, and they would fester. And in the case of an underperforming team member, it’s got to be addressed. At the end of the day, the guy attended a workshop once where the advice given to me was to be really successful in life and especially to be successful interpersonally. And to really be growing as a human being basically you’ve got to embrace discomfort, and they framed it in a way where it’s like you actually are not growing, you don’t know that you’re actually successful until you’re feeling discomfort. So discomfort, it’s actually a good thing. Discomfort is something that tells you that you’re actually growing and ultimately that can lead to success in business and life. And so that was a good reframe for me. Once those feelings of discomfort started coming up, instead of shooing them away. I was sort of like, okay, I guess I’m onto something here. And I guess I have to just learn how to be in this messy, uncomfortable moment and just get better at it. Basically just get better at it and find the right words to use and maintain a level of respect and kindness at the same time and compassion and it just takes a ton of practice. I just had to have a lot of difficult conversations. It was

Aydin Mirzaee  09:46

almost like you notice when you have those feelings and almost reframe them and use them as opportunities to actually grow in those situations and maybe Dare I say look forward to them when they do happen in history. Andre,

Justin McSharry  10:00

I have found that that formula of embracing discomfort has led to growth and success for me. So

Aydin Mirzaee  10:06

is this something that you use the help of an external coach to be able to resolve? Or is this something that you were largely able to work on through self reflection?

Justin McSharry  10:16

I definitely have you used coaches and use coach on this particular issue. I leveraged my previous leaders, managers who were good at this, I found people who are really good at conflict too. And I would just ask them, how do you, I remember talking to a friend who actually kind of loved conflict and watched how he would handle it, what he would do? And so it was a combination, for sure. But I definitely embraced feedback and coaching. Yeah,

Aydin Mirzaee  10:42

and so you’ve also worked with a ton of leaders, we’re gonna get into learning and development programs and how you train others at large companies. So for the person that actually likes conflict or leans into it, what is it? What frame of reference or like way of thinking do they have what makes them like it,

Justin McSharry  11:00

I remember talking to a friend of mine who liked it. And he said, when he was leading a sales team, and for him, it was like, I just need to know what’s happening, right. In order for me to hit my number of recorder, I need to have the absolute truth on the table as to like how the deals are going, how the team is doing, what struggles, you know, I don’t want any surprises. So he would then just really kind of probe into situations and maybe even areas that might be uncomfortable, because he wanted to see where things stood. He also had this thing about, I need to know where I stand, whether it’s a relationship with my spouse, or relationship at work, whatever, I just need to know where I stand. And if I don’t know that, I’m gonna go and find out, I’m going to do a very assertively, and it’s funny. It’s like this idea that does anybody ever like to take an argument with your partner, whatever our best friend, like? Does anybody ever love doing that? Or look forward to having a really uncomfortable argument? And the answer is usually no. But then if you ask, after an argument, like a healthy argument, not one where it was very unhealthy, but after a good healthy argument, did you feel better? And usually, the answer is yes. So it’s just remembering that yeah, kind of go through a little bit of heat to get to a good sort of mutual outcome and a strong relationship.

Aydin Mirzaee  12:16

And definitely a really, really good story there. It seems that sometimes in services, almost like a higher order purpose, maybe it’s truth seeking, maybe it’s something else, maybe to get to a better outcome, clarity, that sometimes you have to use other tools. And so when you think of it that way, then it’s almost like something that just needs to happen. It’s almost a part of the process. I wanted to maybe dive into some of the because you currently run a bunch of different interesting programs at Dropbox. And one of the things that you have is something called a hippo development or high potential programs. sounds super interesting. And I love the acronym. What is this program? And what kind of things do you all do with this program?

Justin McSharry  13:03

We call it hypo. Or also we tend to call it stands for high potential. But honestly, that name has gotten a little bit contested, I would say, recent in recent years, what is high potential? What does that even mean? It just because one person’s high potential, this is another person not. So we’ve actually started calling them accelerator programs. The idea of an accelerator program is we want to build a bench of future leaders, right. So as a public company, Dropbox has a whole has to look for name successors, ideally, right. And at least for the C suite. Even below that though, we want to have a pipeline of leaders that succession strategy that is feeding in new internal leaders, so that we can be promoted leaders into more senior positions instead of hiring out all the time. So we have two main accelerator focus areas. One is the Senior Manager population, which would be cultivating for later director positions. And then we have a director, Senior Director, population that we’re cultivating for future VP roles. Each of those programs has a fairly heavy investment, because you know, we have important goals around building a strong potential leaders. So and I can give some examples, if you like of like how we develop leaders in those programs. Yeah, how do you do it on the senior manager front, we call that program has sent we bring a group of about 20 to 25 leaders together into a cohort for about six months. And we start with a two day intensive, bring them all together. And to start, they receive executive coaching. They then go into this two day intensive program where we talk about T shaped leadership, you know, what does that mean to lead across and down into your team? We talk a lot about stepping up being able to zoom in and zoom out and step up on the balcony. At the senior manager level. I find that people are just learning more and more to be strategic. Right and you’re not just leading a team, you might be leading a couple of teams or teams of teams. You’ve got to be able to get up on the balcony and see the bigger picture and see how your strategy connects to the bigger company strategies, and then be able to communicate and lead down into your teams. At the director level, that’s even more important, but that’s starting to happen at the senior manager level. So learning how to get on the balcony is an important skill, we also use peer coaching quite a bit. So we find that when a manager can bring a thorny situation into a trusted circle of peers, and get some coaching around that, it can be a huge unlock for it, sometimes they bring issues that they’re not maybe super comfortable bringing to their manager, or they don’t have a coach yet. And we want to, you know, just get them going ability to share with each other. And we find those super, super valuable. One of the things I’ve been very blown away by is the level of vulnerability that people in these cohorts will bring. And when they can just show up as their human selves, messy mistake making humans, they just get a lot of value from the relationship building they get. And this the mutual support that they get. And we find, sometimes, and they in the program closing there are many people shed tears, it’s like there’s lots of growth happening through those experiences, while driven by vulnerability.

Aydin Mirzaee  16:20

Hey, everyone, just a quick pause on today’s episode to tell you about a new feature that I am so excited about, we’ve been working on this one for quite a while and excited to announce it to the world. We’re calling it meeting guidelines. So there’s all these things that people already know they should do when they organize a meeting. So for example, you should make sure that you shouldn’t invite too many people or if you’re booking a recurring meeting, you probably want to put an end date on that meeting. Or if you’re going to invite someone to a meeting, you should probably you know, if they have more than 20 hours of meetings that week, maybe be a little bit more considerate, and ask Should I really invite that person to the meeting. So there’s a bunch of these sorts of things that you might even know about. But what happens somehow in larger organizations is that people forget all of these things. And so that’s why we built this feature called meeting guidelines. It’s super easy to use, it’s a Google Chrome extension. So if you install it, what will happen is it will integrate with your Google Calendar. And that way, whenever anyone within your company is about to book a meeting, these meeting guidelines will show up and make sure that people know and take a second look at that meeting that they’re about to book and make sure that it adheres to these guidelines. So if you want to book or within your company, have a no meeting day, or if you want to make sure that every meeting has an agenda in advance before it’s booked. So all the different sorts of guidelines that you may want. And they’re all obviously highly configurable, because every company is going to be slightly different. But this is the first time that there is a way that you can get an entire organization to change their meeting behavior. It’s something that we’ve been working on for a very long time, super proud to announce it to the world. It’s called meeting guidelines. If you’re interested in checking it out, we’d love for you to do that and give us feedback, you can get to it by going to fellow.app/guidelines. Again, that fellow.app/guidelines, check it out. And let me know what you think. Dropbox obviously, large company 1000s of people. And so you know, having a program like this makes a lot of sense. But a lot of other companies, even smaller companies can do parts of this too, right? So they can maybe sponsor some executive coaching for members on their team, or the peer group seems like a much more achievable way to bring people together. How do these peer groups run? Do you run them? Are their facilitators is someone volunteer? What are the mechanics of that look like? So if you know someone’s thinking about your their organization, it’s a few 100 person company, or it’s even 100 person company, and they’re thinking, Oh, it’d be really nice if we could use the managers or the leaders of the company in a pure group type format. How would you recommend that they structure something like that? Yeah,

Justin McSharry  19:15

that’s a good question. So I think there are a lot can be done with less resources. I think the way we run those coaching circles is there’s a set agenda, right? So you actually have a group of people, they are facilitated, because we just do that for this program. But you can run them on facilitated, but we give them a structure. It’s basically the person who’s being coached, we call it they’re in the leadership hot seat, and they’ve got an issue that they’re going to bring to the group. They will speak about their issue for two minutes. And we time that, then the rest of the group, this is groups of like four to six people. The rest of the group will then ask questions, clarifying questions for about four, four to five minutes and gain more clarity about the situation. What have you tried, what are some things that are still even though you tried them where you stuck the most, etc. And then for this is the kind of the fun part, then the person in the hot seat will actually turn their camera off because this is all done via zoom. And the rest of the group gets to just share about them and talk about their issue and what they would do for the next five minutes or so. Oh,

Aydin Mirzaee  20:19

so but is that person is still the hotseat person are they still

Justin McSharry  20:24

things off to sort of symbolize that they’re, they’re on the call. But they’re, when we do it in person, the person actually turns their back and around and gets to hear, but it’s really now the conversations amongst the rest of the peers. And you can either give advice, like, here’s what I would do if I were hated. Or you can say, here’s what I’ve done before in this situation. Or you can say, you know, here’s what I’m still wondering about. And all of that’s really valuable information for the person in the hot seat. And they always walk away with at least a couple of nuggets that were hugely, hugely valuable, including just being heard, right, including just being sort of validated that yeah, this is a really thorny problem that other people have faced. So that’s something you can do. Mentorship is something you can do, you can involve other leaders like directors and VPs, and the company to host some fireside chats, we do that as part of this program, and just share their perspectives on certain issues, or bring in elements of the company’s strategy. So we call that exposure, sometimes people just need to hear a little bit more about how the leadership team or thinking about the company’s strategy and executing this strategy than just what you might hear in an all hands meeting. Alright, so a little bit more high touch a little bit more exposure. And so those are a few things you can do without any money.

Aydin Mirzaee  21:39

I really love the format. And it’s super interesting. And to get a little bit more tactical here, too, in terms of the selection of the people, when you think about the four to six people that are in this group, maybe there’s some obvious ones you wouldn’t have? Do you try and have people from like different parts of the company such that they don’t typically interact? Or is there any sort of tips and tricks,

Justin McSharry  22:03

there’s a few couple of lenses we put on it. So the first major lens is that Alan review and the nine box format, which is kind of a classic approach to talent reviews, we categorize leaders essentially into different boxes, or they hire top talent, there’s a few top boxes in the nine box that essentially identify potential future leaders. So we started there. And that’s pretty wide net. From there, we look at cross functional groups, we want to have in you know, engineering, product design, sales, you know, GNA functions represented. After that we also look at geography, and also we looked at were heavy in sort of Imia in Asia pack. And in North America, we’re the heaviest. So we try to do a bit of a balance as much as we can. And then we also apply a diversity lens to it. So at Dropbox, women and underrepresented minorities, which are black and Latino employees are part of our sort of focus groups. So we bring a lens of that into the selection process. So that’s how we put it all together. Oh,

Aydin Mirzaee  23:03

shoot, this is in terms of how you select the people into the program. Yeah,

Justin McSharry  23:07

the 25 people or so. And then the 40 people, yeah, we try to also build some level of cross functional aspects and diversity aspects as much as possible. Yeah,

Aydin Mirzaee  23:18

got it. And so in a smaller company setting some sensitive information will be talked about, because maybe you’re talking about effectively a lot of times management issues are people issues, and so people on the team that other people may know, and I assume there’s some sort of like confidentiality procedure, historical

Justin McSharry  23:39

stays in the circle, your typical Vegas rule. So yes, that’s actually paramount. And one of the things that we emphasize heavily is confidentiality. We also asked them to anonymize so not use actual names, but you can say like a team member of mine, a partner, stakeholder of mine, etc. So we can protect the innocent and the guilty, as it were, this

Aydin Mirzaee  24:01

is super, super helpful. And I’m sure it’s something that everybody can try and implement in their own companies and these peer group format are super useful. I’m a part of a bunch of peer groups myself, and I always find them very, very valuable. And it’s just sometimes even the clarifying questions that people ask, get you to think about something in a different light. And it’s always super refreshing to have other smart people think about your problems. I mean, I think it’s a privilege to be able to do that. It

Justin McSharry  24:30

is important just to have a little bit of light structure, because I think what I found is if you just put together a few handful of peers in a room and say, you know, go ahead and talk about managing, maybe a couple times you do that, and people can self organize and lead that but it kind of falls apart after a while because people go I don’t really know what to talk about. But if you do that thing of like, what’s your struggle right now? Or what’s the blocker that you have? Or what’s the issue, and then the two, five minutes of questions and that basic structure really leads to strong outcomes.

Aydin Mirzaee  24:58

Yeah, so Just building these leadership programs or management programs in general, if you were to say, for example, how different is, you know, management at Dropbox, or when you were at Quantcast or another company, how much of these programs are like very specialized towards managing at Dropbox, for example? Or is like general management practices 80%, the same everywhere 20% different. And for companies looking to build their own management programs, recognizing that management is an important skill in their company trying to uplevel managers everywhere, like how should they think about it? Should they hire an external firm? Should they get everybody to read a book? How should they go about this? Yeah,

Justin McSharry  25:41

it’s a good question. I do think it probably is, like 70%, the same across most companies, and 30%. This is not an exact science, but 30%, where you want to make it bespoke to the company, you’re at the culture you’re at, for example, you just mentioned book, Dropbox is a book heavy culture, our CEO reads a lot. He recommends books, he expects people to actually read the book, if it’s around a certain topic that’s important to the company at the moment. So we’re a book culture, maybe not all companies are right, so maybe not all companies would do books. So there is that aspect of like knowing your culture, or knowing your leadership, and what works. But at the same time, the 70% of what’s the same is, being a frontline manager has many similarities across probably any company you would go to, right? You just gone from ice to a manager, you’re trying to figure out how to delegate, you’re trying to figure out how to give feedback and coach your team, you’re trying to figure out, what do I do for team building, and a lot of those things are going to be similar challenges a lot of employees would face. So what we do is that each of those key transitions, so a transition from ICT manager, transition from leading team to leading teams of teams, so like senior manager, kind of director level, then at the probably like senior director, or certainly VP and above, now you’re leading a full functions, you’ll you’re gonna work at the C suite, the same kind of idea, like each of those has specific transitions that we want to target very specific behaviors and leadership, qualities and capabilities. So we would hold have programming at each of those sort of layers. That’s core, I would say, you know, core programming to support those transitions. And then from there, we do electives, we offer various different ways for leaders to plug in, depending on how things are not at Dropbox. One example is Dropbox, we have the benefit of a lot of people show up for workshops. And if we design a two hour or even three hour workshop, let’s say about mastering influence, that is usually pretty well attended. If you can imagine three hours on Zoom, you know, it’s not a short amount of time. And historically, we’ve had pretty decent attendance for all of our zoom used to be live in person before COVID. But now a lot of it’s over zoom, and it’s working quite well. So we get good attendance at Dropbox, I would say we’re, I’m very lucky as an l&d leader in that regard. And I think a lot of companies struggle with that. Now that said, we are looking to we’ve gotten feedback lately that our business is shifting to be we need to focus on a very specific key areas as a company for the next couple of years. And our, our teams have gotten laser focused on the business. And that’s meant that they do have less time for a three hour workshop. So we’re shifting things, we’re really moving forward in the flow of work as much as possible, which means minimizing the amount of workshop time, additional async learning, micro learning, nudge type approaches to learning, better content management. And so there’s some shifts that we’re making like that.

Aydin Mirzaee  28:34

These are super interesting. And so just to really drive the point home, so in the 30%, of things that might be different. I think this is very important for people to kind of contextualize. What’s an example of something that maybe is different, or something that’s emphasized at Dropbox, but for the management and leadership there, but is maybe not as important at another company.

Justin McSharry  28:55

I would say I mentioned the book one, and even recently drew our CEO and the Leadership Team Read the book zone to win by Geoffrey Moore. And it’s very applicable to a lot of blog organizations. It’s a great book. And we built a whole manager summit on some of the content from that book. And now it’s been applied to Dropbox. And that was an example of something very bespoke. For our company. One of the things we’re trying to do more and more of, because we’re a virtual first company now is more self serve resources. And this is something we’re doing more of trying to gain adoption. So for example, historically, our team development, we do team effectiveness where we help teams run team building sessions or run off sites, a lot of that was high touch. Now we’re going to try to move toward providing toolkits and playbooks for managers to then just take so any given manager could run their own off site and have a whole set of learning sort of team building exercises that could run with their team without a facilitator present. So self serve has become a very important aspect of Dropbox does Design is a very important thing. And Dropbox product, if you’re familiar with it is always been a highly designed user experience. I mean, it’s one of the things customers love about Dropbox. It just works. And it’s intuitive. And so a lot, there’s a lot of emphasis internally on really slick slide decks, right, clean, simple, easy to understand. And so we try to apply that lens into everything we design, as well. So those are a couple of different examples. And then we’re a people centric culture at Dropbox. And so there’s a level of friendliness, there’s a level of relationship and importance. And people want interaction with each other, they don’t want to just show up. And honestly, one of the criticisms we’ve received as a l&d team is we can be a little wonky, sometimes a little framework heavy, both theoretical, and people at the end of the day really want connection, and they want peer learning, and they want an emphasis on relationships. First and foremost.

Aydin Mirzaee  30:55

As we were getting ready to press record, we were talking about AI, and how that relates to learning within companies. And so I know that you’ve been thinking about this a lot recently, what can you tell us about things that you’ve learned or ways that you’re thinking about AI and how it incorporates into what you do? Yeah, so

Justin McSharry  31:16

AI has become a central sort of initiative, AI learning, we have an AI center of excellence that was developed. Earlier in the year, Dropbox made a very intentional announcement earlier this year to become an AI first company, meaning in everything we do, and every product that we build, we are adopting AI as a central sort of strategy, and so forth. And we’ve already started releasing AI based products, and so forth. So we, as the learning team, have developed a strategy around essentially building AI proficiency across the entire company. Now, one of the first things we did was we had to find who are the main audiences, and we ended up with kind of five key audiences, we have product engineers, we have mL engineers, so actually machine learning engineers who do that as their day job. We have product managers who are driving the next generation of AI features. We have GNA, folks, all other non technical, you know, finance, HR, legal, etc, etc, sales. And then we have our executive. So leaders, how should leaders be thinking about strategically leading teams around the future of AI. So within each of those five audiences, and we have goals, right, we haven’t used them on specific topics. So obviously, the technical folks, the software engineers, it gets very technical very quickly. And with the non technical folks, it’s been about more foundational learning about AI, about generative AI. And then another aspect of it is the practice, we need to really learn AI you have to build you have to practice. And so whether that’s an engineer coding it, learning how to develop models, and so on, and algorithms, or it’s a GNA. It’s a legal or finance, or an HR person, learning how to use chat GPT, to accelerate their workflows, we’re really putting together practice labs, and getting people actually hands on keyboard trying this stuff out. And we have our own internal tools that we’ve got people trying out and adopting. And so that’s a big piece of it. And then we’ve also consulted or brought in external learning providers, companies like Udacity, and data camp that we’re piloting right now to figure out how to train engineers and upskill.

Aydin Mirzaee  33:31

Yeah, and what I find really interesting about this, Justin, is that, you know, I’ve had a lot of conversations with pure CEOs, people who run organizations, and there is broad desire for a lot of people to bring more AI into their companies and get people to think about AI first, like the way that you’re talking about, and what’s really interesting about the approach that you all are taking is it almost becomes a broad initiative. And it sounds like you’ve thought about it a lot. It’s you’ve thought about it across the different departments. And it’s not just a thing that just happens because in a town hall or something, the CEO says, hey, everybody focus on AI. It’s a broad initiative requires reinforcement, it requires the tools, and it’s really interesting how the l&d team is like a very strong part of making sure that that happens. So it’s very interesting to see all of that. We’ve talked about a lot of different things today. And lots of different concepts. One of the things that we always like to end on is to kind of get some parting words of wisdom. So for all the managers and leaders constantly looking to get better at their craft. Are there any final tips, tricks or advice that you would leave them with? I think

Justin McSharry  34:41

leading a team is more than just being good at feedback and coaching. I think that it’s also thinking about the entire team and the team dynamics. And so one book that I always recommend is The Five Dysfunctions of a Team by Patrick Lencioni. It’s kind of a classic and it’s been around for I don’t know a couple Like a decade or two, but it’s written in Fable format. So it’s actually a relatively engaging book as far as management leadership books go. And it’s just got a lot of really good lessons for a manager who’s trying to think about getting the team really in a place of high performance and cohesion. And then I think one of the things that I did this made me a better manager, because not only do I lead run an l&d function, but I’ve led teams over 10 years, is, I’m trained as an executive coach. And I remember seeing 80% of the participants of these coaching programs would be other coaches, right, obviously, right, there’s learning. They’re becoming certified because they’re an executive coach as their trade, at least 20%, maybe sometimes more, would be just managers, right, that are never planning to be sort of a coach as a job, but really wanted to be a better leader. And so we’re learning the craft of coaching, I would always submit to really deepen your craft as a manager is less about the functional expertise that you have, and whether it’s sales or marketing or engineering or whatever, but it’s about learning some of the soft skills really, really, really well. Right, learning how to put a strategic thinking and planning really mean what is coaching and establishing a vision, operational excellence. So really seek out those types of learning opportunities. The Effective Executive by Peter Drucker is a classic book too. It’s kind of dry and really antiquated and some of the language but the wisdom and it is timeless. So that’s a classic. And then business books like zoned to win or dual transformation, or the folks at Amazon have written a lot of amazing stuff about how to lead through different processes that has made Amazon successful actually have been quite interesting to read about. And there’s a lot out there you can find. So those are a few things that suggest

Aydin Mirzaee  36:49

lots of great things in there. And lots of great advice. Justin, thank you so much for doing this.

Justin McSharry  36:56

You bet. Thanks Aydin, appreciate the opportunity. And thanks for having me. And

Aydin Mirzaee  36:59

That’s it for today. Thank you so much for tuning into this episode of the Supermanagers podcast. You can find the show notes and transcript at WWW.Fellow.app/Supermanagers. If you liked the content, be sure to rate review and subscribe so you can get notified when we post the next episode. And please tell your friends and fellow managers about it. It’d be awesome if you can help us spread the word about the show. See you next time.