Rusty Gaillard  0:00  
As a leader, if you do not have a high performing team, you are the one who suffers. I'm Rusty Gaillard, and this is do something different. I am super excited to have with me today. Eric Bensley, Eric is the head of Global Product Marketing at Asana. When he and I first met, he was a VP of Marketing at Salesforce, and we met because he wrote about being an introverted leader and the nuances of that. But we're going to talk today about how do you build your team so that all the weight is not on you, that you can rely on your team to be effective and to deliver So Eric, welcome. I'm super happy to have you with me.

Eric Bensley  0:38  
Thanks, Rusty. Appreciate the opportunity. Yeah,

Rusty Gaillard  0:42  
great. Well, hey, let's jump in, because this whole topic came up because you and I met for coffee a couple of weeks ago, and it was just a handful of days before you guys had a big product launch, and you made a comment to me. You said, There's no way I could be here if I didn't fully trust my team to be delivering and executing on this. And I'm just curious, how much do you depend on your team? Like, how much do you trust them?

Eric Bensley  1:06  
Yeah, a lot. I think trust is a big one for me. And, you know, you've, you've probably heard the the, you know, the adage that trust takes forever to build and a moment to break. We've all heard that one, which I think is a little maybe a little bit too scary. It shouldn't be as scary, but there's some truth to it, which is, I, I look to people to consistently deliver and communicate to me, to build that trust, right? And once I have that trust with somebody, I, you know, I trust them implicitly. I, and I've done that, I feel like I, I try to create those relationships with the people on my team, where, where we have that trust so we can operate, and I can depend on them for for more I don't have to be as involved. I've, I have to say I've known managers that have been extremely hands off. And I think that can be, that can be a negative if, if it's, if it's done just as, hey, I trust you, you can do your own thing. I think it's, it's that middle ground. It's not just hands off. It's knowing that they're going to come to you, be proactive, give you the updates you need and that they're never going to, you know, hide any information, do anything that may be outside of, like what the business needs, without kind of going to you first. So like that, trust, to me, is really the core to it. And and with my team, especially currently with the team that I have right now. I depend on them for, for everything, and most of that stuff, I would say at this point I don't have to be involved in.

Rusty Gaillard  2:50  
I mean, that's amazing. And the visual that came to me is climbing a ladder, right? You're at this point where you rely on them, you trust them implicitly. You don't have to be involved in a lot of things like, that's kind of like the top of the ladder. Yeah, you come into the job, you're at the bottom of the ladder, right? Because you don't know the team. You're just building relationships. You're building that trust. How do you think about the stages of that, or the rungs of the ladder? Are there different levels? Do you think about it in that way, or do you think about it as just this continuum, and you're building trust

Eric Bensley  3:18  
as you go? Yeah, in terms of independence, I kind of, I think of work in two rough buckets to start. I think of kind of run rate work or operational work. And the easiest way to say that is like, it's work we've done before. And then I think of new work, new creative so like, roughly speaking, I think of those two bodies of work. And I think folks earlier in their career, and myself, included, earlier in my career, I was really good at executing the run rate work really well, really efficiently, and I got a lot of trust over time from my managers to kind of do that type of work. I think breaking into sort of the independence on like the new and big and change and meaty stuff, that's where the leadership really takes in. And I think that's honestly where it takes more time to to build trust, because that's the big for me, that's the big kind of stage in growth when I work with individual contributors is, you know, it's not easy to get to a place where you can execute on run, rate work, and you can do it well, and you have the, you know, you have the description, and you, you execute it, and you, you do it well. But I would say that it's easier than the next phase, which is in ambiguous situations where you're trying to change the way something's done. Who do I need to check with? How do I present this, how do I move it forward in a meaningful way, building trust in that environment I feel like, takes the most amount of time, and so like, that's the bigger stage of growth that I that I see, and that I honestly, I like working with people,

Rusty Gaillard  4:55  
so I can think about approaching that stage of growth from. From the individual contributor standpoint, or from the manager standpoint. And I'm curious from a manager standpoint, because hopefully individual contributors are motivated and they want to grow, they want to take on that kind of amorphous never done this before, kind of work, but as a manager, how do you guide them in that process? How do you set expectations with them? How do you communicate the way you want them to engage, like what's an appropriate risk to take? How do you build that trust? It's you're you're trying to guide and steer that process as a manager. And I'm curious to know what has worked for you, or what approaches do you use to stay plugged in, to communicate, to help a person start to build that trust and capability to take on this new kind of amorphous work?

Eric Bensley  5:41  
Yeah, I think it's not as easy as as the individual contributor work, right? Like there's not as there's not as much of a playbook, but I think the the kind of the soft skill set that I like to teach people is, is sort of anticipating questions from other stakeholders, right? I think that's a big kind of move for getting to a place where people trust you as a manager of work. And that's not, it's not necessarily something easy we're used to. Like, here's my list of things I have to do today. I'm going to do the next what I what I talk a lot about, is, like, who needs to know about this work? When do we need to inform them? What's the work? Back plan on that. How are we going to review the the information before it goes to these stakeholders? Who else needs to know about this? It? I think it in its kind of most basic form. Some people call this like internal brand building, but I think of it as more kind of like internal trust building, where you're essentially, you're you're you're getting folks around an organization and even externally, to trust that you're thinking about the needs beyond yourself, right? What does the business need? What do customers need? And that's it's a harder process, right? Like it's not just waking up in the morning going here my five tasks. It's looking at the work that you're doing, and thinking about all the considerations that might happen across stakeholders, across your customers, across everything, and anticipating those needs, and in a perfect world, starting to answer those questions before they're even

Rusty Gaillard  7:12  
asked, yeah, yeah. I think about this as I often talk about a delegation like spectrum, and one in this spectrum, you're delegating tasks like go do this thing and come back to me. Then you move up the ladder, or move across the spectrum, and now you're delegating projects, which is a series of tasks, and that's more like the day to day execution work, right? You know what needs to get done? It's these series of things you can delegate that to go get done. What you're talking about is a new level, which is delegating a project or a goal or a direction, and it's amorphous. There is no project plan. There's no clear set of stakeholders. Even sometimes it's just, hey, you need to go accomplish this. So when you're working with someone to become more independent in that area, what is your method for staying connected to them? Do you have specific expectations around I want to meet with you once a week. Do you have toll gates in the process? You want to check with them, like, is it more ad hoc? I'm just wondering how you think about it as a leader trying to get someone to be able to handle and navigate and plan and successfully execute one of these amorphous projects, or amorphous goals that's not even a specific project. How do you support them? And how do you like to engage with people as they're doing that?

Eric Bensley  8:22  
Yeah, absolutely. Well, I think it depends on kind of where someone is in this process, right? I think to start if someone's sort of getting their bearings in this world, I kind of, and this is something that I would say is a principle that I carry across multiple things. I just like to get in it with them, right? As opposed to sort of trying to give, you know, principles or how to think about it, I like to get in that, like, early kind of thinking stage and, like, think with them a little bit. So it's so break that down a little bit, because it's like, are you thinking for them? Are you thinking with them? Like, what does that look like? Yeah. So I think you know, if we take a project, let's say we're trying to launch a new product, right? And we have three or four months to put together a plan. It starts with just some questions around, you know, what? What is it? How does it work? Like, let's say it's a product. Who is it for? You know, all the typical like, those are more marketing questions, right? It's, it's, it's, ultimately, how do I get to sort of a positioning statement for whatever, whatever I'm doing? Who is it for? Why do they care? You know, all those things, right? The dorky marketers, maybe that are listening will care about that. But then, like, after that, I think it's more about, like, how we're going to get there, right? Like, what are the, what are the big stages? And I think that's where, you know, I like to kind of open that up and get, you know, the individual, to start thinking about the path to this ultimate launch, right? What? Are those milestones? What are those gates? What do we need to do? And then, you know, obviously, no one's gonna be perfect doing this, like early on. And so there's some calibration there. It's like, oh, well, we should. We need to talk to the CEO. Well, who do we need to talk to before we talk to the CEO? You know, that's sort of working back and ultimately, trying to get to a place where it's not like, here's the template for launching the product. It's more like here, here's the thought process to get us to a place where we can get sign off, where we can get to something that's going to impact the business in a positive way. And then I, you know, it takes a few of those to really get to a place where it's like, okay, they kind of get how to do this, and it's more they're just going to keep me updated. But for me, I just like to kind of start off thinking through it with them, right? Versus just saying, do the thing, come back with the thing, because that can be intimidating, right? Especially if it's like, the first time. So,

Rusty Gaillard  11:01  
so tell me about a meeting like that, and the balance between telling versus asking. We were chatting about this earlier, right? Like, I think as managers, we're all biased towards telling, right? Someone comes with a problem, our first thought is answer the problem or give them the answer. But there's a lot of power in asking and the getting them to think through it and and so I'm just, I'm curious how you balance asking versus telling when you're in one of those conversations with someone where they're a little unclear and you're wanting to guide them,

Eric Bensley  11:32  
yeah, I think you have to start with a decent amount of telling, just to reassure somebody, especially if there's they're kind of leaning into an area that they haven't been in that many times, that you're, you kind of know what you're doing, you, you, you got their cover right? So I think it's like, I try not to, like, start with questions, because then it kind of feels a little bit more like you're, you know, putting them on the spot, versus, like, trying to coach them. So I think it's like, like, here. Here are kind of some principles of a project like this that I've seen successful, and then kind of using more of a framework to do like discovery underneath, so it's not so intimidating. And for a product launch that could be okay, here's our product launch. Here's the date we usually have to have materials locked and finalized. Here's usually when we think about briefing like the broader executive team on the plan, you know, so there's at least some tent poles in there, and then we can start to sort of break down underneath it. Say, how would you think about getting to this milestone? So what do we need to do? Who are we working with? What's the team look like. And the questions, I think, are, you know, to your point about kind of like, like tasks, all the way up to like projects, goals, like all that stuff, starting more in the middle, right? So you're not starting at the top and saying right out of the gates, how much revenue should we deliver on this launch? You know? I mean, that's an intimidating question to start with, versus, you know, we probably need to get sign off on the name of this thing if it's happening in three months. Like, how should we go about researching that?

Rusty Gaillard  13:14  
Yeah, I love what you're breaking down, because what you're what you're describing is you're not asking someone to do something, or quizzing them, or asking them to come back with a solution on something they've never done, and they don't know how to approach. And so you're trying to break it down and to say, like, let me give you some structure. Let me give you ways to think about it, because I've got more information than you do as the manager, let me give you some ways to think about it. And then as you start to break it down, you break it down into chunks that they can then take and go manage on their own, and then you can start asking them questions about those chunks, but you've got to teach them before you can expect them to do it on their own. And I love that approach. And frankly, as a you know, we're both parents, and it happens in school, right? It's like, before you get the assignment to go do this kind of next level math problem. Someone teaches you how to do the problem. And so what you're describing is that same dynamic. It's like, in order to elevate someone, you need to teach them and support them

Unknown Speaker  14:10  
both. Yeah, absolutely.

Rusty Gaillard  14:13  
So we're talking about school, and then kind of logical finding thing is like, Okay, well, what did you get in school? What grades did you get? And so there's also that equivalent in work. It's not necessarily a grade, but there's this, you know, in one of these projects, where you're wanting to, wanting someone to grow and elevate to the point where, as you described earlier, your team is full. You fully trust them. They're fully independent. They can go execute on these projects with minimal intervention from you. But as you're on that journey, how do you how do you keep high standards and like, what do you do if someone brings something back to you that's in your mind is not the way you would do it? How do you make that assessment of, is it good enough for me to let them run with it, or do I need to change? Like, how do you manage that, that question around quality and standards?

Eric Bensley  14:59  
Yeah. Yeah, and to answer this, I'm thinking more in the sort of the new work create like category versus like the execution, run rate stuff. I think there's a few things. The first one, which I've kind of already alluded to, is, like, as a leader with that type of work, I never like to leave the kind of the trenches of the work. So like I I like to be in, in in the work, working with them, so that I'm not sort of falling out of, like, the standards of the team, if that makes sense. So like, I expect a high standard. I also like to show up and and show up in those forums as creating at a high standard as well. I think one of the things that you know, some leaders can create blind spots on is when they sort of think they don't have to be part of the work anymore, and they're just sort of guiding the work. And that's, I think, a recipe for, like lowering standards, because once you aren't setting a bar for your team that they feel like is aspirational. I think you start to lose that standard, and you go to like, you default to whatever the standard is created by the team. So that's like, one thing I like to do. I'm always hands on with the work, and I, and I, I really do like what I do. And so that's why, you know, I do have high standards for it, because I I want to create good work, and I also just love the discipline of marketing and what I do, I think the the other thing that I really like to do with my team is let them showcase their work to other teams that actually give, you know, dynamic feedback and aren't necessarily thinking about, you know, pulling punches, necessarily, they're just trying to get to better work, right? It's one thing for me to sort of sit in the, sit in a room and say, you you know, this headline would be better if it was this. Or, you know, have you thought about this? I I like for them to experience kind of a lot of different stakeholders and perspectives that sort of ground us in these standards. Why does it matter? You know, it's it shouldn't be because Eric cares about it. It should be because it's going to have more impact at the event that we're doing, it's going to help with revenue attainment for the play that we're launching. And so I always like to, obviously, like, stand behind those folks while they're doing it, but I don't like to save folks from feedback across the organization. I think that helps them see why the standards matter and why they're there, and then sort of become self motivated to align to those standards, as opposed to, hey, my boss said it needs to be better. And I think the other thing is, which I really enjoy doing is just showcasing good work, right, giving examples to my team. I also I kind of brag like, think of my mom when I say this, right? Like I brag like a mother when work is really good, and I'm not shy about it, sharing it with other teams. It's like, this is what really good product marketing looks like. And it's partially because I want to acknowledge what my team's doing, but also partially because I want folks to be like aspiring to create good work and have that sort of intrinsic motivation. And I think that happens when others are are sort of admiring your work. Yeah,

Rusty Gaillard  18:27  
yeah. That's great. That's great. What I hear in that is like, also not being afraid of the natural consequences of somebody owning their work and carrying it forward. And that's what you described about getting feedback from other parts of the organization. It's like, it's not just you who's providing feedback, but they're owning the quality of their work. They're standing up and presenting that to other people, and they're gonna get feedback on that, and that naturally is gonna encourage them to elevate their standards. Yes,

Eric Bensley  18:53  
one thing I would add to that, which I struggled with for many years, is it takes vulnerability to the leader, to elevate people like that, because I think the reason that most leaders hide their people is because they want to control the narrative of what's going on on their teams, and so that comfort to be able to share that and know that you can navigate if It goes poorly, if it goes well. That's taken me a long time to get comfortable with as somebody who, you know is, is a perfectionist, you know, by background and and that. But it's also like very it's a big unlock, or it has been for me to sort of feel like I can do that and and not actually in service of the people that are trying to grow in their careers, that I'm doing what's right for them and I'm also doing what's right for myself.

Rusty Gaillard  19:50  
Yeah, I mean, which brings me to the last question I wanted to ask you, which is, you know, what you described as a little bit of a recovering perfectionist, and the vulnerability? It takes to showcase your team and put them in front of people without being 100% in control of the narrative. And I think that also reflects on the leader, and a lot of people are concerned about that. What if my team drops the ball, then it looks bad on me? So there's multiple levels of vulnerability and being, quote, unquote, out of control in a situation like that. And I'm curious for you, when you let go of this idea of control or perfectionism, like, it has to be just so when you let go of that idea, what did you replace it with? Like, what was your new thought or goal that you were aiming for in those kinds of situations? Yeah, I

Eric Bensley  20:35  
think I did change, like, my North Star of like, why I'm doing what I'm doing a little bit. I think early in my career, it was about showing success, you know, and it was very selfish, you know. And I think that's, that's like, I can say that now, and it's not a bad thing, right? I think that's how most people start their career. They're trying to grow their own wealth, their own credibility, their own impact, you know, their own image, right? A lot of us care about the way titles look and the way our family and friends think about what we do, and that's super important. But the switch to manager, and, you know, it sounds kind of like intuitive to say, like it has to be about it has to be in service of other people that you're sort of doing it because if you, if you were just thinking exclusively about like your own brand, then the best way to do it is to control that, right? And that's and that's what you do when you sort of hide your team. For me at this point in my career, what gets me going is not launching another product. I've launched a million products at this point. I haven't launched that many. Just a footnote. It's, it's the ability to sort of help other people find their passion, like like other leaders did for me and so so for me, what I'm telling myself is not like, Hey, this is going to make me look even better, it's, it's that this learning is going to potentially help this person unlock, kind of a learning that will help them to expand, like what they can do with their career, help them see things in a different way. And when it, when I think about it like that, it's just a calculated risk, right? Like I know that anything that sort of goes differently or out of my control, I can work with other leaders. I can work with, you know, I can figure it out right, and I'm willing to, I'm willing to live with that, because, at the end of the day, like what I'm doing, what what I'm passionate about in my career now is figuring out ways to help others kind of unlock their path, like leaders did for me in my career.

Rusty Gaillard  22:51  
Yeah, beautiful. And I want to just add to that, when you do that, your life also gets better, because that is how you develop a team that is fully capable, that you can fully trust, because you just said, the opportunities for them expand their capability expands. You're investing in them. They're more satisfied. Your life as a leader gets better, and it gives you the opportunity to elevate what you're doing, because they're elevating the level of work that they're delivering. So it's, I just want to add there. It's like a lot of people don't necessarily recognize that, but it's a willingness to shift your focus, to tolerate the vulnerability, to let go of some control that helps your team Elevate, helps them be more successful, and ultimately helps you. Yeah, Eric, this has been fantastic. Thank you so much for joining us. I know you're on and off, sometimes on LinkedIn, not often on LinkedIn, but if someone's like man, Eric's the bomb, I totally want to connect with him. What would be a good way to do that? Yeah, LinkedIn is great. Okay, awesome. All right, Eric, thank you so much for joining today. Thank you rusty, thanks for listening to do something different. Make sure to SUBSCRIBE, like, comment and share with your friends. You can also find us on your favorite podcast platform. If you want additional content beyond what's on the podcast, make sure to follow me on LinkedIn and on my website, rustygaillard.com