Lynn Winter, Digital Strategist, Founder of Manage Digital

Lynn Winter, Digital Strategist, Founder of Manage Digital

Project management is a unique role, and it takes a unique sort of person to fill it, and do it well. In the digital world, project management is still being defined. Some organizations have a good understanding of what a PM is, and isn't, and others are still figuring it out.

Lynn Winter, a digital strategist, Digital PM Summit speaker and founder of the Manage Digital conference, started her career doing the work that people hated most. Her coworkers sat down and wrote a list of things they didn't want to do anymore, and that became her job description.

After stints at different organizations, Lynn went freelance. She lost 20 pounds, started sleeping better, switched to a healthier diet and saw her marriage improve. Lynn joins us to talk about what it takes to be a project manager, perfectionism and the tendency to put everyone else first—sometimes at the expense of your own health, happiness and relationships.


Join Lynn at the Digital PM Summit, and catch her keynote, “Be Bold. Be a Digital PM.”

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Welcome to The Bureau Briefing. A podcast by the Bureau of Digital, an organization devoted to giving digital professionals the support system they never had. Each episode, we're gonna talk to a member of our community doing awesome, inspiring things. 

Now for your host, Carl Smith. 

Carl Smith: Hey everybody. Welcome to The Bureau Briefing. Today, I have got a digital strategist and the founder of the Manage Digital conference which is a conference for digital PMs in Minnesota, Lynn Winter. 

How are you Lynn? 

Lynn Winter: I'm great, how are you doing? 

Carl Smith: I'm great. And I want to start off by asking you about the Manage Digital conference and what was it that made you do that? As somebody that puts on events, it's like it's such an effort. So why did you decide, I'm gonna do this? 

Lynn Winter: Maybe 'cause I wanted to learn how much time it took to actually [crosstalk 00:01:58]. 'Cause you're right. It is a lot of effort and I thought, "I'm a PM. I can handle this. This will be no problem." But it was a little more energy than I thought. But it had been something I had been thinking about for years. And essentially I think it started really when I went to the second DPM summit in Austin. And it was such a life changing experience for me. I had been working at an agency where I was the only project manager and I was deep into the Dribbble community which is a great community. But at that time there was just no project managers around me. 

So in a field of growing PMs where the role had not been very defined and clear within the industry, and being inside a sub community that didn't really have a lot of project managers I just kind of felt a bit lost. And it was really searching for my people. Like I would literally go to a Dribbble Con and be like, "That one person over there's a PM." And I would like go hunt them down in this awkward way and introduce myself and then hang out with them for days. And I'm sure they thought I was strange. But I was dying for that.

So when I ended up in Austin, I found that experience and it was great. And I've gone to a couple of summits but I wanted to kind of recreate that connection locally. A couple years back I was in a role where I was managing project managers and teams and people would ask me all the time about jobs and how to learn certain things and there's just not a lot of great ways to grow your skills as a product manager. 

so for years I had been thinking about creating a local conference that was something, just small one day conference that was affordable and allowed everyone to network and that was really the main goal of the conference is to bring people together, to have mentors and to be able to connect for new jobs. 

So I had that idea for a long time and I thought, "Oh my God, how am I gonna ever do this?" And then I went freelance and I had time or so I thought for a couple months. But I was gonna do this so then I had to do it even though I had no time and that's what happened. 

Carl Smith: Once you say it, you gotta do it. 

Lynn Winter: I know. There's something about when you put a website out there, then you tell people and then I felt committed. 

Carl Smith: Now you had a small team that was helping you, right? Because I remember I exchanged emails with one gentleman I think. 

Lynn Winter: Yeah. We had a couple people during the time of the conference. A couple people had to step out because lo and behold their PM jobs took over and didn't allow them a lot of time. But it was a very small team that put on all the work. 

Carl Smith: Yeah. Well everything that I heard, they did a tremendous job so congratulations. Out of the gate, sounds like you got a success with Manage Digital. 

Lynn Winter: Thank you. 

Carl Smith: Now one of the things you mentioned is leading straight into what I want to talk about. It's a little thing we call the segue. And you were talking about the amount of time that you had and the amount of time that the other people had. And digital PMs specifically get pulled in such a wide range of directions. And I remember being on a call with the heads of some digital PM meetups and I asked them, I was like, "Can you tell me why you aren't more involved in the slack channels?" And they said, "Well unlike owners, we have to work and we can't just hang out all day and slack." And I was like, "Oh, I have just been schooled." And it's so true. 

So I'm just curious. When you look at digital PMs and what your talk is gonna focus on is burnout. What do you think, besides just the amount of work that can come in, it is, that really can undermine a digital PM in their personal health really? 

Lynn Winter: Yeah. Well I think the way we kind of set up our roles, it's a little twofold. You had a PM that, in general, the personality of a PM is to kind of take on all the extra work. Do all the things and set up everything for everyone else. If you think about it, when people go home, if we don't have something set up for the next day, then we ... The project spends more money, things don't get done, we have to follow up. So the role is really kind of set up where we have to be kind of care taking the garden and then on top of it you get all these people that have a certain personality that really want to do that. That take on too much work, that want to get it all perfect and right. And so you have this clash of a role that's kind of set up for that and a personality that comes together. 

Carl Smith: Right. You're the ultimate blocker, right? If you don't have everybody lined up to work, that just feels horrible. So is that part of what happens at night? It's like this little bit of getting the shakes and you just decide to go ahead and work some? 

Lynn Winter: I think that's really what it is. And I don't think it has to be that way but it's been set up in the industry where it's kind of the fallback take [inaudible 00:07:06]. I mean if you look at a project manager, who's the last one to go out to lunch? You know, who's eating at their desk? Who's not using up their PTO. That role, because if they don't do it, it comes back on them. And so there's not a lot of sharing of that responsibility as much as I wish there could be. 

Carl Smith: Right. And for me, I remember the best digital project managers were the ones who obviously cared. They were really good at what they did. But the real killer attribute was nobody wanted to let them down. 

Lynn Winter: Mm-hmm (affirmative). 

Carl Smith: And that became. When we were looking at digital PMs at nGen Works, at my company, we always wanted those people who were gonna be able to make everyone step up a little bit more and know that they were gonna be as responsible. But it was really difficult to find those people. 

Lynn Winter: I think it is. But I also think there's an issue with creating that culture. So it's nice to hear you say that you're looking for people that would step up the other side of it, but I think what also happens at a lot of places is that there isn't that shared responsibility. There's just like, "Oh, they'll take care of it or it will just happen." I don't know if you've seen this amazing video on YouTube where this man has this magic table and [crosstalk 00:08:38] - 

... have you seen this?

Carl Smith: Yes. 

Lynn Winter: And he puts all this stuff there and it magically takes care of it. Laundry gets fold. He makes mess all the time and it just happens. And it's very funny, but it's kind of how the role works. Things just happen invisibly and it makes things just keep going in a way that, you don't want to change that, you know? You can't change the environment so that that process doesn't keep going, but then it leads to PMs working more hours, solving more things, picking up something that somebody else dropped. 

Carl Smith: And you're also in every meeting, for the most part. So you don't have time during the day to do the work you need to do and rightfully so, digital PMs want to be involved in new business, right? 

Lynn Winter: Mm-hmm (affirmative). And we have to, right? I started getting involved in the sales side to protect myself and the projects and the company. 'Cause what would happen is, someone would throw over something from sales and it would just land on our plate and everybody would be looking at us saying, "How do we make this happen in this timeline?" Or, "How do we do this in the budget?" So to solve that problem, I made my way into sales, and then I found myself doing 25% of sales on top of my job already, right? 

Carl Smith: I'm just sitting here thinking anybody who's listening to this that's not in the industry is definitely not thinking about being a digital PM right now. They're going, "Oh my goodness. That's the worst." What do you think it is that draws people into this job and keeps them there? 

Lynn Winter: Well I do think there is a challenge with keeping you there because I've heard from a lot of folks that have been in the industry for a while just done. Just burnt out, needing to move on and they either step out of the industry or go into another completely different field. But I just think for me, I've always been a project manager from out of the gate. And to me it's that ability to organization, solve problems, help everybody inside and outside. Like all the attributes that make you become the workaholic and the problem, right? But if I can solve the problem and make things run smoothly and make creative things happen but maybe I'm not doing the creative part, that's pretty invigorating to me. 

Carl Smith: So what can digital PMs do if it's within the organization, or if it's something that they personally change in the way that they show up? Like what are some of the things that you've seen work to help alleviate some of this stress and just sheer volume of time that you have to put in?

Lynn Winter: I would say first, unfortunately, I haven't seen a lot of things work. I've seen a lot of people making changes that then allow them to change as well. So drastic environment changes. They either go to a new company, change the industry or change freelance versus working. Or working from home versus in the office. And I think something bigger like that shakes it up. Because I think part of this is ingrained in the person and not just the role, right? And so if you have ... It's hard to change who you are from so many years of practicing this great behavior. So I think sometimes it's a big change like that. 

But then I think it's just simply looking at what things aren't working and have an honest conversation with yourself, you know? Are you getting any exercise? Are you eating well? Are you getting sleep at night? Is your marriage really good? Or your relationship? And I personally had huge problems. When I went from having a job to freelance, I lost 20 pounds. I started sleeping an extra hour a night. My marriage got better. Started eating less junk food every day to going to more gluten-free healthy diet which is still not that healthy but healthy enough for me. And so I had to make a lot of those changes because sometimes you're in an environment where they accept and support you and then it's a matter of can you change being in that environment with all those practices? And if you can that's wonderful. Then you start setting little boundaries because you can't make big changes rapidly. Or the other time you're sometimes in an environment where you don't have that support. 

I've been in a place where I've said ... You know I've had my boss say, "I'm so sick of hearing from everybody how hard you're working." And I said, "I'm sorry. I've told you I have too much on your plate. I need help." And they've said, "Well go away and let me know how you figure that out." You know and that's set an environment where change can't happen, right? So if you're ready for change, you have to figure out if that environment's there to support you.

Carl Smith: Well I ... See owners go through a lot of stress as well. And owner burnout is a serious issue based on a lot of events that I've been to where I've gotten to hang out with owners and talk through it. But it's almost always more about payroll and business and how are we going to make sure we keep everything going? And can I have a smile on my face when I walk through the room next time because I really wanna just punch the wall? And listening ... Thinking about it really from the digital PM's perspective, right? They're trained to keep everything moving forward. Do you think there's a tendency for digital PMs to take things and put them on their plate that maybe they don't have to? 

Lynn Winter: Absolutely. I think it's when you're in a room and with your colleagues and you divide up the work and there's things sitting on the table that nobody volunteers to do or nobody has done before. I think a product manager often raises their hand and says, "Well I'll figure it out. It needs to get done. Somebody's gotta get it done. If nobody is willing to do it, I'm gonna do it." And part of that is how I ended up in content strategy and user testing and QA and all those kind of things. 

Carl Smith: Yeah. It's almost like anything that's a learnable skill, a digital PM will grab. Or anything that needs to be researched, and they'll put on their plate. And I remember sitting down with our PMs and just saying, "Show me everything on your list. Prioritize it the way you think it needs to go, and then let me look at it. And I can hopefully show you some things that aren't necessarily a priority that you can move on." Have you seen anything like that or ... I think with the teams too. You can probably ... Hopefully ... Again it gets back to culture, right? If you're in a bad job, in a bad company, none of this stuff works. But if you're at a company that sincerely wants to take care of the health of it's employees, do you think that sharing priorities and having everybody help can work?

Lynn Winter: I think it can but I think a lot of times it comes to a point where you're in between hiring the next role and that's where that stress comes in. So maybe you don't have a content strategist because you're not big enough. Or maybe you can't hire the second PM. And so there's that time and moments around, how do you take care of the work when it's not quite another role? And when does the company feel like they can jump to the next step and take that risk to have a whole nother salary on their books to fill in some of that stuff?

Carl Smith: And then psychologically, if you feel like you've got the weight of the world on your shoulders and you're the one that's been carrying it forward and then you do get support, that can be a freaky thing, too. 

Lynn Winter: Mm-hmm (affirmative). You don't want to feel like you're letting things down or you failed. 

Carl Smith: Or that and also it's like, "That's not how we do this. You know it's just easier for me to do it." 

Lynn Winter: Well there's that too. -

Carl Smith: [crosstalk 00:16:33]

Lynn Winter: And the perfectionist comes in and then there's issues around that, right? I do also think there's like a use of the industry challenge. So before I went into digital I was in television and the role of the PM's been around forever, right? Like that industry's been around for, I don't know, 75 years plus. Though there is just ... There was just a knowledge about why someone comes talks to me, what they need from me, why they should hide from me. But it was very clear. It wasn't like every month or six months there was a new thing that came on my plate. It was just like, these are your duties and then there's always that line in the job description like other duties as assigned. You know there wasn't new things, it was just volume, right? 

Like if you had a big production coming in town it was busy. And if you didn't, you didn't. And so then it was just about managing quantity of projects. Versus digital, like the actual role of the PM and what the PM should be doing is just in it's infancy. And so trying to figure that out at agencies. And then at some agencies really respect and value that role and some people don't and it's more of like a second class citizen. And so trying to establish that role with skilled people and the definition around that plays into this a lot, I think. 

Carl Smith: And along with defining it, standing by that definition or having a process for when it needs to evolve. 

Lynn Winter: Mm-hmm (affirmative). I was just gonna ... I think the strength of people in that role ... When you're in a place that doesn't have a PM or you're a brand new PM, you don't know what you're supposed to be doing or not. It takes years to be super comfortable knowing what the boundaries are and what you need to be doing to make sure a project's successful for yourself and then for your team. You know you move from one team to another team and that looks totally different. 

Carl Smith: Absolutely. Just based on companies that I've talked with, there are companies that their digital PM is basically like a secret ghost working in the background that moves things around. And you're suddenly like, "Whoa, how did that happen?" And then other shops, their PM is the conductor of the orchestra. Like they're up front and you don't go to anybody on the team with anything. You go to the DPM. 

Lynn Winter: Yep. 

Carl Smith: So in television how did it work? 

Lynn Winter: Well I think somebody defined it out before me. I mean I think that was what was great about it. I was learning from all the past years before what that role was. And it just never really came into question and I didn't really realize that until I went to a job where my first web agency, where they literally took two people's tasks that the two people hated they most and they made a job description out of it. Like I'm not kidding. They sat down and wrote, "I don't want to do these things anymore." And that became my job description. And it turned out it was things I liked to do, but that's how I started my digital career at a company, doing the jobs that everybody hated. 

And I don't think that's probably far off from what happens, you know? You start as a developer. You add, "I'm not good at making things pretty." You add the designers, [inaudible 00:19:52] gets added on. These people go to the company and they're like, "Oh, we've got all these tasks to do." Or, "I need some meetings scheduled. I need emails. Who needs to answer the phone." You know? Then a PM gets on and then it really just depends how that agency views that role and value. Like you can do it really valuable, or not. At the same token, it's up to the PM to define the value of it, right? It's not like up to the agency. A PM can take that role and really run with it and establish the value and then the boundaries around that as well. 

Carl Smith: And -

Lynn Winter: Basically we need time to pass. We need more time to pass. And then we'll be in a better spot. 

Carl Smith: Well no I think you're right. I also think the companies with the cultures and the appreciation for the different roles that it takes to create great digital will succeed. And that will become the case studies for the shops that suffer and can't figure it out. And you know even friends of mine have had amazingly successful shops that said, "We don't have project managers." If you dig into it, you find out that those roles were getting done by people who were still really good at them, they just weren't called project managers. And they may have been in between two different jobs. The idea that a PM isn't important or that there's one person in the company who's a superstar and they can just deflect whatever the PM says and do what they want. There's one shop right now, super great shop. Only five, six years old maybe. And I just have this sense that if the project managers were given a little more control, they probably would be able to grow without increasing the size of their team. But instead, they keep increasing the size of the team because they feel like they can't get everything done, but it's just 'cause nobody listens to the project manager. 

Lynn Winter: I know the feeling. But you know I think we gotta make sure we take responsibility too as project managers. And I think that's where education and mentorship can really help the people that are newer in the field get their footings and realize what their role can be and then stepping out of it, you know? I think you spend the first three years defining what the PM looks to yourself and then you spend the rest the time breaking the boundaries and making the magic, being the conductor. 

Carl Smith: And there are also some companies out there now that are doing training for digital PMs, right? 

Lynn Winter: [crosstalk 00:22:31]. 

Carl Smith: I know of two. And I wonder how aligned they are, right? It feels like if you start looking at different ways that people learn, like web standards unifies the way that HTML, CSS, all that kind of stuff gets used, way back in the mid 2000s. I'm just ... I want to fix it Lynn. How do we fix it? [crosstalk 00:22:54] doesn't work. It's like my wife says, "I just need you to listen, you don't have to try to fix this." But I'm just wondering if there is some level where things can be shown to be a best practice? Maybe that's what you're gonna do at the Digital PM Summit. I don't want to put a lot of pressure on you. 

Lynn Winter: Well I won't be talking about best practice of being a PM but happy to talk about it at any of the side events. But you know I just ... I think awareness is the biggest thing with burnout, specifically. I think understanding where you are, how comfortable you are in that role and where you want to be. And I think that's just basic life planning. Like where do I want to be when I'm 30, 40, 50, 60? Like what feels successful to me? What does that look like? And when we're too busy to stop and think about it, the entire life passes by. And that means we're moving too far, too fast. And so we need to just take the time to recognize what we need to have in our jobs to make sure our job makes us really happy. 

Carl Smith: Well and also not just defining ourselves by our jobs, right? Making sure we have things outside of work that make us feel good. 

Like me, I'm a very slow runner but I can run really far. And so I love running. Like this is ... I don't define myself by it, but it's part of who I am and it's the same thing with my family. Like for those of us that have kids, right? Assuming that your kids are really awesome like mine, you're like, "Well you know what? I'm a parent. I take care of my kids." These are things that are not part of the bureau although they're all interrelated. So I think that's another really important thing. And because a lot of digital PMs are younger, right? They may not have those other things to define themselves by and as a result they just throw themselves into work. 

Lynn Winter: Mm-hmm (affirmative). I also find too that I've met a lot of PMs that are kind of older and later in their career and I've seen a lot of people be very anxious about keeping up. They just feel ... There's just a feeling of ... And you know I'm starting. I'm not 20 years old either anymore and I'm starting to feel older in the industry and I think there's a feeling too when you get a little older that you feel like there's something you're missing or you're not keeping up and so there's a hustle around that that you feel like you need to do in order to stay relevant. And I'd love that stigma to go away 'cause it doesn't matter how old you are. That has nothing to do with the quality of a project manager you are. 

Carl Smith: Well thank you. Because now I'm getting the message I need to hear. 

Lynn Winter: Yes. So we did solve the problem. We solved your problem. 

Carl Smith: So it's all taken care of and as everybody that listens to this show knows, it's just about me. I'm just inviting people on to help me figure things out, so ... 

Well Lynn, I'm excited to say hey again at the Digital PM Summit and to hear you talk about digital PMs and burnout. 

Lynn Winter: All right. And by then I'm gonna figure out my new hobby 'cause I'm still working on allowing time for hobbies, so I'll let you know what I'm doing by then. 

Carl Smith: And we'll be in Memphis so if you can figure out the hobby and we can actually do it in Memphis, I'll do it with you. Especially if it's karaoke, just saying. 

Lynn Winter: Oh, mm-hmm (affirmative). 

Carl Smith: Not sure. 

Lynn Winter: Okay. 

Carl Smith: It could be. 

Lynn Winter: Not so good at that but maybe I'll try. 

Carl Smith: That's all we ask. All we ask of every attendee is that you try Karaoke. It's gonna be fine. 

Well everybody listening, thank you so much. Lynn, thank you for joining us today. 

Lynn Winter: Thanks for having me. 

Carl Smith: And we'll be back next week. We'll talk to you then. All the best.