Lynn Winter: Manage Digital 2019 Conference Recap

Lynn Winter, founder of the Minneapolis Manage + Digital conference, recaps this year's conference, gives us a peek behind the scenes of organizing a conference, tells us how meetup group formats are changing, and how to know if a Minnesota conference is a success (answer: it isn’t snowing).
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Lynn Winter

Founder and Digital Strategist, Manage+Digital

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The challenge of making one PM conference work for everyone, if they're all in different career places

How the effort in extending conferences uses the same math as having more kids, or why conferences are getting shorter

PM burnout, and how it's not about lack of career advancement

Why it's a sweet deal to be a sponsor at one of Lynn's conferences


IVAN STEGIC: Hey everyone! You’re listening to the TEN7 podcast, where we get together every fortnight, and sometimes more often, to talk about technology, business and the humans in it. I am your host Ivan Stegic. My guest today is Lynn Winter, a content strategist, digital project manager, and she’s also the founder of Manage Digital, a conference for digital project managers, that happened here in Minneapolis in May. She’s been on the podcast before. I’m so glad she’s with us again. Today, we’re going to recap the conference itself. We’ll find out from Lynn how the day went, what we learned, maybe what she learned and how she plans to make it even better. Hey Lynn, welcome.

LYNN WINTER: Thank you! Thanks for having me again.

IVAN: It’s lovely to be speaking with you again.

LYNN: Yes, you too.

IVAN: How’s your summer going?

LYNN: Well, I’d like to pretend that I’m sitting on a boat right now, and I’m calling in, but it’s going pretty good. Lots of work and some fun stuff.

IVAN: And, are you working on anything fun right now? [laughing]

LYNN: Well, I’m working on a couple different websites that have over 10,000 pages, so they’re challenging, and involve lots of spreadsheets, so that’s pretty cool.

IVAN: You love spreadsheets.

LYNN: [laughing] I do. I really do. Which makes me weird, but I like that. I also have taken over the interactive PM meetup group here, locally, and so I’m just starting to work through lining up speakers and getting that going. I’m changing the format a little bit to be a little more over the lunch hour and video conference, versus in person, just because it’s a little more challenging with families and finding venues, and stuff like that. And, I’m speaking at Twin Cities Word Camp in August. So, preparing for that as well.

IVAN: That sounds amazing. Before we get into Manage Digital though, I had no idea you were taking over the Twin Cities Interactive Project Management group. I’d like to learn a little more about that. So, you’re changing the format?

LYNN: Yeah. So, Megan [McInerny] from Clockwork, has been running it for years and has really been the godmother of the group and has grown it. I think there’s maybe over 1,000 people connected in that group. And she’s just got so many cool things that she’s doing on her plate, that this has just been hard for her to maintain. So, she’d reached out to me back in the spring and asked if I would do it, and I was like, “Yep, absolutely.” It’s important to keep this group going.

But I had to take a break with the conference and what not. So, I’m just starting to line people up. And I had recently spoken at a content strategy Meetup group and they had moved their meetups from meeting in person every month, to doing it during the day and online. And they found that more people were attending, it was just easier for the organizer, and so I started taking that approach for the fact that I have a family, and time is a constraint for me.

And, also the idea that we can talk with lots of people around the country or the world about project management. So, it opens up the speaker opportunities as well. I’m just lining up the first person in September. I’m trying to get someone for August, but once we get ramped up, we’ll be off and going.

IVAN: It’s really interesting to me that you’ve decided to change the format. The monthly Drupal group meeting recently changed as well. Allie Micka announced that. And so, we’ll be hosting the first Lunch and Learn in August, that is also moving to a daytime event, so that more people can attend, and will be hosted by a Twin Cities firm every month. But the idea here is also to make it available online, livestream so to speak, but as a meeting, so that we can get more Twin Cities folks involved that might not be, or Minnesota folk, or whoever is interested. So, it’s interesting to me that these groups have arrived at the same idea, more or less at the same time. It’s fascinating actually.

LYNN: Yeah, and I think back in the old days right, when we first started and people wanted to build those connections, we maybe had a lot more time, and we maybe didn’t have children [laughing] or as many children. And so it’s just changed and evolved, and I know everybody’s coming in in a different place in their lives, so a lot of this had to do with me making that shift.

But, it’s just hard to find food and the venue and do all those things. And so, I don’t want the learning to suffer from the structural, organizational stuff. So, I think it’s still important to get together and meet people and see faces and connect, but hopefully the shift will allow more folks to not be like, Oh, it’s the end of the day, I’m going to go home, versus Hey, it’s lunchtime. I’m going to grab my food and hop on.

IVAN: That’s my hope as well. So, I’m glad to hear that others are having the same perception and thought process. So, good luck with that. Come back and tell us how it goes.

LYNN: Yeah, absolutely.

IVAN: So, the conference seems like it was way, way back, right? [laughing]

LYNN: [laughing] It does, and it doesn’t.

IVAN: [laughing] So, we were still worried about snow on the ground, back when we did the original podcast, introducing Manage Digital 2. So, the first week of May, so the weather turned out just fine, didn’t it?

LYNN: It kind of did. It was a little rainy. It would’ve been nice if it was a little sunnier so people could be all about the grounds. But it was not snowing, and that’s the most important part.

IVAN: It was not snowing [laughing]. A conference success story.

LYNN: [laughing] I went to South Dakota after that and it was snowing there.

IVAN: Oh my gosh. Well I hope it doesn’t snow when DrupalCon comes next year, because it’s going to be around the same time.

LYNN: [laughing] Yes, exactly.

IVAN: Well, how is the American Swedish Institute as a venue? How did that work out this year?

LYNN: Yeah. You know, this was our second year back. We had a couple technical challenges the first year, and we were able to overcome them, and I thought it worked out great. It was still the right size, we still fit there, so it was cozy enough that everybody could connect and not feel like they’re in a grander place, and there were also little breakout places that people could disappear to, grab a coffee, and those kind of things. So, I found that it’s been a great venue to work with, personally. And they’ve had the right amount of space, still at our size, so hopefully we’ll be able to stay there for another year.

IVAN: Well, you’re talking about another year already. [laughing]

LYNN: [laughing] I think I always have to talk about another year, but I haven’t been planning it.

IVAN: Okay, well I was going to ask you about that right at the end, but since you brought it up, like what’s your feeling right now, and maybe now’s not the right time to think about it, or maybe it is. You like, just came off planning it, are you thinking about the next one? Is it something that’s on your mind?

LYNN: You know, I think I always think about it, But what I did last year, and I am doing right now, is just kind of taking a mental break from it. So, I don’t know if folks know this, but, this last year was basically me organizing the whole thing. So, it does take a lot of time. It’s all been volunteer time up to this point, so I’m the person that does the things, and so, it does become a bit overwhelming, both my work and my personal life, but I do it because I love the opportunity to bring folks together. But that also means I need to take a complete mental break from it, and just not think about it. So, I’m kind of in that mode.

The first month is like recovery mode and then the next couple months is break mode, and then come the fall I start thinking about if there should be a format change, who the speakers are, if we’re going to change venue, and all those sorts of things. So, I think the biggest thing from year one to two is we changed the format a bit, we moved happy hour up, we shortened some of the sessions and added a more interactive table discussion, so that the folks there could talk to each other and connect with each other.

IVAN: Did you do a survey this year?

LYNN: I did. Yeah.

IVAN: And what did you learn from the survey? Or is it too early to talk about because you’re in the second month after?

LYNN: I think we’re allowed to talk about it. Of course, only a handful of folks fill it out, and it’s always hard, you’ve been part of events before, Ivan, and you get the feedback on both sides, right? Like, “I really love that change.” “I didn’t like that change.” “I wish it was two days.” “No, one day is perfect.” “I love the food." "Why didn’t you have this?” So, it’s kind of all over the map. I mean, I think in general what the PM community is always echoing is more specific content for their job. It is really hard, programming-wise to find people that are talking about PM stuff on a regular basis, so that they’re an expert. And you know not only in their field or do a lot of public speaking, that can get down to the nitty gritty of what people need. And it’s difficult because the quantity of folks doing that is slim. And then on top of it, everyone’s on a different path, so what you need as a PM in the first year of being a PM or the first year moving from maybe in-house to agency side, or someone that’s a veteran, they need very different things.

And it's very hard in one day to pack that kind of experience. So, you know, I try to do my best, and then we try to find the right folks, but every year there’s the, “This didn’t pertain to me.” Or, “I really needed this topic.” So, it’s a bit of a challenge, and that’s why we did table topics this year. Not only are there a bunch of smart people in the room that are attending that can give really good advice, but there’s specific topics and questions that people are coming with that are really specific to that time and space they’re in right now. And there’s probably not a session that’s going to cover exactly what they’re talking about and challenged with, and so, that’s what the table topics were hoping to achieve. That I’m coming with these burning things, please someone help me. I need help right now

So, I think the survey’s a mixed bag, like overall positive, but it’s just hard. And so just changing it up all the time, making sure people are able to connect with other people so they can build those relationships throughout the year. I think it’s really just the best thing I can do.

IVAN: And it’s so awesome that you actually do a survey and try to listen to your attendees, as opposed to putting on an event that you want to have, that is centered around how you think the community should be reacting. I think’s a really important step to be doing. I was going to say, you could just ask the questions that don’t have hard answers in your survey. [laughing]

LYNN: [laughing] And just….”Do you like the parking?” “Was it sunny enough?”

IVAN: Well, there’s nothing I could do about that, right?

LYNN: I love the feedback. I love hearing everything’s great, I do. But I love the stuff that says, "You need more diversity," "You need more of this." And I do know the efforts, diversity is a challenging one, and I know the efforts I try to put out to get the things, but hopefully people can see that I’m trying, and I will try to continue to evolve and improve it.

IVAN: I think it’s wonderful that it’s a conference that’s being run and organized by a woman. I think that’s a great step.

LYNN: I didn’t even think about that.

IVAN: That’s amazing. That’s awesome.

LYNN: Yeah. Hmm.

IVAN: Well, as far as I’m concerned that length of the conference, if you’re asking me is, excellent. I love the fact that it’s one day. It’s not too long. It’s not too short. I love the amount of socialization there is in there. I like that there aren’t many different rooms with a classroom-type feel, people talking at you. It felt like it was more interactive. Now, I didn’t get into very many of the sessions, and I’m sure you didn’t either, given that you’re the organizer, but I thought the length was pretty good. Is there any feel for whether that might be changing right now?

LYNN: I actually really like the length this year, especially moving happy hour up, because more people stay. The truth of the matter is, I’ve gone to a lot of out of town conferences and a lot of local conferences, and when you’re local and the audience is local, people go home to their families, or beat the traffic, or need to go home and wrap up that thing at work, and that’s just the truth. And unless you're leaving and going to another city, and staying in a hotel, there is a confined period of time. So, I thought our attendance was a lot stronger, both throughout the whole session and happy hour, based on a slightly shorter day. Because I think last year, or the year before, we went to, I think, 5:00, 5:30, for the conference and then happy hour started, and so it just became quite a long day for most folks. And I get it. I totally get it. I’ve been there. I’ve been that person.

So, I think shorter was good, and I honestly don’t think if it’s just me, I think it’s really hard to do two days. [laughing] So, right now that’s not going to happen. That could be a future thought, but conferences are really expensive, and probably what people don’t understand is the bulk of that is the food.

IVAN: Yeah, and it feels like the trend at least in the regional camps of recaps that we’ve done, and one’s that we’ve attended, it feels like they are actually getting shorter. So, you have those four-day camps that are suddenly three days, like Twin Cities Drupal Camp was this year. And, making a single day conference turn into a two-day conference, yeah, it doesn’t feel like it’s also double the work, it feels like it’s exponential. It’s like when I’ve told people that having had kids, that, if you have a second kid, it’s not two times the work, it’s four times the work. And if you have a third kid, it’s nine times the work. So, keep that in mind.

LYNN: There’s got to be a point when you have five children, or five days that’ll work, it feels the same maybe. [laughing]

IVAN: [laughing] I don’t know. Maybe.

LYNN: I'm never gonna get there. Just a thought.

IVAN: Just a thought. Okay. I want to talk about the keynotes. Rob Harr and Kurt Schmidt, I thought gave wonderful keynotes. I especially loved Rob's. He really had some nice nuggets and reminders, like think about joy, think about the empathy. The thing I remember the most was the advice he gave about asking the question, “Can we postpone that decision?” And, I’ve been using it since the conference. That’s like my biggest takeaway from the whole day, was, if I’m trying to make a decision and we’re not sure that we have all the information, I give myself permission to say, “Can we postpone that decision?” And I’m sure people at TEN7 have heard me say that recently. That’s where it came from. I really love that he gave me permission to do that, so thanks Rob. What were your takeaways from the keynotes?

LYNN: Yeah, for Rob, I think, I’ve been in a management position in the past, and it’s really hard and humans are hard. But I’ve always thought about being good to people, and how you manage people, or lead people, is really just based on values. But he talked a lot about it being essentially good for business, in that there is so much value and savings around just being good to humans. Not only to the world and putting good things out there, but also to your business growing. So, he talked a lot about the words you use, and how you treat people and how you foster people through and invest in them. It wasn’t necessarily new ideas, but I like how he patched it together to really put an emphasis on it, and how it’s just business smart.

IVAN: Yeah, isn’t he the one that said "Being kind is free"? Was it him, or did I hear that somewhere else?

LYNN: I think so.

IVAN: Yeah, he basically said…

LYNN: But why not, let’s just decide though? Let’s attribute that to Rob. [laughing]

IVAN: [laughing] Let’s do that. And it makes a lot of sense, right? It’s not going to cost you anything, it’s free. It does the world good. Have empathy. Be kind. Be nice.

LYNN: And the think is, you know, he was talking a lot more from an operational, owner type of perspective, but you can really pull that down as a project manager, and how could you take that to what you need to accomplish and get done and what your goals are as a project manager and projects, and how then you treat the people around you. So, I think while it was a lot more of a higher level, you can really take those ideas and push them down, especially making decisions, pushing that down to a project level, client-level types of relationships.

IVAN: It was a good day of keynotes, I think. I love that you shared your story about signs of burnout and making sure that we were practicing self-care as much as possible. Why did you decide to talk about burnout in the closing session?

LYNN: Well, it’s something I’ve been talking about on and off for a year or two. And essentially, I had a big life change about two years ago when I left a company and I started going freelance. So, it’s kind of easy to talk—well not easy—it’s really personal to talk about what changes you’ve been going through. But I find that in this community I’ve been hearing this echoing over and over and over, and a lot of times people talk, in maybe the development or design world, about how they’re hitting the ceiling, that there’s no job to move to. I hear that less in the project management world, because it’s more about burning out and quitting and not liking the job.

And they’re attributing it to, "Oh, I don’t like what this job’s about." Or how it’s treated or done, and I think there’s a lot of burnout that wraps up in it, and people are leaving the field, maybe more related to that than anything else, versus "I can’t move into a manager position." I mean, actually PMs quite easily move into that next level and then on to COO opportunities. So, there is actually a nice path for a project manager as far as scaling up.

But I’ve heard, since I’ve been talking about this, so many stories that just kind of break my heart, of people just feeling like they’re stuck, they’re trapped, “I’m working until midnight.” “I’m working in a place where people hate me, and they treat me terribly.” Or, “They don’t value the role, and I’m just doing all these things and I keep on going. I’m just pedaling forward.”

And, I was doing the same thing, not all those scenarios, but I was doing unhealthy things that were hurting me physically, emotionally, hurting my family, and maybe I’m just having some sort of midlife crisis, and making change, but I’m realizing like, Why? Why now? Why am I doing this? What’s the goal? What’s the point? And so, I’ve been trying to share that story with the folks that I think it impacts the most, in hopes that I can help someone make a change and a difference in what they’re doing for themselves.

IVAN: I think you are making that difference, and I appreciate the work you’re doing to bring it to the surface, and to talk about it in public, and to be so open about it. I think that’s rather admirable and I commend you for doing that.

LYNN: Thank you.

IVAN: Any feedback from the sponsors? I mean, I can give you some feedback right now.

LYNN: Maybe you should. [laughing] You know, the interesting thing when you run a conference is you actually don’t get a ton of feedback from sponsors. The first year I got hardly anything. I did meet with VOGSY afterwards and they talked about it. Their sponsored goal is they want to support the community, they think there’s good value there, they’re trying to make connections, they might be trying to make sales based on what they’re trying to do, or hire PMs.

And so, VOGSY specifically is looking to spread the message about their product, get awareness about it. And so we talked about how that worked and how that might change in a future year.

But I’d love to hear from you. Your role is very different than a product or service. What were your thoughts and value of sponsorship?

IVAN: I thought the value was really high. I loved the fact that you were so open to allowing us to run a competition and then announcing the winner at the end of the day. I thought that was a real win for us. I also loved the fact that you had a sponsor table with things on it from sponsors that the attendees had to walk past, had to pick up—well they didn't have to pick up. I loved the proximity of the sponsor goodies table to the fact that most people who were attending had to walk past it, and that you had someone manning it, and saying, “Hey, these are our sponsors. Here are things you could take from them, and you should take them.” I really liked that.

I think it goes without saying, the fact that we’re supporting the local community, that’s valuable to me, as well. Visibility for me was really important as well. I was happy with the amount of logo visibility that we had in the slide decks and how often you mentioned it, and the fact that it was on the cards, right? On the conference name badges, right? Yeah, so that was good. In general, I thought it was good value for a sponsor, and if there’s anyone listening who is interested in sponsoring, you should absolutely do that. I only have nice things to say about it.

LYNN: That’s good to hear, because it’s a balance for me for sponsorship of not being, like, we want to make sure that when we pick people—I say we, but it’s really me, but... [laughing]—that people have the right values, or we believe in. We’re not just trying to get sponsors to get sponsors, so we want to have the right folks there. At the same time, we also don’t want to throw sponsorship in people’s faces. So, I love the idea of mentioning things, bringing stuff up in a nice way, that doesn’t feel like a sales pitch situation for the attendees. Everybody knows it’s important to have sponsors to pay for things, but at the same time, folks don’t want to be feeling like they’re at a used car situation.

IVAN: Yeah, I would not want to feel like we’re in a used car situation either. [laughing] If people associate used car salesmen with TEN7, I think that would be a fail, but I think we avoided that. So, we’re good.

LYNN: [laughing] That’s maybe not the right reference, but you know what I mean.

IVAN: I do. You don't want to be pushy.

LYNN: I want it to be integrated in a nice way and that people want to come up and talk to you and choose to come up and talk to you. So, there is engagement, but it’s not this frustrating situation.

IVAN: I think the thing you hit on was the fact that there was an overlap in the values. And I think I must’ve done that self-consciously, because I honestly think that there is an overlap in the things and values that TEN7 stands for, with the values that you have Lynn, and that Manage Digital espouses on an annual basis. And, I thank you for selecting us. In retrospect, that was a huge win for us, I think, as well.

LYNN: Well, thanks for sponsoring.

IVAN: Yeah, we’ll do it again next year if you’ll have us. [laughing]

LYNN: Oh hugs, loves. [laughing]

IVAN: Heart, hugs, it’s awesome. [laughing]

LYNN: It’s getting awkward people, I’m sorry. [laughing]

IVAN: [laughing] So, I don’t think I can ask you about 2020 then, because we just talked about how you’re not in month three yet. You haven’t started thinking about it. So, I’m not going to ask you. I’m just going to say, “Watch this space that the conference may happen in 2020." I’m going to say, it probably will. Is it going to be the same format? I don’t know. I would say it probably will. But, if we’re there and you’re around, and we can sponsor it again Lynn, let me know, we’ll do it!

LYNN: Great. Well we’ll have you down, yeah. And I think folks, if they want to stay abreast of what’s going on, sign up for the newsletter, and I don’t send out a lot of newsletters, so you get just the basic information that you need. Also, if you’re looking to connect with folks in the Interactive PM Meetup, go to and find the Twin Cities Interactive PM meetup group and join us and be part of it.

And, if anyone out there has ideas about speaking—we’ll do more of a formal speaking call this year—or sponsoring, or ideas, reach out. Ivan and I talked about this before we started recording, but I don’t actually get to attend much of the conference. I’m running around doing stuff. So, it’s kind of sad for me a little bit, because I miss so much of it, I don’t get to connect with as many people as I want, or talk, but the conference is not for me—it’s for the community. It’s to grow and strengthen the great folks here. So, if there are ideas out there, let me know.

IVAN: And, we’ll link to the website and how to sign up for your newsletter on the podcast episode page on So, take a peek there if you’re listening, and that information will be available.

IVAN: Thank you so much for spending your time with me today, Lynn.

LYNN: Thanks for having me.

IVAN: It’s really been a pleasure talking to you. Lynn is a content strategist, digital project manager and the founder of Manage Digital. You can find Lynn online at And of course, Manage Digital Conference website is and you can sign up for the newsletter on that page as well, and Lynn promises not to send you a ton of email. You’ve been listening to the TEN7 podcast. Find us online at And if you have a second, do send us a message. We love hearing from you. Our email address is [email protected]. Until next time, this is Ivan Stegic. Thank you for listening.

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