Lynn Winter: Navigating the New Normal After the Pandemic

Digital strategist Lynn Winter discusses how the pandemic affects our work, children’s education, and sporting events.
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Lynn Winter

Founder and Digital Strategist, Manage+Digital

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The benefits and challenges of virtual conferences

What it’s like to shoot video at sporting events with no spectators


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'm your host Ivan Stegic. My guest today is Lynn Winter, who is a seasoned digital strategist and has been managing teams and projects and people for so many years. She’s also the founder of Manage Digital, an actual conference with real people in the same space for digital project managers that’s scheduled right now for a new date in August of this year. She’s also a videographer and has worked many popular events including the Super Bowl. And, she’s also been on the podcast a number of times before. So, welcome back to the show Lynn.

LYNN WINTER: Thank you! Thanks for having me. Kind of from your intro I sound really old and very seasoned.

IVAN: [laughing] I don’t think you’re old. You’re experienced.

LYNN: [laughing] Maybe it’s these days feel old and long.

IVAN: They do, and it feels like I don’t know what day it is anymore. It could be the weekend tomorrow, I don’t know.

FLYNN: I thought it was May yesterday. It’s fine.

IVAN: [laughing] It’s almost May. Unprecedented time, isn’t it?

LYNN: It is.

IVAN: [laughing] I hear that word a lot, unprecedented, and it really is. Like, who lives though a pandemic? It’s pretty insane. So, let me ask you. How are you faring? I hope your family’s good. I hope everyone you love is safe and healthy.

LYNN: Yeah, I think we have probably the same complaints that most people have and that you maybe have. We have elementary school aged children at home trying to learn. I was working on multiplying fractions this morning. So, we’re trying to get work done. We got one unemployed family member and trying to live in the world at home and a complete extrovert. But we’re healthy and so that’s all that matters. We know some people that have diagnosed and passed away, and so, it’s really hard, but right now I’m just blessed to have a happy, healthy family at home.

IVAN: I’m sorry to hear that with your friends. That’s awful.

LYNN: It is, but you know everybody has these stories, and we’re going to continue to hear these stories. The more we can stay home and stay safe I think is the best we can do for everybody.

IVAN: Totally agree. Stay at home everybody. Wash your hands, stay at home.

LYNN: I’m sorry, it was really heavy to start with. [laughing] Sorry.

IVAN: [laughing] Not at all.

LYNN: [laughing] Bad news yesterday, but we’re doing okay.

IVAN: I’m so sorry. I’m so sorry. Good, good, good. Well, I want to talk about how the pandemic has affected you, but maybe in your work life, and what it might look like when this whole thing subsides. So, you wear a lot of hats. You’re a consultant, you’re a conference organizer, you’re into videography as well. Your husband, you mentioned, was unemployed because of that, so I’d like to get into how this has all affected you.

But let’s start with your consulting business, right. We work together on a pretty regular basis, right? You’re our go to content strategist. And we’re typically pretty hands on with our clients in the early stages of our project, right? Kind of spend time in their space, in their conference room, we use post-it notes, we spend 9-5 in a meeting room, lots of people jam packed together. You’re kind of not doing that anymore are you?

LYNN: No, we really aren’t. [laughing]

IVAN: Yeah, so, kind of describe what something typical in a discovery process might look like, very high level. Do you want to expound on that a little bit? What do you normally do, and then how has that changed in the couple of recent projects that we’ve done?

LYNN: Yeah, so, it depends really where we’re starting with the project, what the project goals are. But essentially most of the discovery meetings are in person, hands on and they involve key stakeholders and maybe some extra stakeholders that need to be making some high level decisions about goals and where the content and marketing is going for the organization, and we like to make it more interactive as possible. So it does involve post-it notes and whiteboards, sometimes there’s card sorting going on, and anything to make it a process really to help people think through where we’re going.

So, the more hands on the better energy we have, the better outcome. And, so, shifting down to not be in person is really different. Around that, we have moved essentially the first couple weeks is, okay we had this meeting now let’s just do it on Zoom. Okay, and now we’re doing this meeting on Zoom. The first couple weeks was really about just everyone be home. Can you meet at this time? You have children? How we going to get this done?

And so, it was really more about that, and now we’ve all hit the Zoom overload, and those meetings that aren’t producing the same results. And now that we’ve been in it for a while, it's time to shift through how we can really deliver stuff. So, I’ve kind of been thinking about some things that I’ve done, and I’ve kind of got some goals for the future.

IVAN: Yeah, one of the projects that we were working on together, you kind of shifted the strategy, and instead of meeting in person, you gave homework to clients.

LYNN: Yeah, and honestly we did that because they said they can’t meet. [laughing] So, it started with the need, right. And it’s been something that we’ve carried through with other clients, because it’s worked much better. So, what I found is that, they didn’t feel like they could meet on the phone in a remote call and have that first initial dialogue. And I‘ve never met with this client before, besides just a hello and how are you doing kind of situation.

And so, we really had to take the dialogue we have instead of just an agenda, but really work through what do we need the outcome of that meeting to be. What are the steps they need to go through, and then how do we then take a process where we maybe put 40 words on the table and then need to sort and organize them? How do they do that together? And so, we assign them homework, and that client particularly did a great job, and it’s partly because clients have more focused uninterrupted time. They have this ability to really hunker down and really think through. So, in the past when you get to meet them in person, and they’re in their offices and they have all those interactions, they don’t give you as good a feedback outside the meeting and they need at that meeting.

Now, it’s kind of flipped. The meeting has been less valuable often. It’s just not as dynamic, and people are separated and then people need to go and take care of something in the meeting and stuff, and really this at homework time is actually producing some better results. So, I’ve kind of taken some meetings and either shortened them, because longer meetings are unproductive anyway, breaking them into multiple meetings and thought through, What can I assign them as homework that I can get really good value to bring to that meeting beforehand.

IVAN: So, how do you get the best of both worlds then? Let’s look medium to long-term, because we’ve obviously learned something from this. You found a way to get even better uninterrupted feedback from the client. But yet there’s this value in being in person. So, what do you think happens going forward? How do we learn from this?

LYNN: I think, a lot of it’s really around the management and planning and really thinking through, which we should do all the time right. But we kind of get into rhythms of, This is what the meeting is, and everyone’s got a role, we’re going to show up and we’re going to get something out of it. But I think we have to be a little more thoughtful. Like, really, what is our goal? What do we have to accomplish by the end? What are the best ways to do that? I don’t think, this isn’t a time period, this is a change in our life. And I don’t think even if all of a sudden it goes away and there’s no worry about getting sick, I think people are still going to work from home more, and it’s going to change that up. But we’re not going to always be in the office. And, so, we have to come up with a game plan for different scenarios.

IVAN: I think you’re right. I don’t think this means that everybody is going to work from home. But I do think that this means that companies are now forced to be a little more serious about having a work from home policy and having an opinion and being more flexible about how their employees work for them. I was just talking to someone today and before I used to say, Oh, you know, this whole pandemic, it’s a temporary thing, it’ll pass, some things will change. We’ll pretty much go back to the way it was before. I hope.

Now, this person brought up the comparison with 9/11, where basically everything changed and nothing went back to the way it was. And now I’m starting to think, Well, I think there’s going to be more of an effect than I thought. And it’s not just going to be working from home. I think there’s going to be more people wearing masks for longer periods of time. And us maybe even thinking about how we behave when we’re out in public. How does it affect going to see a show, or a bar, or a concert? It’s so unknown right now.

LYNN: And if you start to read some of the projections of what they think they’re going to do with colleges and schools, that looks extremely different, which will impact how we work, our ability to be available. I mean, nine to five, hasn’t been a thing for me for a while [laughing]…

IVAN: Yeah, me too.

LYNN Because I do consulting work, but I think it’s going to be that way for everybody now. I think it’s going to really shift. I mean, talking about cutting class sizes, maybe these are the days your kids go to school, these are the days they work from home. It’s just a very different world, and so, I think when it comes to projects we have to think about, we have to take our game plan and multiply it. Like, here are the different scenarios, here is our toolbox, and we need to grow those options and then kind of be really thoughtful about what do I need to bring to the table at what moment.

IVAN: Yeah, I didn’t realize they were talking about spending a couple days at home and three days at school. I didn’t realize those conversations had started like that already. Wow. So, are you expecting that to happen in the fall with your kids?

LYNN: I think it’s so early to know. We’re coming out of the Stay At Home in Minnesota in a couple days, but yet our numbers are jumping up drastically in the last few days. So, it’s hard to know that. For me, I’m just trying to think through the summer plan, because we had all the summer camps, and even if they’re allowed to go do I want them to go? It’s different. My oldest child is jumping into middle school, and so trying to navigate having one teacher to having six different teachers, and if some of that’s remote. I think the whole education world from kindergarten, early education to college, has to rethink, What does getting work done look like, and how do we use those tools and what do grades mean anymore. We’ve already flipped the switch on what ACT and SATs mean, because the people are paying for them. So, the whole system, I think is having this big rattle, and it’s going to continue to happen. But I know for my kids they’re on screens all day now. I’m not perfect by any means, but we were limited with them for screen time, and now they're getting headaches.

IVAN: Oh, no.

LYNN: And so, ‘cause there’s just a lot of time to sit on an iPad and that’s where all their homework is.

IVAN: Yeh, I saw there might’ve been a bit of an accident with one of your child’s computers. [laughing]

LYNN: [laughing] The laptop.

IVAN: The laptop.

LYNN: [laughing] You know that laptop had a very hard life, and it was about six years old, so it was already on the end of its life. And my husband maybe left it at the Boston Airport a year ago, maybe left it in security and didn’t bring it home, and they shipped it three weeks later, and the whole screen was cracked. So, at that point we’re like, it’s old, he’ll get a new one, my daughter can use it. But then she dumped water over the entire thing. [laughing] And I was like, Well, I’ll just blow dry it quick. And I thought if I blow dry it the same temperature that I use my blow dryer for myself, no big deal. No. I’m telling you everybody...

IVAN: Yeah, don’t use a blow hairdryer on a keyboard. [laughing]

LYNN: ... It melts all your keys. How could it melt the keys far away when I put it closer to my head? [laughing] Like I’m starting to question what I’m doing to myself every day. So, of course it’s turning back on, but the keys are totally whacked. [laughing]

IVAN: Oh, it actually turned back on? Wow.

LYNN: Oh yeah. [laughing] It’s totally functioning.

IVAN: Oh my God. Well at least that’s a good thing I suppose, but maybe a good reason to get a new computer.

LYNN: Yeah, well, we just shifted to an iPad. [laughing]

IVAN: Wow. Well, let’s talk a little bit about your pet project that’s actually driving business, your conference, Manage Digital. I’m pretty sure, wasn’t it supposed to be today?

LYNN: [laughing] Today. So sad.

IVAN: [laughing] Oh, man. I’m so sorry. So, it’s not happening, just for those that are listening. Not today.

LYNN: Not today.

IVAN: But it is on again in August. So, you’ve rescheduled it. You’re hedging your bets that we’re all going to be good and available and in person in August, which I mean I would agree. I think that’s a smart bet. At what point in leading up to your decision to like, Okay, we need to shift this? What was the turning point? What was the thing that said, Okay, yeah, I absolutely have to change this date?

LYNN: There was a hockey game for the benefit of the (MN) Wild that was scheduled in the beginning of March and my husband had gone to work there, and I was supposed to work there later that night. And he called me and he said, “They’re sending us all home. The season is cancelled.” And that was the day after the NBA had a player test positive. It was at that moment I knew it was not going to happen. But I needed time to figure out what that meant, because I am a single entity that puts on the conference. It’s a big financial situation for me.

IVAN: Of course.

LYNN: So, I needed to reach out to the venue, reach out to the speakers, talk to the sponsors and just see is this an option for everyone. So, at that point the conference was like, You can definitely move it. We will be flexible and it’s adjustable. So, I tried to pick a date that was far enough out that we can hopefully make it. Because so much of the value of the conference is seeing people in person and building those relationships and connecting with people.

IVAN: That networking of actually seeing those people. Yeah.

LYNN: Yeah.

IVAN: Yeah, and of course, so the venue is the American Swedish Institute down in Minneapolis, and just from their perspective, they must’ve been totally freaked out about all of this as well, right? They’re a museum, they’re a nonprofit, they have a gift shop, so retail, and they have a restaurant, so restaurant industry, and plus they do events. How did that work with them? What was their approach?

LYNN: You know, honestly, I was not the first person to contact them [laughing], so they were pretty calm about it, and they already had in play, Here’s the policy. Because I had called them before the official lockdown, that it was, You could lose the deposits and cancel and that’s fine. We can also just let you just move it within a year time span. So, they were totally flexible about that. I think they honestly, the bigger problem for them is really the attendance in the museum as well as weddings. They do a lot of weddings there.

IVAN: They do a lot of weddings, especially in the summer.

LYNN: Probably less events. A couple hospitals use them regularly that they’re nearby, but I think they do more weddings than anything. So, I think that is probably more of a challenge. But they’ve been talking to other venues in the Twin Cities and trying to figure out what’s the stance on it, and so, I thought they were more than fair that you could move it. It makes sense that they can’t give back everyone’s deposit. That would decimate them as a nonprofit and so.

IVAN: I can’t even imagine what it’s like for the Drupal Association or for Confab to have to rearrange and replan and do all of that work for an order of magnitude more and the number of people that attend.

I’m hoping to be talking to someone at the Drupal Association soon. Maybe we can get them on the podcast. And then Kristina hopefully will be on the podcast as well, and we’ll ask her about Confab. Did you ever consider making Manage Digital virtual? Was that even ever a thought?

LYNN: Well, it is now. I don’t want anyone to feel in jeopardy, or if there’s any danger out there, it doesn’t make any sense to put anyone in danger. So it is still a consideration that at some point we might need to go virtual versus delaying until maybe next year.

I was really, really excited about the content line-ups and the talks that people were giving, so I’d hate to push that too far off. I still would want people to be able to have that information, but I am just waiting and seeing. If things are slowing down, we are, as far as the states in the U.S., Minnesota is one of the best situated states when it comes to Coronavirus, as far as infections per capita, but at the same time, one is still one. [laughing]

So, we just have to wait and see. We still got time before any sort of pivot would need to be made for that. I’ve been attending some virtual conferences just kind of seeing what’s working for them, what’s challenging. I still would hate to sit through that, because I think the in-person is definitely lost, but I’ve got to be open to it, because this might be longer. They’re talking about canceling sports seasons and not letting people go back to college. You just got to pivot.

IVAN: As a sponsor we’re happy to support you in whatever decision you make, and we will be around for that, and we will be around next year as well. So, you have our support, and I wish you the best, and I hope it works out well for all of the attendees and for the content, because the content is basically what you want people to have, and the networking is a big part of it, and I wish you the best with that.

LYNN: Thank you. Thank you for your support.

IVAN: You bet. You were talking about professional sports. You mentioned the hockey league being cancelled. I was just reading this morning about how the baseball league, the MLB are planning tentatively in June. Personally I think that’s a little optimistic.

LYNN: But technically it’s the end of June. [laughing]

IVAN: It’s the end of June. It’s also an unsubstantiated report based on anonymous sources. But, it’s interesting what they’re talking about. They’re talking about reducing the number of games and changing the leagues so that they’re geographic as opposed to cross country. So, I think that’s kind of smart. That’s a good idea. You have some experience with professional sports, and you’ve worked the Super Bowl which I always think is really cool. [laughing]

LYNN: [laughing] It was cool.

IVAN: But what do you do about other team sports and individual sports like hockey and football and tennis? A large portion of the community, of the economy. There are so many industries that get affected that you haven’t even thought about.

LYNN: Yeah, it was interesting, because really sports was the first thing to go, and there’s so many people on unemployment and trying to figure things out, but sports and events was kind of the first wave. So, it hit us. I do sports more on the side, but it’s my husband’s full-time work. He crews events at the convention center. He works for them in sports. So, it’s been something we’ve been really paying attention to of how that changes, and when we go back to work. So, every sport’s been very different now. Football has not released their schedule yet, which should’ve been out in early April. They’re waiting to see what happens and so they haven’t finalized when the NFL is happening.

IVAN: When does that start? Does that start August or September usually?

LYNN: There are preseason games in July.

IVAN: Oh, so sooner.

LYNN: The season’s very long.

IVAN: Oh wow. Okay.

LYNN: So, you know, they’re certainly going to be shifting from that, but they, I can’t remember when camp starts, probably in June. So, they’ll have to have some sort of shift. The X Games have been cancelled, which have been held at Minneapolis for the last two years, and the third year was going to be this year. Hockey is looking at a regional plan. I shouldn’t say regional, because that’s more of the baseball plan, but what they’re doing is looking at four different places to play. And so, the regional teams would come and stay at that location and just play in their arena, and Minnesota’s one of those places they’re considering. So that would include Detroit and Chicago, obviously us.

IVAN: Winnipeg? Doesn’t Winnipeg have a team?

LYNN: Probably Winnipeg makes sense. So what they are doing is that once they think it’s ready to start, they will bring in all the players that are out of the country, and they will have a couple weeks in quarantine. And once everything passes they’ll start to work out as a team, and then they will come back and finish some sort of version of the season. And it’s a big financial thing, because the playoffs bring in so much money for them. Because I was kind of thinking maybe the MBA and hockey would just drop, but there’s a lot of money in that kind of thing. [laughing]. So, they’re looking to start in July, which is a very interesting time [laughing] to play hockey.

IVAN: Yeah, right in the middle of the summer. Geez.

LYNN: Yup, and the Minnesota United which I work those games for broadcast, they’re on hold, and they have hoped because their games are more spread out, they still have hopes of maybe making up a lot of the season, when and if that comes back.

IVAN: Their season is long, but it’s a short number of games and there’s a whole bunch of time in between, right?

LYNN: Yeah, I think it runs from March to October, so they've already had a couple games. They missed the first home game, but they’ve had a couple on the road games. So, they started the season, so they have a leg up on that.

IVAN: Wow.

LYNN: It’s different. [laughing]

IVAN: It really is.

LYNN: And it’s the camera people, the broadcast people, it’s the people that sell you the food, it’s the ushers, it’s security. There’s so many folks involved.

IVAN: It’s hospitality that is in the hotels and the restaurants and the bars around the facilities. And then when you watch and rewatch all of those video feeds, it’s all the advertising dollars that are being pushed into the video streams that go out, right? There’s like that part of the industry too.

LYNN: What’s interesting about that is that the subscription feeds are still there. So the folks that own, ESPN, CNN, Disney, the folks that own the rights are still getting paid the subscription fees, because you still have been paying for your broadcast, right?

IVAN: That’s true. I’m going to watch CNN.

LYNN: So, they’re actually making the money, and that’s kind of a bit controversial. It’s been in the news, because the folks at what we call Big Socks, something you’d see late night on Channel 9, they’re getting paid for the events they’re missing. But if you look at the sports broadcast in our area, that’s regional, so there’s a lot of regional people that are not getting paid, because they’re owned by a different organization. And so, those folks are kind of stuck and have nothing coming in.

IVAN: That’s awful.

LYNN: It’s been different how people are dealing with it. I was supposed to work for NBC for a hockey game and they paid me, and it was a week after things got cancelled, which is wonderful. It’s great that they supported us in that way.

IVAN: Wow. Do you think there’s going to be any technology disruption, or other kind of changes to the way that events are run and broadcast, medium to long-term? We talked about maybe work from home is affected by big companies, what about camera operators. Are we going to see more robotic cameras? Are we going to see more vending machines in the stadiums? [laughing]

LYNN: [laughing] Wouldn’t that be great, like a big thing you stick your hand in.

IVAN: [laughing] Out pops a fresh hotdog.

LYNN: [laughing] You know, it’s hard for me to imagine the service part and the people being gone completely, but you might be right. There might be a table of the way that your drink is delivered is different, but I can’t imagine a stadium not being packed full of people. That would be really sad.

IVAN: It would.

LYNN: Equipment wise, when you go to set up your stuff your kind of by yourself. There is an ability to separate and be more isolated, so whether it’s a robotic camera or hard camera or a handheld which you run on your shoulder, then people set up their own thing. I don’t think moving to more robotic cameras would necessarily change the exposure of those folks. Though my husband is a robotic camera operator [laughing] so we’re safe. I am not at all, but he is. I guess that’s good.

IVAN: Does he do the drone footage or the footage that’s like the aerial stuff?

LYNN: He used to do the skycam and cable cam.

IVAN: Oh, he did. Okay.

LYNN: Yeah. I always tease him because he peaked in his early twenties, and then he decided to stay home and have a family. So, not as exciting anymore. But, those things take an in-person crew to set up.

IVAN: That’s crazy. Wow.

LYNN: I’m not sure. I said to him, “Is it possible that you could sit in our conference room at home and just run your camera from here?” Because that would be amazing. Like, Dad’s going to go upstairs, leave him alone until the game’s done. And then poof, he just walks down the stairs and he’s done.

IVAN: And he’s done, yeah, that would be pretty cool.

LYNN: It would be awesome. But, I think step one is shooting without anyone in the crowds and seeing how that happens. Because I think honestly the players are more at risk likely than the crew. Everybody would be, but the players are sweating and spitting, and all that kind of close contact would be more challenging for them. So, they could create a safe space for them. I think that’s the start.

IVAN: I think you’re right though. I think there isn’t a way to replace or for crowds watching an event like that to go away. We are fundamentally other-people-based. We’re community-based. We want to be in a place where there are other people watching something that we could all support and agree on. And team sports are a wonderful way to do that. So, I can’t imagine not being able to go down to the Target Field with my son and my daughter to watch the (MN) Twins play. That would be hard.

LYNN: It would be.

IVAN: Yeah, yeah.

LYNN: And, they’ll probably find different ways to have a private group chat on your screen while you’re watching the game at home, so you can talk about the game with your friends, but only your friends. Or, I think it will take apps and social media into a whole new sports venue that we haven’t seen.

IVAN: Yeah, that’s true. That’s true. Great insights. It’s been so awesome to talk to you. I’m glad that you’re happy and safe and got kids with water-filled keyboards. [laughing] Thank you so much for spending your time with me today. It’s been great.

LYNN: Yeah, thanks for having me as always. I really enjoy it.

IVAN: Lynn Winter is a digital strategist and the founder of Manage Digital, a conference for digital project managers, happening this August in Minneapolis. She’s online at and she’s on Twitter as @lynnwintermn. And of course, Manage Digital has its own website too. You can check that out at 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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