The Leadership Habit Podcast Minisode Series: Work Fails

Hi everyone, it’s Jenn DeWall and I am so excited to announce that The Leadership Habit Podcast is starting a new series of minisodes about Work Fails, Work Fails! We’ve all had experiences when things did not go as planned in the workplace, but people don’t talk about it. And great leaders know that failure is a part of life and eventual success depends on how we handle situations and learn from them. So we decided to talk to people about real-life examples of when things didn’t go as planned, to understand how they handled it, what they learned from the experience and what advice they would share to help others that may be facing similar situations or to help them understand maybe potential pitfalls to avoid or prevent the same type of work fails that they may have had. Today we are talking to Jenny bridges, Marketing Director at Crestcom. She shares with us her work fails from her career in event planning and her time at a marketing agency. Enjoy!

Marketing Director Jenny Bridges Shares her Work Fails

Jenn DeWall: Hi, everyone. It’s Jenn DeWall and I am so excited to be talking to Jenny Bridges today! We are kicking off our leadership series on work fails. Jenny is here today to share her experience of failures that she’s made throughout her career, mistakes that she’s made, how she’s learned from them, and how she has overcome them. So hopefully, you can learn from her to either avoid maybe making those same mistakes or at least not give yourself so much of a punishment for making them. Jenny, thank you so much for coming on the show. We are so excited to have you because we know that every leader has a fail. We all have work fails.

Jenny Bridges: Oh, yes, I’ve had plenty. I think from every career I’ve had, there’s always, whether it’s major or minor, there’s still something you can learn. So I don’t look at failure as this big blown up cost- your-job type of mistake. I think I look at it as I could have done better and I have a learning from this. Take that learning and then move forward.

Jenn DeWall: I love that! It’s about looking back and saying, “what could I have done better?” And I know that that’s something that you and I are relatively around the same age, so we’ve had a few years in our careers to at least see that things do get better. But to those that are listening, that are new in their careers, know that this is an opportunity to learn from someone that’s already been there. So Jenny, what are your work fails? I know we’re going to talk about a few on the show, but which one stands out for you or which one would you like to start with?

Event Planning Goes Awry

Jenny Bridges: I have a few, and I always try to think of trying to build up upon it. I did event planning, my gosh probably 10-12 years ago, ten years ago at this point. And if anybody knows event planning, it’s a super, super stressful job. I think it ranks in the top 10, like one of the top 10 most stressful jobs there is. Which sounds funny, because I think people always think of event planning as like, Oh my gosh, it’s this sexy job. Like you do put on these big productions and all this stuff and it’s like none of that.

Jenn DeWall: You think of event planning like, it’s so fun. You get to do this, and you get secret access in these events –

Jenny Bridges: It’s all the glitz and glam, and it’s so much hard work behind the scenes. I always reference it like a duck on water. Like you look really calm on the surface, but like underneath you’re like legs are going a hundred miles an hour, you’re super stressed out. And there was travel on top of it. So that made it also super stressful. So one small fail I had which I’ll start with that and like build upon as I did an event out in Oakland, but I had to drive from Bakersville to Oakland. So that’s like a six-hour drive. So I’m trying to remember – I flew in early, I did an event, and then I ended up driving late and got to the hotel at like 10:00 PM and part of our job- it sounds minute- but it’s like printing name badges. So we carried these like little name badge printers with us and it’s a big deal. Because if you’re trying on-site, you can’t really go drive somewhere and print them off, so you always just bring it with you. So you bring a lot of stuff. We call ourselves schleppers. It’s like you carry all of this equipment. You bring like suitcases, and you travel with like five laptops. So it’s kind of annoying to travel with all that. So I remember it was like maybe 11:00 PM or something and I was getting ready for the morning so I’d be there at like 7:00 AM and then I was going to print the name badges. There’s probably like 200 so I pulled out the printer, I pulled up my computer and then we had like these little travel kits with us. I have all the cords and things we need and I’m like digging through and there’s no cord.

Jenn DeWall: No!

Jenny Bridges: So I’m like, shoot. How am I going to print these name badges? I’m in a hotel in the middle of nowhere. Like I, what am I going to do? So then I started like stressing out because I’m also with my boss and I have to be there at like 7:00 AM. And there’s no like FedEx or print place. And they printed really weird on word docs, and you had to peel them off. So I was like, I don’t want to like just do the names like handwritten, which I could have done at the end. So I basically went down to like the front desk and I was asking them, do you have like a computer?

I don’t think I had a laptop back then, but I was like I just need to get on your word system. And had to ask the hotel staff to let me get on their computer, and then I was able to print off the Name badges. So it sounds like not a big deal but it was like 11 o’clock at night, I had been up for what felt like a day and a half and I was able to print it. But the fail was like you’re super detailed as an event planner and you always have to make sure you have all of your stuff. And that’s like one of my biggest pet peeves is not being prepared and I didn’t double-check that kit. Our front office person always packed it. I didn’t check for it. I just assumed it was in there. So the hard lesson for me is like always double-checking everybody else’s work or just what they’re packing. So it’s just not relying on everybody. I think for me, it was like not relying on anybody else saying they did it just to make sure. So like for me, I just, every event after that, I had like triple checked everything, especially if you went overseas because you can’t go by like those certain things out there. We even took a big name badge printer with us to Columbia because of reasons like that. So it was super stressful, but it went fine. So for me, it was just more of just like failing at my job and making sure that I was prepared. So it was a little fail. So yeah, it could have had bigger consequences to show up and not have any name tags for 200 people. You’re like, “sorry!”. That’s like the first thing- event planning 101, right?

Jenn DeWall: I’m sure there are plenty of people that are listening to this that can think of how they might’ve made one small mistake, or they might’ve forgotten to double-check something. But then the consequence of not doing that ended up just increasing their stress tenfold and pausing that shift into panic mode when you know maybe for the next time if they could if they did do the triple-checking and looking at that, and they could hopefully alleviate or avoid that in the future. That’s a good one because we can beat ourselves up for that.

Jenny Bridges: And I think it’s simple, and it’s easy to overlook those types of things, and it’s just more of just being prepared and accountable for yourself to make sure those things are there. Because it’s easy just to trust everybody else is doing their job as well as yours. And so it’s just like a small oversight but can have like a big impact is kind of how I looked at it.

Jenn DeWall: If you’re the one that has to take full responsibility for something because you’re the one that’s going to the event, you have to take responsibility for ensuring everything is there, too.

Jenny Bridges: It would kind of- it’d be my fault. I wouldn’t be able to say like X forgot to pack it. Like that’s my job too.

Jenn DeWall: So I think there’s ownership in there too. A lesson about ownership of what we do own versus how sometimes it’s easy to point fingers. And at that moment I can only imagine the frustration that would’ve come with being like, why didn’t they just pack this one? I’m so frustrated. But then at the end of the day, you’re the one that’s ultimately responsible for doing it.

Jenny Bridges: Well. And if anything about leadership, in general, is like a big part of that is accountability. Like and saying like I have a piece or a part in this and I own it. And so I think you always have to own those things and be able to say like, yeah, I made a mistake, learn from it and then like move on past it.

When Problems are out of Your Control

Jenny Bridges: So this is a crazy story. The next one. So I’ll try to like truncate it down cause it’s kind of long. But I’m in the same place I was doing event planning for before, and I had a client out in California and we were doing an energy company’s event. So we were out in the Redwood Forest, setting up an event and doing lunch and then a tour of the facility.

There was no cell phone service. So my bosses couldn’t get ahold of me. It’s just a co-event planner and me. And we had a tent company come in and set up. The lunch is going on and then, I can’t remember what point of the day my client came to me and pulled me aside and asked me, “you hired the tent company, right?” And I said, “yeah.” And he’s like, “are they a reputable company?” And I was like, “well, yeah,” I just got them from the list of vendors in California for event tents that would actually come up into the forest and set the tents up. And everything, you know, it’s fine. I asked the client what was going on, and he told me that after the tent company left, the drivers went back down the mountain. There was a school somewhere, like a middle school, and they had stopped to use the restroom and had harassed one of the teachers there.

And so it was like a big deal because the company that we were doing the event for, didn’t want, doesn’t want bad press. They’ve had experiences with that in the past. So even though it had nothing to do with us in general, but because I had hired them, it was this big issue. So I asked the client, “well, what do you want me to do?” It has nothing to do with our event that is taking place. It was just more of ok, let’s control what we can. So my concern was making sure he was okay with everything and then making sure the event went smoothly and that nobody knows what’s going on. So he’s agreed, “let’s just focus on the event.” I think he was more worried about like bad PR for their company even though it technically wasn’t tied to the event specifically. It was just the association that I hired them. So the event went great. Like no issues. Great. So I didn’t call my bosses during that whole thing. My job was to make sure the client is happy and the event is taking place and the attendees are taken care of. That was my focus. And working with my counterpart that was supporting me.

So we get done with the event, we go back down the mountain by bus with the clients. The air conditioning on the bus breaks- also can’t control that. So with all that stress during the event, and then that happens. So we have the driver stop at a gas station, get water, and it was really hot. It was the middle of summer, and it was just one of those things where you think, can one more thing happen, you know? But they were all really nice and in good spirits. When we finally got back to the client’s office, everyone was like, thank you, for everything. It was still great, so the mood was positive, right? But then as we were getting back down the mountain, my coworker was like, “the two owners are calling me- and they are pissed because they had heard about what had happened.”

So they were really upset with me that I didn’t call like stop in the middle of that and called even though I don’t know what they were going to do about it. So they said it was like,

Jenn DeWall: You didn’t have cell reception anyways, right?

Jenny Bridges: Yeah, well, I could’ve found one- there was a phone on site. So we had to take the red-eye back to Colorado and then I had to be back at my office at like 7:00 AM, and I got like an ear full of how it was my responsibility to tell the owners what was happening. If there was bad press that would’ve leaked. They said that for some reason, helicopters were flying over the event. So there was just like all this upset- and it was one of their preferred clients. So there was just all this pressure for them to want to handle it.

So I looked at it as a fail because maybe I could have alerted them. You know, in a way, I’m not sure what they would’ve done at the time. My job was more about responsibility for the client and the customer experience at that point. But it was more like something I learned in the client relationship space was just like they come first- but also even though I sometimes think other people don’t need to know something, maybe they do from that standpoint. But you know, it’s hard too because I had to learn a hard lesson from them and the responsibilities they look for, and they’re like lead event planners. So just a really strange like event to like try to like handle. And make sure the guests got taken care of, the client was happy. And then to have something completely out of your control like happen.

Jenny Bridges: And it’s a weird thing to have happen, but nothing like came out in the press about it. For the client, you know, there was all this like nervousness of it, but like nothing happened, but it was just more, they looked at it like I fail to like bring them into the conversation and like handle it even though in my head I had handled it. So for me, it was just like, okay, you know, next time like consider those things and maybe make a five-minute conversation or call to avoid like the conflict or what I had to deal with when I like got back.

Jenn DeWall: Yeah, there’s a lot there and especially when you don’t have the jacked responsibility because of the things happening out of your control. But it sounds like there’s also that little bit of a learning of,

Jenny Bridges: Okay, when I, as I can tell high-pressure situations, how do you handle them?

Jenn DeWall: Or also how do you take into consideration the point of view of another party when you’re making decisions of understanding that to you? Like everything was under control, but then maybe if you were like, wait, how could they potentially see this? But you don’t know that. I think that’s also tied to our ability when we’re earlier on in our career, I don’t think, because college doesn’t prepare us for this I don’t think we’re conditioned to think about big picture things.

Jenny Bridges: You’re just in the moment. You can’t think like past like, well if I don’t do this, this, this. You’re more likely just thinking, what’s my immediate job right now? That’s how I thought at the moment I’m not like, Oh well, what technically could happen? Cause it’s too stressful, I think.

Jenn DeWall: Yeah. And so taking that big picture thinking, you know, if you are in those situations where something does happen out of your control, maybe then asking the question like who else would potentially need to know this or be bothered if they didn’t know about this. And we use that and the more that we ask those questions about who else are we serving, the more that it can help us.

Learning from Your Mistakes

Jenny Bridges: And that’s kind of how I looked at it like from their perspective. But it took me a while to get there because I thought, given the circumstances like it was handled really well. So I did struggle with it at the time because I don’t feel, I didn’t feel like I did anything wrong. But then when I, I think even when I reflect back now or it’s like after I left that job I was like, well from their point of view they probably want to be able to handle like higher-level conversations or press if it came their way. And so I think they felt like it took so long for them to find out mostly because there wasn’t cell service. And other things happening that they wanted to be like at the forefront of it and not reactive. So for them to be able to, like if somebody would call or said something, why we were still at the event, they were like, they knew about it. Not like what, I don’t, you know, it wasn’t coming out of nowhere. So I got that. But I think other underlying circumstances made it harder. Just maybe the way they handled the conversation and things like that that made it difficult versus like, Hey, great job in handling a very stressful situation that like is very weird. Like that’s just like a weird story, it sounds like I made it up but that was a strange experience. But I finally understood kind of what their point was. So now I try to think of what I’m trying to handle. Certain things like am I the last person that needs to know or like who in the circle might need to know to your point of like they might, it might help me if this person is informed of X. Does that make sense?

Jenn DeWall: Yeah, absolutely. And how do you think, I mean emotionally I can only imagine coming back and just the.

Jenny Bridges: Terrible.

Jenn DeWall: Yeah, how conflicted you probably were, how frustrated you probably were like knowing like, Hey, I think I did everything that I could, but now.

Jenny Bridges: I was deflated, I feel like at the time. And it was probably because we took the red-eye and got back so late and then you get up and then you know, you’re going in to have a really hard conversation where you’re not being, it’s more of like you’re looking at them, they’re looking at you as like you’re at fault. You didn’t do enough when you really felt like you did the best you could for that very weird scenario. So it’s hard at the time.

Jenn DeWall: It’s a difficult spot. I know you have one more fail.

When You Just Didn’t Listen

Jenny Bridges: Yeah. This one was a past job where I worked at an agency and I think I just like track this one up to just being able to listen and you know, we were trying to produce a video for a client, and they weren’t very comfortable spending a large chunk of money on a brand video and we just kept trying to drive like our story home and then we thought we knew what was right and that, you know, part of your job working in marketing agencies and still be at the client and you know, in a way help them understand that you really do know their business at the end of they, they know their business better than you. And I think we kept wanting to sell an idea so bad that we weren’t really listening to the things that the client was saying that wasn’t working for her. And so I think it was my responsibility as like the client lead to hear her and understand that she was telling me even it might’ve been like subtle that this is not what she wants. And we kept forcing the idea and then we didn’t end up doing the video at fry, the relationship with the client. I think it affected me and like my ability to like, like do that job well with that account and grow that account kind of went stagnant and then that relationship was kind of frayed and that’s where the first time and like the, you know, for years I worked there that I felt like I had made like a big mistake with the client.

So it was really hard to go through that. And with her, I’d have a lot of conversations where I had to basically, what’s that term, eat crow? What is it that people say? When you have to like basically like eat your mistake and be like, yeah, I messed up. I didn’t do right. You know, so I had to have two conversations with her. I basically had to, and that’s hard just to be like, yeah, we’re, we’re wrong. You know? And she did have a role in it for sure. But like our job is to like listen and be able to know when to say like you’re right, let’s move a different direction. And that, you know, it was hard to do that cause I blamed mostly myself even though there was a team of us for not being able to hear that. So that was a hard pill to swallow.

Jenn DeWall: What do you think the takeaway would be? I mean the one obvious one I think is maybe, you know, practice being an active listener and especially if you’re in a situation like that where you’re solutioning like listen, so you can grab that key information instead of maybe because I think sometimes we get so excited about our solution that we don’t necessarily want to hear it because it doesn’t align with our solution. So it sounds like there’s a few different lessons. Like there’s listening, there’s a little bit about suspending our ego to trust that like, Hey, maybe this is a learning opportunity. It’s not an opportunity where our expertise is necessarily relevant based on what we’re hearing.

Accepting Responsibility and Moving On

Jenny Bridges: I think that a lot of that is relevant. I think it was, you know, active listening. But I also think it’s really hard when you’re trying to actively listen to a client that isn’t super direct because they’re not telling you- don’t do this. And then when you did ask questions, they still said yes. So that’s where a lot of the water, I would say it was muddied with that circumstance but knowing like you know how long the process got drawn out, there were more like little clues in there. I should have been more aware of them that I wasn’t looking at. So I think you know, slowing down to like we were trying to like build in this tight timelines. There was a lot of like little points where it’s like if I would have slowed down or if I would’ve brought in maybe like other senior leaders to have conversations and you know, kept trying to, like I kept trying to just drive it instead of just take a step back and be like, I don’t feel like this is right. I think there were like other things I was maybe ignoring to your point of like we didn’t want to hear it because we wanted to do the project so bad. And it’s hard because that’s your job like as anybody in client relations is an advertising agency, your job is like the client and the partner in listening and relationships. So when you make a mistake in that area, it’s kind of like, it’s hard to swallow and be like, Ooh, that’s my job and I didn’t do it very well and it affected the relationship, you know? And I took a lot of blame on myself for that and then I kind of actually reevaluated like should I step away from that role for a while because you know, and that was the only mistake that I felt was like a big one in like, you know, five years at that place. So that was a hard one for me.

Jenn DeWall: Did you end up stepping away from that role?

Jenny Bridges: No.

Jenn DeWall: I think that’s great because that’s, you know, there’s also the piece of we all are going to make mistakes, and at the moment it might feel so uncomfortable that all you want to do is leave that role. But trust that it does turn around, that there is an opportunity to learn from your experience and modify and keep going and find success. Would you agree with that?

Jenny Bridges: Yeah, and I think, you know, I was really hard on myself at first, but then you, you know, you peel back a little bit, and you understand you can’t control your clients anymore. That you can control all your things, so like you can only do so much. And you know, we did, we did have a lot of conversations suggesting other things and trying to like, you know, make it right and have different ideas too. You know we had, we said we owned it, you know, and that’s a lot of agencies won’t do that either. So, you know, I think we did meet them halfway to try to course-correct. And that in the end, it just didn’t work out. And sometimes to have that happens, it just, your relationship with other clients phase-out. So it’s just harder to like have that happen when you have like a really good relationship before. But that’s the nature of like that the agency world anyways. So.

Jenn DeWall: You shared so many great tips and tools. Hey, but we all make mistakes. That’s the whole point of this series is to show people that mistakes happen. But there are always lessons that are mistakes that when we learn from them, we can be that much higher successful, have a greater impact down the road. And you’ve shared quite a few different ones from preparation to, you know, thinking about the big picture and who would need to be involved to slowing down to listening.

Jenny Bridges: It’s a good summary.

Jenn DeWall: You shared a lot of great insights. I think just reminding ourselves that we all need these little messages. We know that listening is important, but here are the things, here are some of the consequences that can happen when we don’t listen. And how can we all learn from you to be more informed when we approach something? Because every person that we meet is our teacher and student, and we can all learn from each other. So I thank you so much for being vulnerable and sharing your work fails because we all have them. It’s not a matter of whether we have them; it’s just a matter of how we deal and learn with them. So thank you so much for sharing your story.

Jenny Bridges: You’re welcome. Thanks, Jenn.

Thank you for listening to today’s Work Fails Minisode! If you enjoyed the episode, please share it with your friends and family. And don’t forget to write us a review on your favorite podcast streaming service. Until next time!