Minisode 5: Work Fails with Leadership Development Strategist Jenn DeWall

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In this minisode of The Leadership Habit, we turn the tables on our fearless host, Jenn DeWall and let our Video Specialist, Christian Wearly interview her about her career missteps and work fails. Listen in as they discuss lessons Jenn learned the hard way early in her career!

Jenn DeWall:                      Hi everyone, it’s Jenn DeWall, and on today’s episode of The Leadership Habit, I am going to share with you my work fails. This is a different role for me as normally I’m the one that’s interviewing the lovely people that we have on our show, all of these experts, all of the contributors. And so this is definitely a different space for me to be in. But for those of you that don’t know, I work for Crestcom as the Leadership Development Strategist. And I’m also a coach and speaker, and I’ll be sharing some of my “work fails” that I’ve made during this portion of my career, but also in past parts of my career. So, and today I am lucky enough to be interviewed by Christian Wearly. Okay, well, Christian, I guess here it goes!

Christian Wearly:              Yeah, welcome to the hot seat. This is how probably everybody else feels,

Jenn DeWall:                      It’s uncomfortable to be here.

Christian Wearly:              So you’ve asked everybody about their work fails and kind of how it shaped them in their career. What would be your- what is one of your work fails that really changed your perspective and how you’ve gone forward in your career?

Jenn DeWall:                      Yeah, I think, you know, I’ve definitely had a couple, but I would say that my work fails, the ones that come to mind are the ones that ultimately led me to pursue coaching and leadership development and speaking. Because if you had asked me right after college, I thought that my career was going to be living and breathing in retail. I had worked in a buying office of a large retailer, and you know, you’re talking about like corporate America. I was totally bought into wanting to climb the corporate ladder. I wanted to do it, you know, as fast as I possibly could. There was no time of like, Hey, let me just figure out what I could learn because I was just maybe an overly ambitious 20-something,

Christian Wearly:              Which I think everybody is.

Jenn DeWall:                      Yes, right? I was like, I need to get promoted. I needed to get promoted, and I need to get promoted. And I think that eagerness, that just kind of like thinking that I didn’t need to pay my dues or I didn’t need to understand that bigger picture really kind of was something that then I would say was the start of an uphill battle, move forward with and my buying career. So I was a little bit more, I would say entitled, definitely entitled thinking that I, I, you know, I had a little bit of an inflated sense of ego thinking that I should get it. And rightfully so. Like at that point in time in the career, like I had had two successful promotions, and so I would say that stroked my ego in the same way that like, you know, you had shared in your work fails. So I was feeling pretty good, and I remember going into my third promotion again, so excited.

Jenn DeWall:                      It was such a great opportunity. I had gone through all these interviews, and I went into this, and I remember the individual that interviewed me- and they asked me before going into it to pay special attention to this interview to make sure that I truly thought that the person that was interviewing me would be a good fit for me as a boss. So to try and say that in a different way. I was being interviewed by who was going to be my boss, but their boss was telling me to make sure that it was a good fit.

Christian Wearly:              Gotcha. So here’s a red flag. Should be aware that this person you’re interviewing with…

Jenn DeWall:                      The person’s boss is already saying like proceed with caution, but I didn’t, you know, I was too excited. I wanted to get to that next promotion. I knew that this was going to give just more visibility in terms of the brand that I was buying, and I wanted that. I wanted all of the fame that came.

Christian Wearly:              Sometimes you look past, you know, the pitfalls and you just look at your end goal of I want to be there.

Jenn DeWall:                      Yes, yes, that’s exactly it. And so fast forward, I interviewed, of course, I report back to this person and say, no, no – I think that we’re going to do just fine. And a few weeks later, a month later, whatever that was, then they extended the offer to me, and I started my next, my third position with that organization. So really excited again, feeling really good because I was attached to this big brand and early, early on, right when I started, I basically had zero support. I like to equate it to this boss was like, hey, I want you to do this, but I’m not going to give you an insight on how I want that done, even though you’ve had no exposure to it in the past.

Christian Wearly:              Oh, nice.

Jenn DeWall:                      And so my initial, first I would say like a few months on the job, I was working extremely long hours. I was working every single weekend I would be going into the office, and I was just so frustrated and just fatigued. And so I go into this VP’s office, and I just tell him like, I don’t know what to do. Like, I can’t handle this. I basically have a breakdown in front of him. And that moment why that’s so important- is that moment where I had the breakdown saying that I couldn’t do this, that I was actually really frustrated with this boss, that they weren’t a good fit, yielded a response from this VP, kind of like, well, you’re the one that asked for it. And because I came up and showed like my emotional side and was so frustrated, then that VP also made different assumptions about how I manage my business.

Jenn DeWall:                      So the perception that I created in the early formative part of the relationship that I have with that VP started out on the wrong foot, and it started out so far away from the right foot that it actually just killed my career the second that I started. So that third promotion was essentially the death sentence of my career in retail. But I wanted to keep doing it. Keep doing it. And why that piece matters is that I think that the first lesson that I learned in the “work fail” is understanding how to articulate your emotions in a way where you can be heard, but also in a way where it doesn’t overshadow, or it’s not going to lead to them seeing the wrong things. Because sometimes, when we’re not in control of our emotions, that’s what can happen. And that wasn’t the perception that I would ever have wanted to create it with that VP.

Christian Wearly:              Right.

Jenn DeWall:                      Especially if I had known that he would basically never promote me again.

Christian Wearly:              Here comes crying Jenn again, oh my gosh.

Jenn DeWall:                      Right. He will never do that. And it’s, you know, and you go forward. And I went through that career, and I still had that same, just high ambitious attitude, like I wanted to get going and I knew that I was doing a good job in my role and so I kept doing these things, but I had already essentially damaged that relationship. I couldn’t do anything right and in that sense, because it was already done, nail in the coffin, like that exchange right there of showing that that’s all that he needed to know. It didn’t matter what else I showed him, and I went, and I went in, and I ended up doing really, really well in that role. I, you know, I felt like we did a great job of managing our sales. Then I went into managing a different brand, and we did a great job, and I was all still under that same VP. And so fast forward after I made a switch, then I got a little bit more, I would say like I really, I knew that I wasn’t going to get promoted right away, but I started to see my peers getting promoted and so I’m like, I need to be part of that. Like I don’t want to be the one that’s left behind. Like I need to constantly be moving. And so then I go to my boss, and I’m like, going into this one on one meeting. And I think that this is the perfect time to essentially ask him about when I’m going to move on to the next level. And so, you know, I’m saying to him like, okay, like I’m really ready to like move up to be a planner now. Like this is going to be great. And he just kind of looked at me like Jenn, that’s not going to happen. I’m like, what do you mean? Like my business is really good. I’ve obviously done this for sales. Like how could you possibly not promote me? I’ve got all of this data to show just how great I was. Not a lot of humility. And he shared feedback that wasn’t ideal. He, you know, I guess the perception that I had created within, you know, the department that I had worked in – I laugh a lot by nature. And so one of the pieces that I got out of that conversation was that if I wanted to get promoted, I really needed to start walking around the office with back up straight, no laughing outside of our cubicle.

Jenn DeWall:                      And you know, there’s other feedback within that same conversation that said, you know, Jenn, like we really just need you to focus on being more of a yes-man or we need you to be more vanilla. And why that piece was again, another turning point is I heard that feedback and I again had a very poor emotional response. I became very, very defensive. Whereas in all honesty, like I know that my boss at the time was genuinely just trying to help me. He obviously didn’t craft his language, I would say in the best way, but he had a really good heart about it. He was genuinely just trying to figure out, okay I know that it’s important to you to move up, but you need to fix some things before we can see you in that light. And what I grabbed onto is he said that I need to be more of a yes-man and vanilla, and those are all things that I can’t change, so I guess I’m stuck.

Jenn DeWall:                      So I just developed an attitude. I developed, you know, frustration. I became a little bit more of an angry employee, and I think I rebelled. Like I became really frustrated and resistant to making the changes. And then, I also personalized it initially. Like I was really frustrated with my boss at the time and just like did not like the VP, I didn’t like the boss because I knew the VP was still at going into here. And so fast forward, I guess to like those mistakes, like the mistake first being too open the mistake, second to being… I would say not receptive to feedback that was really meant to help me. Like so, not assuming positive intent both caused more fray, which eventually just led to me never being promoted. And at that point in time, I had to stay in my position because the company had already invested in me because I was, you know, I was on the fast track before this happened.

Jenn DeWall:                      Like all of my past leaders, they had believed in me, and the company had just accepted me into their master’s program. And so it was the complete opposite of the fact. It was kind of like all these people were really supportive, and then I had all these people that were like, you are not good enough, or you’re not this, or you’re not that. And I’m really grateful for those mistakes. And I think that’s what ultimately made me go to coaching is because I was basically stuck in that position for four years until I could graduate. They would reimburse the college, and I could leave. Otherwise, I just didn’t have the funds to be able to pay for that out-of-pocket just because I was upset with the job. So in hindsight, these, these mistakes that I made, you know what I would say to anyone that’s sitting there is that if you’ve done something that’s maybe you feel is jeopardized, your ability to move forward or get promoted know that it’s totally okay to like change organizations.

Jenn DeWall:                      But if you do want to stay within your organization, you do have to take ownership of how you show up. You have to completely take responsibility that even though, for example, in that feedback session where the word choice wasn’t that actionable like I don’t know how to be more of a yes-man. Like that doesn’t mean that doesn’t translate into something that I can, how I can be better in my natural words. I’m like, well, that just sounds like I, I won’t challenge things so that I won’t be an effective problem-solver decision-maker. But learning how to manage your feedback and learning how to it before it comes out of your mouth. And what I mean by that is- filter, ask yourself, is this feedback designed to help me? And if it is like how can I process it in a way that’s helpful versus a way that’s hurtful?

Christian Wearly:              Right.

Jenn DeWall:                      And if I say that the feedback’s not helping me. Then giving myself permission to let it go. But also it doesn’t mean that by not agreeing with the feedback that I have to be disrespectful to the person that’s giving it. So I think taking the ownership for what you can do, how you can improve and not being so emotional or so just kind of expecting people to like roll at your feet to figure it out. Because that’s just not the case. That’s not how any organization is designed. They’re designed to be able to keep moving forward. So my work fails, again, it was probably being too ambitious and not really allowing myself to learn from all the levels. And also the work fail of the red flags were all there. All of this could have been avoided. I could’ve still been probably like moving in a career of retail had I not just been so ambitious about getting this visible job that everyone in the company could see or like in the buying world could see when it obviously came with some huge red flags. Like I should have just been like, hey, my time will come. Like I can be patient. I don’t need to take this now. Like trust that this is the warning that you need, that you can handle it a few more months just to not see how this warning is actually going play out.

Christian Wearly:              And sometimes I think that’s hard, you know, is you’re early in your career, and you’re so focused on moving up, you’re not thinking of why should I move up? You know, are you asking it? I want to move up, but should I?

Jenn DeWall:                      I know, and why do I want to move up? I think I still think that even the position that I wanted, because that would’ve been the next position is not even a position I would’ve wanted to do, but it would’ve still meant a promotion. And in the eyes of corporate America, corporate America, and how I saw it, I always felt like I was failing if I wasn’t being promoted. And so when my peers started to get promoted because they would put you into these classes when you’re going to go to the next level and then you would kind of be trained on that next position. So as my peers started to go through these interviews and started to get accepted into that process and then you know that they’re part of the prep group or like this, you know, it’s kind of that, that elite group, I guess that all of the competitive type a people in corporate America are looking at and want o to be at because that was me. I wish I would have just been like, and it’s okay that I actually don’t want that, and that understand why I wanted it. Like I wanted it because I was in some way wanting to show people I was good enough that I was there, but I didn’t want it for any other reasons to actually want to do the job.

Jenn DeWall:                      I just wanted it to show people that I was just as good as that I’m just as good as you. And so really I think, you know, as I’m talking about all of these work fields for my first career after college, I’m just thinking, so many of my missteps in my career were all made by having too much of a little bit of an inflated ego or higher sense of self. And that’s hard for me to say today because I, you know, I look at it today, I’m like, who does that? And I’m like embarrassed I did that.

Christian Wearly:              That was me!

Jenn DeWall:                      That was totally me, and I just have to own it. That was who I was. But also understand that that way of looking at my career actually it was just not helpful, and it ended up causing a lot more crying, a lot more stress, all of that. And all that I really needed at the end of the day was to just know how to love myself and validate myself and know my value. And I think if that would be the thing that I would say to anyone is, you know, stop comparing, stop letting your ego drive your career and just start focusing on what really matters to you, not what matters, what you think matters to someone else about your life. Right.

Christian Wearly:              Because most of the time you know it, they’re not paying attention to your career path.

Jenn DeWall:                      No. And they’re not the ones that have to work it. I’m the one that needs to go in day in and day out. Like I would’ve hated that job that I wanted to be promoted to. So they had to like, this is something that for a good two year period, I was just incensed. I was frustrated. I was sad. I was for all of these things, all for a job that I didn’t want. But because I couldn’t have it, I wanted it more. And I didn’t give myself to say like, it’s okay that you don’t want that. Drop the rope, like don’t pursue it anymore. And I think people still do that in their careers. Sometimes they stick with something even though they have all of the red flags. But they are like, you know, especially if it comes down to the competition that I had set up, like showing that I was good enough to, I could get promoted. This race is against yourself. I was making up these fictitious competitions all to like tell myself that I was good enough. Like you have to be the one that says I produce value. I like these things. I can honor all these things about myself, and I can also do the same for the next person. Like we should not be the same.

Christian Wearly:              So Jenn, do you have any other work fails that you might be willing to share with us?

Jenn DeWall:                      Oh my gosh, I have one that I just, I really want to share because that’s one that it was so blind, it was so innocent. I love to laugh. I love to joke around, and I love to socialize with you that you’re my peer, and I love to connect with people. And I was doing a role in HR for an organization. And one thing to know when you’re in HR is it’s a pretty, I would say, visible position. Meaning people know who HR is for the right reasons or wrong reasons or all the reasons, but they know when HR is in the room and they-

Christian Wearly:              Yeah- hold the jokes,

Jenn DeWall:                      Right- can’t do anything here, and they kind of perk up when HR is around. And not necessarily because they’re interested in me, but it’s kind of like, okay, what are they going to say? What are they going to say yes to your best behavior?

Jenn DeWall:                      Yeah. And I was just walking around as I would like. I would kind of walk the floor, go around, and just talk to the different departments. And I was on the it side of our business and I was talking to all the people that were there. And there were a few people that I had developed rapport with. And so we were just joking. And it happened to be around the time that we were starting to talk about bonuses, but in the context of this conversation, like this employee that I was talking to, like we just always had more of like a joking, playful, like just having fun at work, relationship, a lot of sarcasm. Nothing that would be, that was ever, I mean it was just, it was just a fun, like, you know, a fun coworker to work with. And in this one specific day that I did not think anything of until after that day.

Jenn DeWall:                      I didn’t know how to think there’s anything memorable. I was just having a conversation, and the is like, Oh Jenn, are we gonna? Are we gonna get just like huge raises this year? And so they’ve, they phrased it to me in the way of a sarcastic question. Like they were like, of course, we’re not going to get like, we know all the reasons that we’re not going to do this. Like because of this performance or we know what this is going to be. But person says, Jenn, are we going to get just like huge raises? And so he’s saying it to me in a sarcastic way. And so then I respond. I’m like, yes, everyone’s just going to get huge raises. I again responded, and I started passing away fast forward. So, you know, conversation reps, whatever, joking around onto my day, not thinking anything of it. Two days later I get a call from our COO. The first, it was the CIO that came into my office and was like, were you telling people that everyone was going to get a big raise this year?

Christian Wearly:              Oh no.

Jenn DeWall:                      I was like, what? Like, no, why would I ever tell people that? Like, no, that’s absolute, I’m not even their boss. Like I don’t determine that. And then he’s like, well, one of the directors, this is actually a director at that organization, heard me say it and then reported it to the chief, um, our chief technology or chief information officer and said that I was going around and telling people that there are these huge races and whether or not that was my intent, because clearly in the context of the conversation, it was just like sarcastic banter, but someone else from outside heard it out of context, made assumptions and then deduce the fact that I was walking around telling people that we all going to get huge raises.

Jenn DeWall:                      I was mortified. I was just so embarrassed because then I also followed up with a conversation not only with that executive-level member but also with our COO. And I just never realized that the weight of a simple joke and how that could have been perceived and how it blew up to what it was.

Christian Wearly:              Right.

Jenn DeWall:                      It’s still something that like, I just wish I could go back and change that because there was just something so innocent and I didn’t think anything of it. But sometimes you know, the higher up that you go in your career or the more visible you are as an individual, understanding that the weight of your words will change the perception that people have of you. And then in addition to those words will have an impact. Um, the higher up that you go, the more that those words matters. You have to be really sensitive to the fact that are sensitive to what you’re saying and how you’re saying it because other people are listening and whether, and they’re not necessarily wanting to take time to fact check to understand they’re just going to fly by the seat of their pants and here’s what they want to hear, hear what they heard and move forward.

Jenn DeWall:                      And that was just a huge mistake for me because I felt like it was something that was just so much of just like, you know what I would consider like an innocent joke but it really did cost and it damaged the trust or the relationship that I had had with these two executive board members. And that was something that was really hard for me to like process because I would in no way want to put them in a bad position where they, you know, where they were, the bad guy or that I would start a rumor though thought we were going to get gigantic raises. But yeah, just understanding that sometimes like what you say, depending on your level, is going to be appropriate, not appropriate, taken out of context and like you have to understand that people are watching and so what do you want to be remembered for?

Christian Wearly:              I was given really good advice years and years ago by the colorist at the post house I worked for, and he said be careful. I had said something kind of offhand about what I was doing at the time. You know the client I was working with, I forget the what I had said, but he said be careful what you say. You never know who’s listening. And it’s like you’re right, is fun not willing to tell that person that then be careful what you say because the walls do listen even though you’re not paying attention.

Jenn DeWall:                      Yes. Why didn’t I have that person in my life before I made this work fail? I wish I had had that sage advice because I think I would have, you know, and it’s funny cause I think I was pretty sensitive to a lot of different things like sensitive in terms of how you’re communicating. Like disciplinary action or how you’re talking about sensitive issues. I think that in so many ways I would say I was actually very aware of what I was saying but in this context because I thought it was just such a joking conversational like off-the-cuff, not even, you know, I didn’t even think that that held true in such a just casual conversation where clearly if you were actually a part of it, you would have realized like there was nothing. Right.

Christian Wearly:              Meanwhile two cubes down, Charlie and Doug think they’re getting huge raises.

Jenn DeWall:                      Jenn’s telling everyone, oh my goodness and now they have to abandon their Teslas and I am just the one to blame.

Christian Wearly:              Just crushed their dreams.

Jenn DeWall:                      It’s so, yeah, I love that. Like I think that what you just shared, that know that people are listening, the walls are listening. I mean people, people hear you whether you think that they’re paying attention or not. Like people are,

Christian Wearly:              I mean it’s natural. I mean when you’re working with clients or you know, whoever you’re always, you know, as a group you kind of want to, I don’t want to say rag on them, but sometimes you know you need the, you know, gang up mentality of you know, Oh they’re so hard to work with. Or when someone down the cube might be on a phone call with that person and they hear you in the background.

Jenn DeWall:                      Oh my gosh, all of those things I’m surprised at like, you know, mine happened the way that it did just cause I feel like there are so many other areas that I was unaware but just be aware. That day sucked that day was just awful. I just go back to that. I, you know, I guess this is par for the course. I was definitely shut my office door. It was like crying cause I was so disappointed with myself because I hated that I let down our COO and I was just embarrassed. I was so embarrassed because I would never think that is such an obvious thing to me. Like, of course, I would not walk around telling people we’re raises.That’s, you know, that’s the way the cookie crumbles some, and I had to own it. I had to own that I didn’t realize that there would be a secondary message that could have been deduced. And taken from that.

Christian Wearly:              Yeah. So own your mistakes on your mistakes. Well, Jenn, thank you for switching roles.

Jenn DeWall:                      I’m glad to be here. Yeah. Like I guess maybe that’s not how you mentioned switching roles, but I love my position here, but it was also fun to switch roles and be on the other side of it. Thank you for me for coming here from behind the production side to interview me. This was fun, Christian!

Christian Wearly:              Once in a lifetime.

Jenn DeWall:                      Thank you for listening to today’s episode of the leadership habit featuring my interview sharing my work fails that I’ve made. I hope that you learn something or in any event, maybe you’ve got some laughs over the fails that I made. If you liked our episode or you feel like you have a friend that maybe could benefit from this, don’t forget to share it on your favorite social media platform or to write us a review.