The Professional Confessional

How Her Mistake Almost Got Her Fired for Being "Dead Right" | Ashley Stryker, Professional Confessional

August 22, 2021 Ashley Stryker Season 1 Episode 1
The Professional Confessional
How Her Mistake Almost Got Her Fired for Being "Dead Right" | Ashley Stryker, Professional Confessional
Show Notes Transcript Chapter Markers

Content marketer Ashley Stryker remembers the "feedback" meeting that nearly got her fired through her own self-righteous arrogance.

  • Ashley's biggest mistake was her (my!) insistence that just because I was correct on a given strategy -- and the strategist presenting was incorrect -- did not mean that I presented it in the correct time or place, or even in the most respectful way possible. My accusations and arrogance resulted in serious harm to my teammates and my boss, which took months to restore to something approaching functionality. 
  • On realizing her mistake, I resolved to learn how to navigate office politics better, even if I felt it was stupid. I needed to acknowledge that we were all working towards the same goal, so I should approach conflicts from a place of confusion and clarification, rather than accusation.
  • Today, Ashley Stryker offers content marketing strategy to clients and employers alike while enjoying implementing her professional skills for her personal projects -- like this podcast! I'm easily reachable through the Professional Confessional podcast website or over on LinkedIn

You can find this and other episodes of the Professional Confessional podcast at or on your preferred podcasting platform of choice.

Do you want to come on and share your biggest professional mistake? Head to to schedule your professional confessional. 

In the meantime, please share this episode with someone you think needs to hear this today -- and share what you needed to hear in a review! The more often we rate and review our favorite podcasts, the more people will find out about our community and the more episodes I can make. 

That's all for this Professional Confessional. I'm Ashley Stryker. Thanks again for tuning in, and I hope you'll join us next time. Talk soon! 

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 [00:00:00] Ashley Stryker: Hi, and welcome to the Professional Confessional: how the biggest professional mistakes we've ever made fundamentally changed our work, our careers, and our approach forever. Gain wisdom and perspective through these audio absolutions. 

[00:00:17] Ashley Stryker: Hi, I'm Ashley Stryker. I'm a content marketer. By now, I've interviewed a ton of really incredible people. It occurred to me that I couldn't publish these personal and painful accounts if I didn't go through the same process myself. 

[00:00:33] Ashley Stryker: I think this is something many people can relate to. I just have a big enough mouth that I did it and I paid the price for it. It's something I still struggle with today. 

[00:00:45] Ashley Stryker: A job at a creative agency. I had been in-house-- that means working in marketing at a company for my entire career so far-- I thought maybe if I got to work on multiple different contracts, I wouldn't get bored; I'd get to learn new things; I wouldn't have to justify my existence as a marketer, as a resource instead of a cost center-- which is, in-house, one of the big things you always have to do is market yourself. 

[00:01:06] Ashley Stryker: I came on board as one of their writers. And to this day it remains one of the best cultures I've ever the privilege of experiencing. And there are many, many lessons that I learned there about how a good company treats its people, about how a team can work together, about agency life, and about balancing what's possible versus what's asked for.

[00:01:27] Ashley Stryker: Basically there were two halves of the agency. One half-- the one that I was mostly living in-- was the creative execution half. We did all of our own graphics, video and audio and writing. I was given a creative brief of what to write, and I would just sit there and write it, and all was right with the world. 

[00:01:48] Ashley Stryker: The other half of the house, one that I was more interested in actually at that point, was the strategic on the client relations side, because this was something I'd never done previously and was hoping that I would get a chance to learn. So I wanted to make friends with the strategy people.

[00:02:04] Ashley Stryker: Oh God, I'm just reliving this mistake and going, I have...of all of the goals that I had, I could not have fudged this up as badly as I did.

[00:02:13] Ashley Stryker: At this time, I was working on a specific contract and the contract was coming up for renewal.

[00:02:19] Ashley Stryker: There were many feedback meetings being scheduled across different departments. It was a, "This is how we're going to pitch us moving forward. We want everybody's feedback in this, whether you are in the strategy and know what the client wants, or if you're on the creative side and you're executing."

[00:02:34] Ashley Stryker: So I was in a meeting-- without my boss, who had been gently guiding me through some office politics. I was on my own for this one. One of the senior graphic designers was in, as well, and one of the copywriters, plus the senior strategist. And, I think an assistant of some sort was with her. 

[00:02:55] Ashley Stryker: So they were running the PowerPoint presentation as a mock up and we were offering feedback. And for the most part, I thought it was an interesting approach.

[00:03:04] Ashley Stryker: And then we get to a slide that has something along the lines of, "...and we're going to form a giant community. We're going to build out our own website forum to allow all of these wonderful community conversations to happen because our target audience happens to feel very isolated."

[00:03:23] Ashley Stryker: At this point, I said, "I think the idea is great. But is that something we can really take on? Should we do that?"

[00:03:30] Ashley Stryker: And she said, "Well, what do you mean?"

[00:03:31] Ashley Stryker: I said, "Well, it takes a lot of work to build up a community, a lot of resources and a lot of dedicated time." 

[00:03:37] Ashley Stryker: Anybody who's ever spent any time in community management online will understand exactly how hard it can be to form a community.

[00:03:46] Ashley Stryker: And I said, "Well, why don't we just partner with the communities who are already there instead of trying to build our own? So that way, we can take advantage of the leverage and the reputation they already have instead of trying to form it."

[00:04:00] Ashley Stryker: I remember her just kind of standing there and blinking and saying, "Well, that's a nice idea."

[00:04:07] Ashley Stryker: I think she was trying to move on. 

[00:04:10] Susie Ashfield: Yeah. 

[00:04:10] Ashley Stryker: In retrospect, I think she was trying to move on. Emboldened, Mistake Ashley goes on and says, "And, while we're at it, why don't we just let them talk about these certain issues that they've been wanting to talk about would enable us to get traction because they're things that the community cares about and we haven't discussed on the blog?"

[00:04:31] Ashley Stryker: This had been something I'd been thinking about anyway. I just saw it as the opportunity to bring it up-- because I was dumb and can't read a room.

[00:04:40] Ashley Stryker: And she kind of half smiles, and tilts her head-- the senior strategist-- and says, "Well, we've already been doing that, dear."

[00:04:50] Ashley Stryker: I can't tell you what I said next. I can't tell you even what the expression was or, or anything. I just remember that perceived condescension. 

[00:05:03] Susie Ashfield: Did she call you "dear"? Did I hear that right? 

[00:05:05] Ashley Stryker: I think so. It might be my memory trying to justify the reaction that I'm about to describe. 

[00:05:12] Ashley Stryker: I just remember, she responded. 

[00:05:15] Ashley Stryker: You know, the saying, you see red? That's like my ears saw red.

[00:05:20] Ashley Stryker: I could hear my heart pounding; the hairs on my arms rose; my cheeks flushed like I had just dragged an iron across them. 

[00:05:29] Ashley Stryker: And I half-stood and said, "I know for a fact we have not."

[00:05:34] Ashley Stryker: Because I had, in fact, been requesting these topics for months. And they had never gotten through. The bloggers themselves had told me, and I had --in wanting to defend the agency at the time-- had gone through our files and our archives to see if I could find the blogs to say, "Hey, we've already done this topic." 

[00:05:54] Ashley Stryker: Couldn't find them. Looked through the backlog of materials; couldn't find them. And so I'm like, "You know what? You're right. And I'll try and advocate for it."

[00:06:04] Susie Ashfield: Yeah. 

[00:06:04] Ashley Stryker: That was not the way to advocate for it. 

[00:06:06] Ashley Stryker: But my brain just disconnected. And I basically told the senior strategist, "This was a dumb idea if we didn't pursue it and we needed to, and oh, by the way, this ties into your broader strategy over here. And, and..."

[00:06:23] Ashley Stryker: And then I just kind of petered out.

[00:06:25] Susie Ashfield: Wow. 

[00:06:26] Ashley Stryker: And the blood receded from my ears. So I couldn't really hear again, other than my wordless scream inside my head

[00:06:33] Susie Ashfield: Of course. 

[00:06:35] Ashley Stryker: And I just remember blinking and I remember my colleagues very carefully not looking at me.

[00:06:41] Ashley Stryker: I remember the strategist just kind of standing there, not quite slack-jawed. She had a certain gravitas. She just said, "Well, aren't you passionate?"

[00:06:53] Susie Ashfield: Oooh. Ooh. 

[00:06:55] Ashley Stryker: And it was about then that my survival instinct kicked in because I had heard "passionate" before. 

[00:07:03] Ashley Stryker: I am a passionate individual. I care a lot about what I do and doing it right. I care. And that gets me into trouble just because I either assume everybody else cares or everybody cares in the same way. And so I just.... as soon as she said that, I realized that I had just punched through thin ice because that had been not used as a complimentary phrase for me. 

[00:07:30] Ashley Stryker: I immediately subsidized. I can't tell you how the rest of that meeting went. 

[00:07:34] Ashley Stryker: And then I never told my boss because at that point I figured I had just stepped in it and I was just going to weather this and she was going to be annoyed. I was just going to have to chalk it up as a lesson. I had forgotten that the actions of one individual would have ripple effects on others, including my boss, who had been an advocate for things that our department had been trying to get done for months, and I set it back. 

[00:07:59] Ashley Stryker: And I didn't tell him because I, again, I thought it was just my screw up. I hadn't realized --maybe didn't want to think about-- how that kind of outburst would impact the team's goals overall within the company.

[00:08:15] Ashley Stryker: My boss calls me in and said, "So you had a meeting with this strategist."

[00:08:20] Ashley Stryker: I immediately realized the error and I, I just told him everything. I didn't, I didn't sugarcoat everything. I was babbling. I was apologetic. I told him I'd sent an apology. I asked if maybe I should go up and do it in person. And, and he was just like, "No! No, please."

[00:08:39] Susie Ashfield: "No, no, please don't do anything! Just stay there." 

[00:08:42] Susie Ashfield: Yes. And we had a talk about seniority. And I said, "It was stupid."

[00:08:47] Ashley Stryker: And he said, "It doesn't matter if you think it's stupid."

[00:08:50] Ashley Stryker: And I said, "You're right."

[00:08:51] Ashley Stryker: We had a talk about good timing. And I said, "But they said it was a feedback session!"

[00:08:57] Ashley Stryker: And he said, "You should know better."

[00:08:59] Ashley Stryker: And I said, "I was optimistic."

[00:09:02] Ashley Stryker: He, of all of the bosses I have had-- and I am on great terms with many of them-- he stands as one of the best I've ever had for trying to work through this. And it was only in the following months when I realized the kind of advocacy he had to do after that point. I don't think my job was at risk and I wasn't ever written up for me. Because nominally, it had been a feedback session and as we dug into it, I had been correct.

[00:09:31] Ashley Stryker: They ended up scrapping that entire portion of that particular part of the contract. I don't think it was because of my outbursts. I think it was just a cost benefit analysis and the client may have not wanted to pursue that. 

[00:09:42] Ashley Stryker: I was clearly not privy to those conversations, having thoroughly torched that particular bridge.

[00:09:48] Ashley Stryker: That actually went on my mid-year review. I was asked, like, "How I can improve?" And I can't exactly remember, but it was along the lines of how can I build better bridges across departments. 

[00:10:01] Ashley Stryker: It was really important to me on a personal and a professional level, because I knew that siloing departments leads to inferior product. You need to have relationships between your colleagues and you need to have an understanding of what they do and what their goals are, so that you can come to them and say, "I need this thing from you, but it will help your goals in ABC ways."

[00:10:23] Ashley Stryker: You can't do that without relationships. And so from a professional perspective, I knew those bridges had to be built. And from a personal perspective, I had to figure out a way to approach things that I found dumb or people or traditions or priorities that were not mine and I thought should not be, and still be tactful to get done what I needed to get done. 

[00:10:46] Ashley Stryker: My boss, he'd been around much longer than I, was crucial in teaching me because I could always go to him, and vent, and then ask how to approach something. That way, we could head those sorts of things off at the pass now. And I formed different relationships with different departments and different strategists, then, and I became a go-to resource as somebody who could execute and offer ideas within the broader strategy. I gained for myself a decent reputation after that, somehow, miraculously.

[00:11:15] Ashley Stryker: To the point where I had my last review with them... I treasure this thing because it says, "The issues we described six months ago, I no longer consider to be a problem. Ashley has grown and is a valued member of the team and we look forward to her growing her career."

[00:11:32] Susie Ashfield: So you, you built some new bridges? 

[00:11:35] Ashley Stryker: I did. And I learned some very important lessons about being right versus dead right. And the correct venue to call people out in. 

[00:11:45] Ashley Stryker: Fixing mistakes isn't like they never happen. When you fix a mistake or you say you will avoid it in the future, it's, it's not that you won't ever commit it again. It's that you recognize that it was, and you try really hard to avoid it. And when it does happen, you can catch it sooner and recognize the steps to take in future. 

[00:12:03] Ashley Stryker: I had to learn to work around that self-made error through personal responsibility and acknowledgment and work really hard because my tendency is to just call bullshit out when I see it and I want things done right.

[00:12:20] Ashley Stryker: And that's something that I've had... not compromised, but learned that other people have different definitions and to think about things as a team. And those are all really important and valuable lessons. So

[00:12:33] Ashley Stryker: I'm not grateful it happened, but I'm grateful I learned something. 

[00:12:37] Susie Ashfield: How do you use that skill you have of calling out BS without burning down the building?

[00:12:44] Ashley Stryker: I actually did it yesterday! I have a client who sent out an email and said, "I love this idea for landing page." He had copied three or four or five other freelancers on this. And so, I deliberately replied back and I literally started my email yesterday with, "So, if I can step out of turn for a moment, how is this a landing page? See, my definition of a landing page is this, therefore, by my definition, this is not a landing page. And what am I missing? What did you like about this?"

[00:13:16] Ashley Stryker: He actually replied back all and said, "Ah! Good catch. Thank you. Didn't mean necessarily this landing page, but I liked this approach for the website design overall," and then listed out some more specifics.

[00:13:27] Ashley Stryker: So because of that, I'm very sensitive to moments where I think somebody is wrong. So I need to take them privately, never in front of other people. I need to explain how I see things and ask them what they were trying to say or how they see things. 

[00:13:46] Ashley Stryker: If I did this really well, I would have reversed it and asked what in the world he was trying to get at before I explained my position. People are much more willing to talk about themselves than they are to hear why you think they're wrong. 

[00:13:59] Susie Ashfield: Now you come at it from a point of view of curiosity, as opposed to accusation. Would you say that's it? 

[00:14:05] Ashley Stryker: Yes. The trick with that of course, is that it has to be genuine curiosity. Yeah. You can't come at it, "Why in the world would you think this is a landing page?" That's sarcasm, and that's just going to get you roasted. 

[00:14:16] Susie Ashfield: Yeah. 

[00:14:17] Ashley Stryker: You have to ask the question that you genuinely want to know the answer to, which was in this case, "What about this did you actually like? Because I'm lost here based on how you frame things."

[00:14:28] Ashley Stryker: So that's a tactical way that I implement it. Like you said, the curiosity over accusation. I like to start big projects-- especially potentially contentious projects, long-term employment-- with a mutual understanding that everybody has the best interests of the organization in mind, a common goal. You have different ways to get there; I'm going to have different ways to get there. If we disagree, it's not because I think you're dumb. It's not because I think that my way is the only way. We disagree, because I think there's a better way to get to our common goal. 

[00:15:00] Ashley Stryker: So it's a reframing of the pushback. 

[00:15:04] Ashley Stryker: Yeah. 

[00:15:05] Ashley Stryker: Because there will be times I'll push back. I push back a lot. It's part of why you hire me, frankly, but yeah. So, so that's what happened. 

[00:15:15] Susie Ashfield: That's your confession? 

[00:15:16] Ashley Stryker: That's my confession. 

[00:15:18] Susie Ashfield: Yeah. How was talking about it? 

[00:15:19] Ashley Stryker: Awful. Oh, I'm glad I did. I'm glad I did it with you because it gives me, it gives me closer empathy to what you guys are going through and I'm asking of y'all.

[00:15:29] Susie Ashfield: Well, that was interesting. I wish I'd been there, you know, just as an invisible presence.

[00:15:35] Ashley Stryker: Do you know? My husband actually steps on my foot. So we might be at a cocktail hour for a wedding and I'll be blathering on about something. And my husband will slowly and quietly just start pressing on my foot. And I'll take that as a cue to try and gracefully pivot away from the hole I'm digging.

[00:15:52] Susie Ashfield: Yeah. 

[00:15:53] Ashley Stryker: I have a feeling. You might've done something like that. 

[00:15:55] Susie Ashfield: No! 'Cause then you wouldn't learn. So I would've just had to let it play out. You live and learn, right? 

[00:16:01] Ashley Stryker: Oh my God. Yeah. Thank you. I owe you one, Susie. 

[00:16:05] Susie Ashfield: No worries. It's been great talking to you. I really enjoyed that. 

[00:16:09] Ashley Stryker: I'm glad. 

[00:16:10] Ashley Stryker: Believe it or not, I actually sent this interview to the former boss I mentioned. He texted me back, quote: "The strategist told me when I met with her that she nearly fired you on the spot. She couldn't fire someone who didn't report to her-- and fire someone for questioning? Come on. That meeting simply reinforced for me that you were young."

[00:16:29] Ashley Stryker: I'm years out from this incident, and I still felt myself break out in a cold sweat as I read his text.

[00:16:36] Ashley Stryker: I've learned from my mistake, what it means for my working style, my personality, my weaknesses, but I still feel shame, embarrassment, and guilt for what I did to him and my team. I suspect I always will. 

[00:16:49] Ashley Stryker: In the end, the big mistake that I had to fix was my own self righteousness and arrogance: Two qualities that I still struggle with to this day, to be honest.

[00:17:01] Ashley Stryker: I thought that because I was correct in my strategic assessment, that that would trump niceties like teamwork or tact or even basic professional courtesy that one person owed to another, regardless of seniority.

[00:17:18] Ashley Stryker: I can't change the past, but the only way I can move forward is to try and learn from it. And when I make the same mistake again-- hopefully not as dramatically, but when I do make the same mistake again-- I'll be able to recognize it right away, and have the courage to be able to stand up and admit that I was wrong, and that I handled it badly, and that I'm sorry. 

[00:17:41] Ashley Stryker: And, work twice as hard to avoid committing it in the future. 

[00:17:45] Ashley Stryker: And in the end, that's all any of us can do when we're faced with a mistake. 

[00:17:49] Ashley Stryker: And so here is my confessional. I hope it helps you. I hope it inspires you that you, too, can move past it and find something amazing about your work and what you do that helps you to keep moving, even when you stumble.

[00:18:06] Ashley Stryker: This podcast, for me, is a way to remind myself that I don't know everything; that I definitely need to keep that self arrogance in check; and that even the most successful of us-- the people that I look up to-- that even they had giant mistakes, huge mistakes that were career changing, that were damning on a personal level, that caused them to just reevaluate everything.

[00:18:35] Ashley Stryker: And yet, they're still the professional success stories that I look up to today, even after our conversations. And, if it can work out for them, then it can work out for me, too. And it can work out for us. I truly believe that. So welcome to the Professional Confessional. Let me know what you think. Talk soon! 

[00:18:55] Ashley Stryker: And, you can I find this and other episodes of the Professional Confessional podcast at or on your preferred podcasting platform of choice.

[00:19:05] Ashley Stryker: Do you want to come on and share your biggest professional mistake? Head to to schedule your Professional Confessional. Again, that's

[00:19:22] Ashley Stryker: In the meantime, please share this episode with someone you think needs to hear this today-- and share what you needed to hear in a review! The more often we rate and review our favorite podcasts, the more people will find out about our community, and the more episodes I can make! When we reach 25 reviews, I promise we'll vote on a special edition deep-dive into a major mistake in history that is still relevant and affects how we do business today.

[00:19:46] Ashley Stryker: Anyway, that's all for this Professional Confessional. I'm Ashley Stryker. Thanks again for tuning in, and I hope you'll join us next time. Talk soon.


"I just have a big enough mouth that I did it and I paid the price for it."
"So I was in a meeting -- without my boss, who had been gently guiding me through some office politics..."
"You know the saying, you see red? That's like my ears saw red."
"She just said, 'Well, aren't you passionate?'"
"So you had a meeting with this strategist."
"Siloing departments leads to inferior product."
"Right versus Dead-Right."
"Now you come at it from a point of view of curiosity, as opposed to accusation."
"I actually sent this interview to the former boss I mentioned."