Content Creation While Employed: Jessica Winder on Brand + Boundaries

Jessica Winder (00:00)
I'm a troublemaker. And so I decided to bring that. It's like, okay, I'm good trouble.

Rhona Pierce (00:05)
I love it. Has there been a piece that you've created that felt like particularly vulnerable or risky for you to share?

Jessica Winder (00:13)
Yeah, so I talk openly about addiction and my own sobriety because I know for a fact that anytime I do a sobriety post, I get so many DMs, literally hundreds of messages from people that don't feel like they can talk about it publicly, but want someone to know that one, they are struggling or two, that they just got sober and they want to talk to somebody about it.

Rhona Pierce (00:35)
You

recently started posting on TikTok and YouTube after being resistant to video.

Jessica Winder (00:40)
My

goodness, for years, and I mean years, people have been saying, why don't you record videos? And I literally would be like, I don't want anything to do with TikTok. And there's so many great people on there that are giving out great advice about the workplace. But I will say what motivated me was the people that are getting fake advice.

people that are out there like actually doing harm, giving out advice that has never worked in HR. So that is actually what motivated me to be like, you know what? I've been doing HR for 13 years. I need to start making videos.

Rhona Pierce (01:11)
All right. Thank you so much for joining me on the pod today, Jessica.

Jessica Winder (01:15)
Hi, I'm so excited. This is going to be so fun.

Rhona Pierce (01:18)
Yes, it is. So let's get right into it. I heard that you are passionate about creating good trouble in the workplace. What does that mean to you?

Jessica Winder (01:30)
So I get this from the famous civil rights leader that talks about trouble and good trouble because a lot of times back in the day, people of color were branded as, you you're a troublemaker. You're like getting in trouble, all these things. But there is a such thing as good trouble. And to me, that means like justice and like doing things the right way. And sometimes you have to do good trouble because what you're doing goes against the grain. It goes against what society says you need to do. It goes against what your boss might say you need to do.

But if the company culture is saying it's one thing and you point out that it's not that's good trouble You're gonna get in trouble for that and I am all about some good trouble I'm okay with like taking the heat for things that I say things that I do and it has absolutely come up in my career that I'm a troublemaker and So I decided to bring that it's like, okay, I'm good trouble

Rhona Pierce (02:19)
I love it and I love embracing the things that people tell you to try to like ⁓ silence you or minimize you and making that your brand. I love that.

Jessica Winder (02:34)
Yeah,

I that on. Like that is my persona now. It's like when it first, I'm not gonna lie though, when people first started calling me a troublemaker, they were like, are my feelings? Like I was like, I'm trying to do these things for employees or I'm trying to advocate for myself and you're saying that I'm a troublemaker. And then I decided to be like, okay, if that's what you think I am, I'll be it.

Rhona Pierce (02:53)
I'm still going to make trouble here. We're still going to get things done. I love that. was there a defining moment in your career that you first made you realize like your voice needs to be heard beyond what your job description says?

Jessica Winder (03:08)
Yes,

I would say ⁓ there are many times where I would be advocating for myself and I felt like people ⁓ just thought it was all good. Like they would see, you know, they would see me on LinkedIn and think like, she seems to have it all together. Meanwhile, I'm like crying in the parking lot or feeling like I'm being undervalued or I'm being underpaid. And so finally, the more I grew in my career, especially when I became a people leader, I thought

I should be advocating. should be talking about these things that have happened to me. So hopefully it doesn't happen to someone else. And so I decided to kind of like take a leap and be like, what if I start writing about this? And I will preface this by saying that by the time I was doing this, I was already a director. So I was already at a director level. I would not have felt comfortable doing some doing and saying some of the things that I say if I was not at that level. Because once I was there, it was kind of like, I'm not an individual contributor anymore. Now I will say there's nothing wrong.

with being an individual contributor and starting to write. You should absolutely do that. But I did not feel comfortable with the role that I was in and the company that I was in to do that.

Rhona Pierce (04:13)
I love that you call that out because it's so easy for a lot of creators in our space to say like, yeah, just say what you need to say, blah, blah, blah. But we know the reality is there's some privilege in being in management where you can say things that other people can't. And like you said, it doesn't mean that if you're an individual contributor, you can't create content. You absolutely 100 % should.

let's be real, there is a difference. work in HR, we know there is a difference with what some people can say versus others depending on their role in the organization. So thank you for for pointing that out.

Jessica Winder (04:52)
Yeah, and be mindful of it. Like I don't want anybody to, you know, don't, don't look at me and go get fired. Okay. I can't pay your bills. I can't do it. So don't do what I do because there are consequences.

Rhona Pierce (05:05)
I love that. I love that. And that's what we're all about here on the workfluencer. Like, yes, say, be out there, build your personal brand. But remember, you need to pay your bills.

Jessica Winder (05:18)
And I tell people this all the time because I see a lot of the stuff on LinkedIn where they're like quit your job be an entrepreneur and people ask me all the time like are you do you want to do you know your career coaching hit a gym, you know as your main job and my response is no, no, no, no, no, no, no, that's not for me. That's not what I've been called to do. This is what I like to do on the side, but this is not my full-time job. Like I want to continue to do my SVP of HR role and like do this as a passion.

Maybe one day down the road that will change, but that's not where I am right now. And so it has been a tricky situation for me at some jobs and I'm definitely open to going into it, but I definitely have had CEOs that were like, we don't like your content.

Rhona Pierce (06:01)
Let's talk about that. And I was going to get into that later. But since you brought it up, let's talk about that. Has there ever been a time where you've posted something and one of your bosses immediately called you and like, what WTF?

Jessica Winder (06:20)
Yes. Yes. I mean, it's happened several times. I actually had ⁓ and this is an interesting story because if I, I look back at it in a very different light than when I was in it. But I had a CEO one time that I had posted something and this was right around the time where I felt and I'm going to be honest, I'm just going to talk for myself. I felt like women's rights were under attack and I went to a protest because I don't believe in just speaking about it. I believe in being in the street, being an activist, all these things.

So I actually physically went to a protest ⁓ and I was interviewed at the process by the local news. Okay, I don't turn down an interview. Okay. So I said, okay, I'm willing to talk about this. And so I said, my personal views about women's rights and like women's bodies and all of these things, it ended up on the local news. also ended up on LinkedIn. People were screenshotting it and sending it to my CEO and being like, ain't this your HR person? Like, do you know that she's doing this? Now mind you, my CEO at the time,

also had his own personal brand and his personal brand was like pushing the envelope as well. So he was on board. But I point this out to say that if he wasn't, I definitely think that I probably would have been fired because somebody else would have felt very differently about me being so vocal about this. Mind you, I'm talking about my own rights as a woman. I talked about myself in my own right. And at the time I was living in the state of Texas, take from that what you will. Okay. And so that is what was happening. I was in Dallas. I was at a protest.

But I could absolutely see how I could have lost my job over that. So that's something that I say as a cautionary tale, be mindful of what type of organization do you work for? I knew at the time that my CEO would have my back for this. But I can tell you right now, if I had been at my previous organization to that one, that would not have gone over well.

Rhona Pierce (08:06)
So, so important to call that out. And I totally get what you mean by you were in Texas, I live in Oklahoma. So I get it. ⁓ I get exactly what you mean. I had two jobs here and then I realized I have to work remotely. ⁓ But yes, like we, you have to know where you work and you have to know how far you can push things. has your

content style and voice like evolved since you first started sharing online.

Jessica Winder (08:38)
absolutely. I started out very timid, very, I actually started my content just talking about what it was like to work in HR. I was not pushing the envelope in any way. I would just say, this is what my day to day is like, and this is what we're doing. In fact, one day I went and looked at my first post and it was about like a team lunch, like something about food, cause that's what I like. So it was very much not pushing the envelope in any way. And then I think the more comfortable I got, the more I started being like,

hey, just so you know, HR is looking at this or, hey, when you do interviews, don't do this and giving more advice. And now it has morphed into what is it like to work in HR, giving advice and also pushing other HR people on like, maybe we shouldn't be doing these things, or maybe we should treat people with respect, or maybe stop being the gatekeeper, you know, like pushing my peers in a way, honestly, pushing myself to to say things can be different. And why don't we try it?

Rhona Pierce (09:33)
That's really the point, I think, of putting yourself out there and creating a brand and everyone likes to say thought leader. Well, if you're not leading change, you're not a leader. You're just someone who writes content online.

Jessica Winder (09:51)
So you can't be a thought leader also if you haven't worked in HR in 10 years. You know, I'm gonna just say that.

Rhona Pierce (10:01)
Let's say that again.

Jessica Winder (10:04)
You cannot I'm sorry about it, but you cannot be an HR thought leader if you have not worked in HR in like 10 plus years I don't know what you're leaving. Okay. I don't know what initiative you're talking about. You haven't been in the mud You're not in the mud with us. Okay, I'm in the mud every day. I'm swimming around I'm trying to figure out what's going on. I'm you know, having the AI talks having the people leader talk, you know That's what's going on day to day. And if you haven't had to do that I Don't want your leadership ⁓

Rhona Pierce (10:33)
Hey, have you subscribed? Let's fix that. It's the easiest way to support this show Let's say someone's really thinking of making the leap to full-time creator And I know that this is not what you do but going back to what you're saying Ten years later, they're successful. They're doing everything. How do they stay in the mud? Yeah, now they're doing this full-time They don't have time to to go back and do a full-time HR job

How would you approach it if that were you someday?

Jessica Winder (11:03)
I think if that were me someday, one thing I would be honest about that, because a lot of times I feel like there's a lack of transparency with when you were last working in the field. So I wouldn't shy away from that. If 10 years from now I have not been doing this for 10 years, I will say, this is from 2025. This is what I was doing in that timeframe. I will not make it seem like I have still been actively doing these things, because that's not true. I also think there's some point of being a consultant, whether that's being fractional, doing something,

where you are still a part of it. Even if it's not your day to day, you're doing it once a quarter, you're still helping, even if you're volunteering. Because there is something about giving your time back as well. So maybe there's a nonprofit that could use your experience or an executive that could use your coaching. So still doing some of the work is what I would be doing.

Rhona Pierce (11:54)
Love that. Also, I'll add to it. I hope you have friends in the industry still. Talk to your friends. What are they going through? tell them like, Hey, I do it. I haven't been recruiting for two years now. And sometimes I call my friends and I'm like, Hey, I have some time. Let's jam. Let's let's source. Yeah.

Jessica Winder (12:14)
Why

not? Exactly. Why not?

Rhona Pierce (12:17)
Yeah.

So in your content journey, just switching gears a little, has there been a piece that you've created that felt like particularly vulnerable or risky for you to share?

Jessica Winder (12:30)
Yeah, so I talk openly about addiction and my own sobriety. And when I first told somebody that I was going to post in my original post was about my one year sobriety. And I said, I'm going to do a post about it. I'm going to talk about what I've been through. And immediately, and I actually respect, this was my own family. These are my own friends. They were trying to protect me and they said, absolutely not. Do not do this. This is, this is going to harm you. This is going to harm your career.

And I understand where they were coming from because there's something to be said about secrecy and like keeping things close to the chest. But for me, I knew that if I told everyone, if I put it out there and I told everyone, I would also be holding myself accountable. And I needed accountability in my journey. So I decided I'm going to tell everyone. I'm going to tell everybody that I am sober. I want to remain sober. And one way to do this is to talk about it and to also help other people. Because I know for a fact that

Anytime I do a sobriety post, I get so many DMs, literally hundreds of messages from people that don't feel like they can talk about it publicly, but want someone to know that one, they are struggling or two, that they just got sober and they want to talk to somebody about it. So those posts are my most vulnerable. They are also like my most popular posts talking about that. I am now five years sober.

This is something that is very important to me. It is something that has absolutely changed my life and my journey and the trajectory of my life. But it was vulnerable to make those posts to say I have struggled. I have struggled with addiction and now I am sober.

Rhona Pierce (14:02)
love that you share that. And I love that you get such great response because I cannot relate to that. ⁓ 100 % I'll be honest, but for like health reasons, I've recently stopped drinking. I realize how especially at HR conferences, by the way, I'm going to call this out. You go to an event and you say like, Hey, can I have a mocktail? And it's like, ⁓ my gosh. And it's like,

a mocktail and it's like, guys, literally serve the same thing without the alcohol. Like you can do it. This isn't a big ask that I'm doing. But now I imagine if this were someone who was struggling with addiction, dealing with it, why are they like now everyone at the bar knows that I want a mocktail as if I asked for I don't know what that that doesn't exist. So I love that you talk about it and that people can have someone that they can talk to and relate to because

I was at a recent conference in Vegas and I was thinking, imagine if I were in recovery, how this would feel, how I just got treated by this person at this event.

Jessica Winder (15:12)
No, that has absolutely happened to me. And one of the things that I've actually started to do, so I want to say this to any listener that is going through something or wants to start drinking. One of the things when you fill out your conference, like attendance and like they ask you for any accommodations. One of the things that I have personally started doing is saying, I need an accommodation. I need mocktails to be served. I want there to be non-alcoholic options. And it has actually worked out for me where I've actually had someone contact me from that being like.

We saw what you said, we are going to have like non-academic here, we're going to have these options for you. So I now treat it as an accommodation. I want an accommodation. Okay.

Rhona Pierce (15:48)
I love that and I'm absolutely going to join you in doing that as well. Yeah, I love that. So now let's go back to talking a little about content and I'm so excited to ask you about this. So you recently started posting on TikTok and YouTube after being resistant to video. Like what finally got you to hit record?

Jessica Winder (15:55)
It makes a difference.

my goodness. For years, and I mean years, people have been saying, why don't you record videos? And I literally would be like, I don't want anything to do with TikTok. Like that's for the young kids. And I'm not going to say how old I am, but I will say that I have a 21 year old niece who very much is into TikTok. And when I decided I was going to do TikTok, I had to call her and be like, can you walk me through this? Can you give me a tutorial? ⁓ So I say that to say, I felt like I was resistant and maybe it was like a generational thing. Like I'm an older millennial.

And so in my head, this was like a Gen Z, like this doesn't have anything to do with me. I don't want to do a dance video. ⁓ But at the same time, I was on TikTok, but just as a lurker, like I was just on there observing other people's content. And there's so many great people on there that are giving out great advice about the workplace. But I will say what motivated me was the people that are getting fake advice, people that are out there like actually doing harm, giving out advice that have never worked in HR.

that have never been in a leadership position, that are giving advice about how to interview or how to get around this or how to game the system that I felt is harmful. So that is actually what motivated me to be like, you know what? I've been doing HR for years. I need to start making videos.

Rhona Pierce (17:25)
Yes, and we need more voices of people who actually know what they're talking about. Because the confidence out there is astounding. That's the nice way I can say it. So what surprised you the most about like putting yourself out there on video versus other formats that you've done?

Jessica Winder (17:39)
So nice.

I think for me, it's really interesting because I love to write. So writing for me comes very natural. Like I can write a post, people laugh. I can write posts all day long because I'm consuming content all day long. So something will spark my mind. I'll write a post about it. Like it's, I have hundreds of posts in a Google doc that are just ready to be posted because it's just something that I see. I can't tell you my first video. I don't know how many other times I recorded it. Okay. Like I don't know how to edit. So it's either it's right or I have to do it all over again. So that's something I need to work on is editing.

⁓ but I think what gets me is how long it takes me to get it done versus I could write something quickly and post it and be done. So I think the process I'm still, I'm still quite frankly, trying to understand how to do it and be efficient. I don't know. Like I'm still recording content and being like, is this good enough or is this not, but I'm kind of going with it. Cause I think you have to go through this, the stumbles to get to something that's like a great product, quote unquote, if that's how you want to go about it. I also think there's some vulnerability and being like,

I have almost 80,000 followers on LinkedIn and I have like maybe 100 people on TikTok. You know what I mean? And that's okay. Like I'm learning, I'm figuring it out as I go.

Rhona Pierce (18:59)
Why haven't you brought any of your videos or have you to LinkedIn since LinkedIn is pushing video now?

Jessica Winder (19:06)
It is and so I have like I recently all the stuff that is on my TikTok I have now brought over to LinkedIn which I actually found to be a little scary because the stuff I've said on TikTok I was like this is nothing compared to what they say on here and then I put the videos on LinkedIn and I was kind of like I don't know. So I definitely want to cross cross-pollinate you know I was talking to I'm friends with somebody who does

primarily took talk and wants to get into LinkedIn. So we were collaborating because I'm like, I know LinkedIn, I could teach you all the tricks and all the things to do. So I'm trying to learn and also be open to getting feedback from other people.

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How did the videos work on LinkedIn? And I know it's a difference in the audience size and everything, but like, how did your audience take to your TikTok videos?

Jessica Winder (20:37)
They really liked it, which is so funny because I got way more comments on the video than I normally get on my written post, which is really ⁓ interesting. ⁓ And to your point, LinkedIn is leaning more towards video. So I definitely think it's something that I want to continue to do and continue to grow. I don't see myself like kind of tailoring like to TikTok and LinkedIn. I think it's, I'm recording one video and it's going on both.

Rhona Pierce (21:04)
Yeah, and that works for a lot of people and honestly, a lot of people do it. I think there's very few times where I'm like, okay, this is definitely not a LinkedIn thing. in the type of content that we do in our space, I think there's a lot of opportunity to like just cross post.

Jessica Winder (21:25)
Yeah, absolutely. I will absolutely be doing that because to be quite frank, I just don't have the patience.

Rhona Pierce (21:32)
Now let's talk a little about like the actual process of you juggling a nine to five. And I know you have two sets of toy. He's like, they're under three, right?

Jessica Winder (21:40)
I do. Baby. Yeah,

I have four kids under the age of two.

Rhona Pierce (21:47)
wow. And you create content. So can you walk us through like what a typical content creation day looks like for you?

Jessica Winder (21:56)
Yeah. So it honestly, it varies so much and it varies because to be quite frank, I'm still trying to figure it out. So most days I'm always writing. So on a typical day, I will absolutely be writing two to, I say two to five posts or ideas of posts that I'm going to be posting on LinkedIn. So that's happening every day. and then on days where I'm going to record content, I've yet to record content where I wasn't like made up and you know, like my hair is done and stuff, but I'm going to get there.

Okay, I'm going to get to the point where I'm just doing it in a top knot. But for now, it's a whole production with the lights and I, you know, I bought all the gadgets from Amazon that I need. And normally I try to batch it because to your point, I have four kids, so I don't have time to be recording content every day. So I normally absolutely will record, you know, five to seven videos in one day, just like come up with the topics. And I pull my topics from things that have done well on LinkedIn.

So if it's done well on LinkedIn, I then say, okay, this is a topic I can use and create a video about it. And sometimes ⁓ I tried actually, I tried to script, I tried to do like a teleprompter, couldn't do it. Hated it, didn't like the way that I was looking, like it felt very like force. Honestly, I would get lost on the teleprompter, I just couldn't do it. So I have now decided that when I do my videos, I just start with a topic and I just talk. So I just straight talk to the camera.

give advice, talk like I'm talking to a friend and that goes over better for me. ⁓ I have seen other people do some scripted content that I actually am really interested in doing. I just have not been able to do it yet. So I definitely batch content, like as much as I can, I put it all together and then go back and post it at different times. Even to the point of like going to change outfits, like recording like four videos in one outfit and then go upstairs, change and come back down. Yeah, I definitely done it.

Rhona Pierce (23:44)
I love the evolution that you'll see and you'll see this and I hope when you get there you'll remember me. ⁓ Before I used to have like the different outfits so like that door that you probably can't see in the frame is my closet for my video clothing and it used to have a ton of things. Now if you open it, there's a ton of tops just like this one. Literally, I only wear black and like release yourself from thinking. love it.

that you need to change that way. Like the less barriers you have to going and creating the content, the less you can make excuses. And I'm going to plug this, which I really hope they sponsor me one day, but the DJI pocket Osmo DJI Osmo pocket three camera, which I wish I had mine right here. I probably do. ⁓ I've recently discovered that in their app, you can record and it

puts makeup on you. And I discovered it because I accidentally forgot to do my makeup and did a full like batch like 10 videos. And I was like, my gosh, I look like I'm dead. My lips were like, the Osmo pocket. I saw this thing that says like beautify. I'm like, Ooh, what's this? And it did lipstick. It did my I like

and it looked just like me. Like those videos are out there and no one's like, my gosh, you went and got, cause I never like glam up. So yes, there's things out there where you'll get so comfortable and you'll, I was like this game over. If I don't have to do a full face of makeup, it's odd. There's no excuse to ever not create a video from now on.

Jessica Winder (25:31)
100 % and to your point about the barriers for me, it's just a time management thing. Cause to your point right now, if I'm not like with my kiddos, I'm like working and I work for a Canadian company. So the time difference works in my favor, but to the point, like I still have to find time to record. And normally that's like in the afternoons or when my kids on the weekend are asleep. So if they take a two hour nap, sometimes I like run into my office and be like, okay, I'm going to record some content right now. Um, but also I'm tired a lot. Like I will be honest with you.

Like I'm a working parent, like I'm tired. Like so there are some videos where I'm just like, listen, this is all I got to say bye. ⁓

Rhona Pierce (26:08)
As long as the content's good, people will watch it. ⁓ TikTok, people will have comments on how you look no matter what. that's just TikTok. LinkedIn, think people are nicer.

Jessica Winder (26:22)
Yeah, I agree. haven't had any like none of the videos got any of those type of comments that they got on TikTok.

Rhona Pierce (26:30)
Let's not even talk about TikTok for now. So how has showing up publicly shaped the way that you lead internally?

Jessica Winder (26:41)
That's a great, great question. ⁓ It's interesting because I know that my team listens to like the podcast and they read my posts and all that stuff. And I actually had someone on my team tell me one time that she was listening to a podcast and she was trying to decipher it. I was talking about the team and I wasn't, but she, so it's something that I am very mindful of because I definitely want my team to feel like they can talk to me about anything that they trust me. So none of the things that I'm going to talk about public right now are about my team.

So I talk about things that have happened before or like past organizations. So that's something that you have to keep in mind that like when I'm talking about my current company, it's only talking about like these are the roles that we're hiring for, or this is why you would want to join the team. I do not talk about wherever I currently work at that time. Like once I leave, it's a different story. ⁓ Past organizations, know, it's a different thing, but it's something to be mindful of because

my peers are reading my content. And so that has come up before where someone thought I was talking about them. ⁓ There's been a timing of a situation that I posted something and the timing of when it was going to happen to somebody at this organization. just happened to be that way. Cause I also ⁓ do the posts like the draft post. So there's posts that are going to go up three months from now that are already set.

So I had no clue that the timing of this was going to align. And it did cause some issues for me because this person thought I was talking about them. And it was just such a, like a horrible coincidence that this post that I had written three months prior and it was the same situation. So be mindful of that. ⁓ Be mindful of what's going on in your organization and stay away from that when you're posting publicly, because you don't want employees. I don't want employees to feel like I'm talking about them because I'm not. So.

It is something you have to be very, very mindful of.

Rhona Pierce (28:31)
Do you feel comfortable sharing how you handle that specific situation just for anyone who might find themselves in that situation?

Jessica Winder (28:40)
was just super transparent. And I told them that like, hey, like, I actually pulled up my LinkedIn and showed them how far out my posts were. And I was like, this is how far out I am posting. So this post was written three months prior. And I showed them the document because I wanted them to be I wanted it to be clear that like, this is how far out I'm going. And they were like, okay, get it because I didn't want to lose this person's trust. And so I felt the need to really just show them what's going on in the background. And they don't

post on LinkedIn. So they had no real insight that you could even do the timing and do the schedule. So even to just show them that this is how I do this, they were like, okay, I get it.

Rhona Pierce (29:19)
I love that ⁓ transparency always wins. ⁓ And it's so good that as an executive, you are mindful of that. Because yes, when you are leading inside organizations, we want people to trust us, especially when we work in HR. We want our team, we want our peers, we want everyone in the organization to trust us. We have enough of a perception problem, we don't need to bring it upon us. So that's really good advice to not talk about your current situations with your current employer.

Jessica Winder (29:48)
No, but my pro tip is start writing, okay? Definitely keep you a little notepad of things that, you know, our future content, but don't post it.

Rhona Pierce (30:01)
Do you encourage your team or your peers to create content of their own?

Jessica Winder (30:06)
Absolutely. So I've actually, my current team, once a month we do like a lunch and learn where we each go around and teach somebody or teach the whole team something. And it can be professional, it can be personal, all that stuff. The very first one I did with my current team was about personal branding and teaching them how to do LinkedIn. And a shout out to Tessa, who is my recruiter, and Kristen, they both took that on and have brand with it and are posting content all the time. So absolutely, I encourage.

I've definitely been pushing my peers that they are a little bit more resistant to posting, but absolutely, I think it's important, especially from our recruitment team.

Rhona Pierce (30:40)
I love that. And a lot of companies are embarking on this employee advocacy and workfluencers, might I say, ⁓ because they're seeing the value of having their team out there, their personal brands and just all the, we can talk, that's a whole other episode of all the benefits of that. ⁓ But what's been your experience like balancing company guidelines with authentic personal expression where

when it comes to like, okay, now you're encouraging your team to create content, they might get in trouble if they post something that crosses the line. So how do you balance that?

Jessica Winder (31:20)
Yeah, I will say the thing about my current employer and the last three employers, it's all been startup. So it's different in a startup. So where I'm at right now, it's very much a everybody posts, do whatever you need to do, like, you know, keep it respectful. But I have been in a previous organization where they had very strict, the marketing team would send out like guidance, they would send out like, hey, we're gonna they would say, hey, we're gonna launch this product. Here are three things that you know, we would like for you to post. I personally

very, very resistant to it. And whenever they would ask me to do it, I'd be like, I will post, but I'm going to post in my own voice. Like I'm not taking your copy. I'll take your suggestions, but I will not take your copy. I'm going to make it my own. ⁓ that didn't go well. I don't work there anymore. So, you know, but there are companies that would prefer you to post it word for word, what they want you to post. And I personally don't want to do that, but I know other people that do, and that's fine. So it's, it's, think it's a personal decision if you want to post that. However,

Statistics show that that doesn't do as well when every single person from the company posts the same content. You know, like it's not personal in any way, so it does not go well.

Rhona Pierce (32:29)
posted about that probably sometime last year and I don't remember the exact thing that I said but the basically it was like we can tell I was saying like it's like it feels it's giving hostage situation yeah and it was it was one of my top posts and it was funny because I just like wrote it because that day I had seen a company a large company I had worked at before and they literally everyone had posted the same thing and it's like I know these people when this is not how you talk and what

coincidence that everyone has the same post with different pictures because they got to choose their pictures. And it was funny that the people that had been posting that, that inspired my post were some of the ones that were liking and loving my content the most. It's giving hostage situation. This is not helping. We all can see right through it. Why are you even wasting time? And they have a full blown

employee advocacy program. I'm like, no.

Jessica Winder (33:30)
No, no, no. And you can just see right through it. It sounds robotic. It sounds like AI. And so it's no, it just never goes over well. And to your point, it does. It's giving read off of this paper, hostage situation.

Rhona Pierce (33:47)
So have you ever got some feedback or response to your content that fundamentally changed how you approach creating?

Jessica Winder (33:59)
Yes, in a positive way. I've had so many people reach out to me and say ⁓ that they either wanted to like my content or wanted to comment on my content and they did not feel like they could, which makes me sad. Actually makes me very sad that you couldn't even like something because your manager might see it or somebody you're coming might see it and feel some type of way. So every time somebody messages me one of those messages, I think I'm going to keep speaking up. I'm going to keep doing this because

There are so many people out there that cannot speak up for fear of losing their job, for fear of retaliation. And I'm not in that situation. I can say whatever I want. And so I'm going to continue to do it.

Rhona Pierce (34:39)
Have you ever gotten suggestions from people and the DMs was like, hey, have you ever thought about posting about this?

Jessica Winder (34:47)
All the time, all the time. Daily somebody sends me like, this is what's happening with me at my job or can you believe this? And I actually have like with their permission, I'll be like, listen, you will have no association with this. I'll make it clear. But I have absolutely when people give me permission, then like, this is a story to tell.

Rhona Pierce (35:07)
love it. Some of the best content that I've posted has come from someone in the DMs like, look, I can't say this, but I really, really want to say this. Is there like, what should I do? I'm like, with your permission, I will tell this story.

Jessica Winder (35:24)
I will absolutely tell the story on your behalf. I've done that a lot, but yes, I get DMs all the time from people that are going through, especially because one of my ⁓ posts that went viral was about like a workplace bullies. And so that has struck a chord with people that I get a lot of DMs about bullies.

Rhona Pierce (35:43)
So good. ⁓ It is a thing and it's a thing that no one talks about. ⁓ What's the, like for professionals listening who are actually scared to post because of their nine to five, what advice would you give them?

Jessica Winder (36:00)
I would say lean towards what brings you joy. So you do not have to be controversial. You don't have to be spicy. My voice is very like assertive in your face. But like I said, I didn't start out that way. I started by just saying, this is what it's like to work in HR. So you could do a, is what it's like to be a marketer. This is what it's like to be in sales. Like you could literally just start there and

morph into whatever you want it to be, but you can decide what you want your tone to be. This is something that when I do personal branding workshops, I tell people you decide when someone sees your photo or sees your name, what do you want them to feel? You can decide that. You can want them to feel joy. You can want them to feel whatever. When somebody sees my name, sees my photo, I want them to feel like fiery. Like, I don't know what you're gonna say, but it's gonna be fire. That's how I people to feel.

Rhona Pierce (36:50)
That's such great advice. And it's true. Yes, it's really you controlling the narrative. it sounds like a little bad, but it's like, no, no, no, this is what I want to be known for. This is what I want people to feel. And whether I say something or not, because it's 2025 and the internet exists, people are going to make their own opinion. So let me be the one to shape what they should be thinking.

Jessica Winder (37:17)
Absolutely. You own the narrative. So you can make it whatever you want to be. And also, I just want to say you can also change it. You can start in one place and end up somewhere totally different. So it is OK to start in like a soft era if that's what's best for you right now. And then you can get over here to good trouble if that's where you want to go.

Rhona Pierce (37:35)
Yes, yes. like, so good that you said that because so many people stay stuck on it's like, no, I can't, you absolutely can change. And you can change your topics, you can change your tone, you can change your formats. Really, it's all about evolving. And most people don't even remember what you posted. And I always tell, I've been recently saying the story, a few months back, I was just like,

Creative burnout at the beginning of this year and I could not create like I sat there I couldn't create a new podcast episode a new video a new post it just wouldn't flow So what I did was because I do this for a living so I still need to you know The bank isn't like sorry, you're not being creative today. ⁓ I Still need to pay bills ⁓ I post it I reposted things from last year or from the year before and

Some of the people and like looking back, because I have access to look back, some of the people who are like, my gosh, this is so good. Hadn't thought about this this way. Had said the same thing last year. No one remembers your post. You're the one that remembers them. No one remembers them.

Jessica Winder (38:47)
Anything I always tell people, anything six months and older, just repost it. You don't have to change a single word. You don't have to do anything. Or what you could do, and I've done this with my content, is anything six months or older, maybe somebody said something in the comment that sparked an idea or something like that, you can rework it. But absolutely repost content.

Rhona Pierce (39:06)
Yes, and I will add a link to this and full transparency and affiliate link to this in the show notes. But I use a tool called Creator HQ by Jay Klaus. ⁓ a notion operating system. And what I love is that you put your post in there as you plan them and it has a repurposing calendar and it tells you in six months you can go to that calendar and it does it for like three, six and 12 months and you can look, it's like, ooh,

I posted this, let me go look at it back and to your point, I look at the comments and then you can reshare it either as is or add a little more because from the comments, from the conversations, you learn more and you can add to it. So I'll add that to the show notes, but it's an amazing, amazing tool.

Jessica Winder (39:53)
Yeah, I need to get that. ⁓

Rhona Pierce (39:57)
have an affiliate link that I will share with you. So we've come to my absolute favorite part of the show. It's my favorite segment and I hope it's everyone's favorite segment soon. It's called Plead the Fifth. So I will ask you three questions. You can plead the fifth once, but only once. And you're not gonna know the questions ahead of time. You'll know as you go. So use it wisely.

Jessica Winder (40:26)
Okay.

Rhona Pierce (40:27)
All right, first question. What's the biggest lie on your own resume or LinkedIn profile?

Jessica Winder (40:40)
Ooh.

something about being a team player.

Yeah, probably something about I'm a good team player. I'm not. Okay. I like to do things by myself and everybody else can take the credit, but I'd rather do it by myself.

Rhona Pierce (40:59)
Right. Next question. Have you ever shared job search advice that you knew wasn't universally true but would go viral anyway?

Jessica Winder (41:14)
Yes, in that I have told people that, you know, cover letters are fan fiction and they're trash, but I've written them for people. So if you pay me, I'll write it for you and I'll talk about it.

Rhona Pierce (41:25)
I this. love this. Okay, last question. If you could cancel one creator and get away with it, who would it be?

Jessica Winder (41:34)
Mm-mm, plea the fifth, okay, great job. Uh-uh, honey, not today.

Rhona Pierce (41:42)
All right. All right. ⁓ I should have added that one first. I was like, need to change the order of these. So I've really enjoyed this conversation. Is there anything about what we've talked about or in general that you think listeners need to know that I haven't asked you?

Jessica Winder (42:02)
The only other thing I would say is that you can start writing and then wait until you're ready to post. So I know a lot of people that feel like they have to write and immediately post, and that's not true. You can just get it off of your chest, get your experience out there. To me, writing is almost therapeutic, especially when I was in situations where I felt undervalued or that I couldn't speak up freely. I would write about those experiences. And even if I wasn't posting them,

That's a place to start. So even if you just simply open a Google Doc and start writing down your experience that when you are ready, wherever, whenever that is, whether that's months or a year from now, you will have content. So that's what I would say. Start there. Just start writing.

Rhona Pierce (42:42)
Love it. How can listeners connect with you?

Jessica Winder (42:45)
On LinkedIn, daily, I love LinkedIn. It's my go-to social media platform, which my niece finds to be her, like she's like, LinkedIn, really? I'm like, yes, love LinkedIn. Okay, Jessica D. Winder. And then I actually just started a newsletter called The Corporate Cheat Code. So that's gonna be coming out weekly. So those are the two places that I would say, also I'm on TikTok obviously, but bear with me with my videos, okay?

Rhona Pierce (43:11)
your newsletter. I want to hear more about it.

Jessica Winder (43:14)
Yeah, so I started actually literally just posted my first one today. It's something that I've been thinking about for a while that I have a newsletter on LinkedIn, but I wanted to convert it to a different platform and kind of be able to talk a little bit more freely. So I started it. It's called the corporate cheat code, giving insight into like how to interview, how to get a promotion, all the things that I have personally been through or coached people through and how to do it. So think of it as your cheat code.

your secret HR in your pocket on teaching you how to get around the

Rhona Pierce (43:46)
Perfect. Amazing. I've loved this conversation. Thank you so much for joining us on the pod today.

Jessica Winder (43:51)
Absolutely, this was so wonderful.

Rhona Pierce (43:53)
Thanks so much for listening. If you're enjoying the Workfluencer pod, share it with someone who's changing how we talk about work or who should be. And hey, if this episode gave you ideas or inspiration, leave us a five-star review. Reviews help other listeners find us. And honestly, it makes my day. Workfluencer is produced by Perceptible Studios. Learn more about how we can help you use video to attract, engage, and retain qualified talent at perceptiblestudios.com. Thanks for listening and I'll chat with you next week.