The House Always Wins: Why Ignoring Workplace Red Flags Will Cost You feat. Danielle Roberts

You wouldn’t sit at a blackjack table, ignore the odds, and hope for the best—so why do leaders do that with their teams? Employee disengagement, customer churn, and burnout don’t happen overnight. The signs are there… if you’re paying attention.

In this episode, Alyssa Nolte and Danielle Roberts break down why companies gamble with their people, customers, and bottom line—and always lose. We’ll cover:

• The "silent quitting" problem—when employees mentally check out before they actually leave
• Why leaders ignore red flags and how to train yourself to see them before they escalate
• How unspoken resentment leads to costly turnover and brand damage
• Lessons from companies that waited too long and the ones that course-corrected in time
• Simple strategies for getting ahead of problems instead of playing a losing hand

If you're leading a team, running a business, or just tired of watching the same mistakes play out over and over, this episode is your cheat code. Stop rolling the dice with your company’s future—tune in now.

Key Takeaways:

• Problems don’t appear overnight – Employee disengagement and churn have warning signs; leaders just need to pay attention. 
• Ignoring red flags is costly – Avoiding tough conversations leads to turnover, brand damage, and lost revenue. 
• Proactive beats reactive – The best leaders spot issues early and take action before they spiral.

Key Moments:

00:00 Introduction and Welcome
00:15 Danielle's Origin Story
01:39 The Turning Point: Personal Loss and Career Shift
02:42 Founding Anti Career Coaching
04:19 Challenges in Modern Leadership
05:40 Empowering Self-Leadership
07:26 Building Trust and Belonging in the Workplace
18:25 The Importance of Culture Change
23:11 Inspiring Leaders and Final Thoughts
25:55 Conclusion and Farewell

It's time to say "goodbye" to the Sunday Scaries.

Connect with Alyssa
LinkedIn: https://www.linkedin.com/in/alyssanolte/
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Follow the show on YouTube: https://www.youtube.com/@TakingBackMondayPod
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Transcript

alyssa-nolte_1_02-19-2025_111526: 0:00

Hey everyone, welcome back to Taking Back Monday. I am so excited that you decided to say goodbye to the Sunday Scaries and hello to a new future of work. And I'm even more excited to introduce you to my new friend, Danielle. Danielle, welcome to the show.

danielle-roberts--she-her-_1_02-19-2025_121526: 0:13

Thank you so much for having me. I'm excited to be here.

alyssa-nolte_1_02-19-2025_111526: 0:15

So tell me a little bit, one of the questions I like to ask is, is your origin story. How did you become interested in this idea of, you know, taking back Monday?

danielle-roberts--she-her-_1_02-19-2025_121526: 0:26

Yeah, that's a great question and it's been a long journey to get here. Um, like many millennials, I checked all of the boxes and did the right things of what society told me to do to find success and happiness. I put myself through college. I had a job lined up right after college and I hustled hard to climb a corporate ladder, um, just to kind of reach one of the higher rungs and look around at my life and say, what? That's it. Um, I didn't know myself at all. My career was my entire identity and I didn't know what to do about it. I, I started my career in advertising agency, which is very well known for fast paced, high pressure environments for absolutely no reason whatsoever. It wasn't urgent work at all,

alyssa-nolte_1_02-19-2025_111526: 1:16

You mean ad agencies aren't saving lives and

danielle-roberts--she-her-_1_02-19-2025_121526: 1:19

No.

alyssa-nolte_1_02-19-2025_111526: 1:20

They're just imaginary fires.

danielle-roberts--she-her-_1_02-19-2025_121526: 1:22

Yeah, like, all right, my client, who is a casino, like, God forbid we don't get this email out. Like, what is going to happen? No one's, no one's going to die. So like, is it really a deadline? Um, but we were still there pulling 60, 70 hour weeks and I loved it at that point. I was like 23. And then my mom got sick. She, uh, Got diagnosed with cancer and within nine weeks she passed away and I was making 28, 000 a year. I could not afford to take FMLA and I was one of my mom's primary caregivers and I had to be back at my desk after three days of bereavement leave. And I remember that moment and this is a long time. This is almost 12 years ago now. So I remember like being back at my desk and saying like, Man, this feels weird, but I don't know what else to do about it. So I just threw myself into working harder because that felt like the one thing that I could control. Um, and I changed jobs to something that had a little bit more stability in higher education. There were issues there. I changed jobs again into tech. There were still issues there. I moved to try and like do something for myself. And one month after I moved, I got laid off from my tech job. So I was like a thousand miles away from my friends and family. No paycheck, no support system. And I was like, I need, I just can't keep doing this. I'm too burnt out to function. So I started to ask myself questions about like what work meant to me, what it was supposed to be for. And I started my business from there. Started career coaching, using my background and career development to help position candidates and that slowly evolved into what is now anti career coaching, which is essentially You are not your job. Your job is supposed to help you invest in What else makes life meaningful for you? Um, so now I do a lot of future of work thought leadership speaking consulting writing and it's really purpose driven work It's taken me a long time to get here, but i'm I wouldn't do anything else

alyssa-nolte_1_02-19-2025_111526: 3:18

I'd love to say that, you know, in the ideal world, your story is the anomaly. It's, it's the thing that doesn't really happen very often. You're the exception. But unfortunately, I think everything you said is kind of the rule these days. Like when you talked about, you know, your mom got sick and then she passed away within, do you say nine weeks?

danielle-roberts--she-her-_1_02-19-2025_121526: 3:36

Yeah Yep,

alyssa-nolte_1_02-19-2025_111526: 3:38

leave and then back at your desk. Like that's unfortunately a fairly common experience. And actually you said something kind of. That I never thought of, like, deadline, like, nobody's gonna die, that's why it's called a deadline, like, oh my gosh, that's a hundred percent why it's called deadline. Um, but, like, I kind of believe that it doesn't, I believe wholly, wholeheartedly, it doesn't have to be this way, right? And my whole experience, like, you know, you talk about, you talk about the future of work, my whole belief is that leaders are the ones who have the power to, to change this and maybe even the mandate to do so. You know, when you're coaching through your anti career coach, which I love that, um, how are you setting your coaches up for success in, in a world of work that hasn't caught up to that approach yet?

danielle-roberts--she-her-_1_02-19-2025_121526: 4:33

Yeah, so I think the answer is twofold. We have leaders who have never been trained on how to become effective leaders. There's a Gallup article that says fewer than one in five of those currently in management positions display a high level of leadership. of ability to lead others. So like not even one full ass human being is a good leader that's in a management role. That's a problem because our leaders are what create a sense of psychological safety for us to open up and be vulnerable and thrive in whatever position that we're in. So I think that our leaders have a responsibility to become more emotionally intelligent. Um, But I also think we can't wait for that to occur because our organizations are kind of microcosms of the larger capitalist system that we live within, which is growth and productivity at all costs, including the human ones. So when I work with my clients, I teach them how to become more self sufficient. And increase what I like to refer to as their entrepreneurial power. So leading from any position regardless of the title that they hold. That includes a lot of self advocacy skills, which includes like, Values identification, understanding what our natural strengths are and where we thrive, learning how to communicate effectively, to say what we want and need, handle conflict resolution in the workplace, so we can become more visible and advocate for ourselves without waiting for leaders to give us permission or drop opportunity into our lap. Mm

alyssa-nolte_1_02-19-2025_111526: 6:07

So it sounds like to me, That you're really just training the future leaders of these companies, because every skill that you're talking about is what makes for great leadership of the bill, the ability to self advocate the number of times, like I'm also a millennial, the number of times that I just kind of smiled and nodded because it was easier to just say yes and get past it, then actually advocate for myself. Like that's not a very good leadership trait. And so I had to learn. How to stand up for myself almost and not be such a pushover because as a leader, I need to be decisive and make choices and, and the ability to tell your own story and talk about your own successes in your own wins. Like those are leadership skills and you talked about, you know, one in five or whatever that number was that hasn't that are in a leadership role without any kind of formal training. What a great way to let people lead themselves. And I had a guest on the podcast who. It was like one of my very first guests. It was like a lifetime ago. Um, who said something like you need to earn the right to lead. And in order to do that, you have to lead yourself first before you're allowed to lead anyone else. Have you, have you seen like success with your clients? Are they, are they moving up the career ladder faster? Are they moving in a direction that's more sustainable? Like, what is that? What does that look like for them?

danielle-roberts--she-her-_1_02-19-2025_121526: 7:26

Yeah, so I think that the biggest quality too of leadership is trust, right? The ability that you are going to do what you say you're going to do, um, and that, you know, your leaders are going to do the same. Um, when my clients go through my process, usually the path that they think that they are on is not the one they wind up pursuing.

alyssa-nolte_1_02-19-2025_111526: 7:48

Right? How often is it like you're like, I'm going to this destination and you discover that's not at all what's about to happen.

danielle-roberts--she-her-_1_02-19-2025_121526: 7:54

Yeah, because once you start to become more self led and ask yourself some of the internal questions of what you actually want, not what society convinces you that you want or how you're supposed to act, um, this veil is kind of lifted. Of like, oh, okay, I've just, maybe I've been climbing this ladder because that is what I was supposed to do, and that is the next logical step, but it's not something that I actually want. But now that I'm giving myself a little bit of permission to do what I want. I've always been curious about what it's been like to do X. Um, so in some cases, They do climb the corporate ladder and they're able to advocate for more money or more flexibility in the roles that they're currently in. In other instances, it's, oh, like, I've actually thought about starting my own business and I just never knew how to do that. Or it could be, oh, I'm a stay at home mom and that is the only job that I've had for the past ten years and I want to go back to work and feel more powerful in a professional position. And they give themselves permission to want that. So there's no one size fits all answer. And I think that's the beauty of what I do. Like, becoming self led or having an anti career mindset is basically, you're allowed to change your mind. You're allowed to pivot because your career evolves over decades. And what you want now should look different than what you wanted 10 years ago and will look different than what you want 10 years from now. So like, permission to change your mind.

alyssa-nolte_1_02-19-2025_111526: 9:25

I mean, it can't be that simple, right? There's got to be so much more to that because I'm thinking about some of my friends who have done the traditional career path and I never have. I've always been very entrepreneurial. So for me, like, it's always been fun what I'm doing. And money was the, um, the side effect of my, of my joy, but. You know, I look at some of my friends who are on very traditional corporate paths and they would never consider doing what I'm doing, even if they would want to. Because it's scary. Like, the idea of abandoning who you were and your identity for the last ten years. Because you go to a party and people don't ask you questions. The first question is, so what do you do?

danielle-roberts--she-her-_1_02-19-2025_121526: 10:06

Mm hmm.

alyssa-nolte_1_02-19-2025_111526: 10:07

And we've wrapped our souls around these careers that we've created so much so that it's the first thing we tell people when we meet them. I'm an accountant. I'm a sales rep. I work at an ad agency. Instead of, I love kayaking, and I love dogs, and I spend my weekends playing, you know, video games.

danielle-roberts--she-her-_1_02-19-2025_121526: 10:24

Mm hmm. Yeah. And I think that's a Western problem. Right? Like, our society is hyper individualistic, and our entire sense of belonging is wrapped up in Our career, because our career means like how successful we are, how busy we are, how valuable we are in terms of money and productivity, but like that is, our career is not our sense of self worth and you can be an entrepreneur and that's scary, but state of the world now, where's job security going? Like, there's, there's no of those assurances anymore in our modern workforce. But what you can do is create those solid foundations within yourself. Understand what your personal brand is, the impact that you want to make in this world, and how you can express that through a variety of different career paths. So God forbid, if you do get laid off, you do get fired, a company does go under, you have options, and you still know who you are. Because that's exactly what happened to me. I was like, yeah, I am, I've spent. Was 10 years in corporate social media marketing before doing what I did now. And I was like in a state of freeze, not knowing who I was. It took me like a solid six months to just get that momentum back of like, well, what do I want to do? Um, I didn't have hobbies outside of work. My career was very much my identity. So I think it's understanding the impact that you want to make professionally. But like you said, making yourself well rounded outside of work, like what does your paycheck help you invest in? What is the quality of your relationships? Do you have a relationship with leisure? What is your wellness routine? How do you treat yourself like that whole last human being outside of work? So you can become self led. You can lead yourself and others and embody the qualities that a leader would have.

alyssa-nolte_1_02-19-2025_111526: 12:17

don't, Oh no. Like, you know, like for me, my business has always been my hobby and that's, that's because I love it. And it truly brings me joy. Um, but there's a lot of people who just feel like they get home from work at, you know, five, six, seven, whatever time they finally make it home. And there's just no more energy left for anything else. Or they're like, I might as well not start anything. Cause I won't get to actually enjoy it or finish it. So a lot of our listeners are our leaders. They either lead small teams or they, you know, lead whole organizations. Let's say, you know, they want to create an environment or help their team build this healthy relationship with work because they are like us and they believe that the future of work is human centered. What should they be doing? What should they be keeping in mind? And what risks or red flags should they be looking out for that they're maybe missing the mark?

danielle-roberts--she-her-_1_02-19-2025_121526: 13:10

Yeah, that's a great question. So first I'll start with the red flags. So. Like worker disengagement is at an all time high. So when people like, when your team members are disengaged, they are less productive, they're making more errors. There's higher turnover that's costing your team and your company money. And it's really simple. It's like talking to the people on your team. Work first and foremost is supposed to make sure that we are resourced. So in terms of time and money, how are your team members doing? Like, obviously we're not responsible for everyone's. Like spending habits and things outside of the workplace. But like, are you getting compensated enough for your workload? Do you have resources to accommodate your workload? I think those are some baseline level questions we need to ask employees and we need to create pathways and space for people to either have side hustles and side gigs, more autonomy and flexibility to pursue those other interests. If we can't pay them more. Or figure out how we can help them outsource, delegate, automate some responsibilities to free up more of their time. The second thing I would encourage leaders to do is ask their team members about the sense of belonging on their team. So we have, like I said, we are, we have this hyper individualistic culture and we say like, oh, there's this meritocracy. That's how we advance. You work hard, you'll be successful. That's not how our country operates.

alyssa-nolte_1_02-19-2025_111526: 14:37

Yeah, that's wish, that's wishful thinking. Let's, let's all be honest. If we're looking, taking a good hard look at ourselves. I actually spoke to a college class a couple of weeks ago and I said, it's not what you know or how good you are at anything. It is who you know, and that's how you're going to advance in this world. So start building those relationships now. I know you're only 19 years old and three years away from graduating, but it starts now.

danielle-roberts--she-her-_1_02-19-2025_121526: 15:00

Yeah, yeah. It's not just about who you know, it's about who knows you, too. So you gotta, like, get out there and be known and make yourself visible. Um, but one of the leading drivers of success above and beyond hard work, like, hard work does not equal success, socioeconomic is the best indica socioeconomic status is one of the best indicators of your future success. So you have to put yourself in rooms with people who are at a higher socioeconomic status than you. That's the game that we're playing. I wish it wasn't that way, but that is the game that we're playing.

alyssa-nolte_1_02-19-2025_111526: 15:31

Right. Pretending or wishing that it was some other way is not going to help you be successful. It's recognizing and being aware of the room, the situation, the, the place that you've put yourself and then being strategic about how you change that situation. If it's not, if you're not liking what you're seeing.

danielle-roberts--she-her-_1_02-19-2025_121526: 15:46

Exactly. Like, how do you create more belonging across those different environments? Um, so, you create belonging by communicating expectations clearly. Um, that includes like your employees understanding what happens when mistakes are made. I think a lot of us are taught that we're not allowed to make mistakes in the workplace, right? Like what is considered a detrimental mistake that is going to affect your job versus what is failing forward for the organization? A lot of people don't communicate that in an onboarding process. Feedback, consistently communicating it both ways and in an emotionally intelligent way. So that includes like what is the How do you feel, what was the impact and what is an ideal resolution for these things? How do we move forward? And then recognizing and celebrating success, even if it's not monetary, like people like to be recognized for a job well done. So I would say, you know, resources belonging, and then finally impact. We put these company mission, vision, and value statements on websites, or you can find them on walls. But rarely do companies like operationalize them or embody them in practice. So I thinking, I think almost having like a values tune up and on a quarterly basis, checking in with your team members to say like, here's the impact that you're making here, the challenges that you worked on this past quarter, and this is how employees can advocate for themselves too. Here's what you worked on this past quarter. Here are the actions you took and here's the result that I had not only on a company level, but like. Let's connect this to societal impact as well. How is this moving our society, another person, or the world forward in a positive way? Because we want, we spend 90, 000 hours plus at work, we want our work to be meaningful. So if we can connect our daily responsibilities to the impact that we're making, people will be more engaged at work. They're human centered skills.

alyssa-nolte_1_02-19-2025_111526: 17:47

There's a lot, um, a lot in what you said that I want to unpack. I want to start with, you know, you talked about a lot of strategies about checking in and building relationships. I've had people that I've worked with before where. They would try those things for, you know, two or three weeks and they wouldn't see instant change in their team or their relationships. And then they would abandon it and then just kind of go back to their, their standard of, I'm the boss, you're the employee, you're going to do what I say. And, you know, everyone has to manage my, my ego or my situation or my opinions rather than, you know, the other way around. How long does it take? Like, let's say you're starting from scratch. Is it something that you can build in a couple of weeks or does it take time?

danielle-roberts--she-her-_1_02-19-2025_121526: 18:32

I think trust takes time. If you were to look at building self trust, if you were to compare it to you going to the gym, right? If after three years, you, you didn't take care of yourself at all and you sweat and you started lifting weights, would you expect to be like crazy muscley in three weeks time? Or, I mean, we would like for that.

alyssa-nolte_1_02-19-2025_111526: 18:55

but that's, I mean, no, that's not really, no one believes that

danielle-roberts--she-her-_1_02-19-2025_121526: 18:57

not sustainable. Yeah, it's not sustainable for your wellness long term. Um, you could probably do something, but it's probably gonna, like, damage your health long term if you were to, like, do a crazy diet fad or, like, a detox. Like, you might see results, might help you feel good for a little while, but it might cause more damage to your health long term.

alyssa-nolte_1_02-19-2025_111526: 19:15

right? But at what

danielle-roberts--she-her-_1_02-19-2025_121526: 19:16

thing, right, at what cost? Same thing with, like, an interpersonal relationship. Say you have a long term romantic partner and you want to behave your change. If you wanted that relationship to last, you wouldn't expect things to change overnight. I mean, you would want it to, but we know that's not the reality of that. The same goes for our professional relationships in the workplace. I would say you really need to give it at least six months time because it's also not something that's dictated from a leader to an employee. It's something that's culture change should be co created because each person, every, every. Every conversation, every process, every policy is culture in action. So like, if you, if you want to say like, here's, we're going to change the way that we're doing things, but I'm not going to talk to you about how it's going over these, these three weeks. I'm just seeing that it's not working. We're doing a disservice to everyone. Um, and it's a waste of time, honestly, like time is money in a business. Like, if you're gonna invest in culture change work, give it space to breathe, because when you do, like purpose driven companies are 23 percent more profitable. That means more money for leaders, more money for employees, better job stability long term if the company's making more money. So like, give it space. I understand that there's like a sense of urgency behind everything that we do under capitalism, but we have to question whether or not that's true.

alyssa-nolte_1_02-19-2025_111526: 20:49

I think give it space and see it through. Um, I was doing a, a project for a major organization and they were rolling out this initiative that the, the leadership wanted. To have done right. And we are, we were working with the individual contributor level and trying to get them to buy into this initiative that the company is doing company wide. And I had someone literally look at me and it was like, I've been here for 10 years. I've gone through about a hundred of these initiatives. I don't want to do this. And you know what? If I just ignore it long enough, it'll go away. And I'm here like, Oh no, my job is to like, get you all on board with this initiative and do that change management piece. And unfortunately. He was right. And six months later, the company abandoned the initiative, even though they were all gung ho about it. And even though I think it was actually a really smart strategy, but they had shown that if you just let it go long enough, they'll give up eventually. So, you know, don't do the hard work of doing the real change management. Just keep flying from strategy to strategy and the employees will just kind of roll their eyes, ignore you, and then move on.

danielle-roberts--she-her-_1_02-19-2025_121526: 21:55

Yeah, well, it's like I'm a plant parent, right? I love plants, and It's the equivalent of like, say you get bug infested, like leaves, and you're like, Alright, well maybe I just need to trim these leaves off with these new initiatives. Or I can like spray some of these oils on it and it'll be good. But the entire time, the roots are infested, and you need to dig it up and change out the soil a little bit. To start fresh. Like you can start fresh. Slap a new initiative and call it employee engagement. But like, if you're not talking to that employee that says it doesn't matter and saying like, well, tell me more about that. Why do you think it doesn't matter? What would matter

alyssa-nolte_1_02-19-2025_111526: 22:34

Right.

danielle-roberts--she-her-_1_02-19-2025_121526: 22:35

that should be of informing the strategies that we put together for these workplaces. And it's, it's going back to that simple. Emotionally intelligent communication that we all say that we don't have time for. But like you said, it comes at a cost long term, whether that's to company bottom line, employee engagement, turnover, a combination of them. We're going to see the impact of it at some point.

alyssa-nolte_1_02-19-2025_111526: 23:06

Well, I think you and I could probably hang out all day. Um, but we gotta, we gotta wrap it up at some point. So tell me, you know, when you think about all of the incredible people that you've had a chance to meet, everyone who you've talked to, or you coached, or you learned from, you know, who is taking back Monday, who's leading the church.

danielle-roberts--she-her-_1_02-19-2025_121526: 23:25

Yeah, um, so I will give you a personal connection and then I will give you somebody that inspires me Just out in the business world So Ryan Steigar is an employee rights attorney at Attorney Ryan And he is really on the front lines on making sure that Workers have rights and that we are well supported and taken care of in the workplace and that we have options to pursue toxic employers, um, and, and change things on a systemic level, which is very similar to what I said about, like, digging out some of those infested roots. Um, he's, and he's just, he does it in a way that's so intelligent and I really admire the work that he, he does for workers. Um, somebody that inspires me on. A bigger business level whose success I would love to emulate is Shay Mitchell, who is the CEO of Bass. I love that she created a product that she is so passionate about with travel. Her team just has a ton of fun. And they get to be creative all day long, doing different campaigns. And that kind of, you know, Goes back to my roots in advertising and marketing. So I just like, I see the stuff that they post all the time. And I'm like, man, this is, this is some genius stuff. Um, so she does good work and she looks good doing it.

alyssa-nolte_1_02-19-2025_111526: 24:42

I haven't given into buying one of those bags. It's like they have something like the weekend or something like that.

danielle-roberts--she-her-_1_02-19-2025_121526: 24:45

I have it.

alyssa-nolte_1_02-19-2025_111526: 24:46

Yeah, do you and I haven't given in to buying one, but it does pop up on my tech talk and I'm like Yeah, that looks good That feels that feels right and you can tell when a company comes across as authentic and like something that you Would be excited about like it shows up in all facets of their

danielle-roberts--she-her-_1_02-19-2025_121526: 25:01

And they post about their team building too, and their employees post about it. And. Having been on a social media team before, you cannot get employees to buy in. Like, you can't bullshit a bullshitter, you would see through that if they were posting. So, I just love the product, I love that it's tied into something that she's so passionate about, and I love that they just have fun doing it. So, that's kind of what I strive to emulate in my work, because if it's fun, like, if it's not fun, what's the point?

alyssa-nolte_1_02-19-2025_111526: 25:26

I Think we got to end it there if it's not fun. What's the point? Um, so Danielle tell us if someone is really connecting with you if they want to do the anti career thing Where can they find you online?

danielle-roberts--she-her-_1_02-19-2025_121526: 25:36

Yes, you can find me at I'm Danielle Roberts across socials or my website danielleroberts. co

alyssa-nolte_1_02-19-2025_111526: 25:43

Awesome. Well, thank you so much for taking back Monday with me. This has been a great conversation.

danielle-roberts--she-her-_1_02-19-2025_121526: 25:47

Thank you, I appreciate you Thanks for joining us on Taking Back Monday, where we say goodbye to the Sunday scaries and hello to meaningful and fulfilling work. If you enjoyed today's episode, let's connect on LinkedIn. I'd love to hear your thoughts. And if you found value here, share the podcast with your network. Don't forget to like, subscribe, and leave a review. It helps us inspire more leaders to join the movement. Until next time, let's take back Monday.