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180. Entitlement

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Ep. 180 – As leaders, it’s crucial for us to understand how to identify entitled behaviors and effectively manage employees who are exhibiting those behaviors. All of this, while navigating the ever-changing dynamics of today’s workplace.

In this episode, we’ll explore what entitlement looks like, how to identify it, and strategies for preventing the hiring of entitled employees. We’ll also discuss how to effectively manage conversations when faced with unrealistic demands.

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Episode 180 Transcript:

Ramona Shaw [00:00:00]:

This is episode 180 of The Manager Track podcast. Today, we’re gonna talk about entitlement, specifically how you as a leader can manage or should manage and what to pay attention to when it comes to entitled employees. Here’s the question. How do you successfully transition into your 1st official leadership role, build the confidence and competence to lead your team successfully and establish yourself as a respected and trusted leader across the organization. That’s the question, in this show provides the answers. Welcome to the Men to Track podcast. I’m your host, Ramona Shaw, and I’m on a mission to create workplaces where work is not see it as a source of stress and dread, but as a source of contribution, connection, and fulfillment. And this transition starts with developing a new generation of leaders who know how to lead so everyone wins and grows.

Ramona Shaw [00:00:49]:

In the show, you’ll learn how to think, communicate, and ask. Ask the confident and confident leader you know you can be. Welcome to this episode of The Manager Track podcast. In the many conversations that I have at organizations, with leaders that I work with, but also with colleagues or friends who are in their respective leadership roles at work, the topic around entitlement has come up more so than I think ever before. And I thought it was interesting because I know this idea that some stereotypically call this out. Some of the younger generations are feeling more entitled in the workplace, and how older generations who are now in their forties and beyond are navigating the different dynamics as well as the different needs, demands of employees in a workforce, and more specifically, the people on their team that they’re managing and that they wanna support and help them grow in their career when the mindset, the approach to working is so different from their own, and how that stretch is becoming more and more training or challenging. Now this has been a topic for a while, but for whatever reasons, this has been coming up more so in the last, I wanna say, maybe 4 to 5 months. And I got to the point after publishing the episode on emotional labor, and I received comments on that as well.

Ramona Shaw [00:02:10]:

I thought we should also address the conversations around entitlement, specifically from the perspective of a team leader who is challenged by employees who feel entitled. So that’s what we’re gonna cover in this episode. I’m gonna start off talking about what entitlement is, how you can identify it, how it shows up, and then we’ll go a bit deeper into strategies to prevent even hiring entitled employees as well as how you specifically manage or have these conversations when people make demands on you and on the job or the company that you cannot meet. So let us dive in. I always love starting off with some statistics. I think it it gives a good mental frame of what is really going on or what are some of the data points that we’re looking at here. So let’s start off with some statistics, not just on a entitlement, but overall how the complexity of the workplace and how personal lives and needs are also intersecting and increasingly overlapping with the professional world. So first, the American Psychological Association’s Work and well-being survey in 2022 revealed that 81% of individuals said that they will be looking for workplaces that support mental health when they seek future job opportunities.

Ramona Shaw [00:03:30]:

Also, BetterUp says that 80% of employees would would rather have a manager who help them find meaning in work than a 20% increase in pay. So mental health plays an increasing role, meaning and purpose at work plays an increasing role that the managers have to deal with. In addition to that, a recent survey by the Addison Group and Colton said that 40% of millennials expect the promotion every 1 to 2 years, and that that generation is also more likely than the older generations to say that raises promotions and bonuses should be provided more than once a year. So as I said earlier, we’re seeing a different generation in the workplace. We’re seeing different needs and demands. We’re seeing more complexity and more demands on leaders. Now let’s dive into the actual entitlement and what that looks like. So with that Again, this on one hand points out the increased complexity of and demands on leadership, and It’s also a great segue into the conversation of entitlement.

Ramona Shaw [00:04:39]:

Entitlement is by definition in an inflated self regard and inflated requests for perks and benefits. And entitled employees likely believe in their right, even if unsubstantiated, to receive privileged treatment. So I’m gonna share some of the examples here that you may recognize in the people that you work with or maybe your former self or younger self as well. Here’s some example of how entitlements show up. The first, it’s the expectation that a promotion or a pay increase is due and deserved with average performance. So we don’t need to go the extra mile or sort of level up, just doing a mediocre or satisfactory work will or warrants a promotion or increase, that bonuses should be paid regardless of a company situation, that breaks during the day or vacations can be taken whenever they want to regardless of the impact this has on other people. They often also want to only work in highly visible positions or do work that’s interesting to them, they may also believe that they have exceptional skills. Now this is not an all encompassing list, but these are some of the common traits that we see in entitled employees.

Ramona Shaw [00:05:52]:

Not all of them need to apply, but if 1 or 2 of them apply, you probably already have a bit of a challenge at hand and something that you need to manage well and be on top of. It’s not to say that if you have someone on the team that you consider to be entitled, that that’s the way they’re going to be and there’s no way to change. Sometimes there might be a bit of naivete of people who are new to the workforce, of what it’s like and what the expectations should be or can be, and they have to learn that. They have to understand the dynamics and learn how business works. Then once they do, they may totally adjust the expectations that they have and the request and demands that they make. So that’s important to keep in mind when you have people that you think, oh my gosh. I can’t believe they asked that. They can’t believe they said that.

Ramona Shaw [00:06:39]:

There might be just a lack of information. They may just be lacking the experience or the information to properly assess what’s appropriate. And with that said, let’s dive into some of the strategies for you to handle such situations and work with entitled employees. First of all, I wanna piggyback off of what I just said. It also means it isn’t a lost cause. That also means to have an open mind and come from place of curiosity versus judgment when you first get confronted with a demand or an a request that you feel comes from a place of entitlement, instead of seeing it as black or white, to really inquire and ask them what the basis is for the demand. Ask them to explain, to lay out their thought process, their rationale for it so that you could see where they might be coming from and then specifically address the points where you disagree or where you have a different perspective and to share specific facts that will highlight where that discrepancy is. Now on top of being curious and just putting the ball back into their courts to ask them to elaborate further, what’s on you ideally from the beginning even during the hiring process and during the onboarding process is to be really clear on the expectations and standards.

Ramona Shaw [00:08:02]:

This includes how do you ask for time off, how are breaks during the day handled, how do you handle sick days, who should be informed when, who needs to hand off work or inform and provide updates of things that might be pending. What is the expectation for such situations? You can’t really blame or judge someone for doing it differently than what you would have preferred if you never laid out to them very explicitly of what your preference is and what your expectations are. It may seem like common sense to you, but common sense to you does not mean it’s common sense to everyone else, and especially if you work in a diverse and intergenerational environment where you work with people who have a different mindset on work, on their life overall and their priorities. So lay that out as clearly as you can. Ask them if they have questions or if they have concerns, and then refer back to them whenever you see that they’re deviating from what was agreed are committed to in the beginning. So one is we’ve just talked about more tactically how the work should be handled, but then also and equally important is to talk about what the promotion cycle looks like, what is required to get a promotion. And this is really hard to do if you have no framework in place. And sometimes companies are really good with this, established companies, and sometimes smaller companies who are a little bit more scrappy, they don’t have any frameworks in place, but there is not a company size that you need to reach before you can introduce a framework for promotions.

Ramona Shaw [00:09:43]:

And you also don’t need to wait for a company wide framework. You as a leader are going to be responsible for this. If if you say, hey. On my team, to move from a junior position to a full position to then a senior position to then a team leader, whatever that structure may look like. Here are the requirements in terms of individual contribution, team contribution, and likely also organizational contribution and leadership. What are the different dimensions? What are the requirements to in order to get there, what may be company wide written or unwritten rules of promotion titles look like, who needs to approve the promotion, what happens behind closed door. Be as transparent as you possibly can. Now quick side note, of course, feeling the same way, do as much collaboratively as you can so that there’s consistency within your department or within your broader team or ideally the whole organization, if no one else does it, then goes have set something up that works for your team.

Ramona Shaw [00:10:47]:

So being really clear upfront and as early as possible in the employee life cycle. The behavioral norms, behavioral expectations on how to do work can interact with others as well as expectations on performance and then what the promotion or salary increase of bonuses, what the process is for promotions, salary increases, and bonuses. So that is at the core. These are the things that you can do upfront to prevent these kind of misalignments or tough conversations down the road. Now be prepared to repeat yourself. Like, just because you said it once, just because you shared a document where this is listed, it’s not going to be good enough. You have to repeat it over and over. If you see someone deviate, you have to repeat it multiple times.

Ramona Shaw [00:11:36]:

If someone deviates from it, don’t let it slide because The moment you let it slide, you’re sending the signal. You know, it’s gonna be okay if you don’t follow the expectations. If you don’t meet them, the expectations are not that serious anyways. That’s see underlying message that you send when you let things slide without talking about them. So be prepared to repeat. And then lastly, be prepared to have the tough conversations too. So if you lay it all out, you’re explicit about the expectations, the standard, the processes, what it takes, you’re also explicit about where they fall on that scale. If you think they’re performing their job on a scale from 1 to 10 with 10 being they’re mastering it and 1 being they’re doing basically nothing, if you think they’re at an 8, the other person, your employee, if you think they’re at an 8, you gotta make sure that your direct report would also enter that question with about an 8.

Ramona Shaw [00:12:34]:

If you think they’re performing at about a 5, but if I were to ask the employee, they’d say, oh, no. My boss is super happy with me. I’ve never received any negative feedback. I don’t know what else to do better better than what I’m already doing. I think I’m at a 9 or a 10, then you got a problem. Right? Then we gotta go back into more transparent, direct communication without the sugarcoating. You won’t do yourself any service without the sugarcoating. As a caring and driven manager, I know you want to strengthen your leadership skills advance your career and lead a high performing engaged team.

Ramona Shaw [00:13:12]:

And in order to do that, as a leader, you need to lead with a system, not by shooting from your hips or reacting to everyone else around you. To do so, you need to, first, learn what should go into a leadership system, and second, develop your own. Now the good news is that I teach you one must have part in your leadership system in a concise, actionable, and yet comprehensive course focused on running successful 1 on 1 meetings with your direct reports. It includes over 67 minutes of tactical leadership training plus a set of resources to make this as easy and immediately applicable for you as possible. You can either watch the video lessons or listen to it through a private podcast feed on your phone. You can get your hands on this course, which I want every single manager to have. For a nominal $19@ramonashaw.com/oneone. That’s 2 times the number one.

Ramona Shaw [00:14:11]:

You can check the show notes for the details or head on over to ramona shaw.com/oneone to get started right now. I’m gonna quickly recap. What you can do proactively is get really clear on what are the expectations, what are the processes, then repeat those, address when any of this is not being met, have a conversation about it, give regular feedback so they know where they stand, and when undeserving requests are being made, first, be curious, put the ball back into their court, ask them to give you the basis for the requests and you see how that fits into what they already know about the organizational processes and what justifies the request. Stay curious and see maybe there’s actually something to it that is a blind spot to you. But if not, repeat the expectations or the processes yet again. And if it’s not hitting home, then not learning and adapting to it. Also, don’t shy away to have conversation, a bit of a heart to heart with that person to say, it seems that we’re unable to meet your expectations, and we don’t have any wiggle room here. This is what it’s going to be, but what would you like to do? And let them think about that.

Ramona Shaw [00:15:24]:

Is potentially, this is just not the right organization, not the right team, and you can have that conversation. If someone is entitled and they’re not seeing it and not willing to adapt. It’s going to hurt you, your team, and the company overall, and you have to entertain the idea and have the conversations about potentially transition that person out of the company. These are some specific tips to manage entitlement or entitled employees on your team. And I wanna emphasize it just one more time. If someone keeps doing it and then not learning, you don’t have to bend over backwards. You can literally say this is not the right fit. Because the moment that you start to give in or adapt, other people will pick up on it.

Ramona Shaw [00:16:11]:

And now you run the risk of unfairly treating 1 employee over the other just because it’s the squeaky wheel because they’re the loudest or the most demanding, and then that can lead to pay inequality or overall inequality in terms of benefits or perks or tolerate a behavior that only applies to 1 person’s gonna not the others. So this becomes a bigger issue and can easily and quickly lead to frustrations on your team. For someone may say, like, I’m not putting up with this. I’m going to leave. I don’t wanna work with someone like that. So, you know, hold your grounds there, be communicative as much as you can, try to figure it out and solve it by being very explicit. And if it doesn’t work out, it may just not work out. Now the best way, of course, would be to identify entitled employees in the interview process so we prevent hiring them in the 1st place.

Ramona Shaw [00:17:09]:

Think about if this is something that you notice on your team, right, and you feel like, hey. Yeah. This is a challenge or something I need to pay attention to. See how you can weave in questions into the interview process where you would pick up how someone may view themselves, their own regard, as well as the expectations that they have on privileged treatments. Here are some pot potential questions. Tell me about a time you had a boring work assignment. How did you handle that? An entitled employee will likely focus on their efforts to get that boring work off their plate. A way better answer or an answer you would be looking for is to say, well, sometimes we all have to do our share.

Ramona Shaw [00:17:49]:

We all have to do some boring work. And even if it’s boring work, the team required it. You know? They’re demonstrating that they’re a team player. And so at least for a feasible or appropriate time, they took care of that boring work and did so well. Another question might be, tell me about a time when you did not meet the performance metric and what each you do. If they’re unable to share any time where they did not meet a performance metric, investigate further. Right? Ask them how their performance was was measured. Dig into this a little bit more.

Ramona Shaw [00:18:22]:

Most of us had moments when we missed the deadline or a a project took longer than we thought or something got in the way and we didn’t meet the metric. So that is good awareness to have. If they are blaming other people for a wider performance wasn’t up to par or work situations, but don’t take any ownership for that result at all, that’d be a red flag. Now another question could be, tell me about a time where you were hoping for a promotion, but you did not get it, and what did you do? If they’re very junior, and don’t have a lot of work experience. This question might be a little harder for them to answer. But if they have miss a good amount of work experience, This could be a question that works. And if they finger point or said that they left the organization, that we and suboptimal response. If they said that they wanted to better understand what the gaps were and then focused on bridging the gaps and meeting expectations in the next cycle, that would be the answer that we’d be looking for.

Ramona Shaw [00:19:23]:

Now I’m gonna go back to what we talked about in the beginning of the podcast. The complexities and needs of leadership continue to increase, and it’s becoming a a tougher and tougher job, and not knowing how to lead well, not getting the support, not getting the training, not investing in building the skills will likely hinder your career progression and the effectiveness you have in your role and the relationships that you’re building across the organization or even the industry. Get the support. Of course, I highly recommend joining a training such as the leadership accelerator for new managers or our leadership advisory program for mid level managers or working with a coach directly or a mentor or a group of managers in your organization or in your field where you can have a dialogue about these things and learn from each other. There’s so much that you can take away and become more proactive in addressing the inevitable challenges that will come your way as a people leader and trends and themes such as entitlement in the workplace, it are things that I dare to say will likely cross your path. So being prepared and doing what you can to prevent or mitigate the issue early on is key to your and as a side note, also your well-being and job satisfaction as well because this can be fairly frustrating to deal with. If you have any questions or comments on this, please don’t hesitate to reach out. My email and contact details are in the show notes, and I’ll be back next week with another of the Man to Track podcast.

Ramona Shaw [00:20:52]:

Bye for now. If you enjoyed this episode, then check out 2 other awesome resources to help you become a leader people love to work with. This includes my best selling book, The Confident and Competent New Manager, which you can find on Amazon or at ramona shaw.com/book, and a free training on how to successfully lead as a new manager. You check it out at raymondashaw.com/masterclass. These resources and a couple more, you’ll find in the show notes down below.


1. Have you encountered entitled employees in your workplace? How did you handle the situation?

2. What are some common traits of entitled employees that you have observed or experienced?

3. How do you differentiate between entitlement and legitimate requests or expectations from employees?

4. How can leaders effectively address entitlement without creating animosity or resentment among team members?

5. What strategies can leaders use to prevent hiring entitled employees in the first place?

6. How can leaders create clear expectations and standards to manage entitlement in the workplace?

8. How can leaders address the increasing complexity of personal lives and needs intersecting with the professional world?


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