WR 23 | Complex Workplace Scenarios

A great way to start working in an organization is to learn how to connect with the people on your team. It starts from there. In this Ask Us Anything episode, Debra and lisa explore a complex workplace scenario about managing up. Rania is thrilled to be working in an industry she loves and a role where she is engaged and committed to making a difference. She is inspired by the leader and mission of this small wellness company. However, there’s a big hindrance to her happiness and growth: her direct boss. Debra and lisa deconstruct this all too common scenario, offering coaching notes to Rania as well as general advice for leaders to avoid and manage a situation like this.

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Ask Us Anything: Rania

Debra and lisa offer Solutions to Complex Real-Life Workplace Scenarios

I want to tell our readers that, as Debra and I discuss topics brought to us on Ask Us Anything, our goal is not to provide a pat answer but to explore all the dimensions of a situation that could impact how somebody decides to take action. There is no right or wrong here, but we’re offering our experience on what we think could be some things to consider as people bring us their questions about workplaces.

Let me tell you the story about Rania. She works for a small health and wellness company. There are under 30 employees that work there.

The goal of this company is to enhance the sense of self-acceptance, fitness and wellbeing for their corporate clients. What this company does, they’re hired to go into either virtually or in-person offices to teach or facilitate yoga, mindfulness and fitness sessions for employees. This company has made it clear that they want to double the number of clients that they have over the next year. This is the beat that the executive director sets and she wants everyone to march to this beat.

Rania loves her job. She’s helping people every week reach some of their goals and reduce their stress. She feels that this is what she’s called to do. It’s deeply important to her to work in this field, particularly given everything that’s going on in the world. She feels like she’s providing something that the world is hungry for and that she’s meeting a need. She frequently has ideas on how to expand and grow the company’s business because she learns from her clients, their needs and what she’s hearing in the workplace.

She’s understood from the executive director that this company is growing. What happens when she brings an idea to her boss, she’s met with quite significant resistance. The boss has been in the role for under a year and was hired from outside the company. It’s a small company. Rania frequently hears from her boss that she’s thinking above her pay grade. “Your job is to run the programs and leave the business development to the “real” leaders in the organization.” Rania is a bit conflicted and confused about this.

In addition to hearing no to her ideas, Rania’s boss’s often a bit rude and brisk in her tone and one other wellness facilitator who also happens to be a woman. Rania has noticed that her boss seems far more friendly and open to their ideas with the four male employees who report to her. All of this to say, Rania was a client of mine. Her question to me was how does she have a conversation with her boss in which she can both get feedback on what approach she should take to get her ideas for building the business and in her mind following what the executive director is asking everyone to do?

How might she also have an honest conversation with her boss in which she can share some feedback up to her boss on the impact of her behavior? The impact is she’s feeling a bit shut down and losing her sense of being enthusiastic and engaged. That’s the situation I’m bringing to us, Debra. What are your initial thoughts when you hear this?

It’s important that your work connects you with a sense of purpose and direction.

I’m putting myself in Rania’s shoes. I can relate to this. Something similar plays out with people I’ve worked with. I’ve been in a similar situation and with the clients I’ve seen. What I find particularly interesting/troubling about this situation is that we have an employee who cares so much about her work and the success of this organization that she has sought coaching. We have someone so self-motivated and passionate about the work she’s doing. There is great meaning in it for her. She is connected to a sense of purpose both in the work that she does and is providing.

Based on what you’ve shared, it seems to be a connection to the values and vision that the executive director has set out. When you have an employee who is buying to the senior leadership’s vision perspective, motivated by that, feels a sense of connection to it and is getting stopped at that other level, that to me is a troubling scenario. If I was the leader in this organization, I want people to feel that sense of connection and the meaning and purpose of work. I want them to bring their creative ideas.

One question that comes to mind is maybe this isn’t the right role for her and she has a lot more to contribute. In a small organization, we’re already getting stuck in some hierarchy and structure here. Maybe there needs to be a lot more fluidity in the way that this organization is structured for one thing so that we don’t have these blockages. That’s another thought that’s coming to mind for me.

I’m imagining it from both Rania’s situation but if I was the leader and my company, these are the people I want to bring on board. It would be troubling to me if somebody with that much interest in the success of my company was starting to feel as though they weren’t being able to contribute at their best and weren’t being heard.

I’ve seen the situation many times in my working life. Similar to you, I’ve been in this situation where there seems to be something at play here. With Rania’s boss, I’m wondering if the boss feels threatened because Rania is full of enthusiasm and energy. She loves her job and got all these great ideas. She shared with me some of the ideas and I thought, “These are quite brilliant.” It’s a little bit I know about the wellness industry. As we were having the conversation, I asked her to do this thing, which you and I ask people to put themselves in the other person’s position.

As neutral as possible, what might be some of the things that might bring this behavior up? When I do this with a coaching client, it’s not necessarily to get them to be fully empathetic with the person that may or may not come but it’s to enlarge their thinking. At the very beginning, Rania felt that this person was an obstacle, didn’t like her and thought she was too much. I tried to help her think about all the reasons for this so she could have an enlarged sense of what might be at play.

WR 23 | Complex Workplace Scenarios

Ask Us Anything: Regardless of the role you’re in, being part of a feedback culture makes the workplace so much better because you’ve already determined that it is safe to bring concerns and issues.


We don’t know what is at play because there hasn’t been a conversation between Rania and her boss but that was where we did a bit of exploration, which enabled her to have more of an open mind about this. The other thing I suggested to her was to think more broadly about her career. Is this job a stepping stone? Does she have aspirations to become a leader? Think of the broader arc because sometimes we’re two feet away from the problem.

Even if it’s 10 feet or 20 feet, it doesn’t always have to be 5,000 feet, take a step back and look at the broader perspective and context in which this situation is happening. We did a bit of work around that. Ultimately, she wanted some specific things to go into a conversation with her boss. Before I tell you what she decided to do, one of the things she asked me was should she go above her boss’s head and go directly to the executive director with whom she deeply feels like she’s aligned with and wants to deliver on the mission of the organization? What are your thoughts about her jumping over her boss to have a conversation?

I don’t have a perfect answer for that. A lot of this is understanding the dynamics in the organization, relationships and paying a lot of attention to that. What is the feedback culture in this organization? The way that any individual might feel about feedback and the feedback culture established in an organization could be very different. We might go about it thinking, “I’ve read all these amazing things on feedback. I followed amazing shows like Work Revolution and I get all the great ideas.”

That doesn’t mean everybody else in the organization is operating that way or that culture is reflective of that. There’s a lot of dynamics at play here. For me, I would focus on building a relationship with the executive director. Looking for opportunities to get to know that person and to get them to know you or in her case, Rania a little bit better. I don’t know that I would go over the boss’s head and sit down formally with a formal meeting to say, “I’ve got some issues.”

That would not be a first step that I would take but I would be looking and thinking about ways that I can get myself in front of the executive director that I can get my work visible in a way that is not going to trigger the manager too much. I’d be looking for opportunities to do that and build that relationship and rapport. The first step here and this is probably where you’re going is a sit down with the manager in how to manage that conversation, what to do to prepare for it and think about possible outcomes.

Rania’s first question to me was, “How do I give my boss feedback?” I turned it back to her and said, “What if you had a conversation with your boss in which you’re asking for feedback? I’ve brought a couple of ideas. This is what I understand the organization is looking for that we’re in growth mode. How can I present my ideas to you in a way that they might be considered?” To start a conversation on maybe looking at feedback that she can do to become more compelling. This might give her the lay of the land.

Let go of your expectations of a situation that is not panning out the way that you ideally envisioned.

If her boss then says to her, “I don’t want your ideas at all,” this gives her something else to work with like, “Do I want to work in an organization in which I am shut down?” This is a whole other set of considerations. The other thing that was interesting to me is that Rania was under the impression that if she worked in the wellness field, she wouldn’t encounter issues like this. She had this idea that this whole domain was a place where everyone was open, wants everyone to grow and be well.

It was a bit of a rude awakening for her that even in an organization that purports to be about well-being, you can encounter situations in which you are shut down or not supported. Regardless of the field you work in, there are great bosses and bosses who have yet to become great. Imagine if you’re going to work in a particular field that some things are going to be better by the field you work in. She had a bit of grieving to do around this and explore her feelings.

I love the fact that you used the word grieving. Letting go of our expectations of a situation that is not panning out the way that we ideally envisioned. It’s so important to be able to do that. I thought of the saying about the kids of the cobbler not having shoes. I’ve worked in HR-focused companies. Did we have HR perfectly down the path? It doesn’t mean anything but that’s very interesting learning.

When she was able to talk a bit more about her feelings of disappointment and letting go, she was able to think about what she wanted to do. Here are a couple of things that she’s working on over time. One is I suggested to her that work is not episodic. You don’t do something and it’s done. Your relationships at work are a practice. We spent a lot of time talking about what kinds of relationships she wants to have at work regardless of whether it’s peers, the executive director or her boss? What can she do to create an environment in which she can have the kinds of relationships she wants?

We don’t control other people. As we were talking upfront about what her boss might be feeling that’s in the role less than a year, might be feeling a sense of like, “I need to get this right.” One of the things that Rania could do, which she agreed is to help her boss be successful and spend some time asking her boss, “What is it that you need to see from me and the team to be successful?” To be more of an ally to her boss as opposed to feeling that her boss was an obstacle was useful.

What’s also of interest in this whole situation is that regardless of the role you’re in, being part of a feedback culture makes the workplace so much better because you’ve already determined that it is safe to bring concerns and issues and that they’re receptive. They might not be acted on but at least there’s a place to say things. I’m going to make one caveat about feedback and ask you for your thoughts on this. I remember learning years ago that the most effective feedback is observational. This is either constructive, developmental or recognition feedback.

WR 23 | Complex Workplace Scenarios

Ask Us Anything: Leaders are going to have employees that they don’t know how to manage very well. That doesn’t mean there’s anything wrong with that person. It means that you’re not the right leader for that person.


If I were to say to you, “Debra, you are a ray of sunshine.” You’re going to be like, “That’s nice but what the hell did I do to earn that?” If I were to say to you, “Debra, you are always available when it is a crisis and I can count on you. Your ideas enhance this business and make us look good to our customers. Whenever there’s a very difficult situation and we don’t know what to do, you’re the first to step in.” The impact that your behavior has, the choices you make and how you show up make you a real ray of sunshine. That’s very different.

You know what it is that is earning you the accolade. I could have done the reverse and given you all the things you don’t do and this is why but I don’t have any of those to offer you in all truth. I also suggested to Rania that she learn to give observational feedback. It’s never useful to say to somebody either, “You’re a ray of sunshine or lazy.” That’s talking about the person and it’s not actionable but to start developing her practice of giving her peers both recognition, developmental feedback and to normalize it in her working relationship so that it becomes a way that she interacts with other people.

I loved the part about getting to understand more about the boss’s top concerns and issues. What does the boss think is the most important thing to achieve? This question is very cliché but it’s still a good one like, “What’s keeping the boss up at night?” Not to ask it in that way necessarily but that’s part of what you’re trying to uncover. “How can I then be part of that solution or contribute in a meaningful way towards achieving that goal?” If she can build that bit more trust and maybe get some wins in her belt with the boss, that might develop the relationship further.

The vision I’m getting with the boss is very tightly holding the reigns here, being a little reluctant and maybe doesn’t know what to do with this exuberant employee. Not every boss-employee relationship is going to work out and be magical. Leaders are going to have employees that they don’t know how to manage very well. That doesn’t mean there’s anything wrong with that person. It means that you’re not the right leader for that person.

It doesn’t mean that that person doesn’t have incredible things to offer but maybe this isn’t going to be the situation or dynamic that’s going to allow that to come out. She can only do with what’s in her control. What about worst-case scenario-ing it? Did you talk a little bit about that? What happens if it doesn’t go well or that person’s not receptive? How many times do you try?

We did come out of it a bit obliquely because one of the things Rania asked me was, “Should I tell my boss that she seems to prefer the male employees over the female employees? It’s noticeable.” That struck me as a bit of a career-limiting move. When you’re trying to build a relationship, you want to start at the foundation. You don’t want to show up with a wrecking ball before you’ve even started to look at the plans and figure out where the bedrock is. I’m not saying it’s not a legitimate topic but not to start there because that would lead to a worst-case scenario.

Ad hoc conversations are important too. Not everything has to be a formal sit-down.

There’s a lot of defensiveness like a she-said situation. I also wanted her to think about if you’re in the business of wellness, wellbeing and helping other people, how would you turn that back on yourself? What is your self-care if something goes sideways? Sometimes we’re prepared to walk away from a situation because it doesn’t fit and she’s not prepared to walk away from the situation. She loves her job. What would you tell her not to do? Don’t bring up, “When you talk to Jamie or Siddique, you were way more.” I didn’t think that was a good idea but what would be some things that you would suggest she avoid or hold off on?

I would avoid anything that seems like it’s critical for past scenarios and conversations. This person already seems a little bit on the defensive. Otherwise, if this boss wasn’t already in my mind feeling a little bit protectionistic, what she would be hearing from that person is things like recognizing the effort and enthusiasm. “You have a lot of interesting and great ideas. My job for the next 6 months to 1 year is to achieve these things.” To also be like, “I don’t want to discourage this. This is the thing this company needs. We want to encourage these things. How can we work together then so that we can get some of these wins under our belt? Maybe these are things we can look at for the following year.”

Give her a little project to do. “Flush that out a little bit more. I’d like to hear more about that.” She’s not hearing any of these kinds of things. That tells me that she needs to be careful and pace herself. We don’t have to accomplish everything in one single conversation. The first conversation’s going to be more about understanding the receptivity. “If I’m going to propose ideas, what would be the best way to do that? How receptive are you to these ideas that I might have? How can I present them in a way that would be most practical?”

First, starting with the questions that she has about what’s on the boss’s plate? What are the boss’s priorities? How can she contribute? I would want to keep steering the conversation more to that. “What’s the best way for us to work together and share feedback? I want you to know that I’m open and receptive to feedback. Should we meet regularly? What would be the best cadence of our meetings? Is that something we should be scheduling out ahead of time? Should we do it ad hoc?”

Remember that ad hoc conversations are important too. Not everything has to be a formal sit-down. Those ad hoc moments when we’re having day-to-day conversations about things are also opportunities to say, “I’d love your feedback on this particular aspect of that, for us to have an opportunity to maybe dive a little deeper into that and understand a little more about your thinking on this.”

We’re looking for opportunities to work that into conversations. My kids do this to me all the time. If I say, “Let’s sit down and have a conversation.” They’re like, “My god.” If I’m washing the dishes and we start talking about something, it feels more natural. There’s so much more receptive. We’re in the car and we start a conversation. When it’s a formal thing, we’re automatically like, “What’s coming? What do I have to prepare myself for?”

WR 23 | Complex Workplace Scenarios

Ask Us Anything: Build that rapport of connection with your colleagues that you can establish. Feedback is best amongst peers.


That’s like when somebody comes to you and says, “Can I give you some feedback?” They could be there to tell you that you’re a ray of sunshine.

“I don’t want to hear it. I don’t think I could handle it. I’ve had enough. I’m maxed out.” Everybody is feeling so maxed out.

I’m going to offer one last thing on what not to do. Rania said, “What if I suggest something and it’s turned down? I go to one of the male employees on my team, have him suggest it and it’s accepted. Then I have a got you to say to my boss. When I said it, you didn’t want to do it.” I don’t believe in trying to get you people. This is not a situation where you’re trying to prove abuse or outright discrimination. There are some observations that Rania has made about her boss’s behavior. The bigger thing here is who does she want to be in her role? How does she want to grow? How can she have a good relationship with her boss?

The other thing that would be helpful for her or anyone, which I borrowed from having worked in healthcare for a long time is what we call clinical supervision? You bring an issue that you’re having in your practice as a professional and she’s a wellness professional, to your boss and says, “Help me work this out. Somebody came to me in a session and was having a problem with such a thing. I wasn’t quite sure what to say to her. She came to me when I’m unhappy at home. I’m so glad that I can come to these sessions. What do I do in cases like that?” Building a relationship with her boss about the actual work could also go a long way in establishing a solid relationship.

That leads me to one other thing that you sparked for me. If you develop a good relationship with your colleagues, you could ask them for feedback and sponsorship for your ideas. You might be able to say, “I don’t know if you noticed but I brought up an idea in that meeting and I felt as though it got shut down or there wasn’t an opportunity to explore it further. I’m not sure it even landed with people. I’d be interested in your honest, open feedback. What do you think of that and maybe have some conversation about the idea itself but also it could be how I brought it up in the meeting. What were your observations on that? Do you think I should have done a little differently? If you think it’s a great idea is it something that maybe we flush out a little bit more amongst us or have some conversations?”

This is another area where maybe you need to be careful of how you would approach it but maybe if a few colleagues start to think, “I could see how this could be helpful and how we could even do this. It wouldn’t cost a lot of money.” Maybe the feedback is going to be, “It’s a great idea. We don’t have the budget for that right now.”

If you develop a good relationship with your colleagues, you could ask them for feedback and sponsorship for your ideas.

You’re probably going to get a bit of information either way that you can work with. Build that rapport of connection with your colleagues that you can establish. Feedback is best amongst peers. It’s openly done in a way that we can comment, be very straight and upfront with one another and not worry too much about people’s feelings getting hurt about that. We do it respectfully and it’s part of the culture. If we can start to build that a little bit amongst our colleagues, that’s helpful.

We have a lot to say about this topic and some people might say to us like, “That seems complicated and convoluted.” The majority of issues that come up at work are around human interaction, people dynamics. They are nuanced and complicated. These are people we spend a lot of time with. Once we can figure out the best ways to enhance our relationships at work then things run smoothly.

That’s why we’re having a long conversation on this because I could have said to Rania, “Do what your boss says and keep your nose down,” which is probably what her boss is saying to her. “Be lucky that you have a job.” That is not how we’re going to create the world that we all want to be a part of. I appreciate your thoughts on this, Debra.

Thank you for bringing this scenario. It sounds like she got some great coaching from you. That’s awesome. We want to see people coming to work with this much enthusiasm and interest in the work that they’re doing. That’s what we want people to do. We don’t want to shut that down. I hope she finds an avenue.

Thank you, Debra. For those of you who want to bring a thorny or uncomfortable issue to Debra and me to have a conversation and offer some of our thoughts, please reach out to us at TheWorkRevolutionPodcast.com. You can also find Debra and me on LinkedIn and Facebook at Work Revolution Podcast. Debra, thanks for having this conversation.

Thanks, lisa. Please send us your comments and gnarly issues. Give us some meaty stuff to dive into. Until next time.

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