WR 20 | Complex Workplace Scenarios


Steve is starting a new consulting gig as he kicks off the next chapter in his career, having just left a large financial institution. As he prepares to lead a critical project for his client, he is facing a challenging people-related issue that has the potential to impact his success. If this opportunity works out well, it may be the start of his new consulting business. Debra and lisa set the scene and offer strategies and insights to help Steve navigate this delicate situation and set himself, and those around him, up for success.

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Ask Us Anything: Steve

Debra and lisa Offer Solutions To Complex Real-Life Workplace Scenarios

We have a scenario to discuss and provide some of our amazing wisdom to the scenario. For this Ask Us Anything, I am utilizing a situation that happened with a client we talked about. I’m going to lay out what that situation is and a little bit about what we talked about. You and I are going to build on what we think of the situation, and what advice we would have. We fully recognize that there are always so many sides and perspectives to every story. We don’t know them all but that’s life.

When we go into situations, we don’t have all the facts and everybody’s perspective. We are going to have to make a few assumptions. The thing is, as you go through a situation, you get more information, so you continue to change your perspective maybe. That’s why we have to be open and receptive to that. I’m not going to give details of places and stuff. I’m going to keep some of that a little high level.

This is a situation I encountered with a client named Steve. He negotiated a contract, let’s say consulting gig, in a small financial services firm. He was pursued by this organization based on his reputation with a much larger financial services firm that he recently left.

He had led some major change initiatives. In particular, major IT systems change. He has certain expertise that is attractive to this organization because they’ve been trying to do this implementation for a while. It’s not going well. They’ve had some major setbacks. They want to bring him on board. Ultimately, Steve is looking at doing his own consulting. He’s in a period of transition but one of the things he’s thinking is this might segue him nicely into having his own consulting business moving forward.

WR 20 | Complex Workplace Scenarios

Ask Us Anything (Steve): Most people want autonomy. But you have to give over control and autonomy so that you can be able to show up at your very best. To be able to give people what they want.


He’s confident about his ability to deliver in this particular scenario, given his areas of expertise, experience and technical know-how knowledge. However, there’s a little bit of a situation that might be a little prickly with the people dynamics. What’s always going to be the hardest part of any situation is the people. What he’s been told is that there is an employee there currently who’s been there for a while, I don’t know exactly how long. I’m going to call this person Sue because I don’t know her name and it’ll be easier. Sue is described as doing three different jobs.

For the most part, she is keeping this project afloat, although out of her depth. Some of the strain is showing and maybe being labeled as a bit of a problem, a bad attitude coming through. The executive team, who Steve has been meeting with is saying, “We’re not sure about this person.” They’ve left it up to him to say what this person’s future looks like in terms of their participation on the project and even whether they continue with the organization or not.

He’s walking into this scenario. Let’s be clear that the ideal scenario for him is that this person stays, that they work well together and it’s a great asset. That’s not necessarily a foregone conclusion. It might not work out that way but that would certainly make his life a lot easier. Otherwise, it leaves a hole that is a bit of an additional setback. The one other little bit of detail I’ll add to this is that they’ve been introduced and he got a bit of a chilly reception from her, not a great warm vibe.

He’s starting with the organization and taking over this project is not something she was aware that they were going down that road and making those decisions. He’s arriving on the scene and it’s a surprise to her. That’s an important piece of this. To kick us off on this, I thought back to something Mira Brancu said in an episode we did on navigating office politics. She said, “You got to pick your head up, look around, pay attention to what’s going on and in particular, understanding the system that you’re part of.”

We got to pay attention. Attention for me, I think about a couple of things. Paying attention to what’s going on for me. How am I feeling? How are other people feeling to the degree that I can understand that and make some assumptions? How does this situation feel? Let’s start from there. How is he feeling? How would we guide him through that? I don’t think some people take the time to digest and think about that.

First of all, congratulations to Steve for landing a role in which he sounds qualified, in which he’s seeing the arc of his career and how this might fit into it. He sounds like somebody who’s got a fair bit of self-awareness. I love his ability to articulate that he is concerned about the relationships going in. He’s able to say that’s going to be a success factor for him. I have to say that Sue has my empathy. She hasn’t been set up for success. If she was blindsided by not knowing that Steve was going to be hired, I’m not surprised that he got a bit of a chilly reception from her because she’s a little on the back foot.

This is not a case of somebody’s right and somebody’s wrong. This is a classic, typical work situation where it’s the people piece. One thing somebody said to me years ago, which I love, about workplaces, workplace dynamics and organizational behavior was, “Lisa, it’s not rocket science. It’s harder than rocket science.” I’m going to start by saying that.

The other thing I would say about Steve is he’s probably preoccupied with a couple of things. One is, if he’s thinking longer-term about launching his own business, he wants this project to be a success. He’s been given carte blanche. He’s been told that if it’s not working with Sue, that he has the ability to either replace her or put the pieces in place that are going to be successful.

He also probably wants to come across as somebody who can work with others and fit into the existing culture. He’s probably got some things that he needs to think about before he engages in any conversation with Sue. Those are my opening thoughts. When you think about this situation, given you’ve had this conversation with Steve, where did your thinking help shape the conversation you had with him?

Managing workplace dynamics is not rocket science, it's harder than rocket science. Share on X

We had talked a lot about how he felt going into this because there was a lot of decision-making to go along the path as to, is this the right move? We’d already done a lot of that questioning and thinking. He’s feeling positive about this move. This gets maybe into number two a little bit. How are other people feeling? Imagine being in Sue’s position. What would that be like? A lot of us have either seen people in similar scenarios. We’ve either had to lead a scenario like that. Ourselves has been in a similar situation. It’s not a huge leap to start to imagine being in a situation.

I’ll make a few assumptions. Let’s imagine that you’re in a situation where you feel like you’re holding up a project that’s not going well. Fair to say it is under-resourced. If she’s in this situation, to your point, I don’t think it’s been managed all that well. The fact that we’ve gotten to this place with Sue is an indication to me that this has not been managed very well. It’s a little bit of a pass-the-buck scenario going on. Maybe there are reasons for that but still could have probably been managed better. How does that leave her feeling? It sounds as though she’s working hard and taking on things out of her normal scope of responsibilities.

When things aren’t going well, people know that they’re not going well. We know our brains don’t deal well with uncertainty. We also know we’re also in a time in our world where there’s a lot of uncertainty and it’s layering on for people. That would indicate that she might be working hard and doing her best but she is not necessarily her best. That’s an important distinction to make. Sometimes we’re all outgoing. I’m doing everything I’m being asked to do, everything within my power to do, but I know I’m not bringing my best and being my best.

Add to that… arrives a new person and the feeling of I’m being left out of some of this stuff. I’m being left out of decisions. I’m not involved and that doesn’t feel good for people either. Most people want autonomy. I’m always asking, how can we give people more of what they want? That’s ultimately how they’re going to be able to show up in the best most productive way. If we could give over control and autonomy, let’s try to do that as much as we can.

Thinking of it from her perspective, we could think a bit more about the best approach to take in this situation, what Steve works through, how he’s feeling about it and what’s important to him. It’s this shifted perspective thinking about it. He was able to relate to this and go, “I know what some of that feels like.” What’s the best approach to take? This is where we got into, “When you’re going to be spending time with her? What questions might you ask of her?”

Sometimes you need to say a few things up front and then you need not say some stuff. Explore, ask questions, be open-minded and then maybe say a bit more because we’re building trust as we go. If we say too much in the beginning, it puts people on their heels a bit. It doesn’t build the trust that we need to build in the beginning. Any thoughts on that?

A couple of things. I’m going to pick up when you said that our brains don’t like uncertainty. The other thing that our brains don’t like is feeling threatened, and I think Sue’s feeling threatened here. She’s been working hard. I question the culture of this company, where they would leave someone struggling and languishing in an overburdened role. I would suggest that Steve pay attention to the fact that this company might not have its cultural values aligned with the behaviors of the leadership team. That’s one thing I would clue into him.

Regardless of where you are in an organization, you have the opportunity to be a great boss. I would dialogue with Steve around, “You’re walking into this situation. What do you want to walk out of it with?” Let’s say, he wants a successful project. I’m going to assume that’s the case but maybe there is a learning opportunity for him. If he’s going to work as a consultant, this is going to maybe happen more than once over the course of his working life.

What is it that he wants to learn to do in situations like this that he can carry into other situations? I would have him be very thoughtful about his approach and the intentions that he has. Working with Sue is going to be a relationship. They’ve already met once and he’s got some data on how she’s feeling from his reception. He needs to be open and upfront about saying that to her when they eventually have their first conversation. What is it that he hopes for in terms of her success and not only his success?

WR 20 | Complex Workplace Scenarios

Ask Us Anything (Steve): It’s so important to acknowledge people’s effort even when things don’t go well. If somebody is trying hard with all the tools that they have, it’s important to acknowledge that.


The other thing I would say is that this might be feeling unfair to Sue. I’m making assumptions but maybe she’s been promised things if you get this project going or you’re in for a promotion. Maybe that hasn’t happened because she’s doing this off the corner or the side of her desk. It appears that she’s out of her depth, but maybe the issue is that she hasn’t been resourced or supported. I might be going out on a bit of a limb here but I’m wondering if this scenario also has echoes of, “Let’s bring in the hero to come to rescue a situation that a woman wasn’t able to handle.”

I’m not sure that’s the case but I have seen those dynamics in some of the workplaces that I’ve been in. I’m going to park that as a little bubble amidst this broad landscape. I’m thinking of Steve: it is not easy to step into a situation with a lot of unknowns with high pressure to perform. I would also ask him what his measures of success are, separate from the project being successful and the relationships he builds. What is important to him in this? If this is his first gig as a freelancer, what are some of the measures that he’s going to be measuring his own success on, regardless of how this project goes?

Frankly, it sounds like he’s highly competent. He harnesses some of the relations skills to make it work with Sue. He’s going to need to think about the person he’s becoming as he works with her, as he becomes a freelancer or a consultant. To anyone who’s moving into those kinds of roles, it’s not so much the work you do and the clients you build, but it’s the person that you are and that you’re becoming and building your business. I would suggest that he spend a little bit of time thinking about those things as well.

It’s all part of that building the self-awareness and your EQ that we’ve talked a little bit about in the past, all of that. It’s important to do that self-reflection. Imagine that he’s the meeting with Sue. What do you think is important to say or ask upfront? I have lots of thoughts on things to maybe ask her to help build trust and find out more about where she most wants to contribute on this project. If she could pick any aspect of it that she wants, what would that be? I imagine in my mind, we need to dial down the pressure on this situation. Let’s loosen up that release valve and release the pressure a little bit.

The best way to do that is to come in with a little bit of humility. Acknowledgment of the situation that this must’ve been difficult for you. I can see that you have been doing a lot to manage this situation, perhaps with limited resources and so forth. “That must have been difficult. What’s that been like for you?” Looking for opportunities to bring her into the conversation and reduce any potential defensiveness. Ask some big open-ended questions like, “What’s most important to you in this project?”

As they go, they can have conversations more about even her career. “How does this fit into your career? How can I help you achieve some of these things along the way?” To me, that line of questioning is where you’re going to get a lot more buy-in, trust-building and someone who’s going to say, “I can see how I can make a contribution here and there’s going to be something in it for me but I’m also going to feel how people feel at the end of the day.” That’s what’s going to drive behavior. How are they feeling? Do I feel supported and understood in this situation? Anything you would add to that?

Please forgive me for jumping onto the Ted Lasso bandwagon. I do want to make a little point when it comes to trust-building. It’s early on in the series. I’m not giving anything away to those of you who have yet to binge it. It’s quite worth your time.

Ted’s the coach of a soccer team. He comes in and there is low trust. “Who is this guy? He’s coming in. He doesn’t know us.” He puts out this suggestion box and a lot of it are insults to him, but one person writes that they hate the pressure in the shower. What does he do? He fixes the pressure in the showers. By doing an act that might not seem to have anything to do with workplace culture and building relationships, he has done something.

It showed that he listened and acted. In the same way, I would say to Steve, when Sue was able to share with him what it is she needs to be successful or that she hasn’t been heard or listened to her, whatever she says, he needs to do something tangible to show that he’s listened to her and that he’s acting on what she said. That will go a long way to building a trust relationship. I’m going to get on my little tiny soapbox for one second on this topic of acting on feedback or on what people are saying. This is why the idea of engagement surveys has gone completely sideways.

We ask people what we can do to make them more effective, to help them be productive, creative and innovative. We look at the results and do almost nothing with them. This is why leaders often get a bad rap because they’re not acting on the feedback that they’re getting. By the way, you don’t have to guess. If somebody tells you what they need to be productive and happy, deliver it. That is how you create engagement. That’s how Sue will probably start to see and understand that Steve has her back, and that they can form a good relationship and a good team and they are both going to succeed.

Where I said at the beginning that Steve might want to consider how this will advance his broader goals for his career, I would also suggest a conversation between Steve and Sue about what she needs to advance her career and how working together can support her career development. She tangibly is getting something out of this relationship.

When things aren't going well, people know that they're not going well. Our brains don't deal well with uncertainty. Share on X

You reminded me of this other amazing scene in Ted Lasso and it’s a bit down the road in the season. Hopefully, it’s not too much of a spoiler alert. One of the characters is debating about moving on and telling her mentor. She’s nervous if the person’s going to be upset. One of the other characters says, “A good mentor is going to be thrilled for you.” Wouldn’t that be great? I’ve grown and developed. I’m ready to fly out of the nest. There is a scene where the two of them are on the couch. She’s telling her and they’re crying. It’s so beautiful. I love Ted Lasso.

What’s the cap on this? Preparing great questions to ask her and get her greater autonomy. People want to control: recognize that you also don’t have as much control as you think too. We don’t control other people’s behavior. All we control is how we show up, and go in with clear intentions, but also open and receptive intentions.

Part of that intention is like, “I want this successful project and I want it to be successful for both of us. Ideally, I’d love for us to work together.” One other thing I’ll say is it’s so important to acknowledge people’s effort even when things don’t go well. For example, we would never say to our kids who flat out tried on something like, “It didn’t go well. Here’s your package. Walk out the door.”

Can people fire their kids? There might be some reasons for that but I know what you’re saying.

It’s important to acknowledge effort and improvement, even when things aren’t perfect, didn’t go amazingly well or somebody is out of their depth. If somebody is trying hard with the best tools and capability that they have, it’s important to acknowledge that. Acknowledge it publicly whenever that’s appropriate. That can go a long way with bringing people in instead of pushing them farther away.

WR 20 | Complex Workplace Scenarios

Ask Us Anything (Steve): Whatever your client says, you need to do something tangible to show that you listened. Act on what your client said. That will go a long way to building a trusting relationship.


Organizations are built on roles. There are hierarchies, bosses, employees and a whole bunch of dynamics… many situations. All of them call for us to be connecting human to human. This is an opportunity for Steve to do something important in Sue’s life, and show up as somebody who genuinely wants to connect, help her build her strengths and perhaps her career, if that’s what she wants. More importantly, to bring both of them up and make this a win-win situation. Steve’s got a great opportunity here and I’d be curious to know how it goes once he’s involved.

We don’t know that this is going to work out. You do also have to consider worst-case scenarios and alternatives. Part of the thinking that Steve is going to need to do in the beginning is sometimes we can try. You know that old saying, “You can lead a horse to water.” We can’t control other people at the end of the day.

“I’m going to try this a little bit but if there comes the point at which it’s not working, then other decisions have to be made.” Thinking ahead to worst-case scenario-ing it, not that we want to dwell on that but it’s good to have some alternative strategies and plans in mind as well.

That’s our first Ask Us Anything in the can. Send us your questions. Go to our website at www.WorkRevolutionPodcast.com. You can get in touch with us there and on Facebook.

Regardless of where you are in an organization, you have the opportunity to be a great boss. Share on X

Facebook is at Work Revolution Podcast. Debra and I are both on LinkedIn. Please bring us those gnarly, difficult and challenging situations that you could use a bit of help with. We’d love to be able to offer our two cents.

The idea here is that we don’t always have perfect answers but we’re figuring it out and doing our best. We can all learn from each other and each other’s experiences. That’s what we’re going for. We’re not going for perfection. What we’re going for is how we can hear each other’s situations. By knowing different perspectives, we all learn to move forward in a meaningful way and do our best. Until next time.


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