Boss versus Bully: A Gentle Shift to a New Kind of Leadership

How untangling a combative relationship pushed me to shift from appearances of authority and acts of power to becoming a leader who offers support, acceptance, and space for growth.

“Is she bullying you?” my boss asked. Inside my head, the sound of a record screeching to a halt cut through all the other noise.

My boss and I had been talking about how to handle the behavior of one of my new hires, who was frequently acting out, especially in front of the rest of my team. Her behavior was making it significantly harder to do my job.

She certainly seemed to be attempting something with all her grandstanding, but I wasn’t sure what. Was it actually possible, as he was suggesting, that I, her manager and the team lead, could be getting bullied?

I was newish in my role, tasked with building a business function from scratch for a client organization. The function would encompass several complex, high profile programs that we were there to pilot. I didn’t feel like I had the bandwidth to deal with drama on top of it all.

A Fearful Touchstone

My heart started racing at my boss’s words. I had to look away. His comment seemed uncomfortably close to evidence for the very thing I’d feared since first becoming a manager in my twenties: that I was too nice and therefore weak; a door mat; easily pushed over and trodden upon.

The space between our fears and our strengths is an interesting one.

A friend recently informed me that I get notably more generous to people when I know they’re wrong or uneducated on a topic — particularly if they don’t seem to realize it. Rather than calling them out, I provide information, or if I can’t do that without embarrassing them, I simply let the topic drop. And while my friend said it is one of the things she appreciates about me, it points to something core to my behavior that is probably a strength, but can sometimes be seen as a major vulnerability.

This vulnerability confuses people. Often enough, people who don’t know me see a soft expression, smiles, and kindness, and miscalculate what they mean, acting as if I’m their stooge until the day they wake up and discover I’ve turned them into my supporter. It’s a dance of reluctant respect, one which has landed me leadership roles by the end of many an engagement, even when I didn’t start out there.

Still, some form of initial miscalculation about my backbone has happened enough times that fear of being perceived as weak became one of my little paranoias. The day my boss and I were discussing next steps with my new hire, his comment chilled me.

Crack Down

“Bullied?” I shook my head at my boss incredulously, feeling simultaneously insulted, outraged, ashamed and terrified. “I don’t think so.”

But the seed of doubt had been planted. I left our tet-a-tet fuming. The idea that a new team member might be trying to push me around called upon all the shame I’d ever felt in a society that seems to reward the hard-nosed more than the soft-skilled.

“There are two kinds of people in this world,” a friend’s father told me in high school. “Those who serve and those who get served. You’ve got to decide which kind you’re gonna be.”

He was a lawyer, talking about someone who’d recently returned to our home town with a teaching degree — which he disapproved. While I found his idea abhorrent, and the black and white nature of it naïve, his words had remained emblazoned in my brain for nearly twenty years, and popped to mind as clearly as if he had uttered them yesterday.

Was I the boss? Or was I gonna let myself get bossed around? Would I serve or be served? I had better pick the right answer.

The next morning at our team meeting, my new team member launched into her usual flippant routines, talking back to everything I said, making side jokes to her peers that vaguely seemed to undercut my authority, and questioning every request I made from the group. After I asked for an update on a video project that the team had to deliver at the end of the week, she sighed dramatically.

“This ask just seems really over the top,” she said. “Like, making a video is so much more work than is necessary. Can’t we just make a presentation?” I noticed a couple of heads nodding around the group.

“The head of our client organization asked for a video,” I said, my tone icy. “I don’t think it’s worth fighting over when it’s what she wants.”

“I mean, can we at least come up with our own process to make our own videos? Do we really have to do it the way you showed us?”

“We have just a few days to do this,” I said, taking a slow step towards her without breaking eye contact. “We have to split up the work to get it done,” (step), “and we need it to look like a uniform product in the end.” (step) “So yes, you do have to do it the way the team agreed on the other day.”

By now my teeth were clenched and I was towering over her — all five-feet ten inches of me, plus two-inch heels. My eyes had narrowed, while hers widened. The rest of our team members straightened up.

Good, I thought, now they all know what they’re dealing with.

But little did I know, I’d only lit the fire.

At this point, anyone who has managed people is probably wondering why I hadn’t pulled this person aside to tell her how her behavior was impacting our team meetings and ask her to consider some other ways she might want to show up. But the truth is, I wasn’t comfortable confronting such a volatile person directly.

Why did I fear this? I could point to being inexperienced, but while it was early in my new role, it was far from my first rodeo managing people. It was actually embarrassingly late into that phase of my career to be dealing so poorly with this kind of issue.

But it was the first time I’d encountered someone who so virulently pushed back against my authority. And I rarely felt like an authority anyway. Imposter syndrome ran rampant in my head, sending me down rabbit holes about whether or not I had the right to boss people around. (Thanks, childhood programming re: “don’t be bossy, little girl.”)

And now we come to the crux of it.

I was so busy striving to appear as if I deserved to be the leader, to garner respect and demonstrate authority, that I had more or less overlooked how to lead.

Escalation

That afternoon, this new hire of mine cancelled our weekly 1:1 and was notably absent from our work area. I suspected she was working in a conference room, hiding after our confrontation at the team meeting.

The next day during the team touch-base about our video project, she reported she hadn’t had time to work on her portion. I told her she’d better catch up so we could review team progress the next day. We were getting down to the wire.

Things escalated till Friday. When she finally turned in her work, she’d gone against every storytelling guideline I’d laid out, and her message was still half baked. She hadn’t used the standard designs the team had agreed on to create a cohesive product. When we got to her section of the video, it looked, sounded, and felt different—and worse, it didn’t complete our story.

I was furious. We were meant to present the work to my boss on Monday and to the whole organization on Tuesday. She’d have to work over the weekend to fix it, and if she still came in Monday with nothing useable, we’d be out of time.

I told her to work with me over the weekend, trying to ensure that I could provide real-time feedback, but she couldn’t be available any of the times I suggested, citing a visit from family. And the first draft she sent me asynchronously was so off the mark that in the end, I made my own version of her video as a back up plan (taking almost all of my Saturday to do it), while hoping she still came up with something good.

When she returned Monday, she’d made barely any changes. I swapped her video out for mine with little more than a growl. She grew sulky, muttering audibly for all to hear about how much work she’d put in, and now it was all getting wasted.

Looking back, was this swap the right choice? This was clearly a pivotal moment for our relationship, one which would set the tone going forward and determine whether or not we’d be able to do great work together or not.

And yet there were hundreds people in our client organization about to watch a video explaining what our team was there for. Not one of those people would know who on my team had created the coherent portions versus the incoherent ones—they saw us as a unified group. We’d be lucky if any of them would trust us after viewing a story that didn’t fit together.

After seeing how positively our final video was received, I decided that enforcing standardization was the right choice for positioning our team overall. But the message I sent to my team members by swapping my video in for my new hire’s was not a good one. The idea that if you did shoddy work I’d swoop in to save you at the last moment set a bad precedent. As did the implication that I didn’t care to coach anyone to improve—I’d rather just do the work myself.

Furthermore, it only widened the growing gap between me and her.

In the team retro meeting, when we assessed what went well and what we could do better next time, we spent a good chunk of time critiquing our overall video making process. It had been cumbersome and laborious. None of us was good at it, particularly given the time crunch we found ourselves in due to the last minute ask from the client.

My new hire was glad to get a chance to air out her grievances about the process, and I was perfectly happy to take her suggested improvements seriously, since none of us wanted to repeat what we’d just done. Meanwhile, I also had the chance to raise questions about how we worked a team.

Most important to me was rebuilding team cohesion and giving everyone a sense that this wasn’t our final day in the sun. While it was unlikely we’d have to make any further promotional videos in the near future, it was obvious we’d have to act as a unit to produce shared output of other kinds. And we needed to be able to learn and grow from our experience.

Additionally, during my next weekly 1:1 with this new hire, I (nervously) raised the idea that in situations like this one, it would be better if she could be more of a team player. She didn’t say much to that.

Thank god, I thought, maybe we can be done with this. I suspected that when she saw the reception of our video by such a huge audience, it dawned on her why it mattered that we make it so polished.

But the sour note the production process left on our team hadn’t been fixed, and my relationship with this new hire was still contentious.

My Mean Mommie Phase

My team meetings continued to be challenging thanks to her disruptive behavior, and it felt as if relationships with other team members were starting to slide too, particularly as I was getting more demanding, curt, and pushy with each passing day.

“Nice Marisol” was long gone, replaced by a leader who most closely resembled my own bad bosses from times past: the ones who humiliated people in public by talking down to them in shaming ways, who rolled their eyes at team member suggestions and ideas, and who curtailed conversations that meandered or touched on personal topics. “Work first!” and “take things seriously,” started to be my messaging, while my new hire pushed for “goofing around,” and jokes that made me feel called out for poor management. I was suddenly “Mean Mommie” to my team.

For a while it felt like we were stuck, locked in a struggle for power.

Then, after several months, I started to get some tough feedback about my no-longer-new hire from people across our client organization.

Up until then, some part of me had been willing to let her behavior slide because she was so highly qualified and capable. If she did great work, surely I should just shut up and put up, right? But where bad behavior exists with one, it tends to exist with all.

She was meant to be creating a pilot program that spanned many parts of the client organization. If it worked, it would result in a scalable new business for them. Unfortunately, she kept going off and doing her own thing without getting any feedback from me first. The harder I pushed her to share more about what she was doing, the less she seemed to want to comply.

Now, her stakeholders were unhappy with her unorthodox activities, and I didn’t even know what all of them were. I couldn’t rush to her defense, nor could I easily unpack which elements of the outside criticism were real and which were born out of other issues, like fear of change among stakeholders.

I began to worry she simply wasn’t the right person for the job. It was time to solve this problem permanently. Her bad behavior had been sliding long enough.

The version of me from a few months prior—the controlling, insecure people manager who had pushed through the awful video-making process with a power play—might have continued to crack down on her, thinking “it’s my way or the high way,” and deciding she could shape up or get out, thereby proving that I wasn’t a too-nice push over after all.

But I’d been on my own growth path in the months since she’d joined my team. And by this point, I was ready to dig deep.

My Own Leadership Growth

During this time, I’d been doing a lot of my own personal work on what it meant to be a people leader. Even though it wasn’t my first time managing people, I knew I needed to change something. I’d been so activated by my new hire’s behavior and the way she challenged my authority that it was clear I had my own missing link to contend with.

I started off very tactically. I read a book called How to Delegate from the Essential Managers collection: a slim, tiny volume about the process and benefits of delegating. It proved useful for ensuring I set up projects the right way, providing clear expectations for various outcomes and developing checkpoints for review, rather than outlining explicit instructions and faulting people for not following them to a tee. But it didn’t solve my problem with managing this contentious person.

I refreshed myself on a book I’d read early in my management career called Radical Candor, which had proven essential when I started out, teaching me to set up weekly 1:1s with each team member and how to provide feedback. Still, the frameworks for feedback in the book didn’t give me insight into how to cultivate a good working relationship with someone so fundamentally opposed to my leadership, along the way to reforming her behavior.

I read The Leadership Pipeline, which explains how we must transition through different phases of leadership as we move from being first line managers, to managers of managers, to functional area leaders, to divisional leaders, and on to organizational leaders, e.g. CEO’s. I saw where I was on that leadership growth path and what sorts of skills I should be focused on developing.

It was increasingly clear that leadership is a people-first endeavor, and my purpose as a leader was to bring forth the best in others. Of course, this was obvious from the outside, but it took a deliberate internal shift on my part to begin to act on this belief. I realized that if I continued to bring an impersonal approach, managing through tactics and authority alone, I wouldn’t be able to motivate others in a sustainable way.

This realization only further convinced me I needed to improve my leadership skills.

I raced through the book, From Supervisor to Super Leader, putting aside any embarrassment I had about being such an experienced team manager reading such a seemingly remedial book. I appreciated how directly the author, Shanda Miller, lands her point that leading is not the same as managing. And her brief but clear chapter about building relationships with team members said things like “get to know your team members” and “ask them their aspirations” and “learn about their life story.” She also advised that each day a leader “greet each person by name” and ask how they’re doing.

Seeds were getting planted, if small ones. My 1:1s started to include more personal questions and chit-chat. My long time team members easily fell into conversation with me and our relationships blossomed. But it was awkward to ask my angsty new hire about her life. Still, despite her initially tight-lipped responses, this new practice eventually started to warm things up.

I then began taking a coaching approach to performance improvement with my team members. It was going well with most of them, and they were growing more self-directed in their pursuit of excellence. I asked them to craft plans and set their own expectations for work products, ask questions as needed, and then review their plans with me to see if we were on the same page. If not, we worked out how to align so that we delivered what the client organization and their customers needed.

My team members were the ones now driving their own project plans, expectations, and work review conversations, assessing whether their output measured up to the initial goals they’d set out to achieve and seeking my advice and support in closing the gaps when needed. They began to identify their own desired skills development and we talked more about their future career paths.

But coaching still wasn’t going so great with this one new hire. Despite some level of congeniality growing in our relationship, she still didn’t seem to trust me past telling me about her weekend plans. That make it harder to figure out how to shift into the coach role.

Instead of warming up to the idea of setting her own expectations and reviewing them with me, she seemed to see my interest in that behavior as further evidence that I wasn’t qualified to lead her. Instead of happily offering up critiques of her own work, she wanted to hide mistakes and errors and was unwilling to hear a word of what I had to offer. She seemed to be asking "What are you even here for, anyway? I don’t need you.”

By the time the hard feedback about her work came through my inbox, I was exhausted from all the struggling I’d done with her. But I had to deal with it one way or another. This was no longer between me and her. It had impacted multiple people across the client organization.

How would I use my burgeoning people-first approach to coach her through this moment? I knew that excellence did matter to her, even if we sometimes differed about how to achieve it. I knew she was smart and talented, if sometimes stubborn and forceful. These were things I could use, but how?

And even more nerve-wracking for me was how I would find the stomach to tell her things weren’t going well with her stakeholders, when it might elicit even more confrontation in a relationship I’d worked so hard to improve.

My Gentle Shift

As I’ve written in the past, Gentle Shifts are humane changes made in your life that help you develop new skills, attitudes, actions or reactions, but in the most self-honoring, patient way. They don’t force change. They don’t power through, ignoring problems and emotions.

Gentle Shifts are born of a desire for change, but come about through quiet reflection, self exploration, trying new things, allowing for failures, and finally, releasing the old to peacefully step into the new.

My dating life had been undergoing significant transformation around this time due to a pair of books I’d read that changed my perspective on the process from one of “finding the right person” to one of “showing up as myself and allowing what happened to happen.”

It was a subtle shift in outlook, driven by a book called If the Buddha Dated. The introduction states, “This book is about creating love in your life. It begins with bringing awareness, compassion, and loving kindness to yourself, including the parts you tend to disown or want to keep hidden. This journey of self-knowledge may be uncomfortable, sometimes challenging, but it will help you make friends with all of who you are, so you will be free to welcome another person into your heart.”

I read it nearly simultaneously to reading 90 Seconds to a Life You Love: How to Master Your Difficult Feelings to Cultivate Lasting Confidence, Resilience and Authenticity, which teaches how to ride through hard feelings. Because learning to manage emotions came into my life alongside a mindset shift about “making friends with all of who I was,” I started being more accepting of my own difficult, less than pleasant feelings. It was a massive leap forward for me.

All of a sudden I started to ask myself new questions: “What if I brought this same approach to my role at work as a leader? What if I could be more accepting of my own challenges and those of others? What if I could simply show up as myself and allow what happened to happen? Would it improve things or would my team’s performance fall apart?”

It was my moment to make a Gentle Shift.

I slowed down to think through how to handle the fresh new challenge in my relationship with my hardest team member. As I did, I found myself aware of a swirl of emotions: fear that made my stomach roil, anger that made my head hot, determination that clenched my jaw and tightened my shoulders, and an out of control vulnerability that felt like free fall.

Noticing these feelings without reacting to them let me move beyond my initial belief that I “must give feedback,” the very thing causing such an emotional reaction in my body. That freed me up from fixation on the act of “critiquing to improve,” so I could explore additional possibilities.

Once I let go of the “feedback requirement,” as a manager who had received complaints about an employee, I saw a different path. Perhaps this wasn’t about me critiquing her, or about sharing the hard things that had been said in an effort to get her to step up. Instead, what if it could be about opening a door for her to become more self aware and self accepting — in similar ways to how I had recently done for myself.

From a place of self acceptance, she would not need to be reactive either. From a place of self acceptance, she might have a chance to lovingly looking at herself as she was right then and there, and wrap her arms around her imperfections while also considering options for how to be in the future.

I decided to show up completely free from agenda in our next 1:1 and simply have a conversation. To show up as I was, to create space for her to show up as she was, and to let what happened happen.

I wanted to find out what was there when I didn’t try to prove anything. When I was not the authority but rather created a safe space for reflection. I took my own ego out of the equation.

In our next 1:1, I started with the simple question: “How are things going?”

She rambled about her personal life for a while, and this time I listened differently from how I had before. I realized that hidden in her semi-impersonal overview of her weekend were hints that there was some chaotic stuff happening with a relative’s health and her home renovation.

“It sounds like things are stressful at home,” I said.

“Yeah, I guess so,” she admitted. We sat in silence for a moment.

“How are you feeling about everything?” I asked. She blinked. More silence. But then she bit her lip.

“It’s a lot,” she said. “Everything is a lot right now. I’m pretty tired.”

“That’s understandable,” I replied, starting to piece things together with the feedback I’d gotten about her work lately. “How is it impacting you in all you’re doing?”

She shrugged, her face pensive.

“What about at work?” I asked. “I don’t know the full scope of it right now, but I know you’re interacting with a lot of teams and stakeholders. That sounds like a lot too.”

She nodded, swallowing. She took a deep breath. I could see on her face that she was struggling with some kind of emotion. Finally, she spoke.

“I kind of feel like people are expecting things from me that I shouldn’t be asked to deliver,” she said. “There’s so many stakeholders. I can’t be all things to all people, but so many of them seem to think I have a full time job just working on their part of my program. But there’s like fifty people expecting that from me.”

“Your program is really massive,” I affirmed. “But I am here to support you when you need it. You can ask me to go to bat for you, I want you to know that. If it helps, I can tell stakeholders how much of your time they can and can’t expect to get.”

I felt myself make a shift right then. I became her defender. We were on the same team. Her success was my success. And if her new program worked, it would be a success for the client organization too. My role was to give her everything she needed to succeed.

I’d technically known this was my job, but in that moment, it became the job I had in my heart. She must have felt the shift and the power behind my words.

She began to open up about her challenges, and we talked through as many as we had time for in the remainder of her 1:1. It opened the door for me to say, gently and non-judgmentally, that I’d received comments about her project that suggested people wanted some things to change. And I reiterated that I was here to help her.

I affirmed that she was the only person who could know what to do with the feedback from stakeholders because I hadn’t been there. As we talked through her version of what had happened, I asked questions about what might be true for stakeholders, and what might be possible for the project going forward.

One of the reasons I had been given the specific role I held—developing a new functional area that was potentially contentious within our client organization—was because I had become known as a person who could get group decisions made and find solutions when other people seemed to remain blocked.

Part of my method was to listen between the lines in meetings and then address the unspoken conflict in the room. I could identify when the representatives of multiple teams and projects were afraid to speak directly to each other, and then figure out what they actually wanted to happen. Then I would lay out the multiple viewpoints and cut the tension, having removed the fear and emotion out of the conversation, leaving only facts and practical options.

That skill is what I offered up to her as we talked through the situations with each of her stakeholders. We practiced empathizing with each of them in order to assess what it was they needed and wanted. As she gained new ideas to move her work forward, I could tell she was starting to see the value in what I had to offer. She warmed to the exercise. By the time we had our next 1:1, she was almost eager to bring up new challenges to discuss and process together.

Our relationship had begun to transform.

Happily, it only continued to improve over time. As we practiced a more self-accepting, empathic approach to the mess of doing complicated, complex work in a politicized organization, her demeanor shifted.

Soon, when I checked back in with her stakeholders, I was hearing good reports about changes she was making and ways she’d seemingly intuited what they needed.

As I kept evolving my approach to team leadership, she even became an enthusiastic participant in the exercises and activities I had our group begin to do in service of our collective personal and professional development.

Lessons from this Big but Gentle Shift

In making space for my own Gentle Shift, I figured out how to create space for my team member to undergo her own. In doing so, I learned the difference between managing for performance improvement versus leading for human development. And I got my own ego out of the way.

We were no longer boss and bully locked together in a power struggle. We were two humans holding space for each other’s growth. As the leader of the team, it was my shift to make first. Once I did, everything changed.

I saw then that though I’d been taught a manager should “give the hard feedback” when someone wasn’t performing up to snuff, it wasn’t my only option. It turns out, rigid performance improvement is not the only way — nor the best way— to help someone grow and develop.

Performance improvement style management is concerned with hitting targets and KPIs through a tactical series of checklists, outputs, and skill building activities. It is primarily concerned with meeting business outcomes, and often leans on strengths assessments and personality tests to know who can achieve what, and who can’t. Poor performance elicits “hard feedback” during reviews, which in turn are times to provide yet more checklists of skills to polish. The individual is measured, evaluated, graded and chastised until they measure up to a set of criteria.

An improved version of this approach is the coaching model of performance improvement, in which work improvement and career growth is still the goal, but it’s less purely about constructive criticism and feedback, and more about self-directed learning, accessed through a question and answer style conversation, alongside clear expectations.

But it’s possible to shift to an entirely different model: leading for human development. To do so requires taking a step back from measuring against work output and KPIs, and seeing a person holistically instead. You can view them as a complete human being with a life, real needs, real fears and vulnerabilities, and vast potential.

When we consider what a whole person needs in order to be at their best as they go through life—including at work—we can ground ourselves in the process of true human development. And we all benefit from learning these skills.

Self acceptance and acceptance of others, gentle shifts, resonant connections, time for rest and play, space for reflection, being present, and holding room for growth are the building blocks of this type of leadership.

The human development approach lets us grow and develop far beyond a given role at work and far beyond success on a specific project. It opens us up to a life lived more authentically, more humanely, and more joyfully. It presents a door to access our full potential, which in turn leads to excellence, wholeness, and great leaps forward.

May you each enjoy the shift,

-Marisol