Career Heartbreak; The Heartbreak No One Talks About

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Career Heartbreak… (sign)… I have two stories I’m going to share today. One that I witnessed from an insider perspective, not as an active participant, but within the Human Resources department. The second story completely altered my perspective on working relationships. Both have a similar theme… Career heartbreak and supporting those in positions of less power to help elevate them. I’ll start with the one less personal, and we’ll get to the personal story in a bit.

I worked with an executive leader (we’ll call her Fiona) that would speak a lot of empowering women, but her words didn’t always line up with her actions.

Fiona had a great resume and some past work that she wanted to share, so she invited the whole office to a presentation after work hours. The project was a bit of a meta or ironic topic, taking adult content that has typically been male centric and mostly derogatory towards women to change the approach to a more feminist or gender respecting angle. To put it bluntly, she didn’t like what the pornography world has done to women and genuine real intimacy overall and she wanted to change that.

As a modern woman, I think what she’s done here is just remarkable and so cool, but as an HR professional, the job is to help prevent any potential liability to the company. We were trusting Fiona to know this line as an executive leader. She was a newer employee but seemed to carry herself with a very strong and independent spirit so making assumptions beforehand to provide counsel on what she should/should not do didn’t seem fitting.

Without any prior notice to HR or leadership, Fiona sent out an email to the office in advance of her presentation to provide additional content. That included a url link to her website, and upon clicking it, there’s a full view of videos including people having full-on sex. In her perspective, it wasn’t pornography. From the literal definition of pornography and an HR and company perspective, it was. Fiona disagreed. I want to be clear about that.

There are so many angles we can approach and delve into, but rather than dissecting the right and wrong of the situation, I’ll allow you, the viewer/listener, to form your own opinions. The avenue I want to explore today is what happened to the HR professional that put a stop to the presentation and how Fiona handled that relationship and others after the controversial email was sent. There was one HR professional that stepped in to confront Fiona, and we’ll call her Suzanne. Suzanne didn’t report directly into Fiona, but she was there to support Fiona as one leader in the company. Fiona was a few levels in seniority above Suzanne.

Fiona remained upset and there seemed to be a disconnect for the dichotomy of an HR professional having to step-in to help prevent any further risk to the company while still respecting the work she was doing ‘outside of work’. Fiona really wanted to share the disruptive work with her team that in-part elevated her to the level of success she had obtained. 

Side note: Fiona was not discharged from her position and the company was supportive of this work outside of the office. Suzanne defended Fiona’s position in the company and protected her role. Not many companies would be this supportive and open. I want to be clear about this. I don’t want to be contributing to people drawing new lines in different office environments that could get them terminated. This is a unique situation, in a unique office environment. 

After Fiona’s presentation was cancelled, a vast majority of the office was quite upset that Suzanne had interjected. Fiona’s decision forward was to plant her feet into her frustration. Suzanne’s position on the matter was supported by the upper-levels of the company but was met with much scrutiny among a good number of the employees. Fiona’s decision to stand by her frustration was felt among the office, and she received a following of supporters. This meant that anyone that supported Fiona opposed Suzanne, and Suzanne later confided in me that a good portion of the office started to treat her differently, ignoring her and not looking her in the eyes when they passed in the halls. I could see that this situation caused substantial heartbreak for Suzanne. She resigned a couple months later. 

Employees kept departing, and Fiona would say negative things about employees in small groups, but at company meetings, she would seem to be publicly bothered by their departures or praise those same employees. A culture of fear ensued and some employees started to share that they felt she was eliminating employees one by one that didn’t align with her vision or opinions, or anyone that questioned hers. Between this treatment and less business coming in, employee retention declined significantly. 

Although the retention problems weren’t specific to any gender per se, there was an exceptional amount of female leaders at the middle-management level in comparison to other similar companies, and after one year of Fiona’s employment, most of these middle-managers had turned over, not been replaced after departing, or were replaced with a males….which is fine on an individual case by case, but that wonderful balanced gender ratio of middle-management declined over time and was off-kilter.

One thing I will reluctantly note, which some may view to be in contrast to the point I’m trying to make, it felt as if the organization allowed Fiona to get away with more than her male colleagues at or near her level of seniority because they so desperately wanted more female leaders. The initial intention was in the right place for sure, but the data was reflecting that things weren’t working out well with Fiona.

The organization at one point had a good amount of women middle-managers, but there was backlash from employees because there weren’t many women beyond that at the executive level, and this industry doesn’t have many women at the top in general. So, hiring one with a great resume (and this woman did have a great resume) was so hard to find and retain. This provided Fiona a lot of power and leverage, and this was unequivocally backed-up by the incident with Suzanne which happened so early in Fiona’s employment.

So, why did I outline all of this? Well, I want to express that:

  1. When we are in positions of power where we can elevate or harm others, we choose the former. Whomever is holding the power had enough go right to be in that position. It’s never worth winning at the cost of other good-willed people around us losing so much more. Share that power, even when it’s hard.

  2. We don’t want to keep the wrong person in a role because they fit another need. It’s much more important to have someone in a leadership position that empowers their team vs having someone that’s not right for the position but fills a much needed, likely overly delayed, demographic. 

Ok, now to my personal story. I worked for a small company a while ago. When I started at this company, it was very small and it was not doing well. I was hired to (1) backfill for essential roles (2) expand the company size and (3) build out an HR function and eventually a team. There was only one other woman at the company when I started. She worked there a few years prior to my employment and held a smattering of different roles at the company, all as a problem solver (being vague purposefully to protect her identity). She was very welcoming when I joined and we quickly became close friends. Let’s call her Rebecca.

One of the many things I did when I started my position was that I conducted an audit of compensation bands, titles, and internal equity. I immediately noticed that Rebecca wasn’t being fully valued for her contribution to the company, both in title and compensation. We shared the same mutual boss, so I confronted him about this. I was immediately rebuffed. Her role was painted into one box, and I didn’t think that was completely accurate.

Rebecca and I continued to work closely, and I learned that she was the employee that wouldn’t say no to anyone who asked for help, and although her job was to support only one department, she ended up juggling a bunch of items. She had no problem doing the neglected tasks that needed to get done.

After working together for a few months, we would catch ourselves in meetings at 4:00pm that would evolve into post-workday banter and gal-chat. It was nice. I made a friend. This happened often enough that my partner would come home from work and just know that I was chatting with Rebecca while cooking or ordering dinner.

I continued to have conversations with our mutual boss about level-setting her, many times, and every-time, he would tell me that he felt her title and job responsibilities were in-line with what she was currently doing. I disagreed with examples every time. She did get a small pay-bump after a few months, but it didn’t seem sufficient. Her and I also had a difficult time cultivating a job title for her that fit into our organization size and structure and aligned with her job responsibilities, since her job consisted of pieces of other positions.

Rebecca would check in with me and ask me how the conversations were going with our boss. She expressed that she could never ask for a raise or a promotion. I spent a lot of time coaching her and working to build up her confidence. Rebecca was unaware that I was being shot-down by our boss. I kept it as a “work in progress” and I wasn’t going to give up. Our boss would also express frustrations that she wouldn’t come to him to ask. I finally realized it was truly time for Rebecca to ask for the promotion herself. I told her that it was time and she agreed.

After eight months of coaching her, Rebecca finally asked for a promotion. Our boss didn’t make any immediate decisions. He initially came back to me and said he was open but reluctant. We didn’t speak about it for a few weeks as he traveled, so the topic was on-pause from my perspective.

Upon my boss’ return, we’re catching up and he informs me that he’s come to a decision and wants to promote Rebecca…. Wow! We did it! Amazing news…. He then proceeds to tell me she’s being promoted to a chief level… Bah wha??? I was baffled! Completely shocked is an understatement… He resisted anything for eight months, then she’s promoted from the very bottom level of the org to the very top? It made absolutely no sense. I questioned his decision, and he outlined that my arguments had resonated and after speaking to her about it, it felt right to him as a rectifying of all her past work in keeping the company together. There was only a small percentage of employees left from the prior batch and she hung in through some rough times. 


At this time, I was on the promotion track towards VP, a conversation my boss had started and came to me about, and I was promised that if I met certain goals, my promotion was to come in a couple months. 


To shamefully admit, I felt that Rebecca’s substantial promotion devalued the promotion I was still earning. I thought very highly of her as an employee and a friend, but her resume prior to or at this company didn’t warrant this jump, and she had no executive leadership experience. She was skipping Lead, Manager, Senior Manager, Director and VP. In Silicon Valley, we have young or inexperienced CxO’s. They’re usually visionaries, creators, and high level strategists. Rebecca had all these capabilities in her toolbox to reach this level of success and to develop these skills. Without venturing on her own with a great idea and starting a company from the ground up, it seemed odd for her to not climb that ladder, step by step developing all those skills. 


The biggest point of concern is that Rebecca’s compensation only slightly increased from the prior small bump, so this promotion was in title and responsibility only. As a woman, and an HR leader, my radar was going off left-and-right. If the promotion was truly earned, then it should have come with all it entailed. The title, the responsibilities, and the compensation. The comp gap was still very significant for a c-suite role. If the position was lacking this much in one area, was it viewed as earned or gifted? Are we valuing being in the trenches together for a couple years prior this much (or this little)? Shouldn’t we be able to give Rebecca the promotion and pay she deserved, whether that’s at the c-level or at a lower level? If we leveled her to a position just under the executive branch, the compensation made more sense and her position and responsibilities would ultimately remain the same. If I speak up to my manager, will he even listen, or am I the pre-VP promotion employee that got jumped over many levels by my friend and close colleague? He also informed Rebecca of her promotion before speaking to me (the head of HR) first. That made it hard to course correct. I decided to move on as there was no way to put this genie back in the bottle. 

I’ve always thought that we know who our true friends are when we’re tested by being on the bad end of growing apart. I reflected on this and asked myself if I was being a bad friend for feeling that the promotion seemed unfitting, and for questioning her recent success. I came out of that reflection with a resounding no. When I removed the feelings of friendship, and took a step back, I felt we were robbing Rebecca of the right to grow in her role and in her career. The decision had been made and was out of my hands though. I trusted my boss too, so I congratulated her and provided my support. I now had a friend on the inside of the executive team that valued my friendship and input, and that partnership had value.

Unfortunately, I don’t think my perspective was felt on her side and our friendship and working relationship started to deteriorate once she was promoted. The ink hadn’t even dried on the paperwork, and she was unfriending me on facebook, because she was now an executive, and that wasn’t fitting in her eyes. I thought those things were silly, but I knew she was trying to find her footing in very foreign terrain. Unfortunately though, that elevation that I had helped Rebecca gain, well, that pendulum didn’t swing back my way. The person who had a hard time saying no to helping was putting up blocks and walls everywhere, and she was no longer willing to even partner with me.

Going back to one of my major responsibilities, to grow the company… I did that in spades. I hired a badass team of professionals, and actually exceeded the goals and targets my boss set for me. Because Rebecca’s job consisted of so many different pieces of the company, as we hired professionals to manage finance, design, business-development, payroll etc, those pieces of her job started to get passed off. The timing was odd, because as I decided to focus on scaling the company and meeting my goals, she was promoted and looking for areas to shine in her new role.

Prior to my arrival, Rebecca held all the keys to the HR department and it was the easiest for her to hold onto with all that was shifting elsewhere. She had a tenure of a couple years on me at the company, and her job allowed her to develop closer relationships with executives than mine did, especially once she joined the executive team. At most attempts to gain support in running my department without her oversight, I was met with friction.

To provide examples, HR sent out an employee satisfaction survey and she felt that should come from her function instead. After HR sent it, she insisted on access to the survey results. Another time, I suggested we create a payroll email alias with HR, and a few other departments that get similar questions as HR handles some aspects that tie into payroll (taxes associated with immigration status and changing exemptions blah blah…). We didn’t have a ticketing system and I felt collaboration and documentation was the best route as time was wasted, the employee experience lacked bouncing people everywhere, and the same questions were being asked repeatedly. Rebecca expressed that we didn’t need another email alias, provided no other solutions, and received executive support in not providing any solution to fix this recurring problem. 

I also couldn’t use the word “culture” in any context without her feeling it was owned by her and her team. I would explain that culture is owned by all employees, but a lot of the initiatives for it are driven by HR. Culture was always a point of contention. 


It seemed as though anytime I had a suggestion for improvement, recommendations for better collaboration or a concept for how to run my department, she resisted, put up walls between the executives and me, and refuted my ideas. She would often resist ideas from my team and me, then present them to the other executives as her own. I think this really came from skipping so many steps and not developing those skills. I witnessed employees that resisted her taking their ideas being on the outs with the organization, and the ones that succumbed were rewarded with her friendship and were in good standing. Rebecca had a lot of clout, and now power. 

Rebecca held the admin level accounts for emails, the cap-table / share vesting, slack etc. When I would ask for access to implement this data into new tools so employees could access their own info, she refused. Rebecca had all this access prior to my employment, and she had the executive support to keep those keys. In every organization, the head of HR should have access to all employee communication channels, and/or no one employee outside of HR should hold these keys. I was locked out, and she wasn’t letting me in. Not even to share.

Even after exceeding all my goals, starting the foundations of a badass team of my own, setting my own goals and exceeding those, all under the pressure of having walls put up left-and-right, my boss started to avoid the topic of my promotion when the time came. I tried to gain insights from him as to why. He was stoic and wouldn’t open up, but held the promotion back. I was informed of my upcoming promotion one month before Rebecca received hers, but hers fundamentally changed the structure of the org to where it affected mine. I waited five months before asking about the promotion. I gave it three more months before realizing it was never happening.

After coming to this realization and knowing I wasn’t going to effectively be able to do the job I currently held (which would affect my internal brand as a SME), I left the company. The day after I gave my notice, they gave Rebecca the HR department. I didn’t have another job lined up and I was heart-broken. Even though I needed to leave, like a bad relationship, I wanted them to ask me to stay. I have since moved on from this heart-break, and learned a lot from it. No exaggeration though… This was heart-break. 

Was I perfect? No. Was I a little jealous of her promotion? Of course. Did I let that affect my quality of work? I truly believe I did not. Did I do a damn good job under intense circumstances? Yes. So yeah, this hurt.

Why am I sharing this story, especially when it didn’t end very well for me? Well, I think the biggest take-away is that we can’t let one major heart-break define us. There are so many movies, shows, plays, books, poems, and songs written about romantic heart-break, but career heart-break isn’t talked about very much. We spend our 20’s so excited to build a career, and somewhere in our 30’s or 40’s, something happens to a lot of us that surprises and alters us. 

Climbing each step gives us the tools to handle each rung, and I truly believe Rebecca had all the abilities to generate power without looking for it elsewhere, but she just didn’t realize that yet. My perception is that Rebecca likely had some imposter syndrome (as we all do from time to time). I do have empathy for how hard that must have been for her to navigate. 

This happened a while ago, so I’ve had a lot of time to reflect on this. If I had to do it over again knowing what I know now, I would have gotten less emotionally invested, but would have done things the same. People are complex and I know Rebecca didn’t intend on doing me wrong. Even though this changed my perspective on work relationships forever, I believe I did everything I could to elevate a great female employee at a time when I had the power to do so, and I guess you can say I did my job exceedingly well that time.

Both these stories have a woman that’s in a position of power, and another woman that was fundamentally doing her (or my) job but voluntarily quit due to a lack of power and support. A point of collaboration or a common ground wasn’t found in either case. Although no one involved was helpless, there are times when people have more power than others and make active choices how to handle the power they’ve been bestowed. As women, there are less of us at the top and we need to leave the ladder after we climb it. The 50th floor is much nicer with company.  

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