Unraveling Complex Human Dynamics at Work
A Real Deal Connection Exercise for the Emotionally Mature
Late last year I was inspired to write about leadership from the perspective of a millennial. In my line of work, I get a lot of questions about how to integrate generations successfully in the workplace. So I started a journal entry one night that I assumed would stay trapped in my phone until Apple makes it impossible to use an 8 Plus. But I kept coming back to the entry wondering if my experience was relatable, and dare I say it, perhaps valuable to someone else. However, every time I re-read it I was terrified to share it. I had written a story about leading someone who was older than me and I wondered if my perspective would offend her. I didn’t feel confident that my story appropriately evaluated the complexity of the situation.
So after 5 months, I finally reached out to my former colleague and asked her if she’d be willing to join me in an experiment. I told her I had written an honest reflection about my experience as her manager, but I thought it needed balance. It needed her point of view. She tentatively agreed. We decided that she would write a separate piece and then like Miranda and Steve on the Brooklyn Bridge, we’d set a date to meet and vulnerably share our stories. So we did it! And it wasn’t what either of us expected.
We anticipated our two separate stories would perfectly weave together. We had hoped we could create a small case study with three clear takeaways on millennials in leadership. But, like most valuable human experiences, it was too messy to minimize. We quickly learned that the exercise itself was much more powerful than the bullet points we wanted to craft. After reading each piece, we noticed that the writing was for us, not an audience. However, the idea of an audience gave us a reason to do it. What the hell, we said, maybe it will give others a reason to try it as well!
What we learned from this exercise: If you are trying to work more effectively with someone who is different from you, the most valuable thing you can do is try to understand each other. You may realize that the only real differences that exist are the beliefs we each bury. The stories we tell ourselves are powerful. Every time you let them run on repeat in your head, the disconnect widens. The bridge you will need to build to come back together will be that much longer. So stop. It’s time to tell your story.
Below are the two essays we wrote separately with limited structure or expectations set. If you are interested, read them as examples. At the end, we will provide some structure on how to conduct this exercise.
Barbara’s Essay (The POV of the millennial manager)
I looked across the table at a friendly and familiar face. I was staring at a person that I had spent at least 8,000 hours working alongside, yet I had not connected with her in over 8 months. We’d worked as peers, I became her manager, I became her friend, I was once her daughter’s babysitter, she was once my armchair psychologist… we knew each other, as well as you can know most people. After just 1.5 years of working apart, she was new to me and I was changed to her.
We spent a few hours catching up about loss, love, growth, work and how to act like a cohesive group instead of several independent units of one. Our conversations were always substantive. It felt comfortable and welcomed. However, on at least three occasions, I felt myself wanting to apologize. As I listened to my friend’s struggles and joys over the last 1.5 years, I was reminded of all the things I did wrong as her “manager.” I found myself wanting to say, “I could have been better. I wish I would have been better. But thanks for loving me anyways.”
My friend, Dee, is 15ish years older than me. When I was hired in 2012 at 27 years old, she taught me “the corporate way” and we often worked as peers and buddies. She was the kind of friend that could automatically tell when I was hungover and trying to hide it. My friend was the person who was willing to listen to the 30 minute version of one of my failed flirtation stories. She was a good friend. In 2014, I became her boss. She was the first person I had ever managed outside of the restaurant world and it wasn’t an easy transition for me. I was so anxious about how she would feel and perceive me. Would she think I didn’t deserve such a role? Would she feel awkward around me? Could I actually motivate her and help her flourish? Could I play any new and meaningful role in her life? I was scared. She, of course, dealt with the entire thing with patience and grace. I am confident that’s not what she was feeling inside, but typical of my friend, she didn’t show it.
However, there was one day that I will never forget. I was on my friend about not keeping up with some data collection and reporting. I realized a mistake in our work, which was technically her responsibility, but ultimately mine, and I really got angry with her. I was asking her questions about her methodology and telling her why this mistake was so serious. The conversation got heated. At the height of the dialogue, she slammed her hand down on the table and scorned me while looking intensely into my eyes, “I am 42 years old and you won’t speak to me like that!” In that moment, her feelings were revealed and so were my insecurities. I was so scared about the mistake, my appearance, and my job that I pulled away from viewing my friend as a human being. I let my fear take over. My fear manifested itself in the form of both blame and control.
I remember thinking about this experience for years and questioning my communication style, but ultimately concluding that it was a big mistake that my friend had made, not mine. In my mind, from that day on, I’d always have to double check her work. This was my mindset as her manager for the next few years. I struggled to trust her. Instead of acknowledging my fear, I micromanaged. While we remained close on a personal-level, I didn’t show up as my best self as her colleague.
As I look at her today, November 1, 2018, I feel my faults. Instinctually, I cared so much for my friend as a person. I always wanted to fuel her life with love and build her up, but I let my own desire to be perceived as effective and successful dominate my mind and my actions. Is that the birthplace of passive aggressive behavior: wanting to be liked by everyone, while still wanting to succeed or see change?
Who was I to tell my friend what “better” looked like? Sure, my corporation gave me that title and that permission, but I didn’t deserve it. I didn’t earn the right to make anyone feel inferior or call all of the shots. But, that’s what my company rewarded. Results at any cost. I’ve reflected on this experience for years. As someone who has studied and taught leadership for 10 years, how could I get it so wrong?
One of the behaviors of a great leader is the ability to have tough conversations. All of the ideas swirling in our minds about others, they have to be communicated or expelled; otherwise, they will fuel disconnect and mistrust. In my argument with my friend I thought I was doing just that, having a difficult “management” conversation. Here’s the fundamental error: these conversations assume that the manager knows better. That it is his or her’s job to help the other person develop self-awareness, adapt, and grow. What a luxurious and distinguished responsibility! Never once in my conversation with my friend did I consider what I had done wrong or even why I cared so deeply in the first place.
As I think about my friend today, I remember the best compliment anyone has ever given me. One year at Christmas we decided to give everyone a list of compliments, written by the other members of our team. My friend wrote to me, “You’ve got more gumption than any person I know.” This meant so much to me because I aspire to be brave with my life and bold with my values. But I can’t help but question that sentiment now.
My friend, I wasn’t brave in that moment. Thank you for calling me out. Thank you for teaching me the hard lesson of what it means to be brave. It’s not screaming loudly to get what I want or wielding some superficial power given to me by Corporate America; it’s having the guts to expose the reality of a situation, from multiple perspectives. It’s recognizing that my perspective is in no way superior. It’s realizing that what I’ve been taught to do and say isn’t always the right thing to do.
My friend, you taught me that and I am forever grateful for your leadership.
Dee’s Essay (The POV of the gen-x direct report)
Have you ever said yes to a request and then, after a few minutes of really thinking about said request, completely regretted it? Well, here I am staring at this screen wondering what to share and what people would actually want to read. My dear friend Barb thought it would be cool for us to write a parallel story about our work experience, compare notes, and then publish it. Wait, what? PUBLISH, as in for a ton of strangers to read and judge? Oy. What have I agreed to?
See, Barb has this magical power over me. Over a lot of people, really. I used to call her Julia Roberts. Most of the guys we worked with had a crush on her and the gals envied her free-spirited and well-traveled life! But more than being Julia Roberts, Barb has always been one to push me outside of my comfort zone. I haven’t always liked it, but I’ve always appreciated it. We haven’t been work colleagues since March of 2017, but she still has this power over me! WHY?
Let me back up a bit. I have always been a worker bee. I’ve had a paying job since I was 13 and I know what it means to really work hard. I cut my teeth in the restaurant business, learned early what it means to show up, build great relationships and work as a team, but to also take responsibility for my own actions. I have lived by this standard for a long time. And while I’ve always had a strong work ethic, I never finished earning my college degree, never had a desire to climb the corporate ladder, be the boss, or be in the spotlight. My goal has always been to make a good living by doing good work that I’m proud of and to be appreciated for giving it my all. (Freud would have a field day with me.)
Fast forward 30 years. When I met Barb, I’d been in the corporate world for about 14 years, was married and had a 7 year-old daughter. Barb was quite a bit younger than me (by more than a decade), single, degreed, and gorgeous. Like I said, Julia Roberts. We became fast friends. Admittedly, I was a little “jealous” of her. Not in a real green-eyed monster sort of way, but because of what I felt were my own shortcomings and insecurities. We worked on projects together but had different roles and responsibilities. And then one day our company was acquired, our bosses left the organization, our headquarters were now out of state, and we were a team of two owning leadership development for a company of over 100,000 employees. There was so much change in such a short period of time, and just like that, Barb went from being my colleague and pal to being my boss.
We went into battle together…us against the big corporate giant that now ruled over us. We found our way together, created amazing programs together, and it solidified one of the most important relationships (outside of my family) that I’ve ever had.
I’ve read that soldiers on the front-lines have unbreakable bonds, and honestly, I feel like that is what we experienced. In 2016, I was pushed so far outside of my comfort zone that I had episodes where I physically felt like I was going to die. It put a strain on my family life, it put a strain on my body, and at times it put a strain on my feelings toward my most trusted colleague and friend. But I couldn’t say no, I couldn’t say that I was at capacity, I couldn’t let my friend down. There were many times I wanted to say “I quit.” But I wasn’t a quitter. At times I wanted to say to her, “Stop caring so much about the quantity of work we do and how others perceive that. Let’s care more about the quality of work we do and help others understand why that’s so important.” But that’s not how it was and it was out of my control. I was resentful at times because my personal life was really suffering.
Another wise friend once told me, “Don’t give the best of you to work. Save the best for those you love.” Well, that’s not so easy when you genuinely love and care about the person you are spending (much) more time with than your own family! As women, I think we put so much pressure on ourselves to be the perfect person to everyone else that we end up losing sight of what’s truly important to us…until we reach a breaking point.
Personally, having a good paying job so that my family is taken care of and my daughter can pursue her passions are what keep me in a place that I don’t always love. But I like it, a lot, and I respect and enjoy the people I work with enough to keep going. I always try to make an impact and that’s enough for me.
For Barb, the urge to break free of corporate life was calling. So she left me (uh — I mean our company) and once again I was a little bit jealous of her free-spirited and well-traveled life. My partner in crime, the person I adored, the person who sometimes sent me over the edge with her desire to prove herself, my supervisor, my friend…was gone. And just like that, I felt responsible for where this train was headed.
Wow, we viewed that totally differently…
Barbara: After going through this exercise, we were both surprised by the other’s insecurities. For Dee, she had no idea that I cared so much about what she thought of me. For me, I had no idea that she attributed her poor health and job stress to my leadership style. I’ve spent the last month thinking about it. I am an intensely driven person and the people around me respond in one of two ways: 1) It’s contagious. I’ve been followed into the weekend work trenches by so many incredible people. OR 2) Hard pass. I’ve known that for 15 years, but I didn’t really know what it felt like to be someone in Camp 1.
Dee: The big revelation for me is that Barb and I spent SO MANY hours and days together, in the office and traveling the country, living the same existence but with such different perceptions and perspectives! The word “driven” is just so personal to each of us. I have drive in many areas, and yet it manifests itself so differently from Barbara. This blows my mind because we are both totally driven to help others reach their own potential and be their best selves.
After this experience, we are even closer and we are a little bit changed. It was the best possible way to actually digest feedback. I (Barbara) have probably had 20 people tell me how intense I am, but I never actually knew what that meant until Dee was brave enough to join me in this experiment.
So, who do you need to hear from?
Your significant other? Your boss? A peer? A best friend? Ask someone you trust to give this exercise a try. Here are a few tips:
Select someone you respect. You need to be able to talk to them about what you wrote in a productive and honest way.
Pick a specific instance/experience to write about. It’s much easier than a generic prompt. It doesn’t have to be a difficult situation or work related! It could be something sweet, like the first moment you met your significant other or when your first baby was born. You do you.
Use deadlines and define what accountability looks like. We gave each other two weeks. For accountability, you are looking at it! We decided to create something to share. Maybe yours is a reward? Or an outcome?
Good luck! If you try it, please let us know what worked and what didn’t work. We’d love to hear from you!
