November 16, 2018

The Messy Middle and Career Magic

By Brittany Adams.


Three years ago, on a set of cheap Google-branded bean bags in a San Francisco Financial District office, I delivered the “I’ll do it” that would be my first step into product management. Saying that I was excited is a serious understatement. I had traversed through several roles at the company. I had smiled ear-to-ear as a content manager seeing my copy appear on our company’s website. I had walked anxious laps around the building before presenting my product exploration to a dozen seasoned product pros. And now, our VP of Product was giving up sitting properly in his bean bag while attempting to offer me a role as the company’s newest product manager. I. Was. Pumped. I had no idea what I was getting myself into at the time.


The beginning of a journey holds its own special value. However, the funny thing is that beginnings go by rather quickly. It’s onward to the middle, which is lengthy and filled with challenges, and at some brief moment, you’ve reached an end.




That middle part?


The one between the brief “beginning” and even more brief “end?”


It’s messy.


The middle is filled with “I don’t know,” “we’re not sure,” “we don’t know how,” “we’ll figure this out,” and “we’ll learn how to do it.”


As Brene Brown, my inspirational guru and New York Times bestselling author says, “’s also where the magic happens.”


At Hotwire, that beginning was gone in a flash. The majority of my time was spent in the middle. And now, at Silvercar as a product manager? The beginning has long past. Every day I exist in the “messy middle.”


And it’s in this middle that some of the most rewarding lessons have appeared. Some of which I’m going to share with you below.


You Can Never Be Everything to Everyone


You may think, “That’s a given, Brittany,” but it never surprises me that we all try to avoid making others feel uncomfortable at some point in our lives. We’re social beings that don’t want to be shunned. When I encounter colleagues who appear immune to the thoughts of others, it’s rarely because they “don’t care.” More often than not, it’s because they’ve been hurt by caring too much in the past. Who of us can’t sympathize with that?!


Product management is a role that places you right in front of every stakeholder’s path, and therefore… their wishlist. The most challenging, but most honest advice I ever received was, “You’re doing your job well if at least one person is frustrated with you.” It’s a tough way to think about the role, but it’s true. There are more people and more ideas than there is time to prioritize all of them. Leaving the office knowing teammates or colleagues are frustrated is incredibly difficult. Therefore, you have you ask yourself an essential question. “Have I made this decision with integrity?” If you believe in the decision you’ve made, sometimes that’s the best that you can walk away with.


Getting a group to determine priorities means you’re also at the receiving end of some pretty strong emotions. Don’t get caught in “me versus you.” Instead, take it to the board, or Powerpoint, or post-its! Yes, this role operates at the intersection of design, development and business needs… but I also honestly say it requires part life coach, part therapist and part translator. Help others work together to solve problems and believe me, you’ll leave your mark.


Adopt the “Relevance Test” – Let Meetings Fall Off Your Calendar


Now, I don’t mean to let all meetings fall off your calendar. I challenge you to reflect on and experiment with which meetings truly drive your team’s and the business’s success forward. Practice your own variation of Essentialism. I find that my time as a product manager is never fully committed to being in the weeds with my team, or looking out to the horizon with my stakeholders. Instead, like a pendulum, I’m constantly swinging between one state and the other. This is especially true as product and development teams end old projects and begin new ones. You can’t be everywhere at once.


But our schedules regularly look like we’re trying to! Seriously, you know who some of you are with those wild calendars.


I noticed two weeks ago that a few regular check ins had fallen off of my calendar. (This week in particular has been largely open and insanely productive). I decided I’d let them stay off for a while and see how communication would go by other means. Just this morning, while working on a project for Operations, the VP of that team stopped by in person.


Guess what ensued?


Questions answered. Five or six pieces of app-related feedback received. Shared understanding created. JIRA tickets made. Trust built. Fifteen minute ad-hoc meeting over.


Now that’s productive!


In order to avoid the habit of unproductive meetings, you have to interrupt your pattern and reflect on its value.


Even more important, some of these unnecessary meetings kept me from my team, which kept them from getting answers, which kept us from completing work, which is what I was going update meeting attendees about in the first place! It’s all about balance. Nobody else but you can keep your balance in check, but others will undoubtedly sense when you’re out of balance.


Ask Yourself What YOU’RE Truly Proud Of Before Any Performance Review


I moved to Austin eighteen months ago by following a feeling.


I didn’t have a job or housing lined up. I. Just. Went. Does that mean I immediately landed a gig and the perfect housing? No way! Just like in my role here, the shiny beginning of my moving to Austin quickly faded into the messy middle. It was a struggle to stay inspired.


While applying for roles and calling on my inner product manager, I began a practice that I continue today while working at Silvercar. Every day that I feel proud of something I’ve accomplished, small or large, I write it on a post it and stick it on a flip chart in my apartment.


Now, I personally do this to build up some major inspiration mojo, but it has also armed me with gratitude before going into any performance review. You take on a role to join a team, to accomplish goals together, to cross the finish line together. That said, you’re the one who has to feel proud of what you’ve done at the end of the day.


Constructive feedback is valuable, and yet don’t grow to rely on it. Follow your instincts, reflect on what you’re proud to have accomplished, and hold that close. Your confidence will skyrocket as a result.


As I mentioned earlier on, the beginning and end of a journey are usually fleeting… yet they’re the parts we desperately want to live in the most.


It’s the “messy middle” that holds the lessons, the struggles, and above all else, the growth.