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My first 30 days as a Product Manager 

Stuff I wish someone told me about besides my hair falling out…

No one said it would be easy. Today, clumps of my thick curly black hair fell out while showering. Stunned, I forced myself to reassess the amount of stress I’ve been putting on myself. I joined SigFig in the beginning of October, leaving Opower on a Monday, and starting work on the subsequent Tuesday. Determined to keep my momentum, I didn’t want to take any time off. This was it. I finally found my dream job as a software product manager at a start-up with a tremendous growth trajectory. A growth opportunity—everything I could hope for, right?

I wish someone would have told me the following:

1. You are more than just a PM at a small start-up, expect to be a project manager, product manager, and engineer herder all at once. If you expect to excel in all three then you’re in for a royal disappointment. Focus on what’s important. In the first month, becoming a project manager 80% of the time and product manager 20% of the time was a conscientious decision to to launch our partnerships on time. Knowing when to recalibrate your role percentage breakdown will help you succeed as a Jack/Jill-of-all-trades.

2. You’re going to be hated at one point, I felt like the most hated woman at SigFig because I had to be pushy and authoritative in order to be effective. As a product manager, your job is to drive the product vision forward at whatever means possible. You need to track your team and instill a culture of accountability and organization. When I first set up a Jira system to assign work, measure progress, and hold developers accountable, I met a lot of resistance. Comments like “Bo is the Jira nazi” or “your tickets are crushing me” made me feel uneasy and apologetic at times. I felt uneasy since I’ve strived to be liked at work and in my personal life. However, for the first time it seemed like being effective was undermining my likeability. And I’m okay with that. Sheryl Sandberg was right: many women struggle with likability vs. respect in leadership/management roles. In my case, I’m still navigating the space between being agreeable, friendly, and myself and when to be firm, serious, and possibly construed as “bitchy”. Realizing that you can’t please them all is the most liberating step of all.

“If you worry about hurting people’s feelings and disturbing the social structure, you’re not going to put your ideas forward.”

— Malcom Gladwell from David and Goliath

3. Know when you are set up for failure every start-up brings in someone thinking, hoping, expecting he/she will be a miracle worker. This person will change everything. When you are brought in with the expectation to whip an entire organization into shape, shift the gears, build processes and systems, and instill project management culture— you have to ask yourself— “am I being set up for failure?” Because there is 1st degree ignorance and there is 2nd degree ignorance.

First Degree Ignorance accounts for what you don’t know. You can anticipate your deficits and work around them with help.

Second Degree Ignorance is you don’t know what you don’t know. These are unforeseen difficulties that no one warned you about. Therefore, it’s tricky to account for second degree ignorance and maneuver accordingly.

Second Degree Ignorance is what slaps you in the face when reality defies your hard work. At which point, you need to ask yourself “do I have all the information, training, and support to succeed?” If the answer is no, go back to the drawing board and gather your missing pieces. For me, this was realizing that I could not successfully manage a project and team of engineers without any onboarding or deep understanding of the core product first.

Know when to push back and ask for the information, tools, training, and help to succeed. Otherwise, you are unwittingly setting yourself up for failure. Don’t be afraid to ask for help when you are drowning. Our CTO stepped in when I told him there was no way I could single handedly launch a partnership on time by myself.

4. Be kind to yourself there were countless nights when I was up until 3am beating myself up about why our team was behind schedule, why a sprint didn’t go as planned, why people didn’t show up to stand-up, why I couldn’t turn things around faster etc. Sometimes you’ll feel responsible for the entire team’s failure because your job is to keep the team on track. As a woman, I tend to attribute an unfavorable end result to myself thinking that the output is a 1:1 function of my efforts and hard work. Maybe I didn’t work hard enough, maybe I didn’t incentivize the developers to work efficiently, maybe I didn’t delegate the tasks correctly, or maybe I didn’t prioritize properly. However, at the end of the day, if something doesn’t ship on time, it is a collective organizational failure, not just yourself. Take accountability and move on.

I wish someone would have told me these things before I started as a software product manager but I guess these lessons fall into the second degree ignorance bucket and are meant to be learned from experience.

So, this morning, after cleaning up my disconcerting clump of hair from the drain, I vowed to myself to chillthefuckout, breathe, ask for help, and stop being so hard on myself.

Update: I’m happy to announce that after writing this post, I will be joining the new Product Experience team at SigFig focused on shaping the user experience for our core product. There will be many new product lessons to be learned in the next thirty days.

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Product-focused investor empowering underestimated founders. Writer. Advisor.

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