Anticipating Pitfalls In First Product Manager Role In Early-Stage Startup
I used the premortem concept in my career planning in early 2024. I’ll reuse it now. Why? Studies show people who imagine negative outcomes and their reasons do better than those who only think of positive outcomes.
What if, years (or months) later, I find I've failed in my job at FlexAI? What might the reasons be? So, in this post, I time travel to the future. Here's my introspective analysis.
I’m using dialectic thinking. Dialectic thinking is the ability to function while holding two opposing ideas in your mind. On one hand, I can fail at this startup job. On the other hand, I want to thrive in it.
Here’s a list of possible reasons. I’ll dive into each:
Insufficient Knowledge
Divided Attention
Hesitate To Communicate
Avoiding Disagreements
Seeking Work-Life Balance
Ideal vs. Reality
Remote Work Hurdles
GenAI Tools Blocked
Freelancers Prohibited
I spend 1 hour and 39 minutes writing this. You need 7 minutes to read this.
Related:
Insufficient Knowledge
I might fail if I lack knowledge about Kubernetes pods, Hugging Face Accelerate, the Linux kernel, neural network training, GPU performance benchmarks, or inference of generative AI models. I might also fail if I struggle with concepts such as fine-tuning, PEFT, RAG, epochs, or CLI.
Mitigation
I will dedicate time during and beyond office hours to learning these concepts. For example, I will study Microservices by O’Rielly.
I will reach out to AI Product Managers to learn from their experiences.
I will search for podcasts and newsletters to keep track of the latest in GenAI, such as Kubernetes Bytes GenAI episode.
Divided Attention
I might fail by dividing my time (GIF from Tenor) between product management and go-to-market/product marketing. This division will dilute my impact on the engineering team.
Mitigation
I could allocate specific time for product management and go-to-market product marketing.
I could track my daily tasks and categorize them as marketing or product management. I could discuss my weekly tracking with the CEO and CTO to get their buy-in.
I need to communicate my tasks and responsibilities to my colleagues to set expectations.
Hesitate To Communicate
I dislike night meetings because they keep me awake thinking about work. I might fail if I hesitate to meet with my California colleagues (8 hours away), but avoiding those meetings would reduce my efficacy.
Mitigation
I work in a globally distributed company, so I need to set a routine. To reduce the worry about night meetings, I can create predictability by blocking some nights without meetings.
I can use Loom, Slack, Notion, Email, and Google Docs for more async communication with my colleagues across time zones.
Avoiding Disagreements
I might fail by trying to be a friendly colleague who doesn’t push back or create friction. I will fail if I hesitate to bring up countering viewpoints or challenge the founders' approach. This can lead us to build what we want instead of solving the customer's problems.
Mitigation
I want to channel Kim Scott’s Radical Candor. I should bring up opposing viewpoints when necessary because it will improve decision quality. But, I should soften my start-up and explain why I care about my colleague when I bring up an opposing viewpoint.
It is psychologically safe to praise (but not criticize) your colleague in a 1-1. Avoiding friction by not criticizing is easier. I should find ways to get honest feedback from my colleagues. I want to approach it like the Thank You For Feedback book.
One way is to present my point of view versus my colleague’s point of view. Instead, I can anchor meetings to customer needs and drive other perspectives towards meeting those needs.
Seeking Work-Life Balance
I may fail if I don't dedicate 60-80 hours a week to work (instead of 40). Product Management is a context-heavy job. It requires substantial time to absorb information through dozens of documents and meetings. The context-heavy nature of work keeps me thinking about work beyond 9-5.
I may fail at my family, friends, and fitness goals. Or, I may hesitate from sacrificing personal time or activities and try to do them all. At some point my mind or body might give up, which may result in burnout. At burnout, my productivity would be zero.
Mitigation
To address this, I will find aspects of my job I enjoy and inform my colleagues about my preferences. This idea is supported by the book "Nine Lies about Work", which argues against stressing over work-life balance. Work and life are not balanced on a knife's edge. They are not in an unstable equilibrium. The popular misconception is that work depletes you, requiring life to recharge. However, research shows that if you love just 20% of your work, you look forward to it.
A common time management approach suggests:
fill a jar with the big rocks first,
then the small rocks,
then the gravel,
then the sand,
then the water (or coffee).
But, Four Thousand Weeks points out that you have more big rocks than space in your jar. Thanks to Mindful Ambition for one part of the image below.
Some big rocks competing for my time apart from my job:
Meeting friends on weekends
Family time on weekends
Maintaining professional relationships weekly
Writing for a few minutes daily
I need to decide which big rocks to let go of.
To increase my impact without increasing hours, I need to become more efficient at my job. I can do this using software, GenAI tools, VAs, and delegating to colleagues.
I must reduce my weekend plans with friends to reduce time spent cooking elaborate meals.
I need to simplify my family’s weekly meal prep.
Ideal vs. Reality
I may fall into a trap I’ve seen other product leaders fall into.
Heads of Product (HoP) or Chief Product Officers (CPO) often face a common trap. They may listen to founders’ interests in building a true product organization and ask tough questions that either end their tenure or define the right process at the wrong time. Startup success may not correlate with its process.
Founders sometimes hire a product strategy expert with hopes of guiding the company's strategy, only to realize they wanted someone to execute their vision.
Mitigation
I will prioritize executing the founders’ vision over arguing with them based on my vision. In parallel, I will gather data to support my counter viewpoint. I will prioritize time building the founders' vision because they have the most stake in the company, the most risk, and the best understanding of the industry.
I will ask my founders about their motivations beyond solving a problem, such as fame, money, or skill-building. My actions will align with both their and the company's goals.
Remote Work Hurdles
I may fail because I work remotely. Most of my colleagues are in France. Many of them are co-located or meet often in Paris. I don’t understand French culture or language, which weakens my relationships with them. My ability to influence the company’s direction depends on having strong relationships with my colleagues.
I don’t like traveling for sightseeing. So, I’ve never applied for a Schengen visa. So, applying for a French business travel visa seems daunting.
Mitigation
It’s time to apply for the Schengen visa and visit France. Meeting my colleagues in Paris in person will strengthen our relationships.
I should use Gather to drop-in to colleagues when necessary and consider using Gather over slack.
I should schedule regular 1-on-1s with my remote colleagues to maintain our relationships. I should put in more effort to remember their backgrounds, family life, and preferences to maintain remote relationships.
I should aim to learn more about French culture by following virtual watercooler conversations, example French elections 2024, Eurocup (Football) 2024, or the Paris Olympics 2024.
GenAI Tools Blocked
I find tools like ChatGPT GPT-4, Perplexity, Mistral chat, Notion AI, and Grammarly Pro essential for my impact. However, some companies in Europe are blocking employees' access to generative AI tools.
I may fail if my company does not allow me to use Genarative AI tools. My productivity will drop without these tools, leading to more grunt work and longer hours to achieve the same results.
Mitigation
I should use GenAI tools without inputting company documents to make it easier to use them outside my company laptop.
I should help the company decide on GenAI tool licenses to standardize the process and allow employees to use some tools at the expense of not using other tools.
I can pay for tools out of my pocket.
Freelancers Prohibited
I feel comfortable outsourcing parts of my tasks to freelancers, like scraping data from the web, making a landing page, or design work.
I may fail if I am blocked from using freelancers. If I am blocked from using freelancers, I would need to work longer hours and do more grunt work or work that I'm not good at, which will take longer.
Mitigation
I can pay out of my pocket.
I can prioritize hiring freelancers for tasks that require minimal input from company data, like scraping competitors' pricing data.
I can reduce or eliminate the involvement of freelancers in tasks that require handling company data, like writing SQL queries on the company database.
Reflection - How Would A Premortem Help?
I was excited to do a premortem to convert my anxiety into concrete concerns. I can then review these concerns to assess their likelihood and think of corrective actions to include in my routines.
Related: