Andrew Tsui

The Product-Design-Engineering team is the asset to work with and it is the problem that needs to be made clearer, the problem that needs to be thought of in an iterative way, and the solutions delivered in such a way as to address increments of user value. We’re in the third decade of the 21st century and it’s long past time to discard waterfall thinking. The thrust of this article ought to be “the problem isn’t the team, it’s the problem definition.” When you’re crisp in defining the problem and success criteria, the problem becomes far easier to get motivated about and to be solved quickly and creatively.

When you see Product priorities shift faster than you expect or feel otherwise able to keep up with, remember that the shifting is not a problem for you to solve; it's a problem that you should decide whether to adapt to or not. This is where the concept of "candidate market fit" from Phyl Terry's book Never Search Alone plays a big role. In any enterprise, shifting priorities can be due to any number of reasons. If those reasons align with your assessment or thinking, then you likely do not perceive those shifts at all. However, situations where lack of transparency, rigor, or vision converge somehow and contribute to shifting priorities should prompt you first with: "Is this environment right for me?" and "What can I realistically do?"

I have found that domain expertise can be fundamentally limiting to a Product Manager's success in three different ways: (1) the expertise doesn't help you get unstuck from the mindset of "just make the way we do things better", (2) the expertise closes you off to learning from adjacent or entirely different industries (value chain) without experimenting on new patterns or ways of working, or (3) the expertise holds you back from zooming up in terms of strategy and business model. Find a way to bust through those challenges, and you may find yourself able to leverage that domain expertise much more successfully!

This LinkedIn advice article misses the mark about iterating and differentiating one's offerings. Whether the platform is Upwork, Fiverr, or something else, you need to measure impressions (think click tracking if the platform doesn't offer analytics) and conversion to a prospect call. With that, you can gather data about how your offerings either do or do not resonate with prospects. If you lack volume of prospects, that's where your network comes in; look for feedback, not necessarily business, in that case. You should be testing whether your industry, product size, and/or problem space focus is working; additionally, you should be gathering data on why people are not hiring you. Iteration towards differentiation, in a nutshell.

Leadership is a tricky area to mentor due to the way we often present ourselves in work situations. Those behaviors are hard to disconnect from the emotions and context of a work setting. And consequently, they’re difficult to convey to a mentor. That said, there is a way to get help! It involves looping in a handful of trusted colleagues to provide you their perspectives on how you lead. The key word is ‘how’. Ask for any example, no matter how small, where you showed either the potential to lead or actually demonstrated leadership, along with the context. Get 3-5 perspectives and send that to your mentor. Then collaborate on an action plan that, among other topics, describes your strengths and tendencies that you can lean on to lead.

In cases where the relationship between an employee and a direct manager is challenging, a mentor can be a massive opportunity and point of leverage! First, find a mentor whose experience resembles the direct manager in stage of company, not necessarily industry. Second, seek out someone who can dedicate at least several sessions to working with you to create an initial action plan. Third, do some homework to frame your challenges with an introspective and assumptions-busting mindset. After all these steps, you’ll be in great shape to move forward and figure out how, if at all, to move the employee-manager relationship forward.