What's the biggest challenge you've ever faced as a product management leader and how did you overcome it?

Two constant challenges for me in any product role has been finding the right way to say no. This could be to your customers asking for a particular feature or your organization that has decided to prioritize certain aspects differently. 

The best way to overcome this challenge is by having your facts and data clear. For example, it is easy to convince leadership about your prioritization rationale if you have data to back up your claims, whether it is potential revenue or customer impact.

Without going into specifics, the biggest challenge has been cross-organization influencing. My time at both Microsoft and Google has exposed me to lots of intra-organization projects with varying levels of buy-in from each team. The level of effort and coordination required to pull not one, but two organizations in the same direction can be enormous.

As a PM - at any level - it's your role to effectively communicate why what you're trying to acheive makes sense for other teams, your company and ultimately your customers. Even if you're aligned on principles and strategies, there are dozens of other factors that you need to be able to navigate such as resourcing, ownership, tech stacks, recognition, branding, leadership opinions and timelines. 

Oh, this is a tough one! Since the AMA is about Technical Product Management, I'll answer from that perspective.

It's common for a successful company and product to face tech challenges after they've achieved significant growth. When you're a startup moving fast to find product-market fit, you might not prioritize the technical hygiene of your product. Then, as you scale up, you may need more time to go back and clean up or improve your technology. Eventually, this issue needs to be addressed, as outdated tech could limit future success, pose security risks, or even hinder expansion into new markets.

I've been asked to lead product and R&D teams through situations like this, which can be extensive, multi-year efforts.

My biggest takeaway is that more than focusing solely on technology is needed. It's easy to say, "Our tech stack has reached its end of life, and we need to adopt this new one." But stakeholders, like executives, customers, partners, and investors, care about business results. So, always frame your work regarding the outcomes you'll create, such as faster scaling, improved product experiences, or reduced operational costs. By emphasizing these outcomes instead of just the technology, you'll gain support from key stakeholders, which will help you secure the necessary time and resources for success.