I learned the ropes of product management (including both strategy and stakeholder management) from a great boss, John Wang, who went on to become CMO for HTC and to found two companies. Who is your mentor? Who inspires you? How did they help you (intentionally or not)?

I enjoy conferences (speaking, running workshops, hanging out at the bar after). There is a feeling of camaraderie, of shared culture and mission among product people that is hard to duplicate any other way.

How has your conference experience changed during the pandemic? Has virtual worked for you? Who is doing it well? If you could choose a well-run virtual conference or in-person, would you go back?

We're coming up to Labor Day in the USA, a holiday when workers can have a rest and some can have a BBQ. It makes me think about product work in general. Product is such a cross-functional leadership role, it has to be harder over Zoom. Or is it?

"These days, agile is essentially the law of the land if you’re in product management.... But the resulting emphasis on sprints and short-term planning can lead to a lack of a larger product vision. It's also often incompatible with the longer planning cycles of enterprise customers and partners." I enjoyed this article in First Round Review.

I'm doing a survey: What software do you use for tracking Objectives and Key Results (OKRs)? Good old boring spreadsheets? Some sweet tool that I haven't seen? Something mildly annoying in the middle?

Do you remember General Motors' electric car, the EV1? It was built in the 90s, way before Tesla. GM decided that it wasn’t a viable business, recalled the cars, and crushed them — even though its customers were very happy. Now Tesla is reshaping the auto industry and GM is trying to catch up.

“A lot of people think a feature release schedule and roadmap are synonymous, right? You’ve probably heard that a hundred times,” says my friend John Mansour, of Proficientz. But he disagrees. “In my mind, a roadmap is a series of statements that communicate WHAT you’ll help customers accomplish and WHY those goals are important to their success.”

What happens when the customer says they won’t sign the big contract without a commitment to a specific feature this year? Or your CEO feels that extracting blood oaths is the way to ensure everyone is working hard enough?

“At some point, you need to start talking with the sales force about, ‘Hey, we think we’re going to be bringing this new product to market. What’s the best way to go to market? Can our current reps sell it, or should we have specialized reps? How do we get everybody trained up to understand the customer’s problem and the solution we’re bringing to market?”

A lot of folks worry that anything they share with customers on a roadmap will come back to bite them later. But my friend Janna Bastow, CEO of ProdPad, argues that "as long as we’re open and honest about our priorities, customers are actually very forgiving."

I recently saw a talk by AirBnB product people. They used to show photos of potential guests on their site. Then they noticed that potential guests who were minorities were getting rejected by hosts more frequently than white potential guests.

Do OKRs work with roadmaps? Indeed, they do. In fact, I argue that everything in your roadmap should tie back to your objectives. If not, why are you doing these things?

“Having the right strategy only matters if there’s total alignment around it. When marketing is telling one story, sales is selling something different, and engineering is building something different still, then product management’s strategy is hollow and irrelevant. The roadmap must align all the stakeholders around a common product plan.”

Shouldn’t we always try to build the right thing the right way to ensure scalability, reliability, and other measures of quality? No, we shouldn’t.

Sometimes in your roadmap it is useful to include your target customers. Ask yourself: Do you have distinct customer types with different needs?…

Ever noticed that the more features you have, the longer it takes to develop a new one? There are many reasons why, but the testing matrix is a large contributor. As you add features, you add the burden of testing not just each feature, but each feature in combination with every other feature. In software, this is commonly called regression testing, and unfortunately the size of this test matrix grows exponentially with the number of features.

Objectives and Key Results (OKRs) are goals shared at the team level, setting up teams for collaboration from the very beginning. See my article here. OKRs bring focus and results to an entire organization, measurably. That means they can help rally people to the roadmaps as well.

People who excel at both product and project management are often compared to unicorns because they are so rare. The responsibilities are different enough that people tend to neglect one set for the other and, unfortunately, it is usually the important but less-urgent research, strategy, and prioritization activities of product management that suffer.

"Your product roadmap is the prototype for your strategy. It’s your key to vision alignment. It’s your ever-adaptable communication aid, the one thing your team can coalesce around and use as a North Star guiding light."

When sitting down with stakeholders to discuss your roadmap, treat the meetings like customer interviews. They should be informal, one-on-one. Ask them about themselves. What are their goals? What is keeping them up at night? (And how are the kids?)