At my OKRs Product Team Workshop last week, we began by writing OKRs Scary Stories. Here is one, perfectly timed for Halloween.

Ever wonder where the word "roadmap" actually came from? In the 1890s, bicycles were a key form of transportation within cities, and some of the first roadmaps were created to show how to bike from one part of New York City to another. With the rise of the automobile, travel between cities becomes more common, and organizations like the American Automobile Association provided printed roadmap directions for travelers. In the 1980s, Motorola began using the term roadmap to align technology and product development. Ta-da!

So you are a senior Product person who gets recruiter calls all the time. You enjoy the Product space but you want a change. Where do you go to use your skills in a new way? The hip tech General Manager? CEO at a startup? A cushy 9-5 gig? Professional chef? Writing Nano-letters in your den?

A user journey map is a great way to unpack the customer needs that make up a compelling product roadmap.

Objectives and Key Results (OKRs) are ideal for product teams, but only if done right. It’s easy to get caught in endless to-do items and forget about the real objectives - making customers and your business successful. I’ll be giving a workshop on doing OKRs right, handling what goes wrong, adjusting course, and managing expectations.

"The Mona Lisa has a huge social media presence. Her picture is everywhere. But she doesn’t tweet. She’s big on social media because she’s an icon, but she’s not an icon because she’s big on social media."
Becoming an icon is a tall order, both in art and product. How does your organization balance product and marketing? Do you believe in product-led growth?

Getting buy-in for a new roadmap can be difficult, with numerous stakeholders wanting different things. I have found it helpful to reach decisions without the politics and posturing of large roadmap review meetings. Of course, this is doubly hard if you are introducing a new format of roadmaps, one with strategy and outcomes rather than dates and features.

How has your Product practice changed since COVID? What is surprisingly better now - and maybe shouldn’t change even after we get a solid vaccine?

What is the difference between a CPO and a VP of Product Management? A director? Senior PM? Naturally it depends on your organization. But in my experience, the higher you rise, the more you have to influence across the organization (and deal with politics). These soft skills are the most critical success factor for product, but also the hardest to learn.

"I have many friends who started out as designers and user researchers or other folks on the UX side, who have found their ways into product management. We go to lunch and they're just as nice as they've always been!"

One of my early product jobs was at a startup with money and the CEO's exciting vision. We also had Shiny Object Syndrome, with a million ideas and tactics for how to bring the vision into practice. That's where a smart product person's strategy comes in: narrowing focus to a few key things we can do well, and getting alignment from all the stakeholders.

Most times I’ve left a job (or a client) it was about culture. The gig or the company wasn’t satisfying. (See my story about quitting here.) I usually had another job lined up, though.

“Everyone has a plan ’til they get punched in the mouth.” —Mike Tyson. No matter how well you plan, change is unavoidable.

"Sometimes product managers are asked to be the rational person, the grownup in the room. Others may be super optimistic, like salespeople or the CEO. Product people have to be imaginative, too, but also say, 'wait, let me break this down, we can’t do everything at once.' Product success is that level of imagination combined with an ability to plan your way there and to lead a team."

For extra fun, some of you are in charge of multiple products in a company's portfolio. In theory, each product should add to profitability and the whole should be greater than the sum of its parts. In practice, companies tend to focus on Product 1, the biggest source of current revenue. Longer-term ideas and projects get kicked further down the road and Product 3 never becomes a reality.

I recently saw a documentary about General Magic, a Silicon Valley start-up that invented smartphones... in 1994. They had heaps of talent and money, and a great prototype. But they failed spectacularly, for a lot of reasons.

Outcome Teams are the next stage of team enlightenment. They exist to make a business successful. More and more companies have hired GMs to lead these teams who are really Product leaders on steroids. Engineering, U/X, Sales, and Marketing report to GMs directly to ensure alignment to these outcomes.

Most of us can remember a time where it felt great to be on a team: everyone was on the same wavelength and you were happy and hyperproductive. How to replicate it? One way is to run what I call an Awesomeness Retrospective.

A Product resolution this year was "Understand your customers so well you could play them in the movie." What’s your favorite way of learning how your customer thinks?

The best roadmaps are not about features and dates, but about value, the benefits to the customer and to your business.

Objectives and Key Results (OKRs) work the same way; the hardest things about both is avoiding the temptation to make them into a glorified “to do” list.