Episode 21: Being a Dynamic Leader in a Modern World

Q&A

I'd love for you to talk a bit about how you see companies make the successful shift from project output (long-term planning) to product outcome (“just enough” planning).

The crux of the challenge is often adopting new practices. In software terms, we  think about road maps–but large organizations think about master plans. And once something's on the master plan, it's a promise that they've made internally, to their customers, or to Wall Street. You're on the hook. So, you have to be very careful about what you're promising. These planning tools become explicit or implicit commitments to one another. There’s a difficult relationship between th e kind of planning that happens in dynamic circumstances compared to the requirements of Wall Street that have an eye on these master plans and have real expectations. 

I think that outcome-focused planning is one part of the solution. When we think of outcome-oriented road mapping, we're thinking about product feature-type road mapping, but product features are in the plan because they allow for a certain enhancement of a user experience or a business value outcome. And the feature itself isn’t what matters, but the thing that feature enables for either the user or the business. 

We have great collaboration tools online, but you did a really good job in your book articulating why being together in person–whiteboarding, brainstorming, encouraging different thinking–is so critical and important. What is our new remote reality? 

I've always been really biased toward in-person. Part of that is my personality type; I'm an extrovert. I need to feed off other people's energy. But also, there's something about generating thought collaboratively that feels amplified when you're together with a whiteboard pen. That just doesn't happen when you're using an online whiteboarding tool. So. I actually believe that facilitation skills are critical for managers and leaders across levels; it needs to be a tool in that toolkit. By the time you're at the senior manager level, you need to be an excellent facilitator of groups if you want to be effective.

Can you talk about how you have coached businesses that are stuck in a mold when it comes to trying new things? How have you been successful where there's been a calcification of innovation?

The second thing is understanding the ways in which they can accept something new. There's a lot of reasons that people in these large organizations behave the way that they do and make the decisions that they do. Well-documented practices that keep them profitable or on mission. What I've learned is that you have to help people make changes so that they can become what they already want to become. You hear people say, “meet them where they're at and then go from there”, which is true. But what does that mean? It means they have to envision their own future, and you have to take that sense of agency and feed it. 

Tell us more about your book, Farther, Faster, and Far Less Drama: How to Reduce Stress and Make Extraordinary Progress Wherever You Lead. What was developing it like? 

We worked on this book for four years and when we started it, it was a really tactical book. This is a shout out to all of my under-recognized leaders. We didn't feel like we had permission to write a leadership book. We really had in our minds that we were software product management leaders, or innovation management consultants. Like our mindset about ourselves was so much more limited than the actual value we were delivering to our customers. It was in conversation with our customers and our collaborators that we saw the book was not just about the tactics of “how to”–it was about the role of a leader in a modern software organization, or any modern organization.

Can you share a bit about what you're going to be covering in your presentation at Mind the Product? 

The book is organized around four leadership motions, and we're going to go over all of them. What are they? What does it look like when you're flowing in leadership? I'll also be sharing some case studies. And then a little later in the day, the Mind the Product folks invited me to participate in an author Q&A, as well as the presentation.

And lastly, what does digital mean to you?

I always think of the world as atoms or bits. Anything that involves bits, that's digital.