“When They Win, You Win” (Book Review)

Image Credit: When They Win You Win

Russ Laraway is a military commander turned people leader, currently working as Chief People Officer at Goodwater Capital. I recently heard Laraway talk about his first book “When They Win, You Win” on Jason Knight’s great “One Knight in Product” podcast and it prompted me to read Laraway’s book. Laraway’s frustration with a lack of good managers drove him to write “When They Win, You Win”, arguing that “you can become a better manager, no matter what kind of person you are.”

I’m sure it’s not unique to product management, but I’ve seen plenty of great individual contributors catapulted into a managerial role and, frankly, struggling to manage people. I learned a few lessons the hard way when I first became a manager, desperately looking for guidance on how to best manage people.

Image Credit: Amazon

In “When They, You Win” Laraway concentrates on three key elements: Direction, Coaching and Career:

If we focus our managerial activities on Direction, Coaching and Career, Laraway argues, we will have engaged employees (E) who deliver the expected results (R): 3 <-> E <-> R. Employee engagement is a commonly used term, but what does it actually mean?! Helpfully, Laraway shares a number of concepts and questions that we can use to measure employee engagement:

I was quite surprised to read about one of the biggest factors affecting employee engagement: the manager. Perhaps I’d underestimated the role and impact of a manager. In the book, Larry Emond, former managing director for Gallup’s Global Leadership Advisory, states: “The manager explains seventy percent of engagement.” This means that when we observe a variance in engagement, seventy percent of that variance is statistically explained by a variance in manager quality. So if the quality of managers is so important, how do we measure good management?! Laraway keeps it simple and highlights two core responsibilities of the manager:

He points out that most managers aren’t only leaders of a team but also members of a team. Hence the title of his book “When They Win, You Win”. Still, the manager is responsible for everything the team does or fails to do. With that in mind, let’s go back to the aforementioned elements that mangers need to focus on: Direction, Coaching and Career. In the book, Laraway outlines what’s expected of a manager for each of these three areas and lists related manager effectiveness questions.


Direction setting anchors the team to an aligned result through the combination of purpose and vision (long-term), and OKRs and ruthless prioritisation. There are a number of manager effectiveness questions that you can ask your team to find out if you’re providing robust and clear feedback to them:


Coaching enables team members to achieve OKRs. It comes in two forms: coaching to improve what’s not working and coaching to continue what is working. The former involves giving feedback that, no matter how hard we try, almost always induces a threat response. The latter involves helping folks explicitly understand what they’ve done well so they can do more of it. These are the manager effectiveness questions we can ask our direct reports to find out whether we provide strong coaching:


A manager must do more than help employees succeed in the job they’re doing now; they must help them discover their long-term vision for their careers and show them what actions they can take right now that will allow them to make tangible progress toward it. Laraway stresses that helping people think intelligently about their careers is one of the most valuable activities a manager can take on. To learn whether a manager is doing this effectively, we can ask our team members the following questions:

Main learning point: The way in which Russ Laraway brings management back to its essentials — delivering aligned results
and enabling the success of the people on your team — really resonates. Similarly, him breaking manager down into three core responsibilities — Direction, Coaching and Career — makes for a very compelling and actionable book and approach to people management.



Product at Intercom, author of "My Product Management Toolkit" and “Managing Product = Managing Tension” — see https://bit.ly/3gH2dOD.

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Product at Intercom, author of "My Product Management Toolkit" and “Managing Product = Managing Tension” — see https://bit.ly/3gH2dOD.