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

5 min readSep 1, 2022
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:

  1. Direction — Good managers ensure that every member of their team understands exactly what is expected and when it is expected.
  2. Coaching — Good managers coach their people toward both short- and long-term success, helping them understand what they should continue to do and where and how they can improve.
  3. Career — Good managers invest in their people’s careers in a way that considers their long-term goals and aspirations, beyond the four walls of the current company, and certainly beyond their next promotion.

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:

  • Fulfilment — “How fulfilled are you by the work that you do?”
  • Discretionary Effort — “How willing are you to put in effort beyond what is expected?”
  • Pride in Employer — “How much do you agree with the following statement: I am proud to work at [Employer]?”
  • Employee Satisfaction (eSAT) — “Overall, how satisfied or dissatisfied are you with [Employer] as a place to work?”
  • Employee Net Promoter Score (eNPS) — “How likely are you to recommend [Employer] as a place to work?”
  • Intent to Leave / Intent to Stay — “How much do you agree with the following statement: ‘I am seriously considering leaving [Employer]’?”

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:

  1. Deliver an aligned result
  2. Enable the success of the people on your teams

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:

  1. How clearly does your manager communicate what is expected of you?
  2. How helpful is your manager in prioritising your work, including helping you figure what not to work on?
  3. How collaborative was your manager when setting your individual OKRs?
  4. How collaborative was your manager when developing the team’s OKRs?
  5. How helpful is your manager in assisting you to navigate the company changes that impact you and your job?


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:

  1. How frequently does your manager solicit feedback from you?
  2. How consistently does your manager provide you with specific praise for good performance?
  3. How helpful is the feedback provided by your manager in improving your performance?
  4. How responsive is your manager to your ideas or concerns?
  5. How comfortable do you feel going to your manager with a safety concern, no matter how small?
  6. How much do you agree with the following statement: “My manager cares about me as a human being”?


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:

  1. How supportive is your manager of your growth and development?
  2. (Repeat) How much do you agree with the following statement: “My manager cares about me as a human being”?

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