Skin in the Game: A Roadmap for Engineering Leaders To Find Meaning in Work

How to drive value and satisfaction as an Engineering Leader

Skin in the Game: A Roadmap for Engineering Leaders To Find Meaning in Work

Who is this article for?

For Software Engineering Leaders, both new and seasoned.


At some point in time of your management journey, you must have wondered what impact you create as a manager, and what value you drive for your organization.

The purpose of this article is to outline my understanding of how an Engineering Leader can cultivate "Skin in the Game," as well as to offer a roadmap for Engineering Leaders, both novice and experienced, to achieve success in their positions.

After working as an individual contributor for 12 years, I made the transition to management in 2019. As I complete my fourth year in this role, I still find myself pondering these questions. While the decision to transition was mine, and I followed a methodical process to make it, it took me a few months to adjust to the new responsibilities, team, and expectations (If anyone is at a similar crossroads, please reach out to me. I will be happy to chat). Once I was acclimated, I began seeking a deeper meaning in my role.

I recently read Nassim Taleb's "Skin in the Game" and found it to be an excellent resource for my needs. I was inspired to gain insights from a pragmatic thinker like Taleb on issues relevant to my field.

What is "Skin in the Game"?

In the book, Taleb argues that people should have a personal stake in the decisions they make and the risks they take, and that those who do not have "skin in the game" should not be making decisions that affect others. He discusses this idea in a variety of contexts, including politics, economics, and business.

From Individual Contributor to Manager

While being an individual contributor may provide more immediate and visible results, being a manager can offer a different type of value by leveraging your skills and experience to drive results through others. As a manager, you have the opportunity to influence the direction of the team and the organization, develop talent, and create a positive work environment that supports high performance.

How to cultivate "Skin in the Game"?

Remember that having "skin in the game" is not just about taking risks, but also about taking ownership, being accountable, and aligning your work with the broader goals of your team and company.

There are several ways you can strive to have "skin in the game" and increase your sense of ownership and responsibility:

  1. Understand the big picture: Gain a deep understanding of the overall goals and objectives of your team, department, and company. This includes understanding the product vision, customer needs, and business strategy. By aligning your work with the broader goals of the organization, you can better appreciate how your role contributes to the overall value delivered by your team.

  2. Understand the business, not just the engineering: Engineering Leaders are the bridge between all the functions that it takes to make a product successful (Product, Design, Communication, SRE et. al.). The role demands one to focus on all aspects of business, not just engineering. If done correctly, there's a strong potential to make a large impact. That is why there are many examples of EMs going on to lead both Product and Engineering in their Organizations.

  3. Empower your team: Create an environment where your team members feel empowered to make decisions and take ownership of their work. Foster a culture of accountability and trust, where team members have the autonomy to make meaningful contributions and take calculated risks.

  4. Take calculated risks: Embrace calculated risks and be willing to make decisions that may involve uncertainty or ambiguity. Take responsibility for the outcomes of those decisions and learn from both successes and failures.

  5. Solicit and act on feedback: Encourage open and honest feedback from your team, peers, and superiors. Listen actively, acknowledge shortcomings, and take action to improve. Continuously iterate and adapt your approach based on feedback to ensure that you are providing value as a leader.
    You can collect feedback through various channels - in your 1-1s, through the feedback tools in your Organization,

  6. Lead by example: Demonstrate a strong work ethic, commitment, and accountability in your own actions. Be willing to roll up your sleeves and work alongside your team to understand their challenges and provide support. Lead by example in embodying the values and behaviors you expect from your team.

  7. Foster a learning culture: Encourage continuous learning and development among your team members. Provide opportunities for skill-building, knowledge-sharing, and growth. Help your team members understand how their professional growth aligns with the team's and company's goals.

Take responsibility for setbacks. Give credit for successes.

By taking these steps, you can strive to have "skin in the game" as a software engineering manager, and actively contribute to the value delivered by your team and organization.

What if I still feel disconnected from this role?

If you feel that you are not providing value in your current role or if you miss the direct impact of being an individual contributor, it may be worth considering a transition back to a technical role. However, it is important to carefully consider your motivations and ensure that you are not simply seeking short-term gratification at the expense of long-term growth and career satisfaction.

It is important to reflect on what you enjoy doing, what you are good at, and what you want to achieve in your career, and make a decision that aligns with your values and aspirations.

Ultimately, the decision of whether to continue in a managerial role or transition back to an individual contributor role depends on your personal goals, strengths, and interests.


If you want to discuss further on this topic or others, I will be happy to connect and brainstorm.