On Building Transferable Skills
The Importance of Abstracting your Skills into Generic Playbooks
Dear Readers,
2025 is in full swing, many of we are deep into the reality of things, balancing between aspirations and constraints of life. Q1 ending marks a perfect time to check on our progress in our 2025 goals. As I reflect on my journey in the last 3 months, navigating through re-org uncertainties and staffing surprises, I came to realize the importance of building transferable skills. Whether you are an engineer or a manager, whether you work in infrastructure teams or product teams, an important aspect of building experiences is to abstract them into “patterns” of problem solving playbooks that you can take with you to places. In this post, I am going to share my thought process in this space. Hopefully you find it helpful!
Abstraction is the Name of the Game
As knowledge workers, we solve problems day in and day out. A manager could be faced with tough prioritization decisions, or designing north star metrics and counter metrics to measure the process towards our goals. An engineer would be dealing with mounting technical debts and the inability to innovate systematically while under the pressure to pursuit short-term wins. As you solve for these challenges, how to “abstract“ them into generic playbooks that you can “pattern match” later? Let’s dive into this with one specific example: the prioritization of engineering items. In my mind, a generic playbook is composed of the following 5 components:
Context: A key component of the abstraction is the context of the problem you are solving. For instance, you realized our team is buried in mounting technical debts eroding its ability to innovate. This resulted from years of investments in feature delivery and lack of emphasis on engineering betterments. Yes your team shipped quite a bit! New product capabilities are rolled out every quarter, with maintenance tasks taking the back seat. Quite a normal phenomena for teams in hyper-growth mode where all problems can be solved by more headcount, and hell ya more code! But in 2025, this is no longer the case. We are in the territory of efficiency and optimization.
Problem Definition: Now that we understand the context of this challenge, the problem becomes: how to design our engineering roadmap and prioritize our engineering items in a structured way? How to set up the team for long-term success and create rooms for systemic innovation that will enable future growth of the business? How to slow down and invest in needed platform capabilities so we can accelerate over the long run? This becomes a prioritization question.
Strategy: So how to achieve this? We need extreme clarity on the product vision and strategy (which informs the direction of the business), as well as engineering strategy (which informs the north star vision of our architecture and systems). Equipped with vision and strategy, you are set to use risk and reward based frameworks to translate the strategy into sequences of milestones that will then determine your team’s roadmap.
Success Criteria: Well, this is a tough one. Because per Goodhart’s Law below,
When a measure becomes a target, it ceases to become a good measure.
- Charles Goodhart, British Economist
metrics can be gamed! If you are not carefully with designing the right metrics to define Success Criteria, you might be incentivizing behaviors that will solely focus on the metrics, losing sight of the original goal. In our example, if you design the success criteria as “spend at least 40% of our team capacity on KTLO“, you will incentivize doing KTLO just for the sake of it, instead of the original goal of “reduce technical debt and engineering risks to accelerate innovation in the long run”. How to avoid gamification of metrics? In general, you mitigate this by using a combination of indicators instead of a single metrics. Some teams define “metrics“ and “counter metrics“ to keep things in check. It is the manager’s responsibility to devise the right incentive structures to promote desired behaviors.
Ongoing Audits: And yes, we also need ongoing updates to your “playbook” based on the feedback from real-world implementations. Maybe you prioritized your engineering roadmap items using a structured framework, only to be thrown away due to a Sev0 incident that changed everything. How do you budget for escalations in your engineering roadmap? Regular auditing and updating your playbook to keep it up to date is a valuable exercise.
Be Aware of Limitations of your Abstractions!
A lot of leaders coming to a new organization would immediately apply learnings from their previous organizations on the new job, hoping to make a quick impact. It is a temptation. What worked previously must continue to work, correct?! Well not so fast! Abstractions are, by definition, layers removed from the reality, and has its own operating constraints. Whenever you apply an abstraction, be aware of the limitations and the context of your playbook to see if it would apply in the new environment. For instance, while bigger companies have process heavy cultures to protect “bottom line“ business and what has worked, smaller businesses could embrace more of “ship fast and break things“ mindset to find PMF quickly. Your playbook for addressing tech debts should be tailored, and contextualized to the environment.
Transferable Skills Take you to Places
As you build your transferable skills via abstractions and general playbooks, you will start to see stories of your career forming in your eyes. What type of problems have you solved in the past? How did you solve it? What were the outcomes? How would you paint the arc of your career? As you think through these questions, you will develop the narrative of your career. And it makes the infamous career question of “do I leave or stay?” easy. Nikhil Singhal in his “The Skip” podcast summarized it well: stay if your story is improving in the next 6 months ( that you are building new playbooks or updating existing ones via learning), stay. Otherwise, leave. Whatever your decision, building transferable skills will take you to places that you never imagined before. Until then, happy learning!
