know how your org works (or how to become a more effective engineer)

The Mirage of Aspiration

Know How Your Org Works

  • exactly what technical skill you need to invest effort into getting better at that will actually be rewarded
  • how to build lasting relationships with other people on your team or organization that will ultimately dictate the success of a project
  • how to effectively pitch projects or improvements and see these through to completion
  • how to navigate ambiguity
  • how to manage conflicting priorities or expectations
  • how to best deal with setbacks
  • how to weigh the pros and cons of technical choices in the larger context of the organizational realities and needs
  • how to identify and drive quick wins
  • how to discern what’s achievable in precisely what time frame
  • how to use this knowledge to judiciously pick battles
  • and in the worst case, to know when to cut your losses and quit

Soft Skills Are Hard Skills

  • how best to gather information you’re missing
  • how and when to get by without doing so

Understand Implicit Hierarchies

  • Understand the implicit organizational hierarchy
  • Identify the people who wield undue influence and their way of thinking and general philosophies (by either talking to them, or other people in the organization, or researching their past work, reading any articles or blog posts they might have written, or talks they might have presented, etc.)
  • Identify how the aforementioned philosophies have been previously successfully applied to projects and teams they were on. Why were these efforts considered successful? What were the problems these philosophies solved, and what were the problems they didn’t solve (or exacerbated)?
  • How do you build credibility with them? Can you lean on your past work? Your subject matter expertise? Your previous track record? Is there someone they trust and respect who can vouch for you, for them to take a leap of faith and agree to do things “your” way?

Cultures: Top-Down, Bottom-Up, and Both

  • Are you on the same wavelength as them? Do you both attach the same salience to the problem in question? If not, are you up to the task of impressing upon them the importance and urgency of the problem?
  • Is there some information or knowledge they have (and you don’t) that informs their thinking on the matter? How best can you get this information?
  • Do you both share the same view of the opportunity cost?
  • What are their implicit and explicit biases? What are their blind spots? Can you use some of these to your advantage?
  • What are the things they generally value? What kind of work or behavior impresses them?
  • Is there any specific abstraction or process or methodology they are particularly attached to? Can you lean in on these to more effectively market your opinion to them?
  • What’s the timeline they are comfortable working with to solve the problem? A month? A perf cycle? Many years?
  • What’s your personal level of trust with them? Will they go to bat for you?
  • What does “success” mean to them, and how do they measure it? How have they typically measured it for work that’s in-progress?
  • How do they typically handle setbacks? Have you drawn up contingency plans and discussed it with them?
  • How do they handle failure? Do they assume any responsibility for it, or will you be scapegoated (and possibly fired)?
  • Do they have a culture of blameless postmortems for large-scale team or organizational failures? Are these lessons shared and discussed transparently with everyone on the team and in the organization?
  • What is their previous experience working with partner teams or organizations?
  • Have they been burned badly in the past working with another organization or another team?
  • What’s their organizational reputation? Are they well-liked? Well-respected?
  • How conflict-averse (or not) are they?
  • How do you build consensus amongst your peers when there’s no top-down decision making authority?
  • How do you break down barriers between different peers?
  • How do conflicts get resolved if there’s no higher authority to mediate? Does it boil down to nitty-gritty quantitative details like metrics, or something more nebulous such as “likeability”?
  • If all key ideas have to originate from the bottom, which ones makes it to the top? How has this worked in the past?
  • Can “code” solve all issues? Can you go prototype an idea you have and then successfully pitch it? Does your team or organization empower you to do this during your business hours, or are you willing to spend your nights and weekends pursuing this goal?
  • Has the problem you’re trying to solve been attempted before? How did that attempt go? What were the failures? Do you understand the proximate cause of these failures? Are you sure you won’t run into the same issues again?
  • What’s the opportunity cost? Can you convince your peers that it’s worth solving right away if it hasn’t been prioritized so far?
  • What’s your scope of influence? Does it extend to just your team, your team and sister teams, or your entire org? Are people outside your team willing to give your solution a whirl?
  • How do you convince different people or teams with different incentives? Is this something you can even do without top-down support?
  • How do you ensure adoption, especially cross-organizational adoption?
  • How do you enlist partners or advocates for your effort? Are there other teams ready to adopt your solution, if you were just to build it, and advocate for it?
  • Do you have key relationships with the stakeholders? Do they trust you? If not, why not? And how would you go about building this trust?
  • How do you convince your peers who’ve had previous bad experiences with your team or project in the past?
  • How do you build credibility?
  • How do you motivate and incentivize your peers in general?
  • What’s the cost of failure? Just one fair to middling perf cycle, or something worse? Who’ll be impacted? Just you? Or your entire team?
  • What are the cultural problems you perceive? In a bottom-up setting where there’s no higher authority that can mandate teams to change how they work, how do culture problems get fixed?

Get comfortable with the “mess”

  • how to gather just the right amount of information to get on with your task
  • how not to get too caught up in the weeds unless required
  • how to read a lot of code at a fast clip and come away with a reasonably good mental model of what it’s trying to do
  • how to come up with hypothesis and use a variety of general purpose techniques and tools to validate the hypothesis
  • how to reproduce bugs quickly without elaborate local configurations and setups
  • and more.
  • varying levels of skill and ability to deliver on their promises
  • varying (sometimes even opposing) incentives and reward structures
  • varying appetites for risk or change
  • varying philosophical views on software development and systems
  • varying levels of tolerance for failure
  • varying willingness to make investments (in people and projects) with a long-term view in mind

Look For Small (And Any) Wins

Understand Org Constraints and Manage Your Expectations


  • good at solving pressing problems
  • relentlessly getting things done
  • successfully creating change than just endlessly talking about the need to do so




@copyconstruct on Twitter. views expressed on this blog are solely mine, not those of present or past employers.

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Cindy Sridharan

Cindy Sridharan

@copyconstruct on Twitter. views expressed on this blog are solely mine, not those of present or past employers.

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