After years of mentoring dozens of engineers (and helping get quite a few of them promoted), I’ve developed a collection of concepts and metaphors that consistently resonate with my mentees. These are the lessons I find myself returning to time and again—mental models that help navigate complex technical careers and organizational dynamics. While each engineering journey is unique, these principles have proven valuable across various situations and career stages. Hope this helps!

Do the Thing, Don’t Just Sell the Thing. Credibility comes from accomplishment, not self-promotion. When evaluating advice or leadership, look beyond titles and rhetoric to actual achievements. Some people speak convincingly about engineering practices they’ve never successfully implemented. Trust those who demonstrate mastery through results rather than those who merely claim expertise through position or persuasive communication.

Grow the Ladder: Don’t Just Climb It. Success in engineering isn’t about competing for scarce positions at the top—it’s about expanding the structure itself. Think of career advancement as a pyramid: as you look upward, opportunities naturally narrow with fewer senior positions available. Rather than solely focusing on climbing this fixed structure, direct energy toward growing the ladder by creating new domains, expanding responsibilities, and developing new areas of expertise beneath your current position. By broadening the foundation—adding new teams, initiatives, or technical domains you oversee—you create room for your own advancement without waiting for limited openings above. This approach transforms career growth from a zero-sum competition into an expansive journey where you create your next position rather than just competing for existing ones.

Chess: Plan Six Steps Ahead. Engineering careers, like chess, reward strategic thinking beyond that next move. The best decisions aren’t necessarily those that solve today’s problem, but those that position you advantageously for future challenges. Consider how your current technical decisions, skill development, or project choices will affect your position several moves ahead. This mindset helps you make decisions with long-term payoffs rather than short-term conveniences.

The Socratic Method: Keep Asking Why. Continuous questioning is your most powerful tool for uncovering truth and driving to solutions. When faced with proposals, problems, or decisions, persistently asking “why” cuts through surface-level explanations to reveal core issues. If your questions make others uncomfortable or nervous, you’re often on the right track—valuable insights frequently hide behind those moments of tension. This approach directly supports Amazon’s Leadership Principle of “Dive Deep,” but must be executed with respect and genuine curiosity. Don’t abandon your line of questioning just because it creates discomfort; instead, acknowledge the discomfort while firmly continuing your inquiry. The most important discoveries frequently emerge when people become hesitant to continue answering, as that’s where unexamined assumptions and critical gaps in reasoning typically reside.

Go Deep to Influence Wide. Developing profound expertise in a specific area creates a foundation for broader impact. When you understand something deeply—whether it’s a technology stack, domain knowledge, or methodology—you gain credibility that extends your influence beyond that specialty. This depth allows you to make connections others miss and contribute meaningfully to discussions outside your immediate focus. Once established as an expert (say, in DynamoDB data models), use this credibility to gradually expand into adjacent territories. You’ll find yourself invited to design reviews where your specific expertise is needed, creating opportunities to thoughtfully extend your influence to neighboring domains. Charlie Munger says it best - “Extreme specialization is the way to succeed.”

Poker Hands: Play What You’re Dealt. Your career, like poker, involves both skill and luck. Sometimes you’ll face unfavorable conditions—difficult projects, challenging teams, or market downturns. Other times, you’ll have advantages. What distinguishes great engineers isn’t getting consecutive “good hands,” but maximizing opportunities when they arise and minimizing damage during challenging periods. Focus on playing your cards well rather than lamenting not having better ones.

Spin the Wheel: Strategic Deep Dives. You can’t scrutinize everything, but random, thorough examinations of work keep everyone accountable. By occasionally but unpredictably diving deep into specific areas, you maintain quality across the board without micromanaging. This creates a positive pressure that elevates standards throughout the team, as no one knows which aspect might receive detailed attention next.

Avoiding Local Minima: Disagree and Commit. Sometimes compromises produces worse outcomes than picking either original proposal. If option A scores 10 points and option B scores 9, a compromised AB worth only 1 point is worse than either original idea and doing nothing is worth 0 points. Recognize when to stop debating and commit to a good-enough solution—even if it’s not your preference—rather than allowing analysis paralysis or creating an ineffective hybrid approach.

Conway’s Law and Organizational Structure. Organizations tend to produce systems that mirror their communication structures. While this is descriptively accurate, great engineers think beyond these constraints. Design the right solution first, then adapt implementation to organizational realities. This approach prevents sub-optimal architectures that merely reflect reporting lines rather than technical needs.

Two Business Styles: Incumbent vs. Startup. Understanding whether your organization operates with an incumbent mindset (optimizing existing processes) or a startup approach (setting trends) helps align your contributions appropriately. Incumbents thrive by executing established processes more efficiently than competitors. Startups succeed by anticipating industry needs and creating solutions before demand fully materializes. Recognize which environment you’re in and adjust your thinking accordingly.