Most engineering leaders inherit organizations they didn’t design. By the time we step into a role, the structure is already there: a mix of teams, reporting lines, and legacy decisions. It’s easy to accept that structure as “just the way it is.”
But structure quietly shapes everything. It defines how information flows, how decisions get made, how accountability works, and how fast (or slow) a company can move. The org chart isn’t just a management artifact; it’s a piece of system design.
Over the years, I’ve learned that organizational design is one of the most potent tools a technology leader has, and one of the least understood. You can’t manage around a broken structure any more than you can code around a broken architecture.
Inheriting the System
I’ve only had a few chances to design an organization from scratch, usually in early-stage startups. More often, I’ve inherited something that had evolved over time. Some were the result of thoughtful planning. Others grew like weeds.
Every organization reflects its history. Even the most ad-hoc structure is an artifact of past decisions: who talked to whom, what problems needed solving, what crises shaped the company.
That’s Conway’s Law in action: organizations design systems that mirror their communication structures. Look closely at a product’s architecture and you’ll see its org chart.
In the product engineering organization I led at Adobe, my teams were arranged by function: one group focused on building the backend, while others managed clients, core libraries, and infrastructure. This was the standard team structure at the time, but it limited our speed. Each feature had to go through four different teams, each operating on its own sprint cycle. As a result, it could take months to ship a simple feature because it needed to pass through each layer of the teams.
When I joined Spotify, the structure was entirely different. Autonomous, cross-functional squads owned features end-to-end. They deployed independently and moved fast. The system’s modularity came directly from the team design.
Different problems, different structures. Both logical in their contexts, but the lesson is constant: you ship your org chart.
Designing for Purpose, Not Precedent
Too many companies treat organizational design like a template. Someone says, “Let’s use two-pizza teams like Amazon,” or “Let’s adopt the Spotify model.” The intent is fine, but the context is missing.
Amazon and Spotify built those systems because they fit their culture, strategy, and scale. Copying the form without understanding the function is like cloning another company’s codebase without knowing its dependencies.
The real question isn’t “what structure should we have?” It’s “what problem are we solving, and what design will align our teams to solve it?”
Structure is strategy made visible. A good design aligns incentives, communication patterns, and ownership boundaries with your goals. It creates high-bandwidth communication where you need it and separation where you don’t.
And it has to evolve. The organization that works for a 20-person startup will break at 100. The one that works at 500 will creak at 2,000. Like software architecture, organizational design is never finished.
Diagnosing What’s Broken
You don’t redesign an organization because it’s old. You redesign it because something isn’t working.
My favorite diagnostic tool is simple: follow the work.
Take one feature or story and trace it from idea to production. How many teams does it touch? How many handoffs? How long does it sit idle?
Every delay is a clue. Sometimes it’s a resourcing issue. Sometimes it’s a missing skill in a team. But often, it reveals deeper misalignments: unclear ownership, too many dependencies, too little trust.
At Adobe, that exercise made the bottlenecks obvious. Each feature touched four teams in sequence, and a “simple” change could take three months due to the handoffs. At Spotify, where squads owned the full stack, the team shipped the same kind of work in a single sprint. It wasn’t magic. It was designed.
If you want to understand why your organization feels slow, follow the work.
Stream-aligned teams own a product or flow of work end-to-end.
Enabling teams help others improve tools or skills.
Complicated subsystem teams handle specialized areas of expertise.
Platform teams create shared systems that reduce cognitive load.
They also describe three ways teams interact: collaborate closely for a time, provide something as a service, or facilitate learning.
The value isn’t in the framework itself; it’s in the vocabulary. It helps leaders think about flow instead of hierarchy and design structures that reduce friction instead of adding layers.
When I read Team Topologies, I recognized much of what we’d already been doing at Spotify; the authors had spent some time at the company. But I also saw patterns from earlier roles that suddenly made sense in hindsight. The book doesn’t prescribe. It clarifies.
Common Patterns and Traps
Most organizations follow predictable patterns as they grow.
Functional silos work early but become brittle later. They make coordination explicit but slow.
Cross-functional teams increase autonomy and speed but come with a higher cost. At Spotify, that meant hiring more mobile developers than most companies would ever consider. It worked because the company optimized for velocity over constraining headcount.
Centralized data or infrastructure teams start strong, then evolve into bottlenecks. You have to anticipate when to distribute those capabilities.
Matrix organizations can preserve continuity and reduce disruption when people change teams, but they also add complexity quickly. They work best when accountability is crystal clear.
And then there’s the most common anti-pattern: designing around personalities. Building an org around one person’s strengths, or avoiding their weaknesses, might seem practical in the short term. It always becomes debt later.
Reorgs as Refactors
When a structure stops working, treat the reorg like a refactor, not a revolution.
Don’t blow everything up. Make small, deliberate changes. Be transparent about what you’re solving and how you’ll measure success. Make the problems you are trying to solve clear, and how you will handle the case where the structure change doesn’t solve them.
The biggest mistake leaders make is reorganizing at people instead of with them. Change feels arbitrary when the reasoning is hidden. If people understand the problem, they’ll accept the solution even if they don’t love it.
Every reorg has a sociotechnical cost. You’re not just moving boxes. You’re changing relationships, communication paths, and identity. Handle it with clarity and care.
Reorgs should feel like system refactors, not revolutions.
Leading by Design
Organizational design isn’t a one-time project. It’s an ongoing act of leadership.
Start by mapping your current system: who talks to whom, where decisions stall, and where ownership is ambiguous. Align the structure with your strategy and your culture.
Design for clear interfaces between teams and between roles. Iterate carefully, explain your reasoning, and gather feedback.
The structure that got you here probably won’t get you where you need to go—and that’s okay. Good organizations, like good architectures, evolve.
If you drew your company not as boxes and lines in a directed acyclic graph, but as flows of information and work, what would it look like? Where would the friction be? Where would it hum?
That picture, not the official org chart, but a system diagram, is the authentic architecture you’re building every day.
A practical guide to recognizing, protecting, and finding the right organizational culture
In this post, I’m revisiting a keynote I gave in 2013 at the BBC Developer Conference, titled “Building a Strong Engineering Culture.” Twelve years later, my thinking has both stayed the same and evolved. I want to discuss culture, not just for engineering teams, but for you as an individual, as a manager, and as someone seeking your next role.
What Actually Is Culture?
Culture’s a heavy word. We use it in many contexts, including company culture, engineering culture, and team culture. But what does it really mean?
Henrik Kniberg, whom I had the immense pleasure of working with at Spotify, distilled it beautifully:
“Culture is the stuff people do without noticing it.”
My definition is more formal: Culture is the manifestation of the shared values of the organization as represented by the actions of its members.
The key words here are values and actions. It’s not what you say, it’s what you do. And to Henrik’s point, it’s what you do without even thinking about it.
Real Values vs. Aspirational Values
Every company I’ve worked at has had its values spelled out somewhere. The problem? Many companies have publicly stated values that aren’t really their values. These are what I call ‘aspirational values’ – they are the values the company wishes to have or believes it should have, but they may not necessarily reflect the actual behaviors and beliefs of the employees.
“Can an employee say no to a decision from a superior on the grounds that it violates a core value?”
If your company has a core value of honesty to customers, and your boss tells you to lie to a customer, could you say, “I’m sorry, I can’t do that. That doesn’t align with our core values”? And would your boss fire you, give you a poor review, or say, “I don’t care, do it anyway”? If so, it’s not actually a core value.
Think about what the real values of your company are. Not the stated values, the real ones. In companies where the stated and real values matched, those values would become shorthand. Someone would say “That wouldn’t be aligned to [value]” in a meeting, and it would just end the discussion. No disagreement, no argument.
Another way to think about this: if your team shares an office, where’s the thermostat set? Has everyone determined the temperature that they agree on? A new person enters, tries to change it, and somebody says, ‘Whoa, no. This is the temperature we work at.’ That’s a shared value in action. It’s not an important one, but it’s the same principle for how you approach coding or organize your work. This is a simple example of how shared values can manifest in everyday actions, from the way you dress to the way you communicate.
The Flow: Values -> Culture -> Everything Else
Your values create the basis of the culture. The culture then influences everything else:
Processes: How work gets done, or how you account for vacation time, and expenses.
Artifacts: Physical things like signs, swag, and how offices are decorated. At Microsoft, receiving the “Ship It” award upon shipping your product was a significant achievement. It reinforced the core value of delivering value to customers.
Rituals: Company and team meetings, how you celebrate, or how you bring teams together.
Beliefs: What you believe about the industry, about product development, and building successful companies.
Why Culture Matters
You’ve probably heard the quote attributed to Peter Drucker: “Culture eats strategy for breakfast.” I agree with the general sentiment, but I’ve seen plenty of companies with great cultures that struggled as businesses, as well as successful companies with punishing cultures. Patty McCord, former head of HR at Netflix, said it better: “Culture enables success, but it does not cause success.” A great culture helps you go faster, happier, and healthier. While an amazing culture alone won’t guarantee success, it will make things a lot harder without it.
Protecting and Reinforcing Your Culture
If you have a good culture, you need to protect it. Your culture and values must inform every process and framework that guides the company’s operations. Otherwise, you’re creating conflict within the organization between what you say and what you do. If you reward something other than the culture, the culture will shift to the behaviors and values that you reward.
Start With Your Career Ladder
I get particularly frustrated when companies adopt another company’s career ladder. You’re two different companies with two different cultures! Hopefully, that other company designed its ladder to support its values. If your values aren’t aligned with theirs (they aren’t), you’ll start promoting, hiring, and rewarding based on another company’s values.
Build your own career ladder based on your values. It’s a tremendous first artifact because it informs everything else, from how many levels you have (which affects promotion frequency) to the expectations at each level.
Hiring Is Critical
Who you hire either supports or hurts the culture you have. I don’t suggest requiring “perfect” alignment or becoming a monoculture; you need diversity of thought. However, if you have a core value of collaboration and you hire someone who prefers to work alone, dislikes collaboration, and produces good work independently, you have problems.
One: they’ll be unhappy because people keep wanting to collaborate. Two: if they stay and receive raises or promotions, it sends a strong signal that collaboration isn’t actually a core value. Three: if they end up in interview loops, they will be looking for people like them due to similarity bias, which will accentuate the problem.
Onboarding Matters
You can’t simply throw new hires into a team and expect them to pick up the culture. At Spotify, when someone joined, they would spend a sprint with all the people who joined on the same day, plus a few experienced Spotify folks: an agile coach, a development lead, and a product manager. They would build features together and ship them. They would learn why the company did things in a specific way.
Because those new joiners would end up in different parts of the organization, they’d reinforce and refresh that cultural understanding. If a team started to drift, they’d help steer it back.
This intro sprint was also an excellent opportunity to identify if someone wasn’t aligned with the company values. Better to know in the first sprint than months later.
Performance Reviews and Firing
When deciding an employee’s performance as a manager, your reference isn’t other employees; it’s the rubric, the career ladder. What are they supposed to be doing? What is the expectation at this career step? You’re comparing them against the rubric because your culture and values inform the rubric.
If you don’t use that as the yardstick, you start promoting or giving raises based on something else. People notice. I’ve heard “My friend in another team got promoted and they’re way worse than me, so why am I not getting promoted?” more times than I can count. That usually means management is not being consistent.
Can you make hiring mistakes? Absolutely. When it becomes apparent that someone isn’t aligned, even if they’re fun to be around and do adequate work, they will erode your culture. You have to make a decision. It’s better to move them along where, honestly, they’ll be happier. If you aren’t aligned with your company’s culture, it’s not a happy place for you.
Team Culture vs. Company Culture
I used to think Microsoft had a broken culture. I spent eight years there. I was happy for about one or two of those. But the problem was that I wasn’t well aligned with Microsoft’s culture. Nothing was wrong with Microsoft; I wasn’t a good fit for the company culture.
I tried to make my team work the way I wanted the company to work. I convinced my management to let me build a team and use extreme programming to deliver a feature. The project was incredibly successful. When I went back and said, “Look, it worked, can we do more?” my boss said, “You’re absolutely right, it worked better than we expected. However, no, we’re not going to do that anymore because that’s not the way the company works.”
He was right. That wasn’t who Microsoft was. I wanted to turn the company into the place I wanted to be, but that wasn’t what the company wanted.
If you’re hoping your team can change the dominant culture, good luck. It’s unlikely, especially in larger organizations. It isn’t impossible, but it’s very, very difficult.
I had a different experience at Adobe. Adobe was open to change, not fixed in its mindset. When I worked on a lean, startup-like project there and succeeded, Adobe rewarded that success rather than saying, “Wow, that was great, we’re never doing it again.” Adobe had a core value (stated or not) of being open to change. That was much in line with who I am, and I was very happy there.
When Culture Shifts
Culture isn’t fixed. It will evolve with the company and its employees, sometimes slowly, sometimes quickly.
Slow, Organic Change
Organic change happens naturally. Companies grow, expand into new markets, and hire new employees. Over time, the culture will change to incorporate the new shared values and new processes required to support the larger entity. That’s okay if you’ve been careful in your hiring to ensure that new hires align with the company’s core values.
If the company’s core values are genuine, they will endure as the company doubles in size, becomes public, or changes its funding models. The culture may shift slightly, but what makes the company the company — the culture — stays consistent.
Fast, Disruptive Change
Fast cultural change occurs when a company is acquired or when the board brings in a new CEO. An acquiring company may have no interest in your culture; they’re buying you for financial or business reasons. Your processes will change to align with them, you’ll inherit their career ladder (and thus their values).
Or a new CEO comes in and says, “This is crazy, we can’t run a company this way,” and starts making changes based on their values. This change is often a deliberate choice from the board to “shake up” a company, or because the board is unaligned with the company’s values.
You often see this in startups. They hire a C-level person from Meta or Amazon, and that person starts implementing things from their prior company because that’s what they know works. An Amazon person says, “We need six-page memos for all meetings because that worked well at Amazon.” It does work at Amazon. Will it always work at your company? No.
You can hire talented individuals from these companies; they have great people there. You need those who are open-minded, who understand their experience was for that environment, and who ask, “How do I take what I learned and apply it in this new context?”
When rapid cultural change occurs, you’re either going to be pleased about it or not. If you’re unhappy, complaining or fighting the change is not a good use of your time. If you’re open-minded and don’t actively hate it, try it out. You might learn new skills or approaches. But if you’re unhappy and unaligned, why are you staying?
There’s a quote from Shanley Kane: “Broken cultures break people.”
Finding a Culturally Aligned Company
If you’re looking for a new job, it’s essential to determine if a company aligns with your values. First, you have to know your own values. What’s important to you? What are your must-haves versus nice-to-haves?
Then develop questions you can ask your interviewers. Ask about what happens when the company is under pressure. What happens when revenue is short for a quarter? What happens when a product is late? If you’re in B2B, what happens when a customer is about to churn? When a company or its leadership is under pressure, that’s when its true values are revealed.
I once joined a company where the CEO told me great stories about fixing broken cultures and the great culture he wanted to build. The team was terrific and shared many of my values, as well as the stated values of the CEO. But when the startup hit a rough patch, we started violating those stated values one by one. When I said, “I’m not going to do what you’re asking because that’s not who we say we are,” and the response was, “I need you to do it anyway,” I knew it wasn’t the right place for me after all.
So, ask for examples of stressful situations and how they affected the company’s operations and processes. If the person you are speaking to can provide concrete examples of how they reacted under stress in ways that align with their stated values, that’s a sign that they are genuine core values.
Final Thoughts
I loved working at Spotify. It’s the best job I’ve ever had. Why? The stated values were the actual values. They weren’t aspirational. That’s one reason I took the risk of moving my family to another continent to work there.
My experience with Adobe was very similar. The core values and culture of both companies were incredibly aligned with my personal values. Not only did that make me a happy employee, but it also made me a successful one, as I naturally worked in a way that was aligned with my peers and management.
Am I happy at my current company? Yes, I am. Because my values align closely with the company’s actual values. Will I be happy forever? It will depend on how the culture evolves.
I hope your company’s values align with yours. If they aren’t, I hope you’re in a position to influence the culture or find a place that’s better aligned with your values. It’s worth paying attention to. It’s worth being aware of. It’s essential to consider this, especially if you’re aiming for professional growth. If the company isn’t aligned with your values, you might learn the wrong things.
Crafting a resume as a technology leader is about more than listing roles—it’s about showcasing achievements, leadership, and strategic impact. Learn how to tailor your resume, highlight cross-disciplinary management, and leverage tools like LinkedIn and personal websites to stand out for executive roles.
A common discussion with people I mentor is how to properly structure a resume or Curriculum Vitae. It comes up often enough that I felt compelled to write about it last year: “Sweat the details on your resume, especially if you are a developer or technology leader.” In the last few weeks, I have reviewed multiple resumes from folks hoping to achieve a director-level or above role. I wanted to share some lessons on how an executive-level resume differs from others in Technology.
As a technology executive, your resume is your calling card—a teaser trailer for your professional achievements. Crafting a resume that highlights your leadership journey while demonstrating value is an art form, particularly as you aim for senior roles like VP, CTO, or similar. Here are key takeaways and strategies to ensure your resume stands out.
Tailor Your Resume for the Role
Your resume isn’t a one-size-fits-all document. Different audiences—recruiters, hiring managers, or automated systems—expect varying levels of detail. To make a strong impression:
Create multiple versions of your resume:
Short-form (2 pages or less): Use this for recruiters or direct submissions. Focus on succinct highlights that convey your biggest achievements and relevant experience.
Comprehensive (full-length): Maintain this detailed record for Applicant Tracking Systems (ATS) or contexts where exhaustive experience matters, such as certain consulting or academic roles.
Use strategic brevity: Each version should prioritize accomplishments and impact over exhaustive lists of tasks or skills. At the bottom of the short-form resume, include a URL to your full-length resume, LinkedIn profile, or personal website for those who want more detail.
Tailor content to the role: If applying to a startup, focus on entrepreneurial accomplishments. For a multinational corporation, emphasize experience working with large teams or global operations.
Focus on Achievements, Not Responsibilities
Leadership resumes should emphasize measurable outcomes rather than generic responsibilities. This allows you to demonstrate value and differentiate yourself from other candidates. Consider these approaches:
Use metrics whenever possible: Quantify your achievements to provide concrete proof of your impact. For example:
Replace “Managed a team of data scientists” with “Grew a data science team from 5 to 20 members, delivering a 10x cost efficiency improvement in critical business processes.”
Instead of “Improved system performance,” say, “Increased platform uptime from 97% to 99.9% while reducing hosting costs by $500,000 annually.”
Highlight transformative initiatives: If you drove major changes—like adopting a new technology stack or transitioning a team to a new operating model—emphasize these innovations and their outcomes.
Demonstrate multi-disciplinary management: Showcase examples where you’ve managed diverse teams or disciplines, such as engineering, product, and design. For example, “Led cross-functional teams spanning software development, UX design, and data analytics to deliver a platform used by over 10 million users.”
Put Your Most Recent Role First
Your current or most recent position carries the most weight. It’s likely the first thing a recruiter or hiring manager will read, so ensure it captures attention:
Make it prominent: Place this role on the first page and dedicate the most space to it.
Emphasize scope and results: Clearly articulate the scale of your responsibilities, such as budget size, team size, and direct impact on the company.
Focus on strategic leadership: Highlight initiatives you spearheaded and the outcomes they achieved, particularly those demonstrating thought leadership, cross-functional collaboration, or innovation.
Save earlier roles for subsequent pages, reducing detail as you go further back in time. Roles older than 10 years may only need a line or two unless they’re particularly relevant.
Position Skills Strategically
Technical skills are critical, but how you present them matters:
Avoid generic lists: Instead of placing a large block of skills at the top, embed them within descriptions of your achievements. For example:
“Led migration to AWS Cloud, saving $1.2M annually and achieving 99.9% uptime.”
Highlight relevant expertise: Tailor the skills you emphasize to the role you’re applying for. If you’re aiming for a director role in AI, showcase experiences involving ML frameworks and tools like TensorFlow or PyTorch.
Subtly include soft skills: While technical skills are important, leadership roles often require strong interpersonal and strategic abilities. Show how you led teams, resolved conflicts, or drove cross-departmental alignment.
Summarize Career Progression
Rapid promotions and career growth can be a powerful selling point, but they need to be presented succinctly:
Highlight trajectory: For example, “Promoted from Senior Machine Learning Engineer to Head of AI within three years.”
Simplify titles: If your roles had incremental changes, summarize them into a cohesive narrative. For example: “Advanced from Senior Engineer to Director of Engineering over six years, culminating in leading a 50-person team and delivering $20M in annual revenue growth.”
Emphasize leadership: Show how your roles evolved to include greater responsibility, larger teams, or more strategic initiatives.
Cut the Fluff
Hiring managers and recruiters skim resumes. Get to the point by removing irrelevant or overly detailed information. This will make your resume more focused and efficient, ensuring that only the most important details are highlighted.
Avoid generic claims: Statements like “Proven leader” or “Results-oriented professional” don’t add value. Instead, provide examples that demonstrate these qualities.
Skip common experiences: Transitioning to remote work during COVID-19 isn’t unique. Focus on outcomes that set you apart.
Reduce early-career details: Unless highly relevant, roles from over 10 years ago should only include titles and dates.
Use LinkedIn and a Personal Website for Depth
Your LinkedIn profile and personal website can complement your resumé by providing additional details and ensuring you’re findable by recruiters:
LinkedIn:
Include all positions and significant accomplishments.
Add media or links to showcase notable projects, talks, or publications.
Use keywords strategically to improve searchability for specific roles.
Personal website:
A personal website can be a dynamic portfolio, host your detailed resume, and provide links to your projects, publications, or conference talks.
Organize your website by sections, such as Leadership Roles, Key Achievements, and Speaking Engagements, to make it easy for recruiters to navigate.
Use your website to expand on areas that wouldn’t fit in a resume or LinkedIn profile, like detailed case studies or thought leadership pieces.
Think Like a Hiring Manager
Your resume should:
Reflect strategic thinking: Tailor information to the audience and highlight your ability to align your work with organizational goals. This approach will make your resume more strategic and thoughtful, resonating with the hiring manager’s perspective.
Demonstrate leadership: Showcase your leadership skills by using examples of team management, cross-functional collaboration, or strategic initiatives. This will make your resume more confident and assertive and reflect your leadership potential.
Inspire curiosity: Provide just enough detail to make recruiters and hiring managers want to know more about you.
Remember, the goal of your resume is to secure a conversation—not to answer every question upfront.
Advice for Aspiring Executives: Breaking Into Leadership Roles
If you’re seeking your first executive-level (Director or above) role, your resume needs to convey readiness and potential:
Reframe your achievements: Highlight instances where you took on responsibilities beyond your official role, such as:
Leading cross-functional initiatives.
Mentoring junior staff or peers.
Driving strategy or innovation.
Show leadership impact: Even if your title doesn’t reflect it, focus on achievements that demonstrate leadership qualities, such as:
“Initiated and led a company-wide migration to DevOps practices, reducing deployment time by 80%.”
“Mentored three engineers who were later promoted to senior positions.”
Emphasize thought leadership: Include speaking engagements, publications, or significant contributions to open-source projects to showcase your influence in the field.
Network strategically: Your resume is only part of the equation. Attend industry events, contribute to discussions on platforms like LinkedIn, and seek mentorship from executives who can provide guidance and referrals.
Communicate readiness in your summary: Begin your resume with a compelling summary that positions you as an emerging leader. For example:
“Engineering Manager with a proven track record of driving strategic initiatives and leading high-performing teams, seeking a Director role to deliver innovative solutions at scale.”
Breaking into executive roles requires showcasing your potential and articulating how your experience aligns with leadership expectations. By tailoring your resume and approach, you can make the leap into senior management.
By taking a strategic, minimalist approach to your resume, you’ll showcase your accomplishments and demonstrate your ability to communicate effectively—a critical skill for any technology leader.
I’m thrilled for this year because I am publishing my first book! This is the work of three (or twelve, depending on how you count it) years. The book, “It Depends: Writing on Technology Leadership 2012-2022,” includes content from this blog and articles originally published elsewhere. I took all those articles, cleaned up the grammar, edited for clarity, and organized them into themes and logical progression. This is something that I’ve been meaning to do for a while, and it took me longer than I expected to finish it, but I’m proud of the result.
The book will be released by Unit Circle Press in March. More information about pre-ordering will be available soon. I also just finished recording the audiobook version, which should be available around the same time.
I’ve also launched two new projects to support the book’s launch. A newsletter and a podcast. I will be serializing the book in the newsletter and serializing the audiobook in the podcast. Both will feature extra content like answers to your questions and additional context around the chapters. The first newsletter and podcast episode are now available. They are both free! Please subscribe to the newsletter and subscribe to the podcast on Spotify, Apple, Google, Amazon or wherever you get your podcasts!
Please check out the book website for more information.
We often hear about empathy as a singular concept—a soft skill, an essential quality of being human that connects us to others. But empathy comes in two flavors. It has shades, and understanding them might make us better humans.
We often hear about empathy as a singular concept—a soft skill, an essential quality of being human that connects us to others. But empathy comes in two flavors. It has shades, and understanding them might make us better humans.
Two Sides of the Same Coin: Logical and Emotional Empathy
– Emotional Empathy: This is the classic definition of empathy that most of us are familiar with. It’s feeling what another person feels. If your friend is sad, you feel sad. If they’re excited, you feel their joy. Emotional empathy happens almost instinctively. It’s raw and visceral.
– Logical Empathy: This form is more calculated. It’s understanding what another person feels without necessarily feeling it yourself. It’s more about perception, awareness, and insight. It’s about seeing things from their perspective, even if you don’t feel their viewpoint.
Emotional empathy might be more natural for some people. You know the type, those who can feel a room’s mood as tangibly as a physical touch. I’ve always admired that, but it wasn’t me.
And then there are others for whom logical empathy might be more innate. These individuals are perceptive, analytical, and capable of seeing a situation from various angles without becoming emotionally entangled. Many of us who make our careers in technology are attracted to the industry because we have these skills.
Learning the wrong lessons early
Most of my first jobs were at large companies with very competitive and hierarchical cultures: IBM, Silicon Graphics, and Microsoft. Microsoft in the 1990s was legendary for its’ hyper-competitive culture. I worked there for eight years. Microsoft taught me that I had to expect that other teams were constantly looking for how to undermine mine and that every outstretched hand was likely masking a knife held in the other hand behind the back. I eventually realized that the environment was a bad fit for me, but sadly, I didn’t get out until I had internalized those lessons.
After Microsoft, I sought out more collaborative environments, but I struggled. I constantly expected ill intent behind every action from a peer. I knew that this was hurting me and that I needed to move to a mindset of expecting positive intent from others, but I didn’t know how to rewire my brain.
A Splash of Insight: David Foster Wallace’s “This is Water”
My epiphany came when someone recommended that I read David Foster Wallace’s commencement address to Kenyon College, “This is Water.” If you haven’t read or listened to it, it’s enlightening. Wallace talks about default settings, the unconscious, automatic ways we interpret everything around us. He speaks about learning to think more compassionately and understanding that everyone around you has a unique inner life full of dreams, fears, and struggles. And it’s not always about feeling their pain; sometimes, it’s about understanding their pain.
Wallace’s speech was a masterclass in logical empathy. And it gave me a better way to try and understand others’ intents, especially when you don’t know someone well.
Developing Logical Empathy When Emotional Empathy Feels Unnatural
So how can you foster logical empathy if emotional empathy doesn’t come naturally to you? Here’s a roadmap:
Listen More, Talk Less: You don’t have to feel what someone else feels to understand them. Listen actively, engage with their words, and seek to understand their perspective.
Ask Questions: If you don’t understand something, ask. Asking not only clarifies but demonstrates that you are engaged and interested in the other person’s perspective.
Seek to Understand Their Context: What could be the pressures on them that they may not be vocalizing? If you are talking to a salesperson near the end of the quota, could they be pressured to make their quota? Is the Product Manager being held to unrealistic expectations by their boss? Leverage what you know about the business or organization to understand what subtexts may be unsaid.
Reflect: Spend time thinking about the perspectives of others. Consider why they feel the way they do. Analyze their thoughts without judgment.
Use Imagination: Try to visualize the scenario from their perspective. This mental exercise helps in understanding without feeling.
Practice Compassion: Logical empathy may not be instinctive, but it’s still a form of compassion. Approach situations and people with an open heart, even if it’s an analytical one.
Embracing Both Forms
The truth is logical and emotional empathy are not mutually exclusive. You can be someone who mainly engages with logical empathy while still having the capacity for emotional empathy and vice versa.
The real beauty lies in embracing both and recognizing that there’s no right or wrong way to connect with others. It’s a journey, and it’s one worth taking, regardless of where you naturally fall on the empathy spectrum.
In our complex and diverse world, empathy in all its shades is more than a desirable trait; it’s a necessity. Understanding how you relate to others and working on enhancing that connection, be it through emotional or logical empathy, makes you not only a better colleague, friend, or partner but a more complete human being.
This exploration of empathy, fostered by wise words from thinkers like David Foster Wallace, has been a personal awakening. It’s water, and now I see it.
In our professional lives, growth is a constant pursuit, not merely for our development but also for the organizations we represent. We’re all learning all the time, albeit in different ways and at varying paces. In nurturing an employee’s growth within a role, two approaches frequently come to the fore: mentoring and coaching. While both are powerful tools, they serve different purposes and are best applied in specific contexts – sometimes, we need a guide, and sometimes we need a goal-oriented strategist.
Choosing the Right Approach: Context is Key
“Coaching is for performance. Mentoring is for potential.”
The choice between coaching and mentoring hinges on the context. Here are some hypothetical situations to illustrate this.
Consider an employee who is a subject-matter expert, consistently delivering quality work but struggling to make presentations to stakeholders. In this case, a coach could help the employee improve their communication and public speaking skills, with clear, measurable objectives for their progression.
In contrast, imagine a new recruit with immense potential but little experience in the industry. With their wealth of experience and industry knowledge, a mentor could provide this newcomer with invaluable insights about the sector and career development advice, supporting their long-term growth.
When explaining the difference, I often contrast these roles by saying, “With mentoring, I will give you my opinion. With coaching, I will ask you the questions necessary for you to form your own approach with my guidance.”
The mentoring approach works better for more experienced professionals expanding their skills to new areas. The coaching approach is better for someone who needs to deepen their skills in an existing area. Coaching is also effective when helping someone in an area where you don’t have as much direct experience. You can leverage your experience in other areas to help the person figure out the answer themselves.
Be explicit in your choice of method
Know if you are taking a coaching stance or a mentoring stance when helping someone. That does not mean you can’t give advice when coaching or ask prompting questions when mentoring. It means you and the person you are working with understand how you will approach the interaction. It sets the tone and expectations.
“Mentoring and coaching are not an ‘either-or’ proposition but a ‘both-and’ necessity.”
While mentoring and coaching have unique strengths, it’s essential to recognize that both are integral to fostering a growth culture in an organization. The mentor-mentee relationship builds a knowledge-sharing culture, and coaching empowers individuals with specific skills to excel in their roles.
In our pursuit of growth, remember that we’re not merely ticking off a checklist. We are on a journey that requires us to understand when to take the scenic route of mentoring, appreciating the broader view of the professional landscape, or when to go straight ahead with coaching, focusing on the immediate roadblocks ahead.
Remember to share your insights and experiences as you continue on this journey. We are all co-travelers in this quest for growth and learning; every insight contributes to the collective wisdom.
In this Shane Hastie, Lead Editor for Culture & Methods, spoke to Phil Abernathy about his work helping organizations focus on employee happiness to drive customer happiness and shareholder return and the Bureaucracy Mass Index as a tool to identify where companies are bloated and ineffective. He also spoke about what’s needed for real transformation.
Great practical advice on building happier teams and a tool to measure bureaucracy in an organization.
Tony and Mark – supported by a global community of technologists, enthusiasts, and dreamers – brought 3D to the brand-new Web with VRML. This episode features Owen Rowley, Neil Redding, Linda Jacobson, Brian Behlendorf, John McCrea, Coco Conn — and Neal Stephenson.
With all the talk (and investment) in the metaverse, it is frustrating sometimes that people forget that the technology industry has been thinking and working on this for decades. Tony and Mark were instrumental in creating VRML, and I appreciate them documenting some of the history, but I was a bit disappointed that they omitted some of the other folks that were involved in the beginning.
Stated purpose: to unlock the potential of human creativity—by giving a million creative artists the opportunity to live off their art and billions of fans the opportunity to enjoy and be inspired by it.
Spotify is the most popular streaming service in the world, with 188 million people paying for premium subscriptions and hundreds of millions more listening for free on the ad supported tier. Which is why it has been called the world’s best place to get noticed as a musician. But getting noticed and making a living are two different things. In this episode we decide if Spotify is more about “Honesty” or “Little Lies?”. Listen in to find out.
One of our board members at Anaconda turned me onto this podcast. It’s about purpose-driven companies that don’t live up to their professed goals. This episode focuses on Spotify but also talks about the broader streaming music economy.
A16z Podcast – Creators, Creativity, and Technology with Bob Iger
A wide-ranging conversation with Bob Iger on the interplay between technology, content, and distribution; as well as Bob’s journey — and that of various creators! — especially as the industry evolved from TV and cable to the advent of the internet/ web 1.0 to 2.0 to briefly touching on web3 and other emerging technologies. As well as topics top of mind for all company and community builders: from build vs. buy and the innovator’s dilemma, to managing creativity, decentralization, remote work, and much more.
I didn’t expect to like this podcast as much as I did. I appreciated it not only for his takes on leading teams of creative people but also for his business acumen and for getting more details about creative people I admire and their work.
20VC – 20 Product: Marty Cagan on The Four Questions of Great Product Management, Product Lessons from Marc Andreessen, Ben Horowitz and eBay’s Pierre Omidyar & The Difference Between Truly Great Product Teams and the Rest
Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for some of the most successful companies in the world, including Hewlett-Packard, Netscape Communications, and eBay. He worked directly alongside Marc Andreesen and Ben Horowitz at Netscape and Pierre Omidyar at eBay.
I was not a fan of Cagan’s book Inspired. I called it “Ayn Rand for Product Managers.” I worked with some product managers who were all huge fans of it, and the result was not great for working with engineering.
In the time since, I have appreciated what Cagan said in his blog, which was a lot more focused on Lean-style product development and cross-functional collaborative teams. This podcast was further evidence for me that I need to re-evaluate how I see Cagan. I appreciated his perspective.
Planet Money – Episode 576: When Women Stopped Coding
Mark Zuckerberg. Bill Gates. Steve Jobs. Most of the big names in technology are men.
But a lot of computing pioneers, the ones who programmed the first digital computers, were women. And for decades, the number of women in computer science was growing.
But in 1984, something changed. The number of women in computer science flattened, and then plunged.
Today on the show, what was going on in 1984 that made so many women give up on computer science? We unravel a modern mystery in the U.S. labor force.
This podcast was oddly personal for me. It talks about how advertising and culture perpetuated a vision of computers as being for boys, discouraging women from entering the computing field. This was the time that I became fascinated by computers. I remember the ads, tv shows, and movies they discuss, and when I entered college for Computer Science my class was 70 men and 2 women. They also talk about my alma mater Carnegie Mellon and the steps that they have taken to address this imbalance.
It is amazing how quickly culture changed computing from being a female-dominated field to being a male one and then how long it has taken us to try and bring it back into some sort of equilibrium.
In the last post, I shared the books that I found worth recommending that I read in 2022. The next post shares podcasts that I found valuable. In this (longer) post, I will share links to the blog posts from 2022 that I think are recommendation worthy. I’ve broken it into sections based on content.
As a CTO, I spend a lot of my time thinking about building effective technology organizations, and I’m always looking for new approaches or lessons in the space.
The pandemic has caused nearly two years of collective trauma. Many people are near a breaking point.
An airplane passenger is accused of attacking a flight attendant and breaking bones in her face. Three New York City tourists assaulted a restaurant host who…
If you are wondering why people are such jerks now…
Learn about the How HashiCorp Works project and why there are links to internal HashiCorp materials in this article. Our…
I like the movement in making how companies work transparent. It is useful to read as a leader and a great recruiting tool for those companies. I always wonder how much reality matches the shared documents. If you know you will share with the public, you are likely to be a bit more aspirational than actual, but it is still useful to read.
Medium sees more employee exits after CEO publishes ‘culture memo’ – TechCrunch
The sign that Netflix’s culture had irreversibly started to…
The genius of Netflix as an employer was that it has always been very upfront about who it is and how it works, with the understanding that anyone taking a job there knows what they are getting into. This works great until the culture starts to change, so this isn’t about an individual employee being unhappy. It will be interesting to see how Netflix navigates this (or doesn’t).
Culture as a Product: How HubSpot Built its Famed Startup Culture
Around Boston and beyond, HubSpot is known for its strong entrepreneurial culture . The company has received many awards over the years and was recently named…
Hubspot is an interesting company. Having read Disrupted (https://www.amazon.com/Disrupted-Dan-Lyons/dp/0316306096) I am a bit skeptical of how they talk about themselves, but of course, one always should be. That said, even if the public face of companies’ cultures is more aspirational than real, there is still something to be learned. I didn’t decide that the 37 Signals books were worthless because when under stress, the company didn’t live the values they proclaimed.
Bolt Loaned Employees Thousands to Buy Stock—Then Laid Them Off
The challenge of startup options is that employees rarely are allowed to sell them. When a startup has been around a long time, and startup options are starting to expire, but employees have had the liquidity event necessary to have ready cash to exercise their options, what are they to do? A company I was in also considered a loan program for employees but decided it was potentially problematic. Bolt learned that lesson the hard way, and their former employees are worse off for it.
A big 32-hour workweek test is underway. Supporters think it could help productivity
This article was originally written for LeadDev . In tech, we talk a lot about failing fast: implementing small, incremental…
I talk a lot about failure, failing fast, etc… This article is an actual case study in how to recover when your team has a big failure. I always like real-life stories instead of vague opinion pieces.
Career Development: What It Really Means to be a Manager, Director, or VP
It’s no secret that I’m not a fan of big-company HR practices. I’m more of the First Break all the Rules type. Despite my general skepticism of many standard…
There are tons of posts and books about being a line manager. There are substantially less about levels beyond that. I’m always looking for informative articles or books about more senior leadership levels. This was a decent one.
There is a euphemism in rocketry often heard at SpaceX – Rapid Unscheduled Disassembly. A catastrophic explosion, in other words. Until now, it was not…
The speed of Elon’s decline from “genius who can see a better future and bring it about” to “asshole snake oil salesman with a narcissistic personality disorder” was sudden by any measure. How do we keep people like this from ruining our favorite apps/sites? By keeping ownership and infrastructure distributed…
Remote Work/Return to the office
For the last couple of years, the push and pull of remote vs hybrid vs back-in-the-office has been a major story in the work press. I’ve already made my decision that I’m going to keep working remote and will choose companies that allow me to do that, but in all of this discussion I’m also looking to understand how other companies are approaching things.
Why workers are calling BS on leaders about returning to the office
This may be losing some of its value as it ages, but speaking as an all-remote company CTO, if you don’t listen to your employees about how they want to work, I’ll be happy to take them off your hands.
The Future of Work Isn’t Fancy Tech. It’s Remote Work and Smarter Management
The remote/office debate is dying down any time soon. There is more pressure on returning to offices now, but there is also more resistance. Given the layoffs, employees may not feel empowered to resist the call to return to the office, so maybe that will gain ground.
The Worst Part of Working From Home Is Now Haunting Reopened Offices
Few people are as knee-deep in our work-related anxieties and sticky office politics…
If a primary driver for bringing people back to the office is better collaboration, you may want to consider how your hybrid remote/office system is set up.
How to embrace asynchronous communication for remote work
How to get started with async GitLab believes that…
The secret to successful remote work (especially if the team is spread across time zones) is moving to be asynchronous first. The companies that have been distributed for long periods and have scaled have embraced this, but it is harder than it seems, and many companies struggle. Even those that have always been distributed. This GitLab guide is very helpful.
Web Technologies
I spent much of 2022 learning more about WebAssembly as we launched PyScript at Anaconda. I think that it has some amazing potential and is one of the most important technologies of the last few years.
This article explains the concepts behind how WebAssembly works including its goals, the problems it solves, and how it runs inside the web…
If you are in technology, you need to understand WebAssembly and how it can be used. It can potentially be more transformative than many of the technologies we depend on for software development today.
A short history of Flash & the forgotten Flash Website movement (when websites were “the new emerging artform”)
This post is a transcript of a talk I gave at UCSC. Thank you for inviting me! I’m sharing it here because It’s a GOOD summary of the history of a technology…
If you were active on the web in the 90s and early 2000s, you will remember the explosion of massively creative web experiences propelled by the Macromedia/Adobe technology Flash. While you can still create those kinds of experiences using modern web technologies, it now requires a level of coding expertise that puts the programmers in the driver’s seat instead of the artist/designer and requires a team instead of a single creative person.
The genius of Flash was that it made complex interactivity and visuals easy for many artists to create, and the result was beautiful chaos. The web is just a bit more boring for the death of Flash.
Spotify’s grand plan to monetize its open source Backstage project via premium plugins
Backstage was created when I was at Spotify. Even in its earliest days, it solved many problems for us in a massively micro-service architecture. It’s cool to see how it has developed over the years, and it was also cool to see that Spotify had open-sourced it. I think it is interesting that Spotify is doing this experiment, but also disappointed because I know of at least one company formed by ex-Spotifiers that were trying to build companies on top of Backstage.
Google: The Model Your Site Was Built On Is No Longer Feasible
Hours before Elon Musk closed his deal to buy Twitter, he published an open letter to advertisers. Musk knew that big companies, in particular, were anxious about…
“Free speech” and an advertising-based revenue model are incompatible.
Web3/Decentralized Web/Metaverse
When blockchain emerged, I spent some effort to really understand it. Then I realized that it was a technology searching for a use case fueling a tulip-like baseless speculative market. When Web3 started to emerge, I delayed judgment until I could understand it better. While I believe that there are people who believe that it can fuel a world where creators have more ways to be paid for their work and other such lofty goals, the practicality of it is that very little of those schemes require the blockchain, and most of the people in the space are just trying to make a quick buck before the tulip market collapses.
You’ll probably hear the fuzzy term web3 bandied about in the press if you read tech journalism. Sprinkled around, all these articles are all manner of…
The title says it all.
Crypto and Twitter Are Imploding at the Same Time and It Is Glorious
I’ve been on Mastodon since 2017, but my usage really increased since the acquisition of Twitter. There have been a lot of stories talking about how people are abandoning Mastodon, but even if it doesn’t become what Twitter was, it is still a vibrant community.
There’s No Fixing Meta’s Metaverse, Scrap It, Start Over
I spent 6 years working on the metaverse at Microsoft during the 90s. While the technology has drastically improved, the reason we didn’t get the metaverse back then is that no one could figure out something to do in the metaverse except shoot each other or have sex with each other. All the folks working on metaverse now have learned nothing from the multiple generations of attempts that preceded them. There is still a smug belief that “if you build it, they will come.” The problem is that there is still nothing to do once they show up.
If these problems are intrinsically linked to consolidated tech giants like Meta, Google, and Amazon, why not embrace technologies that decentralize power? This has become a key issue for Brewster Kahle, the 61-year-old founder of the Internet Archive…
Having participated in various forums and working groups for decentralized web stuff over the last few decades, I’m consistently excited by the possibilities and enthusiasm of the folks who work towards those goals and disappointed by their naivete about what people are willing to put up with and how commercial entities are incentivized to coopt and pollute the technologies that do gain some momentum.
Your organization should run its own Mastodon server
Whether you are a large company, a political party, an international news agency, an NGO or a government institution, you should seriously consider running your…
What is the point of having a decentralized web if you don’t own your own part of it?
Twitter Turmoil: We Need an Open Protocol for Public Discourse
Do we want to stay on a social network that shows such callous disregard for its own people? That is the question many of us have been asking as news hit this…
All the agility has been sucked out of agile projects Doing agile is not the same as being agile Agile projects have become bloated, lazy waterfall projects…
One of my biggest pet peeves is people deciding that a bad experience they had with a poorly implemented framework or process must mean that that framework or process is clearly bad and that anyone who had a good experience is lying. So many of the “I was involved in a poorly run agile project and so agile must all be a lie” or “my company tried to do the Spotify model, and it didn’t work; therefore, it must not work at Spotify either” type posts just show the ignorance of their authors and nothing else. While I was worried this article was just another one of those, the author is concerned more about poor agile processes and not agile itself. He even gives some good advice. So worth a read.
Machine Learning
Mozrt, a Deep Learning Recommendation System Empowering Walmart Store Associates with a Personalized Learning Experience
We developed Mozrt, a deep learning recommendation system for Walmart Academy App, the training content portal for Walmart store and Supply Chain associates.
Walmart built a massive technology team in its fight with Amazon. It is good to see them sharing their work.
ChatGPT and the Google and Microsoft chatbots get all the attention now, but before that was GPT3, which also remains the only LLM with the ability to train on your own corpora.
Building Communities
Why Communities Are the New Business Currency | HackerNoon
We’re no longer content with one-way interactions with businesses. We want to feel like…
If you can’t tell from the previous post, I spent some time updating myself on building virtual communities last year. This is a good starting place for folks looking to understand the value.
It needs to be said again, perhaps this time more strongly. Your Blog is The Engine of Community . Dammit. Blog More You are not blogging enough.…
Scott Hanselman thinks developers should be blogging more, and when they do blog, it should be on their own platforms. And he’s right.
Music Industry
I’ve been involved in music as a musician, radio DJ, label owner, and streaming software creator since I was 15. I was delighted to rejoin the music industry in December when I took on the role of CTO at DistroKid.
With 100K tracks uploaded a day, a longtail music cull is coming – Hypebot
Lucian Grainge doesn’t like that people aren’t listening to Universal Artists as much, so he’s putting pressure on the streaming services to remove content he doesn’t think is good. The problem is deciding what content is good and what content is bad. Streamers already remove fraudulent content. So, who decides if your band shouldn’t be on Spotify because you might take a stream away from Justin Bieber (who himself was discovered because he uploaded his songs to YouTube). Gatekeepers are all about protecting their interests at the cost of innovation and getting others a shot.
Why Amazon VP Steve Boom just made the entire music catalog free with Prime
It’s never been clear how much Amazon cares about music streaming as a business. It’s always been an also-ran in the streaming wars that only has listeners because it is an add-on to Prime and is the default service with Alexa. Amazon hasn’t invested much in the service, but maybe that is changing now…
I’d like to share some of the things related to technology, leadership, or management that I found particularly instructive. There was plenty of other good stuff, but these were the ones that stood out.
After making a concerted effort to write more in 2021, my blogging in 2022 fell off a cliff. I hope to be better this year, but while I wasn’t writing as much, I was still reading, watching, and listening. I’d like to share some of the things related to technology, leadership, or management that I found particularly instructive. There was plenty of other good stuff, but these were the ones that stood out. These are not affiliate links. I don’t get any kickback for recommending them.
You probably didn’t need me to recommend this book to you, because it is one of the classics of technology leadership. In fact, this isn’t the first time I’ve read it. I hadn’t read it for many years, and picking it up again, I was surprised at how relevant and valuable it still is. If you haven’t read it, it is a very easy read.
The Art of Community: Seven Principles for Belonging
This book isn’t specific to technology; it is about building inclusive communities of any type. It is valuable for people leaders in that it talks about the necessary parts of belonging to any group. It is focused more on communities of choice instead of work communities, but the insights are the same. As someone who has also spent a lot of time building online communities, it is extremely relevant for that as well.
This isn’t a leadership or management book, but it is a book about living intentionally, and I found it valuable on multiple levels. As it was a New York Times bestseller, you didn’t need me to recommend it to you either, but I will say that I personally appreciate the author and his message.
The Business of Belonging: How to Make Community your Competitive Advantage
This book is about building online communities for companies. It has overlap with the Art of Community book, but it is much more practical and meant for people who do this for a living. I found it a bit introductory, but it had some good ways of articulating specific points that I will reuse. If you are new to this space, it is a great introduction.
The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter
Another classic of management that I had read before but reread as I prepared for my new role at DistroKid. Once again, it had been a long time since I had read it, and I was struck by how practical and true its advice was. I realized that when onboarding to previous roles, the companies where I started off the best were when I followed its advice deliberately or intuitively.
Lead Together: The Bold, Brave, Intentional Path to Scaling Your Business
This is either a book you will read and find yourself nodding along with, or a book that you will read and throw down in disgust after the first couple of chapters. It is a semi-practical guide about how to be more inclusive in your leadership. For those who have read Fredrick Laloux’s Reinventing Organizations and are trying to figure out how to move their company towards Teal, this book will be useful. For those who are tired of being in a top-down organization or are constantly accused of being a micro-manager, this book is worth toughing out even if you don’t agree with all of their suggestions because it will give you choices and ideas that will help you grow as a leader.
