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.
“Until managers take into account the systemic nature of their organizations, most of their efforts to improve their performance are doomed to failure.”
Dr. Russell Ackoff (thanks to Susanne Kaiser for the reference)
I came across this Twitter thread from Rein Henrichs, and I thought it had many good points about systems thinking and management.
A lot of managers, especially those from an engineering background, think that management is about doing stuff: defining rules, policies, and procedures; assigning tasks; creating external incentives; fixing problems.
It caused me to reflect a bit on my approach to systems thinking in the context of technical leadership.
One of the things that helped me the most as an engineering leader was developing a better understanding of systems thinking. When I (or others) use the analogy of “planting a garden” when setting up teams for success, this is what we mean. We are creating the system to enable groups and individuals to do their best work and then allow good behaviors (and results) to emerge. Of course, creating a system takes longer than pushing things down into the organization. Still, it produces more creativity and autonomy in the organization and makes it more resilient to change or challenges.
Managers who do not work with this understanding of systems think that management is purely about doing stuff: defining rules, policies, and procedures, assigning tasks, creating external incentives, and fixing problems. This “doing stuff” approach can produce good results in small teams or for a constrained about of time.
As Rein Henrichs also correctly points out, the act of building a system can be incomprehensible for others in the organization who are not directly involved (especially in other disciplines that are more transactional). This lack of understanding has often been my biggest challenge as a company’s senior engineering leader.
Building a system takes time. If you can get things to a good place where the system is starting to be self-perpetuating, the rest of the organization will see the improvements and become supporters.
Suppose the leadership team is impatient and doesn’t understand what you are trying to do. In that case, they will lean into the quick fixes listed above, namely re-organization or replacing individuals or trying to “drive accountability” through reductive top-down control mechanisms.
If that happens, you are stuck trying to mitigate the damage and build a longer-term plan to return to your original goals, but it is often a losing battle. The primary culture of the organization has re-asserted itself, and your chance to evolve it has mostly gone.
How do you avoid that fate?
Communicate! Make your plans clear in the hiring process, your initial days in the organization, and all along the process. Set realistic timelines for improvement and celebrate the successes along the way. When your peers are impatient, refocus them on the plan and the long-term gains you are working towards. Point to the achievements thus far and try to keep their “eyes on the prize.”
Will this always work?
No. It depends on the company’s situation and how much pressure there is on the leadership team. If the company is under stress, it might be better to refocus on shorter-term solutions that don’t actively detract from what you are trying to build.
My biggest successes in companies were getting the entire organization on board with the system I was working to build. Gaining support for a new systemic working is a culture change, and getting backing is contingent on the company wanting to change. If the company is on a “burning platform,” a situation where change is required for the company to grow or survive, you will find less resistance. A burning platform also provides the inspiration to persevere if the change is difficult.
My biggest failures trying to build systems were when I did not communicate my intentions clearly or did not get buy-in from the rest of the leadership team, or when I was not effective at communicating the improvements along the way.
Another challenge can be a change (losing a customer or a tough quarter) that puts pressure on the leadership team. In this case, you need to adapt quickly. Hopefully, the system you are putting in place encourages being nimble. You may need to pause the change to the system to focus on shorter-term tactical solutions. To minimize the disruption in the organization, be transparent about the need for the change, and set an expectation on how you will get reoriented towards your original vision afterward.
While there are many good books on systems thinking, the one I consistently recommend for engineering leaders is Management 3.0 by Jurgen Appelo. It isn’t just about systems thinking but weaves it into a broader book about management.
This article is the final in my series on valuable performance reviews. This article discusses how to deliver the review and salary news to your report.
This article is the final in my series on valuable performance reviews. The first part addressed preparing for the evaluation. The second part covered writing the assessment. The third part explained how to make a salary recommendation. Finally, this article discusses how to deliver the review and salary news to your report.
Each review discussion is one of the most important meetings in a person’s professional life. The primary goal of the meeting is as a milestone in a career journey. You will give the person an understanding of the progress they have made and insight into how they can get to the next stage of their career.
All the work preparing and writing the performance appraisal can go to waste by delivering the review poorly. I have always found the review conversation the most nerve-racking for me as a manager because that is where you see the effect of your (hopefully) well-considered analysis on the person. And people are… people. The conversation is always a bit awkward, given the stakes for the person receiving the review—but from there, it can go in many unexpected directions. I’ve had tense, combative conversations with people receiving a very positive review. Conversely, I’ve had a very unexpectedly genial and optimistic conversation with someone accepting a poor review. Even if you know the person well, the review conversation can be challenging.
Common advice is to give precise feedback to the people who report to you frequently during the year. If you do this, the review itself should not surprise them, as it would be consistent with what you have already said. However, while someone may have heard the feedback, it is another thing to see it written on a piece of paper with a review “score” (if your organization does that) and a salary adjustment connected to that feedback. Even if you are confident that nothing written in the review is new information, the person receiving it may not feel that way.
The best method I’ve found for having these discussions go smoothly is to come to the meeting prepared, give the person time to digest their review before the dialogue, and structure the conversation itself.
Preparing for the discussion
If you have followed the spirit of the process in the previous articles, you have assembled, organized, and interpreted a lot of data to write the review. This data is also helpful for your preparation and during the conversation itself. Having the information to explain things further if there are questions or disagreements is valuable. Their memory or interpretation of events is sometimes very different than yours or that of their peers.
Read over their review again. Make sure you have the data at hand to support the evaluation you wrote in case there are questions.
If you think the discussion might be tense, you may even want to rehearse the conversation in advance with another dev manager or someone from your company’s HR team. I sometimes rehearse challenging messages in the shower, looking for the right way to say something. You may also prepare positive messages to find the best way to say something without ambiguity.
Have empathy for the person receiving the review.
Think of the performance reviews you have received during your career. Both the good and bad. What made them stand out to you? Was it the review itself or the discussion (or lack thereof)? While the anticipation and the initial excitement of the evaluation are finding out about a promotion, raise, or bonus, and knowing that your hard work was recognized, the thing you will remember long after was the delivery of the information and the discussion that followed.
I’ve received at least fifty reviews since I started working. I don’t remember the numbers or most of the review scores. Still, I remember the manager who hadn’t put any thought into the process, the one who made promises review after review that they never kept, and the assessment where a manager made statements that were demonstrably false and, when shown evidence to the contrary, threw up their hands. I also remember the great conversations I had with the best managers I worked for that made me proud of what I had accomplished and excited about what more I could do (and how they would help me).
While you may be nervous about the conversation, the person you speak to is even more so. For you, it is the conversation that is scary. For them, it is the implications of the discussion on their livelihood. So come to the dialogue with that understanding and empathy for their position.
Give the person their review to read beforehand.
There is always the question of when to let the person read the actual document. Over the years, I have tried it three different ways:
Handing the person the review after sitting down to the discussion and letting them read it before speaking;
At the end of the review conversation, to read afterward; and
Giving the assessment to them the day before or the morning of the conversation.
The method that seems to work best is to give the person the assessment to review several hours before the review discussion, saving the actual numbers for the conversation.
When you give the person time to read and process the review document before the meeting, it allows them to prepare for the meeting. It takes some of the person’s concerns away because they know what to expect in the conversation itself, which makes the conversation less stressful for them. If they disagree with the assessment, it gives them time to prepare any argument/evidence they wish to present, making it feel less like an ambush. By sharing the review in advance, I have found that the conversation itself is often more substantive and valuable.
The review discussion
Start with a brief introduction.
While you both know why you are there, it is good to start the discussion with some of the broader contexts around the review process and anything around the company’s performance that will be relevant to the meeting (like a limited raise budget in a tough economic year). But, unfortunately, that broader context often gets lost in the review conversation itself, which can lead to confusion or misunderstandings.
If you’ve given the document to the person in advance, they will join the meeting with an idea of what to expect in the conversation. However, they will still be wondering about the salary numbers. While you may be talking about other things, until the person knows what their salary change is, they will wonder about it. To make the conversation more valuable, I like to share the salary change information or promotion early in the conversation. Once the person knows the most critical information they will receive, they can focus on the more extensive discussion about career development.
Discuss the document.
Discuss each section in the assessment together to make sure that there is a common understanding and agreement. Now is when you might share more details or data around your statements if needed. Do not just ask, “Do you agree with this section?” Instead, make sure they understand your comments, that you have answered any questions they have, and that they either concur with your assessment or at least appreciate your perspective and the data behind your conclusions.
Where to go from here?
If the review conversation is a checkpoint along a career, it is essential to help the person understand where the next checkpoint could be. It is vital in the review conversation to talk to the future and reflect on the past. Now is an excellent opportunity to give hope and support to someone who had a problematic review cycle or inspire someone who has been doing well to achieve even bigger goals.
Hopefully, you have been having regular discussions about the person’s career aspirations. The review discussion is the right time to confirm their goals and discuss how you can help them achieve them. What opportunities can you present to them that will help them grow professionally between this discussion and the next review discussion?
Be very careful about making promises that you can’t keep. There are many things beyond your control in the review process, like the raise budget, the stock pool, company performance, global economic situations, or a final promotions approval. Even if you had all those things within your control now, you might move on to a new role or new company by the time of the following review. If you make a promise and cannot keep it, you will demoralize the person and lose their trust. So choose your words carefully when talking about the future.
After the discussion
Within a few days of the discussion, write the person a note confirming any statements from the conversation, the answers to any questions you didn’t have during the dialogue, and the agreed-upon growth plan. If you have a shared agenda for your 1:1s or a list of topics to discuss, make sure that you regularly review any growth plans by adding them as a discussion topic.
Problem scenarios
What if the person disagrees with my assessment?
From time to time, someone will decide that your interpretation of the data is incorrect and, therefore, your review is wrong. When this happens, go over the person’s data you collected for the appraisal. If they have some information you didn’t receive in the process that causes you to reconsider, don’t promise them that you will change the review. Investigate the new information and if you want to change things, discuss it with your manager. This kind of late change rarely happens, however.
If they continue to refuse to accept your assessment, invite them to sit down with you, your manager, and a person from the people team to discuss it. You want the person’s concerns heard, but if they don’t have any new data, you also want someone in the conversation who will support you.
What if they want to negotiate a different raise?
People will occasionally believe that the salary discussion is a negotiation. I have heard that this is common in a few cultures, but it is not generally done that way. As I discussed in the previous article, the person’s new salary is arrived at as part of a long process, and there isn’t much—if any—flexibility by the time you are delivering the review to the person.
You generally can’t change their salary autonomously, so if you agree to reconsider and then you can’t change the number, you look ineffectual as their manager. Also, changing their salary will encourage others to try to negotiate in the salary review discussion (the word always gets around when something like this happens).
If someone is unhappy with their raise, discuss what they could do during the next review period to justify making a more significant raise recommendation. But, once again, don’t promise anything!
If someone was expecting an entirely unrealistic raise, you might want to share with them a bit about how the salary review process works and help them understand what normal looks like.
What if their friends at other companies got much larger raises?
Occasionally, in the salary review discussion, someone will tell you about their friend who got a 50% raise. They will also tell you about an article they read that says many companies are giving considerable raises to retain employees. Given how charged salaries are as a subject and how competitive the technology industry is for good talent, much disinformation about salaries is constantly circulating.
When faced with these stories, it is worth discussing your company’s salary benchmarking process. Help the person understand that there will always be outliers and unusual situations, but express that those are the exception and not the norm. It is also worth discussing the non-salary aspects of your company that make it an exciting place to work. Companies often look to salary as their only employee retention tool when it is hard to retain employees because of their culture, lack of growth opportunities, or uninteresting projects.
If you’ve been regularly giving feedback, you’ve prepared for writing the review, and you’ve prepared for the review conversation, it will almost always go well.
In this article, I talk about the many ways the review discussion can go wrong because that can make the whole process scary for many people. It is good to be prepared for the conversation to go in a challenging direction. However, if you have been open with people about their performance and regularly given them feedback, and you talk to them about how you will help them improve their performance, the tough conversations are few and far between.
I usually end the performance review process proud of what each person has achieved and excited about helping them reach their potential. That is my hope for you as well.
