Strategies to Stay Competitive and Interview-Ready During Extended Job Searches
Making the Most of an Unplanned Career Break
The tech industry continues to face challenging times, with layoffs affecting professionals at all levels of the industry. If you’re currently between roles, whether it’s been three months, six months, or longer, you’re not alone. Unfortunately, there’s still a perception that extended unemployment reflects poorly on the individual rather than industry conditions. Here’s how to turn an unplanned career break into a strategic advantage while preparing compelling stories for your next interview.
Reframe Your Career Break
I often see people list “career break” to cover a gap between roles. While people do this as a deliberate choice to recharge, you can also use this on your resume to reframe an extended job search. Simply listing “career break” on your resume isn’t enough. Be specific about what you’re doing with that time. Are you learning new technologies? Earning certifications? Developing new skills? This shows you’re staying engaged with industry developments and taking your professional growth seriously, even while job searching.
More importantly, each skill you develop gives you fresh material for interviews. When interviewers ask about recent learning or how you stay current with technology trends, you’ll have concrete examples: “During my career break, I dove deep into Kubernetes and earned my CKA certification. I also built a personal project using React 18’s new concurrent features to understand how they improve user experience.”
If you’re using “career break” to account for job search time, limit this approach to six months maximum unless you’re genuinely taking an extended, planned break. You can use the end of your “career break” time on your resume as an opportunity to restart your job hunt, looking fresh to recruiters.
Start a Consulting Company
Creating a consultancy demonstrates you’re still actively working and using your skills, even if you’re not employed full-time. Yes, building a consultancy is challenging, especially without strong existing connections, but it shows initiative and keeps you in the professional game.
In interviews, consulting experience provides rich storytelling opportunities. You can discuss how you navigated different client needs, adapted to various tech stacks, or solved problems with limited resources. “Working with three different clients taught me to assess legacy systems and propose pragmatic modernization strategies quickly” is far more compelling than explaining a gap in employment.
Be strategic about the contracts you accept, ensuring you can transition away if a full-time opportunity arises. Use any downtime between clients to develop new skills or pursue certifications that enhance your value proposition and give you additional interview talking points.
Build a Startup
Don’t let the complexity intimidate you; starting a startup can be as simple as developing an idea and creating a website. This approach works particularly well for senior leaders who want to demonstrate they’re still innovating and building.
The interview advantages here are enormous. When someone asks, “Tell me about your startup,” you have a natural opportunity to showcase technical decisions, product thinking, and problem-solving approaches. You can explain why you chose certain technologies, how you validated assumptions, what you learned about user experience, or how you approached scaling challenges. These conversations demonstrate both technical depth and business acumen.
Most startups fail, and hiring managers understand this. What they’ll appreciate is your initiative, the skills you’ve developed, and the concrete experiences you can discuss. Be prepared to explain your transition: “After eight months, I realized the market timing wasn’t right, but I learned invaluable lessons about modern deployment strategies and user research that I’m excited to bring to a larger team.”
Address the obvious question directly: “I’m ready to shelve the startup and focus entirely on this role. The experience taught me what I love about building products within a larger organization rather than going it alone.”
Contribute to Open Source Projects
Open source contribution keeps you coding, collaborating with teams, and engaging with the broader tech community. As a significant user of open source software, contributing back is both professionally beneficial and ethically sound.
This path creates specific technical stories for interviews. You can discuss code review processes, how you approached complex bug fixes, or how you collaborated with maintainers across time zones. “I contributed a performance optimization to [popular library] that reduced memory usage by 30%” is a concrete achievement that demonstrates both technical skill and impact.
While “open source contributor” might not carry the same weight as other options on your resume, it’s meaningful work that demonstrates ongoing skill development. Plus, becoming a key contributor to a popular project can lead to networking opportunities and potential job connections.
Volunteer Your Technical Skills
Consider leveraging your expertise for charitable organizations that need technical support. Many nonprofits struggle with outdated systems, a lack of digital infrastructure, or limited technical resources. Volunteering your skills provides several benefits:
Real-world impact: You’re solving genuine problems for organizations, making a difference
Portfolio building: These projects often involve diverse technical challenges and constraints
Interview gold: “I built a volunteer management system for a local food bank that increased their efficiency by 40%” shows both technical capability and values alignment
Leadership stories: Smaller organizations often give you more responsibility, providing examples of how you drive technical decisions and manage stakeholder relationships
Problem-solving under constraints: Nonprofit projects typically involve limited budgets and resources, showcasing your ability to deliver value with creative solutions
When discussing volunteer work in interviews, focus on the technical challenges and business impact rather than just the charitable aspect. “Working with a limited hosting budget taught me to optimize for performance in ways I hadn’t considered in enterprise environments.”
Strategic Interview Messaging
Whatever approach you choose, be prepared to explain your transition back to full-time employment confidently. Frame your experience as intentional professional development: “I used this time to explore entrepreneurship and deepen my technical skills. Now I’m excited to bring these fresh perspectives and enhanced capabilities to a collaborative team environment.”
Each path gives you concrete examples of continued growth, problem-solving ability, and professional commitment. The key is having specific stories ready that demonstrate how your career break time made you a stronger candidate, not someone who’s been out of the game.
Remember, showing that you’ve remained productive and engaged during your career break demonstrates resilience, self-motivation, and commitment to your profession; qualities any employer would value. More importantly, you’ll walk into interviews with fresh experiences and genuine enthusiasm for what you’ve learned and built.
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.
At least once a month, someone in a 1:1 or a mentoring session will ask me why I write these articles or give talks at conferences and want to know how they could get started themselves.
It can be daunting if you’ve never published something with your name attached or spoken in front of a group of your peers. The most common fear I hear is that people are afraid that they “have nothing to say” or relatively nothing to say that is new.
I give everyone the same advice.
You are the only person in the world that has your experiences. If you tell your story, no one will have heard it before.
A talk on Typescript would be interesting to more people than you might think, but a talk on your experience using Typescript for the first time and the things you learned as part of that experience will be interesting to nearly everyone, even if they aren’t interested in Typescript itself. Every software developer has had the experience of using a new language on a project. Experienced Typescript developers are interested in the problems people new to the language face. People interested in learning Typescript will be interested in your experience. You have something to say that people will want to hear!
If you are worried about writing about something for fear that you will say something wrong and be called out for it, no one can correct you about your own experiences. If you want to give a talk but are worried that someone in the audience will contradict you, it’s important to remember that by being the person standing on the stage giving the talk, people will assume that you know what you are talking about.
While putting yourself out into the world can be scary, reminding yourself of the above may help you overcome that fear. Remembering that you can build up your experience in many small ways is also key. Very few people have their first public speaking experience in front of hundreds of people or have their first blog post go viral (for the wrong reasons).
Why do I write and talk?
Every person will have their reasons for wanting to share their knowledge publicly. I have several reasons why I choose to.
To share knowledge
Over the decades, I’ve gained a lot of hard-won knowledge and learned a lot from others who have been generous with their wisdom. I try to share what I’ve learned with my teams and the people I mentor, but widely sharing knowledge takes a long time. Posting and giving talks is a faster way of sharing the lessons I’ve learned.
To save time
In my mentoring, I often find myself repeating the same advice over and over. That will frequently prompt the subject of a new blog post or talk (such as this one). As a benefit of posting it somewhere, I can refer someone to it for more information. It helps me save some time in a conversation. If a person has already read the post or seen the talk, we can focus on the specifics of their issue and get deeper faster.
To understand something better by explaining it to others
Writing a post or talk also allows me to crystallize my thoughts on a subject. So often, we come to a way of doing things over time and don’t consider why we do things that way or how we came to our approach. Writing out how I approach a subject helps me understand myself and why I do things. My decisions became much more deliberate once I started blogging and talking.
Employer Branding
As a leader of an organization, I’m responsible for hiring well. One of the best shortcuts for hiring is for candidates to know how your organization functions. That helps to select candidates who are interested in your way of working and select out those who would be happier elsewhere. The Netflix Culture Deck is a famous version of this. Informing candidates about your company is employer branding. How do you tell them? Blog posts and talks are great ways to do this.
To Meet People
I’m an introvert, and meeting new people is something I need to force myself to do. When I attended conferences, I would hang out with people I already knew or sit by myself. Being a speaker makes things much easier for someone like me. People will approach me because they’ve seen my talk and have questions or comments. Now that I’ve been speaking for years, people approach me before I talk because they saw me speak at a prior conference. It makes things much less awkward for a person like me.
To Find Customers and Learn from Them
We build software for people. Speaking about our product or product development can be helpful information for potential customers. When researching a software product for my company, I often look at the tech talks or technical blog posts from the company’s technology team. I want to know how open they are about their issues, the kind of stack they use, and whom in the company I may want to reach out to if we have questions or a problem (and not have to go through the sales team).
Personal Branding
While many people think this is why most people blog or speak to promote themselves (carrying with it a sense of icky egomania), for most of my friends who are frequent writers or speakers, this is usually the least important reason or not a reason at all. There certainly is a benefit to having your name attached to a well-known talk or often-shared blog post. I’ve been approached for new jobs because people have read something I wrote or seen a presentation that I gave, but this happens far less often than you might think. If your primary reason for writing or speaking is to get “famous,” there are better ways to do that.
How you can get started
Just do it
“All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer.” ? Ira Glass
The best way to do it is to do it. Create a blog. Give a talk to your team. It probably won’t be very good. When you are getting started, you aren’t perfect. It’s a skill like any other. You must develop it; the only way is to do the work. I’m an ok writer. My taste still exceeds my ability, but I write much better today than when I started blogging. My early posts are embarrassing to me now, but I’m glad I wrote them. Otherwise, I wouldn’t have improved at all. I’m thrilled that my earliest talks aren’t on YouTube. They were cringy. Through practice and repetition, I’m a much better speaker now and can give an opening keynote to 5000 people without having a panic attack.
Pedestrian: “How do I get to Carnegie Hall?” Street Musician: “Practice, Practice, Practice”
Start Small
It’s easy to create a blog. Plenty of free platforms exist to do just that. Create an account and go! Give yourself a goal, such as one blog post monthly if you don’t enjoy writing. One blog post per week if you are ambitious. The trick is to make it a habit. Writing isn’t something I do naturally; I must make myself do it. My posting is extremely infrequent when I don’t have a blogging goal.
You can propose talks to every conference in the world from the day you decide that you’d like to become a speaker. Still, getting started with presentations in your own company or at a local meetup is probably better to build your skills and confidence. They are much easier to get into and more forgiving of inexperienced speakers. Some conferences pride themselves on giving first-time speakers opportunities and coaching. However, I would still look for any opportunities you can to practice giving talks and not count on those. While I haven’t tried it, many people have raved to me about their experiences with Toastmasters International.
Read/Watch
To be a writer, you must be a reader. Find blogs that you like and follow them. They don’t have to be about technology. Read not just for content but for style. You are trying to understand blogging, not just the subject. How do writers you like address their audience? Are they formal or personable? Do they use complicated jargon, or do they try to address wider audiences? Understanding what resonates with you in the writing of others will help you inform your style. It also helps you to understand the conventions of the medium so that you can embrace or ignore them (as you wish). Every YouTube video says some version of “hit the subscribe and like buttons,” for example.
Watch recorded talks from conferences, and find the presenters you like. How do they structure their talks? How do they organize their slides? How do they involve the audience? Similarly, what are the conventions? What things do you want to adopt or ignore? I can say that when I was trying to improve as a speaker, I would try to adapt cool things I saw other speakers do. I still do some of those things, but have found my version. Great artists steal, but eventually, you should find your version of an approach.
Build Up
As I said above, improving writing involves writing as often as possible and reading as much as possible. Improving speaking also requires repetition, but it is harder to find public speaking opportunities.
Giving talks within your company or local meetups will be easier than at national or international conferences. If you feel comfortable and want to grow your experience, expand your subject beyond technology. Find opportunities to give talks about your favorite hobbies. Try different structures, like Pecha Kucha or PowerPoint Karaoke.
You could also write talks and record them, then post them to YouTube.
Once you have some experience and gained some confidence, you can start applying to speak at conferences. Some excellent resources for CFPs are linked below (Call for Proposal/Participation/Papers). Writing talk proposals is a skill in itself, but it will also benefit from practice. If you feel strongly about a talk idea, try writing the proposal for it in different ways. Do your best to tailor your proposal to the conference. Reference the prior year’s schedules to know the kinds of talks the organizers prefer and what successful proposals look like.
Be patient and persistent. It may take many submissions before your first conference talk is accepted.
Your talk was accepted!
Congratulations! It’s exciting and a bit scary. If the conference offers coaching or speaker preparation meetings in advance, take advantage of them! It’s an excellent resource for an inexperienced speaker.
Different people have different processes for preparing for a conference talk. What works for one person may not work for you. I will describe how I prepare; you can try my method. Feel free to adapt it and make it your own.
I often write my proposals based on ideas I have. Once one of them is accepted, I will sit down to write the actual talk. I usually start with an outline. It is usually far too long for the time I have to give the talk, but it is easier for me to remove content than to add it. I typically budget for one slide per minute. For a thirty-minute talk, I will expect to need thirty slides. I don’t necessarily spend the same amount of time on each slide; it just helps me set my expectations.
I don’t focus on making the deck too pretty at first. I want to get the content and some initial timing correct. Once I complete the first draft, I will try giving the talk to see how it flows. Often, that will help me identify extraneous or missing elements. I then refine the deck, try giving the talk again, and further refine it. I may go through many passes of practicing and refinement before I feel comfortable with the flow and content. As the talk feels more “solid,” I will pay more attention to the timing. Am I close to the desired length? A bit over or under is easy to fix, but if the talk is far too long or short, I will need to make some more radical changes.
Once the content and length are close to where they need to be, I will focus more on the structure of the slides. I will break up slides so as not to have “walls of text,” or I may move the text off of the slide entirely and move it to the speaker notes.
Once the design and structure of the slides feel right, I will continue to practice to get a sense of the timing for each slide. I want to have a rough timing in the speaker’s notes to know if I’m getting behind or ahead of where I expect to be when presenting.
Finally, as the day of the conference approaches, I will continue to practice the talk. I don’t want to memorize; I may want to remember some key phrases, but I want to have the structure of the talk memorized. On multiple occasions, the projector or presentation computer has failed, and I’ve given my talk without slides, adapting the message and content to the lack of visuals. It gives me confidence that, as a speaker, I know my presentation. Because I don’t memorize it, I can adapt my words to address members of the audience or refer to earlier talks without worrying about losing my place.
A Secret about Speaking and Giving Talks
The more you do it, the more you’ll be invited to. I still submit CFPs for conferences I am anxious to speak at or haven’t spoken at before, but about half or more of the talks I give are now at the organizers’ invitation because they have seen me speak before.
Similarly, while I continue to publish on sites I control, I get many more invitations to contribute to larger sites because the editors have read something I have published elsewhere.
I wish you the best of luck on your writing or speaking journey!
Slideology by Nancy Duarte If, like me, you are not a graphic designer, this book will help improve the design of your slides.
Scott McCloud: Understanding Comics Ted Talk One of my favorite speakers. Watching this talk inspired me to move to a much more visual slide style (with less text) and to vary the cadence of my slides.
“Thought Leader” TED talk Parody from CBC Radio, “How to sound smart in your TEDx Talk” by Will Stephen These are parodies, but they do an excellent job of exposing many of the tropes of popular public speakers, specifically the TED talk style. When I started speaking in public, I consciously adopted many of these tropes to help me be more confident. While I’ve shed many of them over the years, I haven’t shed them all.
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.
Your resume is a simple enumeration of your experience and the first sample of work you are presenting to a potential employer. Many developers neglect the quality of their resume because they aren’t comfortable with writing, not comfortable talking about themselves, or simply because they don’t think it is important.
Photo by Vanessa Garcia
Every hiring manager has things that will influence them positively or negatively about a person when reading their resume or CV. Given how critical attention to detail is for developers and technical leaders, lacking attention to detail is a warning flag for me and many other leaders I speak to.
Your resume is a simple enumeration of your experience and the first sample of work you present to a potential employer. Many developers neglect the quality of their resume because they aren’t comfortable with writing, not comfortable talking about themselves, or simply because they don’t think it is important. When there are shortages of skilled developers, hiring managers will often overlook formatting, spelling, or grammar mistakes in a resume. When the hiring manager has multiple good choices for a role, seemingly small things can make a big difference in the perception of you as a candidate.
Weaving in the Details
Remember that your resume is more than a list; it’s a story of your professional journey, skills, and aptitudes. The quality of this narrative directly impacts a hiring manager’s perception of you. So, while it’s crucial to include your significant accomplishments and skills, attention to detail helps to fill in the gaps and provide a comprehensive picture.
For example, including specific project details, like what technologies you used, your role in the project, and the quantifiable results, can set you apart from the competition. These details reveal the true extent of your abilities and demonstrate your authentic experience as a technologist and your focus on the outcome, not just the output of your work.
Evidence of Care and Dedication
Meticulous attention to detail on a resume is a positive signal to employers. It’s a testament to your dedication and commitment to excellence. On the other hand, errors, inconsistencies, or vague descriptions can give the impression of carelessness or lack of effort. Spelling and grammar mistakes, easily caught by a spelling or grammar checker in a document editor, are red flags. If you have front-end or user-facing application development experience, inconsistent or poor formatting questions your skills.
Detailing Technical Proficiencies
Specificity in listing your technical skills is another area where detail matters immensely. A generic mention of “programming languages” won’t do the job. Instead, list each language and technology you are proficient in, ideally linking them to your professional experience or projects.
Compatibility with Job Descriptions
Lastly, close attention to the job description can make all the difference. Customizing your resume to fit the specifics of the role shows a proactive and thorough approach.
How to debug your resume
Use a spelling and grammar checker.
Have a friend (preferably someone experienced in reviewing resumes) proofread it.
If you are putting your resume into a language where you are not a native speaker, have a couple of people who are native speakers read it over for tone and phrasing.
If you are unsure how to phrase something, find other resumes (or LinkedIn profiles) from folks with similar experiences to see how they express it.
If you are updating your resume with new experience, read it thoroughly to ensure that the new and old sections have the same tone of voice and style.
Once you have made your changes, put your resume aside for a day or two and then reread it with fresh eyes to catch anything you may have missed.
These things seem obvious, but I can’t count the times I’ve found glaring errors in resumes where the candidate did not follow those steps.
Don’t disqualify yourself for silly reasons!
Attention to detail in a resume could be the difference between getting your foot in the door or having it firmly shut. As a technical professional, your attention to detail should reflect in your work, and there’s no better place to start demonstrating it than your resume.
A well-crafted, detailed resume is your representative in your absence, showcasing your abilities and a testament to your commitment to precision. So, the next time you revise your resume, remember to keep the details in focus. It might just be your key to the next big opportunity.
Your resume is an opportunity to illustrate who you are as a professional and how you approach your work. Attention to detail not only elevates your resume above the rest but also demonstrates the values essential to success in technology: meticulousness, precision, and a deep understanding of your craft. The details aren’t just details; they’re differentiators.
Not long ago, I was mentoring someone starting a search for a new role. The person was curious about how to interview a prospective employer.
Not long ago, I was mentoring someone starting a search for a new role. The person was curious about how to interview a prospective employer. I wrote explicitly about this in a blog post a few years ago (https://leaddev.com/professional-development/taking-thoughtful-approach-job-search-process), but I think I was able to further distill some of the ideas in our conversation.
There are three things when considering a new role assuming the basics (i.e., pay, benefits, location) make sense.
Can you be successful at the company?
Does the role move you toward your career objectives?
Are you excited about what you will work on?
Suppose you can get all three. Wow! Take that job! Two of the three is pretty good, but it likely means that you should not expect the role to be long-term unless you misjudge the situation or something changes. One of three? Take it if you must but have an exit plan.
If you are in a decent role today, you can always choose to keep looking rather than take something that doesn’t meet enough of your criteria. While the lure of something new might be tempting, it can be hard to understand a role before you are established in it. If your initial investigation raises questions, it may be better to keep your search going.
The critical element is knowing yourself and the perspective role well enough to make the determination (the technique I describe in the blog post referenced above is helpful for this). If you don’t know what you want, keep exploring. Look to new roles to increase your skills or experience with industries, company size, or company culture.
Once you know the conditions where you do your best work, where you want to go with your career, and what excites you to work every day, you can put together questions to ask when talking to the recruiter or as part of the interview process.
Try to avoid asking direct, obvious questions. If the interviews are going well, people may tell you what you want to hear. For example, asking, “How is the work/life balance at your company?” is less likely to be helpful than asking, “What times do meetings usually start or end during your day?” If several employees tell you that their day starts early or ends late, you will see some work/life balance patterns.
Another problem with direct questions is that they reveal more about you than you might want in an interview. For example, when a candidate asks me a direct question about something specific, such as raises, review processes, or work/life balance, it tells me not just that they are interested but that they may have had bad experiences with this in the past. If I get a sense of a bad experience, it will usually prompt me to better understand the nature of their concerns. If you are concerned about review processes, for example, I wonder if you have received negative reviews in the past and what was the story behind them. So, asking more generally about how often the company performs appraisals and the process will elicit less concern than asking how employees can appeal negative reviews.
Ask indirect questions about how the work is done, the day-to-day responsibilities of the role, and what conflicts arise. Look for clues in the answers that speak to reality. You may find some of your interviewers are more forthcoming and open. Leverage that transparency. Find friends or friends-of-friends that know people who work there to get the unvarnished truth.
But also realize that companies evolve just as people do, just as you will. So even if things are good for you initially, they may not stay that way.
So, when your three-of-three company becomes your two-of-three company, you may wait things out to see if things will change, but you also might want to start looking for your next three-of-three company. Although every company will have good/bad periods, once you have been at a company for a while, you’ll understand if the current situation is temporary or part of a more permanent shift.
Of course, in today’s job climate, you might need to take that one-of-three job or even zero-of-three position. If that is the case, don’t despair. Instead, focus on taking care of things until you can find a role that fits you better. Tech is cyclical, just like the broader economy. If you can wait it out, things will get better.
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.
