jessingrassellino

Category: education

  • From Coding to Coaching: The Shift that Powers Engineering Growth

    The Untaught Transition

    When I became an engineering manager, I expected the hardest part would be learning to coach adults who were experienced engineers. I was wrong. The hardest part was realizing that most of my peers had not been taught how to do this. Many didn’t think of coaching as part of their job.

    The Common Path: Promotion Without Preparation

    In tech, I’ve observed a common path to leadership: a senior engineer performs well and becomes a tech lead, taking on technical and soft-leadership responsibilities. If there’s no principal engineer or architect track, the next step in career development is typically engineering management.

    But people management isn’t just a continuation of engineering skills. That would be like expecting a brilliant violinist to conduct an orchestra without ever learning about how different instruments work together, or how to guide musicians through complex emotional and technical passages. We would never, so why do it to engineers?

    “In many cases, organizations lack clear training or support for new managers, which results in technical leaders who default to the skills that earned them promotion—usually not people management.”

    Will Larsen, The Engineering Executive’s Primer

    Coding and Coaching: Two Distinct Skillsets

    Software engineering work can be solitary, logic-driven, and quantifiable. Code runs on a developer’s machine, the pull request passes or fails the tests in the pipeline, and is either rejected or deployed. Then, the next development task can start. In contrast, coaching work is relational, emotionally attuned, and often ambiguous, based on the ever-changing nature of the human experience. It is work that’s never “done”. This makes coaching one of the more difficult leadership skills to pick up without preparation.

    Teaching taught me that coaching is an intentional practice, not (fully) an instinctual one. At minimum, coaching requires listening with curiosity, giving specific feedback focused on somebody’s behavior (not their character), and knowing when to push someone, and when to step back to let someone learn on their own.

    “Effective coaching must be intentional, structured, and rooted in curiosity—not command. It’s not a personality trait; it’s a practice that leaders can and must develop.”

    Jean Dahl, Leading Lean

    What Happens When Coaching Is Missing

    Maybe engineering organizations don’t see the need to teach coaching skills to managers. After all, these skills don’t always map directly to solving business problems. But ignoring them has real costs—costs that do impact the business:

    • Micromanagement masked as mentorship
      When managers micromanage, it creates a sense of distrust. I once worked with another engineering manager who reviewed every pull request from their team of (mostly) senior engineers. They believed this was mentorship—sharing their expertise. Instead, it created a bottleneck where those engineers stopped taking technical risks and began second-guessing their decisions.
    • Team members staying stuck because no one’s helping them grow
      Engineers can experience stagnation when they don’t receive meaningful growth opportunities tailored to both their goals and the business’s. Without performance feedback, they can’t see how their decisions impact business outcomes, and they can’t make positive, incremental changes to improve.
    • Glue work going unseen and unrewarded
      Especially for women, neurodivergent folks, and underrepresented engineers, glue work (code-adjacent tasks like documentation, mentoring, or cross-team coordination) often goes unrecognized. Managers can use coaching strategies to ensure that glue work is shared, visible, and valued.
    • Burnout in high-potential engineers who don’t feel supported
      Strong, motivated engineers want to know how they can improve their performance, and are typically very committed to business success. Without coaching and growth opportunities, they may burn out or leave for companies that promise more support.

    I’ve seen all of the above management-related problems at companies where I’ve worked—large SaaS orgs and lean startups alike. I made some of these mistakes myself when I first became a manager, and that was with preparation and experience in people growth. No company of any size is immune to the productivity and morale issues caused by ineffective management.

    “When engineering managers neglect coaching and career development, teams experience disengagement and talent attrition—even among top performers.”

    Robert Santer, Navigating the Engineering Organization

    How I Practice Coaching In Engineering Management

    As a teacher, I was trained to evaluate performance holistically and adapt strategies based on how each individual learned best. As a self-taught software test engineer, I learned to anticipate risk, observe behavior, and communicate clearly. Both skill sets translated directly into the coaching I’ve done over the past eight years as an engineering leader. I have refined many of these skills and learned some valuable lessons over time. Here’s how I’ve translated my teaching background into practical engineering leadership:

    • Using 1:1s to focus on performance and professional goals
      Face-to-face time is precious. I typically use group chat (slack, etc) to give group updates and retrieve work status information, while using 1:1s to discuss personal goals, performance concerns, and give tailored feedback. 1:1s are a lot like music lessons in this way.
    • Adapting feedback models from education, like SBI (Situation–Behavior–Impact)
      SBI is my go-to model for actionable, respectful feedback. I use it for coaching both team members and leadership (managing up), and it’s been consistently effective because it removes the guesswork and defensiveness that often derail feedback conversations. Instead of saying “you’re not communicating well,” I might say: “In yesterday’s standup (situation), when you said the feature was ‘almost done’ (behavior), the product manager scheduled the demo assuming we’d ship tomorrow, creating last-minute pressure for the whole team (impact). Can you tell me more about what happened here?” The SBI approach keeps everyone focused on solutions rather than taking things personally.
    • Creating micro-goals and reflection practices
      Small, meaningful goals keep people motivated. It’s a bit like practicing scales. They seem kind of meaningless in the day-to-day, but achieving wins there magnifies what I’m able to do in the future. I pair micro-goals with short (verbal or written) opportunities for reflection so individuals can track their own growth and see the connection between their daily work and larger achievements. The key to making this work is that I am not giving a grade or a rating. My team member measures their progress against the rubric, and gives their own assessment, which drives discussion and growth.
    • Coaching high-performers to become multipliers
      One of the most important questions I get from senior engineers is: “How can I grow when I’m already at the top of the ladder?” My answer: learn to multiply. High-performers can drive impact by coaching others and raising the overall skill level of the team. This is a lot like the job of the concertmaster or first chair in my orchestras – she assists the entire section with how to play better, lifting up the sound of the entire section and orchestra.

    Coaching Is Core

    Coaching isn’t a soft skill—it’s a core leadership capability that transforms not just individual performance, but entire team dynamics. When engineering leaders learn to coach with the same intentionality they bring to designing systems, they create multiplier effects that ripple throughout the organization.

    And just like writing great code or designing scalable systems, coaching can be learned and practiced. The question isn’t whether you have time to develop these skills—it’s whether you can afford not to.

  • Great Engineers Aren’t Always Great Managers – Here’s How We Can Change That

    Most engineering managers were never trained to lead people, only to ship code. And often, it shows.

    In tech, management roles are frequently given to high-performing engineers who receive little to no leadership training. Sometimes, this happens because an engineer actively wants to move into management. This post isn’t about those engineers — they’re doing great! More often, however, senior engineers are pushed into management because it’s the next (or sometimes the only) step available for career advancement.

    Unfortunately, this sets these senior engineers—and their teams—up for frustration, burnout, and underperformance. I first noticed this gap between engineering skill and people-management skill when I transitioned from leading quality teams to leading engineering teams. I reached the final interview rounds with several companies, only to be passed over for more technical candidates who performed better on code reviews. At one company, the senior engineer who interviewed me for the coding round even reached out to say I was her preferred candidate — but the hiring manager wanted someone more technically advanced.

    Myth: Great Engineers Make Great Managers

    Over the past fifteen years, I’ve worked with many engineering managers—from first-line managers to VPs of Engineering to CTOs. The least effective of them were often exceptional engineers who prioritized technical expertise over communication, business acumen, and building high-trust environments.

    In those environments, engineering teams were poorly represented in cross-functional spaces. I saw former engineers micromanage their reports, insisting they use the exact technical solutions they would have chosen. Eventually, many of those direct reports left in search of greater autonomy and opportunities for growth.

    Why is it that organizations assume a great engineer will automatically make a great manager? There seems to be a persistent belief in tech that technical excellence translates into leadership excellence—as if an engineer’s brilliance will magically “rub off” on their team. Perhaps it’s because management is sometimes seen as less valuable or less skill-intensive than engineering.

    But those of us who have worked under ineffective managers know how harmful these environments can be. MIT knows it too. Their Engineering Leadership Program for Emerging Engineering Leaders emphasizes that engineering management is a fundamentally different kind of leadership—one that centers on trust, team-building, and aligning smart, capable people toward a shared vision, even when they disagree.

    Getting people to disagree and commit is its own skill. And it’s not easy to learn.

    Fact: Ignoring Management Skills is a Problem for Everyone

    Focusing only on technical skills when promoting into management roles can hurt everyone—especially the new manager. I once worked with a director-level manager who was still deeply involved in coding. While many engineering organizations admire this model, it can be problematic. This manager overlooked and even dismissed team members who used different approaches than their own.

    Worse still, the director failed to build relationships outside of engineering. Collaboration with other departments was contentious, when it existed at all.

    This isn’t surprising. Educational research shows that leaders who lack people-development skills tend to have more disengaged staff and lower-performing teams. In my experience in education and leadership development, I’ve seen how learning different leadership styles can help grow individuals, resolve performance challenges, and align teams around shared goals. Personally, I use a situational leadership style and aspire to a transformational one.

    “At the most basic level, transformational leadership is used to inspire employees to look ahead with a focus on the greater good and to function as a single unit with a common goal in mind. It is not until a leader accomplishes these steps that a successful transformation can begin.”Shayna Joubert, 2024

    What Great Engineering Managers Do

    The best engineering managers I’ve worked with came from a variety of backgrounds. One was a top-tier engineer who became a respected industry leader. Another grew a company from two employees to nearly two hundred. The best I ever worked with had previously worked in engineering-adjacent roles and became a highly effective director.

    Despite their different paths, they shared three key capabilities: strong communication, a focus on people development, and a clear sense of purpose. Here’s what they did well:

    1. Build trust through open communication

    Each of these leaders communicated with transparency, telling their teams as much as possible, as early as possible, about business decisions that could affect them. This built trust and made space for meaningful conversations.

    When something wasn’t going well, they addressed it immediately and clearly, then offered guidance and support—without prescribing solutions—so that team members could analyze and solve problems themselves.

    They encouraged opposing views, invited tough questions, and created environments where healthy disagreement improved outcomes. When team members felt heard, they were more committed to solutions.

    2. Let go of your old job and trust others

    These leaders had fully stepped out of their previous engineering roles. They trusted their reports to understand the vision, execute the plan, and learn from both successes and setbacks.

    When someone succeeded, they celebrated the win. When someone struggled, they approached it with curiosity and support, not blame.

    3. Redefine your purpose: grow the people who grow the product

    These leaders understood that their role was no longer to be the best individual contributor. Instead, they were multipliers—amplifying impact by developing others. Each person they mentored became a force for greater outcomes across the organization.

    Management Is a Learnable Skill

    The good news? Just like engineering, management skills can be learned and improved.

    If we want to set senior engineers up for successful leadership, we need to teach and reinforce key management competencies. Even experienced managers benefit from refreshing and expanding their skillsets.

    Here are three areas to focus on:

    Giving and receiving feedback

    Structured mentorship and regular feedback are key to improving performance and retention. Using models like SBI (Situation–Behavior–Impact) can make feedback more actionable and trustworthy.

    Leaders also need to ask for and receive feedback to grow trust, model vulnerability, and stay aware of their blind spots.

    Developing emotional intelligence

    Emotional intelligence is critical to effective leadership—but it’s also one of the hardest skills to build. It requires honest self-reflection, empathy, and a willingness to grow.

    Practices like journaling, daily reflection, and leadership coaching have helped me immensely. Many strong leaders use similar tools.

    Becoming a lifelong learner

    Great leaders are constant learners. Staying curious and informed boosts confidence, cognition, and work-life balance. (And learning doesn’t have to stay in your field—I’m a violinist, and I draw leadership lessons from music all the time.)

    Some companies invest heavily in management training, while others offer little or none. I once worked for a deeply technical company that also provided the best management training I’ve ever attended—it was required annually.

    Even without formal programs, resources are widely available. Many companies offer education stipends. High-quality research and training are available online. And interactive formats—virtual or in person—can offer real-time coaching and feedback.

    The key is recognizing that management is a skillset, as complex and valuable as any technical one.

    A New Definition of Great Engineering Management

    It’s time to broaden our definition of leadership in engineering.

    Great engineering managers don’t just ship code. They lead with emotional intelligence, invest in the growth of others, and build resilient, collaborative, high-performing teams.

    They don’t just grow products—they grow people. And people make all the difference.

  • Ms. Jessica

    jess ingrassellino, October 2020

    I was the headmaster at my school for orphans. “No, no, NO! You have to

    stand right here. Princess wouldn’t go over there,” I’d command my younger sister, who played every supporting actor role with passion and vigor. We played this game where we pretended to be orphans every day after school. I was probably ten or eleven before we fully quit the game because we got too old for imaginary sanctuaries.

    It’s kind of funny to me now, to think back on what I thought teaching and helping were. Mostly, I thought it meant being in-control, and getting to have control. Both equally appealing to my child-mind. It was strange when I realized that teaching, the art, the act, had nothing to do with power or control.

    “Miss Jessica. Miss Jessica, will you help me with my card?” This little boy was a first-grader in the classroom where I volunteered after school a few days a week. In a rare moment of clarity, my mom had recommended that I volunteer in classrooms since I was interested in teaching, so I did. I met with the elementary school principal, and the next week, I was volunteering in a first-grade classroom – actually, my first-grade classroom, with my first-grade teacher, who was now in her forties.

    “Oh, that’s a beautiful card. Your mom will love it.”

    “This card isn’t for my mom,” he replied, “it’s for my Grandma. My mom’s dead.”

    As a sixteen year old, that was pretty much peak awkward. I tried my best to recover: “Well, I know your grandmother is just going to love that card.”  For weeks after,  I felt like a fool for assuming that he had a mother because he was making a card.

    Over and over again, my students have called me out — usually inadvertently — highlighting the gaps in my knowledge and limits in my experience. I’ve started to think that teachers are just people who like learning things the hard way. Within my first four months of teaching high school, I was certain I’d lose my job.

    “You know what lady, I don’t give a shit!” Eddie shouted.  Eddie, the 19-year-old senior. The genuinely nice kid who put on the tough-guy armor to make the world safer for himself.

    “Yeah, well, you know what?”

    I, all twenty-three years of me, yelled, “I don’t give a shit either. Now go to the principal’s office!”

    Yeah. I did it. I lost my entire temper in fifteen seconds. Couldn’t sleep for a week. Kept waiting for my whole career to get upended. You know what they don’t teach you when you study to become a teacher? They don’t teach you that all of the shit you’re struggling to leave behind is the shit that’s going to bite you every day until you deal with it. That illusion of control I had when I was five? It went out the door with Eddie.

  • Beauty in the Process

    This week, I experienced starting a lot of different types of learning. I am working on obtaining my AWS certification, so studying for that; I also started working on a piece of music and that meant needing to learn how to use a new looper pedal! AND I started writing a new poem.

    Toward the end of the week, I also read a tweet from a good friend who felt very frustrated with his inability to focus. This got me thinking about the idea that we have to focus our energy in long, intense sessions in order to achieve something.

    For example, this week (and most weeks), I don’t really have TIME to focus for very long. Maybe I get a free half hour during the work day, and then another hour before bed to do calmer things like reading, writing, or planning for my day.

    One of the things I tried this week was practicing an etude. It turns out that etudes are a great metaphor for many things we want to do in life. Most musicians detest etudes at some early point in their career. Etudes seem a bit pointless; we practice them, but the benefit is unclear in the short term. During my undergrad, those 30 minutes a day I spent on my weekly etude were frustrating at first. After a year, though, I started to love etudes! These short studies forced focus by only being “about” one thing – one bow technique, or one left hand technique, or one musical technique. The structure of the etude allowed me to use a shorter period of time to improve one area over the span of a week.

    In that spirit, I have approached the past few weeks. My learning and products are not done. Is learning ever done? At any rate, I was pretty reluctant to share this week, because it’s hard to share something when it doesn’t feel finished. That said, I think it’s important to share with you the poem I’m halfway through writing.

    handwritten draft of a poem I’m working on, after Lady Lazarus by Sylvia Plath

    The above picture is of my journal from this past week, as I’ve worked on my poem, modeled after Lady Lazarus, by Sylvia Plath. It is one of her later poems, one that I’ve known for more than twenty years now. In all that time, I never read the poem quite as I did during the past week. For the first time, the rich depth of her imagery became apparent to me. It is difficult to craft a poem the way she does, and I found myself stuck. I couldn’t finish the poem in time for this week’s post. Instead, I give you this, an unfinished work.

    A reminder: just because you don’t have all the time, all the energy, all the focus, or all the answers, doesn’t mean to let go of what you want to accomplish. Accept yourself, where you are, and know that you’ll get where you want to be with steady effort, regardless of the bumps. And hopefully, I’ll be able to share a complete poem with you next week. Cheers!