This is a submission for the 2025 New Year Writing challenge: Retro’ing and Debugging 2024.
2024 was a wild ride for me! It was a year of learning to accept things as they are and go with the flow. It was also a year where I saw the darker side of being an engineering manager in a startup. I was proud of being an engineering manager because I could make a real difference in people’s lives, boost team morale, and create a collaborative environment between teams. But during my second year of being an engineering manager in a startup, everything went completely upside down. Here are the challenges, lessons, and lessons I learned during the toughest year of my career.
đź’Ą Challenges:
- Balancing performance appraisals with financial constraints and no bonuses.
- Keeping team spirits high during tough times and uncertainty.
- Making the tough decision to lay off employees when things got even worse financially.
- Leading the team through emotional ups and downs while meeting expectations.
đź“š Lessons:
- Being honest and open, even when delivering bad news, is super important.
- Rebuilding morale means showing empathy, getting to know your team, and celebrating small successes.
- As a leader, you have to make tough choices, but you can still support your team by being there for them.
- Sometimes, the best way to grow is to face challenges and learn from them.
🎉 Achievements:
- I helped the team get back on track by having one-on-one meetings and focusing on the little things that really matter.
- I successfully led a restructured team as a proxy tech lead, and we had some amazing sprint performances! I played a key role in completing some important features that improved the company’s finances.
- I came out of this experience stronger, more focused, and with a deeper understanding of what it means to be a leader.
Chapter 1: The Winds of January
The year 2024 began under a heavy cloud. January, the month of reflection and appraisal, felt unusually tense. It was the season for performance reviews—a time that typically brought a mix of anticipation and excitement. But this year, things were different. The company’s cash reserves had been significantly depleted, a harsh consequence of decisions made in 2023 that had not borne the fruits we had hoped for. Adding to this, global economic uncertainties and geopolitical conflicts had cast a long shadow over the leadership’s outlook, forcing them to take a more conservative stance.
One cold morning, my VP of Engineering approached me, his expression serious. He outlined the company’s risky financial position and explained the implications for the upcoming appraisal season: there would be no bonuses. Salary increments? Reserved only for those who had truly delivered exceptional results in 2023.
This was my second time leading performance appraisals as a manager. I knew it would be tough, but nothing could have prepared me for the weight of what lay ahead. My team had worked tirelessly—long nights, countless weekends—to ensure that the features we believed in were delivered on time. Despite our efforts, we had not achieved the outcomes we had hoped for. I braced myself for the conversations that awaited, fully aware of the disappointment that would follow.
Chapter 2: Facing the Team
I have always believed in honesty, even when the truth is hard to hear. As a manager, I refuse to make false promises, no matter how tempting it might be to cushion the blow. I gathered my team for a candid discussion, explaining the company’s situation and the reasons behind the tough decisions. Then, one by one, I conducted the individual performance reviews.
It was a delicate balance. I wanted to acknowledge their hard work and dedication while also providing fair and constructive feedback. Most of my team appreciated the transparency, even if the outcome left them disappointed. Some were disappointed, others visibly upset. A few expressed their frustration openly, their words held with resentment and sadness. I listened patiently, remaining calm and composed, even as the emotions in the room threatened to overwhelm me.
As expected, morale took a hit. The energy that once fueled our team’s collaboration and creativity seemed to dim. Some team members became quieter and less enthusiastic about their tasks. Others, to my surprise, remained optimistic, choosing to see the challenges as opportunities for growth.
Chapter 3: A New Perspective
Recognizing the drop in motivation, I decided to take action. I scheduled one-on-one sessions with each team member, not just to talk about work but to reconnect on a personal level. These conversations were crucial. They allowed me to understand their concerns, aspirations, and frustrations.
During these sessions, I tried to shift the narrative.
“Success isn’t just about titles or monetary rewards,” I told them. “It’s about growth, learning, and the impact we create. Every challenge we overcome makes us stronger.”
Some nodded in agreement; others needed more time to process. Slowly, I noticed a shift. While the sting of disappointment lingered, there was a renewed sense of purpose. We started focusing on smaller wins, celebrating progress.
Chapter 4: The Hardest Goodbye
By May, the company's financial situation had worsened. My VP of Engineering approached me again, his tone heavier than before. This time, the conversation was about reducing the size of the team. We discussed the company's state and the difficult decisions that lay ahead. By the end of the discussion, he delivered the crushing news: we had to let people go.
At first, I was in denial. This team has been with me through countless challenges. Each member brought unique strengths that contributed to our success. I pushed back, arguing passionately to protect them. But after several rounds of discussion, I came to understand the harsh reality—to keep the company afloat, sacrifices had to be made.
For the first time in my career, I faced the unbearable task of deciding who would stay and who would go. It was the hardest and most emotional decision I had ever made as a manager. Over three grueling rounds of SWOT analyses, I evaluated each team member’s capabilities, behaviors, and performance over the past two years. Eventually, I arrived at a list of names—a list I had hoped never to create.
After finalizing the list with my VP, I moved forward with the layoff conversations. These were some of the most challenging moments of my career. Letting someone go is never easy, especially when they have placed their trust in you as a leader. My team saw me as their protector, someone who shielded them from external challenges so they could focus on achieving our goals together. The weight of that expectation made the task even more heartbreaking.
Some of those I let go had families to support, and given the difficult job market, the impact was devastating. I prepared myself as best as I could, maintaining calm and composure during the conversations. Still, the immediate reactions—shock, sadness, and sometimes anger—were brutal. Even though most understood the rationale, I could not shake the feeling that I had betrayed them. It felt like I had robbed them of their drive and stolen their motivation.
Afterward, I became quiet and withdrawn in the office. The emotional toll was overwhelming, and I requested to work from home for a time. For two weeks, I wrestled with my decisions, replaying every conversation and second-guessing every choice. Sleepless nights became routine. I often found myself on my balcony, gazing at the stars, questioning the kind of person I was and whether I wanted to continue on the path of engineering management. The experience left me deeply reflective, forcing me to confront the complexities of leadership and the heavy responsibilities it entails.
Chapter 5: Stepping Into a New Role
The months of August to December 2024 marked another turning point. Following the recent layoffs, the team was undergoing a restructuring, and I was appointed as a proxy tech lead for one of the restructured teams. This role came naturally to me. Even as an Engineering Manager, I remained involved in sprints, regularly contributing as an engineer. Stepping into the tech lead position wasn’t a challenge but rather an opportunity to focus on something new while recovering emotionally from the earlier turmoil.
As a tech lead, I found the role both refreshing and rewarding. My responsibilities centered on delivery, and I quickly set about molding the team—a senior engineer and two interns or juniors—into a cohesive unit. Together, we tackled crucial features that played a significant role in helping the company secure deals and regain its financial footing. The pressure was intense, but it was also gratifying. The synergy within the team was remarkable, and for the first time in months, there was a sense of momentum. We consistently met our goals, breaking records since the company adopted Scrum.
The experience of leading this team reaffirmed my love for building and delivering impactful solutions. It also reminded me of the power of teamwork and resilience, even in the face of adversity.
Chapter 6: A Bittersweet Farewell
As the year drew to a close and management began planning for 2025, I reflected my journey. The challenges, growth, and victories all painted a vivid picture of an insightful year. But as I reflected, I realized it was time for a new chapter. This chapter doesn't involve my current company in the picture—the company that I had been with for seven years, from an intern to becoming an engineering manager.
In December, I approached my VP of Engineering and submitted my resignation letter. It was a decision made with a heavy heart and a sense of clarity. My journey with the company has been transformative. I had grown immensely, both professionally and personally. The relationships I built, the challenges we overcame, and the milestones we achieved were unforgettable. Yet, I knew it was time to explore new horizons.
Final words
Thank you very much for taking the time to read this short novel-like article. If you dream of becoming an engineering manager, don’t let this discourage you. I hope I can give you a realistic glimpse into what it is like to lead a team. Right now, I am taking a little break from my leadership role to recharge and focus on the things I love doing technically. I enjoy solving meaningful problems using technology while I recover from my energy. Does this mean I will never take up the engineering manager position again? Haha, no way! I will always be up for the challenge of improving people’s lives, but I think it is important to take some time out to reflect and improve my skills in other areas. The goal is always to become a great problem solver.
Top comments (7)
Thanks for sharing that story. Last year, I also went thru the infamous layoff season but from the leaving side. I can't imagine how hard it should have been for the staying side too: The uncertainty of a sinking boat without fate any time.
I wish I had told my younger self: Always have an emergency fund, grow your network, have a side business... Winter is always coming!
Thank you @canro91 for reading. I am so sorry to hear about your layoff. It must have been tough.
The staying side was tough too, because of the cash flow issue. There were times when the company could not pay our salaries, and some of us had it going for nearly 3 months. Being in that situation and still needing to deliver features was really challenging for everyone. The only thing that kept us going was each other and our mindset. We were determined to stay positive and motivate each other.
For me, I was a bit lucky because I’ve been saving since I started working. Because of the startup culture, I understand that winter is always coming.
Stay strong and I wish you luck in 2025.
Agree! Coworkers and friends make the day to day grind easier.
Happy coding!
Thank you for sharing this heartfelt and inspiring story. It’s a raw and honest glimpse into the challenges and growth that come with leadership, especially in a startup environment. Your resilience and empathy shine through, even in the toughest moments, and it’s clear you have made a lasting impact on your team.
I admire your focus on personal growth and your decision to take a step back to recharge and reflect. It is a powerful reminder that leadership is not just about leading others but also about knowing when to prioritize your well-being.
All the best for 2025 and looking forward for more content from you.
Thank you for reading @tufomu2681. Yup we are not running a race here, life is a marathon. I am amazed with where I am in these 7 years and the last 2 years in leadership have been quite challenging. It is good to take some time off, rest, travel, and learn other new things in tech and who knows maybe after 3 or 5 years later I might step back into the leadership role with better enthusiasm.
Wow just wow. It is quite an eye opening article. I guess those are the perks of being a leader. Thanks for writing this out.
Thank you @kogybo208, yup the perks of being a leader. You will learn a lot when it comes to decision-making.