Lessons Learned in a Year as a COO in Tech

A green apple sitting on top of a stack of books with a blackboard in the background
Sarah Woods

Chief Operations Officer

Sarah Woods

As we near the end of my first full fiscal year as Chief Operating Officer at DockYard, I am taking some time to review what went well, what hasn’t, and the lessons I’ve learned along the way.

Starting as a New COO

I openly admit that when I stepped into this role in June 2022, I was filled with apprehension. However, what happened was quite the opposite. The enthusiasm and acceptance I received in this role were both a surprise and thoroughly welcomed. My path to this position was illuminated by the assurance and trust that others had in my skills and qualifications, even during moments when my self-confidence wavered. As time has progressed, I have felt more and more confident in my role.

With over two decades in HR, I’ve honed my expertise and felt assured in my capabilities. However, stepping into this new position brought a unique set of challenges. In previous senior HR roles, I offered insights into major strategic decisions, but the final call wasn’t solely mine, which provided a sense of security. Now, I have the responsibility of synthesizing my colleagues’ input and determining the best course for DockYard and its employees.

While I haven’t always gotten it right, I try to be transparent by owning up to my mistakes, gleaning whatever insights I can from them, and pressing forward. What I’ve learned, however, is that trust in yourself and that of your team is crucial in decision-making. For me, this trust is built on a foundation of transparency, vulnerability, and a steadfast commitment to integrity.

Lessons I’ve Learned as a COO in Tech

You Can’t Do it All…

I became COO at a time when DockYard was undergoing a transformative phase, shifting its focus and investing further into the Elixir ecosystem.

In addition to getting settled into a role that was outside the comfort of my prior HR career, I was part of an organization engaged in something entirely different than what we had done previously. All to say, it was a lot to adapt to.

So, I began learning as much as I could (more on that later). This self-education occurred at the same time I was leveling up members of my support team and onboarding a new Controller. This all meant I was still performing many of my same duties while taking on more responsibilities.

Eventually, I spent nearly every waking moment on preparation and work which, anyone will tell you, is a recipe for disaster. I was burning out and neglecting things that made me healthy and happy. I hadn’t seen friends in months, I reduced the time I went to the gym, I rarely ate actual meals, preferring to snack at my desk or mindlessly eat takeout on the couch. I was also waking up earlier and earlier, getting maybe four to five hours of sleep a night.

As much as I touted “work/life balance” for my team, I wasn’t walking the walk. And others noticed when I’d forget to schedule an email or Slack message and they could see what time things were being sent.

…So Delegating is a Must

Moving into this role has forced me to delegate, which has never been a strong suit of mine. Having been a “department of one” for much of my career, coupled with the concern of burdening others with something I could do, I tended to “just do it myself” rather than hand things off to others.

This wasn’t because I necessarily thought I was better at the tasks. Instead, it was that I worried I was overburdening my team or, if it was something small and tactical, I thought it wasn’t important enough to give to someone else to handle.

It took my Director of Employee Experience asking for more work to do and asking how she could make my life easier (a common question I ask my team in our one-on-ones). I had to learn to oversee and not control. In doing so I was able to free up my time and we had so many new programs and improvements as a result!

I often coached hiring managers to “hire your weakness,” which meant looking for people who supplement your skills. Our employees excel in their respective crafts, and their diverse talents complement any areas that may require additional expertise. I had to take a step back and remember the coaching I gave others, and live by it.

There was no way I could manage all of the things I was once responsible for before while also taking on new responsibilities and partnering with others to pivot the company to align with the new vision established by the CEO in December 2022 (although I certainly tried).

I started handing things off to others and giving myself permission to leave them to it. I didn’t pester them for updates or offer my opinion (unless asked). It was freeing and I loved seeing my team step up to the challenge, advance their own skills and knowledge, and become more confident in their abilities.

Your Opinion Carries Weight—Use it Wisely

I was accustomed to people seeking out my opinion in HR matters after over 20 years of experience in the field. However, stepping into this new role brought about a different experience, one I was not initially confident in. Suddenly, I found myself among the most senior individuals in the company, and all eyes were on me.

It became evident that when I spoke, people paid attention. Over the course of my career, I’ve learned some valuable lessons encapsulated in the axiom “Act in haste, repent at leisure.” I was generally mindful of my words and aware of my audience. But in this new position it felt different; it felt like there was more at stake.

Previously, being a source of information without being the ultimate decision-maker provided me with a level of anonymity and immunity. However, that was no longer the case. The decisions I made directly impacted the company’s financials, which in turn affected the livelihoods of our team members.

The weight of my choices extended beyond the workplace: They could determine whether someone could make their mortgage payment or continue to provide health insurance for their family. It was a profound shift, and I found myself taking on a role almost opposite to my “in real life” self (which tends to be far more relaxed) and gaining a newfound appreciation for the challenges faced by leaders from my past.

This experience taught me a valuable lesson—my opinion carries significant weight, and I need to exercise it judiciously. The decisions I make have the potential to shape not only conversations within the company but also broader outcomes that could profoundly impact individuals and their lives.

People Will Believe What You Do More Than What You Say

If you want your team to trust you, you need to be trustworthy. True impact comes from consistent visibility, especially during crucial decision-making moments. This year businesses around the world felt the challenges of the lingering effects of a global pandemic, dramatic inflation, and a surge in layoffs and unemployment. As a B2B consultancy, DockYard felt the repercussions of these events, which prompted us to navigate a more conservative spending landscape.

In response, we’ve had to make difficult decisions around spending and headcount. Every non-essential expenditure was scrutinized and, unfortunately, we had to make the tough choice of laying off some of our team members.

Having been the one being laid off in the past, I have always believed that it’s paramount to approach these decisions authentically and truthfully with kindness and compassion. I tried to embody these traits as I’ve become the decision-maker.

Many of the leadership lessons I’ve learned come from seeing those concepts in action. I’ve learned as much about good leadership by witnessing bad leadership and what I don’t want to be than I have in seeing good leadership to aspire to.

For example, I have seen leaders make excuses and spread blame rather than accepting it. So I make the adage “the buck stops here” a guiding principle I try to live by. Whether factors leading to decisions to cut spending or headcount are internal or external are immaterial to the people impacted by these decisions. In those discussions, the team member deserves to hear from those responsible for the decision, acknowledge the team member’s feelings and fears, and do everything in their power to help the team member navigate the situation with as much ease as possible.

Along with my other C-suite colleagues, one of the ways we’ve embodied that is by making ourselves available to address the company. We’ve answered questions that came up through an anonymous suggestion box as well as real-time questions posed by employees during company meetings. My hope is that the employees trust what I’m telling them and know that I care deeply about each and every one of them.

Never Stop Learning

As I mentioned, I was daunted by the challenges of being COO when I first moved into the role. So, I reverted to my normal modus operandi when faced with the “unknown”—learn as much as you can about the role and what this evolution should look like by people who know more than I do about these subjects.

I read business books, subscribed to industry publications, and attended webinars for tax, operations, and governance in addition to my HR, leadership, and ethics courses.

I also became an active member of diverse online communities to broaden my perspectives and share ideas. Whenever I could, I contributed my own knowledge to those communities as a way to express my gratitude for the generosity of those willing to share their experiences.

I joined a senior-level HR group that provides advice to more junior-level HR practitioners, I spoke at local MBA programs and my alma mater, contributed to a number of crowdsourced articles on LinkedIn, and have been as candid as possible in my official and unofficial mentorship of other professionals.

In my role, I have always viewed it as crucial to fully own my decisions and take responsibility for any resulting backlash, regardless of the underlying reasons. This commitment to transparency and accountability is not only a professional responsibility but also a way to foster trust and understanding during difficult times.


The dynamic nature of the tech industry demands constant evolution, and I’ve gained a deeper appreciation for the blend of innovation, resilience, and adaptability required to steer our organization toward continued success. As I look ahead, I am committed to applying these lessons, collaborating closely with our talented team, and navigating future challenges with confidence and determination.


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