Navigating career transitions in the tech industry: 17 pieces of advice 

Navigating career transitions in tech leadership can be as complex as the technology itself. We’ve gathered insights from CTOs, CEOs, and founders, distilling their experiences into seventeen valuable pieces of advice. From diving in and embracing learning to upskilling and tackling new challenges, these technology leaders share their wisdom on making significant career shifts. Are you navigating career transitions in the tech industry? Here are 17 pieces of advice:

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  • Dive In and Embrace Learning
  • Focus on Adaptability and Mentorship 
  • Craft a Detailed Transition Plan
  • Cultivate Empathy and Curiosity
  • Embrace Humility and Seek Growth
  • Learn and Embrace New Perspectives
  • Set Hard Deadlines for Role Transition
  • Stay Flexible and Pursue Innovation
  • Admit Knowledge Gaps and Delegate
  • Commit to Lifelong Learning
  • View Unknowns as Growth Opportunities
  • Push Through Negative Emotions
  • Leverage Networking Before Transitions
  • Realize Debugging Extends Beyond Code
  • Align Purpose with Career Moves
  • Avoid Imposing Old Systems
  • Upskill and Tackle New Challenges

Dive In and Embrace Learning

I found myself leading in tech when I began my own company. Suddenly, it was more than just tech. I had to find the best ways of doing things and follow rules correctly, and understand that even if a product is good, it might not be usable. 

Sometimes, politics prevent a good system from being used in big companies. I also saw that being a small company means some rules only apply to us, not the big companies. The biggest thing I learned is not to be afraid to dive into anything. Thinking you know less than others is all in your head. When it really matters, your ability to learn is the most important skill.

Sujeet Pillai, CTO, Incentivate, Aurochs and Mailshouts, Incentivate Solutions

Focus on Adaptability and Mentorship 

As a seasoned technology leader, I’ve encountered several pivotal career transitions throughout my journey. Each transition brought its unique challenges and opportunities for growth. 

One piece of advice I’d like to share with others navigating similar transitions is to embrace adaptability. Transitioning roles or levels within the tech industry demands a willingness to adapt to new environments, technologies, and leadership styles. Embracing adaptability means being open to learning new skills, methodologies, and approaches. It also involves cultivating resilience to overcome setbacks and the ability to pivot when necessary. 

Moreover, seek out mentors or peers who have successfully navigated similar transitions. Their insights and guidance can be invaluable as you navigate unfamiliar territory. Remember, career transitions in the technology sector are not merely about moving up the ladder but also about evolving as a professional and continuously refining your skill set. 

Embrace change, stay curious, and keep pushing yourself beyond your comfort zone. It’s through these transitions that we truly grow and thrive in our careers. I’d love to hear about your experiences and any additional advice you might have for those embarking on similar journeys. Let’s continue the conversation and support each other in our professional endeavors.

Ritesh Joshi, CTO, Let Set Go

Craft a Detailed Transition Plan

Transitioning from a finance role at a Fortune 500 company to becoming a technology leader in the AI space was both exhilarating and challenging. I had to immerse myself in a completely different industry and learn new skills from scratch. 

During my transition, I focused on acquiring new technical skills through courses and self-study, while actively networking within the tech community. Simultaneously, I developed a business plan and worked on building my own AI app, which served as a concrete goal to drive my transition forward. 

One piece of advice I’d offer to others going through a similar transition is to create a detailed transition plan. It is a slow process, and you have to map out the steps needed to acquire the necessary tech skills. Having a clear plan helped me stay focused and motivated, guiding me through the uncertainties of transitioning into a new career path.

Dhanvin Sriram, Founder, PromptVibes

Cultivate Empathy and Curiosity

Transitioning from a technical specialist to a business owner was a significant career leap that broadened my perspective on leadership and the essence of technology in solving real-world problems. Leading a career development platform, the challenge wasn’t just about employing technology effectively but understanding the profound impact it could have on individuals’ careers and lives. Through this transition, I’ve learned the paramount importance of empathy and adaptability. 

My piece of advice for leaders navigating similar transitions is to remain endlessly curious. Your willingness to learn, not just about technology but about people and the diverse landscapes they come from, will be your greatest asset. Be prepared to listen more than you speak and to encourage a culture of openness that invites innovation and fosters growth.

Amit Doshi, Founder & CEO, MyTurn

Embrace Humility and Seek Growth

My significant career transition came about when I moved from heading teams and a department to founding and leading TechnoLynx—a software R&D consultancy company. While the team lead and department head roles helped me to refine my leadership skills, making the switch to founder and CEO was still a monumental leap.

One of the most notable jumps was the shift in scope and responsibility. As a team leader, I managed and guided a specific group within an organization—ensuring they were aligned with the company’s goals and objectives to deliver high-quality work. Although I was involved in strategic decision-making, the ultimate responsibility for the company’s direction and success did not solely rest on my shoulders.

Now, as founder and CEO, the stakes are significantly higher. Not only am I responsible for leading and managing my team, but I also carry the weight of TechnoLynx’s vision, strategy, and performance. Each decision I make directly impacts the trajectory of the business, our clients, and team. This level of responsibility is significant, but it’s incredibly rewarding to see the direct impact of my leadership on the company’s growth and success.

One piece of advice I would offer to others navigating similar transitions is to embrace humility and seek opportunities for learning and growth. Transitioning from a team leader to a CEO requires a mindset shift from focusing solely on the success of your team to considering the broader implications and long-term sustainability of the entire organization.

It’s essential to recognize and be comfortable with the fact that you won’t have all the answers. By surrounding yourself with talented individuals, seeking mentorship from experienced entrepreneurs, and being open to feedback and constructive criticism, you’ll be better equipped to navigate the challenges and uncertainties that come with leading your own company.

Balázs Keszthelyi, Founder & CEO, TechnoLynx

Learn and Embrace New Perspectives

Transitioning from a hands-on product builder to a YouTube content creator marked a significant shift in my career trajectory as a technology leader. This journey taught me the importance of adaptability and leveraging my existing skills in new, creative ways. 

My key piece of advice for others facing similar transitions is to embrace the learning curve. Dive into your new role with curiosity and an open mind, because the skills and experiences you’ve accumulated are your strongest assets in navigating new waters. Always remember, it’s not just about what you’re moving from, but the new perspectives and opportunities you’re moving towards.

Justin Silverman, Founder & CEO, Merchynt

Set Hard Deadlines for Role Transition

Don’t sail with feet in two boats. This is for leaders who are navigating an internal transition as technology leaders. The natural thing to do during the transition is to manage the previous role and the new role at the same time. 

However, from my personal experience, it will only make the transition harder and longer. It is better to create hard deadlines for the transition, forcing yourself to appoint replacements for your previous role and move completely to your new leadership role.

Siddhartha Gunti, Co-founder, Adaface

Stay Flexible and Pursue Innovation

Yes, as the CEO of Taskade, I’ve navigated our significant pivot from a real-time organization and collaboration tool to an AI-first platform centered around AI agents and automation. This journey was both challenging and exhilarating. Embracing change, we dove deep into AI, believing in its potential to revolutionize productivity and collaboration. 

My piece of advice? Stay flexible and be fearless in pursuit of innovation. Trust in your vision and be prepared to lead your team through uncharted territories. This mindset not only guides us through transitions but also opens doors to unprecedented opportunities and growth. Remember, the future belongs to those who are brave enough to reshape it.

John Xie, Co-Founder and CEO, Taskade

Admit Knowledge Gaps and Delegate

One piece of advice I have for transitioning leaders is—admit that you do not know it all. For a long time, while developing and growing my business, I was pretty much working on my own. That unconsciously enforced in me a habit of doing everything related to leadership on my own, be it recruitment and employee management, marketing, client engagement—even dealing with clients personally. 

But when I shifted gears and transitioned to a new subsector, I realized that not all of my knowledge is transferable, and that some processes cannot be done by myself. Instead of trying to do everything, it’s better to rope in the experts and let them guide you or take over some aspects of management themselves. It’s also better to recognize the strengths of your team and harness them to play a bigger role in business development.

Manasvini Krishna, Founder, Boss as a Service

Commit to Lifelong Learning

Transitioning from a technical specialist to a technology leader involved not just a change in responsibilities but a profound shift in mindset. The technical skills that had been my foundation were no longer the sole drivers of my daily activities. Instead, I found myself steering projects, leading teams, and making strategic decisions that would impact the future trajectory of the organization. This shift required a new set of skills—leadership, strategic thinking, and an understanding of business operations—that were not as emphasized in my previous roles.

The most significant transition came when I founded Boardsi, moving from a technology-centric role into a position where I could influence the direction of an entire company. This leap into entrepreneurship and executive leadership was both daunting and exhilarating. It tested my abilities to adapt, learn quickly, and apply my technical background in a broader business context.

For those navigating similar transitions, my primary piece of advice is to embrace the concept of lifelong learning. The technology field is perpetually evolving, and the skills that make you a proficient technical specialist today might not be the ones that propel you into leadership tomorrow. Engage in continuous education, whether through formal courses, self-study, or mentorship. This commitment to learning will not only enhance your technical skills but also equip you with the leadership, business acumen, and strategic thinking necessary for successful transitions.

Moreover, don’t underestimate the power of networking. Building relationships within your industry can open doors to opportunities that align more closely with your evolving career aspirations. Networking can provide you with mentors who have navigated similar transitions and can offer guidance, support, and insights based on their experiences.

Martin Rowinski, CEO, Boardsi

View Unknowns as Growth Opportunities

I’ve dealt with job loss in the past due to company restructuring. This career transition threw me into the unknown. Despite feeling lost, I remained productive by revamping my resume and reaching out to my network on LinkedIn. During my job search, I also utilized my time to focus on activities I hadn’t had the chance to pursue before.

One valuable piece of advice for others navigating similar transitions is to embrace the unknown as an opportunity for personal and professional growth. Take this time to reassess your career goals, explore new avenues, and acquire new skills. Stay connected with your network, as they can provide support and potential leads. Additionally, remain open to new opportunities that may arise unexpectedly.

Rubens Basso, Chief Technology Officer, FieldRoutes

Push Through Negative Emotions

During my transition from a technology leader, I observed that continuous learning and adaptability can help immensely. In the ever-evolving tech industry, both skills work like wonders and make you capable of any role. The human mind is an incredible thing. It produces the results that you want. 

When I was planning my transition, I started to feel anxious, and my mind also began to react in that way. You have to make yourself understand that nothing in this world is impossible to learn and implement. I may sound like a motivational speaker, but this is exactly what I felt during my transition. I am not saying it was all sunshine and rainbows. 

Staying ahead requires a commitment to ongoing education and skill development. It often turns out to be difficult and makes you regret your decision. But stick to it. Improve through training programs, online courses, and networking opportunities, and stay abreast of emerging technologies.

Saikat Ghosh, Associate Director of HR & Business, Technource

Leverage Networking Before Transitions

After 27 years in the tech industry, I resigned from my corporate job at LinkedIn as a data science leader to start a new career. As much as I enjoyed the excitement of being at the forefront of AI at an internet social media company, I was ready for something different.

I realized that my strengths and interests went beyond technology. I had also wanted to pursue my broader interests in entrepreneurship, coaching, and marketing in my career.

I’m happy to have taken the leap from big tech to launching and growing my own coaching practice over the past year.

Throughout this transition, I’m grateful for my professional network. My network has helped connect me with clients, partners, and advisors for all sorts of opportunities.

Now, when I coach other people in tech, I also advise them to nurture their professional network well before they make a big career transition.

Networking may not always come naturally to engineers and technical workers like myself. However, a person who builds a solid network throughout one’s career will have a vital asset to provide much opportunity and support for all types of career transitions.

Jimmy Wong, Entrepreneur and Coach, AI Jimmy

Realize Debugging Extends Beyond Code

During my transition from a social sciences degree to a STEM degree, I encountered a unique blend of challenges and opportunities. Initially, I believed success in the technology world hinged solely on mastering programming languages and algorithms. However, as I delved deeper into leadership roles, I realized that the principles of “debugging” extended far beyond code and into management.

Embracing the art of debugging in leadership meant acknowledging and learning from mistakes. Just as in coding, where bugs are inevitable and essential for growth, I recognized that making mistakes was an inherent part of leadership development. Each misstep provided invaluable insights into team dynamics, project management, and personal growth. I made sure to catalog my “bugs” and use this knowledge to improve my management skills going forward.

Habiba Elfass, Marketing Coordinator, Achievable

Align Purpose with Career Moves

After over two decades of leading technology teams through many transitions, I’ve learned that the key to navigating any major career shift is to stay focused on your purpose. 

As technology leaders, it’s easy to get caught up in the day-to-day challenges of a role. But when you’re considering a transition, take time to get clear on why you lead in the first place. What unique value do you provide? How do you want to grow? Let your driving motivations guide you. With purpose aligned, the right next step will reveal itself. 

For example, early in my career, I jumped at an exciting promotion without considering how it fit my strengths. I ended up overwhelmed and had to reset. Now, before any move, I reflect on my core talents and how I can best leverage them going forward. This focus on purpose has led me to positions that energize me and amplify my leadership impact.

Chris Riley, Founder, Cuppa AI

Avoid Imposing Old Systems

As a serial entrepreneur in the IT and tech development space, I’d say my entire career has been one long transition as a technology leader. Despite the fact that your role might be similar from company to company, I’ve found that it is still a pretty steep learning curve and a different playing field when you make the jump from the familiar to the new. 

That said, one thing that I would caution others about is to avoid trying to force your old systems and ways of viewing onto the new organization and the new role—a temptation that I’ve had to fight against numerous times. You have a good system, something that works well, in your old organization, and you’re going to want to do the same at the new one, even if only subconsciously, but you have to fight that instinct and take the new opportunity at face value if you want the best results.

Kate Kandefer, CEO, SEOwind

Upskill and Tackle New Challenges

I’ve gone from being a programmer to being a business owner with the idea of sticking a tablet to the wall. 

Over a dozen years later, I own a hybrid workforce management solution business and am seen as a thought leader in the hybrid workforce industry, as we’ve been around since well before COVID-19. What this has meant is that I needed to fix a rather strong asymmetry in my skill set and experiences, as while I knew the tech inside and out, I found running a business to be a whole new set of challenges. 

My advice for those making the jump to entrepreneurship in tech is not to sell yourself short on other aspects of the business when you do. Sure, I didn’t know how sales worked, but I managed to teach myself online as we went. You can upskill to competent levels in many disciplines in a relatively short time, so don’t let not knowing how to do something on the far end of your transition stop you from going for it.

Dragos Badea, CEO, Yarooms