Every Now and Then, Take a Chance on Something New
I am not a product of my circumstances. I am a product of my decisions.
—Stephen Covey, American educator and best-selling author
Every now and then, it just feels like the right time to try something new. Sometimes the reasons are clear, and other times, they are not. The following quote may help provide some guidance:
Always trust your gut, it knows what your head hasn’t figured out yet.
—(Unknown)
There is no right or wrong formula. I know people who graduated from university, joined a company they loved, and stayed there for more than 40 years. Many were extremely talented and had very successful careers. The majority of us, however, don’t do this. As time passes, something about a role or the company no longer fits. When that uneasy feeling in our gut gets more severe, we should realize it’s time to take action. I always thought of these as defining moments, opportunities to explore what else might be out there for me. I realized that a new role would enable me to acquire new skills and help prepare me for a broader range of downstream opportunities. When I became aware of a better job that I was qualified for internally, I would go after it aggressively. When I felt it was the right time to make an even bigger change on the outside, I didn’t hesitate to jump in with both feet once the right opportunity presented itself.
Most people experience uncertainty whether or not to stay in a job or company at one point or another in their career. It may be due to dissatisfaction with compensation, poor work–life balance, stressful working relationships, a lack of learning, or a myriad of other issues. Sometimes the issues are modest and localized, and we seek only a small change. We may just need to be offered some stretch responsibilities to help us grow. Other times, issues are more severe and long-lasting, and we come to realize we’re ready for something new. Staying at a company just because it is comfortable and known, or because you don’t want to let others down is usually not a good reason to stay. A healthy work–life balance is always important, and the dividing line between good and bad is different for all of us. It is important to take the time you need to understand the true source of your discontent. It will help you prioritize the things that are most important before you make your next move.
Mental health plays a major role in our decision making as well. It might be difficult to pinpoint the root cause of a high-stress level or to determine if the stress is short term and likely to pass, or more serious and likely to escalate. A more severe level of stress usually stems from multiple factors. When mental health is at stake, it is important to seek support and to put yourself first regardless of the internal consequences. Companies are resilient, and they are very capable of moving forward without the services of any one of us.
When you do make a decision to resign, an effort should be made to do so as professionally as possible. The technology world can be a small one, and contentious departures may come back to haunt you down the road. While it is important to be transparent and to share concerns during exit interviews, they should be communicated as constructively as possible with the intent to raise awareness to enable future improvement.
If you receive an offer from a new company and find yourself struggling to make a decision, it often makes sense to discuss it openly with your current employer before signing it back. I always appreciated this from my employees as it gave me an opportunity to address concerns without trying to convince someone to rescind an already signed acceptance.
Well-calculated changes can be beneficial to our careers, so long as they don’t occur too often. A resumé depicting an excessive number of moves usually raises the eyebrows of prospective employers. Many get nervous about an applicant’s ability to make a long-term commitment. According to its 2018 Employee Tenure Summary, the Bureau of Labor Statistics reported that the median employee tenure in the United States is slightly longer than four years. In my case, I worked at six companies (excluding acquisitions) over a 37-year career, averaging just over six years. My shortest was about three years, and my longest almost 10.
I still remember how much I enjoyed my first job at Geac. My boss showed appreciation for my work, I had plenty of opportunities to travel, and I developed excellent relationships with my co-workers. While I enjoyed going into work each day, I started to question the company’s strategic direction. I became less confident in its ability to survive long term, and I was unhappy with my compensation. I understood the financial restrictions the company faced, but I believed strict merit-increase limits should not apply to young engineers who were early in their careers. Geac did not have a well-defined career path structure, so there were no real promotion opportunities, except to move into management. The company made the decision to cap salary increases at 4 percent across the board that year. I was disappointed when I received my annual merit increase of about $1K, believing the contribution I made was worth more to the company than that. I knew my boss struggled with it, but his hands were tied. It was a short time later that I decided to apply for a position at IBM. I was offered a one-year contract that paid more than double my salary at the time. I approached my boss to let him know that I was planning to accept it. He turned around a generous counter-offer that afternoon, but it was too late. It would have been enough to keep me there in the first place, but it was insufficient to turn down IBM’s offer. I signed the next day. Fortunately, I was able to maintain a close relationship with most of my colleagues, and several of them joined me at IBM years later.
The memory of my experience at Geac came back to me whenever I interacted with young, talented engineers who were early in their careers. I was always opposed to offering external candidates compensation packages that exceeded those of similarly experienced high performers who had been with us for years. At times, I was limited by strictly enforced merit-increase guidelines, and the situation was impossible to avoid. Fortunately, more companies now offer managers the flexibility to allocate progression increases in addition to merit increases, to help even out the inevitable inequities that develop over time.
I advanced to a second-level management position at IBM as my 10-year anniversary neared. Despite how grateful I felt for all the opportunities, I began to develop those uneasy feelings in my gut again. I was well compensated and I believed in the company, but this time, I was facing a different set of concerns. I had a major personality clash with a peer second-level manager who was my boss before I was promoted. I had no choice but to work closely with her every day. I had responsibility for product management of our compilers and class libraries, and she had responsibility for leading several of the associated compiler development teams. Each day became more challenging than the next. She was pleasant and supportive as my manager but argumentative and unhelpful as my peer. On one occasion, she instructed her team to ignore any direction they get from product management if they felt they had higher priority work to do. On several other occasions, she publicly criticized the initiatives my team was driving. I tried to speak to her about it but I was unable to break through. In addition to these challenges, I believed future job growth would be difficult and increasingly competitive. It would require an out-of-country assignment, which wasn’t possible for me at the time, and it would mean a full-on commitment to the internal politics that made IBM tick. I came to the conclusion that my opportunities for growth were better on the outside. After considerable soul searching and thought, I decided it was the right time to once again look for something new.
The mere act of exploring new opportunities may trigger events to move faster than initially anticipated. It is important to take such a step only when you are prepared to follow through should the right opportunity surface. Always think about the type of work you are looking for, the environment, and the growth potential. While compensation may be one reason to look for something new, there are almost always other important factors at play. It is best not to be lured in one direction or another by compensation alone.
All career moves, be they internal or external, are associated with some degree of risk, which should be expected and embraced. Without risk, there is little chance of any forward progression. One of my ex-colleagues at Emergis was employed by several large companies since graduating from university about 10 years earlier. I remember him dropping by my office one day to let me know that he was planning to resign. He said he saved enough money to take a shot at starting something on his own. He resigned a week later with little more than an idea, a bit of seed money, and the confidence to confront the risks head on. His company remains a going force today, almost 20 years later. He generates healthy profits and employs a staff of well over 100 people. In a recent conversation that I had with him, he said he would do it all over again exactly the same way. He didn’t think he pocketed substantially more money, but his goal was to teach his kids what was possible with a good idea and an abundance of passion. He gained considerable satisfaction from taking the plunge and turning his dream into reality.
In my case, the risks were smaller, but they were substantial just the same. After leaving IBM, I joined Descartes. I moved to a small company at an executive level and had to learn a new industry that I knew nothing about. I walked away from the security of IBM and the steady career progression it offered to a small startup with a grand vision. I was impressed by Peter Schwartz, who was Descartes’ CEO at the time, and I hit it off with the other members of the executive team. I felt a level of energy that I had not felt in years. There was a thrill associated with the risk, and I was motivated to assume a position that would have a direct impact on the success or failure of a company. I listened closely to my gut and had no doubt that it was the right opportunity for me at that point in time.
The Sound of New Doors Opening
The value of an executive title and the importance of establishing myself as a technical leader in a specific domain became clear to me soon after I joined Descartes. For the first time in my life, I was regularly headhunted for executive roles in other companies. While I had no interest in moving elsewhere at the time, it was nice to know that the skills and experience I was developing were of value to the outside world. Descartes was a well-led company with an ambitious vision. They had no shortage of investment dollars to fuel their growth, and my responsibilities grew correspondingly.
After completing a number of acquisitions, I was promoted to Senior Vice President of Engineering and assumed responsibility for global research and development across several countries. I spent a considerable amount of time on the road and gained a significant amount of global leadership experience. My strategy to become a bigger fish in a smaller pond was paying off.
Figure Out What’s Best For You
While we never know if a move we make will work out as planned, we should take comfort knowing that well-calculated moves made for the right reasons almost always lead down a path that is better than the one we were on. It may just take a subsequent move or two before the final benefit comes into full view. Some colleagues I worked with stayed in the same industry their entire careers and became leading experts in their fields. I often admired their technical accomplishments. Others became senior executives at multi-billion-dollar corporations. Their paths to success were different but most found a need to move around at least a few times.
I worked with some brilliant engineers who had considerable disdain for even modest levels of corporate politics. Some made the decision to become independent consultants, contracting their services out to multiple companies. They were confident enough in their technical abilities to build successful consulting businesses over time. Others took to the skies with their families, regularly moving abroad to take full advantage of remote opportunities or assignments when offered. They were drawn by a sense of adventure, they adapted well to varying cultures, and they became uniquely qualified to assume a broader set of roles upon their return. I have also seen employees burn themselves out. Some recognized that they had to take time off to recharge and to re-evaluate what was most important to them before moving on to their next role. They often returned to the industry with a clearer sense of personal purpose and vision. What they all had in common was recognizing the importance of taking the right risks at the right time.
Broadening Your Experiences
If I worked for a large multinational company for a number of years, I would try to find a senior role at a smaller company or startup. If I worked at a startup, I would look for opportunities at companies that were more established. There were pros and cons to both, frustrations and successes, and vastly different insights to be gained. I appreciated the relative security, formal education, and upward progression that was possible at large companies. I also enjoyed the day-to-day thrill of a startup and the excitement of turning something small into something meaningful.
As I approached my three-year anniversary at Descartes, a changing corporate culture brought on by new leaders and a host of acquisitions made me realize it was once again time for change. I found myself getting more easily frustrated, and some of the issues we encountered made me feel disrespected by certain members of the leadership team. I knew I had to shoulder some of the blame for our various Y2K challenges, but I no longer felt we had the tight-knit team that we had when I first joined. I was feeling less motivated and began to welcome the recurring headhunter calls.
I was looking for a small startup that I could join at a senior level, one where I would have a real shot at taking advantage of the dot.com boom that was taking place. Valuations of many of these startups were through the roof. I followed a company named 724 Solutions that developed mobile Internet banking applications. Shortly after their initial public offering in 2000, they had annual sales of $2M, losses of $6M, and a market capitalization of about $1B. They were believed to have achieved the highest price to sales ratio of any company in history. It made little sense, but it motivated many technologists to find a way to take advantage of the craziness. I guess I was no different.
I had never worked for a company with only a handful of employees before, but I believed I found a great one in ProCure.com. The interview process impressed me. I tried to assess a company by the quality of the people who worked there, and I could tell this was a great team that I would enjoy working with. I had a technical vision that I wanted to drive, and I was excited to put my new-found logistics knowledge to good use. ProCure.com felt like the right fit.
While ProCure.com never became the next 724 Solutions, it did develop into a great learning experience for me. I also built close relationships with many of the smartest people I met in my career. Several of them joined me at RIM in the years that followed and some became my closest friends. The greatest validation I felt was when colleagues were willing to follow me from one company to another.
The best opportunities for advancement may turn out to be internal ones. It requires confidence and drive to take full advantage of those that are presented to us. IBM was famous for moving leaders around from one department to another to help them learn as much as possible about the business. Executives rarely stayed in the same role for long. Those with the highest potential were explicitly targeted to get the broadest possible exposure. They were expected to absorb new technologies quickly, lead their new teams effectively, and improve the profitability of the businesses they inherited. In the 80s and 90s, many of the best technology leaders in the world worked for IBM. The highest-ranking executives learned to ask the right questions to educate themselves quickly, even when they initially knew little about the business they would be leading.
Robert LeBlanc is good friend and was always one of my role models. He was a peer manager at IBM early in my career. Robert was an extraordinarily talented leader who took advantage of every opportunity that was presented to him, regardless of how intimidating it might have been. He assumed increasingly senior executive level positions at IBM over the years. He was responsible for leading multiple development labs, he ran a variety of independent business units, he led technical and software strategy, and eventually rose to lead the company’s cloud business. He became one of the most senior executives at IBM. From my vantage point, no one was less intimidated by a new challenge than Robert.
Patience Is a Virtue
When I decided to leave RIM, I knew my next job would be my last, and I was determined to make the right choice. I had already worked for companies of various shapes and sizes across multiple industries. I was searching for something that offered me a bit of everything. Leaving RIM was tough because I felt like the company had become a part of my identity. I also believed the work we did changed the world for the better. Given the uncertainty the company was facing, however, the time had come for me to leave the new leadership and the rapidly changing culture. With one more move left in me, I was ready to take a final risk, but I was committed to holding out until I could make the wisest possible choice. I was looking for an exciting industry where I would have the opportunity to make a meaningful impact. It needed to be a company with a level of corporate maturity and the entrepreneurial spirit of a startup. I suppose I was searching for a role that encapsulated the best attributes of all my previous jobs.
It felt like a mutually exclusive list, but I was in no hurry. I had no burning desire to leave RIM immediately. Multiple opportunities came my way, and I explored the ones that sounded the most promising. Many turned out not to be interesting enough to warrant any serious consideration.
When the Dematic opportunity eventually surfaced, it immediately felt right. Dematic was a global leader in warehouse automation, and my early experience in logistics attracted the attention of an executive recruiter. The company had been around for almost two centuries, but it was continuously reinventing itself. It was private equity owned, set up for growth, and well positioned to take advantage of an exploding e-commerce market. I believed their mission to revolutionize warehouse automation was as significant as RIM’s quest to revolutionize mobile communications. Software was not Dematic’s focus, but they recognized it to be a critical component of their future success. They were looking for a leader who could transform software into a major competitive advantage for the company. If I accepted the role, I would be offered considerable funding and latitude to augment the current software team. I would also be given the opportunity to build a new R&D office in my home-town. The main objectives on my plate were to plug the technical gaps in their software offerings and to consolidate a growing list of regionally developed applications into a single strategic platform. I hit it off immediately with the various leaders who interviewed me. The executive team was smart, friendly, and on a mission. It didn’t take me long to feel the sense excitement I was craving. Once again, there was no mistaking what my gut was telling me. I believed this was by far the best opportunity that would come around given the parameters I set for myself.
It is important to be patient when seeking a new opportunity and to know what you’re looking for. You should take the time you need to think it through and to talk about it with colleagues you trust. If you start the process with a clear mind and a sense of purpose, you are less likely to waste your time chasing opportunities that don’t offer what you need. When the right opportunity does come along, you should be prepared to jump in with both feet.
The majority of technologists who rise to executive-level positions follow career paths relatively similar to mine. They move around every now and then, they take well-calculated risks, they gain experience from companies of varying shapes and sizes, and they commit to learning as much as possible through each step of their journey. Those I respected most were the ones who remained as humble on the day they retired as they were on the day they graduated. They realized how far they had come, but they treated everyone with respect, and they never took anything or anyone for granted.
Key Takeaways
• Take advantage of internal opportunities whenever possible. It is best to resist the temptation to move to a new company until you have explored your internal options.
• Be conscious of the number of companies you work for throughout your career. Too many moves can result in prospective employers questioning your loyalty.
• Pay attention to your stress level and your mental health. Only you can determine the right time to make a move. When your mental health is at stake, always put yourself first.
• No positive move happens without assuming some level of risk. When the time is right, challenge yourself, remain patient for the right opportunity to surface, and embrace the risk head on.
• When you know a move is necessary, even if you make the wrong one, it is likely to set you on a path that is better than the one you were on.
• If you look for jobs externally, mentally prepare yourself to take the plunge when the right opportunity surfaces. The process can move quickly. Don’t waste your own time or anyone else’s if you are not prepared to act.
• Throughout the course of a career, it is a good idea to seek roles at both small and large companies. Unique and valuable learnings are gained from both experiences.