Career Transitions

Have you ever peeked over your neighbour’s fence and daydreamed about what life could be like in that yard? The expression “the grass isn’t always greener” is often used as a warning, but from my vantage point, looking at careers as opposed to courtyards, I believe it’s always worth taking the opportunity to pop over the fence and feel the grass beneath your feet.

Throughout my career as an Executive Search Consultant, I have worked on searches in the private and not-for-profit (NFP) sectors, and while many clients prefer to hire candidates with specific sector experience, others have seen the benefits of considering candidates outside of their sector. 

I spoke with two accomplished HR leaders whose careers have spanned the private and NFP/public sectors. In understanding their personal experiences of moving between sectors and with the benefit of their deep knowledge of human resources and talent acquisition, there’s a lot to learn. They noted the advantages of hiring outside of your given sector, as well as what to look for in a candidate, and how best to prepare them for a successful transition.


Sandra Levy, Chief People Officer

Sandra Levy is the Chief People Officer at the Canadian Olympic Committee (COC). A lawyer by background and an Olympic athlete (two-time Olympian and two-time Pan American Games medalist), her career trajectory has spanned some of Canada’s leading organizations in both the private and NFP sectors. While Sandra valued the experience of working in the NFP space, after a few years, she returned to the private sector as she didn’t want to be “pigeon holed” and overlooked for opportunities simply because of the sector she was working in. For Sandra, it always comes down to the role’s mandate and working for a company that shares her leadership values and focus on culture and human capital. Less than a year ago, Sandra was approached for her current role which brought her back into the NFP sector. Accepting a position with the COC was the “perfect fit” for Sandra and felt like “returning home”, thanks to her years competing as an athlete in the Olympics and the close ties she maintained to the COC. 


Roy Tran, Director of People Experience & Transformation

For Roy Tran, the experience of moving from the private to the public sector was grounded in wanting to give back to the community he grew up in. After a diverse career in the private sector across multiple industries, Roy moved into the public sector to join one of Ontario’s leading Crown corporations. Most recently, he was drawn to working for the City of Toronto as he grew up there and was curious to learn about the City’s inner workings and leverage his skills from the private sector. His role as Director of People Experience & Transformation for the City of Toronto very quickly exposed him to the operations of the City, and while he did face a bit of a learning curve when it came to the City’s processes, he has enjoyed the satisfaction of learning how to navigate a new system. Roy articulated that whatever industry he is in, “the common denominator is people and this transcends multiple industries.” 


The Benefits of Hiring Outside of a Given Sector

Both Sandra and Roy have had positive experiences moving between sectors, and hiring between sectors. Here are some of the benefits they shared:

  • Your Organization Will Gain a Fresh Perspective

While many transition from the private sector to the public sector or a NFP with ease, the reverse doesn’t always apply. There’s a stigma that exists about the public sector being “stuck in its old ways, and not open to change” which can become a major deterrent for those established in the private sector. But that line of thinking is outdated and incredibly limiting. Sandra touted the benefits of hiring outside of a sector, believing the right candidate can bring “good practices, good business sensibilities, and a good sense of urgency and pace.” With a fresh perspective, a candidate from a different sector can help drive innovation and inspire team members.

  • You’ll Introduce New Skills and Experience to the Organization

While Roy did acknowledge a greater tendency for candidates to move from the private sector to the public sector, he highlighted that there are many examples of organizations in the private sector specifically seeking out individuals from the public sector, who bring a deep understanding of the nuances of navigating the government and key stakeholders. These include consulting and technology organizations.

  • You Can Tap a New Pool of Candidates

If you’re only hiring within your sector, your pool of talent is limited. Especially as industries strive to demonstrate best practices for advancing diversity and inclusion, it will be increasingly important for organizations to cast a wide net, and demonstrate a willingness to hire beyond its typical network.


What to Look for in a Candidate Transitioning Between Sectors

  • Understand Their Motivation

To understand if someone is the right fit for a new sector, it’s important to understand their motivation, and whether the position will truly meet their expectations. As an example, Roy was motivated by curiosity to learn about the city he’d grown up in, and he saw an opportunity to leave a legacy in the public sector that wouldn’t have been possible in the private sector. 

  • Analyze Their Previous Experience

When it comes to analyzing someone’s work experience, we need to think more abstractly. While job history and skills are vital, an individual’s outlook, ability to problem solve, and how they treat their colleagues can speak volumes about how they’ll perform in a role, regardless of the sector they’ve worked within. While working in a NFP, Sandra observed that employees often needed to become generalists, due to tighter budgets and limited headcount. Employees were expected to wear many hats, and be adaptable to fluctuating budgets and scopes of work. To gloss over a candidate from a NFP would ignore the potential of finding someone who possessed that adaptability, wide breadth of skills and determination.

  • Find Their Personal Connection

When hiring people from the private sector for a position in a NFP, Sandra and Roy stressed the importance of understanding the personal connection (if any) that a candidate might have. If there’s a deeper motivation, it not only helps to explain the pivot, it also signifies an individual’s passion and dedication to the cause. 


How to Ensure a Successful Transition to a New Sector

  • Know the Culture

Sandra and Roy both underscored the importance of understanding an organization’s culture before making a transition, as this can often make or break an employee’s experience and longevity. To really know what you’re getting yourself into, you need to understand an organization’s culture and leadership history. When moving from the private to the NFP sector, Sandra suggests achieving this through volunteering. A candidate who already has a relationship with an organization will always demonstrate not only an affinity, but a deeper knowledge as well. When moving into the public realm, Roy highly recommends doing your homework. For example, if you are preparing for a role with the City of Toronto he suggests watching City Council meetings on YouTube in order to gain a deeper understanding of key agenda items and how the City operates. 

  • Know the Expectations

When candidates are shifting into a new sector, Sandra discussed the importance of dispelling myths and assumptions, and ensuring a very clear understanding of an organization’s priorities and stakeholders. For example, when hiring from the private sector into a NFP, it was important for Sandra to find candidates who were cognizant of the responsibility and sensitivity around the management of finances, especially in front of donors. For Roy, it’s important for anyone joining the City to understand that in addition to the typical hierarchy of an organization, there is the additional layer of Council and the public view that needs to be taken into consideration. This adds an additional layer of accountability and governance that candidates will need to navigate. 

  • Know Yourself 

When candidates transition from one sector to another, they should ensure they grasp the mandate of the organization and how their specific experience will be perceived. Especially when moving into the private sector, candidates need to market the benefits of their public/NFP sector experience. For example, how they have “moved the needle” including the change management initiatives they’ve worked on as well as the innovation they’ve introduced. Ultimately, Roy believes it comes down to mindset. The successful candidate will have to acknowledge the challenges of entering a new sector and learn to navigate and problem solve while leveraging their previous leadership experience to add value.


Having worked across the private and NFP sectors myself, I’ve been able to develop a network that spans both, which has served me well in my executive searches. I’m able to cast a wide net, and consider candidates and skill sets that wouldn’t have necessarily been obvious or available to a given sector, and find the very best talent and fit. I like to tell my clients, the grass might very well be greener on the other side, and I wouldn’t want you to miss out on that. 


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