Five Good Ideas ®

Five Good Ideas about bridging the age and culture gap for the new workplace

Published on 28/03/2019

There is a big shift in the workplace underway right now: younger generations are replacing the large number of current leaders who are retiring. And as this group of young people navigates their way into the sector, they also have to deal with the many myths and stereotypes that seem to follow them everywhere they go. Nation Cheong and Agapi Gessesse attempted to dismantle these myths and share their ideas how to engage, include, and support young people so that they become authentic, strong, resilient, and accountable leaders for the future.

Five Good Ideas

  1. Acknowledge and reflect values, urgency, and confusion
  2. Start with career mapping to set a path for your younger workers
  3. Inspire buy-in and loyalty by having a clear learning agenda and intentional opportunities to apply personal assets and skills
  4. Create coaching and mentorship opportunities with a broad network of experienced workers
  5. Cultivate and encourage entrepreneurship through training – balancing autonomy with developing new competencies


  1. ONN Report Leading Our Future
  2. Mowat report Shaping the Future
  3. The Deloitte Millennial Survey 2018
  4. Blog post by Giselle Kovary, founder of NGEN Performance (a Canadian organization that does research on generations in the workplace with Canadian data) talking about the differences between millennials and GenZ
  5. HRPA (Human Resources Professionals Canada) open source document Workforce of the Future: Emergence of Gen Z


Full session transcript 

[Nation]: Every so often, life gives you an opportunity to stop and take stock of where you are in a point in time and appreciate how you got there. This is that moment for me.  And you will understand why as we continue to share with you our experience in this framework of talking about bridging the gap, both the age and cultural gap for the new workforce.

I will start a little bit by saying that I had no intention on being here today. Not that I had no intention on showing up for today’s event. This was not my life plan. I had no intention on being in this sector.

I had a ridiculously trite idea of being an artist, painting, writing fantastic poetry. That went in a different direction very clearly. I didn’t expect to be doing this amazing work that I feel quite privileged to be doing today.

It happened because I walked into the doors of a community service agency in downtown East, known as Dixon Hall. I didn’t have a penny in my pocket and needed something to do because I was going stir crazy. Someone had a contract at the time and said, “Do you know about this thing called the internet? Do you think you can teach some young people and some seniors how to set up an email and communicate with folks?” I thought, “I can do that for sure.” I had no idea what I was doing, but I knew I needed that 2,000 dollars and I was going to make myself learn how to do that.

That was the beginning of my journey, and it has led me to where I am today and my relationship with Agapi. We’ll talk more about that.

[Agapi]: Most immigrant families — or East African, I am East African — they want you to either become a doctor or a lawyer. I told my mom, “Okay, well I want to become a lawyer.” And she was like, “No!” She took me to 1000 Finch. I don’t know if any of you is familiar with 1000 Finch.

I was 12 years old and we sat there for the entire day. The lawyers kept coming up to us, “You need a lawyer?” “You need a lawyer?” “You need a lawyer?” And my mom asked, “Do you want to be one of them?” She said, “Helping people doesn’t pay bills. So, if you want to help people, do it on your own time.” Growing up I thought, I am going to have to do something else because helping people might be something I have to volunteer for.

For my first-time real job, I worked at a bank. I thought, “I am going to help people become financially free.” Also, I volunteered. I called the latter, my five to nine job, because after I left my “real” job, I would go and volunteer at Toronto Community Housing.

United Way had a program called City Leaders that was for people who were working or volunteering in the social service sector and wanted to do that work better. I was really passionate about helping people because of my own life trajectory.

I had a pretty awesome childhood, but at 14 years old my mother passed away suddenly. It changed the trajectory of my life as a young person, and I would, in social service terms, be deemed an at-risk youth.

I was really passionate about helping other people even in the midst of my struggle. I entered into this program but didn’t really know what United Way did at all. I knew just the signs, “Without you there is no way.” With the City Leaders program, I was able to have access to this organization and see people who looked like me.

Nation was at YCF or transitioning into United Way. I always saw him in community and thought, “Well, he looks like he’s well fed!” Later, I was introduced to a gentleman named Emmanuel Mellis, an East African like myself. It made things real for me because we were from the same culture. I saw him in this role and I thought to myself, “Well, all of these people seem to have pretty well-paying jobs.” I could make this a career. That is what I did and how I’m here today.

[Nation]: City leaders, that was 2008, 2009.

[Agapi]:  Yes, it is when it merged.

[Nation]: Okay, so point in time, 2008, 2009. Travel back to me entering into Dixon Hall around 1997. I’ve got a drum on my back. I know how to play music and I am offering to volunteer. And then somebody offers me this contract, which I took.

Dixon Hall was an organization, a very contrasting story to Agapi, that didn’t necessarily reflect me. It was a predominantly white organization. The executive director, who became my mentor and a father figure to me, was a dashing blue-eyed, blue steely-eyed and silver-haired gentleman by the name of Bruce MacDougall.

I was super suspicious of him for awhile because I thought, “You’ve got to be a police officer.” That was my mindset at the time. However, he was someone who had enough of his own values and saw enough potential in a number of us who benefited from his care and leadership. He kept pushing us, putting challenges and opportunities in front of us saying, “I think you can do that.” “Step up.”

How many folks in this room have a post-secondary education? Wow. I have a Grade 12 education. I made it to university when my second child was on her way. I was 20 years old and that took my life in a completely different direction. This is an important point for the conversation. Who we value, what skills we value, and who shows up at the door with what credentials that say you are worth my time.

I am starting to lay the challenge on the ground of how we begin to bridge the gap and create spaces for folks that enter into our organizations, our spaces, and how to maximize their potential.

I had the great luck to be in an organization that had social values that were centered in equity and anti-racism. Many of the folks in senior leadership did not look like me. There was no person of colour. I think that the person that was head of finance was Chinese. Everybody else was primarily of European descent. The frontline workers, as it is in many organizations, were predominantly people of colour. And that was my entry point.

The first point is about the ability to see beyond our traditional markers of value and qualifications. I’m a testimony to that right now.

In my journey at Dixon Hall, a number of challenges were put in front of me. I did them well enough that I managed to make it to a manager’s position. They threw an Excel spreadsheet in front of me and I thought, “This is it. I’m out the door. I’m gone.” I won an award that year for Best New Manager because I took on a spreadsheet and I actually figured out how to do it. I knew what I was doing with a little bit of coaching. Excel helps because all the formulas are built-in. Once you learn how to use it, you can develop that skill quite easily.

This is another example of someone having enough faith in an individual who does not have a post-secondary education and is not coming through the traditional pathway. Puts a challenge in front of them enough for them to stretch and demonstrate their capacity to take on the challenge and prove to themselves and to the organization, “I can do this work.”

That work lasted for almost nine years. In 2006. I answered to a unique opportunity called the Youth Challenge Fund, which was a partnership between United Way, the city and the province of Ontario to respond to what was a peak point of youth violence happening in downtown Toronto, but also connected to young people in the inner suburbs. And that is how our life paths started to weave together.

[Agapi]: When I was at Toronto Community Housing volunteering, I helped them with the youth engagement strategy. They wanted to engage young people in a different way and I volunteered to help with the strategy. Once we were done, they were like, “Hey, we are going to take this on the road, to three or four difference cities across Canada if you want to come with the director and present it.” I said, “Yeah, sure.” All the while I am in the City Leaders program.

An important point, you have to expect more of young people in order for them to rise to the occasion. For example, on the plane ride back from our last city, the director turned to me and said, “I just can’t believe how you presented.” She was really surprised at what came very naturally to me and I thought, “Well, do you think I’m dumb?” “Why wouldn’t you expect that?”

That led to her turning to me, “This is not what I had expected out of this experience with you.” “I have already spoken to some folks and you should think about coming to work for us.” Remember, I am at CIBC, “I am making people financially free.” My answer was, “Oh, thanks love, I’m okay.” “Oh, no, I think I’m okay.” “I’m at the bank, I’m making money, I’m good.” In hindsight I was making pennies.

Part of the reason why I rejected the opportunity at first was, “You didn’t even think I could do this, so why would I want to work for you?” Later, I thought, “Well I’m going through the City Leaders program but it is coming to an end.” After careful thought, I took the job at Toronto Community Housing. I started as a youth mentor and quickly was given other assignments.

Another important point, I was not given title but I was given assignment. I did it really well because I wanted to strive. I had a manager who would come to me and acknowledge, “I know this really, I know it sucks that you have been doing this for x amount of months and your pay has not changed, but I really think that there is something you can learn here because you are hungry and you want to learn and I want to be able to cultivate that.”

This manager took me under her wing and taught me the ropes. She had the job that I was doing prior to her promotion. She sat down with me weekly and asked, “What do you want to do?” “Where do you see yourself?” “Because at the end of the day if HR says, we are dissolving this thing, what is your plan?” “How can I get you where you want to go?”

Later, an opportunity arose. It is when Nation and I, again, weaved back together. I had graduated City Leaders. The program changed my life. It introduced me to people that made me change my mind about my career and lifted it to where it needed to go. The folks at United Way were putting a call-out for coordinator for the City Leaders program. I applied and Nation interviewed me for the role. I went on to run City Leaders for about three or four cohorts.

[Nation]: The significance of this is the following. City Leaders existed within a broader strategy to foster greater youth engagement. It took, at its onset, a programmatic intention. How do we get more programs that foster community engagement and create youth leadership opportunities for young people?

I was part of the leadership of the Youth Challenge Fund. We knew that we had a very small window to go beyond just programmatic interventions. If indeed we were going to make a significant, sustainable impact with this very significant, but small, finite pot of money, in a very small point in time. We had to double down on leadership. We had to double down on the skill sets and the mindset of young people who would take the work forward wherever they go.

That is what, in many ways, Agapi and other fellow City Leaders represent. There are folks who are now at Mars leading the innovation hub. Folks who are working with TDSB to address education inequities. That was our North Star. The leadership was really the objective as much as the programs and getting the money out into community.

The latter points to the idea of intentionality. You need to be clear about the intention of engaging or outreaching young people in your organization or programs. Is it to check a box? Because you have a diversity quota? Because that will lead to a certain experience and certain outcomes. If it is really about cultivating the leadership of tomorrow and recognizing the lived experience of folks who are coming from very diverse perspective. If this is part of the value that you as an organizational leader, change-maker or gatekeeper see, then that changes the approach through which you invite young people into your organization and support them on their leadership trajectory. Support is about understanding what is the vision for the young person. Does it align with the organization? Support is also about helping them to see that in the very early stage.

Thinking about what assets they can gain within the organization. Whether they will stay or move on to another organization. What assets can they gain? What responsibility as a leader in my organization, someone with influence, am I taking to ensure that? Understand those assets and the desired growth or skills.

City Leaders as a program was a response to the sector’s acknowledgement that there is a need for leadership coming out of community that understood community’s needs. It was a program designed to prepare young people to enter into the sector. I think over 200 individuals went through that program. One of the outcomes of that program was resoundingly better prepared individuals.

However, the one thing, coming back around intentionality, that we did not do well is that we did not complete the path back into the sector. We thought through the skill and relationship- building and networking, but not the complete journey.

As you continue your work, think about the end goal. How does an individual continue to build and grow either within your organization or outside of your organization? How do we leverage our channels, network and influence to ensure folks have a place to go?

Later, one of the other initiatives that came to life is an organization called CEE, which Agapi is now the executive director for. It is quite poetic. As I said, there comes a point in life where you get a chance to stand back and appreciate where you are. CEE is an organization that was incubated out of that Youth Challenge Fund investment. It is now an emerging organization I would say, focused on the needs of young people in community. It is a testimony to the ways in which an organization sets intentionality about building leadership capacity and puts a learning framework around how you build that individual or those individuals’ capacity.

You set a bar of accountability as Agapi pointed earlier. These are brilliant people coming into our organization. Don’t undersell them. Recognize their full potential and continue to put opportunities in front of them that build their confidence. It translated to a graduate of City Leaders now at the helm of an organization that we incubated back in 2010, 2009. It is a poetic moment to be standing with Agapi here to talk about that journey of cultivating talent with intentionality and creating a learning framework to support individuals to build their capacity and step into a sector to achieve their aspirations.

[Agapi]: I will use examples. During my time at United Way, when Nation was interviewing me, he said, “Well, what are you going to do after the six months?” He prepared me from the beginning, “It may or may not pan out.” Luckily, the six months’ contract turned into two and a half years. As the contract was coming to an end, management at United Way said, “Hey, look, if you need time off to go look for other jobs, or go on interviews we are open to helping you do that.” Also, they took a look at what other things were happening in the organization and where they saw me fit. I was temporary on the neighbourhood’s team and later had an interview for resource development, which is fundraising.

Being at United Way, I realized that community and resource development spoke two very different languages. I remember going to an interview at resource development and they asked me a series of questions that I could not answer. I had been with the organization for two and a half years and did not have the perspective on fundraising.

I started to get intentional. I said, “Well, I want to become a leader of an organization.” “I want to lead.” “I want to be in management.” In order for me to go there in the social services sector,

I should probably learn the skill of finding some money. I was intentional about it. I went and worked for a hospital foundation for a year to gain experience. I very much disliked it. For the first time in maybe eight years, I had stepped out of what I was passionate about. But I knew it was necessary for my growth. I told myself, “I will do this for a year and soak up as much as I can and be prepared for my next move.”

The way that the current workforce is set up, with more contract work and not full time position, reinforces the myth that young people are not loyal in the workplace. Using my experience, I would have loved to stay at United Way but the contract was over. However, United Way made the transition a lot smoother.

[Nation]:  Some of the things that have inferred in our conversation that I want to make explicit are my own lessons in working with young people. Every year, I would set a goal, to open a door for another racialized individual to get into this sector. I held myself responsible for that. It was my aspiration.

What it takes to do that requires discipline, ethics and authenticity. The times that I failed is how I learned those lessons. When I was not being completely authentic with individuals for whom I had the best intentions for, they reflected back to me, “I expect more from you.” “I expect higher of you as someone who represents community in this organization that I don’t know that I belong to or I have a place in.” What it means in Agapi’s example, is the ability to meet folks in very real terms in what we have come to refer to as the gig economy.

I would encourage, again based on my own lessons, those who are influencers, gatekeepers, hirers, to look at young people coming into your organizations not from a transactional perspective, “What can I get out of you in this moment?” But to see the full person. The discipline of seeing beyond the transactional opportunity, with an individual who has skill sets to offer, puts you in the mindset to say in a very authentic way, “There may not be another pivot point within this organization beyond this point, but I’m committed to your growth.” “Tell me, where do you want to go from here?” And that becomes the plan around the individual. It becomes part of the learning plan and the challenges that you put in front of the individual.

Many young people are passionate about their community or a particular issue but don’t necessarily see at that point in time the broader system. The importance of finance, governance and all the elements that keep an organization together. What I have learned along the way as more and more young people ask me how to get into the sector or for mentorship, is to ask, “Do you know what it means to be a leader, beyond what is driving you and your passion in this moment?” Because it goes beyond just showing up and being with the youth on the basketball court or hanging out and learning. It is part of the work but leadership is helping emerging leaders in our community to understand, “Here is the trajectory that is in front of you. Where do you want to go and how can I help you?”

And if it is a one-year contract, a six-month contract or a year-and-a-half contract, be very intentional with those individuals and say, “Here is a job description. Here is what is expected of you.” And check in, “Here is your learning journey that is designed to meet your leadership aspirations.”

To summarize, ethics and authenticity is really critical for young people who are stepping in the workplace. They understand they are in a precarious world. We as leaders in organizations can offer some level of certainty or predictability beyond the one-year or one-and-a-half-year contract.

  • First, we need to really support the leadership of young people who are entering into the workforce.
  • Second, you foster loyalty by demonstrating care, going beyond the transaction of simply hiring but to make sure you meet your deliverables, check-in and performance evaluation.

We have to really think about the leadership of our organizations. The millennials are the largest demographic right now. Of all the things that you read on the Internet, there is a plethora of TED talks and articles on millennials, one thing rings true for me. They are not a monolithic group. Our tendency as organizational leaders, as human beings, is to simplify and put people in boxes. Resist that temptation. Because the young people between 29 and 40 right now, depending on immigration status, race, sexual orientation, Indigenous status, all have a different reality and pathway within which they are navigating.

Resist the temptation to generalize who and what a millennial is. Most of those things are not true. The socioeconomic factors related to millennials are true writ large. But how young people between 29 and 40, which is the largest workforce here, think, make decisions and build relationships differs depending on what your particular context is.

[Agapi]: I agree.

Another important point to know is that our generation and also Gen Z, we don’t like process. We just want to get it done. Similar to Nation, one of the things that I do with the folks that I work with is to sit down and ask, “Okay, where do you see yourself?” “Do you want to eventually be a manager?” “Where do you see yourself in this thing?” And sometimes people say, “Oh, well I run a non-profit outside of here,  it is really grassroots” or “I am doing advocacy.”  I am extremely transparent because transparency demystifies the process.

Fundraising, for instance, if we have a fundraising goal, I make it very clear to the entire team that it is not a “me problem.” Rather, it is an “us problem.” You will be very surprised at how quickly people will rise to the occasion. You can be transparent and say, “This is the budget. Go make it happen.” And 99% of the time, at least the young people that I work with will come back with something brilliant.

Transparency is something that is really important for young people and also the ability to understand why things are the way help us get to a place of understanding.

[Nation]: We are going to wrap up really quickly now. I will walk through the five things that we think are really critical for change-makers, for folks who open doors or influencers.

  1. Appreciate that young people are in a place now where they are less well off than the previous generations. Economic security is not a promise for young people right now. From research going back to 2017 conducted by Environics, Circle Foundation, RBC, and a couple of other organizations that are escaping my mind right now, the number one priority for young people now is: financial security. For previous generations, it was family or children. The ability to save money and potentially a home is top of mind. When you are bombarded with views of where the market is going, the gig economy, an appreciation of what that might mean for the individual sitting in front of you and being able to meet them in that place of uncertainty is an important step of relationship-building and fostering trust, loyalty with your potential colleague.
  2. Start the relationship with career mapping. Set a path for younger workers based on what their aspirations are, whether or not it is within your organization or other places. What is your career path or aspiration? Why are you in this? And helping folks to see the full potential, your passion, drive, and where those skill sets can translate into other sectors beyond the sector within which they are entering. It is a critical step you can take forward and practice as you leave this door.
  3. Inspire buy-in and loyalty by having a clear learning agenda with folks who are coming into your organization. Provide intentional opportunities to apply natural assets for folks to continue build their skills.
  4. Create coaching and mentorship opportunities, not just one-to-one but with a broad network within your organization and outside of your organization. The mentorship and networking opportunities can expand a young person’s understanding of all the opportunities within the organization. Many organizations have a finance department, an IT department, some can afford an HR department and/or a marketing department. The degree to which folks can connect and expand their understanding of the work within one organization adds value to that individual’s experience.
  5. Cultivate and encourage entrepreneurship. I know that is a new buzzword, but if we really believe that innovation is necessary for us to come up with new ideas, practices, processes to respond to complex problems, tap into the innovation and mindset of young people who will challenge historical ways of doing things. Help them maximize that perspective and add value to your organization.

These are the five ideas that we have to share with you. I am sure some of them are no surprise, but good to hear again.

This transcript has been lightly edited for clarity.

Agapi Gessesse

Executive Director, CEE Centre for Young Black Professionals

Agapi is Executive Director of CEE Centre for Young Black Professionals, an organization dedicated to addressing economic issues affecting Black youth. She is passionate about CEE’s mission-driven and evidence-based work.

Agapi also served as Executive Director of POV 3rd Street, an organization that helps marginalized youth break into the media industry through training, mentorship, job placement, and professional development opportunities. Through prior work as a fundraising professional, social enterprise manager, and coordinator of youth leadership programs, Agapi has established a record of accomplishment in operations management, program implementation and evaluation, financial stewardship, partner development, and community engagement. Her experience includes positions with United Way of Greater Toronto and the Toronto Community Housing Corporation.

Nation Cheong

Vice-President, Community Opportunities & Mobilization, United Way Greater Toronto

Nation Cheong is a respected partnership builder, strategic thinker, community animator, artist, musician and teacher who has dedicated his professional and personal time to community development strategies with a focus on supporting young people in communities across the GTA. Nation served the Regent Park community for eight years focusing on youth and housing strategies. He went on to become Director of Community Engagement and Grants at the Youth Challenge Fund (YCF). In his current role he oversees the development of United Way’s Indigenous Collaboration Framework, stakeholder mobilization across the GTA, and the implementation of United Way’s inclusive employment strategies.