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Choosing Your Board With Caroline Riseboro

By July 8th, 2023No Comments22 min read
Home » Choosing Your Board With Caroline Riseboro

A successful company is more than simply having a great CEO. A CEO needs to be backed up by an effective board as well. After leaving the commercial sector, Caroline Riseboro went to work for NGOs such as World Vision and The Centre for Addiction and Mental Health. Her experience in both foundations led her to become the CEO of Plan International Canada. In this episode, Caroline discusses the strategies she put into place when she came to Plan. She stresses the importance of choosing your board carefully, having an effective management team, and teaching them that failure is okay.

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Choosing Your Board With Caroline Riseboro

Our guest is Caroline Riseboro. Since 2016, she’s been the CEO of Plan International Canada that has programming in excess of $250 million on an annual basis and is making a difference right around the world. Welcome to the show, Caroline.

Thanks for having me.

As we start into these conversations, it’s best if our readers have a chance to understand the organization that you lead. Tell us a little bit more about Plan International.

We’re about 80 years old if you can believe it. We are the largest girls-focused NGO in the globe. Canada is one of the larger offices of the Plan family. One of the largest. That’s a unique piece because oftentimes there are not many things we can claim are in Canada that are some of the largest. We raised about $250 million in revenue. We help six million children across the globe, but also here in Canada as well. Our theory of change is based on the issue of gender equality. For instance, we know that countries that are more gender-equal have healthier, happier, and better-educated citizens. They’re usually safer and more prosperous. Our theory of change focuses around tapping into equality as a way to unleash human potential.

That is an impressive mandate and you do it well. How did you come to be CEO at Plan International Canada? Tell us a bit about your background.

I started my career off twenty plus years ago. I started in the commercial sector. I worked for a big ad agency. We were working on products like McDonald’s, Coca Cola, Bell and Home Depot. I remember walking to work and seeing people living in the streets, suffering from addiction or mental illness. I thought to myself, “I can’t keep selling more internet. I want to make a difference.” I stumbled, as many people did 20 years ago, into the nonprofit sector. I started working for what is still the largest charity in Canada, World Vision. It’s also an international NGO. I started doing the direct mail program, introduced the first email marketing.

About ten years later, I was overseeing all of the fundraisings for World Vision. I had a team of about 250 people. We had to raise $280 million a year, which was more than any individual in Canada. After about thirteen years, I felt it was time to do something different. I was lucky to get recruited to CAMH Foundation, the Center for Addiction and Mental Health. It was a cause near and dear to my heart as it is for many of us. I worked there to expand what I would call their mass engagement program, “How do we get more people giving to the foundation at even smaller amounts?” That was important because it was part of the mandate for stigma reduction. From there, I was recruited to come to Plan. Working in the NGO sector and having had lots of experience there, I was asked to consider being the CEO of Plan International. Long story short it, all worked out.

Measuring results, including how you’re achieving your mission, needs to stay as your guiding star. Click To Tweet

As an accomplished fundraiser, how did you make yourself familiar with the diversity of impact and programs that are there at Plan International?

One thing that is interesting about my background is for a couple of years while I was at World Vision, I stepped out of the fundraising space. I was asked to lead the communications, public engagement and advocacy portfolio. It meant I was looking at advocacy at the field level and at how advocacy could accelerate programmatic outcomes. That was my exposure to the programmatic side. It’s a lot more in-depth in my role at Plan. I always say that part of the secret sauce of any great CEO is knowing to hire amazing people that are smarter than you in the areas that might not be your technical expertise. I have an amazing team at Plan, a number of executives that run our program team that are probably the best in the country. I spend a lot of time with them. I learn and listen to them. It’s knowing how to get the best out of the folks who know more than you.

I know that philosophy is one that some people say is difficult to implement at times. I remember working with the board chair who said, “It’s okay if the CEO doesn’t know, but it’s never okay for them not to ask.” Building that team takes real discipline. How do you approach that as a leader?

As you go through your leadership journey, you have to start to ask better questions. When I was mentoring a new VP on my team, I told her that one of the most critical things we need to learn when we take that next step up is that our questions have to become smarter. You have to start to ask more questions. If you’re getting the answers that seem sensical, authentic, honest and make good sense, that’s usually a sign that your folks are doing the right things. Your staff is doing what they need to be doing. If they’re struggling to answer the questions or if they don’t know regularly, that’s a sign that you’ve got to start to lean in and dig in because something isn’t quite right. You’ve got to know which questions to ask that oftentimes relate to the business strategy, goals, leadership and the team. Your questions have to become better thought through.

In terms of tactical advice, how do people get better at asking questions? What advice do you give people about asking deeper or more insightful questions?

A lot of it comes through practice. I have regular updates with all of my direct reports. Sometimes I do skip-level meetings, too. I try to make sure that when I do these updates, I’m speaking 20% of the time and I’m listening to my team 80% of the time. The questions have to get better in the sense that they need to cut into things like, “How are you achieving results? What are the results? What are the interdependencies about the results? What have you thought through? What could you be missing?” You need to fish for information to build confidence that things are on the right track.

The other set of questions is self-reflection and self-discovery questions for the leader that you’re mentoring. You have to make sure that as you’re updating or having times with folks, you’ve got two sets of questions. The last or the third set of questions is joint discovery and co-creation. “What if this?” “What if we did that?” “If we were somebody else and they came in brand-new to the situation, how might they approach this?” That allows you to take a step back and reflect. As executive leaders, we need to make sure that we are asking those kinds of questions of one another more regularly.

Those important conversations lead to a generative culture within an executive team where you’re able to pivot strategy, ask different questions and deliver in a slightly different way. Are there decisions that you’re more comfortable letting your senior management team make now that you’ve been in the role for a few years than when you started in 2016?

Absolutely. The team has progressed. Plan was a different place when I started years ago. We had a different executive team, board and set of skills. One of the first things that any new leader, especially a CEO, needs to do when they first come into an organization is to do a capabilities assessment of their team. They need to know what is needed for the organization and where their team is at. I have more confidence because I plugged some of the gaps that we’ve had. I know that overall we have a great complement of skills at the executive level that maybe we didn’t necessarily have before. It’s easier to put trust in folks because you know that all the skill sets are covered. You have folks that are innovative and want to push the edges. You have other folks that are more risk-averse and they’re going to think through the consequences. You need both of those types of skills. That’s one example along the spectrum. As you start to build out the skills capability of any executive team, you can stand back a little bit more. In the early days, you’re leaning in

What feedback are you looking for from your senior management team as you roll through a year or the deployment of a particular program? What are the types of briefings or reporting that you want to have from them in your one-on-one meetings?

When I came to Plan, I put the first comprehensive strategy and execution plan into place for the organization. Even though Plan was one of the larger charities in Canada, we didn’t have a strategy. I put in this strategy with a real set of joint key performance indicators so that when we are when I am updating with my executive team one-on-one with staff, we have a shared language to look at. One of the first things that I take a look at with them is how we are doing. Ultimately, we’re measured on our results including how we’re achieving our mission. That needs to stay as our guiding star.

One of the other pieces I look for in this, and I don’t think we talk enough about this in this sector, is license. “Does my team feel like they have the license to operate and achieve their goals?” It’s one thing to be able to articulate what the North Star is but do my team members feel that they have the capabilities to get there and that they have the license or permission to do what they need to do to get where we’ve decided to go together? A lot of folks these days don’t feel like they have that license. That’s the other thing I’m always probing on. When I question my team members or when they question me, does everybody feel like they have the license to do their best work?

What do you think gets in the way of leaders in the organization? Whether they’re CEOs dealing with the board or whether they’re Vice Presidents reporting to a CEO, what gets in the way of them feeling that license? What are the barriers that organizations put up?

This is where I’ve tried to work harder on creating what I would call psychological safe workplaces. At Plan, we’ve been bucking the industry trend, which is seen as a stagnant philanthropic market. We’ve grown by 25% over the last years. A lot of it is because we’ve tried to remove some of the barriers and one of those barriers is often the fear of failure. If you’re going to be out there doing new things, of course you’re going to fail. How do we make sure people feel safe after they fail, learn from it and move on? We’ve had failures. We’ve stumbled along the way. We’ve always gotten to the endpoint that we wanted to get to but we’ve had detours along the way. I always say we fail our way to success. That’s been the distinguishing factor between the culture we want to create at Plan. Perhaps that’s what’s happening at some other organizations.

When you fail, have a day of mourning, but pick yourself up the next day and focus on what the learning is and what good came out of it.  Click To Tweet

That culture that accepts failure is something that a lot of organizations talk about. I’ve talked to a lot of CEOs who say, “I want people to be making mistakes. I want these errors of action where people are reaching beyond what we normally do.” They struggle sometimes or they’re frustrated by the fact that the people in their teams aren’t willing to do that. They don’t believe the message that failing is okay. They want to make sure they’ll only go so far out of their lane that they’re confident they’ll be 100% successful. Can you think of a story at Plan where someone went further out of their lane, where a mistake did happen and how you used that as an example to give permission or license for people to be making those kinds of mistakes?

Two things come to mind. Like many charities, we’ve been considering how the digital disruption that’s going on in the rest of the world is going to impact us. We’ve been on a digital journey where we’ve tried to come up with plans to accelerate our digital footprint and lead in this space. We had a few false starts. We worked with a big consulting firm to come up with a plan. It went to the board. The board said, “There’s no way this plan is feasible. You’re asking for way too much money. Go back and redo it.” Would that have been considered a failure? Sure, because you always want to bring something to a board that they approve and you move forward with. In this case, they said, “No, this plan is insufficient.” You know what? We tried and we learned. We got that feedback and we incorporated it in a second time. It’s a solid plan, they approved it and we’re moving forward. We could have viewed that as a failure or we could have viewed that as, “This is a learning moment along the journey.”

Another example that comes to mind is when we’ve been doing something different at Plan. We’re focusing on major gifts, which is unusual for the international development sector. We tend to focus more on the lower gifts but in high volumes. You don’t see a lot of the big philanthropic gifts going to international development. We launched a campaign. We’re looking to raise $100 million from private individuals to match with another $650 million from government donors. We’re about 33% of the way there, which is good news. It would make it one of the largest campaigns in Canadian history for International Development. We had a lot of failures along the way. We had some false starts where we went to donors and ask for a $10 million gift. They came back to us and said, “I was thinking maybe $1 million.” I could have viewed that as a failure. I had to ask many times.

It’s all about how we view these things. The reality is that to get donors giving $1 million to international development is a huge success. We rarely get those kinds of gifts. Yes, we didn’t get the $10 million gift but we still broke ground with some of these $1 million gifts. Much of it is how you frame that. We probably wouldn’t have gotten that large gift if we hadn’t have asked for something larger. I’m a firm believer that the worst thing to do is beat oneself up. When you fail, you have to maybe have a day of mourning. Pick yourself up the next day and say, “What is the learning and what good came out of this?” Focus on that.

That transition or inclusion to major gifts is something we work with clients a lot on. One of the constant refrains we have, particularly when we’re reporting to the boards and how the program is rolling out, is that it’s a process of becoming a place where people see this philanthropy happening. It is a rare donor that wants to be the first eight-figure donor to an organization. If you’ve got people giving it at the seven-figure level, it becomes a lot more likely over time.


It’s hard to feel like a million-dollar gift is a failure. I wouldn’t call that a humble brag because I think that was a genuine story. Those are the good problems to have, a problem of abundance.

Yes, and I didn’t mean it to do a humble brag there. It was so easy to view that as a failure versus success. It’s a success in retrospect, but I can tell you that at the time, it was devastating to be told that $10 million is totally out of the ballpark. You could have a bit of an existential crisis at that moment. It’s funny how it changes in retrospect. I think that’s indicative of the fact that some of our failures are big successes.

It’s success delayed, often. I want to pivot to your board. You’ve done a great job of building an impressive board that reflects the diversity of the country and your core mission. As CEO, how have you approached your work in building that board and how is working with that board changed?

The board has changed radically at Plan. In the last few years, every single board member is new. We have about 12 or 13 board members. As they were doing the recruitment for the CEO, there was board recruitment going on, too. The plan realized at that point that they didn’t have enough folks in the pipeline. They started to get a little bit more serious and thoughtful about that board rejuvenation. I was fortunate that when I joined Plan my board chair was someone by the name of Patsy Anderson. She has had a significant amount of experience sitting on boards in the nonprofit sector, including SickKids Foundation and Roy Thomson Hall, as well as sitting on corporate boards. What I found through that rejuvenation of the board is sometimes you need one or two people that can be talent magnets. They can start the board renewal process.

You need to have a vision as a CEO even though it’s not technically your role or responsibility to select board members that are for the board itself. You do need a vision of what you would like to see from the board. I have a vision where I thought if we want to get into the major gift world, if we want to start to create the platform for investment at Plan, we need a board that would attract those kinds of resources and folks of influence. We started with one or two. It became much easier to have that conversation with number 3, 4, and 5. Then followed 6 and 7, and on and on it went. There is a bit of a snowball effect.

Folks want to be part of a winning team. They want to sit on a board with other folks that they know. If you can start by getting a few people and can articulate a strong vision of the art of the possible, you can start to attract people on you that can give their affluence and influence on the platform that they have. It’s important for us as charities to do that because we’re oftentimes dealing with limited resources. To be able to use and leverage the cache of board members, it’s a win for them. It allows them to do something about a cause that they care about and it’s a win for the organization, too.

As the board has evolved, how have your conversations with them, both in meetings or informally, changed?

When you’re first in the CEO role, you want to give the board the sense that progress is happening. The ship is being captained by someone who is competent and it’s the right person for the job. Those were my early days with the board. Also, in the early days, you get a first shot at saying, “Here’s what I see are the challenges within the organization.” Be transparent with the inertia you might see within an organization because they won’t want to hear that two years into the role. They’ll want to hear it in the early days.

When you have great board members, they want to be part of solving those problems with you.  Click To Tweet

My biggest learning is if you started attracting great talent, they don’t want to be on the board to govern over the financials. They’ll want to be engaged in the board. They’ll want to have those strategic and generative conversations. “Who do we want to be? What’s our place in the world?” They’ll want to feed in. If the board meetings or our committee meetings aren’t a 50/50 dialogue management and board, then we haven’t done our job. Often, folks think, “I’m reporting back to the board. I want to make sure that they feel like things are in good hands.” When you have great board members, they want to be part of solving those problems with you.

That board lifting up the organization rather than monitoring it and sometimes pushing down makes all the difference when you’re trying to grow the revenue or shift the programming. You’ve done both.

I love what you’ve said about that. If you have board members that are there to monitor the organization, you can maybe then stay the course. If you want to do transformational type work, you have to have a board that wants to lift the conversation and the governance.

The importance that we work with that are helping organizations see over the horizon are the organizations that are most successful. A dominant trait of successful organizations in Canada and the United States is able to look ahead. It’s pushing the CEO and the management team to be driving forward rather than to crunch down or present with things as they are as a steady-state. It doesn’t change.

Agreed. There needs to be a good evolution of the discussion and that has to be both sides. That’s why it’s so important that the CEO is always looking with one foot in the present delivering on the current plan. They also need to be spending a lot of time thinking, “Where are things going to be in 3 to 4 years? What do we need to do now to prepare for that?” They need to have a board that supports them and pulls them in that direction, too.

That’s an excellent point. One of the great things or encouraging things about this podcast is that a lot of our readers are people who want to be CEOs of social profit organizations one day. What advice would you give to someone who is maybe 2 or 3 years away from being able to take that leap? What should they be doing to prepare to be a CEO?

Let me say this. I became the CEO of one of the largest charities in Canada at 38 years old. All in all, I was probably one of the youngest people ever to lead a major charity. I’m not telling you this to do a humble brag again, but I’m saying I think in retrospect, I maybe would have taken a little bit more time. I would ask folks to step back and ask themselves, “Why do I want to do this?” These roles aren’t easy. They’re much more challenging than what you might think, particularly if you’re an international role like I am or a national role. You’re spending a lot of time traveling away from home. Is that what you want right now? It’s not just considering career progression. It’s also considering life and stage with family, too.

If you’ve gone through that exploration and said, “I know why I want to be a CEO. I’m ready and I want to make that leap,” I would say there are a couple of things that you need to consider. One is an experience with the board, which is important. You’re moving from reporting into one individual to having a group of bosses. Getting exposure to the board, whether it’s being the staff lead on a committee or sitting in in all of the board meetings, that’s an important experience. It could be even sitting on a board or chairing a board for your professional association or a smaller charity. That governance experience is key to being a CEO.

CEOs these days need to be great talent managers because no longer are you managing or overseeing the work yourself. You have to get the work done through people. That’s another critical experience that you need to have. How have you worked through great people to achieve organizational results? That whole talent management is critical, and being able to straddle the operational and the strategic. That goes back to my point. You’ve got to have one foot in delivering in the here and now, but you have to show that you’re thinking 2 or 3 years out. That’s what boards are looking for. The last piece is looking at those soft skills. You might need some fundraising, program oversight, or financial experience. So much comes down to things like collaboration, relationship-building, and perseverance. Looking for opportunities to build those kinds of muscles is important.

People often give the advice of, “It’s a marathon, not a sprint.” With what you’ve talked about, it reminds me that it’s a marathon that you run as fast as you absolutely can.

Yes, it’s wonderful. There are times you’re going to sprint. The slowest is a nice marathon. Sometimes, you might come into an organization and there are some major issues. You need to run a sprint. The best days it becomes a marathon but there are many days where you’re pushing yourself to go as fast as you can.

Caroline, thank you for taking the time to be a part of the Discovery Pod. You shared some important lessons. One that I want to leave our readers with is as you go through an organization, as you go through your career, your questions have to get smarter. Find a way to be asking those deeper and more insightful questions. You can lead your organization to greater heights. Thank you for sharing that, Caroline.

Thank you for having me.

Great. Thank you.

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About Caroline Riseboro

Caroline Riseboro is an award-winning humanitarian and social justice advocate, recognized as one of Canada’s most influential leaders in the nonprofit sector. As President & CEO of Plan International Canada – the country’s premier girls’ rights organization – she leads a dynamic team of professionals, delivering over $250 million annually in high-impact programming. With two decades of experience leading top-tier nonprofits, Caroline has a proven track-record of taking organizations to new heights, while improving the lives of millions of people both in Canada and around the world. Under her leadership, Plan International Canada has consistently reached record highs, been recognized with multiple awards for culture and performance, achieved ground-breaking fundraising results, significantly increased its reach in Canada and globally, and become the go-to organization for bold and innovative advocacy for girls’ and children’s rights.

As the youngest person to ever lead a major Canadian charity, Caroline consistently strives to find new ways to deliver critical social change, while cultivating a thriving company culture. She has received seven Stevie Awards for Women in Business, including Canadian Female Executive of the Year, has been recognized as one of WXN’s Most Powerful Women in Canada for two years in a row and is a TEDx speaker. Caroline holds several board positions, including as Board Chair the Association of Fundraising Professionals, and has served in governance roles for the Canadian Partnership for Women and Children’s Health (CAN-WaCH), the Canadian Marketing Association and the Humanitarian Coalition. She is a graduate of McGill University and Harvard Business School’s Nonprofit Leadership Program, and is currently pursuing a Master of Nonprofit Leadership from Carleton University.

Caroline’s influence in the sector extends through her voluntary leadership roles. She sits on the Board of the Humanitarian Coalition and CAN-WaCH, is the President-elect for the Association of Fundraising Professionals GTA chapter, and has sat on numerous task forces including with Imagine Canada and the Canadian Marketing Association’s Not-For-Profit Council. She holds a Bachelor of Arts (Honours) degree from McGill University and is pursuing a Master of Philanthropy and Nonprofit Leadership from Carleton University.