091 – Non-Profit Leadership Strategies with Jonathan Bennett

Episode Transcription

David Pisarek: This podcast episode is made possible by wowdigital.com, your trusted partner for non-profit and charity website and design.

In what ways can a meticulously crafted strategy enhance a non-profit leader’s online presence and influence? Welcome to the Non-profit Digital Success podcast.

I’m your host, David, and today, I’m joined by a very special guest, Jonathan Bennet. I’ve known him for a couple of years. He is an executive coach who is deeply invested in shaping North American leaders. As a founder of Laridae and now the guiding force behind ClearlyThen, Jonathan has empowered over 100 non-profit boards with his governance expertise.

Jonathan, thank you so much for joining today’s episode.

Jonathan Bennett: David, it is a pleasure to be here again.

David Pisarek: Yeah. How’s everything going?

Jonathan Bennett: Yeah, you know, just withstanding winter in Canada. So it’s all good?

David Pisarek: Yeah, absolutely.

All right, so let’s hop in. What drove you from a thriving firm, Laridae, to coaching and impacting your leadership style?

Jonathan Bennett: Yeah, so. But over ten years ago, I founded a management consulting firm called Laridae.

It’s based in Ontario, Canada. And over the years, we grew this firm. We became a B-Corp. We served only non-profits right across Ontario and beyond, largely through strategic planning, branding, and communications work.

And years back, I kind of had one of those epiphany moments. I was on a vacation with my wife in Dublin, Ireland, and we were walking around the streets and I was talking to her about, like, my life and, like, who am I and where am I going next? And I admitted that I think I was coming kind of towards the end of this journey.

And I realized in that moment that I really only had kind of one outcome in mind in terms of, like, who I thought would be the next CEO of Laridae. And over the course of the next 18 months, I transitioned out and was able to do a management buyout, and I got to reinvent myself.

So Laridae, still doing amazing things and, you know, encourage folks to get in touch with the team there. But that’s kind of all in the review mirror for me.

Now, these days, I’m an executive coach, entrusted advisor to leaders in the non-profit sector and social purpose businesses right across North America.

David Pisarek: I love working with businesses, organizations, people that care about improving the lives of other people. It’s such an amazing thing to be doing. How are you finding that?

Jonathan Bennett: I just feel, like, so privileged. I mean, you know, obviously white guy, right? I’m about as privileged as you can get, but I also just feel deeply privileged to do the work that I get to do. It’s pretty intimate.

The work I do, it can be lonely being a leader. It can be hard and difficult. And there’s only so many things that you can share with your colleagues at work, your staff, your board of directors.

There’s only so much that your partner at home or friends would be willing to put up with about listening to work.

And so, you know, what do you do after a while? You tend to just bottle it up and you sit on it, and it can become heavy. And that’s when leaders look for folks like me to be able to work with them on the most difficult issues and problems, opportunities that they face.

And it’s a real privilege because I get to be there when they’re thinking through this stuff, when they’re figuring out where to go next and what’s after what’s next.

David Pisarek: Thinking through that vein of thought, how can non-profit leaders find personal and professional fulfillment?

Jonathan Bennett: Well, it’s a taxing place to be leading a non-profit, whether you’re an executive director or you’re just moving up through management ranks, and especially if, you know, you’re in marketing and comms and fundraising.

We have to do an awful lot with precious little. And the creativity that’s involved in being able to drive the course and fulfill your organization’s mission is really demanding.

Attaching that to your own personal satisfaction is really what draws people to the work. And I think what I’ve noticed for leaders is, over the longer period of time, that can change.

And I spend a lot of time with folks, helping them make that be okay, that we can start off all in on a particular organization, a particular cause.

And it’s okay when we hit that moment in our life, in our career, in our journey, that we can step back and let the next person pick up the baton and take that and reinvent ourselves or move on to a new cause that better matches where we’re at now in our life’s journey and the things that we see around us that really inspire us or impact us.

David Pisarek: You know, like, life’s journey, it’s not A to B. It kind of like weaves around and up and down.

And part of that is the hat that we’re wearing at the time versus the hat we want to wear, versus the hats that we’ve worn before and the rules that we’re in and what brings us the joy, what makes us feel like in our soul that something that we’re doing is creating something better.

For me, that’s why I do the work that we do at my agency. Right? We want to help 5000 non-profits impact the lives of 10 million people. Like that is a big area, audacious goal.

I want to push to achieve that. And you need to have a clear mission as an organization, as a leader to go, “Okay, here’s the guiding star. Here’s where we’re going and making the calls, the tough decisions sometimes as to we’re going this way, but we got to go this way now.” Right? And it’s lonely. It can be.

Jonathan Bennett: Yeah, it can be.

And I think for executive directors or CEO’s of small and mid-sized agencies especially, they can feel like it’s all resting on their shoulders and that they’re carrying an awful lot.

And you know, I just always encourage folks that there are folks around them in their community, on their boards, donors and funders.

People are invested in the success of the organization and it’s not everything is on them. And, you know, I suppose further, David, to your point, the longer you’re in a role and the longer that you lead an organization, you can start to enmesh your personal identity or your personal brand as a leader with that of the organization.

And, you know, you don’t have to be in and around the sector for long to see longstanding leaders really struggle when it comes to retirement. They hang on for way too long if they do.

And when they do let go, sometimes it can be bumpy, sometimes the succession is not great and everybody’s trying to avoid hurt feelings or being disrespectful, but the time can really come.

And what’s really going on there on a human sort of psychological level is that the person isn’t just retiring from a job, they’re retiring from their identity.

And that’s a very, very difficult ask. So I think, you know, whenever I’m able to help leaders be more than just the sum total of what they do at work, I feel like that’s a victory for me.

David Pisarek: Yeah. Work is so much a part of who we are because we seek fulfillment from the work. Whatever industry, whatever sector, whatever it is that you do, it’s part of you. Right?

So, like, how do you divide that? How do you pull that out? Do you find that some of the leadership is feeling lost before engaging with you in these type of conversations?

Jonathan Bennett: Well, let me tell you a story. I had a client, you know, in the last few years who was stepping into a role that had been held by a previously beloved, longstanding leader.

And, you know, what that person experienced over the course of their first year in the job. And this is a senior leader was, you know, just having to uncover rock after rock after rock of where things had just been done in a certain way, hadn’t really been challenged, and they were really just artifacts of this very, very, very long-standing beloved leader’s tenure. And it just becomes so insular and not healthy.

And so, you know, I guess I’m always supporting folks to become self aware and ask themselves, “Is this all about me, or am I still working in the best interest of the organization?” And I think if it’s not the latter, then we need to take action.

We need to help folks, whether we’re board members and leaders are hanging on too long, or whether it’s time for you to just, like, move out of this job and move into a new job at a new organization.

If that’s you, then to not wait. These things tend to not get better over time. They tend to harden and kind of get worse.

So, you know, if you’re feeling that now’s the time for you to make a move and you want to refocus yourself, it doesn’t mean you have to discard your identity. It means you need to incorporate these lessons that you’ve learned and take them somewhere and bring your gifts to the next role.

David Pisarek: And that’s it. Right? Like, all of our life experiences have led us to who we are right now, and it just builds up to part of us.

And your experience isn’t linked specifically to your job, right? It can be other things, like, let’s talk about, I guess, work-life balance. So non-profit executives are really bad at it.

Jonathan Bennett: They’re really, really bad at it. Yeah. Yeah.

David Pisarek: Guilty, too.

Jonathan Bennett: Like, because if you care deeply about the cause that you’re working within, the barrier between your life and the things that you care about deeply as a human and your work, that is a very thin, permeable barrier.

So, you know, I think what we are learning is that younger folks are better at boundary setting. It certainly has infiltrated the conversation broadly.

I mean, I don’t know if anybody has watched the latest Taylor Tomlinson Netflix special, but, you know, as a 30-year-old comic, she sounds totally different.

The way she talks about mental health and the things that she talks about, some of which are workplace and career-related and some of them are life-related. I think you’re like zeitgeist to me, because younger leaders that are coming through, they’re okay to talk about boundaries, and they’re okay to set boundaries and understand the concept of them.

But, you know, for folks that have been around longer, that was you know, pulling your weight, that was, you know, believing deeply or caring enough.

And so the rules are changing and have changed, and we see a mismatch between senior leadership and what their expectations of showing up and grinding versus what younger workers coming through, they know they can’t be at their best for, you know, 10 hours a day, and so they’re literally just not going to do that. And how that gets interpreted.

Younger folks are interpreting that “I’m working smart, I’m looking after myself, I’m staying healthy, I’m making sure I’m balanced.”

Older folks are like, “You don’t care enough.”

And, you know, it’s wrong-headed. But really it’s just that society is undergoing some change around this right now.

And I can spend an awful lot of time with fellow Gen X leaders helping them keep up with that change, helping them understand that they can’t lead in the way that they were led, that what got them here won’t get them there, because the folks that are on their teams aren’t responding in the same way.

They don’t care about the same things. Their principles and their values are the same, but how they want to organize themselves and their relationship to work is different than what they had when they were at that stage in their own careers.

And so they’re not the right proxy for what’s going on in the lives of their staff and their more junior managers.

David Pisarek: For example, I think Covid kind of really accelerated that with, like, the shutdowns, the closures, work from home, coming in.

I think that really showed a lot of businesses like “You can trust the team.” You hired them for a reason. They’re the experts in whatever. Let’s empower them. Let’s trust them to get the work done that we hired them to do. Do we need them in the office?

Jonathan Bennett: No.

David Pisarek: Is it okay if they sit on the couch for 20 minutes and kind of like, zone out and work on getting mental clarity so that they can come back in refreshed for, like, the meeting that they’ve got. I’m good with that.

But I think there’s maybe a generational gap in there where the legacy way of dealing things versus the current way and different personalities.

Some people need to be in an office, they can’t be at home because they’re too distracted. They have to do the laundry or take their dog for a walk or children or phone rings versus having, you know, they’re at the office. All those distractions are gone.

Jonathan Bennett: Yeah. It really needs to be customized for the person, for the individual workers, for the team that those workers are a part of, for the company and the sector that they’re involved in.

I feel quite neutral about all of this. I am sympathetic to all sides, and I’m not just being a wishy washy, middle of the road person. It’s because as somebody that works, you know, with organizations and companies right across North America in multiple different sectors, there really are many, many different answers, and they can be right and context-specific.

So, you know, what I usually kind of find myself saying is, like, “What’s the DNA of the organization and your sector?” Like, if the way you work is inherently in person and it’s collaborative and that’s not just some historic artifact, that is actually how the work needs to get done, then you have an in-person kind of business, and that can be okay.

And being upfront about that, like, it’s the bait and switch that kills people when they think they’re getting hired in a hybrid job. And actually, the culture says you really need to be seen and be there.

Well, like, that’s really not fair to especially new people, but for many, that isn’t true anymore, and that actually people can be just as effective.

And so folks are moving to using an office or using getting together in different ways. Like, it’s a team-building event. It’s a chance for us to do deep work once a month, once a quarter.

And I think that they’re all good solutions. I just think that we’re still in the churn. We’re further along than we were a year ago.

I think, you know, the more organizations that get out of the lease that wasn’t working anymore under the new circumstances, etc, etc. Like, I think that we’re just going to kind of burn through this part and we’ll reestablish ourselves.

And I just think that honesty is sort of the best policy with this, is that you have to know and you will attract workers and folks to your team that want what you want, and it’s okay what you want, but if the existing people don’t want it, that’s where the rub is.

And it’s just going to take a while for this to work itself through, I think.

David Pisarek: Let’s talk about digital strategies. What key obstacles do non-profit leaders face? How could a digital strategy help them?

Jonathan Bennett: I think the non-profit sector’s come a long way. Yeah, people did paper brochures when I started. So, so much has changed. I think most organizations struggle with their tech stacks, with getting stuff to just work properly.

If you’re just, you know, a one person shop and you’re the communicator, the marketer, the brander, you’re part time fundraising, you’re supporting the executive director, you’re running events like your hair’s on fire and it’s very difficult to be successful.

If you’re a little bigger and your organization’s got a bit more sophistication and a bit more bench strength, then I think we’re seeing the sector really perform in some pretty excellent ways.

They’ve understood that they can attract and retain all kinds of people, whether it’s new participants for programs, if you’re recruiting and you’re looking for new employees or volunteers.

I just think there’s so many smart things that are being like, evolved now because the tech is simple enough that non-technical people can start to use it.

Where it’s complicated and where I see people falling down, is it actually connecting to strategy? I think people get quite buried in tactics because the tools are really exciting to use and, you know, who doesn’t want to muck around on Canva for half a day, which is, you know, great, but on some level, how’s that driving our strategy?

What are we measuring? Where are the KPI’s that are coming out of this? To what purpose and for what end are we working? And I just think can get easy when you’re a doer, to not have people above you in the organization that are thinking strategically about how to make best use of your resources.

So the things you’re working on weren’t just somebody’s pet project, but they’re actually driving the strategy forward.

David Pisarek: Yeah, I think it’s important to have a clear strategy. “Here’s the goal for the quarter.” I think it’s really important to do quarterly strategic planning, but also have annual planning. “Here’s the goal for the end of the year.”

Break it down into smaller components. That way you know if you’re headed in the right direction or not. Yeah, it’s really easy to get lost in, I don’t know, ChatGPT prompts right? Like, it’s super easy to just get in, all of a sudden, where’d that last half hour go when there’s bigger priorities to work on?

My recommendation is calendar blocking. Find a spot in your calendar, maybe every Friday morning from ten to eleven. That’s your playtime to go and test out some new thing or other or to focus on something specific that might not be necessarily so aligned with the goal, but it’s something that, you know, deep down, is going to help the mission in the long run if you can only build an MVP version of it to get there.

Jonathan Bennett: Yeah, I like that a lot. I think calendar blocking is a great tool, and it’s great for all kinds of reasons because especially if you’re somebody that’s got a bit of a distracted mind, prescheduling when you’re going to work on things is a really effective, like, time management, personal time management tool.

David Pisarek: So do you have any advice for non-profit leaders on how they can enhance their online impact while making sure that they’re being mission-aligned?

Jonathan Bennett: Well, I mean, I am a fan of telling stories. I think that that’s the best way. I mean, I’m kind of, you know, recovering novelist stories really resonate and harvesting stories.

Actively talking to your folks about where the really pointed stories are in your organization and making sure that they’ve been shaped and crafted in a nice way that is going to emotionally resonate, that they’re going to include maybe a data point or two, that they have a purpose to them, that they’re not just some rambly quiet story, but that see some sort of transformational journey occur.

You know, organizations that are really good at fundraising typically are good storytellers, but there are many, many non-profits, especially in Canada, that are publicly funded. Therefore, their focus on the marketing side and the storytelling side is less mature.

And that’s because they’re not trying to win hearts and minds of everyday people to write a check for a $100. So if that’s you, it doesn’t mean that it’s not important.

I think that there’s many, many organizations that have amazing stories to tell and just haven’t developed the chops. And so I really think that that is a place that all non-profits can always spend good time on.

Because if people believe what you believe in, then they’ll commit with their time and their money. They’ll come and work for you, they’ll come and volunteer for you. They’ll support you in all the ways.

David Pisarek: If you’re not sure where to get started with talking about a story, take a look at where the money is going and what is the impact in your community or abroad on a certain ethnographic ethnicity or religious group or whatever it happens to be, what is the impact you’re having and tell that story right. That’s the easiest way to start.

Jonathan Bennett: If this framework helps folks, I’ll share it. I worked with a women’s shelter a while ago, and I realized that their whole brand positioning and their whole communication strategy was kind of focused on the front door.

So you can imagine the very difficult and emotional set of circumstances that face a woman that’s fleeing gender-based violence, and, you know, they’re sort of literally showing or getting referred to a shelter.

And so their marketing sort of described that. It was describing the despair. It was describing the pain, hurt, violence, trauma. And actually, what happened when I went in there and I listened to the stories was that it was a place where hope bloomed.

It was a place where from some of the worst moments in somebody’s life, people became safer. They were attached to programs and services, they did counseling, they were attached to housing, and they kind of exited the metaphorical backdoor of the shelter with hope. And so, you know, my proposition was, shift the spotlight from the front door to the back door.

Let’s tell a story of change, and let’s address the transformation that the women and their families that use the service inevitably would experience.

Because, in their own words, that was what they wanted to talk about. That’s what the client stories were about, and they were powerful.

And so I would just encourage anybody that’s not sure where to start to just ask yourself, where’s our front door? And where’s our back door? And where are we pointing the spotlight at? Is this a transformational story, or is it a story that is just how people got here?

Often non-profits love talking about process. They love talking about the things that they are funded to do.

Like, I used to do a gag where I would do branding workshops, and I would say, “Okay, so here’s what happens.” When I walk into a room full of non-profit leaders, I say, “Tell me about your organization.” And it’s a trick question, because what I hear is something that sounds like this. “Oh, okay. So we serve, you know, this catchment, and we’re funded through the ministry of Na Na Na, and we also have some united Way funding. Oh, and we also have a trillium grant, this year. We have a staff of 30, well, sometimes 35, if you count the students. And then we have this program, which is called the ABC program and the baby program.”

And by that point, I’m completely asleep. But the room is usually laughing at this point, because that is what it sounds like. People just sound like their grant applicants, and actually, they do amazing work. They change lives.

People engage with these organizations, and by the time they’ve left, they’ve got new skills, new pathways forward, access to things that they didn’t have beforehand.

And yet somehow we haven’t taught ourselves how to sound like that. So if that sounds like you, just ask yourself, what is the client’s journey? And try to describe that story.

David Pisarek: I love that. That’s so great. The short elevator pitch. What’s like the two sentence like, “This is what we do. Here’s how we help that.” I’m going to try that in a meeting one of these days.

Jonathan Bennett: Oh, you’ll hear it. Yeah, everybody does it. Yeah, everybody in the sector does it. It’s kind of just a knee-jerk thing, but it’s fun.

David Pisarek: Jonathan, these have been some really amazing and fantastic insights. So, Jonathan, if anybody wants to get in touch with you, what do they need to do?

Jonathan Bennett: Well, I’m very active on LinkedIn, and so find me on LinkedIn. I respond to direct messages. I also offer a 1-hour free session with me to do coaching or trusted advisory work.

If you’re a leader at an organization and you’re facing some tough stuff and you’d like to try out coaching, book a time with me and we’ll get to know each other and I’ll see if I can support you.

David Pisarek: Awesome. So go to clearlythen.com and you can get Jonathan there or LinkedIn profile.

Thanks again so much for joining in, Jonathan. It’s been great having you on the Non-profit Digital Success podcast.

To everybody listening. If you want anything that Jonathan has talked about, link to his LinkedIn profile or the website, just head over to nonprofitdigitalsuccess.com, click on this episode for all the details.

Until next time, keep on being successful!