MLP 155: Leadership Lessons From An Experienced City Manager with Jeff Fielding

If you are looking for inspiration from a leader who has dedicated his 40+ year career to serving the public at the highest level, then you’re going to really enjoy episode #155 on the Meeting Leadership Podcast!

That’s because this episode features an insightful interview with Jeff Fielding, the Chief of Staff for the City of Toronto, and an experienced City Manager and Chief Administrative Officer.

In this episode you’ll learn:

  • Why is it critical for leaders to learn how to quickly reflect on mistakes and calm themselves down so that they don’t erode their confidence
  • Why leaders need to have compassion and empathy for others
  • Why leaders need to be authentic
  • Why leaders need to clear obstacles out of the way so that people can do their jobs well
  • Why values must be clearly communicated
  • How collective accountability creates a wonderful environment in which people can make mistakes, fix them quickly and know that their leaders have their back and more

Jeff Fielding

MLP 155: Leadership Lessons From An Experienced City Manager with Jeff Fielding

Jeff is the Chief of Staff in the City Manager’s office at the City of Toronto. He began his latest role in April 2019. Prior to joining the City of Toronto, Jeff was Calgary’s City Manager, where he led a staff of 15,000 employees, managed an annual civic budget of $4 billion and an annual capital program of $2 billion.

You can get in touch with Jeff at

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Gordon Sheppard: As a leader, if you’d like to learn more about these core values, individual responsibility, collective accountability, and how they can help you to build an outstanding team that can do their jobs at the absolute highest level. Then you are going to get a lot out of episode 155 on the Meeting Leadership Podcast, and that’s because we’re going to learn about these core values from Jeff Fielding the chief of staff for the city of Toronto.

Are you a professional who wants to become a more effective leader? Then get ready for practical tips from the coach with the experience and inspiration to help you succeed in any leadership situation. Your listening to the Meeting Leadership Podcast with Gordon Sheppard.

Welcome to another episode of the Meeting Leadership Podcast. My name is Gordon Sheppard, and as always I want to say thank you so much for spending some of your valuable time to come to this podcast to pick up another leadership tip, another tip that you can take out to your next meeting to make it more effective, because this podcast is dedicated to those two things. You can’t be a great leader without knowing how to run a great meeting and you can’t run a great meeting without knowing how to be a great leader. I really appreciate that you’re coming here to pick up the tips to learn how to do just that. And I also want to let you know that this episode of the Meeting Leadership Podcast is brought to you by the Meeting Leadership Academy. There you’re going to find some terrific online and live options for you and your team to learn how to run highly effective meetings. The half day workshop that’s offered through the live part, well, it’s been really well received and you get a 38 page workbook that you get to keep as a reminder for all the good things that you can take forward and put into action in your own workplace. And you can learn all about it by going to

And now I am really excited to introduce today’s show. It’s called Leadership Lessons From an Experienced City Manager, and that is with Jeff Fielding. Now, currently Jeff is the chief of staff in the city manager’s office at the city of Toronto, but he’s also been the city manager for the city of Calgary, and there he led 15,000 employees and he managed an annual civic budget of $4 billion and an annual capital program of over $2 billion. And that is just a partial list of someone who has spent four decades dedicated to public service. This is dyed in the wool, he really believes it, and he’s come at his leadership style with so many great tools, including great lessons from his dad that he’s carried all the way through, great lessons from his mentors that you’re going to learn about. And I think the biggest piece that you’re going to find out about is that a leader really has to live their values and he’s been doing that again, decade in decade out over a long period of time, and there’s a big smile in his voice, and I know you’re going to get a lot more out of the interview when you actually listen to it. So here it is, the wonderful interview with Jeff fielding. Jeff, welcome to the show.

Jeff Fielding: Well thanks Gordon and glad to be on a show.

Gordon Sheppard: Well, I really appreciate that you’ve taken the time here because it’s not often you get someone with this kind of resume to come into this position to give us some suggestions on maybe the leadership journey that you’ve been on, but I know that you’ve been in these roles as city manager, CAO, you’re now the chief of staff. These are chunky titles. They require quite a bit of leadership along the way. But for the people that don’t know you, how would you introduce yourself at a party?

Jeff Fielding: Well, I’m Jeff Fielding, I’ve been in the business of municipal government for over 40 years, 15 years or more as a city manager in the last little bit, certainly serving in the city of Toronto for the last year, chief of staff to the city manager. Enjoy municipal government. It’s been a great ride.

Gordon Sheppard: Well, and somewhere in there you didn’t kind of get beaten down in government. In fact, you’re a big proponent for this area and leadership has been a critical through line all the way through, and I was just wondering if we can imagine in terms of getting your best leadership suggestions, if you were speaking to one of those people that was you maybe a little while ago, who’s coming into their first role as a city manager, from a leadership perspective, if you were sitting with them, what would your main suggestions be?

Jeff Fielding: Well, first of all, you’ve got to appreciate and get satisfaction from serving others. It’s all about serving the community, helping council succeed, and bringing your management team to the highest level possible. In other words, be a great coach and be clear about the direction that you’re setting so that people know where you want to go and how are you going to get there in the future.

Gordon Sheppard: And I know that when we talked in the preinterview, one of your big inspirations is your dad and you’ve learned quite a few things from him. Can you help us understand what you’ve learned from your father?

Jeff Fielding: Well, I was really lucky. He was a great man and big part of my life. First of all, he said, do the right thing. So character was important. What’s in your heart, make sure you’re doing it well. So competency was also important to him from that perspective. The other thing was have compassion and empathy for others, so care about others. He was a member of a large family and certainly one of the older people that looked after his brothers and sisters. And the last one I think that stuck with me, I guess through all my entire life, is be true to yourself. Authenticity is absolutely critical in a leadership role, so you can’t be what you’re not and you got to build your team in terms of the blind spots that you may have as a leader.

Gordon Sheppard: Be true to yourself might be a little easier at the end of a career, but what would you say to this young person in terms of really being encouraging to, again, this potentially new city manager that… When I say new city manager, I mean this is someone who’s coming into any organization to be responsible at this high level. What are you saying to them about how to be true to yourself?

Jeff Fielding: Well, I think that that’s one of the things you do have to learn, but I have to say that you have to know yourself and you have to plant yourself firmly on the ground in terms of what you can do, what you can’t do, who you are, what you stand for, what your values are, and how you portray yourself in that role. And you have to be also very, very careful not to accept roles that you don’t suit. And so a lot of discipline is involved in selecting the jobs that you’re going to take on and selecting who you’re going to work for.

Gordon Sheppard: Have you ever been in a role that you didn’t suit?

Jeff Fielding: Yeah, I mean it’d be been through interview processes before where it wasn’t going to suit and I had to turn them down.

Gordon Sheppard: That was a very clear, true North understanding that you have underneath there, and I’m sure that this is something that has served you really, really well, but I’m taking you back to then at the beginning of your career, in terms of your first city manager job from a leadership perspective, were there moments when you kind of fell down and had to learn on the fly?

Jeff Fielding: Oh boy. I tell you I’ve had those circumstances lots of times. I can remember coming in within the first month and having to make a presentation to council and absolutely failing in front of a large staff and having to pick myself back up again, dust myself off and say, “You know what? Get back on the horse and be ready for the next day.”

Gordon Sheppard: And I can’t imagine how many people are presenting to council this week that are going through this same thing and I’m going to guess you win a few and you lose a few, but you said you were able to pick yourself up and dust yourself off. How did you do that at that time?

Jeff Fielding: It’s personal resilience. There is no doubt, waking up at 3:00 AM every day when you’re having a tough time, that was not unusual for me. So to be able to be self reflective about how you need to be able to settle, how you’ll be able to calm yourself in those circumstances and how you have to reflect on what you do well so it doesn’t erode your confidence. The resilience, personal resilience, is absolutely critical in a leadership role.

Gordon Sheppard: And in terms of getting through your career, have you ever had mentors?

Jeff Fielding: Yes. I was very lucky in my early career to have people that I could watch from a close distance. Those people were people that I, I guess, aspired to be like, that I could learn from and that had the ability of an open door that I could come in and chat with him about whatever it is what was on my mind or to ask them advice. And I still consult those same people today.

Gordon Sheppard: Isn’t that remarkable? So you’ve had some of these mentors in your life for a long time?

Jeff Fielding: Yes. And like I said, I have friendships that have lasted my entire working career.

Gordon Sheppard: And one of the things you said earlier, I’m going to go back to now about your dad was have heart. How do you teach heart to a new leader?

Jeff Fielding: Well I think that that you have to find yourself, and to your point, if it’s not inside, it’s not in your soul, it’s not in your heart, public service is not the career for you. You have to absolutely love helping others succeed and you have to enjoy the public life with the scrutiny and everything that comes with it. I’m very fortunate, I’ve made benefits and the entitlements that come with working public service are very generous to most people that are out there. So everything I have in life comes from that notion of public service.

Gordon Sheppard: There must be some proud moments for you along the way in your public service journey, because you’re saying you have to love serving. Where does that come from for you?

Jeff Fielding: You what’s really interesting, it’s the small things that happen almost on a daily basis that make up, I guess, those things that have compelled me to continue to be in public service, such as helping somebody who’s having a family celebration of a life, a husband has died, and the snow has built up on their street so nobody can get in to help them. We cleared that snow and they were able to go ahead and have that celebration of life. Picking a dog off the rail track so that the dog was safe. Little things like that add up day to day. That’s the one thing that happens in public service. It’s not necessarily all the big things that go on, but it’s the day to day things about how we help people.

Gordon Sheppard: Wow. I really can hear how leaders would benefit from knowing that, again, it’s not these big achievements or maybe those letters behind your name, but in fact it’s the little things along the way. When you drive into work and the snow is cleared, is that something that you smile about?

Jeff Fielding: It really is remarkable. It might sound corny to some people, but absolutely. When I see a city that looks the way you want it to be, the garbage has been picked up, the streets are clean, all those types of things that you hope that the city you’re leading will look like and that you’ve had some impact on, it makes me very proud.

Gordon Sheppard: Wow. And you can’t do this by yourself. Certainly in the current situation that you’re in, and it’s tens of thousands of people maybe that you might be kind of stewarding along the way, billions of dollars of taxpayer dollars and other dollars that you have to steward along the way, you have to be a team builder. What are some of the things that you’ve done to build teams around you? Again, we can hear that the streets get cleaned, but municipalities, they’re not always perfect when you arrive. So how do you build out these teams to help them empower themselves as leaders?

Jeff Fielding: Well, I mentioned earlier, it’s all about helping others succeed. The job is to ensure that you’re clearing out all of the things that are in people’s way that get in the way of doing a successful job. And there’s many of those things, whether it’s processes or systems that need to be improved, whether it’s making sure that people are in the right positions, whether it’s recruiting the right people so that we’ve got those supervisors and managers in place to lead the team. All those things are critical to building a great staff and then making sure that you’re communicating your value set and what’s important to you and your heart as a leader so that they hear from you time and time again and that you live up to those expectations. I mean leadership is about living up to what your value set is and making sure your behavior is consistent with the characteristics that you’re promoting.

Gordon Sheppard: And I’ll just pick up on that value set aspect for just a second, because one of my premises in my work is I believe that every meeting in an organization should be connected to the organization strategy. So I would hope that there is a value set in some way expressed within those strategic plans that can then be connected. Is there a connection in your experience, is it your own personal value set that you’re conveying in this case or are you actually able to embed that in the language of things like strategic plans and that kind of thing to then convey it to your staff?

Jeff Fielding: Absolutely. I think first and foremost, values aren’t co-created. When you get hired as a leader, it’s not going out and asking others what’s important to you. It’s what you can bring to the organization and what’s important to you as a leader. I used to meet regularly with all the new staff, once every three weeks, 40, 50 people that we would be bringing on into the organization and I would be speaking about the value set that was important to me, what we needed to do in terms of living up to those values, and the way in which we needed to be able to behave so that we’d be be supporting those types of public sector values. It was absolutely critical that I communicated that, be upfront, and be personal and available to those people that wanted to chat about that. And what was remarkable was that people really did want to know about that stuff more so than budgets and hard services. They really wanted to know about the value of the organization.

Gordon Sheppard: I’m so glad to hear a working example of conveying values. So often those values get written down and they have no meaning because they sit on a shelf or they sit up on a plaque. But here you are. I’m going to take us to that moment in time. I’m one of 40 or 50 people. I see you standing up in front of us. What’s an example of a value that you would convey and what would you say about that to get that across to me as one of 40 or 50 people?

Jeff Fielding: Well, there’s only two things that I promote. Individual responsibility and collective accountability. So when we’re talking about you do a good job, live up to what’s expected to you in that job, behave in the way in which we expect you to behave. But at the end of the day, collective accountability means we have your back and that we’ll ensure that as a team, as an organization, that we progress together.

Gordon Sheppard: We have your back. How do you deal with mistakes?

Jeff Fielding: Well, that’s one thing. Make mistakes and take some [inaudible 00:13:25]. I’m very much of a manager that promotes taking a chance, having a little bit of risk in your position, and you know what, you’re not going to live or die on those mistake.

Gordon Sheppard: This is so important in terms of leadership development, I’m going to ask, one other aspect of here is do you have sort of a… Maybe without naming specific names, but maybe an imaginary first name, a moment where you’ve helped another leader underneath you to get these values and help them to see them grow so that you actually saw a before and after with them?

Jeff Fielding: Well, I think right now we’re going through that with the city of Toronto and we’ve recently been involved in negotiations with our unions and it’s really important that we live behind the values of competence and trust and talking to our senior leaders about how important it is to convey that, especially during difficult times and difficult negotiations, when it’s very easy to get knocked off your footing and not behave or live up to those expectations around the values.

Gordon Sheppard: So much about personal responsibility and like you said, the discipline to carry these things forward. One of the other aspects that we’d like to get to in this podcast, and this is something you might have a bit of experience with, I’m just going to ask you, have you ever been to a few meetings throughout your career?

Jeff Fielding: Oh exactly. And I was known as the five minute manager. I’ve made it very clear in terms of dealing with the people that I work with, that meetings are there to decide and to provide direction, so if you think your job as a leader is to go to meetings, you’ve got the wrong outlook on what your importance is to the organization. You’re in the organization to make sure that you’re providing that adequate direction and that you’re deciding on the critical aspects that need to be decided upon. And if those meetings aren’t set up to do that, then you’re in the wrong place.

Gordon Sheppard: Wow. I’ve actually been a trainer in a room full of 40 provincial level employees and one of the questions I asked is I said, “Hey, have you ever been in a meeting and you didn’t know why you were there?” And stunning to me, I would say 95% of the hands went up and the poor looks on their faces when they actually had to say that out loud for a moment in time. So you sound like you can be efficient. How do you drive that level of five minute manager approach down through the organization to make sure that all the meetings are running well?

Jeff Fielding: Well, I think it starts right at the top to make sure that the agendas are clear when you do set those meetings, that the time of the meeting, that you stick to it, that you start on time. I’m a firm believer if the door’s open, door closes when the meeting’s supposed to start, so people get accustomed to your style very quickly. They don’t want to be outside door. The door has been closed and the meeting starting at 9:00 and they show up at 9:05, so it’s those types of things that are absolutely critical, putting that discipline into your organization and discipline around your meeting shows up in terms of your accountability to the organization.

Gordon Sheppard: I love the smile in your voice, when someone’s there… If someone’s there at 9:05 do they get let in?

Jeff Fielding: We let them in, but we make it a little bit obvious if they’re late.

Gordon Sheppard: You’re very diplomatic in terms of I’m sure some very dramatic moments that would occur and I’m sure it wouldn’t happen very often. It would only have to happen once if someone was late for one of your meetings. The last question we’d like to ask in these interviews is a very simple question, but very important. What inspires you?

Jeff Fielding: Well, it’s going to, again, sound corny, but actually helping other people succeed. I’ve been very fortunate in my life and I’ll tell you a quick story. I was driving on my bike going down Bow Crescent, which is a street in Calgary adjacent to the river, and this neighborhood had been devastated by the flood. And as I was going down that street, there was an elderly couple that were standing in front of an empty lot. And this is where their dreams had been shattered in a matter of hours. But as I progressed down that street there were great big red hearts thanking the employees of the city of Calgary for putting their lives back together. And that’s what I think inspires me.

Gordon Sheppard: That Calgary flood was devastating. The fact that again, on your way to work, you’ve got so much satisfaction for so many years in your career. I mean, this is just such a great opportunity to learn the leadership lessons from you. More than almost the things that you’re saying, I can hear that real confidence that you have when you’re going to work. Jeff, if people need to get in touch with you. Is that possible?

Jeff Fielding: Absolutely. My email address is They can write me anytime.

Gordon Sheppard: This is a great resource that people might have in the future. Jeff, thank you so much for being on the show.

Jeff Fielding: Thanks Gordon. Much appreciate it.

Gordon Sheppard: Now, wasn’t that just a masterclass in leadership? I mean, here’s someone who lives their values but also really ensures that they communicate them not only by how they live, but they actually bring people out and really find a way to actually talk to them because they know that people want to know what you stand for as a leader. And I also have to say that I really appreciate that nobody is late for Jeff Fielding’s meetings and that’s something that we could all use a little more of. And if you’ve enjoyed listening to this episode on the Meeting Leadership Podcast, I also recommend that you check out episode 46. It’s called Having a Title Doesn’t Mean You Know How to Run a Meeting, and in there you’ll get some great lessons that are going to really help you find out if you’ve got any blind spots when it comes to really overleveraging a title that you might have. And you can get that episode by going to a

And then, because Jeff mentioned that every good leader should know how to calm themselves down, especially after they make a mistake so they can pick themselves up and go again, you may want to consider checking out episode 61 on the Meeting Leadership Podcast because it’s called How Leaders Can Remain Calm During Heated Meetings. And that’s with Kathy Archer and you can listen to that episode by going to meeting And finally, because Jeff emphasized how important it is to be authentic as a leader, you might want to check out episode 18 on the Meeting Leadership Podcast. It’s called Why All Leaders Need to be Authentic, and that is with dean Joseph Doucet, who is the dean of business at the University of Alberta. And you can get that episode by going to

And I also want to remind you that this episode of the Meeting Leadership Podcast is brought to you by the Meeting Leadership Academy. If you are looking for solid online and live training options for you and your team so you can learn how to run outstanding meetings that move your strategy forward and ultimately help you build the organization and serve your customers and community at the highest possible level, then check out And for everyone who is already a subscriber, thank you so much for listening and if you haven’t done it yet, take a moment to hit the subscribe button on your favorite podcast app so you don’t miss another episode. And as always, thank you so much for listening and we’ll see you next time on the Meeting Leadership Podcast.

Are you a professional who wants to become a more effective leader? Then get ready for practical tips from the coach with the experience and inspiration to help you succeed in any leadership situation. You’re listening to the Meeting Leadership Podcast with Gordon Sheppard.

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Gordon Sheppard

Gord is on a mission to change the world, one meeting at a time. Over his 25+ years in business Gord has run or participated in more than 2000 meetings! Not only is Gord the CEO of Business Expert Solutions Inc. (owner/operator of Meeting Leadership Inc), but he is also a Facilitator, Trainer, Business Consultant, Author, Speaker and Podcaster who helps leaders learn how to have great meetings, so they can build outstanding organizations and serve their clients at the highest possible level.

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