Tish Squillaro 0:00

Hi, everyone. Welcome to Candor with Tish. I'm Tish Guilero. As you know, I have very successful and interesting conversations every time we podcast with a CEO and senior leader that want to share their stories. Today I have a dear friend and an executive that I've worked with many times who really is going to share some wonderful stories about how he both was on executive teams and grew his own executive team. I want to welcome Josh Resnick, a little bit about his background. He's an executive, a corporate attorney, and really known as a growth leader. He is widely recognized as someone who's who plays a lot of time within scaling global technology, AI, SaaS, media e-commerce, all of which I've worked alongside him, and he's been twice named to the Washington Stodion magazine prestigious tech titans list for two years in a row. A quick background he was leading the digital division of Gannett when I first met him, then became the chief operating officer and general counsel for Spree Commerce, and most recently the CEO of Fiscal Note, where they launched brand new flagship policy note platform and a streamline operation into the mid-2026. Welcome, Josh. It's exciting to have you both as a friend and an executive to share your stories today.

Josh Resnik 1:13

Thanks, Tish. Great to be here and always great to spend time with you.

Tish Squillaro 1:16

You know, one of the things I thought would be interesting because in our relationship alone, you have played the role of an executive on a leadership team. So you got to be peers with others, are being led by a leader and also build your own team. I thought maybe you could give a little bit about that, like the difference, the the aha from being on the team to actually building your own team.

Josh Resnik 1:38

Sure. So when I think about being on the team, so we're thinking back to my time at Kannet, where I went in to be a senior executive on the Gannette Digital Division, ended up running the division for a few years. And so spent some time in a traditional media culture, which was a bit of a culture shock to me, having come from uh digital media and AOL. And so I joined this executive team where the culture was really focused on individual success. So uh people focused on the success of their own division. Gannett was more of a holding company, and so the thematically the way it worked there was if your line of business was successful, you could get autonomy to run it, you wouldn't get too many questions, and so on and so forth. And so working with that executive team, you had a lot of very highly skilled people, but they were all oriented towards their individual success. And I was coming in from a digital perspective of being this totally going against that culture where digital was the first group to really cut across all the divisions. And so stepping in at Gannett, I really saw how it was a huge change. And so some examples would be one of the first initiatives I came there with was around revamping how we did online video across all the websites. And I remember presenting this plan and um people around the table, you know, kind of nodding their heads and you know, saying, Oh, yes, we should go do this. And I felt really good about the meeting. And afterwards, someone said to me, um, oh, yeah, when they said we should do this, they really meant, you know, each of them is now going to run and go do their own version of this. They didn't mean kind of the big we the way you did. And there was another time where I presented something to Gannett's CEO, you know, investment opportunity, and the CEO again loved it, was on board, but the meeting ended with CEO saying, okay, now go to the division heads and ask them if they're okay with it. So it was this real shift where I was on the team, but in this position of being kind of against the grain for what Gannett was really used to and having to kind of try to force this culture shift. And so the way I did that there was really focused on two things at the end of the day. One was communication. So I'm a big believer in communication as a way to break down barriers. And so that meant both in terms of, you know, my communication with others and helping make sure the other division heads understood what I was thinking about, you know, the initiatives we were thinking about, why, the success we expected, and so on, but also listening to them and hearing what they saw as the biggest problems to be solved, just to make sure that we were aligned in principle in terms of what we were trying to accomplish. And the other piece was leading with data. So everyone can have their own opinion about what to do. But when you lead with the data and you have the analytics to support the decision making, that's ultimately how you accomplish as much as possible, you know, on an executive team. And so we were the first group to really introduce analytics into those types of conversations. And it really made a difference in terms of what we were able to accomplish because it was a really, really good way to get people over the line in terms of getting aligned with what your objectives were. Those types of things are really important to understand because when you're on the team, you have to influence the direction more so than kind of controlling direction. You know, you don't control who's on that team. You're coming into a culture a lot of times. And so you have to leverage communication, leverage data to try to make that change. When it is your team and you're building out your team, so um, think about what I did as CEO at Fiscal Note, that's different because you have the opportunity to shape that team in the way that you want, but still you run into your own types of problems. And so at Fiscal Note is a very different type of culture in a very good way, a culture where people were genuinely wanted to be aligned, everyone was focused on the success of the company, wanted to row in the same direction. So that part wasn't our challenge. But what we sometimes had was this assumption or this appearance of alignment. And so as a CEO, it's something that you really need to watch out for because quite often you have people who will give you the appearance of alignment, even if they're not totally bought in on the things that you want to do. And it's you quite often kind of assume that people will be willing to share their point of view with you or speak up if they disagree. You might even think that you're encouraging that. But no matter what, quite often there's gonna be people or times where they don't feel comfortable doing that for whatever reason. Maybe they're not confident in their objection. Maybe they feel for whatever reason that you're giving the signal that you're not open to an objection, whatever it might be. And so that can be a real problem in its own way because you think you have alignment and really you don't at the end of the day. And so, you know, fiscal note, what I tried to do was I did really try to encourage people to speak up and voice their objection. Some of that was as I built out the leadership team, bringing in people who were more inclined to be vocal and to give them that space to be vocal and to object and to kind of demonstrate through action that that was okay. But also encouraging some others who I knew had good ideas, but might be maybe a little more junior and less inclined to kind of use their voice, but encouraging them to use their voice and saying, hey, you know, you made a really good point in that meeting the other day. I'd really love to see more of that from you going forward. So it's uh two different sides of the coin and different ways you deal with it, whether you're on the team or in charge of the team.

Tish Squillaro 6:52

And funny enough, we worked together in both of those situations. And watching you as that leader, there was one thing you had that was consistent is you listened and you pivoted to the audience. I remember at Gannette, they were very seasoned and set in their way. And so you had an influence by collaborating and allowing others to feel they still had a say. Whereas at Fiscal Note, they did have a say, but they had to get comfortable that it's okay to be wrong. And as a CEO for you, it wasn't hard to pivot. And for some people, I think they don't always remember that each person or each team is different. You can't just bring what you did with one company to the other. And you know, you're a perfect example when you ran the digital section, you were leading it. You just had to get the other people in char involved to want to align. And alignment doesn't always look the same. And so I do think that, you know, knowing that your biggest challenge will be getting people to actually commit and hold themselves accountable, which is what you were able to do because you had some patience. And so I do think that was the other piece is that you are patient where you give people enough room. And I've watched it where I even lost patience before you did in some situations, where you give enough room for someone to actually get there. And I do think those are two very real strong traits that make your role both on the team and managing the team easier to pivot. Was there ever a surprise that all the things you tried to do? You know, think of one of the roles where as the leader, you did all the right stuff. You know, you did all the right steps, you made everyone, you know, get all the information, the data, and still there was something that had you scratch your head and go, I just don't get it. Because I'm sure we've all been in that seat.

Josh Resnik 8:42

Sure. I mean, all the time. And in part because the most important job you have, you know, as CEO is, you know, it's all getting people aligned, getting people to act, getting them to hold themselves accountable. And working with people is hard, right? People are complicated and they each have their own motivations, they each have their way of working. And, you know, you mentioned patience, and I like to try to give people room to, you know, succeed or fail, you know, give them the room to get done what they need to get done. I like to give them the room to to voice their opinion, like we talked about. But then it's also always a struggle to think about when you're using the right amount of patience or sometimes too much, right? So, you know, do you sometimes wait too long before you make a change on the theme that should be made? Yeah, it's always hard and always a struggle to feel like are you walking that line in the right way? I think one thing that has been really helpful has been really taking to heart the feedback that I do get. Um, so that's really important to do and can be really hard. But when you have people who you trust on your leadership team and trust really in the right way, meaning like you really do value their opinion and you've created the space where you know that they can use candor with you. Those are really valuable relationships. And a lot of times you can get the best possible feedback there. And so using that feedback and taking that to heart is among the more powerful things you could do. And so, for example, at Fiscal Note, we had a chief administrative officer who was um especially really good about that and really good at kind of diagnosing some of the people, challenges that we had, very empathetic in terms of understanding where everyone in the room was coming from. And one of the best things we did was we had probably our most successful senior leadership off-site was one where he was particularly good at surfacing some of the thornier issues we had as an executive team ahead of time, making sure that those were on the table in a very open and honest way, and not shying away from pointing to some of the behaviors of me, right? Of the CEO, to say, you know, what do we think of these behaviors and do these work and do these not. And so doing that was really helpful. And what I tried to do going into that was to be very open about taking that to heart, right? And being kind of bringing the kind of an openness and humility to it to say, hey, I'm here just as much as anyone to say there are things that I could be doing better and I want to hear more about that. And we had some very good conversations because the table is set so well, and I think because everyone came in willing to embrace, you know, for each of us whatever we had to do to drive that change. So so it's really important to do that as well. And and especially from that leadership position to show that openness and that humility to change the behaviors that you might not realize yourself might be causing some issues.

Tish Squillaro 11:16

And being self-aware is always the first thing we've always talked about. You had two good points. One to share is what is your criteria on how long you give someone? Because a lot of times talent, which is unbeknownst to the person in the role, that they're not able because they're trying hard or they've been around a long time and they have the right energy, but the skill's not there, right? So there could be many elements where it had nothing to do with that person. What's your criteria timeline? Because I I'm positive, having worked with so many CEOs, that that is the the challenge that you all face is when do you make that change? Like what is that moment, but it's not too late? Because you kind of know when it's too late. It's like everyone's now screaming at the top of the mountain, but you want to be one step ahead of that. So what would you say is a good either milestone or or your game plan of you've got a feeling that maybe someone might not be the right fit, but you're willing to give them growth to learn. When do you know enough's enough to have to make that change?

Josh Resnik 12:18

It's a good question. I think it's one of the hardest things to manage as a CEO because when I think about where I've had to make those changes, and those, by the way, are the hardest. And what you described, Tish, is is probably the hardest of the part. Like, you know, anytime you need to let someone go, it's a hard thing, right? You are creating one of the worst days in their lives, right? So it's a very, it's a very hard, um, very hard thing. And it's worse when it's someone who is trying to do all the right things, right? They're in line with you, they're bought in on the plan, they're, you know, they're doing all those right things, they just can't get it done despite their best efforts. Those are the hardest. But what I've found over time has been, I don't think I've ever moved too early, right? It's always um, you know, if I'm ever guilty on one side, it's moving too late. And it's because I've, you know, tried to give that person the room to succeed, tried to really help them, try, you know, do all the things, try to help them there. But you're you're never gonna be too early on it. You're always gonna be too late. And you're always gonna get that reaction where you know, I've never had a situation where I've let someone go and people have wondered why, right? They are they've all seen it as well, people on the team. And so I would say go with your gut, because when I do look back on a lot of them, it's I really knew on day one. I just wanted to give them the room to do it. But what I would say is recognize what your gut is telling you. But what's most important is is act on that quickly, but it's not always just, you know, fire the person day one, but act on it in the sense of, you know, communicate with them. Here's the problem, be quick about figuring out if they can solve it or not. So you still give them that chance, but recognize that your gut is probably the right thing, that they're not at least in the right place for the moment. Move quickly to give them that opportunity to succeed or fail. And if they can't, then at least, you know, you've done what you can to try, you've communicated with them about it, and better, you know, better to move on it quickly than let it linger.

Tish Squillaro 14:06

Yeah. And I do think communicating with them, like you said, and I know in the past you have, to kind of say what is expected. Because a lot of times they're not even realizing if no one is comfortable giving the feedback, they go along their path, not realizing how much they're missing the mark, right? So one is let's set the stage of what's expected and let's show the shortfall where you are not meeting expectation and what can we do to help you get there. But then the one thing I didn't hear, and I guess maybe something to consider is put a timeline for yourself, a month, two months. Because, you know, days, weeks, months roll together, and you can easily say, let me one more quarter. And I do think that is every CEO's challenge. I wouldn't say it's just yours, is that you do see a little movement, but it's not enough for the whole business, which is when I'm assuming you go to one of your confidants, because I guess feedback they may give you is I think the time is ready, or let's at least look for alternatives. Perhaps there's another role for them. Because, you know, again, it's not always that people have to let be let go. I do think that's the biggest challenge, or maybe not challenge, that's the one assumption that I think CEOs struggle with. It's not a firing, maybe. Maybe it's a different role, or maybe it's a smaller role. So it's not as if you have to give them an out, but a different role. And I do think that might help the timing a little bit. So that would be the only thing I'd add to that.

Josh Resnik 15:27

Yeah, I would also just say one other thing is a lot of things what gets in the way is you sit there and you try to work through, well, what will it be without this person in the role, right? So meaning this person is running this department for me. I don't want that seat empty. And so you go through this wrestling match of, you know, hey, it's probably, you know, let me work with them, try to get them to succeed, right? You want to give them the chance. You also don't want to sit there with a role open for three months, six months, nine months, whatever it might be. So that is always part of the challenge to you. But I would say, you know, one, I think best practice there, and again, easier said than done because you you can only spend your time on so many things. But the more you're lifting your head up, you're connecting with people outside your company, you're networking, et cetera, so that you're kind of getting to know other executives who would you know potentially before then. That's a good thing. And the other is building in uh bench strength on the teams as well, so that in those times where you have to make that decision that you have people you can call on, those are good ways to deal with that issue too.

Tish Squillaro 16:26

Aaron Powell I was gonna add just that next is you it's not mean to kind of think of your plan B, even if you're giving someone a chance, because yeah, you're running a business and you have to be able to have that. And either you're networking looking for a replacement or the bench strength to pick it up, because you're right, you can't have it empty, you can't be vacant. That's not gonna scale the business or get the needs done. But it's not wrong, and I think there's a moral compass here that people get uncomfortable with thinking about a plan B while also helping with a plan. And I do think you have to do both. So I would say that's a great point to bring up for those who are, you know, dealing with that right now. Every team is gonna have to look at talent to see whether or not what you build today is what's gonna get you there for tomorrow. So that would be my next question to you. I mean, as you built out the leadership teams, could be at any one of the companies, but I would say maybe the last one, because I was there to see it, we made changes throughout the evolution of where we were going. Sometimes because the talent needed it, other times because the business changed. And so then we had a mirror what you needed. You know, how do you navigate through that? Because that always creates cultural friction on the existing team when morale could go down and it could hurt how everyone feels. What's your suggestion if you know you've got to make people changes, but you also want to keep the team motivated?

Josh Resnik 17:49

Yeah, it can be a hard thing because you don't want people always looking over their shoulder, wondering what other changes might be coming down the road, et cetera. And so you don't want to have to, you just don't want to create that kind of culture. So again, the best thing you can do, but again, easier said than done quite often, but the best thing you can do is be more decisive in your changes more quickly. And because again, if you are seeing this, right, if you're seeing, hey, the business is going this direction, we need to do XYZ, we need to change the team in this way. Number one, you're probably not always going to be the first person to see it, right? So other people are seeing that in the way that they're operating their piece of it and seeing that that change is needed. So you don't want to let it linger for that reason. But also better to do it sooner and better to kind of go deeper or make more of the changes that you need so that you don't have to constantly be be doing this every three months, every six months. Oh, you know, I made this change, but oops, you know, I should have made this other change. So the more you can do that to create that stability, the better. But again, that can be hard because it involves uh you know a lot of different pieces coming together and do it right. And sometimes you'll be right about it and sometimes not. But the other piece is the communication side of things again, and making sure that you're clear with your team on not just what you're doing, but why you're doing it, what the expectations are and so on, and to continue with that communication and to do that communication as a team, not just in one-on-one conversations. That's how you create and continue to drive that alignment. By doing it as a team, you sometimes that can be a slower process, like when you think about your communications of trying to get things done through working with the team. But it's better because it's a good way to ensure everyone's hearing the same message in the exact same way at the same time. It's a good way if you're able to foster that culture where people are comfortable voicing disagreement. It's a good way to get that disagreement into the room. And so it's a good way for the team to understand these strategic shifts, the personnel shifts in a shared, unified way, again, hopefully with constructive disagreement as part of it. So I'm not saying, you know, so it's not necessarily shared in the sense of um, you know, people are afraid to speak up, but it's people are all hearing that same disagreement. People are hearing, you know, you as a team work through it together. And that's how people can rally around it, get comfortable, and ultimately not just feel that they're bought in on what you're doing, but that they feel that they're a part of that as well. So that's an important piece too.

Tish Squillaro 20:10

Yeah. And I do think sometimes we don't realize we hold back information because we think it's not necessary. Or they don't need to know all the pieces because I don't want them to worry. But I do think humans, when there's uncertainty, it always goes to the negative that's something bad, right? So I do like your approach to let's send the message to them all at the same time and consistently say it. I do think it's important to say it more than once. I think then it becomes real. I mean, once being said, without actions to follow, and sometimes your actions can't follow your message right away. So the more that you create a roadmap where you can do both the words and the actions, I think the more people believe. And then believing builds trust. And I think trust is one of the most important things that a CEO is in charge of building with that team because it starts with them. And I'll leave you with one last question because I know we have to wrap up soon. But you mentioned having people around you that you trust to give you real feedback, which isn't easy to hear, right? Because we always think we're doing the right things with all of our heart and our soul, and we try to get the right thing done. What's one piece of feedback that surprised you that someone gave you that you still remember today as something that you'll never forget they said and you're always working on it because it's just not that easy to not be that way, if you have one?

Josh Resnik 21:27

So, yeah, it's interesting. So we at fiscal note, actually, when you know I was talking about that that SLT offsite that we had, one of the things that came up was when I'm interacting with someone and talking to them about, you know, project, initiative, whatever, I'm always asking a lot of questions because that's just how I learned. So I'm asking a lot, I want to understand better about what they're working on, why they're doing things a certain way. If they're getting results, I'm trying to understand how to interpret the results and do that through just asking questions. What I learned actually in that off-site, you know, with feedback I got was it sounded very accusatory, right? So a lot of people would sound like, oh, you're trying to get me or whatever it might be. And so what I realized was I'm really not going to be able to change that part of my nature in terms of that is just gonna be how I learn. But what I really tried to do was be a lot more conscious about how I kind of introduce that process. And so whether it was people, you know, on the executive leadership team or even more junior people in the organization where I'd be even more careful about it, I would quite often then start a conversation by saying, I'm going to be asking a lot of questions. I just want you to know that's just me trying to understand. That's not me actually, I'm not questioning you. It's just, I'm just trying to gather information. And so I don't want that to be misinterpreted. So that was, you know, in some ways a small thing, but really valuable because it was something where I was creating this problem without having any idea that I was doing it. So a really valuable piece of information I think has been really helpful.

Tish Squillaro 22:48

So tell them what you're going to tell them before you tell them is exactly what you say. Well, Josh, thank you. It was been it's been great to see you. And I enjoyed chatting about your journey. And hopefully everything we talked about today resonates with our listeners. And thank you so much, everyone. We'll see you the next time.

Josh Resnik 23:05

Thanks, Tish. Great to see you.