Ep 005  |  Chief of Staff: The Strategic Catalyst for Your Organization


Chief of Staff: The Strategic Catalyst for Your Organization

September 13, 2023

About this episode

It's no secret that effective collaboration, communication, and streamlined execution are essential for the success of any organizational strategy. However, achieving excellence in all three of these aspects can pose significant challenges.

To bridge the gap between leadership and the enabling teams, there has been a growing recognition of the critical role played by Chief of Staff. While this position was once primarily associated with the political and healthcare sectors, companies across various industries are now embracing it and reaping substantial rewards. In this conversation, we are joined by Jordan Gadd, Chief of Staff at Heluna Health, who shares his insights into the role and offers guidance on how to integrate it into your organization to drive meaningful progress and expansion.

Join us for a discussion covering the following key topics:

  • The pivotal role of the Chief of Staff in facilitating effective collaboration, communication, and execution
  • Strategies for infusing flexibility and adaptability into your leadership approach to enhance execution
  • Harnessing the power of authentic storytelling and efficient communication methods

Guest Intros

Strategy Gap Podcast Guest | Jordan Gadd with Heluna Health

Jordan Gadd

Chief of Staff, Heluna Health

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Transcript 📝

Jonathan Morgan [00:00:02]: 

Welcome, everybody to another episode of the strategy gap. I'm Jonathan. And I'm Joe. And today joining us all the way from beautiful LA is Jordan Gadd. Jordan is the Chief of Staff at Heluna Health and has an extensive experience covering different areas of strategy and strategic planning in both the health sector as well as education. So, Jordan, welcome to the show. Great. Thanks for having me. So, Jordan, one thing I wanted to start off with is where you work at Heluna Health. And I think a lot of people hearing that name may think, more traditionally about health care and hospitals and health systems. But the type of work that you do at Heluna Health is much, much more than that. So, do you mind giving a quick overview of the type of work that you do at Heluna Health and how you support the greater community there?

Jordan Gadd [00:00:46]: 

Great. Yes, thanks for that question. So Heluna Health is a public health nonprofit, and we're based in Los Angeles, and we've been around for about 50 years, we offer both direct public health services and programs. And we also support a range of partners and about 500 different public health projects each year, where we provide Fiscal Sponsorship Contracts and Grants Management Human Resource Services, so that a range of public health programs can really focus on serving their communities and executing their public health mission. We really think of ourselves as sort of the nonprofit public health infrastructure support, when we work in a range of areas from maternal and child health to the public health workforce, outbreak, community preparedness, disease prevention, early, early literacy. So, we really run the gamut in terms of focusing on the health of populations, whereas health care often focuses more on the health and wellness of individuals.

Joe Krause [00:01:48]: 

In your role as Chief of Staff, I think that it would be helpful to, to walk through that just at a general level than to have a direct question around the role within strategy execution. But generally speaking, a chief of staff and an organization like yours, what is the day to day look like as well as we'll get to the strategy execution piece, but touching upon what your role is in that as well, we'd be helpful for our audience.

Jordan Gadd [00:02:09]: 

Yep. So, I've been serving in chief of staff roles for about 10 years, and a variety of different organizations and settings, from education to now, public health. And while the role can vary depending on the organization and the team you're working with, I mean, ultimately, a chief of staff is there as an extender, a thought partner, and advisor to the chief executive to the leadership team. And working across the organization. Oftentimes, you find within organizations that work happens within departments within silos. And sometimes the CEO may be the only individual that's kind of really looking truly across the organization across those silos and making connections and facilitating change. And chiefs, chiefs of staff are really sort of that second position that can look across the organization, they may be the only other person that sees what the CEO is seeing. And so, they can be both a support to the CEO, and the entire organization and ensuring collaboration, communication, facilitation across areas, because we know that that's what we're sort of the real work happens. And so, I think we've also seen a great increase in the number of chiefs of staffs in a wide range of companies, you tend to think of Chief of Staff and the political role, you think of the West Wing and the sort of president's chief of staff. That's kind of the archetype. But you now find them in tech startups in public health, you find them in education, and you're finding them in a range of settings, because I think CEOs, management teams, organizations are really seeing the benefits the chief of staff bring to organizations in terms of executing on goals.

Joe Krause [00:03:55]: 

It's funny you say that because there I think there was an article pretty famously, in the last two years, like it was titled The rise of the Chief of Staff. And it spoke to what you just mentioned, which was very specific to certain sectors, but now becoming more and more popular, and I had the pleasure of actually visiting Illinois health and seeing Jordan in action. So, I have a different perspective on seeing this because I to Jordan's point, I have interacted over the last 10 years at achieve it with a handful of Chief of Staff but not in the same capacity. So, I work with Jordan very closely to get ready for the on-site visit we were going to do and review the strategic plan. And he was my main point of contact and also seeing him in action in the room. So, the point he made it was the C suite, the leadership team, and it was a very collaborative thing. And you can see that questions, a lot of questions around next steps and big picture and things like that were definitely directed towards Jordan because he was orchestrating the strategic planning process. And I must say, it was very nice to see you in action. And the day went very, very smoothly because you had a handle on it. I'm assuming that took time to get as good as that you've been doing it 10 years. So, if you wouldn't mind sharing with folks Like, how did you end up in a place where that that smoothness is there? And that trust is built? What have you learned along the way? What worked? What didn't work so that you are truly facilitating true strategic execution? How did you get there?

Jordan Gadd [00:05:13]: 

Yep. I mean, I tend to think of sort of a few key tenets of being a Chief of Staff. One is sort of doing, you've got to roll up your sleeves and do the work of being a facilitator being a sort of a facilitator across silos across areas, being a facilitator of change, and then connector, and sort of connecting make connecting dots, helping people see sort of how their work rolls up to the larger mission. And I think some things that I found, that are that have been helped, that helped me be successful. First is really knowing the mission and believing in the mission of the organization. I mean, I've been fortunate in my career to work for mission driven organizations, that's what kind of fuels me in my work, and knowing that the work I'm doing is helping sort of a greater good serving the community, making an impact in people's lives. So, starting with mission, I think is important, because I think often you will find that that is a key connector for all of the people that you're working with, from the CEO to the C suite to sort of all levels of the organization is that they're, they're in mission driven organizations, because they believe in that mission. So, you've got to start with that place and find a connection there. I think from there, it really is all about relationship building. And really sort of figuring out what are the needs the strengths from all of the team members? And how can I sort of augment support enhance what everyone sort of individually is doing and what everyone is collectively doing? I think the Chief of Staff is often sort of the utility player on the field, or sort of I like to say, people ask me what my job is that sort of that one line and everyone's job description at the end, it's other duties as assigned, that oftentimes is that is truly the chief of chat, the Chief of Staff job description. So, I think those are a couple of areas that I've found, have helped me be successful in this role. But I think also just being able to pivot and adjust knowing that each team you're working with is going to have different needs, and I have to kind of step in and meet those needs, maybe in different ways for different settings.

Jonathan Morgan [00:07:29]: 

Yeah, that's very much I love how you describe it, as you know, being able to be a doer, a facilitator, and a connector, we tend to talk about things in a similar vein about the different levels of planning and execution. And the way we talk about as you have the architects at the top that are, you know, building the plans, you have the doers at the bottom, but then you have that translator in the middle that's, you know, kind of working across those teams. But it seems like Chief of Staff at times, is each one of those components. Is it, you know, in your experience, either now or previously? does it tend to be pretty split between those three roles? Or is it more a facilitator, more connector, more ado, or at any point in time?

Jordan Gadd [00:08:09]: 

Yeah, I think that really, I think that's a great point and a great way to connect it over to sort of the strategy archetype. I think it really depends on the project or initiative that one is working on and sort of the needs of the project and the needs of the team, I certainly have found myself leaning into each one of those roles at different, often, even in different times of the day, depending on what I'm focusing on. Sort of I'll be in the doing mode for a couple of hours, and then shifting in facilitation for a couple of hours. So, I'd say overall, probably a pretty even breakdown, but really dependent on the project.

Joe Krause [00:08:47]: 

And you mentioned the idea of being mission driven. So, it was with a helping facilitate with a school district yesterday in Illinois, and typically mission driven organizations are the ones that are most resource constrained, constrained. Right. And so, the question I always get is, is it better that you think to be mission driven and have fewer resources and people that really care and will maybe move mountains, knowing that that could be a limiting factor at some point? Or have you seen other organizations that maybe are less mission driven, they are selling widgets to lack of a better term, but they have more resources in your experience? Who gets more done.

Jordan Gadd [00:09:22]: 

So, I think this is exactly where strategy and strategy execution comes into play. And this is why even being in a nonprofit setting in a mission driven organization strategy is so essential, because it allowed it's sort of the leverage point to increase our impact in as you say, a resource constrained environment. If you're not thinking longer term about where you can have the greatest impact, how you can use your resources, most effectively even limited resources, then you're not fully living up to your mission and sort of the greatest impact that You can be making. And so, I think that's why I told him the health we so highly value strategy and having good strategic planning processes, good fiscal year goal processes, good metrics, because ultimately, that's our sort of measure of accountability for our nonprofit mission and for the impact that we're making in communities every day.

Jonathan Morgan [00:10:21]: 

Well, yeah, and even I say that the flip side of that is even the goals, right, you're not, you're not doing all this to sell more widgets, or to increase profit at Heluna Health is literally saving lives and helping those in the community so that I, that gay strategy absolutely needs to be important.

Jonathan Morgan [00:10:41]: 

So, going, going back a little bit to kind of how you talked about the role of Chief of Staff, and you know, enabling strategy to ultimately achieve your mission. Talk about what you're doing now. But I'd love to kind of spend a little bit of time for people that maybe aren't in the stage that you are now and trying to think, how do we actually bridge that gap? So, what was one of the initial steps that you took as you came into this role, a previous chief of staff role we identified, you know, what, we have this not bad, but more historical planning structure that's top down. And it's not really connecting people across what were some of the initial steps you took across the teams to bridge that gap?

Jordan Gadd [00:11:21]: 

Sure. So, when I arrived here, we had a, a fiscal year planning process that was a little bit siloed. And the overall timeline of the process kind of seemed a little bit late in the game. And the goals were being set, once the fifth are sort of finalized once the fiscal year had started, and it wasn't aligned with our fiscal year budget process. So, I kind of have been taking stock in the first six months, identified some gaps, and then put in proposals in place to kind of move up the timeline. And offer opportunity in this first year offer opportunities to at least share out department goals sort of with the full team so that there was awareness of what everyone else's goals were, for the sake of awareness, information sharing, finding further opportunities for collaboration or for synergy, just to ensure alignment. And so, in that first year, we were able to kind of move up the timeline a little bit, and have a little bit more sharing of goals across the organization. But I knew that after that, there was still more work to be done. And so thankfully, leadership was open to further change and put in some, some processes to, to make it better that for the second year go around.

Joe Krause [00:12:50]: 

The idea of sharing of goals, so knowing what we're working towards, but considering that the type of work that you're doing with over 500 projects, impacting the community directly, how have you, if at all, Incorporated, the idea of sharing the outcomes of all the work you're doing is you're in a unique position where a lot of time and effort and resources are placed into a particular community program, and you might have changed lives literally change lives every day? How do you then maybe showcase those successes to make sure that people realize that the strategic plan is not just a piece of paper, it is leading to an outcome that looks like this, and that person's name is Amy. And here's how her life has been impacted by your hard work? How have you been able to leverage that to make your execution even better?

Jordan Gadd [00:13:30]: 

Yep. So, I can share sort of three different ways that we really think about sharing the successes of our strategic planning work and our work in general. So, the first, which is a little bit more internal facing is that we do regularly share out with our headquarters team and our board, sort of quarterly progress on our strategic plan, both in terms of the percent of tactics we're achieving, proud to say we've been at about 90% Plus annual achievement of tactics or tactics that are on track towards their sort of plan fiscal year, 25 year-end goals. And the below that we also share, like what, uh, what are the outcomes? What are the successes? What is sort of the content? What are the examples of the out sort of what's come out of the strategic plan, not just the numbers, because the while the numbers are great, sort of what actual changes what new programs have been implemented, what new initiatives have been implemented? How is it? What is the evidence that we're actually achieving sort of the strategic plan goals because we set those for a reason. So that's sort of the internal kind of measurement piece. Then we also to sort of introduce our internal sort of Staff to the programs sort of at our quarter at our monthly all staff meetings we have included we invite program leaders to come and share a bit about what their program is how it impacts the community it serves. So, this both is an education on sort of the program partners within hello to health, but it's also a public health education piece, because we're learning about HIV programs, we're learning about food and nutrition programs. So that's another kind of internal one, and then the external one. Through our advancement and strategic communications team, we publish an annual impact report that has Spotlight Stories of programs, initiatives that have deep community impact, and that are sort of tied to strategic plan, goals, and strategies. And so that's sort of our main external facing piece where we're really showing the great work that we're doing and the impact that we're making.

Joe Krause [00:15:50]: 

I think it's safe to say you've given four examples, the three internal one external, that all point to the idea of authentic storytelling, I mean, everybody out there today talks about the, you have to be authentic, you can't do some canned story, and not to bring into the politics. But there's a reason why State of the Union, whoever it is, theirs is full of stories, where they'll bring the folks in that there have been impacted by our program, and it does resonate, and depending on the story and the dry eye in the house, but we want to make sure that what we're seeing on paper actually translates into actual outcomes and making it a real story with a name. I bring it up a lot, but I haven't seen a ton of clients really lean into it as hard as you're mentioning. So, I think that's something for our learners, our listeners to really glean from this is that storytelling takes time to get good at. But it is so powerful. And hopefully, I mean, I don't know, I may be speaking at the turn, but I'm sure what the annual impact report and all that maybe it opens up other opportunities for funding and sources of help, because people are like, I'm inspired. I want to chip in is Have you seen that as well?

Jordan Gadd [00:16:52]: 

Yeah, I mean, absolutely. There's the sort of our desire to authentically communicate the impact we're making. But there's also as a mission driven organization, that desire to make greater impact through garnering additional resources for our programs and initiatives, building out new partnerships. We've been primarily California based, but with some national reach, historically. And so, there's this desire that we can bring the work that we've done successfully in California to other regions to other states, and so absolutely are sort of communication, our external facing communications are all about enhancing our reputation and awareness so that we can drive greater impact.

Jonathan Morgan [00:17:34]: 

That's awesome. I had almost the same exact thought as Joe is that certainly there are many organizations that don't do any of this. But all four of them are great examples. And you see more and more organizations, doing the kind of internal high level reporting, and then the external reporting, for those that aren't yet to that story level component of bringing in those program leaders and having them talk about the frontlines and what they're accomplishing. What does that process look like? Or how do you select who these people are? You? Is it during programs after programs? Talk us through what that looks like in real life? Yeah.

Jordan Gadd [00:18:06]: 

So, we've got a great Contracts and Grants team that really sort of serves as the lead with our programs, working with our colleagues in accounting and human resources, who kind of are the core client support for all of the programs that we partner with? And so these teams have such a great pulse on the work being done in each of these 7500 different projects. So honestly, this is where we partner with our colleagues to say, what's the great work that's going on, tell me about, like, which programs have sort of had great successes recently, which ones maybe haven't we showcased yet that we should be showcasing. So just asking those kinds of questions. Of those that are sort of on the frontlines working with our programs, has helped us figure out which stories to spotlight which programs to highlight, and which issues and putting the public health issues do we want to surface because they're timely? And we want to make sure that people are aware of sort of what's cutting edge and public health.

Jonathan Morgan [00:19:14]: 

And I imagined I imagined the program leaders enjoy it, or is it you know, kind of wrestling with them sometimes? No,

Jordan Gadd [00:19:20]: 

I mean, scheduling is a challenge for everyone. We're all busy, but no, I think we’ve seen great, great interest from the program leads and then the sort of the feedback and comments. I mean, you see them in the Zoom chats. Whenever we do this from our team, just thanking the program for the work that they're doing, saying they weren't. They didn't quite know, maybe at first, the full breadth and depth of the impact that was being made. And so you see that it's that it's two, it's sort of a two way street there and that the program leads are excited and interested to share this information and our team is really excited to receive it and to then sort of have that context and sort of further are understanding of sort of why we're doing what we're doing to support the great work that's going on in the community.

Joe Krause [00:20:08]: 

And shout out to grant writers write grants is one of the toughest jobs I did a little bit in college working for a politician. And I mean, it was tough, and stakes are high, no room for error. It's definitely a CVC. Have you ever run into a grant writer, give him a hug, because it's definitely tough gig. But they do their job effectively, it has a direct impact on a lot of great things. So it's when I make that quick point. But to switch gears, we're gonna ask the question a little bit not to ruin it at the end here, we're gonna say, you know, what could potentially what you've learned maybe in your current role, but I think the chief of staff role being so it's not, it's not it's new, and it's old at the same time. It's been around a while, but it is going through a whole revolution and Renaissance. If you're, somebody is listening to this right now. And they're like, You know what, that sounds like a great career choice. How would you what would you recommend somebody to like to, to get into it, and maybe what led you to the profession that to begin with, since you've been doing it for over a decade.

Jordan Gadd [00:20:58]: 

now. So, I'll start with what led me into it. And it was a little bit happenstance. But it's started with communication. So, I was sort of I was leading and starting up the communications function for a unit at a university. And through that, I was able to learn all about the programs that we offer, the impact and sort of that we were having in the community, our faculty there, their research. So, I learned a lot about what the organization does. And I built relationships across the organization just in doing that work. And so that kind of led to I was well positioned, because I had the knowledge, the relationships and sort of some of the strategic thinking, to kind of step into an initial chief of staff role. And then I think from there, it was about figuring it out, as you're going through it, how your positionality fits in, within the organization, what unique skills and experiences you do bring. And then as I talked about a little bit earlier, sort of that ability to adjust and pivot to kind of meet the needs of the team of the organization at that moment. And it's definitely been an evolution, I mean, even 10 years, and I still am learning new things every day. That's what excites me about the work that I do. Part of that the shift from education to public health was a big learning curve. But that was probably one of the most exciting things about the shift was that opportunity to learn about a new, a new field. So, if we want to talk about sort of characteristics or things to look for it that sort of that appetite for stood for? Yeah, I mean, for sort of great characteristics that I think would make a successful chief of staff would be a great appetite for information for knowledge about the organization about the field that it's in thinking about, sort of think of the traditional SWOT analysis, what are the strengths, weaknesses, opportunities and threats towards the organization, so that you're kind of thinking both of that big picture, mission driven lens, but also being able to drill down into detail. And that's sort of another successful trade is being able to pivot back and forth between attention to detail, but always keeping in mind that big picture vision of why you are doing this work, why an organization is doing that work. And then, in terms of tips, if someone was thinking about this, this as a career, I think, first and foremost would be to find a current or Chief of Staff for someone who's had that role and talk with them. I think there's nothing that can replicate that type of experience. And I think it's I mean, a tool like LinkedIn offers a great opportunity to find and connect with Chiefs of Staff in that in that way. And the other great, I will say there are a number of communities for chiefs of staff out there right now, including sort of some education programs. This, I can say, as someone who's been doing this work for 10 years, so these are newer to the field, these did not exist three, four or five years ago. So, it's great to see that I think that they're just now sort of this ecosystem of support for this career, where that just didn't exist previously, or at least didn't exist in the same way that it does today.

Jonathan Morgan [00:24:19]: 

Got it. Got a quick two part follow up to that. Talking about kind of how do you get into the chief of staff role? What's generally the path after that is if someone didn't want to go into CEO role is it lend itself to another position and then kind of continuing that? What do you see as the future of the chief of staff position as a whole?

Jordan Gadd [00:24:40]: 

Yeah, I mean, I think by for Chiefs of Staff and sort of future career directions in many ways are multiple having I mean, traditionally, yes, there's a CEO route, the chief operating officer or chief administrative officer route. Oftentimes they will li ended up sort of maybe leading a particular function, sort of maybe head of talent or head of revenue. But they've got the great lens of knowing the full organization or knowing even if they're shifting to a new organization, knowing that they need to know the full organization and not necessarily sort of their vertical, but that they that they're leading. And, sorry, the second part of the question,

Jonathan Morgan [00:25:27]: 

what do you see as the future of the chief of staff position as a whole? It's exploded in growth? How do you see that continuing to grow or evolving, or whatever the case may be? Yeah,

Jordan Gadd [00:25:36]: 

So, I think it will, I think the future of the chief of staff position will continue to grow, I think it will probably become a more normalized member of the C suite, I think another great area of growth is that it's, it's increasing not just at the chief executive level, but within sort of department leads. So, you may have Chief of Staff to the Chief Human Resources Officer or Chief of Staff to the dean of a college or school. So that it's you've seen Chiefs of Staff at multiple levels throughout the organization, and actually think that's a tremendous opportunity. Because oftentimes Chiefs of Staff find themselves, the only one in the organization, there's no one else like them. And that can be that time, sort of isolating or challenging. But if you've got within one company, a cadre of Chiefs of Staff, I think there's real opportunity for greater impact with within the organization because they all kind of understand their unique roles and can connect across that and serve the organization better. And I think the other sort of point about the future, the chief, the Chief of Staff is just sort of the further professionalization of the role, just in that there are more net network, networking groups, associations, formal trainings, benchmarking of salaries and job responsibilities and different levels and types of Chiefs of Staff depending on experience, and, and skills. And so, I think, just as we've seen other positions, kind of grow into a more formal and well known position, I think that will probably be true for the chief of staff as well.

Joe Krause [00:27:17]: 

Excellent. And, as mentioned, I got a I've had the pleasure of working with you and seeing how, how you interface with the organization. And when people come to achieve it, like new employees, let's say that we're hiring, they asked like, what are our most successful clients look like? And I typically don't, they have three things, they have a plan, which sounds pretty basic, but there's got to be some sort of plan, you'd be surprised. And that plan has to be pretty good. It has to have all the elements that we always talk about due dates and accountable parties but have to have that there has to be somebody who's championing the project, somebody that's kind of day to day that's taking on the reins of that, and there has to be some executive support, it has to be greater than zero. And what I've seen with Chief of Staff of folks that have that role, and clients of interface ensures the plan is going to be good, because typically, it's a project that you're shepherding. And then also, you're the person that's making sure you're coordinating with all senior leaders and everybody else. So, it's a great thing, especially with strategy execution is it ticks, basically two boxes off the bat, if a cheapest staff is doing their role and being in there. So, it was been really great to see that. It's not always as smooth, as I've seen with you and your organization, mainly because of the three things that are necessary to have a true owner in somebody like you, or anybody who has the chief of staff role. So, for our listeners, it really does add some horsepower to your execution efforts, especially if you've had struggled in the past. If you're really honest with yourself, you're missing one of those three, how do you get all three? It sounds like a good avenue would be the creation of a chief of staff, or potentially the expansion of some, some responsibilities to mirror that. But I just wanted to throw that out there as a real kind of connecting thing that I've seen in basically in your career coming together. And that was very, very helpful.

Jonathan Morgan [00:28:58]: 

Yeah, well, well, Jordan, we definitely appreciate all the insights and advice I learned a lot. I didn't know nearly this much about Jesus steps beforehand, and the role they played in strategy execution. So, I know, listeners will love it. And I hope that by listening to this, we have a few a couple of future chiefs of staff's coming out of this podcast. So, before we close out, just had one final question. And if you were to think about your journey as chief of staff, your journey and changing these organizational planning execution models. If you could think about everything you'd learn how to go back to your first role as a chief of staff for your first time leading this process, what would be the one piece of advice you'd give

Jordan Gadd [00:29:37]: 

yourself? Yeah. I think the most important part about the chief of staff role about strategic planning and strategy execution in general and the Chief of Staff's role in that in particular, really is relationship building. You can have the best plan on paper. You can have the tools to track it, you can have the resources. But if you don't have the relationships amongst the team and the team, the larger team, not just the executive team, but the larger team that's carrying out this work, you're not going to be as successful. And so, I think just ensuring that there are opportunities and if needed processes and systems just to ensure that relationships are built, that relationships are strong. I think that goes a long way to just really great strategy execution. Even it sort of builds on all of the pieces that that are needed.

Jonathan Morgan {00:30:39]: 

Love it. I mean, that's the perfect way to cap it and summarize your role and role of Chief of Staff. So Jordan, thank you so much for being on the show today. And look forward to connecting again soon.

Jordan Gadd [00:30:48]: 

Great. Thank you for having me. It's been Thanks, Jordan.

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