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The ShiftShapers Podcast
EP 535 Coaching For Leaders, Clarity For Advisors - with Jenna Dillon
We explore what executive coaching really is, how it helps leaders make better decisions and show up with presence, and why advisors can use it to grow their practice and help clients cut costs and claims. We share signals that coaching is needed, how to introduce it without awkwardness, and how to build strong referral partnerships.
• Clear definition of executive coaching and who benefits
• Common leadership traps and the “business affair” pattern
• Executive presence as a practical skill set
• Turning vague goals into measurable outcomes
• How advisors spot coaching cues in client orgs
• Scripts for raising coaching without judgment
• Building trusted referral partnerships with coaches
• Why AI and hybrid work raise the stakes
This episode is sponsored by Benepower, the platform of choice for a modern benefits experience. Benepower is an AI-powered benefits platform offering access to top products and services, enabling consultants and employers to create customized plans, optimize usage, and measure effectiveness. www.benepower.com
What is executive coaching? And how could it add value for advisors and maybe even for their clients? We'll find out on this episode of Shift Shapers.
Announcer:This is the Shift Shapers Podcast, connecting benefits advisors with thought leaders and entrepreneurs who are shaping the shifts in the industry. And now, here's your host, David Saltzman.
David Saltzman:And to help us answer that question, we're joined by Jenna Dillon. Jenna is founder of the Executive Performance Institute for Coaching. And we're going to talk today about how insurance advisors can use executive coaching as a tool for business growth, both for themselves and maybe even for their clients. Hey Jenna, how are you today?
Jenna Dillon:Hello, I'm great. Thank you. How are you?
David Saltzman:I am awesome. Awesome. So let's let's dive right in. First, let's talk about defining the problem. And a lot of advisors, and uh, we've all heard the term executive coaching, but maybe we don't all fully understand it. So, how do you f define executive coaching and what should insurance advisors pay attention to in the first place?
Jenna Dillon:Yeah, I I would say executive coaching is, I'll first say it's not life coaching, uh, in that we're focused on professional pursuits that that individual we're coaching one-on-one wants to accomplish. And so with that being said, I tend to, in my executive coaching practice, focus strictly on top leaders, so chief officers and business owners, uh leading executives, and then there's also professionals who will be like their own boss and essentially the CEO of themselves, right? So those types of folks. Now, executive coaching is often when we're working one-on-one to help leaders build both their discretion, their thought process, and their discernment, their decision making and how they're acting upon their decisions from a psyche perspective. Um, while we are also building their executive presence, their technical skills and business acumen, all of these things we're looking to incorporate in our conversations so that they're developing skills to be ultimately successful and not just accomplishing what the desired outcomes are or goals are that they want to, but also so that they can navigate the challenging stakes that they have in front of them.
David Saltzman:So, what are the most common leadership or organizational challenges, whichever or both, you see in business today, especially those that insurance advisors might serve, and how do those challenges show up in real time and day-to-day activities?
Jenna Dillon:Yeah, you're looking for lead like leadership, what the leaders might be facing individually, or what the organization might be facing as a whole.
David Saltzman:I mean, both. Do executive coaches work on both of those realms?
Jenna Dillon:We do. We we absolutely do. And so I'll I'll first start with individuals. So um often they are there's a there's a number of different things. So uh often they're uh either running around like uh chicken with his head cut off is what they feel like, right? Like they are burdened because they feel like they have to keep working at this very fast pace, they're juggling a lot of balls in the air, and they feel that if they don't keep going at this rate, and even though they're exhausted, usually overwhelmed, um, if they don't keep going at that rate, then it will be at the detriment of their team's success or the organization's success as a whole. So it actually feels like a trap. Um, then there's other situations where their teams might be underperforming and they aren't knowing how they can possibly motivate them to keep their performance up or increase their performance. Um, there's also a lot of change happening in an organization, and especially big changes are when executive coaches can come into the fold. So think of when a company culture is going from a 4-1 hybrid model to a 3-2, or um, like four days out of the office and one day in the office, then at three days out of the office and two days in, right? That there can be a lot of resistance and uh backlash if the leaders aren't mindful of how to use some of their leadership skills and know some acumen around leadership to be able to prevent challenges from happening. Um, there's also like when mergers and acquisitions are happening, when there's an organizational restructure, a huge growth phase, a downsizing, any of these big changes, the leaders often don't know what they don't know on how it means their role will be evolving, but more so how they could evolve and develop for where the organization's going. And that's really where we come in. So we we tend to, or I tend to do a tailored customized development track to identify well, what ingredients about this organization and this situation or this situations and this person uh do we need to put into their development track and in what order and make sure that we can have this person digest it in the best way possible.
David Saltzman:Do leaders who don't know what they don't know cause damage sometimes?
Jenna Dillon:Absolutely. I mean, we're human, right? So every person doesn't know what they don't know, right? And so part of having a sound leadership team can help that. And when you have an executive coach being a neutral party that's third, that that's outside the organization, and they have certain, I'll just keep using the word, uh, business acumen, leadership acumen, even knowledge around executive presence that perhaps like leaders don't know very it's funny. Every leader I meet with executive presence, some of them just have it, and others, you know, they can see others that don't. But what do you ask most leaders to define executive presence, they can't, right? So that's what I mean, like executive presence from like a technical standpoint, but nevertheless, like they don't if they don't know what they don't know in areas that they can develop or even have knowledge in to apply, then they could unintentionally be causing a lot of friction or a lot of damage that can cost the organization a tremendous amount of not just challenges but money and time amongst their people.
David Saltzman:So if I'm an advisor and I'm running my own practice, what are some of the things? I mean, how does how does the need for executive coaching manifest itself? What signs should I be looking for where I go, you know what, I could use some help with this. Let me call up Jenna.
Jenna Dillon:Yeah, so I mentioned one earlier around how they they can feel like they're almost in this trap and they don't know how to get out of it, right? Like how they're overworked and have to feel like they keep hustling. Um, but if they slow down, it's at the detriment of everyone, but they're exhausted, you know, so it's a trap. Uh there's another version of a trap where uh they uh I've seen people do this and I find it fascinating uh just from a behavioral standpoint, where I I'll call it a little uh depending on their role. They if they're an entrepreneur, I'll call it a business affair. Uh but if they're exhausted or uh in that similar trap I mentioned, um, but the way that they cope is they go, oh, you know what, there's a lot of chaos happening with this team or with this organization or or with this project. So you know what? I'm just gonna I'm just gonna put it to the s, I'm just gonna put it to the side, hope it figures itself out, and I'm gonna go start a new project, or I'm gonna go start a new business, or I'm gonna go start a and I'll focus my time on that. And then I call it a little like affair, whether it's a project affair, a business affair, initiative affair, like whatever you want to call it. And then they just start focusing their time there because that's exciting and that's novel and that's new. And so they want to make sure that's successful because over here, this thing that they were working on, um, they don't know what to do about it. And so they're gonna procrastinate, right? So they might catch themselves in that situation. Um, another, and this is more surface, uh, I find, you know, what part of my job is to recognize how these leaders or these individuals that I'm working with are limiting themselves. And of course, most people don't want to be limiting themselves, right? So they don't realize that they are. And so on the surface, versus like I'm talking about really deep-rooted, you know, narratives before. Uh, if you catch yourself having persistent complaints or judgments or opinions that you notice are like on a broken record, um, look at that. You know, there's something that I say often when I'm training uh with teams or with uh leaders, that our opinions, our judgments, our assumptions can reveal our own self-limitations. They also reveal what we care about. Um, but to be able to recognize and just kind of reflect like, do you have any of those persistent judgments or complaints or you know, opinions or assumptions that keep coming that you're thinking or making it seem like reality or like a fact, right? Um it's it's it's a little a little surface level cue, if you will.
David Saltzman:You know, it's interesting. Most leaders that I've run into in my career are not that self-aware.
Jenna Dillon:Uh-huh.
David Saltzman:How how do you even get somebody to the point where that where I mean, is that kind of an aha moment for folks when you talk about that?
Jenna Dillon:Yeah. It it absolutely can be. And I would say a majority of them are. And part of that, I mean, I'll be real honest with you, David, and I'm sure you can relate to this because I feel like anybody at any point can relate to this state uh that I'll mention is when we get in a fast pace, whether we put ourselves in a fast pace or the environment calls for us to be at a fat fast pace, we are going so fast that it's like we're missing the side streets. So we're we're kind of creating unintentionally blind spots because we're going so fast. And so part of what I find is so fascinating and also a privilege for me to witness in a conversation with my clients is part of my job in the context of a conversation is to slow their brain down. And for them to be able to think through some things that sometimes they haven't thought about before. And so, yeah, like it can be very insightful for them. It can help them recognize things that they weren't recognizing, build that awareness that you mentioned. It can be from an emotional intelligence standpoint on how they are relating to things in their life that they didn't realize. It can be how they were treating themselves around their work ethic or their own performance or their teams. It can be a number of different things. And so, yeah, I mean, building that awareness is step one. Then knowing how to look at, well, the way that you're, the way that you are viewing this, is it helping you or is it inhibiting you? And then how can we move from there? Like how can we view this in a different way? Or what training or knowledge can we include that we didn't realize or that you didn't realize could be helpful or that you didn't have, right? Uh and then from there we go into okay, new application.
David Saltzman:One of the biggest misconceptions about coaching is um is that it's too expensive. Um, some people feel it's touchy-feely, um, and it's only for executives at Fortune 500 companies. How do you address those?
Jenna Dillon:Yeah, that's a great question, and I really appreciate it because it's something I I happen to be quite passionate about in my career, is helping inform my audience more about it and making it accessible. So um I feel like in this day and age, it's pretty fair, it's a pretty fair statement to say the term coaching is a trendy term. So there are more and more coaches coming out into the ether for people to know and have access to. When you're looking at an executive coach or a business coach, um, they likely, I mean, they they should have the training of how to look at tangible results, like with what the individual leader or organization is looking to have them accomplish. Uh, the executive coach should be able to know how to track and get clear on tracking measurable results in their progress. Um, that is a personal uh opinion or decision that I make uh before signing a dotted line with a client in an engagement. Is we get clear, well, what are the results that you want to accomplish from working with coach, from coaching and tangible, measurable results, not just like, you know, this is very uh valid for someone to say, I want to feel comfortable and confident speaking in front of a larger team and getting used to facilitating meetings. That's very valid, and there's not really measurable results there. So sometimes the individual or even organization needs to understand how do we translate that into results. So one, you can get a return on the investment, two, you can make a sound decision on now that we have that result clear, is this a sound investment? Like you can make that decision more clearly, right? So I would strongly suggest that people look at coaching as something to give you money and time and energy far back from what you're putting in it. If you aren't looking at it that way as a tool, you're going to innately leave value on the table in the engagement.
David Saltzman:You will like to work to our sponsor. If you're like most advisors, you've used platforms that promised to help, but only added work. Outdated legacy systems, weeks-long setups, endless data formatting headaches. Benepower changes all that. Built by Benefits Pros for Benefits Pros, it was designed for AI from day one, so everything works faster and smarter. They integrate vendors in days, not weeks, and take any data format, Excel, PDF, whatever, and make it usable instantly. BenaPower's Truvo app gives employees real-time AI-powered help by chat, email, or voice. And pre-authorization alerts prevent costly surprises. You get performance measurements and one-click reporting, so you spend less time on admins and more time growing your book. Move from frustration to freedom, from vendor to trusted advisor with Benepower. For more information, or to schedule a demo of Benepower Advantage, go to BenePower.com. And now, back to our conversation. Jenna, one of the things that you mentioned in our pre-interview was that you thought it might be valuable for advisors to mention the opportunity for executive coaching to the clients they're working with. I know, you know, I I I sold eyeball to eyeball, toenail to toenail for the first 20 years of my career. It it would have been an uncomfortable conversation because that's not something that I normally think about. How would an advisor include that in what they're talking to clients about? And how would they broach it so it doesn't feel weird?
Jenna Dillon:Yeah, I I appreciate your question. So often when I am building strategic referral partnerships with insurance brokers, uh, they, if they know what I do, then they can spot different things happening in an organization where it's a cue that they could use an executive coach. And I'll give an example. So one would be when there's a lot of claims happening and the employees are feeling a little disgruntled based off of how many claims are happening, uh, that can be a cue that the leadership can uh have some support to either build their leadership in a way where they are making sure the employees that are below them that they're overseen are feeling taken care of and cared for. Well, for for someone to approach, for an insurance broker to approach a top leader around something like that, um, they can pose it as rather than actually let me let me actually slow that down. I was gonna say rather than focusing on the things that they might be lacking in, focus on the the positive things that they could get. Um, and I was slow slowing this down because uh what most people may or may not really understand is our brains are wired with a negativity bias, because it our main purpose for our brain is to keep us alive. And so we're gonna be looking for perceived threats, we're gonna look for gaps and issues and problems naturally. Like it's how our brain wire so our brain isn't wired to keep us happy, folks. It's it's wired to keep us alive. Uh, and so because of that negativity bias, I think most referral partners, when they're first looking at what a coach offers, they'll go, Oh, I don't know how to approach a leader around getting if they would even want to be introduced to a coach because I don't want them to feel like I'm telling them they're doing something wrong or doing something bad or could do it better, right? Now, that's natural for someone to think that, but focus on what they could get out of it. You know, so you you mention facts. Hey, I noticed I'm noticing that you have these claims here, and um, I imagine you wouldn't want to have this many claims coming through. Is that right? So that's a fact. And then you're checking to make sure that, like, you know, your perception is like on par. Then you say, well, I actually know somebody who helps leaders learn how they can have those become less and less, how they can have less claims happen and have an organization flow seamlessly that actually ends up saving them money overall throughout the year. Because let's face it, one thing that insurance brokers are often getting as their objections in working with clients is the price point, is the expense. It's one of the biggest overhead expenses uh that a company will have. And so that's what they're facing as an objection on a regular basis is how can you make these premiums less? Well, guess what? If you're gonna help your clients, insurance brokers, help your clients have less expenses and overhead, that's an easy insert of going, hey, um, we can help your margins look better over time by having this resource, right? So there's a little bit of ways that some of the same objections insurance brokers could be facing, there's a solution to the objection by using these other advisors or executive coaches, uh, trusted advisors is the word I was looking for, as executive coaches to come into the fold.
David Saltzman:So, what what might a strong referral partnership between an insurance advisor and an executive coach look like? And how can advisors build the relationships again without feeling as though they're selling something extra?
Jenna Dillon:Right. Well, I think I'll first start off by saying uh what a trust, what I believe a trusted advisor is. And I think that's important to establish uh and get clear on from one professional to another when you are building a partnership is okay, what are we calling? What do we really want to accomplish in this partnership together? And how do we, what kind of value do we want to be and bring to our clients? And as a trusted advisor, what does that mean to you? Well, for me, it means I am going to be having a holistic approach of understanding what my clients are going through and experiencing so that I'm not focused just on my lane. If there's other things outside my lane that I can introduce them to and have access to, great. Because if I can bring more value by introducing them to these wonderful, very competent professionals, then I'm gonna build more loyalty, more trust with my clients. And they uh will see that and have seen that as a very unique value proposition that not all executive coaches have. Uh, and so same with uh these insurance brokers is with the more you can stand out as a trusted advisor in this way and bring solid introductions and show your clients how much you're really listening and thinking and helping to problem solve in areas that they might not even realize they are going to directly or even indirectly value you more. Um, so in terms of what an ideal referral partnership can look like, um, it can be around, like I understand for we can't just poof create a prospect, you know, out of thin air for to introduce somebody to. So then you can get creative. Well, what are other ways in the meantime that one, I can build my antennas? Two, what are unique questions I can ask my clients if I'm talking to an insurance insurance worker, what are unique questions I can ask my own clients to help me understand if if and when they could use you? What are the things for me to keep kind of staying afloat or monitoring, right? Um so you can build those antennas. Secondly, is while you're in the middle of building your own practice or your own book of business, what are your main goals? What are you focused on? Because perhaps outside of connecting you to a prospective client out of thin air, which I wish I could do, perhaps there's other ways that I can give you exposure to prospective clients and not just through an introduction to a prospect that's like, oops, strike will of iron's hot, right? So talk to me, like how how else are you getting clients? Or do you want to bounce off ideas of how to build your exposure and accessibility or even authority? Is there leverage that you could understand how to build business within the clients that you have? Uh, and can we talk about that, right? So there's a number of different directions that the leverage of an executive coach, like they know all the way that I'm thinking about this and the way the things that I'm mentioning of ways to leverage, they're great at this if they're good at their job. So you can leverage that in a conversation and building a referral partnership that can benefit you in more ways than just getting a prospective client introduction.
David Saltzman:So, last question. As the workplace evolves, you know, we've got hybrid work, AI, shifting employer expectations. How do you see executive coaches becoming even more relevant for advisors and perhaps for their clients in the next few years?
Jenna Dillon:Incredibly. I feel like every passing year, or I would even say season, my clients are feeling like the stakes are continuing to get higher. And I don't think that's going anywhere anytime soon because especially with AI coming into the play, there's more things to stay on top of AI, and AI is gonna keep evolving very quickly because it it has continued to do that, and that's that's not stopping, right? So, because on one hand, you can look at stakes being high, what is called for the leaders is not just how you can stay on top of it, but how can you stand out and build influence and leadership with it? And that answering that question gets more harder for any human who is also feeling like the stakes are higher. And so an executive coach helps dismantle, if you will, and recalibrate their thinking and ways to innovate and get creative to stand out, to use the fact that things are changing and how to leverage and find opportunity within it. And again, they're helping them think outside the box because they are that outside neutral party. And so it'll be all the more, I mean, dare I say necessary to have an executive coach as time continues, not just looked at as a, oh, this is a bonus or this is a nice perk to have temporarily.
David Saltzman:And that's a great place to end our conversation for today. Jenna Dillon, executive coach and founder of the Executive Performance Institute for Coaching. Jenna, thanks so much for your insight.
Jenna Dillon:Thank you so much for having me.
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