Agency Unfiltered - Mike Skeehan from Salted Stone

Evolving as a Leader Through Agency Maturation

Mike Skeehan, Managing Partner of Salted Stone, shares his experiences in evolving as a leader alongside the maturation of his agency and what it meant to grow, pivot, and reassign his responsibilities in moments of transition. We discuss important inflection points, the patterns he saw, and how he compares reactivity to proactiveness.

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Episode Transcript

To kick things off, we have Mike Skeehan, managing partner of Salted Stone. And he joins the show to discuss his experiences in evolving as a leader alongside the maturation of his agency. He recollects what it's meant to grow, pivot, and reassign his responsibilities in moments of transition, the important inflection points throughout Salted Stone's history, the patterns he saw, and how he thinks about reactivity to proactiveness today. Agency Unfiltered, filming remotely from the Dunn residence, starts right now.

KD: Hey, Mike, welcome to Agency Unfiltered. Thanks for dialing in today.

MS: Thank you for having me. I'm excited to finally be on the show. I've seen a lot of my role models within the agency ecosystem present, and I'm glad you're finally scraping the bottom of the barrel and getting to Salted Stone.

KD: Yeah, eventually, I was going to run out of folks and just had to decide on, yeah, maybe it's time for Salted Stone to come in. I'm just kidding. You're on the short list. Psyched to talk with you. I think the discussion at hand here, based on some of the pre-show notes and discussions we've had, I think it's going to be something on the mind for a number of different agencies and partners. I won't speak on your behalf, but I think what's worth getting your perspective on is evolving as a leader while your agency matures, grows, scales, and evolves as well. And so maybe the best place to start, when you say, evolve as a leader, what does that mean to you? And how do you know when it's time to evolve?

MS: Sure. I think, if I had to try and define it, it's when there is an invitation, through the circumstances or the events that you're encountering as a leader, when there's an invitation to take a material step forward, a step that's less of a difference in degree, versus what it was that you were doing yesterday, but maybe a difference in substance. And so I don't think those types of steps, by definition, I think, are less frequent, they're less common. They happen at key inflection points, at key stages of agency growth. So it's not something that I think agency leaders or organizational leaders, period, need to be thinking about day-in and day-out. I think the circumstances and the events converge into these key critical moments or themes or patterns that develop. And that's the time that the leader of the agency needs to be prepared to take a step forward perhaps into unknown territory, uncharted waters, and be ready to exercise leadership in a new way. Does that answer your question?

KD: It absolutely does. And let me ask you this as a quick follow-up. Obviously, there's no one-size-fits-all here. But how frequently do you think those-- you mention inflection points or milestones or convergence of actions. How frequently does that come up, at least based on your experience?

MS: I think for us, I think it's probably safe to say that we've hit one of those, I'd say, probably every four years on average, at least at Salted Stone. It may be different, depending on your business. If you're getting outside capital, if you have a mandate from investors to grow, to grow fast, grow heavy, grow rapidly, that may be a different experience. But for us, with our organic growth process, we got started in 2008, which I'd say was a key inflection point, the inaugural leadership milestone. And then from 2008 to 2012, we grew organically within a certain mode. And then in 2012, one of our first inflection points corresponded with becoming HubSpot partners. That really opened some new vistas for us that we previously didn't have our sights on. And that required then a transition from an agency perspective, a transition for me as the leader of the agency, from 2012 to 2016. My role as a leader was different in 2016 through a couple of key hires. I'd say that my role transitioned again, where more of the responsibilities that I had on my plate historically started to shift off of my plate onto some key members of the team. And then now, here in 2020, we're going through a similar transition, a similar inflection point. So for us, I think it's been roughly every four years. There are minor milestones along the way that require some adaptation, potentially. But for us, those seem to be the key cycle points.

KD: No, that's helpful context. You mentioned really quickly at one of the points-- maybe it was 201y-- but you had to transition some responsibilities off your plate. That actually tees up my next question, which is, when the point is there, when we meet that milestone, that inflection point, what does evolution look like? Is it a transition or reimagining of responsibilities as an agency leader?

MS: Yeah. I will probably answer this question in a more slightly long-winded sort of way. But what I try to do-- and your mileage may vary, right? Everyone's perspective is slightly different. But I intellectually have accepted or acknowledge what I'll call the spirituality of events. And without reading more into that than is necessary, all that I intend to communicate through that phrase is that there's a message behind the particulars of the day-in and day-out. And so when I think about it from that standpoint, the simplest way if I can run the risk of speaking in a secular environment, using terms that don't typically-- are typically employed in a secular environment, I believe that God communicates to people through the events of their life. And then we communicate back through our choices in response to those events. So that is ultimately how I think God and humans, practically-speaking, enter into dialogue. God provides the events and the circumstances. We choose how we respond to those events and circumstances. And ultimately, that interplay is where the dialogue occurs, where the interaction between human beings and God occurs. And that's a relatively simple concept and one that I don't necessarily-- I don't think everyone's going to buy into it. But that's sort of my mindset.

When I think about the function of a transition and what that tends to look like and how that tends to play out, generally speaking, there are events that occur that are bigger than something that I can control. I've been taking steps perhaps towards a direction, but then there are macro external events that loom larger than any of the micro decisions that I'm making on a day-in and day-out basis. And those macro events are demanding some sort of response. And so what I like about that general philosophy is the macro events are incontrovertible. They're irrespective of whether you believe that there's-- and it's the spirituality of the event. The events occur. They're incontrovertible. They're reliable in terms of-- or relative to, I think, our thoughts and feelings or interior chewing over the events that occur. They're eminently unreliable. They're the things that we're closest to, so they're the things that, generally speaking, we have the highest degree of confidence in, or we experience them most acutely, the interior phenomena that we deal with day-in and day-out. But they're eminently unreliable. One day, we think one thing. One day, we think the next thing. Our opinions, in many cases, are changing. And it's very rare that our opinions codify through sufficient data to become knowledge or belief, I guess belief in that knowledge.

But the events, they occur, and they're immovable objects. They, generally speaking, force you to respond in one way or the other. And so I think, in most cases, for most people-- certainly, for people who have my particular set of weaknesses, which tend to fall on the side of reactivity, versus proactivity-- the events that one faces are the primary catalysts for the transition, so if that answers the question in a very, very long-winded sort of way.

KD: No, it does. I'll tell you this. This show doesn't get into spirituality much. And so you've carved your distinct perspective on that in a way that many guests don't. So I appreciate the insight there. You mentioned reactive or reactivity. And I would imagine that-- I don't know. I wouldn't say symptom, but it's probably a major function of being an agency leader or an agency owner. Do you see your evolution as a leader moving away from reactiveness? Is that the ultimate goal, to start creating space to be more proactive? Is that the ultimate goal here?

MS: Yeah. Well, irrespective, I guess, of—so it's happening. What I will say is that it certainly wasn't my goal or my intention. But the most recent, let's say, phase transition or cycle transition, the one that's occurring right now in 2020, is requiring it. And so by virtue of that, it is the current goal, right? So in the current cycle or the current phase, that is what's happening. I think, historically, when I sign on in the morning, my calendar's, it's booked. My day is planned out for me by whatever the events that have populated my calendar, the week, the days, leading up to right now. And so historically, there's never been the question of, what am I going to work on today? Or what am I going to focus on today? Because that's been dictated for me by the demands of the job, whatever there's this fire--

KD: Here are the fires. Now it's time to put them out.

MS: Exactly. Yeah. And so we've gotten to a place organizationally where the putting out of fires, it doesn't fall onto my plate anymore. So now for the first time in the 12-year history of Salted Stone, when I log on on the morning, generally speaking, I might have one or two hours of my day that are preplanned as far as, here's things that you have to get done today. Here are meetings that are on your calendar. But the rest of the time, it's really open-ended. It's blue sky. It's green field. It's all of these things that most agency owners are dreaming of when they're in the trenches, when they're in the weeds, and they're on the front lines. Very few agency owners that I've spoken with get to the stage that they're all dreaming about, when they're going from fire to fire to fire to fire to fire, which is, I'd much rather be working on the agency than in the agency. But when you get there, it's like, be careful what you wish for. Because when you get there, now you have, if you have my particular set of weaknesses-- and not everybody does-- but when you get to that place, now it's like, OK, your day is no longer planned out for you. What are you going to do to grow your agency? What are you going to do to take the next step forward as a leader? And that, candidly, for me has been far more challenging than any fire that I ever had to put out. Because now, rather than just responding to stimuli, you have to actually come up with ideas. And I'll keep saying this, but if you have my particular set of weaknesses, you may run short on ideas from time to time, and certainly, good ones, anyhow. And so that has been an interesting transition for me to have to go through, is building those muscles that historically, I've never had to use.

KD: I would imagine putting out fires and the reactive approach, you got comfortable and confident in doing that, because those were the muscles that had to be exercised. And so you had strengths there. I would say this-- regardless of strengths and perceived weaknesses, I would imagine that this idea of evolving as a leader is going to exacerbate the deficiencies or weaknesses, regardless of where they fall. So for you and what your perceived weaknesses are, or the muscles that don't get flexed often, how do you brush up on those skills or habits? How do you skill up? How do you improve? So how do you bake that into your own operating system?

MS: Yeah. I'm 40 now. But when I was, I think, 32 or somewhere in that neighborhood, and my oldest, who's now eight, was a couple of years old, I remember I was, generally speaking, I've never been somebody who goes to the gym. I've never really been, since high school, very athletic. And I was throwing her around and just noticed I was getting tired. It was not easy. And that to me was a problem. I am too young to be getting winded or tired or have any sort of difficulty messing around with my kids. I don't want to be-- that's not the vision for my future that I have as a dad, as a parent. I want to be able to have fun with my kids. And so that was a catalyst for me to go to the gym for the first time and just start exercising. And I remember I got a trainer and the whole nine yards. And so the first month or so of going to the gym and meet with this trainer, he had to go, really? I look back on the amount of weight that I was able to, say, lift at 32 years old. And from the standpoint now of someone who's been going to the gym at least a couple of days a week for the past eight or nine years-- I'm not a gym rat, but I try and stay consistent. It's like stacking sandbags against the tide, just holding back the inevitable.

Now, I look back on the amount of weight that I was able to lift then. And I'm embarrassed for myself. I'm embarrassed for my 32-year-old self at being that weak. Because I got on the bench press, and I could lift the bar. So my first reps were with the bar, 65 pounds, or whatever the case might be. And over the course of time, I was working out muscles that had never been worked out before. They got stronger just by virtue of using them. And then they throw a plate on each side and throw two plates on each side. And now I look, and I'm like, I'm not the strongest person out there, but I can lift decent weight. And so I use that analogously to the process of exercising muscles, from a leadership standpoint, that haven't been exercised before. And I think ultimately-- I don't know if you've ever read, if you have a background at all in, any sort of philosophy. But that's where I got my undergraduate in and just reading Aristotle, really classic philosophy, which is where I tend to fall, more on the metaphysics than the epistemology.

But if you read Aristotle, it's a similar methodology for how he describes the process of cultivating either-- or becoming either a virtuous or a vicious person, cultivating virtue or cultivating vice. At the end of the day, each of these types of dispositions, it's a habitual disposition, but the only way that you arrive to the habitual disposition on either end of that spectrum between viciousness and virtuousness is by practicing the acts that correspond with either virtue or vice. So in other words, you become virtuous by practicing virtue. You become vicious by practicing vice. And I think ultimately, you become a more proactive leader by forcing yourself to operate proactively. And eventually, the muscles that you don't have build up. And I think that can be applied to any example. And I also think of particular, worth highlighting, is I truly do believe-- and this corresponds back to the general-- my philosophy or perspective around the spirituality of events. I truly do believe that you are really only responsible in that dialogue. The events happen, and now you are going to enter into a dialogue through your choices in response to that event. You are truly only responsible for your choice, the will.

So the human faculty of will-- humans, what separates us from every other creature-- we have an intellect, and we have a will. We have an intellect that's capable of conceptual thought. We have a will that's capable of choosing a good, a perceived good, based on what our intellect identifies. And so when I think about, where is the locus of freedom for the human? The locus of freedom for the human exists in the will. It exists In your choice. So you choose, and then actions may flow from that initial choice. And your actions may lead to success or failure. And in the case of having to build up muscles that didn't previously exist, in most cases, at the beginning anyways, your choice is going to lead to actions that fail. That's just the way that it is.

So I guess really what I'm trying to communicate there is choose, act, and don't become discouraged when you fail. Simply pick yourself back up, choose again, and that sequential process of small, little baby steps eventually leads to a paradigm shift. And then, all of a sudden, you are stronger in ways where you were previously weak.

KD: So it sounds like baby steps is key here and being OK with starting with just the bar. You've got to get the form down before you can add more weight.

MS: Unless you're just naturally a stronger person. I look at myself more as like a snail. There's snails in life, and there are these thoroughbred horses. Everybody is a little bit different. If you're a thoroughbred, you may be able to sprint far distances fast. If you're a snail, there's no point in even trying. You are destined to fail. If your standard, if your expectations for yourself, is that you will keep up with a racehorse, you will simply fail. If a snail tried to race a horse, that snail would get stepped on. It would get squished. It would die. So if you're a snail like me, then you take small steps. And you don't expect to get to the finish line any time soon. Or another analogy that I like to use or metaphor that I like to use, in that regard, is in most cases, in most circumstances in my life, I feel like I'm almost like a lazy, overweight pigeon that has one functional wing. And I'm like, well, I have one wing that's broken. I have one wing, and I'm constantly flapping, constantly flapping. And all I'm really doing is moving in circles all the time, because I'm flapping this one broken wing, and I'm lazy, and slightly overweight. And then every now and again, this gust of wind will come up from behind me. And if I just flap my one wing as hard as I can, somehow the wind will carry me 20 to 30 yards downwind. And that is how I get to the finish line. I can't rely on my own strength to get there like some folks can. Some folks who are stronger can rely on their own strength to get to the finish line. For someone like me, you have to rely on the wind to carry you there.

KD: And you know, I think that opens up a larger conversation into spirit animals. But it's good to know you're the one-winged pigeon.

MS: I'm the one person in the world who has a fat, lazy pigeon with a broken wing as their spirit animal.

KD: Mike, the next question I have for you, just to pivot over to org charts, I can imagine that evolving as a leader has a direct or indirect-- well, probably more direct-- impact to the way in which you source candidates, you hire candidates, you prioritize the needs for new candidates and new bodies in the agency. So how do you handle the hiring process for Salted Stone as a means for evolving as a leader?

MS: Yeah. I have a fun anecdote just around that. Or whether it's fun or not, it's at least an anecdote that is based in my own experience at Salted Stone. But I remember, it was probably back around 2016, it sort of dawned on me one day. Because between 2012 and 2016, we had the tailwinds of becoming a HubSpot partner. In 2012, I was still very much the one doing a lot of the work and managing a lot of the clients. So at least for certain types of work, I was the one. I had the most experience doing paid search, organic search. And so that was my domain. And then I was also the only one who cared enough about being like decently tempered on client calls that I trusted putting on the phone with a client. So I was doing a lot of the client interfacing and still some of the work. And so the process from 2012 to 2016 involved hiring production team members to take over some of those very production-oriented skill sets. And around 2016, I took a step back or had the realization, like a little, minor epiphany, that in every single situation where we brought someone on board to take over something that historically, I had been responsible for, the organization was now doing those things better than they had ever been doing them when I was responsible for doing them. And whether that's more an indictment of my own ability to do things well or the fact that I had to do many things and therefore, couldn't do any of them well, I think is less important than the realization that that was a fact. The fact was the organization was better every time we replaced me with somebody else.

And so then, in that moment, I just basically made a list of all of the things that I was still responsible for. So I took my responsibilities one by one, made a list. And then I organized that list in terms of what order, from my perspective, the order within which I thought that we would wind up hiring people to take over the responsibilities that had been identified on that list. And the last responsibility, the last one that I thought that I would wind up giving up, was sales. I thought that I was relatively decent at it. And probably I thought of also, it would be the hardest one to find someone who could do it.

And maybe that says more about, again, my weaknesses or my perspectives. But Salted Stone has ever really been very good at marketing or sales itself. And they probably inherited that from me as the leader. I tend to be more operationally-minded than I am sales and marketing-minded. But anyhow, the long and the short of it was I expected sales to be the last thing that would be relinquished from the list. And then, interesting, within a week after having compiled that list-- and so there's all sorts of stuff on there. There's director of client services. There's operations. There's sales. There's mark-- there's, I mean, finance. You name it, all the stuff that I'm typically still responsible for or was, at that point, still responsible for. But sales was at the bottom. But within a week of compiling that list, someone pinged me on LinkedIn a well-known name in the HubSpot ecosystem, for those of us who have been around for a while, pinged me, and basically said that-- and he was, at the time, on the team of HubSpot's top partner agency, the top partner agency back in the 2012 period. And he was leaving that agency for whatever reason. And so he reached out to me. And his role at that agency was business development. He was their primary sales guy, at least as per him. So immediately, I just looked at this list that I had just finished compiling, where I had assumed sales was going to be the last thing to go. But again, the events communicated something differently or at least communicated that I had to consider something differently.

So all of a sudden, right after having compiled that list, here comes a candidate that on paper, is potentially-- I can't imagine a more attractive candidate for us at that stage on paper. Because here's HubSpot's top agency at the time, the business development director at that top agency at the time, who was saying, do you want my services? From an org chart standpoint, that really was, I think, from 2016 onwards, up until very, very recently, that was candidly, the process for hiring-- what I would call higher up in the organization, was finding ways to replace myself. And obviously, as we scale, we may need more folks on the creative team or more folks on the dev team or more folks on the solutions architecture team. But those weren't really my skill sets anyway. We have models and budgets for hiring those positions. But for hiring the managerial-level positions, the senior-level positions. It was really a function of assessing my existing responsibilities and then hiring them. And now what's interesting is it's transitioned. Because once I basically, effectively, replaced myself and all of my day-to-day responsibilities through that methodology, now it's a similar function. But it's really not focused on me anymore. It's focused on those folks who I brought in to replace me.

So now the folks who came in to run biz dev or run sales, now it's like, how do we take things off of their plate? So it's identifying their responsibilities and then hiring down from there. And so the it's a similar methodology that applies, but it no longer applies to me. Now it applies to folks on the team.

KD: I don't know, Mike, if we've officially confirmed there. But in regards to the biz dev candidate, a high performer that was initially on the bottom of your priority list, you flipped your list and made it something to consider at the top. Did you end up making the hire?

MS: Oh, yeah. It was a process of deliberate— I mean, it was a more expensive hire than any other hire we had made up until that point in time. So I didn't know what to do. But what I knew is I did not want to hear an Eric Pratt, I love you dearly. I did not want to hear that Eric Pratt hired this guy, because I passed him up. Revenue River jumped on him, and all of a sudden, Revenue River has blasted off and has become the top HubSpot partner. I didn't want to hear in Lieberman, I love you, too. I didn't want to hear the Square 2 hired him. And then boom, Square 2 all of a sudden rockets off into the ether. So on the one hand, I had this fear, like, I don't want to miss out, and I believe that there's something here. And on the other hand, it's was just the logistical reality of like, I don't know if this is the right move. So having exhaustively exercised my reason, the pros and the cons, and not being able to come up with any sort of conclusive decision, I flipped a coin. And the coin said to hire the guy. So I hired the guy. And it was a part of that key 2016 inflection. I thought I was good at sales, right? I just finished saying that. Sales was at the bottom of my list, because I thought that I was good at it. At the time, my retainers, I was selling $1,500 a month full-service inbound marketing retainers. And that was a transition. That was a growth. I was proud of having gone from selling no retainers at all and being exclusively project-driven, to selling $1,500 a month marketing retainers, starting to get some recurring forecastable revenue through the door.

This guy came in. And within six months, we had, I don't know, six, half a dozen to a dozen $10,000 a month retainers on the roster. It completely flipped our ability how we looked at what we were able to do as an agency. So it wound up being a brilliant hire-- not that I made a brilliant decision, simply that it was a brilliant move for the organization overall. And ultimately, it was determined by a coin flip.

KD: It's wild that it all came down to a coin flip. But it's like that the lesson here is, well, I think it's an important exercise to list all of the roles and responsibilities that you currently act for and then have an initial draft of the list of priorities or the order in which you want to replace those. But you have to be comfortable diverging when certain opportunities shuffle up or shake up what that perceived priority list is.

MS: Yeah, I think that's probably an important lesson or take-away, broadly-speaking, is as a leader, have ideas, have thoughts, have opinions, and then absolutely be detached from them. Just be as detached as possible. Just recognize-- I alluded to this previously, but your thoughts and your opinions, everybody, your mileage may vary. You may disagree. But from my perspective, having lived 40 years and having made more mistakes than wise decisions, what I've learned, over the course of time, is that my assessment of things is, in so far as I do not have perfect knowledge, subject to imperfection. And there is nothing that I have perfect knowledge regarding. So constantly, I am attempting to be mindful of the fact that what I think, I need to rank, sort, how confident I am in my thoughts and in my perspectives and in my opinions. And generally speaking, what that has done, or the conclusion, the key takeaway there, is absolutely be attached. You have to have some thoughts. You have to have a vision. You have to be moving towards something. But absolutely recognize that you may be wrong. And what you're moving forward towards today may not be what you should be moving towards or will be moving towards tomorrow. And that's OK.

So I think there's an element of detachment from your prioritization, your values, your vision, that is necessary, if the agency, if you are going to be able to evolve as an agency, and ultimately put other people in a position to succeed where you might not have succeeded as much. I think also, one other takeaway that's related to that is, when I think on the hindsights 2020, what are the things that I wish I had foreseen in the process of replacing myself, even when I was detached and even when I allowed things to proceed, when I entered into that dialogue in a manner that, I don't know, manifested some measure of humility that allowed me to be adaptable in my perspectives, still one thing that I did a terrible job at-- which I'm still trying to do a better job at-- is planning for redundancies. If you're replacing yourself, it generally means that you're replacing-- the things that you do as an agency leader are typically the most important things in the agency. So if you're replacing yourself, it means that you're replacing-- you are putting the most important responsibilities in the current state of your agency into the custodianship, into the hands of somebody else. And any time that you do that, so now you have individuals who are responsible for very important things day-to-day functionally within your agency. And they may leave. They may leave on good terms. They may leave on bad terms. They may leave expectedly. They may leave unexpectedly.

But at the end of the day, there's an impermanence to any sort of organizational structure. And you have to be able to just plan for that. Plan for redundancies. Build them in. Even if you don't have 100% redundancy, try and get to 50%, 60% redundancy. And always have a roadmap for, OK, if I do need to get to 100% replacement, how would I do that? How could I shift people organizationally, rather than having to hire from without? Do I need to hire from without in order-- you're in a much better situation as an agency owner if you have a game plan that involves shifting existing personnel into redundant roles than having to hire from outside to plug a hole that appeared unexpectedly.

There's going to be a lot less friction, a lot less turbulence, a lot less morale loss on the team overall, if you have a way to fill any hole with existing team members. Ultimately, that involves typically you're promoting up rather than hiring out and filling a hole.

KD: Well, I would imagine that, yeah, as you've outlined it, the growth trajectory, just it helps team morale at large. But functionally or operationally, you just need to alleviate or remove singular critical points of failure as you put these business-critical responsibilities on somebody that's not you as the agency owner.

MS: Yes, that's it. I think that's a great way to phrase it. You want to have as few critical points of failure as possible. and the way that most agencies who have finite budget-- you have 20 needs, and you have budget to fill 5 of them, or whatever the case might be-- the way that you're typically going to be able to solve or resolve those critical points of failure is through existing personnel.

KD: Mike, it's been a pleasure talking to you. We're just about out of time. But I have one final question for you. We try and wrap every episode with this. What is the weirdest part of agency life?

MS: I don't know. I wish I would have watched previous episodes to the end than I would have known that this question was coming, and I could have prepared for it. I think the conundrum-- so I'm shooting from the hip. But the first thing that jumps to mind--

KD: That's what we look for, by the way. We want to shoot from the hip on this.

MS: I think ultimately, the one thing that's been toughest for my noggin to reconcile, from 2008 until 2020, is a

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