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[upbeat music] Hey there. It's Scott Amenta here, the founder of the Chief of Staff Network. Today, we're joined by Dion Valle, a former chief of staff who made a rare pivot into clinical work.

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Dion is now a registered associate marriage and family therapist working with the Center for Mindful Psychotherapy in the San Francisco Bay Area and across California.

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In this conversation, we unpack a dynamic many chiefs of staff will recognize, the blurred line between being a trusted operational partner and becoming the emotional container for a principal, especially during high-stress moments like M&A, leadership conflict, and major personnel decisions.

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Dion shares what he did well, what he'd do differently with the benefit of training, and how those experiences ultimately pulled him from operating to therapy. Let's get right into it. Dion, welcome to the podcast.

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So nice to have you here. Thanks a lot, Scott. It's great to be here.

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I don't remember what year we actually met, but it was a long time ago, I think right when you were getting started as a chief of staff, and it's really fascinating to see kind of the path that you took along the way, and I'm excited to dig into it with you today.

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Yeah. It really has been a long time, so that must have been probably twenty eighteen, which is when I think I started, so well over seven years now. Feels like a lifetime ago. A, a lot has changed in both of our lives.

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[chuckles] Yes, absolutely.

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We're gonna talk about kind of your role moving as chief of staff, going back to school, becoming a licensed therapist, and kind of all of the things that you dealt with as a chief of staff, sometimes playing therapist to your principal and kinda what that means now with the kind of formal training as a therapist.

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Before we do that, I'd love to just learn a little bit more about your career path. Maybe you can tell us the story of how you became a chief of staff and how you ended up going, you know, back to school.

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Yeah, absolutely.

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So prior to becoming a chief of staff, I was working in consulting, so I have a engineering background and was really focused a lot more on business process improvement and from an engineering perspective.

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And in that role, I came to realize that what I really loved about the job was people and, like, those moments of human connection, and that's what kind of led me towards looking at chief of staff roles.

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What was the decision-making process that took you from operator to getting your MA in counseling psychology?

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In my chief of staff role, you know, that role was a lot more people-focused, but our company at the time was going through an M&A process and, you know, it was a really, really stressful time for the company.

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Our executive team was under a lot of stress, and there were a lot of just interpersonal challenges on the team that were coming up.

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What we actually ended up doing was bringing in an executive coach at that time to kind of help manage and handle a lot of those interpersonal challenges and conflicts, and that was kind of the first time that I was introduced to coaching.

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And I worked really closely with the coach that we brought on and started to learn more about her career path, like what she was doing and really saw that as a viable career path for me at that time.

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And then, you know, as I learned more about coaching, therapy was never really on my radar at all professionally, but what I realized was, in kind of learning more about the differences between therapists and coaches, is that, you know, therapists are really focused on what's deeper, like, what's really beneath the surface, and how people's early childhoods and trauma show up in their day-to-day lives, and that's something that coaches don't necessarily focus on.

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And so I've had this realization or this understanding that that's where my passion lies. That's really what I wanna focus on, and, and that's how I ended up making the pivot.

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Did you end up pursuing coaching first before going back to get your MA? I didn't.

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I spoke to a lot of different coaches, so basically, as many [chuckles] coaches as I could find, I talked to and really tried to get to understand, like, what their job was like and how they made the decisions to get to that path or get to that role.

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And through those conversations, I realized that coaching wasn't for me. What surprised you most about formal training in psychology?

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Really just how universal some of these concepts are and, and by concepts, I mean, like, everybody has trauma, um, you know, to different degrees of course.

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But getting to study early childhood development and how so many of our current challenges, anxieties, conflicts are rooted in those environments, that really, I think, helped me get an appreciation for a lot of what I saw in my chief of staff role.

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And that, like, no matter how successful, however we're defining that, someone is, they still have, you know, the same human wishes and desires and sensitivities, and so I think that's what was really impactful for me.

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Did you end up having to, quote-unquote, "unlearn" things from your consulting chief of staff days that didn't translate well into therapeutic work? Definitely.

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Yeah, I was working in a really fast-paced startup environment, and so as chaotic as it was, you still have very specific frameworks and metrics and goals that you're setting and meeting.And so I think for me, there was a lot of, and still is a lot of trying to unlearn that structure.

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You know, there can be a lot of structure in therapy, depending on, like, the type of therapy or modality that you're practicing.

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But in terms of how I practice and where I think a lot of the really powerful change can come from, is really just not knowing where you're going, not knowing exactly what you're doing, and just kind of figuring it out in the moment.

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What kind of originally drew you into chief of staff work? Was this something that you were looking for? Was this something that you just fell into, something that you interviewed for?

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Prior to becoming a chief of staff, uh, I was working in consulting, small consulting company, mostly working with utilities, and it was very much focused on, like, business process and was working with a lot of engineers.

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You know, and reflecting on that role, what I really liked most about it was working with people.

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And I knew that I wanted to get a little bit more out of the numbers and, like, the weeds of stuff and move into a more people-focused role, and I didn't know exactly what that would look like.

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But a good friend of mine...

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You know, I didn't know about the chief of staff role at the time, but a good friend of mine basically introduced me to the role and told me that this would be, be perfect for me, and that's when I started to shift and start to look for those roles.

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And obviously, chief of staff roles can have a very people-centric focus. I know plenty of chiefs of staff that are basically de facto leaders of HR or people ops teams. Was it that way for you?

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Was it something that you had to shape, you know, after joining the company?

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So the company I was at, uh, there was already a chief of staff kind of when I came in, so I was replacing him as he moved to a different role in the company.

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So the way that he had set up the role, I'd say it was already, it was already pretty people-focused.

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He was working a lot just directly with the CEO on kind of managing the CEO's time and getting a better understanding of how he was prioritizing all of his different projects.

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So there was a lot of that, I think, built into the role from the beginning.

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And was there a moment that you found that you started to really spend more time on, like, the human side of the job, not just kind of pure execution or, or more focused on operations? Absolutely.

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When I joined the company, we started going through an M&A process. So the company was growing really, really fast.

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We were looking at different avenues to get more capital to keep growing, and that's an extremely stressful process.

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And so what I started to see is, like, all of the senior leaders, the exec team, they were just in this really intense process, like, you know, working a lot, really stressed out, and that's when I started to really pick up on a lot more of the interpersonal dynamics between the exec team and the relationships between people on that team.

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That was the big shift for me, was starting to notice that more and starting to really get interested in how that was impacting the business. Yeah.

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So the introduction of a brand-new culture, brand-new team, something that everybody now had to adapt to, was that the kind of start of the through line for you in terms of, like, your general interest in people and how people come together to kind of form an organization and the culture within?

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That ended up being, I'd say, part of it.

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But even prior to that, there were a couple new leaders who were brought into the executive team, kind of outside of the original founding group, that had a lot of influence and power in the company.

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And so in the early stages of the M&A process and sort of, like, deciding which direction we were gonna take, you had kind of the original founding team, you had these other leaders coming in with their own ideas, and so there was a lot of conflict and clash kind of between these different people, different value systems, and that was really where I was focused.

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And what was the day-to-day experience like for you as a chief of staff? I know you were obviously spending a lot of time with your principal.

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We're gonna get into this in a little bit about kind of like the therapist dynamic that you were playing, you know, with him.

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When did you start to kind of feel like that role was shifting, again, from, like, pure operations to, "Hey, how do I help level up everyone around me as well?"

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You know, I think over time, because I spent so much time with my principal, like, we were just...

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You know, I went to all the meetings he went to, and he had an EA also, so the three of us were meeting a lot in our group.

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And so I think just, like, the sheer number of hours that we spent together, I feel like we just started to build a really close relationship, and I was just in this unique position of spending so much more time with this person than anyone else, that that's when I started to notice some of those dynamics.

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In chief of staff roles, generally, you know, I've heard plenty of stories of chiefs of staff in some ways playing therapists, right, to their principal and, you know, maybe not doing all the things that a, a licensed therapist might be doing, but certainly being kind of the trusted confidant to the day-to-day experience of being a founder, CEO, or executive leader.

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Where do you draw the line between kind of being that trusted confidant and then maybe accidentally stepping into a real therapist position now that you can kind of speak from a, a position of authority?

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I think it can be a really fine line, like this line between personal and professional.

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When I think about the professional side, it's really focusing onHow the either behavioral patterns or emotions of your principal are impacting the business specifically.

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You're always coming back to like, okay, how are these behaviors or feelings that are coming up for you impacting decisions we're making?

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Whereas I think the therapist role is when you're maybe starting to get to like, okay, what might be below these patterns or feelings on like a more personal or human level?

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That's when you might be starting to cross that line.

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Were there any moments in your chief of staff career where you felt like you had stepped over the line being more of a therapist helping him to process his emotional, you know, needs versus more classic operational support?

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Yeah.

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There's one example that clearly comes to mind where there was, yeah, like a really highly charged kind of emotional moment between my principal and another executive in a particular meeting, and I ended up, after that meeting, spending some time with my principal where some really serious personnel decisions looked like they were going to be made based off of that exchange in that meeting.

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And so in that situation with him, I felt like what was really needed in that moment was just a little bit of processing, a little bit of containment of, of emotions that were coming up for him since I felt like it might lead to this really big decision.

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But we couldn't focus on really the decision itself because the emotions were so high. So that's one moment that really comes to mind where, yeah, where I maybe stepped over that line a little bit.

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Were there any moments where you think you did well in terms of offering that emotional support?

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And now looking back as a licensed therapist, what do you think you got wrong because you didn't have kind of the official clinical training?

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I think in terms of things that I did well, even though emotions were really high, I was able to stay pretty grounded and regulated myself, and in turn, I think was able to provide that to my principal.

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You know, that's something that definitely translates to the therapy room.

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And then in terms of what I could have, I think, done better is because, you know, I was really making an effort to stay on that professional side of the line, I think that I actually moved to action in terms of, okay, like, this is what we should do from, like, a business decision-making standpoint.

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So moving to that a little bit too quickly instead of really just sticking with the feelings that were coming up, looking back, I would have done more of that. Yeah, that's interesting.

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That kind of stymies the growth in some ways by being maybe over results oriented rather than kind of sticking with, okay, how do we feel about this particular situation? How do we address those feelings?

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And then how do we react differently maybe the next time it comes up? Yeah, absolutely.

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I think that's one of the biggest things I've learned as a therapist is that a lot of the growth really comes from sticking in that discomfort, like in those difficult feelings as they're coming up and exploring them, rather than trying to get rid of the discomfort and move towards like more of like a rational or logical decision or explanation.

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I guess sticking with that train of thought, are there subtle signals that you look for, now put your chief of staff hat back on, you know, that a principal may be asking for regulation in a given situation versus advice?

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I know a lot of chiefs of staff, they get to know their principals really, really well, and they can almost like step into their shoes and think about like, "Okay, the decision that I would make in this situation is probably the same decision this person would make."

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And so for me, I think when my perspective or what I thought my principal might do in a situation and what he was actually doing or talking about doing were really, really off, that was a signal for me that maybe that this decision is feeling either really impulsive or it's coming from more of like emotions driving the decision rather than logic.

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Looking back kind of at your chief of staff experience and now your work in therapy, which skills have kind of transferred well from one to the next?

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What have you kind of carried with you that maybe other therapists don't have kind of that background in? You know, [chuckles] as much as

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I say that the framework, metrics, goals, like that structure, unlearning that, I still think there is like some amount of that that's important.

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You know, I think about like my background as an engineer and also what served me really well in the chief of staff role and in like the startup environment was using that like more analytical part of my brain to just take, you know, these problems in a startup that are so amorphous and you don't have a lot of information and using that analytical part of my brain to just like draw connections between, you know, different parts of the organization or, you know, different parts of our strategy.

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And, and so I think that does come into therapy, like being able to work with a person and really connect the dots between all their different experiences and using that information.

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There is a similarity there, and I think a lot of therapists don't have as much of that. I think that's a really interesting point.

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Like this concept of leading without authority is obviously key to how the chief of staff operates within organizations. You know, a therapist is there as a guide, right?

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They're there to ask interesting questions and help you open up in ways that-You might not in kind of a, another situation. And chiefs of staff are very similar.

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We're there to, you know, help get the best out of people in whatever way is gonna make the most sense given the situation. Yeah, absolutely.

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I think-- I know in my case as a chief of staff, you know, there were decades of experience, like a gap between my principal and me, and really just, you know, me having such a different framework from my principal, being so different, having such a different background and different experience, being able to really take in like what my principal is saying and listening and reflecting that back to them, and then also offering my perspective, which is going to be different, but, you know, hopefully also valuable.

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That's something that was really, really important in that role and also really important in therapy. How do you think about influence now?

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So, you know, when the goal is not alignment in the business sense, like what is the outcome for the OKRs, but instead safety and growth for a client, has it been easy to kind of make that transition?

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It's been interesting. [chuckles] I think in the therapy room, I'm extremely wary of my influence because, you know, the power dynamic has shifted in, in the therapy room.

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The therapist really is the person who's in the position of power, which is not how things are in the chief of staff role.

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And so when I think about therapy, my goal is for my clients to really get in touch with their own sort of inner voice, their own authentic sense of self that's going to guide them in the right direction, that's going to make decisions that are the best for them and in their lives.

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And so I think that my influence can really easily get in the way of that.

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And at the same time, I think for people who really are feeling lost or they're like not at all in touch with that internal barometer, a little bit of influence, like a little bit of nudging in the right direction can be helpful.

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So yeah, I think it's useful in small doses, but I am really, really careful about how my influence is showing up in the room. Let's talk about some practical guidance for chiefs of staff today.

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So, you know, if you were to put yourselves back in those shoes, if a COS wants to support kind of their principal more effectively without playing therapist, what scripts, boundaries, referral moves kind of work?

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This question is reminding me of, of a sort of structure that we had in place at the company that I was at when I was chief of staff, where we had a small group.

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There were three of us, three chiefs of staff for different principals in the organization.

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And so we each had these individual relationships with our principals, and at the same time, like, the three of us were working in a group kind of like behind the scenes and doing a lot of work to sort of manage a lot of those interpersonal relationships and conflicts.

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And so they started to call us the small council, [chuckles] which was pretty cool.

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But that structure I felt like really worked well for us, and I'm not sure if that's something that is common now, but yeah, that's something that comes to mind.

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And in terms of kind of organizational support, you know, when it comes to coaching, HR, leadership development, what do you think is the right blend of kind of what the company provides to their executive team or more broadly?

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I think that coaching in general is something that is great for organizations to invest in for their employees, like for their leaders in particular, like for their executives.

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And I think therapy is another benefit that is really important, like understanding the difference between those two.

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You know, some chiefs of staff I think may be naturally more inclined or interested in playing kind of more of this role that we're talking about today.

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But chief of staff looks very different, and if someone is not interested in playing that role or like not as equipped to play that role, I think it's still really important for principals to get that support or have that space.

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And at the same time, I think that chiefs of staff can work really, really well with coaches like we did in our organization.

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And I think it would be really interesting to think about how chiefs of staff might work with the therapist of a principal.

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I think that's something that we never did and something that I haven't heard of happening, but I think like that could be a really interesting collaboration.

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In your mind, what does a healthy chief of staff to principal relationship look like to you now?

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So looking back at your experience, was that a healthy relationship or are there things that you might have done differently, kind of given your lens on attachment systems identity?

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I think that trust is probably the most important thing, just a relationship that's built on trust and openness and honesty.

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I think that having this relationship where honest and direct feedback can be given both ways from principal to chief of staff and vice versa, I think that's really, really important.

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I think it's rare to have relationships where people really feel like they do trust the other person and there is this sense of safety and sense of openness and, you know, willing to maybe be a little bit vulnerable at times.

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You know, as a therapist, I see how powerful and how life-changing that can be.

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Some version of those qualities that make sense, like in the context of a business, I think can really be a game changer for principals and, and for chiefs of staff also.

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I think it, it works both ways.If you were to leave chief of staff with one permission and maybe one word of advice, what would they be? I would say don't undervalue the human side of the role.

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I remember one thing my principal told me that stuck with me, which was that at his level, like at the executive level, he said every problem is a people problem.

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And so there are many things that can't be fixed with the best strategy or the best framework.

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Uh, and so I think really understanding each other as humans and being able to work with different types of people is key to succeeding at that level. Dion, thanks so much for joining us.

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Thanks a lot for having me, Scott. This has, yeah, been a really interesting conversation. That's it for today's episode. A few moments worth sitting with.

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First was Dion's distinction between supporting a leader professionally, how emotions and patterns are impacting decisions, and what it means to cross into the deeper why underneath, quote, unquote, "where therapy, training, and ethics really start to matter."

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Second was his reminder that at the executive level, every problem is a people problem. Strategy matters, but it rarely works without trust, regulation, and honest feedback inside the leadership team.

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If you enjoyed this episode, please share it with the chief of staff or operator who's navigating the human side of leadership.

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If you want more frameworks, peer support, and programming for chiefs of staff, you can find us at chiefofstaff.network. Thanks so much. We'll see you next week.

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