Leah Warwick: Hi, everyone. I’m Leah Warwick, and you’re listening to The Admin Edge. This episode was recorded at the Administrative Professionals Conference in Seattle, with host Debra Coleman, Owner of The Seat Upstairs, and guest Cherron Castillo, Founder of Fruitful Training Group and a trainer at this event. Now, let’s dive right into Cherron and Deb talking about how to get in touch with and show your strategic side, straight from the show floor at APC 2025. Deb speaks first.

00:00:41

Debra Coleman: You often mention the idea of an administrative professionals strategic edge. I would love to hear, really, how, when you talk about strategic edge, what do you mean by that, and why is that such an important quality to develop, do you think?

Cherron Castillo: Absolutely. I can be a very logical, analytic person with words sometimes, and so when I think words, I think, like: What does it mean? Or what comes to mind or what word/pictures?

And so when I think “edge,” almost like if it’s the edge of this table or the edge of a cliff, there is like a line. An edge can be used to cut or to slice or to get through or to pierce. So, when I compare that with strategy for an admin, thinking about thinking, and how do I pierce through the noise? How do I pierce through competing priorities and people who have competing attitudes and conflict, etc.?

00:01:53

So, the strategy of thinking about: How do I sharpen myself? How do I sharpen that edge to cut through? So I really think it’s a lot about starting first with self, with me. How am I connecting, cutting through all of the noise to hear what my leader really wants? What do they really need? What are the words that are unspoken? How am I then also connecting what I do to what they care about? Have you heard of that phrase WIIFM, what’s in it for me, W-I-I-F-M?

Debra Coleman: Yes.

Cherron Castillo: Yeah. And so to always have that in mind because that’s what they’re thinking, “What’s in it for me?” the folks who are participating in events that you’re coordinating, the other admins that you may lead. “What’s in it for me when you’re asking me to do… What’s in it for me when I show up to this meeting? What’s in it for me if we go this way, and how do I connect what I do with what’s in it for them?” I’m always sharpening myself, sharpening my message, sharpening my perspective, and sharpening and using concise language and words. So that would part of a strategic edge, I think, as well, which we’ll talk about.

00:03:09

Debra Coleman: Cherron, throwing in that communication angle, which is, again, another missed area, I think, and not discussed enough in our world.

Cherron Castillo: Absolutely. So, again, the way—thinking about thinking ahead, taking the initiative, sharpening the word choice, I have to practice this all the time with being careful to not over-apologize, for example, or saying things like, “I’m just… I was wondering… Well, maybe, if we could… What do you think about…” So there’s always this seeking of the approval versus, again, the confidence to say, “Based on what I know,” for example, or, “Thank you for allowing me the opportunity,” or, “Thank you for your patience while I was…”

00:04:01

So, I think the language should be sharpened. There are so many edges that we can think of or different ways that we could go with that, for sure.

Debra Coleman: Excellent description. That’s very empowering, too, the description of what a strategic edge is. And you’re right, if you think of it that way, it just sharpens you up, maybe makes you stand up a little straighter.

Cherron Castillo: Absolutely. Fantastic. Something I learned a while back was a problem-solving two-step, and so I want to share. I call it a problem-solving two-step. That’s what I dubbed it.

It’s this idea of, when you see a problem, the idea is—step one: What you can do is create intention statements. So, if I see or notice a problem, something going on, a process, etc., what do I intend to do about it? So that’s where I’m going to start.

00:04:45

And if I create at least two, three intention statements, “I intend to… I intend to blah, blah, blah… I intend to contact this person…” you’re now starting to shape a plan. What do I intend to do?

And then step two, though, which is think is something to really work on from that administrative position, is: Now I want to think through, what are potential questions or objections my leader may have to the thing that I intend to do? That way, when I show up in the room, I show up with a plan and not a problem. Also, we are now as iron sharpening iron. I show up in the room to say, “Okay, here’s the problem that I saw. Here’s what I intend to do about it, and here’s what I think you’re going to ask. I know what you want to know, boss, is if I intend to do this, what about A, B and C? So, here’s what I’ve thought about those things, and then you may want to know,” blah, blah, blah, “and here’s what I’ve thought about.”

00:05:46

So, it’s literally [that] I’ve laid out: Here are the different roads or here are the different paths, or here’s a decision tree. And then, even from that, optimally, based on what I know, I would pick Option B for blah, blah, blah.

So, I come in. Again, it’s to like, “Oh, I did, but here’s a problem,” and now I kind of lay a problem at their feet. That kind of jumps into a problem-solving other things.

So the two steps. Step one is: What do I intend to do? Create some intention statements. And then step two: Now how do I overcome the objections or questions? So I’m now thinking like the leader, thinking down the road, thinking strategy and vision and not just what’s right in front of me.

Debra Coleman: I love that. You know what I was envisioning when you were describing that? Taking ownership.

Cherron Castillo: Absolutely.

Debra Coleman: Taking ownership of whatever it is that you’re presenting or working through.

Cherron Castillo: It’s mine. I own it, and I’m going to… You picked the right one today. [laughter] And we’re going to get it done to completion, absolutely.

Debra Coleman: Thank you, exactly. That is so true. That is so needed because, you’re right, we need to get out of “I only do this task” mentality, and really look at it from more of a 360: “How does this actually connect the dots?”

00:07:00

Cherron Castillo: Yes, which goes into systems thinking even. How does this bump into that, bumps into this, bumps into that? And realizing the gravity of the role. I impact and touch so many things. It’s never a “just.” Nothing that you ever do from the administrative role is a “just.”

And so even if we start there, with removing those mental blocks of who we are and what we do, I think it’d really make a difference.

Debra Coleman: A huge difference, especially in today’s workspace, when so many of us are feeling a little pressure about job security.

Cherron Castillo: Yes.

Debra Coleman: We need the thinking—

Cherron Castillo: And then that starts—it becomes a bully. Job security, it starts to bully us and we’re like: Okay, yeah, no, keep my head down and don’t think ahead. Don’t try to help. Don’t do any more.

00:07:49

I think some of that comes with the relationship and knowing, understanding your leader, and asking—again, coaching the leaders on creating that space and opportunity, drawing out of them their thought processes and giving them space, because that helps to have the sponsorship on the other end, too, because you can go in fighting all you want, and then if your leader is like, “Go have several seats,” right, and so then you have to—

One of the things I heard once is: If you can’t change the people around you, then change the people you’re around.

Debra Coleman: Ooh, powerful, yeah. And that could be a harsh reality some may have to face.

Cherron Castillo: And that’s concerning, especially in the market and all the things. I did not advise anybody to go quit a job.

Debra Coleman: No, no, no, no. Know your value.

Cherron Castillo: Be mindful and be strategic, even for yourself, in what a plan is. You don’t have to do anything haphazardly.

Debra Coleman: Good advice. Well, we all might be thinking strategically every day, but, if no one notices—and again, this a beautiful segue into kind of what we were speaking to or touching on. It can be tough then to get the credit we deserve.

00:08:59

Cherron Castillo: Absolutely.

Debra Coleman: We can go in with that mindset, but then no one recognizes it and we think, why did I do this? So what’s your go-to move for adding that strategic value, or maybe working through that when we’re faced with that nonrecognition? Or does it matter? That’s fair to ask, too. How heavy a weight does that recognition really play? I know it can be subjective, depending on what we’re doing, but—

Cherron Castillo: A phrase I use that I pulled from the old movie or film with the guy who wore the mask—

Debra Coleman: There are so many.

Cherron Castillo: Many, many, many years ago. It was a white, long ghost mask.

Debra Coleman: Yes, yes, yes. Scream, I believe.

Cherron Castillo: The call was coming from inside the house. That can be applied in a couple of different ways. You can go several directions with that. The need or the desire for recognition, I think, is very natural. For some, it’s heavier than others, the need for the validation.

00:10:00

And so when I say “the call is coming from inside the house” that way, what I want us to condition ourselves [to] is: How do we encourage ourselves? And how do I appreciate me and also find a support community of those who appreciate me? Because it may not come from the direction you want, as much as you want it to.

So, the reality is: What do I do then, if it doesn’t come? This, now, can tap into resilience.

Debra Coleman: Whole other show

Cherron Castillo: Yes. We don’t have time to go there. And so the call can come from inside the house, and so one of the things I encourage is to keep a brag book for yourself. What are some things that you’ve accomplished? And then sharing those, I think, making your boss aware of the things, advocating on your behalf, like, “Okay, here are some…” Even if you frame it as a “keeping you in the loop,” and they get to see some wins that happen that way.

00:10:54

Of course, we’re not doing the work just for the recognition; we’re doing it to do a great job. So recognizing and appreciating ourselves, patting ourselves on the back, talking with some friends and getting that, so that we have that support system in place, even if it doesn’t come from the leader.

But then also, number two, what I was just mentioning was: How do I advocate on my own behalf? Not coming like: You should be thankful. You should thank me. Where’s my applause? Where is my appreciation?

But if you’re feeling that it’s not coming—again, treading lightly and carefully—this would also then bump into another topic of assertive communication. Assertive communication is not aggressive communication, which is something I talk about a lot. When I talk communication, I call it the Goldilocks Zone, to be just right, because passive is too cold, aggressive is too hot, and assertive is just right.

00:11:50

And so the assertive admin will also advocate for themselves and say, “Hey, I’d like to… Do you have a couple minutes? Something that would really help me…” So, if I frame it that way, not “you don’t do this and “you’re not.”

“I realize about myself…” If I start there, I realize about myself that small words of affirmation are beneficial to me, or an occasional thank-you email or something like that. Am I willing to mention that to a leader? Do I feel like I can? Which, oh my gosh, that comes into another topic of psychological safety. Oh, my gosh.

Debra Coleman: See the complexity?

Cherron Castillo: Yes!

Debra Coleman: It’s an onion. There are so many layers.

Cherron Castillo: Yes. And so how do I advocate? Again, I may have to bring it up, and so that’s building up my reps and building up my confidence to say, “Something that would really help me out is I love…” or “I like” or “I appreciate words of affirmation. It would really help me out if occasionally…that would kind of be fuel for me if, occasionally, an attagirl or attaboy or just a quick thank you.” Kind of leave that. Kind of plant that seed and see what happens, and then you can kind of water it, but that’s not going in, demanding acknowledgment or recognition, but also, if it doesn’t come from that way, I’ve still got a support system elsewhere that fuels me, that keeps me going.

00:13:31

Debra Coleman: I love that.

Cherron Castillo: I heard it framed this way, to make a request not a complaint. “You don’t recognize me,” or “I’m not feeling appreciated,” or “I do so much around here.” Now, those things are all true, but, if you think about it, what is the other person hearing, or how are they hearing it, or how are they receiving it? “Oh, there you go, complaining again,” or “Don’t you get a paycheck? Isn’t that enough?” [laughs]

00:13:59

So, we want to frame and make a request, to the extent possible, instead of making it a complaint.

Debra Coleman: Excellent advice. I love that. Thank you, Cherron.

Cherron Castillo: Absolutely.

Debra Coleman: Do you have time for a listener question? We just have one.

Cherron Castillo: Yes.

Debra Coleman: I think it really leans into, again, that confidence that you speak of. So we have listener that asks: If my executive’s idea of strategic doesn’t fully match mine—like, again, speaking to that definition that you kind of alluded to—how can I bridge that gap and still demonstrate my value? Maybe they believe in strategic as a principle as well, but maybe their edge doesn’t align with yours.

Cherron Castillo: Yes. I’ll have to circle back to the assertive communication. I think what happens a lot is they talk about having the elephant in the room. I say that we’ve got to minimize or escort the elephant out of the room by having conversations.

00:14:57

A very direct conversation—again, leading with “I” language or “I” statements. “Hey, dear leader, I want to get a sense of your definition of strategy or what it means to be strategic. I’m working on being more strategic.” So there’s some vulnerability there. “I’m working on supporting you in a way that’s more strategic, that helps to uphold and support, to get you where you’re going.” Balance asking those kinds of questions of not just “What’s the task?” but “What do you need? What are your goals for this quarter?” Talking in goals and things like that to understand what they care about.

But I think the direct conversation of: “What does strategy look like for you, in your role, dear leader?” And then, “What does strategic look like for me supporting you to get there?”

00:15:49

So, here, their answer or their version, and then also say, “Hey, I’d also like to share…” It’s almost like a calibration conversation. So, again, the willingness to go in. Again, if we’re softspoken, if we want to work on building that confidence first to get in the room, maybe we practice what we’re going to say a little bit. “Hey, I wanted to ask you a couple of questions about strategy. First, I’d like to understand what strategic means for you, in this role, and what some goals are that I’m working to help you accomplish, because I want to have the big picture in mind.”

And then also, “What does strategy look like for me, in this role? What would you consider strategic?” And so if I have the alignment conversation, now we need to figure out what’s realistic or unrealistic, or what are their true expectations, and can I meet those?

00:16:44

The assertive communication then is even as we’re talking about it, “Okay, so I think your strategic is…” And now I share what I think my strategic is. “Where is there overlap, and where is that miss?” And then even asking the question, “How can I work to close the gap?” But notice even—what just came to mind right now [is] a lot of these conversations that I’m talking about are coming from a place of confidence. That may be the starting point because somebody may be listening right now, like, “Girl, that sound good, but I can’t do that.”

And “Who told you, you can’t?” would be the first question. “Now, is it you that told you, you can’t? Or is it they that told you that you can’t? Is it maybe experience that told you, you can’t?” Because sometimes it’s—

Debra Coleman: It is, mm-hm.

Cherron Castillo: “Mm, no, I seen the last girl,” [laughter] the last guy, the last person, “and that didn’t work out so well.” So, then it’s working on figuring out, how do I approach this person? Like I have family members who need a softer or a different approach. Everybody is somebody’s difficult person, but most difficult people still also have friends, and so those friends have figured out how to deal with that difficult person effectively.

00:17:51

So, if it’s asking others who are well connected to the person so you can know how to have the conversation, but yeah, I think if you even start with, “Hey, I’ve got a couple questions.” Because, as we also know, there are lots of people in lots of positions who love talking about themselves and their ideas and their perspectives. And so if I set them up to listen and glean…

It makes me think about the Barbie movie. Did you see the Barbie movie?

Debra Coleman: I did. I really enjoyed it.

Cherron Castillo: Did you see, near the end, how when they had to go reclaim the Barbies—

Debra Coleman: Yes.

Cherron Castillo: —what they did? It was an exaggeration, but they asked a question and had the Kens start—

Debra Coleman: Yes.

Cherron Castillo: They had the Kens start talking.

Debra Coleman: Exactly. Good reference, absolutely. That’s exactly—that’s a good visual of what you’re talking about.

Cherron Castillo: Yeah, get Ken talking, and then learn and use that information.

Debra Coleman: Fantastic. I love that. It all starts with confidence and communication, and then you go from there and assess as you go.

Cherron Castillo: Yes, indeed, and connecting to their long-term goals, their range. How does my task connect to that? And helping them see how what I do connects to that as well, but I’ve got to know it first so that I can then communicate it.

Debra Coleman: Yeah. It all comes back to that strategic edge, building and sharpening that strategic edge.

Cherron Castillo: Yes.

00:19:04

Debra Coleman: I love that. Well, Ms. Cherron, honestly, I could keep you here all day, and I know you have fantastic sessions coming up that speak to a lot of this in many different ways. But if those listening want to learn more about you and your services and what you offer, where can we find you?

Cherron Castillo: Yeah, so LinkedIn—shameless plug and also reprimand—get a LinkedIn. Business is conducted on LinkedIn a lot, right? So, I can be found on LinkedIn. My name, which is in like the programs, but my website is fruitfultraininggroup.com, so Fruitful Training Group. I want training to be fruitful. I want people to walk away with things.

00:19:52

So LinkedIn with my name, Cherron Castillo, and then Fruitful Training Group, as well, is another place to find me.

[music playing]

Leah Warwick: Thank you for listening to The Admin Edge, produced by the American Society of Administrative Professionals, original music and audio editing by Warwick Productions, with audio and video production by 5Tool Productions. If you liked this podcast, please leave us a nice review, five stars, and subscribe. If you’d like to submit a listener question, you may do so on our website at ASAPorg.com/podcast.