098: What AI Can’t Do: Leading with Empathy in a Remote World with Sarah Cuesta (Office Hours)

Episode Transcript – Sarah Cuesta, Optidge HR Manager

Danny Gavin Host

00:05

Hello, I’m Danny Gavin, founder of Optidge, marketing Professor and the host of the Digital Marketing Mentor. Today, I’m joined by our own HR Manager, Sarah Cuesta. 

Sarah Cuesta-Dawson is a SHRM-CP certified HR strategist and People Ops consultant with 20+ years of experience helping individuals and teams thrive—from therapy rooms to fast-scaling remote agencies. 

In her role at Optidge, she supports growing teams in building the trust, structure, and communication they need to actually work well—together and long-term.

Today, we’re going to discuss why team management still matters in the age of AI. So the topic of many of our internal meetings lately has been the rising concerns of using AI. As marketers, we know that AI can write your emails, but from an HR perspective, they can’t resolve conflict, give feedback with empathy or even build trust. That’s where real leadership still matters and that’s why we’re talking today. So how are you doing, Sarah? 

Sarah Cuesta Guest

01:18

I’m doing really well, and yourself. 

Danny Gavin Host

01:20

I’m doing great. So, for those who don’t know you, what’s your story and how did you find your way into the world of HR and people ops. 

Sarah Cuesta Guest

01:27

Well, for me it wasn’t a traditional path into HR. My background is actually in clinical hypnotherapy, so I dealt with people in high pressure roles people like first responders, medical professionals, entrepreneurs and I helped them manage anxiety and build confidence and really shift stuck patterns. So I actually logged over 12,000 hours of one-to-one work. So there were a lot of conversations with people in tough moments where performance and emotion and identity were all kind of tangled up. 

01:56

And then I moved into business ownership and coaching and I kind of realized that there were the same patterns in teams as they were in individuals, but they just looked a little bit different. So you would find people avoiding conflict. You’d have people struggling with visibility and reacting emotionally under pressure and, you know, managers became unsure how to give feedback and not trigger defensiveness in the person they were going to be talking to. And then you’d have team members who maybe had been stuck after making a mistake and they’d lost space and they didn’t really know how to rebuild trust with their manager and also with their teammates. So I kind of came to the conclusion that if I could help individuals, you know, then maybe I could help teams and move the teams forward in a way that also moved the business forward. 

Danny Gavin Host

02:43

Do you miss the hypno side of things, or are you happy to be in the world of business these days? 

Sarah Cuesta Guest

02:54

I feel I did my time and I feel I thoroughly enjoyed it, and I made a significant impact with the people that I was very blessed to work with, because my clients were fabulous. I found you know I have the greatest respect for people, and doing a job like that really does give you that, because you learn very quickly that what someone presents you with is not what really is going on under the hood, so to speak, and so it gives you a real respect for people. So I thoroughly enjoyed it, but I felt, for my own personal growth, I wanted to do more. It was time for me to kind of have a bit of a change and change direction, which is why I ended up where I am. 

Danny Gavin Host

03:25

Well, here at Optage, we’re very glad that you made that change in direction. So why do you think team management still matters, and maybe even matters more in the age of AI? 

Sarah Cuesta Guest

03:34

AI is fantastic. It can write and analyze really, really well. But it can’t look you in the eye or through the camera lens and say you know, I know things are challenging, but I believe you can do this. You’re not alone, because I’m here to support you. And AI can’t build trust or read the room when someone’s shut down, so it won’t spot tension quietly building between two teammates who used to get on. And it certainly can’t step in and take action when a new manager, say, is stuck a bit in imposter syndrome. It won’t coach them through their blind spots or help them grow in their role. And it can’t step in when someone’s overwhelmed but trying to hide it, or after someone’s dropped the ball and isn’t just looking for a correction but they actually want reassurance that they’re still trusted. So AI can’t help with any of that. 

04:26

Team management is really all about relationships. And when you work remotely, that makes it even more vital because you don’t have the random in-person chats in the hallway as you grab a coffee. So when leadership isn’t intentional, what happens is things can quietly unravel, not out of neglect, it’s just everything moves very fast. So you know it’s easy for communication to get missed and priorities to get a bit blurred and even the most solid of teams can drift, so AI can’t bring people back on course when something just kind of feels off. It’s a fantastic tool, but it’s not a substitute for leadership. So I actually have the view that I think AI is making real leadership even more valuable, not less so. In my humble opinion, I think that teams that are going to thrive will use the technology for speed, but they’ll keep the human element as well. 

Danny Gavin Host

05:22

The points you make really, you know, make a lot of sense because technically here at Optage we record all of our meetings and we have transcripts. So technically one could just read the transcript and feel like they get the gist of the meeting. But all those different points of just seeing how people interact and their facial expressions or their bodily movements, you miss that all in a transcript. I know that’s a very basic use of AI, but it just shows you right. If you’re just going straight to the transcript but weren’t actually part of the meeting, you could miss a lot. 

Sarah Cuesta Guest

05:52

Yes, yeah, and it’s very easy to as well. 

Danny Gavin Host

05:54

So what are you seeing in teams that are overly relying on tech or AI without investing in team management? 

Sarah Cuesta Guest

05:59

There are mainly three patterns I would say that I see happen over and over again. The first is where teams rely more on the tools over conversation. So you can have lots of messages on Slack and Teams and shared documents, but there’s no real shared understanding, because busy doesn’t mean aligned and confusion can creep in and there can be second guessing. So you say you know well who’s really driving this task. Are we going forward? Has this already been decided? All those kinds of questions can kind of pop up and it can lead to friction because you know not that people are trying to do the wrong things or are doing the wrong things, but because they’re just trying to fill in the blanks on their own. You know, and I guess the second thing would be is leaders going off hands off a bit too early because the assumption is the tool’s in place, great, now the team can self-manage, right? No, because without check-ins to talk through and give you know human direction, human leadership, then performance can drop and under the surface you can get frustration building and by the time you kind of realize that it’s kind of effective results. And by the time you kind of realize that it’s kind of effective results. 

07:08

And the last point I would say would be the culture suffers. The culture gets quietly eroded because tools they can’t shape tone. So if leaders aren’t active, the team builds its own version of culture and you have silence and people becoming disengaged or there’s a polite resistance. This isn’t just anecdotal. Even HBR, harvard Business Review, wrote about the fact that remote culture doesn’t carry over automatically. It just will weaken unless someone’s actually making an effort to reinforce it. So technology is a fantastic support too, but it doesn’t create connection. You want humans for that. So I would say use the tech for structure and speed, but the emotional work it still needs a human. So tech should always support your leadership, but not replace it, in my view. 

Danny Gavin Host

07:55

Yeah, and I think, being in a remote environment it’s like it’s really hard because you don’t really know what’s going on. You may assume that everyone’s okay just because they’re responding on your messaging platform, on your email, and you assume that you’ve got your core values so everyone follows them. But if you’re not proactively checking in with people and seeing how they’re doing and actually speaking, then that could all just be one huge facade For all you know. The foundation could crumble right in front of you. So it’s so important to have that human interaction. So how do you balance that? Because we want to be efficient, you don’t necessarily have to jump on a call for every single discussion, but, on the other hand, you do need to have some face-to-face interaction. So what’s your suggestion when it comes to that? 

Sarah Cuesta Guest

08:49

The easiest way is to start before there’s a problem. Expectations really need to be understood and owned, because it’s so easy to assume that people get what’s expected Just because we shared the document with them or we quickly mentioned something in a meeting. You really need to check does this person understand, so they can take ownership and run with it, because otherwise you’re it’s really not fair to the person. You’re not setting them up for success, because I and I would say I really believe that when people know what good looks like, they ask better questions. You know they self-correct, they feel involved, they don’t feel judged. So accountability is best when it’s shared, not when it’s like forced and imposed. 

09:31

And empathy is always in the how, how you get across what you’re trying to communicate. Because remote work, you know it, hides the soft cues. So when someone’s having a tough day, it’s easy to miss. You wouldn’t necessarily know that if you’re working remotely. And that’s why it’s so important to be intentional about setting a tone that’s very open, that’s very warm and collaborative, especially if you know you’re going to have a challenging topic to discuss with the person. You know. Lead with empathy. You could say something along the lines of you know, I appreciate this might not be the easiest thing to talk about, but I want to understand how you’re seeing it. Can you walk me through it? And it sets the right tone right away. You know to be curious and not critical, to be collaborative and focused on moving forward. 

10:21

And I think one thing it’s worth mentioning at this point is that empathy is not about being soft, it’s not about avoiding the hard truth. Empathy is really creating enough psychological safety so someone can take feedback and actually grow from it, because it’s delivered well, it’s delivered with care and it’s a blend of that structure and the support together. And I think if you miss the opportunity to create psychological safety with your team, they’re going to be constantly bracing for criticism. So they’re not listening, they’re defending and it becomes a bit like a tug of war. So the best thing is to make conversations feel mutual. 

11:03

You know those one-to-ones or with your teams, you know. So you’re all looking at the same picture to improve it. And if you find you’ve got a team member who’s disengaged, ask them questions. You know simple stuff. You know what’s motivating you right now. If you’ve got roadblocks, tell me about them, because it’s often not. Someone has a poor work ethic. They might just feel unsure where they fit. So AI, you know, is not going to pick up on that, but a human leader can, and that really is what makes a difference. 

Danny Gavin Host

11:34

And I just want to extra stress one of the points that you made about providing feedback. I know I’ve learned a lot over, especially the past year or two, where you get afraid to provide feedback because you think it’s going to set someone off the rails or maybe they’ll want to leave the company. But I really think that every individual, they want it, they want it, they want to hear what you think they want to be able to get better. I think 99 out of 100 times it’s important to do it and take the advice of what you just said about creating a very safe space and just a culture in general where feedback is normal and that it’s given in a way to help people grow, not necessarily just to call someone out and make them feel bad, absolutely. So I mean those are all some really good points on how to have successful team management in a remote agency. Any other points or anything regarding small teams, specifically when it comes to management as they grow? 

Sarah Cuesta Guest

12:31

Really great. Team management is not forced chit-chat. It’s about making sure that everybody knows who’s doing what, why it matters where to get help. Managers need tools. They need guidance. Managers may think, hey, I’ll just hire smart people and hope they figure it out remotely. So support your team leads. Support your managers to be, you know, approachable, decisive, consistent. 

12:57

When you have newbies, new team members to onboard, please do it well, not here’s your login. Shout if you need me, you know. And then there’s radio silence. Really, do your best to create a plan so you set out their training schedule, you work out who are the key people they need to meet. Why does it matter to that person? And if you can have a buddy system, that’d be great, or even a few buddies. 

13:19

What we do that works well is we have a separate onboarding channel with a few buddies in it and that’s a very safe space for questions. And make sure you tell them when you onboard. I mean that first you know, first meeting at the tech setup. There are no silly questions, because remember how it feels to be you, all the questions going around your head. What do I do now? Where do I find things? Who do I ask? If I ask do they think they shouldn’t have hired me? You know, remove that worry for them. So the best onboarding is paced, it’s not crammed, and this is really applicable for small businesses or big businesses. You know, give them space for them to try things, reflect on things, ask, get feedback, because you don’t want them just to start work, you want them to feel they belong in your team. And it all comes back to building that structure. You know, clear systems take pressure off the department heads and even founders so that you know the founders don’t have to be the go-to memory bank for everything and how it works. 

Danny Gavin Host

14:20

So what’s a common myth about remote team management that you think needs to be re-examined? 

Sarah Cuesta Guest

14:25

The myth, I would say, is that it’s more freedom and less management is needed. So the reality is it needs a different management, not less management. It’s a very subtle difference there, because without the same physical space, where you haven’t got the team within the same physical space, people mainly miss the, the team within the same physical space. People mainly miss the non-verbal signals and they mainly miss mood that they would maybe automatically pick up if they were all in the same break room having lunch. So unless someone’s very confident or very outspoken, you can miss a lot, and if people don’t have context, they fill in the blanks themselves. They either worry about things or they kind of have a bit of self-doubt going on, and in the past I’ve heard team members say hey, my manager hasn’t given me feedback in months. I don’t know how they think I’m doing. Or people are worried about you know, if I do ask questions, I’m just bothering people, aren’t I? I don’t think I should do that. And then you get the opposite end where I’m online all day and they’re really worried about it, but I still feel behind, and so that’s not really freedom. It’s people who are quietly second guessing everything. 

15:33

So the best remote teams have kind of like a rhythm. They’re not rigid, they have check-ins, they have space for feedback and managers who show up really because the best managers are visible, they don’t hover, they don’t wait for one-to-ones or problems to pop up. You know, when they have messages with their team they’re adding context, they’re thoughtful in comments no-transcript and they really do set the tone by how they speak, not just what they’re saying. So you know culture. It shows up in all the little moments every day, how we handle stress, how we share credit, how you handle something when it goes wrong. And so remote teams really do need leadership. They don’t need less of it, they just need better leadership. 

Danny Gavin Host

16:16

And I honestly think that’s human nature right. Where people in one hand feel like freedom means totally free, but more often than not we see this with teenagers a lot, but when we live with certain guidelines and rules, that actually frees us more because we know where the boundaries are and it makes us feel more safe. So what you’re saying I truly believe and I think that it makes sense to apply that to the workplace as well. 

Sarah Cuesta Guest

16:40

Absolutely. 

Danny Gavin Host

16:41

Have you seen a moment where great people management directly led to business results, and what did that look like? 

Sarah Cuesta Guest

16:46

We had a third party communications issue and the third party was between us and the client and the way they communicated was, let’s just say, it wasn’t aligned with our values on communication. 

16:57

So what ended up happening was there was a lot of tension with the team, there was a lot of emotional strain on the team and what really stood out was how you handled it. You didn’t absorb it quietly, you didn’t just keep the peace to protect the revenue that’s a very important point but you did face it, you know, and you had what actually turned out to be a tough conversation and ultimately you walked away and what that did was it sent a message that our values are not lip service, because you took the financial hit to protect our team and there was an immediate impact felt by that by the team. You know they felt protected, you know they re-engaged and that goes a long way something like that to building long-term trust and real staying power. So you can see, you know that investment in people and for anybody you know watching or listening to this, that investment in time as a manager to your team, it has such a positive ripple effect and you don’t know how far it’s going to spread. 

Danny Gavin Host

17:52

So you’ve been at Optage for quite a couple of years now. What are some lessons that you’ve learned specifically working with the Optage team? 

Sarah Cuesta Guest

17:59

I think that you the lesson I’ve learned is you don’t need a massive team to build a strong, values-driven culture, because what really matters is the intention behind everything. So the team here really cares about what they do and they share their knowledge. So you don’t get the silo effect that you know you actually get the wins of the team being noticed, which is lovely, and if someone needs help, you know it actually get the wins of the team being noticed, which is lovely. And if someone needs help, you know it gets offered and encouragement is part of the rhythm that they genuinely support each other. It doesn’t matter which department they happen to be in, and it’s very much a solution mindset, not a blame game. Something will happen because things do and you think, okay, well, how do we fix it? And that energy comes from the top. So I think what I’ve most learned is that you know the culture. This is what gets reinforced daily, and when the leadership shows up consistently with care, then the team mirrors it and culture becomes embedded. 

Danny Gavin Host

18:56

Along those lines. We talk about our core values a lot Stewardship, mentorship, communication and excellence. How have these principles shown up in your work with Optage? 

Sarah Cuesta Guest

19:04

It’s definitely shown up in my work and I try to be really mindful and you’ll laugh because I have a scrappy little post-it note here that I actually have in front of me because it kind of keeps it top of mind. Stewardship I think of as really looking through the long-term lens. So how is the team doing, not just now, but how is it doing over time? And this is where the human comes in, because you know the spidey senses you can feel as something’s off. So I’ll check in and you can suggest small shifts to you know the people involved and then that gets a little positive ripple effect. Later on, if you notice someone’s quieter than usual in a one-to-one or just in a meeting, you know you can circle back to them and just quietly and just help surface what the issue is and give them coaching or find a solution, whatever it is, really to help them get back on track. So that’s stewardship. We’ve got next mentorship. This is really guiding people’s growth. So instead of just thinking, well, I’m going to fix it in the moment. You think longer term. So where do you want to go? Ask the person you know, help them map out those incremental steps so they can have a bit of a stretch, gradually, and keep on growing, because that’s really important, because it keeps everybody’s interest and happiness, you know, to actually stretch a little bit and to learn and reflect and go further. 

20:23

So, and then communication. I suppose this would be my favorite one, because communication for me, yeah, I mean it’s all about tone and trust, isn’t it? And you’ll laugh at me for this, but I am a fan of the audio message within slack. Um, I do do a lot of written messages, honestly, but I am a fan of the audio message because you can convey more energy behind the word. So the written word, you know, sometimes it can be misread, it can be perceived as a bit cold if you just, you know, if you’re quickly, quickly reading, and if someone hasn’t got the right word choice, it can, you know, completely skew a meaning. So my aim is always for people to feel heard and understood. So that’s, that’s my excuse for using it. 

Danny Gavin Host

21:07

And honestly, sarah, I was just thinking about earlier about the concept of, you know, just writing when it’s constructive criticism or even questioning. It’s like, man, I need to. You know, I’m like thinking about myself, but I think it’s a really good point. Like maybe I myself should incorporate voice messages more often, because, especially when it’s coming from like the top of the org, sometimes something that’s like a basic question could be kind of you know, oh my gosh, she’s questioning me, but if I, if I, use voice messages and be able to control that tone, that could be really helpful. So that’s a really great reminder, thank you. 

Sarah Cuesta Guest

21:39

Yeah, a hundred percent, because it will convey really what you’re thinking about it. People will pick up very fast on it because you know we’re effectively we’re all. If you think of our brains and how we work. We are wired to pick up the nonverbal, so when you hear it, that’s one of the main senses and you can tell a lot by tonality. I’ve brought you over to the audio DM side, which is great. 

Danny Gavin Host

21:59

No, it’s fine. 

Sarah Cuesta Guest

22:04

What have you got left? Excellence? Well, excellence is always in the little details. It’s always in the little things. So, following through, say, on a point someone mentioned, it could be someone wants a recommendation for something, or you help them answer something, help the word, something, you know the little details that help people feel supported without really shouting about it. You don’t have to be loud and proud and say it in a thread with other people. You know, just do what the person needs. For our team as a whole, I would say our core values aren’t just words on a wall. They really are part of the team’s muscle memory now, which is a lovely thing. 

Danny Gavin Host

22:36

It is and you know, it took a little bit of time to get those together. We at one point we didn’t have any core values. Then it was like, okay, we need them, so let’s figure it out. And then we had like five or six and then, but slowly, we were able to figure out, okay, what’s really really important to us and I feel like at this point we’ve got these are really good markers to show, like, what the culture is, what we expect, and, yeah, overall I’ve been, I’m really proud of them. If you’re in a team, not leading one, what would you recommend to help that team work better together? 

Sarah Cuesta Guest

23:04

I think the main thing is that you don’t need a title to make a difference. You can lead from wherever you are. What matters most. So what matters most is being clear. Know what your own role is, what are the expectations of you, ask your teammates about their expectations and really don’t assume. Ask and I think also a real strong thing for me is be kind, assume good intent, be the person who shares context. You know, speak up, but speak up kindly. 

23:37

If something feels off with a colleague, you know offer them help, and the energy of being genuinely curious is really key. So sort of you know, zoom out when you hear something and ask yourself you know, what am I not seeing? Yet Step back and wonder, you know, what else could be true here. Don’t just go with you know your initial assumptions, but channel your inner Ted Lasso, be curious, not judgmental One of my favorite TV shows and you’re more likely to find a way forward with someone. Because you don’t need a manager title, you don’t need a team lead title. You really shape culture yourself for how you show up every day. It’s all about your contribution. 

Danny Gavin Host

24:16

All right, it’s time for our lightning round. So I am going to mention a topic and you let me know what comes to mind okay okay, all right. So what’s your favorite book or a book that you’re reading now that you’d like to share? 

Sarah Cuesta Guest

24:28

I think the one I want to share is the fearless organization. It’s by an author called Amy Edmondson. It’s all about psychological safety and it shows really why psychological safety isn’t just about being nice. It’s what lets teams speak up and solve problems and really become high-performing, adaptable teams. So that’s a really good read. 

Danny Gavin Host

24:50

And did someone recommend that to you, or did you just find it yourself? 

Sarah Cuesta Guest

24:53

I have a little app where I read books and it was one of those you might like. Lovely, so yeah. 

Danny Gavin Host

25:00

So that’s where AI does work well. It does Absolutely Cool All so yeah, so that’s where AI does work well. It does Absolutely Cool All right TV show. 

Sarah Cuesta Guest

25:07

Well, I’ve given you a hint, ted Lasso. It shows what leadership looks like when you care about people and performance. And, of course, it is set in Britain, so it’s a win-win. 

Danny Gavin Host

25:15

Lovely, and I think you and I have also spoken about Silo in the past. 

Sarah Cuesta Guest

25:18

Right, yes, Another season coming back to that. 

Danny Gavin Host

25:23

That’d be interesting. I can’t wait. Yeah, all right, and then favorite meal or restaurant. 

Sarah Cuesta Guest

25:28

Well, I am a real foodie, so I would say my meal would have to involve cheese. So my favorites are manchego or English cheddar, of course, and it would have to be on a nice crispy olive and fig cracker. 

Danny Gavin Host

25:41

Ooh, that sounds really good yeah. 

Sarah Cuesta Guest

25:44

Pavlovian responses. I’m saying that now. 

Danny Gavin Host

25:47

So, sarah, what is your next big project? I know recently you got your SHRM certification, which is so cool. What’s next on the docket for you? 

Sarah Cuesta Guest

25:54

I’m going to be putting time into deepening my expertise, so really focusing on performance management, because it’s a common challenge for most teams. You know, any team that’s growing and also pursuing coaching training, some more advanced coaching training to really better support the leaders I work with, because for me it’s about you know staying sharp and being genuinely useful to the teams I work with. 

Danny Gavin Host

26:13

Where can listeners learn more about you and your business? 

Sarah Cuesta Guest

26:15

You can find me at my website, which is thrivetasticbusinesscom, or you can find me on LinkedIn under Sarah Quester Dawson. So if anything here sparked a thought, I’d love to connect because I’m always happy to keep the conversation going. 

Danny Gavin Host

26:28

You know, tara, I was just thinking that I think since you’ve joined Optage, any of like our key main players none of them have left. You know I don’t want to, you know, put anything in my mouth, but really you’re such an essential part of our organization and the fact of having someone it’s kind of like the glue that sticks it all together. I don’t know if you’ve ever thought of yourself that way, but that’s kind of how I think about it, but just sort of the person who’s making sure that everyone’s okay, because you really need that in a remote organization. So thank you very much for everything you do here, and I think today’s episode was absolutely lovely. It gives information about Optage, but also even more than that, just for other people who are running remote organizations what are the things that they should focus on and what they need to do to be successful? 

Sarah Cuesta Guest

27:16

And thank you that means the world coming from you and also thank you for today. It’s been a pleasure. 

Danny Gavin Host

27:20

Well, thank you, listeners, for tuning into the Digital Marketing Mentor. We’ll speak with you next time. Thank you for listening to the Digital Marketing Mentor podcast. Be sure to check us out online at thedmmentorcom and at thedmmentor on Instagram, and don’t forget to subscribe on Apple Podcasts, spotify or wherever you listen to your podcasts for more marketing mentor magic. See you next time. 

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