Leveraging Leadership
Leadership is messy. Most advice isn't built for the reality of competing priorities, difficult stakeholders, limited time, and imperfect information.
Leveraging Leadership is a practical leadership podcast for Chiefs of Staff, executives, founders, and senior operators who want to lead more effectively and navigate complexity with confidence.
Hosted by Emily Sander, former Chief of Staff and executive advisor, each episode delivers real-world lessons, practical frameworks, and candid conversations with leaders across business and beyond.
Topics include executive communication, leadership presence, decision-making, delegation, organizational influence, operating rhythms, team effectiveness, and the often-unspoken challenges leaders face behind the scenes.
If you're looking for thoughtful conversations, practical takeaways, and leadership advice you can actually use on Monday morning, you're in the right place.
Leveraging Leadership
Rethinking How Can I Make Your Life Easier in the Chief of Staff Role
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Emily Sander shares feedback from a listener who disagreed with her advice to ask, "How can I make your life easier?" as a new Chief of Staff. The listener argued this question could reduce the role to admin work and distract from driving the team's main objectives. Emily Sander explains her view that the approach can help in some situations, especially early on, but agrees it's important for a Chief of Staff to adapt and stay focused on results.
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Who Am I?
If we haven’t met before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.
Time Stamps:
00:25 Listener Pushback Setup
01:40 Fear of Admin Pigeonhole
03:31 When Empathy Makes Sense
04:53 Mixing Approaches as Chief of Staff
06:36 Drive Objectives Hard
09:23 Adapting by Team and Context
11:29 Feedback Invitation and Wrap
Welcome back to Leveraging Leadership, where we unpack the art of business leadership. I'm your host, Emily Sander, chief of staff to an executive leadership coach. This show is all about finding your points of greatest influence and leveraging them to better serve those around you.
Listener Pushback Setup
emily-sander_2_06-23-2026_131804I recently had a conversation with a listener of this show, and they had reached out to me and said, "Hey, Emily, um, you know, appreciate your podcast, love what you do over at Chief of Staff space, but I disagree with you on something you said in a previous podcast episode." And they outlined what they disagreed with, and it was done in a very, um, cordial, thoughtful way. I get a lot of people going like, "That's bullshit," and blah, blah, blah in the comments. I'm like, whatever. But this person did it in a, in a, in a positive way and really explained their, their thinking and explained their experience about why they were giving that answer. And the piece they disagreed on is in a previous episode, I said, "Ask yourself, how can I make this person's life easier?" And it was said in the context of your principal's life easier or the leadership team and how to make their life easier. And the context for that episode was a new chief of staff. So I was saying, when you're just getting into things and you're learning who's who in the zoo and you're trying to build trust and you're trying to be helpful and explain your role and all that stuff, oftentimes asking like, "How can I make your life easier?" And just get some of those small wins, is what I was talking about, um, asking that question. So what can I do to make your life
Fear of Admin Pigeonhole
emily-sander_2_06-23-2026_131804easier? This individual said, "No, no, no, no, you don't wanna do that because it'll pigeonhole you into ticky-tacky admin stuff. It will, um, basically lower or lessen the value of the chief of staff role in the eyes of your principal and in the ELT members." And this person's main, like, gist of the argument was My job as chief of staff is not to make your life easier. My job is to get the team to meet their objectives. So that, I, I think I'm representing that fairly. Um, by the way, I asked this individual if they wanted to come on a podcast episode and talk about this stuff, and they were politely declined and said, "Podcasts are not my thing, but thank you very much." And, uh, I said, "Can I, can I talk about our discussion?" And they said, "Absolutely. I'd like to remain anonymous, but please, please, uh, bring it up in episode if you want." So anyway, I think that there's a lot of truth in what this individual was saying, and I, I believe in that same episode or in a subsequent episode, I said, "Hey, look, there's a difference between your first 90 days as chief of staff and a year in, two years in, when you have a longer tenure. And you know the players, and you know their tendencies, and you know that when this person asks you to do it, they're kind of pawning off a piece of their job they just don't wanna do, and you're like, 'Bullshit.' I call bullshit on that. I'm not doing that." And I believe, and I think I said this in the, in the episode and I, I'm saying it to you now, I still believe that there are moments when asking how can I make your life easier, and actually just trying to make someone's life easier, is the correct approach. I would say this individual, we went back and forth, and I, I think we got to the point where they were like, "Hey, Emily, are there set plays?
When Empathy Makes Sense
emily-sander_2_06-23-2026_131804Are there set scenarios?" But, like, if you wanna go through all the combinations you can get to, like, yeah, is it like, "Hey, my, my principal just had a shitty week." Like, they got pummeled from stock earnings. They're getting crap from the board. They've got people leaving on, you know, the, this team, and they've got p- you know, vendors complaining about this, um, this thing over here. And is it just like, "Hey, listen dude, like, w- do you need a hug? Do you need, like, your favorite comfort food? Like, what do you need to take the edge off and to make your life easier?" And there's, like, those, like, set kind of moments that that happens in, but this individual was like, "That's not really a default mode I would use. That's certainly not something I would use a lot or even sometimes." It was, it was the rare exception to the rule, the rare exception to the rule, um, to, "Hey, I'm not here to make your life easier. I'm actually here to- get us to meet our overall objective. And, and they were saying that might be, like, hurting your feelings, and that might be making you feel bad, and that might be telling you straight up, like, "Hey, you're bad at your job and you need to do this differently. I'm not trying to make your life easier so you can do a s- you can do a subpar job. I'm trying to make it so our team and company hits our objectives." And I totally take that on board. I totally take that on board, and I appreciated this person saying this, 'cause I, I agree with that. I agree with that.
Mixing Approaches as Chief of Staff
emily-sander_2_06-23-2026_131804I think where we differed a little bit was the, the mix, right? So kind of the mix of, of approaches. They were very much, like, very stringent on the I wanna make your life easier should be used, like, once or twice a year maybe. In my view, that can be used a little bit more. That can be, um, not in a, not in a derogatory, I'm putting myself down way, can I get your lunch, sir, type of way. But like, "Hey man, I'm just gonna go through my roster and think how, like, what's going on in these people's worlds? Um, how can I make their life easier?" Not going out of my way to do their job, or not to Uh, tarnish the chief of staff role or bring that office down in stature, so to speak. But more so in that role, embodying the chief of staff role, if there's something I can do that just makes this person's life easier and it helps their team, and it helps the workflow, and it helps whatever, and I can do that, then I wanna be looking for moments to do that. So that's kind of where I come out on that. There's obviously, obviously differing opinions, and I totally respect people's opinions, but I still think there's a little bit of room. Um, I think there are certainly times when you need to not care how people think and not care if people like you, which is really hard for a lot of people. It's hard for me. It's hard for a lot of people. But this individual I was speaking to was like, "Look, that's just how it goes sometimes, and you just gotta be a bull in a China shop sometimes." And, um, I agree with that. I think the mix of percentage of when you should do it versus not, I think that's where we had the biggest discrepancy.
Drive Objectives Hard
emily-sander_2_06-23-2026_131804I think a lot of chiefs of staff could stand to be more focused on are we going to meet our objectives that we agreed upon. They said, like, let's talk about it and have the, have the group come to consensus. They... This individual talked about that. But it was like, and once we come up with that, we're gonna drive hard to that. That was the sense and sentiment I got from this individual, which I think a lot of teams can stand to use more of, to be honest. I think a lot of teams can stand to use more of that sentiment, more of that drive, more of that like, let's go, like stop. You know, there's soft, there's, uh, safe, there's, uh, cautious, there's feelings, and then there's like, let's go. Let's just freaking go. Those aren't mutually exclusive. Those aren't mutually exclusive, of course, but you know what I'm saying. Like sometimes you just gotta go and be hard-nosed and single-minded about it, and that can serve a lot of teams well. So that's what I really liked about the conversation. I happen to think there's, I happen to think there's a little bit more leeway in how you get the objective achieved. Um, I think there's certain times and maybe phases where like, "Hey, for the next three months we gotta go, like all hands on deck. I don't wanna hear about anything else besides getting this part done." I think there are phases that are like that, and I think there's other phases where it's like, "Hey, let's rest the team. We've just wind sprinted with the team for three months. Now they need some rest to catch their breath, and we can do these other things over here in that period, but this, this phase calls for something else." And I think, in my opinion, a chief of staff needs to have that flexibility and, um, adroitness to adapt. Like, "Hey, this phase calls for this over here. I'm gonna go. I'm gonna say no to these other frivolous things, these distractions. And in this phase it's a little bit different tone and tenor." The other piece that I would say is Sometimes a chief of staff will have to be like, "Let's get it done now over in this side of the business with these groups and these departments." And sometimes they'll have to flex and say, "But for these folks, they just ran a freaking wind sprint. They're h- like dry heaving on the ground, like tr- gasping for air. And so when I'm dealing with this group for this period of time, it's different. When I'm over here, like, let's go. Stop, stop, stop dilly-dallying. Stop talking about that. That's total BS. It's just a distraction. You just wanted to feel comfortable. It's not time for our c- like our blankie. You don't need your blankie right now. You need to get it done. Over here, like, I'm gonna give you a blanket. I'm gonna give you like a, a space blanket, and I'll be the fire, and I'll keep you warm, and like all the stuff and things. You get all the stuff and things." You get what I'm saying, right?
Adapting by Team and Context
emily-sander_2_06-23-2026_131804So it could be, hey, for this phase for the company overall, it requires this approach, and it could even be for this part of the company right now, it requires approach A, and for this other part of the company right now, it requires approach B. So I think having that just, again, ability to adapt and ability to recognize what the team needs and where the chief of staff role can add the most value and where they can, um, sometimes get out of the way, sometimes get in the way, sometimes interject themselves, sometimes defer. You know, I'd love to do that. I really feel like we should, but the team just doesn't need that right now. All these different scenarios come into play, and I think, um, I, I would say, uh, where I differed with this individual the most was just the, um, the breadth and the range that you have as chief of staff. That's what I would say. But again, I think that this person was so focused on getting their team to the objective, and in their specific scenario, I'm, I'm not gonna go in it 'cause, um, it might give away some stuff, and they asked to be anonymous, but in their given situation and their given, um, industry and company and what had just happened with their team, a lot of the single-minded focus on hitting the objective makes sense. So if you're out there going like, "I kinda hear what you're saying, Emily, but w- we're more in the, like, we gotta get this dialed in and get it dialed in now, um, scenario," then you might very well take the approach this individual had of like, "I don't really care about anything else. I don't care about making your life easier. I don't really care about your feelings. I just wanna get it done." Um, and that approach can be useful at times. But just know that in my mind, your You're picking, you're choosing that approach out of many tools in your tool belt. You're saying, "Okay, this one is appropriate right now for this group. And now, this other approach is appropriate right now for this group." And you can apply different ones. That's where I kind of differ
Feedback Invitation and Wrap
emily-sander_2_06-23-2026_131804a little bit. But I want to, uh, I wanted to throw that out there, one, mostly because I love when people have feedback for the conversations and discussions and the points that are brought up in this podcast, whether it's a guest episode or a solo episode. Two, I really appreciated how this person approached writing me. So on LinkedIn, they just wrote me a note. I wrote them a note back. We went back and forth a few times, and then we eventually were like, "Hey, let's just jump on a call." And again, I would've loved to have them on the podcast 'cause they were very, um, they were very articulate, and they were very, uh, they just positioned their argument so well where I was like, "Huh. Hmm. Oh, yeah, I didn't think about that," or, "Oh, well, I guess, you know, in that scenario, no, what I said didn't quite make sense." And they were very good at kind of doing that in a very, uh, uh, collaborative, cordial way, and, uh, that's also, that's also rare these days. So I really appreciated that as well. But if you have any comments or questions or disagreements or like, "Hamely, I'm totally with you on this, this, and this, but on that, I think that you're, I think that you're actually kind of missing the mark over here, and here's why." I really enjoy that kind of back and forth and that kind of feedback, and it just makes me, um, sharper, and it teaches me, and I learn from all these different things that other people are going through. So please feel free to send any of those comments, questions, concerns, disagreements in, um, and I, uh, again, am respecting this person's, uh, request to be anonymous, but just, you know who you are, and, uh, I told you I would send you a link to this episode. And so I hope that I've represented your position well, and I hope that I've represented the, uh, sentiment of our exchanges because I thought that they were just really, um, really fruitful, and I appreciated not only your, your stance but also how you presented it. So thank you very much, and if anyone else who's listening has any kind of comments or feedback, please, please, please feel free to send that in. And, um, otherwise, we'll call this one a wrap, and I'll catch you next week on Leveraging Leadership.
This episode is brought to you by Next Level Coaching. If you or anyone you know would like to learn more about executive leadership coaching, please visit www.next level Coach.