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
Practical Ways Leaders Can Release Guilt and Move Forward
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
Emily Sander talks about how Chiefs of Staff often feel guilty or frustrated about things like not working long enough hours or not helping a struggling teammate. She explains that being too empathetic or self-critical can backfire and suggests telling yourself, "and that's okay," to relieve pressure and keep perspective. Real examples include feeling called out for working from home or regretting not helping someone in a team meeting.
Get in touch with Emily:
Feeling the pressure to do more, be more, or fix everything? Book a clarity call w/ Emily here.
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 Common Chief of Staff Struggles
01:04 When Empathy Becomes a Detriment
04:16 The Power of Saying It's Okay
06:17 Mountains Out of Molehills
08:03 Building a Higher Baseline
09:00 Try This Exercise
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.
Common Chief of Staff Struggles
I know a lot of chiefs of staff who feel bad about something. So, "Oh, I'm not working hard enough. I should be working harder on this thing, and we'd get further." Or, "I feel guilty for not helping that person when I saw they were doing a bad job, and I probably could have helped and fixed it and jumped in or did something, and I didn't do it." or I'm angry at someone because they're calling me out for not coming into work, and it freaking doesn't matter if you're in the office for my role. For my role, I can get more done from home. I can work from home. I'm disciplined. I got all the setup, et cetera, et cetera. So but it irks me when, like, this person says stuff. There's dozens of examples.
When Empathy Becomes a Detriment
Those are just to give you a flavor of what I'm talking about, this is sometimes the other edge of being empathetic or having empathy. You wanna care for people. You wanna be observant and in tune with how other people are doing. That's a good, good human skill, also a great chief of staff skill. But like any strength, if it's taken too far, it can become a detriment, and it can actually hurt you or have negative influences on the people you're trying to have a positive influence on if it's taken too far or applied in a not so great way. So we wanna be careful about going into that zone and, like, working on that edge where it's like, ooh, it's not doing what it's supposed to be doing. It's not doing the positive thing it's meant to be doing or that it can do. I speak with a lot of chiefs of staff who feel bad about something. They feel guilty about something. So maybe it's, "Oh my gosh, I should have worked more hours over the weekend because we would have gotten further on that project." It could be, "I feel bad for not jumping in to help that team member when they were flailing on that team call. They were ill-prepared and doing a bad job with their report-out, and I could have jumped in and saved them and fixed it." It might be like, "Ugh, I'm angry. I feel bad. I feel angry because this fricking person is calling me out for not coming into the office five days a week when my role can stay at home three days a week and be just fine, be even more productive. I know my role best, and they're just trying to make a thing about it. Da da da da. So I feel bad about that. I feel angry and frustrated." It could be, "I feel like this person should be doing better with all the managing and coaching and prompting and opportunities and training that I'm giving this person, but they still can't chin the bar. What the heck?" So all of these types of things. There's dozens and dozens more, but these types of things I hear a lot. And Sometimes it's good to sit with those emotions and say, "Okay, what is this telling me? What's the message here?" And a lot of times, for a lot of people, a lot of people listening to this podcast, if you're listening to this podcast and you're the type of person who does that, I would wager that our issue is we are often too hard on ourselves in these scenarios. we're self-critical. We're overly self-critical, and I would say that there's a strength in having empathy for people, in being tuned in to what people are doing and feeling and seeing and hearing and how they're responding to things. All of that is good. All of that is being a good human and a great chief of staff. So definitely don't throw the baby out with the bathwater. I would say any strength that you have, if taken too far or if applied in the wrong way, can be a detriment. It can hurt more than it can help. So even with the best possible trait, characteristic, strength, skills, talents, whatever, if you take it too far or you mis-misapply it, you misplace it, it can, it can turn on you, and so it's a double-edged sword in that sense.
The Power of Saying It's Okay
And I think this is what happens sometimes when we go, "I feel," let's talk about guilty. I just had someone the other day, "I feel so guilty, Emily. I always feel guilty about this or that or the other thing, and I don't want to. I don't like it, and I just... I always feel like I could be doing more, or I should have done this, or I have to fix that for that person." And what I often suggest to people is to alleviate the initial, "Argh, I don't like, I don't like that feeling," and then you get mad about yourself for having that feeling, is go, "Here's what I'm thinking and feeling, and that's okay." So, for example, it might be this team member is really calling me out about this work from home thing in front of other people. This doesn't need to be in front of other people. I don't think it needs to be in front of other people, and they're still calling me out, and that's okay. and that happens sometimes, You know, I should have... Oh my gosh, I saw her flailing in that team thing, and we were doing the round robins, and man, like I knew the answers. I knew what she was supposed to do, and I could have jumped in and saved her, and I didn't, and now I feel bad about it. Yeah. You know, sometimes people aren't gonna have the greatest answers, and I could jump in, but I don't, and that's okay. That's gonna happen sometimes. In business, that's just- that's gonna happen sometimes. So you can apply these to almost anything you do, but it, it relieves some of the tension and pressure. Like, oh, okay, maybe it is okay. Maybe it is a little more okay than I originally thought. Even that little pressure valve release. Even that little bit of space you can create for yourself can be hugely beneficial. It lets you take a breath, like okay. 'Cause we get short of breath, we get clenched up, we get tight, and if you could just, okay, release a little bit, relax the tension a little bit. Let me breathe a little bit. Let me get some oxygen into my brain so I can think better with a clear mind and give myself this room.
Mountains Out of Molehills
And we often make a bigger deal out of things than they are. We've all done this, yes. We've all seen people do it where it's like, "Whoa. Whoa, buddy. Like, you're making a mountain out of a molehill. Let's just calm down. It's not that big a deal." And we can see it from the outside, but when we're in it, when we're in it, right, it can feel so overwhelming and like a fish in water. You can't not be in it. So this just allows us to break out of that for a minute and say, "Oh, yeah. No, no, no. There is a higher level of perspective here. Okay. Yeah. I mean, this stuff, ah, this stuff happens. Sometimes this is gonna happen." Doesn't mean you have to love it, doesn't mean you have to be best friends with w- whatever the thing is. It just means you're seeing it for what it is. You can call it out for what it is, and like, "Yeah, that shit happens sometimes. Not my favorite, but it happens. Gonna move on with my life." Or, "Hey, this, this, and this happened, and, uh, I didn't do that, and that's okay. That's okay. Maybe it was good that I didn't jump in to help the colleague on their flub in the team meeting. Maybe there's positive to that. Maybe, you know, that has ramifications or there's thought processes or conversations that are happening because of that, that are ultimately positive that I'm not aware of." Like, you can make all these what if scenarios in the positive direction. But it's like, yeah, it's like, "It's okay. It's okay. I don't have to be perfect." Dangerous word, by the way. I don't have to fix everything or problem solve everything or save anyone. Those are also a little bit dangerous, can be on the dangerous territory if we misapply those. So that's just a, an interim trick, if you wanna call it that, of adding da, da, da, da, da, da, da. And that's okay, and that's okay. That happens sometimes. That's happening now, and that's okay. And just deescalate yourself and kind of talk yourself down.
Building a Higher Baseline
I often use this as an interim step with my coaching clients while we build up the baseline, meaning we build up, okay, how do we not get into situations where we feel that, uh, that guilt, that like, oh, I should be doing something, or that adrenaline, that bite of adrenaline where it's like, oh my gosh, something horrible is happening. We raise the baseline so the threshold for that is higher, meaning you can't actually rattle me that easily. It's gonna take more to get me out of my, zone here or, or where I wanna be at. So we do those things in parallel, but sometimes when it's so acute and it's so disruptive and it's so distracting and it's so-- takes up so much energy just to, just to deal with this thing, it's okay, is often a good release valve for the interim, and then build up the practice, then build up the habits that are gonna take longer to install and get in place, but have the more sustainable or more holistic
Try This Exercise
effect. So anyway, give that a try. Give that a try for yourself. Maybe pick one thing and be like, "Oh, okay, here's my go-to predominant crutch, like my go-to, I feel guilty about that, or I feel always feel I should be doing more." And then say, "Okay, here's what I normally say to myself, and then I'm gonna remember to say, 'And that's okay,' or, 'And that happens,'" or whatever phrase resonates with you. And then secondarily, maybe think about a person you know, maybe on your team, maybe a family friend or whomever, who's struggling with something like this and offer this to them because this can be the greatest gift you can give to someone. And it will also be interesting to see how they respond and what they pick up on that they're doing and what their go-to release valve phrase is. It just could be an interesting conversation from someone that you know as well. All right. Give that a try. Let me know how it works. Shoot me an email, emily@nextlevel.coach. Drop it in the comments. Find me on LinkedIn. Would be interested in all the different variations that are out there, and I will 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.