Leveraging Leadership

How New Chiefs of Staff Can Build Ongoing Relationships with Leadership Teams

Jessa Estenzo Season 1 Episode 272

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0:00 | 11:03

Tips for keeping conversations going as Chief of Staff, like following up after a listening tour and spotting ways to help teammates. Examples include offering to QA an automated process or noticing patterns such as a lack of people management experience, then coordinating training. Early on, it's important to follow up on small things, even if they're only a big deal to one person.


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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 Why Listening Tours Matter

00:58 Setting Up Intro Meetings

01:59 Avoid One and Done Chats

03:21 Research Then Reconnect

04:50 Turn Insights Into Initiatives

07:19 Right Size Your Follow Ups

09:40 When to Relaunch the Role

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. All right, here's a little trick, let's call it, for how to keep the conversation going as chief of staff. So I get a lot of chiefs of staff who are coming into the role. Either they've been hired ex from, an external company and they're brand new to everything, or they've been internally promoted into the chief of staff role and they're brand new to the role. Maybe they've met with or interacted with or worked closely with. They're now peers in a different capacity and maybe some of their new colleagues and peers are brand new, so they're doing that whole thing. In either case, what usually happens, or what should happen is you take a listening tour and this tour can be very. Short or long, depending on the executive team size, the senior leadership size, who is appropriate to speak with, at what juncture, et cetera, et cetera. But most chiefs of staff would do well to meet with everyone, obviously their principal, but everyone else as well. On the ELT, on the senior management team. And if, um, if time allows, then any skip levels to managers and, rank and file folks as well. So you do the listening tour, most people are gonna say yes to the, Hey, I'm the new chief of staff. I wanted to reach out and just connect and hear, you know, what you and your team are doing. What's working well, what's not all that good stuff? Most people are gonna be like, oh yeah, yeah, yeah, totally. Let's go. You know, grab, grab coffee or grab, half an hour or grab an hour, or whatever it is. Most people say yes to the first one, no problem. Everyone gets it, and no one's gonna be like, no, I don't, I'm not gonna talk to the new chief of staff.'cause then it's like, well, the guy didn't talk to me. So once that happens, the key is to keep that conversation going so it's not just a one and done. It's not just a one, check the box, and now we're moving on. I don't really have to deal with the chief of staff anymore. I, I, I talked to, I talked to her and I, and I told her all this stuff about my team having the active listening and the, the angle and slant of how do I keep this conversation going. So here's what I mean by that. Let's say someone says, you know, yeah, I mean, my team is like heads down. Working on trying to automate this process, and it's been a pain in the neck. We actually had to like, we had to redo it twice already. So like, I'm like telling the team, take the fricking time to get this thing right. And as they describe what they're doing, you go, oh, I know a way I could help QA that automated process. And you're like, oh, okay. And maybe you mention that and say, Hey, like I, I, if I had a way to, to make sure you had this right this third time, would that be helpful? Uh, yeah, if you could make sure, but we, we don't know how to No, no, no. There's a way to do it. You do it like this, this, and this. Oh, I didn't, oh, I didn't even know about that tool. I didn't even know about that method. Okay. Yeah. I mean, if you, like, if you have time, if you wanna like spot check our stuff. Yeah, of course. Yeah. We take that. Then you have a touch point in the future. Sometimes you don't tell them and you go, oh wait, I think. I think I have a way to do that, but I don't wanna say anything. I don't wanna like overcommit, but I think, let me, let me take a note. And my takeaway for myself is to go look into that thing like, yes, yes, yes. I verified I can do that. And then just do it and pass them the results and say, here, I thought this might help. happy to jump on another call, type of thing. And at least that continues the conversation there. So there's one example. There's, there's dozens, there's hundreds of things. Little, little things you can listen for of, Hey, would it make sense to follow up on that if it's like, oh. That's an interesting question. Um, let me, like, do you mind if I do some research and like we come back and just like 15 minutes, like boom, like quick, quick direct call. It doesn't even have to be on Zoom or whatever, anything like that. It could be after you're done with your listening to, or you go, holy cow, I see a pattern. I see a trend. we've got 80 people in this company and no one has people management experience. And so all these issues and personnel issues are cropping up. No wonder like, like I can see this. Okay, so then you have a very, uh. Strong basis for, an initiative that you should push, which is, hey, we need to get some people management training and some crash courses and some resources and some different things to supplement this.'cause this thing's gonna fall apart if you're getting to that breaking point of having so many people with no. With no individuals who have managed teams and managed people before. So it could be okay, you talk to the principal, you go, Hey, this is kind of like Defcon one. We've got a situation here. I wanna get in front of this. Here's my proposal, here's my solutions. Principal's like, oh yeah, like we've been feeling that and like I'm a founder, I'm a visionary, but I've never managed people, so I'm learning on the fly as best I can too. Chief of staff goes, no problem. I got you. I got you. ELTI got you managers. Uh, let's put this thing together. So a training program that rollout that announcement and communication and the training itself, or the facilitation of the training itself or the sequencing. Maybe it's you doing the training, maybe it's you finding a resource to come in and do the training, and you take point on coordinating that with the whatever party you're doing that with. All of that is ample fodder for follow up conversations. So. As you go into, I would, you know, say for any of your conversations in that first month or so, but especially like that very first one on the official listening tour. I would listen for things that you can help with. For things that you can detect a pattern from. Oh, I'm hearing this from like seven out of eight people. This is definitely a thing. Or at at least it's a thing on people's minds. or like just little tiny things where it's like, I can make your life easier. I can kind of, you know, there's nothing I can do with that, but I just recognize that you and your team lead are going through a tough time, like it's going through a tough patch. What you need right now is for people not to put stuff on your calendar. So I'm not gonna put anything on your calendar until, three weeks out when this thing is done. But then I'm gonna put a reminder on my calendar to follow up with you and see how things went, see how things are going, and see if it was stood up the way you wanted it to, and all those things. So that could be a follow up as well. But I would carry on. That conversation. So, um, and I would, I would also, most of the time you could do this. Sometimes it's tricky, but most of the time you can make that a positive thing. Right? So you don't wanna be like, bum Bubu chief of staff is gonna follow up with me. Okay? Okay. I have the, I have the follow up call. It's gonna be painful, it's gonna be, difficult, it's gonna be complex. Hopefully you can steer those things towards the positive. And that's the golden path where it's like, hey. I already add something of value, even if it's small and I'm setting a follow up. That makes sense. It's not manufactured. It's not like, oh, like I can't really say no to you, but I don't really wanna follow up'cause that's not really an important thing. Make sure it's like, no, no, no. Like yeah, of course. I would love to follow up with you on that. Make it super positive. Make it super relevant. Um, and then I would say also, if you're new to the chief of staff role, the threshold. Of things you follow up on is different than if you've been in the role for 2, 3, 5, 6 years. And what I mean by that is maybe if you're. In the role for five, six years, and you have a sense of what's high priority and what's low priority, what moves the needle, what doesn't, you maybe have been there longer than most other team members, so you're the senior team member by, by title, by tenure, by all those things. That's a different. Outlook and different ballgame than when you first get into the role. So whereas five, six years down the line, you might not follow up on something like that. Like, hey, they can deal with that. I kind of know what that is, or I kind of know, I don't need to know what that is or, uh, I'm interested in that, but I have so many other things that need attention. Those take precedence. It might be in your first 30 days, your first 90 days, six months, what have you. One, you might not know those things. So it's like, hmm, I don't. I don't know if that's important or I don't know what that is. I don't know if that's important. I don't know if that is, let me go find out, so you take the time to follow up with someone and find out, you know, C you know, I could sit with, can I sit with your team lead and just like literally reverse shadow? I won't say anything. Can I listen to the client calls? I won't say anything. No pressure, whatever. I'm not here to judge people, but that could be the follow up as well. Okay. That might be very useful and very relevant for you at the beginning, whereas, you know, down the line it's like, I don't, I don't need to sit on that call or like, I don't need to go down that rabbit hole. I know what's down there and that's all you. But my point is it might be smaller things at the beginning then. What she would pay attention to later on. And you know, I, I use the word like less interesting or less important. Like they're all important and hopefully you could take my point with this, but they're just kind of your threshold for this. Like, no, I actually am gonna follow up on that. Like, oh, that is an opportunity I'm gonna, like, anything is kind of an opportunity to, that's a big deal to them. Doesn't sound like the biggest deal of companywide, but that's a big deal to them. So that's a good follow up opportunity. I'm gonna take that now. Whereas later on down the line, I might not follow up in quite the same way. So anyway, look for those types of opportunities to keep the conversation going. And this is especially important for new chiefs of staff or people coming into a new chief of staff role. It can be also used when it can also be used when you are kind of. Resetting or revisiting or relaunching the chief of staff role. If it's like, Hey, I was kind of chief of staff version one for the first 18, 24 months, and now something has happened, maybe a merger acquisition, maybe a reorg, maybe, um, the principal left and now there's a new principal. May, you know, all these different things can happen where, oh, this is a catalyst moment. This before was different. Now after this event, things are this new way. It might be a good time to level set on the role then and again, have the listening tour, have the level set, and then have the ongoing conversations. Alright, hopefully you've got something to take away for today, this week, this month for your chief of staff role and those conversations you have with the principal and with your ELT. 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.