Leveraging Leadership

Shifting the Mindset: When Chiefs of Staff Move from Asking to Informing

• Emily Sander • Season 1 • Episode 178

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This episode breaks down how a Chief of Staff should shift from always asking permission to confidently informing others about next steps. Emily shares real examples, like updating a principal before or after launching a new workflow, and explains why this approach helps the executive team and boosts the Chief of Staff’s own confidence. The episode ends with the reminder that it’s all about finding the right balance between asking and informing.


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Who Am I?

If we haven’t yet 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:

01:42 Mastering the Principal-Chief of Staff Relationship
06:01 Empowering the Executive Team
08:24 Balancing Asking and Informing: The Art of Leadership

emily-sander_1_04-08-2025_104028:

There's a critical inflection point that every good chief of staff goes through. It is when you go from asking permission to informing. I see a lot of chiefs of staff, especially new chiefs of staff who get into a new role and maybe it's their first time being chief of staff and for the first 30, 60, sometimes 90 days, they're kind of hanging back and saying, let me get the lay of the land here. Let me figure out who's who in the zoo. Internal politics dynamics, systems and tools, external customers, all these things. And that is all well and fine and certainly smart to a certain extent. But I see a lot of people get stuck in the, I'm just gonna hold still. I'm not gonna try to rock the boat. And sometimes they go. I'm only like, I've emailed my principal and they haven't responded, so I'm just waiting and then, and then after a while I follow up and then I just wait. And then I follow up one more time and I just hold still and don't do anything. So there comes this point where a transition, it's almost a mental mindset piece where you go, I'm not gonna default to asking permission. I'm gonna default to moving and going and progressing, and then I'm going to inform the appropriate parties at the appropriate times. So. Here's what this could look like. Let's talk about the chief of staff and principal relationship. So instead of asking permission waiting. Following up and waiting. It might be you say, okay, I know enough about what's going on here. I think I know what we need to do as a team. Or at the very least I know which group of people need to get together and talk about what to do. And that's a big part of a Chief of staff's job as well. And it could be, okay, I'm going to inform my principal that I'm going to take these next steps. I'm not asking to do that. I'm informing them so they're aware that I'm going to take these next steps. And most of the time principals will go, okay, thank you. And if they have a big problem with it, they can stop you If they have a big problem, like, oh, hold on. Actually, I, I'm sorry I didn't tell you. I actually have a meeting with those same people over here. I'll include you in that invite. Or actually, hey. You actually don't know about this thing yet, but there's this whole like dynamic and this whole other m and a piece in play that might change that. Let's hold off on that until next week. Okay, got it. No problem. So you inform them ahead of what you're doing, but then you go do the thing. It's not an ask, it's an inform. Another way you can inform is after the fact. So let's say you're like, okay, I kind of know what needs to happen here. Let me get the game together and then make that thing happen, and now it's done. So let's say we have a new process and flow in place. Maybe it's a handoff from the sales team to the delivery teams. Okay. CEO Principal probably doesn't need to be involved in the minutia of that. Maybe if the CEO slash founder is involved in enterprise sales, they would, but let's just say this is larger company or a different situation where they don't need to be bogged down in the minutiae. Part of why they got a chief of staff is to lift them out of the day-to-day stuff. And you just take that on. So it might be, okay, I see what needs to happen here. I see the players. Let's get a huddle in place. Let's get a game plan. Let's run this game plan for a bit. Okay, let's make some tweaks to it.'cause the handoff didn't quite work the first one or two times. Now we've got it. Okay, now we've got this thing streamlined. It's repeatable, it's done. We are more efficient, we have happier customers. And then you inform the principal, Hey. Me and the team, we've stood up this new process. It runs better. Just FYI kind of a glancing blow type of thing. That's another way to inform. Okay. So we've got principal, chief of staff informing before something happens and then after something happens and one thing off this as well is I see a lot of chiefs of staff who have come in and founder has brought them in to lift them out of the daily operations. And so they might not know how to lift out yet, but they've brought in a chief of staff to, Hey, I know I need to lift out and I know that I am kind of used to being involved in things and I can't anymore, and I have to go off and do these other things. And so chief of staff, please come in and do this. If a chief of staff defaults for too long of asking and deferring and always having the CEO founder essentially make the decision and essentially like almost do their jobs for them, you are not doing your job. You're not doing what you were brought in to do and you're not helping your principal lift out. That's the whole point. So sometimes you have to push the envelope and say, okay, I'm gonna make sometimes myself and the principal a little uncomfortable by going and being proactive and saying, I have this. I'm taking this, I'm taking care of this. I'm taking care of this for you so you don't have to worry about this. You go off and do other things and kind of get them in their area of strength and where they need to be. So you've gotta lift the principle out, and sometimes it's one of those things where they know they have to do it. But they have habits built up where they try to deep dive in the organization, and part of informing them is it's not a ask to you, I'm just informing you, I'm gonna go do this. And sometimes we gotta push them outside of their comfort zone. But what I've found is, it's kind of funny, is most of the time they've brought in a chief of staff because deep down inside. They know they need to lift out. They need you to lift out. I sound like Jack Nicholson in that movie, A Few Good Men, you want me on that wall? You need me on that wall? The principals know they need the chief of staff to lift out, and they secretly want you to just inform them to take stuff off their plate, to give them no excuses, not to lift out and do other things. So that's part of your job as Chief of staff. Okay. We've talked about the principle. Let's talk about why going from asking permission to informing is good for the executive team. So a lot of times when a chief of staff goes in there, everyone's like, Who is this? what is a chief of staff? Especially if the executive team, maybe their founding members of the company have never had a chief of staff before? And this is a very reasonable question. Hey, like you are close to the CEO. We're used to being close to the CEO. You have chief in your name, we have chief in our name. Like, what's happening here? How are we gonna operate? Totally valid question. Part of what you do is you front, run that with messaging, hopefully, ideally from the principal and then from yourself, and then you show them. You show them how you're going to interact, and in the beginning it makes sense to ask questions, to get input, to figure out how we do things today and why we might have done those things. Historically, your job as chief of staff is to take that to the next level, the next phase of the company to move it forward, not be handcuffed to the past and like, oh, we've done it this way to date. That's how we always have to do these things. We're gonna move it forward. But asking and getting the backdrop and background information. Totally, totally makes sense. Having a good relationship with people all across the board is an advantage and totally makes sense. And then it comes to the point where, hey, I was brought into do this job and part of my job is to get this. Team collectively to the next level. And sometimes that means I'm not gonna ask you. Sometimes that means I'm going to inform you that this is happening. Now, you don't have to be an ass about it, but you can inform people this is what's going to happen. And even while you're doing that, you can ask for their input as you're going along. And that's often a good combination. Again, people like this because they like to understand the rules. Basically, they like to understand the rules of engagement. A lot of people like to understand, if you wanna call it like the pecking order or the hierarchy or how things are gonna work. You've gotta set that tone early. So if you're talking about a 90 day. Span, you gotta have a foundation. Let that set. So it's kinda like pouring concrete is where like, okay, you have a little bit of time to move stuff around to get it where you want it to be, and then it sets and that it's really hard to move again. So you wanna set that foundation in a way where, look, certainly for the first little bit here I'm gonna ask, but then over time I'm gonna move more to informing. So it helps set that relationship and set that foundation with the executive team. The last thing I'd say here is going from asking to informing is really, really helpful. Not only for your principal, not only for your executive team, but for yourself. For yourself as chief of staff to know with evidence that, oh, I can move things forward. I can. Not always ask for permission. I can sometimes ask for forgiveness if I've gone too far and that's a perfectly fine and often great thing to do, right? So you wanna be pushing the envelope and pushing things forward and almost pulling some of the team through their comfort zone, but knowing that you can do that. Knowing that you have the authority, the influence, the capability, the persuasion, the communication skills to do that, and you have the knowledge and knowhow across the company. I can see these things moving. I can see across the board, I can see all these dots being connected across silos. The fact that you can do that, I think I've seen that give so much confidence to chiefs of staff when they're like, Emily, I went in there and I told them this was happening. Then it happened and like people were like, okay, I guess that's what's happening. It's like, yes. So it's, it's the competence, confidence loop happening in these different areas and you get a few of those under your belt and again, your principal sees what's up. Okay. She takes care of it. Your executive team sees what's up. Okay. I guess that's how I interact with him. You see what's up, we're like, okay, I guess that's how I'm gonna be chief of staff now. And it's awesome, by the way. So it's a good thing for the principal, for your executive team and for your own self and for your own perspective and view of yourself as chief of staff. Last thing I'll leave you with, is it moving from always asking questions and always asking permission to always informing to always telling people how it's gonna be. No. No, it's a mix. It's both. And so a chief of staff has to have like a, a mix of these. What's an analogy? Like a blend of these, like a constellation of these. Oh, it's like, it's like a artist's palette, like a little, the little color, like different like red over here and blue over here, and yellow and white. You're kind of like Bob Ross. Okay. You have the palette, you're doing a beautiful painting from scratch, and you have to blend those colors. So sometimes it's red and sometimes it's green, and sometimes you gotta add some white in there for whatever reason, and you're like blending those, the background, and then the foreground comes into play and you're doing different nuances with maybe a different brush and some leaves on the trees or whatever the f. Frick. Bob Ross does. But that's you. You are Bob Ross. Go be Bob Ross. Go be a chief of staff. Sometimes ask and sometimes inform. I'm gonna leave you with that and I will see you next week on leveraging leadership.