Why “How Can I Help You?” Is a Dangerous Question for Chiefs of Staff

This episode explains why Chiefs of Staff should avoid asking "How can I help you?" and instead focus on what will move the needle for their principal and team. Emily Sander shares real pitfalls, like getting stuck with small admin tasks, and suggests specific strategies such as spotting communication breakdowns or coaching leaders through challenges. The advice includes leading with strategic proposals rather than just picking up tasks others want to hand off.

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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 The Help Question Trap
02:08 Ask Needle Moving Questions
02:45 High Impact Examples
03:59 Know Your Best Service
04:32 Avoid Getting Pigeonholed
05:26 Lead With a Proposal
07:04 Takeaways and Closing

Transcript

The Help Question Trap

Ask Needle Moving Questions

High Impact Examples

Know Your Best Service

Avoid Getting Pigeonholed

Lead With a Proposal

Takeaways and Closing

0:06

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. Here is a common mistake that I want chiefs of staff to avoid. This can be, this can be a fatal flaw if you go down this road. there is a danger in asking the question, what can I help you with? Whoa, whoa, whoa, whoa, whoa. Wait a minute, Emily. Hold on. You've said in previous podcasts that the chief of staff is there in support of their principal and to collaborate with the executive team, and you've even said it's part of the chiefs of staff job at some points to just make the principal's life easier. So like why is, how can I help you? the wrong question. How can I help you? What can I take off your plate? what's a pain point right now? Those types of questions often, not always, but often. go to, uh, I don't wanna do this, can you, if you could take this off, that would be great. If you could take this off my plate, that would be great. What can you help me with? Um, uh, well there's this like big hairy thing that's kind of complex. No, no. Could you just like do this one ticky tack admin thing? Um, what would really help is just like coordinating like the calendars for this, this, and this. Asking, how can I help you? Is almost. Too much of a free for all, for a lot of principals and a lot of executives to handle, because what can help them is like, like, make me feel better and get this stuff that I don't wanna do off my plate. And it could be things where it's like, hey, um, what would really help me out is if you went to have this really difficult conversation with someone that I should be having a conversation with. I'm the CEO. This is a type of conversation where only I can have this, but what would help me out and make my life a lot easier is if you could go do that and I don't have to do that conversation. Here's what you should do instead, zoom out, step back, ask chief of staff. Go, what is gonna move the needle for my principal, for our executive team and the company? What is gonna give us the biggest bang for the buck? What is gonna get us closer to our main goals? You should have. 1, 2, 3 top goals and top objectives for pick an interval in the next six months, the next 12 months, 18 months, three to five year plan, and figuring out, okay, what are the big things I can move or the little things that I can nudge. Maybe I can't move any big things, but what are some little things that I can nudge? it could be. we actually do have like a DEFCON two situation happening with our executive personnel Someone's gotta head that off on the pass. There is part of this that I can do as chief of staff. There is part of a conversation or part of a maneuver that I can do as chief of staff to help alleviate this and to. Help it not get worse. So like, let me go do that.'cause if this thing explodes, we've got larger problems. We've got many more problems to deal with. It could be something like, I need to spend some time with my principal and apply some coach approach to leadership. And they're, they need a little coaching on this. They're getting a little wobbly over here. They're panicking, they're starting to panic. I understand why, but they actually don't need to, they don't need to panic as much as they're starting to panic. Let me, let me just. Get in front of that and talk to them about that. That's all. Let me get one step ahead or, mm. I could see where this is going or where it could go. It could be, Hey, here's this really boring unsexy data migration. Between two tools that no one wants to do. It doesn't fit neatly in any functional area, but if we're gonna do any one of a number things that we wanna do in this next year, we're gonna have to get this data set clean and normalized. so just knowing where. You are best suited and are of best service to your team overall. I think that's a much better lens than, uh, Hey, hey, how can I help you? can I make your life easier? Like, what are some, what are some quick wins? What's some low hanging fruit? Sometimes those questions are okay in the right place when they're used appropriately. but it's not a blanket go-to question. How can I make your life easier? What can I take off your plate? Um, what are some pain points that you're having? Those, those are Very tricky, slippery slope questions. And if you ask them over and over and over again and don't ask any other of the big picture strategic questions, you're gonna get pigeonholed very quickly and, you know, valid. It's valid. If that's all you ask, they're gonna pigeonhole you into like, okay, give her like the, the. Kind of tiny ticky tack minutia stuff. Give her this stuff that I don't wanna handle. Give her this thing that's making this other executive upset. I, I've seen chief of staff after chief of staff just fall down this hole and like, no, no, no, no, no. Boom, boom. They kind of hit their head and like, fall down a fall down a hill. It's like, no, no, no, no, no. It's not. The reason you're, you're down there is because you've asked the wrong question at the top. Like, start with this different. Trajectory, this different lens, this different pathway, and then you won't fall down. You'll kind of move up the hill or whatever. This analogy is breaking down quickly. But anyway, you get my point. You get my point. So don't fall for this trap of a question. as chiefs of staff, we always talk about framing up a decision or having a good prompt or question that kicks off the whole discussion, right? if you go, Hey, um. I've noticed th these folks over here aren't communicating well. Um, they're not communicating well in our executive team meeting, and their teams are not communicating well with our client handoff. And this is gonna cost us, and we're not putting ourselves in good position to do the other things we wanna do later in the year. here's what I propose doing. And barring any objections from you, principal, from you CEO or maybe perhaps the leadership team itself? I'm going to kick these coordination meetings off for the next 45 days. We're gonna a meeting every other week for the next month and a half to just get these things ironed out. The result of those meetings is gonna be greater alignment, so we're gonna have less time. For each team to be working on this, and it's gonna be streamlined so we don't have to do, um, redo work. We're gonna have less redo work. And we're also going to document some standard operating procedures. So new hires on either respective team can have those when they first come in. Something like that is, is to me a different, uh. Tenor and texture and feel, then lemme just make your life easier. So anyway, I think you hopefully have gotten my point here and just, just incorporate, you can incorporate the actual questions and specific examples I've given in this episode. If those are helpful to you, that's fantastic. If not. Take the sentiment and spirit of what I'm saying, into whatever you're doing, into any conversation you're having. Yeah. So, think about, upcoming conversations this week, this month, or when you're going into kind of a meeting or a conversation around, okay. Uh, my workload, my role, the type of work I wanna be doing. A little bit of the perception don't over index on that, but it is part of the game, like the perception of my role. Okay. Those types of things. Just, just keep this in the back of your mind and how can I kick this thing off? How can I frame this thing up that's gonna be meaningful and helpful and significant? For me, yes, but also for my principal. For our team in general and for the company as a whole, and certainly for our customers and other downstream stakeholders. Um, so take this to heart. I've seen this go, I've seen this go very badly and it seems to be a, just a common thread that people keep doing. So I don't want you to be one of those people. it'll save yourself and the people around you. A lot of, a lot of angst and, uh, and just resetting expectations and okay, now I gotta backtrack this whole thing. Just kick it off this way. Kick it off with a different type of question or prompt. Alright, 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.