Why Bringing Half-Baked Ideas to Your Boss Can Make You a Better Leader

Emily Sander explains why bringing “half baked” work to your boss - especially when you're new in a Chief of Staff role - can save time, spark valuable conversations, and help you calibrate quickly to your boss’s preferences. She gives real examples, like saving hours by checking in early, learning what your boss fixates on, and understanding the order they want detailed information presented. The episode encourages trying iterative updates instead of holding out for perfection.

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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 Half-Baked Idea: Why It's Beneficial

02:30 The Importance of Calibration Sessions

06:36 Understanding Your Boss's Fixations

10:43 Iterative Processes for Long-Term Success

11:12 Encouragement and Conclusion

12:29 Sponsor Message: Next Level Coaching

Transcript

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.

The Importance of Calibration Sessions

Understanding Your Boss's Fixations

Iterative Processes for Long-Term Success

Encouragement and Conclusion

Sponsor Message: Next Level Coaching

emily-sander_1_01-20-2026_104948 0:25

Here is why bringing something half baked to your boss is a good idea. Most people go, oh, wait, no, no, no. I want things to be all the way done before I bring them to my boss. I want the answer. I want the solution. I want things pitch perfect, and then I will present them to my boss. And I say, bring stuff half baked to your boss, especially when you're new to the role. If you're a new chief of staff, maybe it's a brand new principal you've never known before, you've never worked at this company before. Bring stuff half baked to that boss. Here's why I say this. Here's why I think this is a good thing. Number one, it can save you a crap ton of time. And by crap ton I do mean shit ton. So what happens is if you go, I'm gonna spend all this time doing this thing to completion, and you're making guesses along the way'cause you're new to the role and your boss is new and you go, unk, I've spent my evenings and weekends and every waking minute in between calls doing this thing and now it's done. You're gonna be super impressed. The boss goes, oh, no, no, I was thinking more of that, that and that. Not this, this and this. Ha, wait, no, no, no, no, no. Like you want, you wanted this, this, and this. I know in my heart that I wanted this, this, and this. And that's what I thought. You thought, I thought you wanted No, no, no, no. Ask them first. Check in with them first. It could be instead of not this, this, and this, that, that, and that. It could be, oh wait, I wanted this, but like. Nine-tenths of what you did, I actually didn't need. So, so sorry you did that, but you did that on your own volition. So honestly, sorry. Not sorry. It could be, um, oh, you know, now that I see that thing, now that I actually like see, end product. Hmm. I'm changing my mind or that's making me think of something else, or, Ooh. We should get some more input from these stakeholders over here. Now that I see it, now that I'm not just saying it as an idea, as in a concept, as a request out to someone. Now that I see it, I, it makes me think of something else. So you save yourself time by doing an iteration, by doing an iterative process versus babu. Here's the whole thing. All done. Second reason is because you have a chance for questions. You have a chance for a little bit of back and forth, little bit of conversation and dialogue. This is money, this is gold. Even if you get like a short amount of time to do this, it's well worth it. So here's what I mean. It might be, here's my initial thoughts on this. Here's my initial outline. Here's my initial draft on whatever the request was. Um, or here's my, like, I've kind of spoken to a few people here and there. Here's the general consensus. It might be a verbal rollout. It might be, um, a bullet point outline. It might be like a draft of a presentation. Depends what it is. And. Then you could get questions, you could get, uh, clarifying questions, follow up questions. What about this questions? Now that I see that I'm thinking of this, this, and this questions, and you're basically calibrating, you get a calibration round here. Super important. If you're new to a role and you have a new boss. You want to build in those calibration sessions whenever possible. I'm not saying don't do anything and just like have a calibrate, like try to fathom a calibration session, bring them something, do some thinking around this, but then check in with them and this can be really good because sometimes you learn something new where you're like, oh, she thinks about it like that. Huh? I've never thought about it like that, but that's a really good way to think about that. All right. That's really good to know. I'm gonna clock that. I'm gonna keep that in my back of my head from now on. It could be, um. Okay. That might be new to me. It might be a cool concept for me just as a person, but, oh, it's really good for me to know that she is asking about these two things. Okay. She asked, she, she was very quick too. She like asked about one two. What about one, two? Okay. I've gotta. Cover off on that. And that's something you can validate as you go on, right? So if you, here's the first request. Here's my first iteration. Okay? We go through that. Here's the second request. here's a third request. Like, these things are all happening. Um, maybe in, maybe in sequence, maybe in parallel. But she always asks about those two things, okay? I hear her talking to other people. She always asks about those two things. Cover off on those two things. First, always preempt her two questions around that. Good to know. Good to know. You're calibrating. So, okay. You've got these questions are, oh, new perspective. Good for me as a business professional. Good for me as a person. Oh, she always seems to ask those two things. Whenever I bring something to her, I'm gonna have those two things covered off on. Got it. Got it. Okay. Another reason why this is good questions are good Is because sometimes getting someone to articulate their thoughts out loud is good for them. So it could be good for you as well. Like, like, tell me why you want that, or tell me why you don't want that in there, or tell me why, like, you clearly have an aversion to that way of doing things. Like why, like what, what's the motivation behind that? What's the reasoning behind that? Uh, sometimes I, I don't like that. I, I don't like that. Okay. Sometimes that's the answer where certain people, certain bosses, good to know by the way. And sometimes if you just gently invite them or push them. To articulate. Well, can you tell me a little bit more about that? I'm new. I'm new. I'm just, just trying to, you know, figure things out here and you like go, oh, like, it's just, I just don't like it. It's like, um, it's like I want it more to be like an umbrella statement and then it's kind of, we focus in and zoom in from there and then we get to the super granular detail at the very end. Oh. Okay. Totally makes sense. Super helpful if you want it that way. I can tell why putting the granular detail at the very first slide is frustrating and not what you want. Got it. Super helpful. But you're getting them to articulate that and maybe they go, oh, actually like, oh yeah. Actually I should tell more people that because that's how my brain think. I always like the general concept and then one layer in from that, the next layer in from that. Then way more detail than super de than granular detail. That's how I want things presented. That's good for them to articulate to themselves and then hopefully to other people around the company, or even if they can articulate that again, you can articulate that to other team members to better help the principal in the end. Okay. Third reason why it's good to bring your boss something half baked. so sometimes people get fixated on one little thing and they won't let it go, and it's like, but, but, but all this other stuff. We said all this other stuff, and they're like, Z. Like this one thing and it's like, whoa, whoa, whoa. You're getting fixated on that. I don't know what's happening, dude, but like that your face is getting a little red and like consternated, what's what's happening? Some leaders, some people get fixated on certain things. Sometimes it's valid, sometimes it's not. If it's valid, again, learn that calibrate cool. Like you're learning a new role, learning a new boss, learning a new situation, whatever. If it's like, whoa, that seems to be a you thing. That seems to be a personal, like youth, I don't know why you're fixated on that, but it literally has nothing to do with anything that we're doing that's been said that you've said is the point of this that other team members have brought to the table. It seems kind of weird, like it, this seems all about like this is more of a youth thing than an actual thing. Thing. You've gotta be able to distill those and sometimes. Again, it's a calibration. So it might take you a few rounds where it's like, oh my gosh, okay. It's super important. So like, I'm gonna fixate on that, on that thing too. And then you go, oh wait, like we didn't actually need to do that when it was all said and done. Good learning, good feedback. Loop for yourself. Okay, cool. So you do that a few rounds was like, uh, they seem to be fixated on that. Again, I'm gonna. Deep dive again'cause they're the boss and I'm new and I'm calibrating, but ugh, it wasn't worth it again. Like we didn't need to do that. They didn't need to do that again. And then you might change your tactic if even in the first round you're like, whoa. That's super weird. I don't think we need to do that to that degree. You might go, okay, I'm gonna do like a quarter of what they're asking for. They want me to like deep dive in this whole rabbit hole, pull all these reports, do research that's gonna take months and months and months. We don't really need that. That's not in the point of this thing. Maybe they got burned on a question around this before, but we're not gonna get it like that again. so maybe you go, let me address this, let me. Put like one cycle of research to this. Let me put something in the next version of my slide deck, towards that and see what happens. Oh, oh, and they're fine. Okay. I address that. Like, yep. We check that box. We kind of like, uh, assuage that fear. Cool. We're off the races. If they like fixate on it, dig their heels in and deep dive again. Okay. Like good calibration. Okay, what do they need here? Da da da. Another calibration round. Sometimes, here's what I, here's what I've seen. Um, sometimes you get to a point, maybe you're not so new in the role, maybe you're getting to know your boss more. Sometimes people fixate on weird stuff and it's for no other reason than they kind of fixate on it. And if you know that about your principal, you go, okay, I need them to get this out of their system early. I need them to get this out of their system upstream. Not at the all hands call, not at the board meeting, not in a media interview. I need them to do that with me, so I'm gonna create this space in the first two rounds. They always have to go through that. It's just their thing. It's just their thing. They're getting better. They're trying to do it. They can intellectually work their way out of it, but emotionally, they always fixate on this thing. Let me hold that space, build it into the process so they can get it out early. With me in a contained safe space. And then when they go out to other people and other more important, not more important, but other stakeholders that are important, then they don't look silly by fixating on this thing. So anyway, I bring up that third one'cause I've just seen that with. I've seen that as chief of staff. I've seen that with, other chiefs of staff and their principals. And I've also just seen it with humans. Like I do it, like my friends do it, my colleagues do it. some people just have weird things. And if you're in a certain position where that weird fixation can like display itself more than other types of roles, then you have to manage that sometimes. So I just wanted to throw that out there, And that's another reason why bringing things in an iterative process to your boss can be a really, really, really good idea. And it's like you're helping yourself by doing that, but you're also helping them. And you're helping them in the near term and you're also helping them in the long term.'cause you're gonna learn. Them. You're gonna learn this process and what needs to happen in this process for you, for them, for the team, for other stakeholders. And you're gonna be able to, build this system for your principal and build this system and process as chief of staff to be the best it can be. So anyway. I would highly encourage you, especially if you're a new chief of staff, especially if you don't know your principal well, but even if you've been in the chief of staff role for a while, even if you have a pretty good handle on your principal, it's not a bad idea to do things in an iterative process. They. Ask a request of you, they send you to spearhead, a project they ask you to do. Um, you know, we need to reorg this part of the business, or we need to look, be acquisitive in this part of the market, in this part of the industry. we need to launch a new product that does this. I saw a competitor. We have to launch a new product. Do this. If you get any kind of like, we gotta do this. I have an idea, I have a concept, I have like maybe a thing. Bring back. Here's my initial thoughts. I spoke with a team and here's our general consensus. here's an outline of what I put together. Here's some, cursory research I've done. Is this directionally correct? What do you wanna know more about? What do you not care about? those types of things. So I would highly encourage you to just do this in an iterative process, Against the common sentiment, bring something to your boss. Half-baked when you feel like, uh, it's not what I normally wanna be doing. I strive for excellence and I strive for perfection and all these things. It might be like, it might be something where you feel like I'm bringing something half-baked to my boss. Good. Do it. Try it. Let me know what happens, and I'll catch you next week on leveraging leadership.

12:32

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.