Leveraging Leadership

Q&A: How to Guide Leaders Without Telling Them How to Do Their Jobs

• Jessa Estenzo • Season 1 • Episode 236

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Lisa D. asks how to guide leaders to their next step without telling them how to do their job. Emily suggests agreeing on the project’s end goal, asking questions like “what’s a fair and reasonable way to start?” and having departments explain their preferred starting points. She shares tips for using data and prompts like discussing pros and cons, so all voices are heard.


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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:

00:54 Setting the Project Goal
01:24 Fair and Reasonable Approaches
02:40 Measuring Progress
03:23 Addressing Department Preferences
04:58 Conclusion and Call to Action

emily-sander_2_11-17-2025_122514:

We have a listener question from Lisa d out of Denver, and she says, can you discuss how to guide your leaders to the next step without telling them how to do their job? I work with different departments, and one example is how we want to start a project. One department is picking a starting point based on their preference, and I was picking a starting point based on data. Okay, Lisa, thank you so much for this question. This, uh, this one made me laugh when I first read it, so appreciate that and I'm sure a whole bunch of other listeners will appreciate this as well. The first thing I would say is, let's agree on the goal. So what are we trying to get to? Why are we doing this project in the first place? One way to ask that is, what do we want to be different by the end of the project than at the beginning of the project? So once you can get an agreement or consensus on, okay, here's the objective, here's the end goal, here's the result we want for. Ourselves for our team, for our customers. That can be the stake in the ground that you drive everything toward, that you point everything toward. So getting that agreement on the end goal, um, then asking questions around, okay, given the end goal, we all agree on this, what would be a fair and reasonable way to get there? What are some fair and reasonable options for us all to get there? To get us to that end point. Most people want to be perceived as fair and reasonable. Like people don't go outta their way to like, I'm being unfair. I'm being unreasonable. So couching it with what's the, what are some fair and reasonable ways we can get to that, or what's a fair and reasonable way we can start to approach this Gets people most of the time to calm down and kind of settle into like, okay, okay, we have a defined objective. We're all working together on this. You can even say things like this in the prompter in your question, or just how you. Talk about this. So, okay. So, you know, it sounds like we're all clear and we all want this, this end goal, right? Um, okay. So as we think about this together, and we know that all the departments are gonna need to be involved and it's gonna have to positively impact all departments at the end, what is a fair and reasonable way for us to start thinking about this? Something like that where you just kind of bring it back to where you want it to be To your point about the, the data, I think having a decision based on data and being informed and looking at all the relevant data is spot on. So two thumbs up there. Um, what is a fair and reasonable way to measure progress? So, hey, we're gonna talk about this project that might be long-term and we're gonna have to make sure we're headed in the right direction as we go along. What's a fair and reasonable way to measure progress toward our end goal? And just that question can, can. Reverse engineer you into like, okay, we, we can't just do it by this one department's way.'cause that's not a fair and reasonable way to measure the entire progress for this whole project. That's, that doesn't make sense. So you, without, without even saying like, Hey buddy, we're not gonna do it your way just because that's your department. what's the most accurate way to measure progress toward this overall goal? Something like that would be a good way to start that out. Now if this one department is really hell bent on like this, this, this is the starting point, this is how we have to start, you might ask them like, why is that a starting point? Or why would that be your preferred starting point? Um, it could also be what's important about that as a starting point or what, what makes you. Choose that as a starting point. The reason I switch from why to what is sometimes why questions can make people a little bit defensive. Like, why are you doing that? Whereas, what could be just, you know, tell me a little bit more about what has you thinking about that or what makes that the best starting point in your opinion. Something like that. It could also be, um, if you're trying to like shake loose the, this one starting point based on this one department, it could be. Okay. I hear that you wanna start there. What are some pros and cons to that starting point? it could be something like. What do we get from starting there? Like what do we get from starting at that starting point type of thing where just you just make them articulate their reasoning behind it. Now in that process you could hear like, oh, like actually I assume this, but they're actually talking about it this way, which kind of does make sense. Maybe not all the way, but if we take a portion of what they said and marry that with the data I have, I think we can get to a really good answer. So just kind of jostling loose and getting, um, peeling the onion behind the, the reason why they're wanting to start. At that starting point. So hopefully those are some good prompts and some tactical and practical pieces you can use to, um, guide leaders to their next step without telling them how to do their job. When sometimes it's super tempting to just say, do it this way, do it this way now, it will be better. But Lisa, thank you so much for sending in your question and I hope this helps. I know a whole bunch of other people have scenarios like this, so, um, super helpful to have on the episode. Really appreciate that. And feel free to send me a note on how this goes.'cause now I'm interested If you are listening to this and have a question you want answered on an episode, then feel free to find me on LinkedIn and DM me to drop something in the comments. Then I'll pick that up or to email me directly at emily@nextlevel.coach. Otherwise, I will catch you next week. I'll leveraging leadership.