My Boss 's Boss Assigns Me Work-- Help!! (Ask Christa S7E80)
We're back!! After a short hiatus (life gets busy for all of us, me too!!) Thank you for your patience!!! Summary In this episode, Christa answers a listener question about how to handle it when a senior leader assigns work directly, bypassing the listener’s immediate manager. The episode explains why this can create confusion around priorities and reporting lines, how to respond in the moment without sounding difficult, and how to loop in the direct manager in a way that protects relat...
We're back!! After a short hiatus (life gets busy for all of us, me too!!) Thank you for your patience!!!
Summary
In this episode, Christa answers a listener question about how to handle it when a senior leader assigns work directly, bypassing the listener’s immediate manager. The episode explains why this can create confusion around priorities and reporting lines, how to respond in the moment without sounding difficult, and how to loop in the direct manager in a way that protects relationships, transparency, and workflow.
Key Takeaways
· A skip-level assignment may be well-intended, but it can still create confusion around priorities, accountability, and communication.
· The first response should be calm, appreciative, and clarifying: what is needed, by when, and how urgent it is compared with current work.
· Looping in your manager is not tattling or being difficult; it is how you prevent surprises and keep priorities aligned.
· If it becomes a pattern, address the workflow directly with your boss and ask for a simple process for handling future senior-leader requests.
Additional Resources
The Management Center. “How to Manage Skip-Level Relationships.” September 13, 2021. https://www.managementcenter.org/resources/how-to-manage-skip-level-relationships/.
Lena Reinhard. “Skip-Level Meetings: Common Pitfalls And How to Avoid Them.” March 12, 2024. https://www.lenareinhard.com/articles/skip-level-meetings-one-to-ones-common-pitfalls-how-to-avoid-tips.
Forbes Coaches Council. “20 Tips To ‘Manage Up’ And Build Strong Relationships With Leadership.” June 24, 2025. https://www.forbes.com/councils/forbescoachescouncil/2025/06/24/20-tips-to-manage-up-and-build-strong-relationships-with-leadership/.
Music licensed through Soundstripe: Codes: D9ZUC3H3SR5LIYTI, DHTESRZHAKJ9GH8U, ZYMVOKNKZH5QIQ5M, PRBHHYDGGH6CTPN6, IWRFKTIQNZISTZC
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00:00 - Introduction
00:47 - Listener Question
01:22 - Personality, Politics, or Both?
02:57 - The Direct Route
04:37 - A Process for Boss (or Boss’s Boss) Defensiveness
08:16 - Additional Resources
09:05 - Wrap Up & Submitting Your Question
Transcript
Introduction
Hi everyone, and welcome to Ask Christa! I’m Christa Dhimo, and my show is a free resource to help people get through common day to day issues at work or simply ask a business question they may be curious about. I do this to provide support to those in need, but you know how it helps to like and subscribe, and I thank you for the support.
Now for today’s episode:
This is episode 80 in Season SEVEN, which continues our focus on Dealing with Bad Bosses. Remember: all my episodes offer additional resources, too, so check them out in the show notes.
Today’s episode is about dealing with your boss’s bad boss and what to do when they go over your boss’s head and assign you work directly. This might not be a bad situation all the time, but… it could become a prickly situation quickly depending on who your boss—or your boss’s boss—is.
Listener Question
Here’s the listener question, “My boss’s boss has started coming directly to me and assigning me work. Sometimes it’s a quick request, but sometimes it’s a bigger project or something that changes what I thought my priorities were for the week. I don’t want to say no to someone that senior, and honestly I’m glad they trust me and that I’m on their radar. But they’re going around my boss, and then I’m the one stuck trying to figure out whether to tell my boss, ask permission, reprioritize, or just get it done. I don’t want to create drama, but I also don’t want my manager to think I’m hiding things or ignoring their priorities. What do I do?”
Personality or Politics or Both?
Wooo, this is a stressful situation, especially the longer it goes on. It’s got office politics written all over it, and although I’m not sure of the leveling of these roles, I am sure about one thing: our listener is thinking about this in the right way. You’re asking how you can assure this is a positive and constructive situation, while recognizing that—or at least it SEEMS that—your boss isn’t properly in the loop regarding the work their boss is assigning to you.
There are a lot of things that might be happening here. Maybe things are moving fast at your organization, and a lot of people see you as highly capable and “the one to go to” for specific work. Maybe the boss’s boss assumes your boss already knows of this work, or prefers to go directly to the person they believe can do it (you). Or maybe they’ve talked to your boss about this and your boss gave the OK then never told YOU..
Now obviously if this is occasional, then a simple loop-in to your boss may be enough. But if it becomes a pattern, you’ll want a conversation with your manager about how it may impact or affect your priorities and goals.
And depending on the culture or how your boss and their boss get along, or even how YOU and your boss get along, this could get messy fast.
Still, you and your manager own your priorities, your capacity, your performance, and the context for why certain work matters now versus later. So when someone above them assigns work directly, I urge you to see the risk as less about loyalty and politics, and more about clarity and whether you end up in a two-boss system with fuzzy goals, boundaries, and dueling performance metrics.
The Direct Route
So what do you do when your boss’s boss is regularly giving you what seems like clandestine work?
If you can, always take the direct route with direct, honest communication. Give everyone the benefit of the doubt, and focus on alignment: you want everyone to be on the same page to avoid or at least reduce confusion on priorities or potential risk to your workload. After all, it's not just about who's who, it's also about the practical aspect of your capacity if you have, more or less, two bosses.
Talk to your manager first: “Hi manager, I setup time with you today to gain clarity about how the work your boss has asked me to do fits into the bigger picture of my goals. You know I’m willing to contribute to the success of our organization, and at first I thought the requests were one-offs. They’ve become a regular part of my work, though, and I want to be sure we’re on the same page, especially given the other work items I have on my plate, which remain my priority.”
That puts all the focus on the work while reiterating that your priorities are with your boss.
At the same time, when your boss’s boss approaches you with the next task, you can say, “Yes, absolutely I’ll look into that. I have an upcoming meeting with my manager and we’ll be discussing some of my workload and priorities, and I’ll be sure to include this so I know how to best shift my work.”
Now I say all this in the context of an open, honest, direct environment where your boss and their boss get along—or at least share a mutual respect for each other. I recognize that might not be the case for everyone, so here’s a different approach.
A Process for Boss (or Boss’s Boss) Defensiveness
If your boss or your boss’s boss display defensive behavior, such as your boss asking why they weren’t aware of this sooner or your boss’s boss asking why you have to go to your manager at all, focus more on establishing a process than communication pathways. This will also work if you learn along the way that you’ve become a wishbone with either one pulling you to be THEIR resource—and remember: you are technically your boss’s resource, not your boss’s boss’s resource. It’s not like… the transitive property of equality where you report to your boss and your boss reports to THEIR boss, therefore YOU report to THEIR boss.
It might sound like this: “Hi Manager, lately your Boss has been coming directly to me with new assignments. I’m happy to contribute, and I appreciate being tapped on where I have specialized skills, but I also want to be sure I’m not accidentally creating priority confusion or leaving you out of the loop. How would you like me to handle those requests when they come up?”
You see what I did there? I didn’t talk about the work, and I didn’t talk about the behavior related to the boss’s boss assigning work, at least, that wasn't my focus. Instead, I focused on the process, and I empowered the manager to offer the first response and idea to what the process might look like. There’s a lot of good to this approach, and you’ll receive a lot of information based on the discussion that takes place.
Maybe your manager says, “Oh right—yes, I had that on our list of topics to discuss. I agreed to get you involved with some of that work because of your background and your development plan. Just loop me in if you become concerned about workload, and preferably BEFORE you agree to doing something that overloads you.”
Or your manager might say, “no problem, just copy me when you agree to an assignment in case I’m asked about it, and I’ll trust you to keep our priorities appropriately paced and completed.”
Or, if your manager is savvy about workload, you might hear, “OK, accept anything that will take up to two hours with a completion date of a few days, but come to me with anything bigger than that, or if you’re asked to move your other priorities aside to complete a new task from my boss in a short amount of time.”
And, depending on dynamics and your manager’s style, you may even hear, “send all requests to me first and I’ll decide.” But… wow… if you hear that, especially if you’ve been in the workforce for longer than a few years, it might also be the time to determine whether that control style and approach will work for you. And maybe it will, but the more experienced you become, the less tolerance you’ll have for a gate-keeping style like that. (but that’s for a different episode ;) )
Also to note, you may hear a wonderfully supportive process from your boss, but see or experience embarrassment or the hurt from being excluded as their boss goes around them to assign you work. Depending on the dynamics, that could be a terribly disrespectful feeling, and your manager may need to process some of that in front of you—which only deepens the feels. Pay attention and offer grace and support. This is when you say something like, “I’m really glad we can talk openly about this, because my primary concern and focus is on my work within our team, meeting or exceeding my goals, and assuring we’re all in a position for success.” That might sound like a bunch of mumbo-jumbo, so select the phrasing that is best for you—my point is more about reassuring your manager that you are bringing this to their attention to work through a process, not to exploit any unfairness or undermining behavior from THEIR manager.
Additional Resources
For your resources, located in the show notes, I’m including The Management Center’s article, “How to Manage Skip-Level Relationships.” It’s written more for leaders, but that’s exactly why it’s helpful: it shows how easily skip-level communication can help or undermine managers depending on how expectations are handled.
I’m also including Lena Reinhard’s article on skip-level meeting pitfalls, which includes useful points about unclear expectations, power differences, and unintentionally undermining line managers.
And finally, I’m including a Forbes Coaches Council article on managing up and building stronger relationships with leadership, because this situation is exactly where managing up skills help you stay useful without becoming invisible, overcommitted, or caught in the middle.
Wrap Up & Submitting Your Question
And that’s a wrap for Episode 80 in season seven focused on Dealing with Bad Bosses. Like and subscribe here, but also go to my site and send in YOUR question. It’s AskChrista.com, that’s Christa with a C-H. You’ll also see answers to other questions, listed by category and season, and every season has a theme. As always, thank you for your support. And remember, if you have a business challenge or a workplace issue—Ask Christa!
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