Four Tricks to Leading Up and Giving Feedback to Your Boss

4 min read
May 29, 2022 12:43:00 PM

Giving feedback to your leaders can be a scary thought. You may feel like as a reporting employee, your voice or opinion has less weight. Or you might have noticed an issue that is holding your team back and you need to find a way to bring it up to your boss - but maybe the issue has to do with them. 

Before you start sweating it out thinking of having a conversation like that, know it’s possible to deliver feedback to someone you look up to, who leads you, and who isn’t your equal. The key is two-way communication. 

Leading up is the most difficult part of becoming a leader, but here are four tips to help you learn to give feedback like a boss to anyone - without burning bridges. 

Timing is key.

We’ve all seen a cringy and emotion-driven delivery of “feedback” to someone else at work - it’s exactly the kind of stuff that goes viral. Instead of immediately going to someone with feedback at the moment you think (or feel) it, take some time to write out an action plan - what you want to say, how you want to say it and take time to look at it objectively from all sides. And then plan to prioritize the conversation proactively, instead of reacting to it. Making it an action item on your list for your next one-on-one meeting ensures that you deliver the feedback in a timely manner, but it gives you a buffer of time to nail the delivery.

It’s also way less likely to catch a leader or boss off guard if you bring feedback up during a regular one-on-one where feedback is already a normal rhythm. This will make it more likely they’ll be able to hear what you’re saying and process it without defensiveness.

P.S. if two-way feedback isn’t already a part of a regular rhythm with your leader, here are a few ways to implement that now.

Small Progress, Continuous Growth

Process first.

This is another reason why the one-on-one meeting is so helpful. If you’ve been having these regularly, it should be less likely that something big and terrible has been building up that you need to deliver negative feedback to someone like your manager. But sometimes, big things happen suddenly and need to be addressed.

One way you can practice growth as a leader is by ‘sorting’ your feedback before delivery. Think through what the true issue is - and if it’s rooted in resentment, try to reframe it. Remember, as a part of a team, you want to grow collectively. That means that everyone should be getting feedback frequently - both good and constructive. But growing as a team for the good of the organization and ultimately, better outcomes of your work, also means that not every issue is worth bringing up.

Part of ‘leading up’ is being able to categorize what’s a big enough deal to bring up to a manager, whether it has to do with them specifically or someone else on your team. Thinking like a leader means you approach difficult conversations or challenges with grace for others, patience, and self-awareness. If someone knows that your goal is alignment, team improvement, and resolution without letting personal feelings or outside factors get in the way of the real work of growth, it helps it feel less like an attack, allowing you to mitigate potential outcomes much more efficiently.

Sandwich it in positivity.

This is an old trick, but it’s a simple one. Start the meeting off with

positive feedback. 

- call out something great you have seen this person doing and genuinely tell them. Try to frame something that may be harder to hear in positive brackets. This will help the person see that you’re not criticizing them, but rather you want to share information that will benefit their growth and development - which should be the goal of feedback to begin with.

When the meeting is over, end it with gratitude. Your perspective and focus as a leader should be the longevity and health of the team and the individual person. Sharing that you’re grateful to work and learn with them does a lot to prevent bridges from burning down.

The sandwich method gets mixed reviews, but the mindset around it is what’s critical to capture. Is your goal for delivering feedback moving the needle in employee growth or is it an agenda item to change their habits for reasons that only benefit your individual goals?


eBook: effective one-to-one meetings

Do it in person.

This may be another obvious tip, but with an increase in remote and hybrid work, you may find that most of your communication happens over email or slack. If you have to have a tough conversation, or you’re nervous about sharing, in person (or at least over live video) is always best.

This way, both parties can see and share tone and body language that puts the other at ease. If you’re sharing negative feedback with your boss about someone else, this is also a great way for them to be able to help you triage the issue and determine the importance or severity, rather than trying to read between the lines of a well-crafted email.

Being able to deliver feedback to anyone with outcomes that change actions but don’t damage people starts with relationships: built through a foundation of regular, consistent meetings. If you’ve already built a rapport with your boss or another leader, when the time comes to give feedback of any kind, it happens easily and is delivered with tact and kindness, in a spirit of growth and confidence. 

But not speaking up means the challenge could be stopping you and your teammates from growth or innovation. Challenging the status quo and bringing new ideas to the table is also how you start building a track towards leadership yourself. 

Want to see how Leadr’s team navigates feedback conversations that set people on a track for growth and greater leadership? Request a demo here. 


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