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How to Have the Perfect Meeting With Your Boss’s Boss

Having a meeting with your boss’s boss—cue the nervous jitters, right? We’ve all been there, palms sweaty as we walk into an office much bigger than our own, hoping our boss’s boss doesn’t relentlessly grill us on our quarterly metrics.

While catching the attention of the bigwigs can feel daunting, arming yourself with some insider tips means you can seize the chance to shine rather than letting nerves get the best of you. Keep reading for proven ways to make the most of mingling with management.

Why You Should Have a Meeting With Your Boss’s Boss

You might be wondering if meeting with the top boss is really worth it. But before you write it off, consider why making an effort could pay off. From gaining valuable insight to opening new doors, spending time with higher-ups has benefits you want to take advantage of. Let’s look at what you stand to gain from face time with the boss’s boss.

Career Development/Advancement

One of the key benefits of sitting down with senior leadership is gaining visibility for your work and ambitions. When you network face-to-face with those higher on the organizational chart, you have the opportunity to brief them directly on your accomplishments, responsibilities, and long-term goals. This helps them get to know you as more than just a name on paperwork. 

Having influential allies who can vouch for your skills and contributions is invaluable when better positions arise. Rather than just seeing another resume, if your superiors upstairs know you as a dedicated employee always looking to expand your impact, they’ll naturally think of you when scouting for potential leaders to fill key roles.

These meetings also allow you to learn about strategies and priorities from management’s perspective. You can gather first-hand insights into where the company is headed, which can guide you in cultivating experience in relation to the company’s future needs. Whether it’s improving certain skill sets or taking on short-term projects, meeting with these bosses can empower your career moves.


In any company, visibility is important for progression. But it’s easy to get overlooked doing your usual work behind the scenes. Meeting higher-ups puts a face to your name and lets them learn more about your contributions directly from the horse’s mouth. 

Having one-on-one meetings with senior leaders raises your profile beyond just another employee. This keeps you on their radar so that you become more than an anonymous resume when opportunities arise. Leadership is more likely to remember—and advocate for—someone they’ve met personally. 

It’s also a chance to showcase your highlights directly to those who influence bigger decisions. This is better than relying on others to tout your achievements. This way, you can promote yourself and discuss your goals and ambitions first-hand.

Problem Resolution

We all hit roadblocks now and then on key projects or initiatives. But sometimes, some issues are too complex for even our direct boss to sort out. That’s where face time with higher-ups comes in handy. 

If you’ve been battling with obstacles that won’t budge through regular channels, an oversight from leadership could be the fresh perspective needed. Laying out complexities personally ensures that leadership fully understands how these hurdles affect your work.

Rather than letting problems linger, taking them higher up the ladder puts more problem-solving minds on the case. You also demonstrate diligence in seeking solutions rather than complaining and leaving the task without a solution.


We all know how important networking is for career growth and organizational success. However, it’s not always easy to connect with senior leaders from other departments due to differences in workflow and responsibilities. Meeting with your boss’s boss gives you a valuable chance to expand your professional network meaningfully.

Man gets the job
Meeting with the top shots allows you to expand your network 

Executives may introduce you to other key stakeholders, partners, or industry leaders they interact with regularly after having a one-on-one with them. With expanded networks come more ears to hear about your innovative ideas, capabilities, and interests, allowing you to showcase your skills and expertise to an audience that could open new doors down the line. You never know which connection may lead to an amazing future opportunity.

Even without explicit introductions, the meeting can present an opportunity for you to build relationships with high-level contacts simply through conversation. These top-floor allies might have knowledge and experiences very different from your normal peers, so tapping into their diverse perspectives and resources can benefit you greatly.

Demonstrating Leadership

Meeting the top boss is a great way to show your leadership abilities. Even everyday tasks look different from the top-down view of executives. 

In these meetings, you have a chance to showcase qualities like confidence, communication skills, and initiative. Because how you present yourself and your ideas reflects your leadership potential.

Good leaders want go-getters who take opportunities into their own hands. Setting up the meeting yourself demonstrates motivation and initiative. And when you bring well-thought-out topics and questions, it shows preparedness. 

Truthfully, planning and executing a successful high-level discussion is no easy feat. Your performance in one of these meetings ultimately helps you highlight your leadership qualities for bigger roles in the future.

Relationship Building

Meeting above your direct supervisor gives you a chance to get to know influencers face-to-face. It shows initiative when you take the time to build rapport with busy executives. 

Conversations help you link on a personal level beyond daily tasks. They start to see you as a person rather than just an employee.

These strong relationships can soon start to unlock doors; such executives remember those they connected with positively. This creates an open line later for advice, opportunities, or help on tough projects. 

You can also pick their brains on their career path and learn from their experiences. Building trust can lead to mentoring that furthers your growth.

How to Have the Perfect Meeting With Your Boss’s Boss

Meeting with the top boss can feel intimidating. But don’t stress – with some easy steps, you’ll impress in no time. The following tips will turn those butterflies to your advantage. 

Prepare for the Meeting

It’s important to do your research before sitting down with the top boss. Learn about their career progression, interests, and priorities for context. You can also look up any of their previous meetings or presentations to understand their style. Knowing all these will help your discussion feel personalized.

Think back on any past interactions you’ve had, even if brief, and jot down anything you discussed and their reactions. Remembering previous conversations shows that you pay attention to details and want to further the relationship.  

Spending some time researching and planning will lay the foundation for a smooth, productive meeting. You must understand the other person and have defined goals that set you up for success. 

Schedule an Appropriate Time and Location

When it comes to finding a time that works, your best bet is to check their online calendar to see if they have one publicly available. That’ll give you a good idea of their availability. 

If not, it’s best to check in with their assistant, as they know their boss’s schedule inside and out. They can tell you what blocks of time are more open versus busy periods you’ll want to avoid.

Also, ask the assistant how far in advance you should request the time. You don’t want it to be so last minute it feels rushed but too far out, and it might fall off their radar. 

As for location, their office is typically the best option since you’re coming to them. But conference rooms can also work well depending on how many people need to attend. 

Just be sure wherever you choose isn’t noisy or distracting from your discussion. The same should apply if it’s a virtual meeting – ensure your setup allows you to focus without interruptions.

Set Clear Goals and Prioritize Topics 

With the background of your boss’s boss in mind, consider what you want to get out of the meeting. Do you need help solving a problem? Want to share an update on a project? Looking to network a bit? It’s good to have a clear goal so you can stay focused.

Then, put together a quick agenda to keep things on track. List the main topics you’ll discuss and rough time estimates. You don’t need to follow it strictly, but it’s a good guide. 

Be sure to share your draft agenda with their assistant in advance for feedback. This allows time for any needed adjustments. Come prepared with your thoughts organized on the day – it shows you respect their time.

Woman paying attention to a presentation
Create a concise agenda with key talking points

Prepare Your Boss

Before the big meeting happens, definitely check in with your direct boss. You don’t want to go over their head by having the meeting without their knowledge. Use the opportunity to get their perspective on the goals and agenda – they may have some useful background knowledge to share.

Also, see if your boss would be willing to introduce you when you meet with their boss. Getting a nice endorsement up front is super helpful. If not, they may have suggestions for how best to establish yourself.

You can also ask your boss about their interactions with top executives and their communication style.

Communication and Presentation

Once you’ve gotten a meeting with your boss’s boss, your communication and presentation matters greatly. When speaking with them, focus on maintaining good eye contact and clear articulation. It shows you’re engaged and confident in what you’re talking about.

Present yourself confidently through your posture, expressions, and tone. But you also want to stay relaxed and open-minded to what they have to say. 

This is why having your key talking points ready helps you efficiently communicate your goals. But also provide chances to discuss as well – conversations work both ways.

And don’t worry if you get asked a question you’re not 100% sure of – simply explain that you’ll follow up if needed. It’s best to focus on having a productive dialogue over being perfect.

Ensure You Listen Actively

Listening is as important as talking in a meeting like this. You must ensure you focus on what they’re saying by avoiding distractions. Some strategies for this include maintaining eye contact, nodding along, and mirroring their body language, which helps show you’re following along.  

You can also restate or summarize what they said in your own words to confirm understanding and ask open questions to learn more about their perspective. Referencing past things they’ve said shows you listened closely and leaves them feeling truly heard.

Woman filling job application in office with boss
Listen attentively and take note of key points.

Identify Potential Issues and Address Concerns

When prepping, think through any concerns or objections they may have given their role. Then, have some well-thought-out responses in your back pocket, just in case.  

Also, consider if parts of your proposal might need tweaking. Being flexible shows you’re committed to finding agreeable solutions together rather than just pushing your own agenda.

And if challenges do come up, remember not to take it personally. Truly hear their perspective so you can find a compromise or see things from a new angle. 

It’s also good to keep an open mind. As someone more senior, they may notice things you didn’t think of that could make your plans even stronger. Collaborating with different views leads to better outcomes.

Follow Up Afterwards

After wrapping up your discussion with your boss’s boss, take notes on any action items or next steps that were agreed upon. It helps to be crystal clear on responsibilities and deadlines.

Also, remember to send a thank you email afterward recapping the key discussion points. You can even attach your meeting notes or materials for easy reference later.

If possible, get started immediately on your tasks, as it shows good initiative. Ensure you regularly update them on your progress to keep accountability high.

And later on, you can ask for feedback as a nice way to check that you’ve still got things on track. Plus, keeping your documentation handy is good if things come up again down the line.

Maintain the Relationship

It’s important to continue nurturing the relationship beyond just this one meeting. You can do this by sending occasional updates on your team’s work.

See if any department events are coming up where inviting them as a guest speaker could be a nice way to maintain that relationship. Also, occasionally, you can loop back with a short email to provide a brief update on your team’s progress and achievements. 

Striking a balance between keeping in touch and respecting their busy schedule leaves a great impression. It may not be obvious initially, but these small gestures can go a long way in maintaining goodwill.


Ultimately, a big meeting like this is all about creating that great first impression and planting seeds for future success. What matters most is showing you’re someone they can rely on to get things done. All you have to do is focus on the important things and keep an open mind.

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