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Writer's pictureAnna Conrad

Strategies for Making a Lasting Impression on Senior Leadership



When it comes to advancing your career and enhancing your influence, managing up doesn't stop with your immediate boss. Establishing relationships with senior leaders, including your boss's boss, is critical to career growth. However, these opportunities don't come often; when they do, they require careful navigation.


Establishing relationships with senior leaders, including your boss's boss, is critical to career growth

So, how do you ensure that your next meeting with your boss's boss counts? Follow these tips for insight into how to manage these high-stakes conversations effectively.


The 70/30 Rule: A Strategic Framework

An effective approach to these interactions is to apply the 70/30 rule: speak 30% of the time and listen to the other 70%. This rule is particularly useful in managing up as it allows you to absorb as much strategic thinking and vision as possible while subtly positioning yourself as a thought partner.


This rule also shows respect for the hierarchy. Senior leaders often juggle many responsibilities, and giving them space to express their thoughts demonstrates that you value their time and perspective. But the key lies in using your 30% of speaking time. Instead of making it about what you've accomplished, focus on questions that reflect strategic thinking.



Crafting the Right Questions

Asking the right questions during your limited speaking time can help you stand out as a forward-thinking employee. It's not about small talk—this is your chance to show your grasp of the larger organizational vision. Here are a few expanded examples to help you get started:


What do you believe are the most significant challenges our team should be addressing?

This question shows that you're thinking beyond day-to-day operations. It opens the door to understanding the more significant pressures facing the organization. Their answer might give you insight into hidden priorities or internal politics you weren't aware of. For instance, maybe the biggest challenge isn't just hitting quarterly targets but adapting to a more significant industry shift. The more you know, the more value you can add.


Given the company's long-term strategy, how do you envision our team's role evolving?

This question demonstrates your understanding that your team is part of a larger ecosystem within the company. Their response can clarify where leadership wants the company to go and how your role can contribute to that vision. In fact, studies show that employees who align their work with organizational goals are 42% more likely to be engaged. Understanding the company's long-term strategy is crucial as it helps you see the bigger picture and align your work with its direction.


Based on your observations, how can I grow better to support our immediate team and the larger organization?

Asking for personal feedback shows humility and a willingness to grow. It also opens the door for mentorship. Most senior leaders are eager to invest in high-potential employees who desire to learn and improve.


What trends or changes in the market should we be paying attention to or learning from?

Leaders often have access to broader market research and competitive intelligence that may not trickle down to the rest of the team. Understanding these trends can help you anticipate your department's next moves and proactively adjust your work. For example, if the industry is trending toward AI-driven solutions, knowing this could allow you to suggest ways your team might integrate that into upcoming projects.


When you envision our company in five or ten years, what key milestones do you hope we've achieved?

Visionary questions like this one encourage long-term thinking and help you understand leadership's aspirations. The more you can align your work with those milestones, the more indispensable you become.


Given the challenges our industry faces, what keeps you hopeful?

This question offers a moment of human connection, crucial when building relationships. It invites your boss's boss to share personal reflections, creating a deeper bond and giving you insight into their mindset during challenging times.



The Power of Listening

Listening attentively during these conversations is just as important—if not more so—than asking intelligent questions. Why? Because when you listen, you pick up on subtle nuances and organizational dynamics that aren't always obvious. Pay attention to not only what is said but how it's said. Non-verbal cues, such as changes in tone or pauses before answering, can give you additional layers of insight. This act of respect can significantly strengthen your relationship with senior leaders.

When you listen, you pick up on subtle nuances and organizational dynamics that aren't always obvious.

Moreover, leaders are more likely to see you as a trusted ally when they feel heard. Listening is an act of respect that can significantly strengthen your relationship with senior leaders.


Building Long-Term Influence

Your goal in meetings with higher-ups shouldn't be to impress them with flashy accomplishments but to establish yourself as a thoughtful, strategic contributor. By understanding their priorities and aligning yourself with them, you're planting seeds for long-term influence. After all, career success isn't just about doing your job well—it's about becoming indispensable to the organization's future.


A 2022 Gallup study on employee engagement found that workers who feel heard by their leadership are 23% more likely to stay with the company and contribute to long-term goals. This statistic underscores the value of using these rare opportunities to position yourself as an employee and a critical partner in the organization's growth.



Preparation is Key

Preparation is the linchpin of any successful meeting with your boss's boss. Before the conversation, do your homework. Study the company's strategic goals, review the latest industry trends, and consider how your team's work fits the bigger picture. This will allow you to ask sharper questions and provide more thoughtful input when needed.



Ultimately, these meetings allow you to demonstrate your potential, align your career path with the company's direction, and build relationships with influential leaders. Treat them as such, and you'll get the most out of the meeting and your career.


By applying these strategies, you'll maximize every meeting with your boss's boss, leaving a lasting impression and establishing yourself as a strategic, insightful contributor to the organization's success.


 

👉🏽Do you want more real-life leadership tips? Sign up for the Monday Morning Mentoring YouTube channel and the ILS monthly newsletter. Also, follow me on LinkedIn.

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