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Ali Khan
Co-founder
Ever bump into a leader while grabbing coffee, or found yourself sharing an elevator with the CEO?
It’s not as uncommon as you think! And when that moment comes, having the right questions ready could be a game-changer for your career or business.
Imagine you're armed with questions that not only show you’re informed but also genuinely curious about their journey and insights.
That’s where we come in. Our list is designed not just to impress, but to spark meaningful conversations that could lead to fresh insights and opportunities.
Leadership isn't just about guiding teams and making decisions; it's about constant learning, adapting, and connecting. Whether they're voracious readers, strategic thinkers, or creative problem-solvers, every leader has a unique approach to staying ahead.
What better way to discover their secrets than by asking them directly?
We'll give you our top 10 questions right here at the top and then we'll even give you a way to ask your leader an anonymous question using our platform! (you can also use it to give them anonymous feedback).
Top 10 questions:
There are a lot of questions that can run around your mind when meeting a leader. But despite your willingness to make the most out of your meeting you can easily make the conversation weird and sound rude at some point.
Start easy with small talk, introduce yourself, and ask them questions related to the place or wherever you happen to meet. When the introduction is being made along with other small talk continue to tell him/her about your work.
Tell the leader what you do, be honest, and share what you love and look forward to achieving in your future.
This way you will let the other person know that you are a potential future leader and will make it easier for them to engage in your conversation. Personal drive is infectious, and a leader can tell when someone has it almost immediately.
Ask important questions like the importance of professional development in the workplace. Communication, information exchange, and feedback are valued in specific organizations.
If your workspace utilizes platforms like Slack or Microsoft Teams, you can integrate Wrenly.ai's suggestion box into your channels. This feature allows you to pose questions to your leadership either directly or anonymously.
The option to remain anonymous is particularly valuable, as it empowers you to raise sensitive or challenging questions that you might hesitate to ask openly.
Being able to ask such questions without fear of repercussions can foster a more open and communicative work environment.
Below is an attached screenshot demonstrating how you can use Wrenly to anonymously gather feedback from leaders, enhancing the overall feedback process within your organization.
What are good questions to ask leaders? Here we have listed a few good questions you can ask leaders.
Using Wrenly to ask questions from leaders in your organization can be a straightforward process, especially if your workspace uses Slack or Microsoft Teams.
Here’s how you can set it up and start engaging with your leadership:
This tool can be particularly useful for fostering open communication and ensuring that all team members, regardless of their position or comfort in speaking openly, have a chance to voice their concerns and questions to the leadership.
Wanna test out on your own for Free?
Every person is different therefore every organization or workplace is different from each other. There are endless questions to ask respected leaders.
An organization leader's role is to guide and manage the activities of a team in a broad sense.
Questions to ask organization leaders should reflect the unique dynamics of every team and organization.
From strategic planning to boosting team productivity, understanding the leader's approach to guiding their team towards a common goal can offer valuable lessons.
An organization's leaders focus on both the company and its employees. Some open ended questions you might ask include:
Open-ended questions allow for deeper insights into their management style, decision-making process, and how they foster a culture of growth and innovation.
Corporate leadership extends beyond daily operations, embodying the core values and guiding principles that steer the company's future. It, however, goes beyond only monitoring workers.
They create declarations of basic principles and give orders to staff members at all levels. However, on a more personal level, it promotes team building and employee retention when workers believe that their leader is familiar with them and aware of their own objectives.
Since they are involved in a lot of things at once you might have a lot of questions to ask such leaders too. Here are some of the best questions to ask corporate leaders:
Asking corporate leaders strategic questions can reveal how they inspire engagement, foster employee happiness, and leverage social media for business impact.
When it comes to HR leaders and teams there are a lot of questions they can answer from many aspects of the organization or company.
Since they are considered to be the bridge between the staff and the leading team.
You can ask the leader how they manage to work on their leadership qualities while doing daily work.
To answer this question, they can describe how they personally organize their time in order to incorporate learning. This question focuses on time management, but at a leadership level.
When meeting an HR leader there are some strategic questions you can ask them:
The thing is that there is no bad or good question as long as you keep it professional, simple, and balanced.
Some people prefer to not talk about their work when they are someplace else and that is totally okay.
Also, think about the leader's personality, what kind of person he or she really determines what you can get out of him or her. Focus more on their creative thinking and ideas.
You can learn more about senior leaders' strategic thinking and where they perceive the biggest dangers and possibilities by asking them how they're defining the limits of their company.
Additionally, it can help you identify the ideal attributes to add to your leadership style and provide your team or business with excellent advice. For both employers and the employees they lead, the coach leadership style is one of the most beneficial.
On the other hand, think about yourself, if you have a friendly personality and no problem getting to know other people then that's a good skill to utilize.
Always find the right time and place, or maybe the right time and place will find you, if it does here you have some good questions to ask leaders at work.
The best questions for leaders to ask are those that help them learn about the people who report to them.
These questions will help leaders discover what motivates their employees, and that information can be used to help them stay engaged.
Additionally, and perhaps more importantly, it can help leaders lead better.
Once they know what motivates their employees, they can use that information to motivate and lead their team in a way that not only increases productivity but also makes everyone happier in the process. Let's look at some of the questions that you might have in your mind.
Leaders generally appreciate receiving questions in settings that align with the seriousness of the inquiry. Formal questions may be best suited for scheduled meetings, while more casual or personal questions can be asked in less formal settings. The context can indeed influence their responsiveness and the depth of their answers.
It's advisable to avoid questions that are overly personal, invasive, or irrelevant to the leader's role and expertise. Questions that put the leader in an uncomfortable position or challenge their authority publicly should also be avoided.
To effectively follow up after asking questions, consider expressing gratitude for the leader's insights and showing how their advice has been beneficial to you. Keeping the communication lines open with periodic updates on your progress or further inquiries can help build a lasting professional relationship.
There’s so much more to learn about leadership, so be sure to check out our other resources on the topic! And if you want even more great content about leadership and management, subscribe to our free newsletter! Thanks for reading, and good luck on your own journey to leadership excellence!
It may inspire you to apply the techniques and styles they use in your own leadership efforts once you have gained a better understanding of their leadership styles. If you are headed on the leaders path, taking examples from senior leaders is always a good method. This will make your employee morale much better.
Do you have any good questions in mind? Feel free to share with us your ideas.
