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7 Questions Leaders Avoid Asking Other Leaders, But Shouldn’t!

As a leader, having routine conversations to collect feedback about what you can do to become a better leader can be uncomfortable at times – at least when the person you’re seeking feedback from is either your boss or peer.

The initial reaction is that this feedback conversation will only build ammunition for the unwanted performance review or deadly feedback loop. This reaction is natural because of our human defense system – for anything that doesn’t sound good, we have automatic sensors that trigger deflections to protect the areas where we perceive pain. Feedback can be painful if not provided, viewed, and received the best way.

To remedy this, think of feedback as feedforward. The goal of the information gained from others is to help us to move forward, not backward. In a safe environment, asking thought- provoking questions early on with the right leader can give you leverage to influence what actually will become the narrative of your success stories.

So, what would be the results if you could leverage a feedforword conversation to gain positive insights on things you might do differently today? That is the path great leaders take.

That’s why leaders should ask the following questions to other leaders – and then take action (listed in no particular order):

  1. “What is your new vision for my role?”

A job description is very different from a vision for a particular role or assignment. Many times, leaders I coach will say, “I am doing my job, but people do not seem to be fully satisfied. How can I satisfy them?” Often I find that they are absolutely right. They are performing all of the elements of the job description, but somehow missed the casting call in playing a newly envisioned role their boss or team has defined for them.

Being the Go-To person, Team Leader, Catalyst, Supporter, Visionary, Decision Challenger, Influencer, Advocate, and many others are roles that leaders expect other leaders to play. Often this is not discussed early on, and it sometimes changes. More often than not, the issue arises when a meeting, decision, or outcome is the opposite of the desired one.

Having a transparent conversation about the vision of your role will help you to identify whether you are capable of playing that role; if not, it provides an opportunity to development an action plan to close any gaps.

Without a common vision, leaders perish – no matter how often their roles may change.

  1. “How can we enhance our current working relationship?”

Good leaders are smart. They realize that everything starts and ends with relationships. The degree of your relationship with someone determines if you will stand by them or take a seat when things get tough. This is where leaders rise and fall.

Being confident enough to ask how you can improve the relationship with your boss and peers will give you big kudos. Clearly they will see you as a person who is interested in investing in a mutually beneficial relationship.

Also, if there are areas you need to work on improving, you have a head start over anyone else who hasn’t built up enough courage to ask the tough questions. Having a strong relationship is more critical now than ever before.

The degree of the relationship with other leaders will determine the organization’s job satisfaction levels. Leaders need to feel that their job is more than just a job; it is a relationship entity diagram that expands beyond teams into the customer’s base.

The happiest and most engaged leaders have great relationships. Unfortunately, without those relationships, becoming an extraordinary leader is virtually impossible.

Good leaders plus good relationships equals extraordinary performance.

  1. “What is your biggest frustration or feeling of disconnect in my area of responsibility?”

Every now and then, talent supply produces an extraordinary superstar leader whose functional area of oversight is squeaky clean. But most leaders – even high performers – have areas that need to be cleaned up in their shop once in a while.

In addition, feedback on frustrations and disconnects is often not based on truth, but rather personal assessments which cannot necessarily be supported with fact or data.

Leading with the perceived issue in hand is always better than trying to explain it away.

  1. “What challenges do you and others feel when working with me?”

Unless you are not human, chances are your boss and others likely experience challenges working with you. You may not be aware of it because they have not come right out and blatantly told you, or perhaps because most people never ask the question. Think about it this way, if our family members, spouses, significant others and/or friends have challenges with us, why wouldn’t those we work with? One of my challenges is high energy and spontaneity which can drive perfectionists and achievers crazy at times.

It is not a comfortable question to ask and requires self-introspection; but not asking it early on and often can lead to chemistry erosion which can be difficult to rebuild.

Asking this question to your boss and others will give you a menu of habits, behaviors, challenges and styles that you can begin to focus on improving in order to become a more effective and influential leader with the right level of coaching.

Changing perceptions changes reality, which changes outcomes.

  1. “What do you think is challenging for others about changes in your leadership style?”

What? You really want to get me fired is probably what you’re thinking. No, that is not the intent. This question will elevate you in the eyes of your boss and other leaders. Let me explain.

The notion that leaders are perfect is a figment of the imagination. Everyone knows that good leaders have areas they are working on to improve. We all have personal areas where we are trying to fill in leadership gaps. The problem is that leaders often don’t receive a private moment to share them with others or they try to conceal them because they may be interpreted as signs of weakness.

If leaders are honest and open, their answers will give you better insight of their awareness on how their leadership style impacts others, how that sits with them, and their willingness to improve in that area. Leaders who feel they are flawless and can’t become any better than they are, are what my high school football coach would call, “prima donnas.”

Your boss’s and peers’ response to this question will tell you a lot about them. The insight you glean by popping the question will give you an understanding of the personal leadership gaps they are trying to fill and may result in them asking you for help. Some leaders may feel this is a “no-no” and might put your career at risk.

I have found it is better to know the new habits and behaviors leaders are working on and be supportive of the change rather than putting yourself in the position of being caught off guard with everyone else who’s trying to figure out what the office scuttlebutt about Bob is all about.

Introspection is the key to leadership preservation.

  1. “Going forward, what is the best way to have open communication with the team?”

Many leaders discourage their direct reports from going straight to their boss about anything without their knowledge. To counteract this, many bosses intentionally undermine their leaders by talking directly to their subordinates without their knowledge. Sound familiar?

The irony in these scenarios is often that the communication between the leaders and their bosses is broken. This leads to an ineffective and dysfunctional organization. I once had a coaching client tell me that her C-Suite boss called five of her directors about a specific matter, and then called her on the same matter without disclosing that she had already talked to her bosses. Later my client found that her boss had then called other leaders in a different department on the same matter. It was so much confusion as to what the true issue was that to this day there are still disconnects throughout the organization.

Creating a mutual understanding of transparency and trust, and discouraging acts of leader terrorism which lead to disconnects is key to achieving extraordinary performance outcomes.

Getting a clear understanding of how communication will occur up and down the ranks is critical given the varying degrees of leadership and communication styles.

Trusted communication is essential for leaders amongst leaders in order to maximize potential.

  1. “How will we know when it’s time to redefine success and our roles?”

As leaders we all grow accustomed to a new job and a new role over time. A new job eventually becomes the new normal. The effect of a promotion and raise can wear off just like a new car smell.

Asking this question will remind others that you are a “growth leader,” not a “squatter’s-rights leader,” who milks a position until the closed-for-business signs are ordered and placed on the doors.

Broaching this subject will ignite conversations about your future goals and provide you an opportunity to develop an action plan to build additional competencies and skills that will propel you to the next level.

We all want to grow and want more. It’s natural. Unfortunately, we get stuck because we become comfortable. To go to the next level we must get comfortable asking questions and taking actions that make us feel uncomfortable.

Never feel that you can’t outgrow a job; your potential will always be bigger than the job description.

This article was originally published on

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Robert McMillan
Robert McMillan
A key distinguishing factor about Robert is that he is a former c-Suite executive with over two decades of industry leadership experience, who leverages that unique experience as an inspiring speaker, author, and leadership coach to executives, emerging and aspiring leaders, teams and organizations. He is a former c-Suite executive for Blue Cross Blue Shield, personally overseeing the Federal Employee Health Benefit Program, under the auspices of President Obama. He is known uniquely in the industry as the Leadership and Transformation Expert – the integrator of human and business potential. Robert helps aspiring, emerging and executive leaders transform their careers by igniting NextGen Leaders from within, based on his proprietary leadership development system. With over two decades of a unique combination of Fortune 1000 executive leadership, coaching and consulting experience, leaders connect naturally with Robert and see him as a partnering catalyst who facilitates behavioral shifts that result in personal and operational change, resulting in measurable improved outcomes. He is the founder of the NextGen Leader Institute, an international coaching and leadership development firm, and author of the book entitled, The NextGen Leader: Cutting Edge Strategies to Make You the Leader You Were Born to Be. His publications and articles have been featured in Training Magazine, Thought Leaders LLC, American Express Leadership Forum, and many other thought leadership platforms. His clients include, but are not limited to: Dimensions Health Plan, ASQ, Cambria, Trusted Health Plan, SHRM, NAHSE, Chartered Health Plan, Institute of Internal Auditors, AmeriHealth, McCormick, Department of Energy, NASA Goddard, Under Armour, University of Maryland, Rockwell, ICFI, Morgan Franklin, B.E. Smith, and many other corporations, associations and federal agencies. Robert has received one of the highest designations as a Professional Certified Coach (PCC) by the International Coach Federation (ICF) and is a graduate of the Georgetown University Executive Coaching program. He holds an MBA and MS from Johns Hopkins University; and a BS in Corporate Finance and Marketing from Virginia State University. He lives in the Maryland and enjoys spending his time writing, telling stories, chasing a little white ball, and traveling with his wife, Yolanda, and their two teenage children, Journee and Jalen. His purpose in life is to inspire people to maximize their potential and ignite the genius within.


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