7 Questions Leaders Should Ask Other Leaders, But Don’t

Guest Post by Robert C. McMillan –  Leadership Potential Coach, NextGen Expert and Inspiring Speaker

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 your either your boss and or peers.

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 – 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 backwards. In a safe environment asking thought provoking questions early on, with the right leader, changing behavior, and being agile, 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 can do today, differently, to evolve into the next generation leader you, and in parallel improve business outcomes? 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 than 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 new 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 sometimes changes. More often than not the issue arises usually when a meeting, decision, or outcome is the opposite of the desired.

Having a transparent conversation about the vision of your role will help you to identify whether you are capable of playing that role; and 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.

2. “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 question. Having a strong relationships is ever so critical now than ever before.

The degree of the relationship with other leaders will determine the organizations 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.

3. “What is your biggest frustration or feelings of disconnects in my area of responsibility?”

Every now and then, talent supply produces and 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 every now and then.

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

No matter how tight your shop is run, seeking transparency around feelings of frustration, disconnects and confusion puts you well ahead of the game to take action while there is plenty of time remaining on the performance clock to resolve the misunderstandings, challenges or issues and be recognized as a high performing leader, as a result.

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

4. “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 because they have not come out right and blatantly told you, or perhaps because most people never ask the question. Think about it this way, if our family members, spouses, significant other 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 to become a more effective and influential leader with the right level of coaching.

Changing perceptions, changes reality, which changes outcomes.

5. “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 we are trying to fill leadership gaps in. The problem is leaders often don’t receive a private moment to share it with others or they try to conceal it because it may be interpreted as a sign of weakness.

If the leader is honest and open, their answer 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 they can’t become any better than they are, are what my high school football coach would call, “Prima Donnas.”

Your boss’s and peer’s response to this question will tell you a lot about them. The insight you gleam 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 may 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 scuttle about Bob is all about.

Introspection is the key to leadership preservation.

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

Many leaders discourage their direct reports from talking directly to their boss about anything without their knowledge. To counteract this many bosses intentionally undermine their leaders by going 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 direct report directors about a specific matter, and then called her on the same matter without disclosing they had already talked to her directs. Later she found after talking to her, they then called other leaders in a different department on the same matter. It was so much confusion as to what the true issue was 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 leads 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 to maximize potential.

7. “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 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 you can’t outgrow a job, your potential will always be bigger than the job description.

Now it’s your turn: What do you wish you could ask other leaders? Please ask your question to this community of leaders and comment on this post.

Note from Bob:  The best leaders always ask others “How am I doing?”  And then listen!



Robert C. McMillan is an Executive and Emerging Leader Coach, NextGen Expert and Inspiring Speaker, for mid – high potentials, high-performers, and executive leaders. He helps leaders, teams and organizations, evolve into the “next generation” they desire to become, resulting in accelerated change, increased performance and extraordinary business outcomes.  He is the founder of the NextGen Leader Institute and author of The NextGen Leader: Cutting Edge Strategies to Make You the Leader You Were Born to Be.  Robert is a thought leader in leadership development and human potential, receiving one of the highest designations, as a PCC level competency, Certified Coach, by the International Coaching Federation, and is a graduate of the Georgetown University, Institute for Transformational Leadership, Executive Coaching Program.  You can connect with Robert on his website:  www.nextgenleaderinstitute.com  or via e-mail: robert@nextgenleaderinstitute.com


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3 thoughts on “7 Questions Leaders Should Ask Other Leaders, But Don’t

    1. Bob Tiede says:

      Robert – thank you for writing this great post!

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