The 3 Critical Questions Every Leader Should Ask

leading in difficult situations

Held as a prisoner of war for nearly 8 years, Vice Admiral James Bond Stockdale was the senior ranking American officer at the “Hanoi Hilton,” the nickname for the North Vietnamese prison camp holding American prisoners of war (POW) from April 1965 to February 1973.

During his time as a POW, Stockdale was regarded for his exemplary acts of leadership. He displayed composure, warmth, and the uncanny ability to sense the morale of those in his care. He held an unwaveringly resistant, yet humane posture towards his captors. He maintained both a hope for circumstances to improve, while pragmatically acknowledging the facts of his current situation.

It is perhaps this latter quality that is most emblematic of his leadership – the propensity to be both hopeful in the unknown and fearless in confronting the right now. In fact, the ability to at once hold the positions of hope and realism has been dubbed the Stockdale Paradox (Groysberg & Abrahams, 2020). It was this perspective that Stockdale, and many of his fellow POWs, credit for their survival in the camps.

The power of this perspective continues to show its value today, most recently demonstrated with the United States Navy’s newest Get Real, Get Better initiative. A push for “Navy leaders to have the courage to self-assess and build teams that embrace an honest, hard, transparent look at their performance to understand actual strengths and weaknesses,” all in the service of improvement (Get real, get better, 2022).

This approach notes a departure from the “strengths-based movement” which focused on identifying and building upon skills one already possesses. Instead taking the position that there is more progress to be made in focusing on both what is working well, and what needs correction. In fact, evidence suggests that critical feedback can provide the necessary motivational force to spur corrective action and elevate self-awareness (Fong, et al., 2019). Additionally, research shows that a strengths-based approach to development can lead to a false sense of competence and propensity to silo your skillset (Chamorro-Premuzic, 2016; Pierce & Aguinis, 2013).

Seemingly in tandem with the strengths-based movement, are the waves of organizations who have chosen to replace words like “challenges” or “weakness” with words like “growth areas” or “developmental opportunities.” However they all get at the same idea – describing gaps in one’s current capability or awareness. How an organization chooses to label such terms is a product of their context and culture. However, what should be far less acceptable is ignoring that we all have weaknesses and if left unaddressed we are practicing wishful thinking rather than a targeted action plan towards improvement.

As a leader, getting better starts with getting real and fearlessly pursuing information that supports improvement. This starts by asking yourself three questions:

  • How do I see myself?
  • How do others see me?
  • How do others see themselves because of their interaction with me?

The collective insight from these three questions encapsulates a leader’s total impact on the world around them – an insight critical for meaningful development.

Let’s focus on each question:

1. How do I see myself?

This question invites you to explore the components of your identity. While such a question can feel broad, consider it within the parameters of internal experiences – When do you feel at ease with yourself, or in tension? What motivates excitement and action for you? When do you feel most uncomfortable? Outlining elements of your internal state allows you to both raise your awareness and promote your ability to regulate these sensations when they arise.

2. How do others see me?

Having an appreciation for how you see and experience yourself is a starting point for getting better. However, its utility can be limited because in most all we do, we do with others. An even more useful insight is knowing how you are seen by the people around you. Since no one can see your intentions, thoughts, or feelings, ensuring your behavior is what you intend it to be is critical for “showing up” in the world purposely. Consider asking, how do others see me? What feedback have I been given? How would others describe me? Getting clearer about the elements of your external state allows you to more effectively regulate social interactions and manage relationships.

3. How do others see themselves because of their interaction with me?

This question is about your impact. Your presence impacts the people around you. This impact may range from strong to negligible, or positive to negative. Can you sense how your peers feel when they have to collaborate with you on a project at work? Are your direct reports hesitant to bring issues to you or do they share information quickly and freely? Considering how you want people to feel before, during, and after they interact with you builds your social awareness and contributes to more desirable relationship outcomes.

Seeking out honest insights about ourselves is a courageous act, as it is very often an uncomfortable one. We may resist out of fear from what is to be learned about ourselves, we may question the credibility or sincerity of others’ observations, or we may be unconvinced of the importance of knowing this information. But like Admiral Stockdale, we must relentlessly pursue the facts of our reality with the hopeful intent that they will help us move the needle of progress.

Written By Jacob Westerberg


Chamorro-Premuzic, T. (2016). Strengths-based coaching can actually weaken you. Harvard Business Review, 4.

Fong, C. J., Patall, E. A., Vasquez, A. C., & Stautberg, S. (2019). A meta-analysis of negative feedback on intrinsic motivation. Educational Psychology Review, 31(1), 121-162.

Get real, get better. (2022, August 25). United States Navy.

Groysberg, B., & Abrahams, R. (2020). What the Stockdale paradox tells us about crisis leadership. Harvard Business School Working Knowledge, 4.

Pierce, J. R., & Aguinis, H. (2013). The Too-Much-of-a-Good-Thing effect in management. Journal of Management, 39(2), 313–338.


Dr. Jacob Westerberg is an organizational psychologist and active-duty U.S. Naval Officer. He is the Associate Director at the Mitchell Center for Prisoner of War Studies, where he leads research on resilience and leadership among former American prisoners of war to support current service member development. As a certified coach, Dr. Westerberg provides assessment and development services to leaders in government and private sector organizations.

Dr. Westerberg is a guest writer for TalentSmart EQ. TalentSmart is the leader in emotional intelligence training. For more information about Leadership and Emotional Intelligence, please contact us at or check out:

Disclaimer: The views represented in this article are that of the author and do not represent the views of the United States Navy or Department of Defense. Any inquiries regarding this work should be directed to the author.

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