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7 Questions on Leadership with Chris Hippensteel

Name: Chris Hippensteel

Title: Director of Information Technology

Organisation: New Resources Consulting

Chris Hippensteel, a seasoned professional at 35, holds the esteemed position of Director of Information Technology at New Resources Consulting. Married to Dr. Liz Merriman, he resides in Bay View, Wisconsin, alongside their cherished companions—Harley, the dog, and Mango, the cat. Specializing in IT Security and Networking, Chris brings a wealth of expertise to his leadership role.

Beyond the confines of his professional endeavors, Chris is a multifaceted individual. A connoisseur of music, he actively engages in playing instruments. Additionally, he channels his passion for craftsmanship and adventure by indulging in the construction and riding of custom motorcycles. Chris and his wife, Dr. Liz Merriman, share a penchant for global exploration, traversing the world to savor diverse cultures and culinary experiences. His dynamic pursuits both within and outside the professional realm exemplify a commitment to excellence and a rich appreciation for life's myriad facets.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Chris's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

The foremost challenge I have encountered as a leader lies in the delicate equilibrium between authoritative leadership and fostering an inclusive, welcoming atmosphere within my team. While acknowledging the professional nature of our collective responsibilities, I abstain from the notion that our workplace is a surrogate family. My pursuit is rooted in cultivating a harmonious work-life balance, recognizing the intrinsic value of time outside the professional realm.

In a society where the majority invests substantial hours in the workplace, often exceeding the conventional eight-hour workday, it becomes imperative to curate an environment that beckons enthusiasm and commitment. My conviction is anchored in the belief that our daily professional pursuits should seamlessly integrate with our personal lives. As we return home to limited hours with family and friends, the workplace should not be an entity that merely extracts time but rather an engaging domain that inspires fulfillment.

This comparison poses the quintessential challenge – transforming the workplace into a haven that beckons dedication while cognizant of the imperative to construct a formidable, high-performing team. Navigating the labyrinth of individual disparities, especially in the nascent stages of leadership, underscores the complexity of this endeavor. It is in surmounting this challenge and perpetuating the equilibrium between professional rigor and a welcoming workplace culture that defines the mettle of a leader. Each team member is a unique entity, and deciphering the nuanced balance tailored to individual proclivities remains an ongoing pursuit—one that delineates the trajectory of effective leadership.

2. How did you become a leader? Can you please briefly tell the story?

The trajectory of my ascent to a leadership role within the realm of technology is underpinned by an unwavering commitment to diligence and perseverance. Following the attainment of an associate's degree, I embarked directly into the dynamic domain of IT security. A pivotal juncture saw me relocate from Milwaukee, WI, to Chambersburg, PA, marking the commencement of my inaugural professional foray.

The initial rungs of my career ladder were traversed through a succession of roles, beginning with telephone support and extending to multifaceted responsibilities such as password administration, ticket resolution, network management, and the construction of comprehensive security frameworks. This evolutionary journey culminates in my current capacity as the head of an IT Department.

Undoubtedly, this progression was fraught with challenges, and the odyssey from telephone queries to organizational IT governance was far from facile. Yet, the crucible of adversity served as the crucible for honing my skills, fostering resilience, and cultivating the essential qualities inherent to effective leadership.

Reflecting upon this trajectory, it is unequivocally the combination of unwavering exertion and dedication that has propelled me into the leadership echelon. The mirror, as a metaphorical arbiter of self-assessment, affords a tableau wherein the man gazing back is a testament to the cumulative fruits of labor—a leader forged in the crucible of ceaseless endeavor and dedication.

3. How do you structure your work days from waking up to going to sleep?

Commencing the day entails adherence to a regimented routine encompassing essential personal activities: hygiene, attire selection, tending to my canine companion, and exchanging farewells with my wife as she embarks on her professional commitments. Upon arriving at the office, my initial pursuit is the fortification of alertness through the infusion of caffeine, concurrent with the boot-up sequence of my computer.

Subsequent to this preliminary phase, I engage in a comprehensive review of the day's calendar, strategically prioritizing tasks in accordance with exigencies and ongoing departmental requirements. Central to my daily operations is the adept handling of high-level ticket requests, participation in pivotal vendor meetings, and a meticulous examination of my team's undertakings.

Upon the end of the workday, I return home, where my time is allocated to various pursuits, including quality moments spent with my dog. My leisure activities span the spectrum from musical interludes—featuring occasional collaborative jam sessions with friends—to the mechanical artistry of working on motorcycles and indulging in recreational rides. There are evenings dedicated to the creation of home-cooked meals and picking the perfect movie in a thoughtful selection for the night's viewing.

Prior to retiring for the night, a routine involves perusing articles of interest, ascertaining the weather forecast for the ensuing day, and ultimately succumbing to the embrace of restorative sleep. This structured delineation of my waking hours underscores a judicious balance between professional commitments and the pursuit of personal passions, fostering a holistic and fulfilling daily regimen.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

A recent leadership epiphany has underscored the imperative distinction between professional and personal spheres, dispelling the notion that the workplace should emulate familial bonds. This realization crystallized during a thought-provoking session at a recent conference, wherein a discernible effort to mitigate the encroachment of potentially deleterious behaviors was emphasized.

While collaborative teamwork remains pivotal, the delineation between individuality and the cultivation of personal and familial connections outside the professional milieu emerged as a salient focus. The imperative of compassion as a leadership attribute was not discounted; however, a judicious demarcation between the exigencies of work and the sanctity of personal life was extolled as the hallmark of sagacious leadership.

Contrary to any dissenting perspectives, my conviction rests upon the premise that our existence transcends the mere orchestration of work. The pursuit of a life imbued with purpose and fulfillment necessitates an acknowledgment of the indispensability of personal space and familial connections. The commitment to work is undeniably requisite for global participation, yet it should not supersede the pursuit of a life authentically lived.

In building for the future, the admonition remains salient: not to permit the radiance of the present to be overshadowed by the exigencies of labor. The essence of effective leadership is encapsulated in navigating this delicate balance, fostering both professional excellence and a life rich in meaningful experiences.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

While my exploration of leadership literature has been relatively limited, I find myself subscribing to the notion that true leadership is a culmination of experiential learning, guided by hands-on experiences and interpersonal interactions. While I have delved into numerous seminars and TED Talks on leadership, I have not identified a singular book that has significantly shaped my leadership philosophy.

In my perspective, leadership is an acquired skill set, honed through a dynamic interplay of learning from both successes and mistakes. The intricate fabric of leadership is woven through firsthand experiences, interactions with others, and the adept navigation of challenges. While books may serve as supplementary resources, the essence of leadership is a multifaceted journey, uniquely tailored through practical engagement and continuous refinement.

6. If you could only give one piece of advice to a young leader, what would you say to them?

The singular piece of counsel I would impart to a burgeoning leader is encapsulated in the tenets of unwavering diligence and steadfast dedication. As an unconventional figure in the leadership milieu—adorned extensively with tattoos, a testament to my longstanding fascination with the art form—I have transcended preconceived notions of the conventional leader.

For a considerable duration of my professional trajectory, I harbored the misconception that there existed a predetermined template dictating the appearance and demeanor requisite for leadership. It was only in the last six to eight years that a profound realization dawned: leadership is not confined by external stereotypes but rather forged through the crucible of tireless labor, dedication to one's vocation, and a nuanced comprehension of guiding and uplifting others.

This revelation shattered the fallacy that outward appearances are intrinsic to effective leadership. Instead, I have come to appreciate that the essence of leadership emanates from a profound understanding of one's craft, coupled with the ability to inspire and elevate those under one's purview. Embracing this paradigm has not only liberated me from the constraints of stereotypes but has also empowered me to foster a new cadre of leaders among the younger demographic, transcending conventional expectations and shaping the leaders of the next generation.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

During a recent lunchtime reprieve, where I frequented a local restaurant to momentarily disengage from professional exigencies. My inclination, when dining alone, is to opt for a bar stool, allowing for a swift repast and facilitating a condensed lunch break.

On this particular day, my focus shifted beyond the perimeters of my immediate professional sphere, as a conversation unfolded with a young bartender. Inquisitive about my professional trajectory, he conveyed uncertainties regarding his own vocational path and aspirations for change. Recognizing an opportune moment for mentorship, I attentively listened to his ambitions, delving into a discourse on the transformative power of taking calculated risks.

Our dialogue extended beyond the confines of that lunch hour, culminating in the formulation of a concise cover letter aimed at leveraging his existing skills to align with his desired field. Subsequently, I revisited the establishment, delivering the document and continuing our conversation regarding potential internships and entry-level opportunities in alignment with his aspirations.

While the denouement of his journey remains unknown, the encounter underscores the transcendent capacity of leadership beyond the workplace. It serves as a testament to the profound impact that mentorship and guidance can wield in catalyzing personal and professional growth. My aspiration is to perpetuate a legacy of fostering such transformative connections and aiding individuals, irrespective of age, in realizing and pursuing their ambitions.

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