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7 Questions on Leadership with Bashir Agboola

Name: Bashir Agboola

Title: Vice President/Chief Technology Officer

Organisation: Hospital for Special Surgery (HSS)

Bashir Agboola is an award-winning technology and business transformation executive that has spent the last couple of decades helping some of America’s most prestigious healthcare institutions achieve their technology-driven transformation goals.

Bashir has an extensive leadership and technology management background, ranging from IT Systems integration, Consulting and Healthcare IT. His consulting engagements led to his entry into the healthcare industry, providing technology expertise and leadership to some of America’s leading healthcare institutions, including Memorial Sloan-Kettering Cancer Center, and the Hospital for Special Surgery, (the global leader in Musculoskeletal/Orthopedic health), where he currently serves as Vice President and Chief Technology Officer.

Bashir also has experience delivering value to organizations through his board membership roles. He currently serves as a member of the Board of Directors at the Center for Family Support of New Jersey, and also lends his expertise to various advisory groups, Including the Transformational Leadership Program Advisory Board at the Stillman School of Business (Seton Hall University).

He is a respected thought leader on technology, health-tech, and leadership matters. He writes and speaks frequently on these topics for industry publications and conferences across the United States and beyond. He also holds several professional certifications.

Bashir has received multiple recognitions for his accomplishments, including the HMG Global Leadership Institute Award (June 2021), Top 100 CIO/CTO Tech Inclusion Award (March 2021) and the HMG Strategy 2020 Technology Executives Who Matter Award, a recognition that, in the words of the awarding global organization, “honors premier leaders who have delivered unparalleled value to their organizations in innovation, business transformation, digital disruption and talent development”.

He holds a bachelor degree in computer science with Economics, a master degree in Computer Science, and an MBA in Finance.

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

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


Jonno White

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

I believe leadership is, to a large extent, an exercise in influence and decision making. A leader makes decisions and tries to influence people to act on them. Sometimes the leader has power behind their influence, often they don’t. Sometimes they have lots of good information to inform their decisions, often they don’t. So, I find that I must constantly learn and understand how to best influence each of my various stakeholders (including my team), and to make decisions (often with imperfect information) that the team will trust and act on.

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

My leadership journey began in college with my holding some leadership roles in a student organization. The experience of leading a group of strong-willed, idealistic, and highly opinionated college students helped shape my leadership skills and influenced where I focused some of my early professional development efforts. All of that paid off when I was recognized for progressively highly leadership opportunities in the workplace.

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

I am an early riser. My day starts off with prayers and meditation, followed by a nice cup of tea. I do my best thinking and other creative endeavors early in the morning, so I spend some time on any complex study, or writing exercise that I need to work on at that time. I then workout a bit, though I must admit that I still struggle to be consistent with my workout.

Most days I commute to work and spend part of the time in transit reviewing my schedule for the day (I try to do that the previous evening as well, but do it again early in the morning in case there has been any changes). I spend the rest of my commute time reading or listening to a book, listening to the news, or catching up on personal or work emails.

The workday is often busy, with a variety of scheduled events and engagements with the team. There might be an occasional webinar to attend, or to present at. Occasional technical issues might require a restructuring of my plans as I join my team in focusing on addressing any service issues we might be experiencing.

At the end of the workday, the commute back home is often spent listening to the streaming news service or catching up on personal emails and WhatsApp messages. On particularly stressful days, I just spend the time in mental solitude, using that time to decompress before getting home.

I eat dinner with the family early in the evening since I usually choose to skip lunch. Parts of the evening is spent engaging with the family at home or on phone calls with family and friends elsewhere. I then spend the rest of the evening watching TV with my wife (news, movies, documentaries). Then off to bed.

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

I was recently reminded of the importance of “Informed Empathy”. One of the struggles leaders sometimes face is that of balancing the need to protect the interest of their organization with a recognition of the challenges the people that make up that organization face in their individual lives. For example, figuring out how to support a subordinate with serious performance issues at a time the staff member might be going through some individual challenges in their personal lives, while also protecting the interest of the organization and the team. Simply being empathetic towards the employee might not be feasible, might hurt organizational effectiveness, and might even have a corrosive effect on team dynamics if a poor performer is seen as being tolerated simply out of pity. Allowing empathy to inform your response to the performance issues however would shape how you approach the issue and what options you consider as you work to protect the organization, the team, and the struggling team member.

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?

My favorite business book is Influencer, the Power to Change Anything, by Joseph Grenny, Kerry Patterson, et al. (there is a new edition out with slightly subtitle). The book crystallized for me the understanding that leaders have tremendous power for good by being able to use effective influence skills to effect change on small to massive scales in a variety of context. This remains my favorite business book.

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

Fear is one of the biggest impediments to our growth, and young leaders can experience this a lot more than seasoned professionals. So, one piece of advice I share often is that you need to get comfortable with being uncomfortable. What that means is that instead of trying to eliminate the feeling of discomfort or fear that holds you back from doing the things you need to do to grow as a professional and as a leader, recognize the presence of that discomfort (you can even name it), and then act despite it. Stop trying to not feel afraid. Act despite your fear. Focus on what benefit you seek out of the action.

I give the analogy of getting a vaccine shot. We know before getting it that we will feel the pinch of the need and might even feel some soreness at the injection spot for a few days. Despite that, most of us are able to overcome any fear of the discomfort, not by making the discomfort go away, but by looking beyond it to the benefit that we seek from the vaccine. When we get comfortable with discomfort and act despite our fears and anxieties, we often end up feeling less of that fear in the moment or with time.

So, the next time you have to give a presentation, have a difficult conversation, ask for a raise, or introduce yourself to senior person you are dying to meet, recognize that fear you feel, smile at it, and go for your goal. You got this!

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

I work in healthcare as a technology leader. I am not a clinician. However, one of the most meaningful events I have experienced on the job is when I hear from patients who have been cared for at my organization stating how wonderful the care they received was, and how thy feel that my role as a technologist had to do with it. I share these with my team often to remind us all of why we do what we do.

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