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7 Questions on Leadership with Olusola Osinoiki

Name: Olusola Osinoiki

Title: Director

Organisation: Josh Leadership LTD

Sola Osinoiki is a business executive with over 25 years of working experience in the Tech industry. Sola has spent numerous years working on global HR systems implementation and consulting with major international organisations and fast-growing Small and Medium Size businesses. At the heart of what Sola does is helping businesses understand HR IT solutions, including bespoke developments and off-the-shelf technologies. He has gained extensive experience in the HR Technology and Data arena as a client, implementer of services, and a seasoned advisor.

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

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


Jonno White

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

In my capacity as a leader, I have come to recognize that one of the biggest challenges I have encountered pertains to the management of people. Human beings, by their very nature, are intricate and multifaceted, yet it is they who ultimately confer upon one the designation of a leader. A true leader is defined by their ability to inspire and guide others. It is incumbent upon us to lead effectively, for without willing followers, leadership remains an empty title. Managing the complex intersection of getting the best out of people and ensuring in that process they feel personal development and growth is a constant challenge

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

After a few years in my career, I personally started to grasp the nuances separating management from leadership. It was during my time at PwC, when I was at the level of Senior Manager, that I experienced a deep personal realization of the stark contrast between these two vital roles. That is when my journey in true leadership started

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

While I naturally tend to be an early riser, I've also come to appreciate my ability to function effectively as a night owl when circumstances demand. With the transition to managing my own independent practice, my daily schedule has undergone some notable shifts. Additionally, I occasionally find it necessary to remind myself of the time zone in which I am currently situated.

My approach to managing my day is centered on calendar. Given the diverse range of clients I serve, I find it imperative to fully align my daily activities with their respective needs. Consequently, I commence each day by adhering closely to my calendar, allocating focused time for the specific requirements of each client. I also seize any available gaps in my schedule to attend to emails, maintain connections with my family, and make progress on personal projects.

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

A valuable leadership lesson that has been prominently reinforced in recent times for me is the profound significance of empathy in our interactions with others. The current climate presents a multitude of challenges for individuals, making it imperative for leaders to cultivate genuine empathy. This skill plays a pivotal role in building trust and fostering strong connections with our teams.

In my role as a Coach Mentor, I have personally witnessed the transformative power of empathy. Working closely with individuals as they navigate their unique transitions has underscored the importance of understanding their perspectives, feelings, and needs. This empathy-driven approach not only enables them to thrive in times of change but also strengthens their trust and confidence in my guidance.

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?

One book that has significantly influenced my perspective is "Winning: The Unforgiving Race to Greatness" by Tim Grover. This book has left a profound mark on my leadership journey, compelling me to reevaluate my approach. It articulates a compelling thesis: true victory demands unwavering dedication and a relentless pursuit of excellence.

As a leader, this book has been instrumental in challenging my fundamental beliefs. It underscores the inherent toughness of the journey towards success, emphasizing that achieving greatness necessitates a wholehearted commitment. To guide individuals toward new horizons in the realm of business, career, or personal development, it is essential to grasp the intricate dynamics of the innate drive to succeed, both for oneself and for those under one's leadership. This understanding is a crucial aspect of my role as an empathic mentor and coach, as it empowers me to lead others towards their own paths to success.

PS: I read the book every year as a refresher. Check it out!

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

If I were to offer a single piece of advice, it would be to actively seek out mentors and coaches to guide you on your journey. In the same vein, consider identifying individuals to support and invest in through your experience as a form of mentoring. Building these relationships not only fosters your own growth but also allows you to extend a helping hand to others, creating a reciprocal exchange of wisdom and experience that benefits all parties involved.

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

I vividly recall an experience I had at PwC, At that time, I was anticipating and getting prepared for a big promotion. Then, one day, out of the blue, my boss said to me, "I think you are ready for this (promotion), but you are missing something. "

“What do you think I am missing?” I asked.

He responded matter-of-factly, “You surely deliver on the goods but you have a lot of spelling mistakes in your emails. Even when you write to clients, sometimes you still have these spelling mistakes. I think you need to get yourself checked out.”

I appreciated his honest feedback, and took it in my stride. I agreed to undergo a dyslexia assessment, even though I was unsure what the outcome would be. My company generously paid for the assessment and at the appointed time, I went in to see the dyslexia specialist. As the test progressed, the lady looked increasingly worried.

After about an hour, she looked me in the eye and announced,

“You are 100 percent dyslexic!” Before I could gather my thoughts, she continued, “I have no idea how you got to your position as director without having had any help before now.”

Well, while I may not have had help up until that point, I knew I needed help going forward. So, with her guidance, we developed a strategy to help me manage the condition and deliver optimal results with fewer mistakes. I continue to use this strategy to date with remarkable results.

My point therefore is this: if you understand what your weaknesses are, you can address the problem. Take an audit of your life and identify your weaknesses. Do you lack the right kind of experience for a desired promotion? Or is it that your

network is not strong enough for the higher managerial position that you seek? Do you lack the natural presence and charisma of a leader? Once you know your weaknesses, you can begin to focus on those things that need to be fixed or adjusted.

However, the audit of your life should not be limited to identifying your weaknesses alone. It should also extend to identifying your strengths and maximising them. One person’s weaknesses are another person’s strengths.

Once you know your strengths, you should also devote time to optimising them. A knowledge of your weaknesses and strengths are the foundations that will help you ensure you manage your job correctly.

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