Name: Jacob White

Title: Owner : fCCO

Organisation: ClientClimb Advisors

With over two decades of managerial expertise spanning diverse sectors, including military service and a pivotal role in a cybersecurity startup’s successful IPO, I bring a wealth of experience.

My current focus on aiding startups, founders, and new managers in creating human and customer-centric environments, coupled with fractional executive services, showcases my commitment to organizational growth.

My management consulting, particularly in customer-facing teams, emphasizes mentorship for holistic leadership development.

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

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

Cheers,

Jonno White

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

The biggest challenge is what is my biggest strength. I care too much about people. As a leader, it has taken me years to find that perfect line to walk where I maintain my authority as a leader without being too strict. While at the same not allowing people to take advantage of me. It takes constant communication, transparency, empathy, and empowerment. When you find those traits as a leader and your team, it makes expectation setting so much easier, and allows your team to drive their own success.

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

I started as a leader technically in the military. I worked up the ranks as enlisted to a Leading Petty Officer (E6) As a civilian though, I got my break as a leader in my first job outside of the military. Here, I was promoted from sales to a Branch Manager for the showroom. We operated with over $100m ARR, I did not know what I was doing.

It took a lot of time to understand the ins and outs of the position and the responsibilities I was responsible for in the role. I learned a ton in this position. Mostly the importance of setting your team up for success. The shock of being put in charge of people and a profit center with little to no experience and no one to lean on as a mentor or coach, I nearly failed.

Luckily my team worked with me and we all found success together. This was the beginning of how I found my method to drive success and maintain a human centric focus when leading an operation.

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

My day is not a single structured thing. Though I do have a few areas that I maintain in a routine. Generally, I approach my days as follows Wake up, coffee coffee coffee Get online, confirm my meetings for the day Check emails, flag any major ones to prioritize Check messages from overnight, when I am working on a team I make sure they all had smooth evenings. I look at any necessary reports and dashboards. Depending on what I am looking for the day.

I perform my daily meetings and/or tasks per my calendar. I engage with the team throughout the day As I wrap up my day, I confirm the next days tasks and meetings. Again, my structure will look different day to day. I do stick with my calendar and make sure I have my meetings set and stick to the calendar with vigilance. Especially when doing my 1-1s and team meetings.

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

Recently I had to coach a new manager through the performance improvement plan for one of their people. No matter how many times you do these, they are never easy and are all different. This came for a person who had been reported to be have inconsistent performance output by their past manager.

This new manager needed to go through the performance of the team member and get them to at least “meeting expectations” In the investigation of their performance, we observed that expectations were not properly defined for any position on the team. That these employees did not know what they were being measured against. They didn’t know what bad or good looked like.

The manager and I were able to put things down on paper and make things a little more operationalized for the individual contributors. We also scheduled out regular check ins to properly document individual performance and showcase with more details how this specific employee would be able to boost their performance.

In doing this prep work, we were hit with roadblocks by the employee where they did not appreciate the guidance and definitions. They felt that the manager was singling them out and that they had done a solid work performance in their job. Using previous performance reviews from the past as their evidence.

This experience made me remember that not everyone will react positively to the efforts you make to help. And allowing poor performance to fester as they had, it can breed a lot of unexpected reactions that need to be addressed swiftly and comprehensively.

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?

It’s a weird one….its a parenting book by Dr Sears “The Baby Book” It is interesting, but being a manager you are growing budding careers. At the very least, you are in a position to help that individual be really good at the job they have. If not growing to their next position.

This book always sticks in my mind. Keeping the autonomy of my individual contributors. It has grounded me in methods and practices when working with people, treating them like people. Remembering they have feelings, they have lives, they are people. The parallels I draw have keep me in line to help me be a more empathetic leader.

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

I would let them know that you will mess up. Keeping your triumphs and your losses exposed to all will allow you a level of transparency and respect that other leaders lack. Constantly look out for your team and keep their backs protected.

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

I have had the honor to lead and manage hundreds of people. In this work, some of the most rewarding experiences have been watching my team members improve themselves and in some cases surpass even me in their career journey. I have connections and contacts, and am very happy to work with even today to help get them where they wish to be. I am a mentor.

One time I had to leave a place where I was a high level director. When I left, I was told there were tears and people needing to take mental health days to cope with my departure. I learned a lot on exiting companies with this, but it was very meaningful to me as I became fully aware of the overall impact I had on the teams and organizations.