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7 Questions on Leadership with David Hole

Name: David Hole

Title: Digital Transformation Consultant

Organisation: Evangelize Consulting Ltd

I am an accomplished technology leader with over 25 years of experience driving digital transformation and innovation for global financial institutions. I have led complex initiatives, including systems integration, cloud adoption, operational efficiency, and customer experience improvements, generating millions in savings and revenue gains for Financial Institutions such as Credit Suisse, Barclays Bank, UBS, JP Morgan and Lloyds Banking Group.

An innovative thinker who is skilled at implementing new technologies like AI/ML to solve problems. A strategic planner able to align technology roadmaps to business goals for maximum impact. A proven change agent and team builder who motivates cross-functional groups to achieve shared visions that highlight core strengths in managing vendor relationships, portfolio governance, budget oversight, and building adaptable infrastructure.

Passionate about leveraging broad technology expertise and business acumen to deliver transformation programs on-time and under budget. Especially interested in end user enablement and information exchange with a view to helping and educating teams to perform and engage better.

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

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


Jonno White

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

A few things spring to mind:

Getting alignment and buy-in across complex global organisations with multiple stakeholders and competing interests Effective communication, influencing skills, and painting a compelling vision are crucial to getting everyone on the same page.

Managing dispersed international teams and bridging cultural differences. Being adaptable and embracing diversity while fostering common purpose is key.

Balancing long-term strategic thinking with short-term demands. Keeping teams focused on the bigger picture while still delivering quick wins is tough but vital.

Leading through uncertainty and change. Transformations cause disruption. Keeping morale up, managing anxieties, and embracing agility even when the way forward is unclear are hard to get right

Letting go of control and empowering others is also a difficult skill to learn but I now know when to trust my team and give them autonomy to accelerate personal growth.

Work-life balance. The relentless pace of transformation allows little downtime so finding a balance between professional and personal priorities is tough but essential.

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

I have a sporting background in football, cricket, golf, and general fitness, so I think that this has influenced me into being someone who leads from the front but who also gets the best out of others by being honest, fair, and someone you can trust. Many people say they do these things but abandon this approach when things get tough. I think sports train you to not allow fear of failure creep into your professional life.

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

I structure my days the same every day. I like things to be repetitive in when you work, go for a run, or see your family.

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

Don't think that getting into business with a friend or ex-colleague is a sure-fire thing that will work out. People change their opinions and attitudes when working closely on something that they now own, and its not the same.

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?

I read a book by "Winners and How They Succeed" by Alastair Campbell, and in that book was a quote that read, "I was never that bothered by winning, but I hated losing more."

When I read that, I realised that for the past 50 years I have been more hung up on trying hard not to lose at anything because it was a horrible feeling. When I have won in sports or in business, it always felt like something wasn't really that great... Now I know why.

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

Be honest and fair, and be prepared to do things that will not be popular. If you are fair with people, they will respect you even if they disagree. Don't try to allow too much for people's feelings as this always works out badly.

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

I worked for a property company and built a team of 130 people delivering technology services that was widely regarded as the best in the business.

I thought that if we were cost neutral, and providing great services to the firm that would be enough to continue the upward trend of the teams positioning within the firm. I was wrong.

My boss did not see the reflection of the team as being his win, his boss didn't see the team as being his win because it was based in EMEA and not in the USA and I didn't catch this political position at all.

The first time that the overall business results took a downward turn the team was disbanded and stripped down to the bare bones of about 15 people.

In reflection there probably was not a lot that I could have done to change this. If I have learnt one thing from this experience and the 7 years it took to perfect that team and get it to the very best it could be, it was that as a leader you have to be aware of the drivers of other people.

If I had realised that my success was not someone elses success those 130 people would still be in a job as I could have positioned the team differently. Being the best you can be is sometimes not enough.

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