Chris Loake, Group CIO at Hiscox: How to Run Towards the Hard Stuff

Episode Guest:

Chris Loake is the Group Chief Information Officer at Hiscox, where he leads global technology, data, and cybersecurity. With a career spanning finance, banking, and technology, Chris is passionate about resilience, adaptability, and building winning teams.

Episode Timestamps:

0:00 Introduction

0:43 Chris’s first ever podcast

1:17 From paper round to first jobs

2:00 Advice for your first day at work

2:32 From Harvester to accountancy

3:21 Why hating a job can be valuable

3:56 Discovering technology by accident

4:48 Building a first career plan

5:52 How to succeed with “no skills or experience”

6:38 Programming vs leading

7:14 Routes into technology: apprenticeships and bootcamps

8:25 Tech roles that aren’t coding

9:19 What makes someone “super techie”?

9:51 Lessons from technology for life balance

10:43 Building resilience through sport and work

12:03 Why you should never be the fastest in the club

12:26 Work with people who inspire you

13:02 What to ask in a job interview

14:02 Discipline vs motivation

15:21 How to stay disciplined in your career

15:50 Career pivots and lessons learned

17:04 Running towards the hard stuff

17:31 Why failure matters

18:04 The record label failure story

19:00 Why Chris chose business over entrepreneurship

20:28 What makes a true entrepreneur

21:38 Small business vs large business experience

22:46 Go where the people inspire you

23:32 Career pivots vs job hopping

25:00 Landing a first job in tech

25:49 What a Group CIO really does

27:04 How to experiment with new technologies

28:17 Transferable lessons between tech and careers

28:54 CIO vs CTO explained

29:33 The career steps needed for leadership in tech

29:39 Why Chris joined Hiscox

30:47 Technology as a competitive advantage

31:38 Supercharging people with technology

32:44 Why adaptability is the ultimate skill

33:27 From asking two questions to asking 200

34:15 Chris’s invisible success

35:23 Chris’s duvet flip – what gets him out of bed

Episode Partner

Hiscox, a leading international insurer with more than 3,000 employees worldwide. The company is known for specialist insurance solutions and a strong commitment to customer service.

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