It takes 20 years to build a reputation and five minutes to ruin it. If you think about that, you’ll do things differently.”

To me, business isn’t about wearing suits or pleasing stockholders. It’s about being true to yourself, your ideas and focusing on the essentials

​John Doe


ABC Company

An Interview with Mr. Josh Brekenfeld


What’s one important leadership lesson you’ve learned in your career?


Leaders don’t have all the answers. Starting out in my career I remember thinking that the role of the leader is to know it all. Instead, I find that good leaders approach each challenge with a view point – and that they test that view point with the team around them. Good leaders know when to accept a recommendation that changes their thinking, and when to bring the team along to their way of thinking.

What are some important things that you have undertaken and have contributed to your success?


Authenticity. I think folks believe that leaders act a certain way – speak a certain way. I think leadership often gets confused with misunderstood ideas of professionalism. One of the best ways to get noticed is to be yourself and have your own viewpoint.


Luck favors the prepared. Luck may open the door for you, may get you that chance introduction, but if you are not doing your homework, honing your craft and developing your skill set, you may not be in a position to take that opportunity. Take charge of your own development and be curious about the industry around you – that way you are ready for when opportunities knock.


Get a hobby. I see too many people that just go to work and then head home. We all have to find the right work life balance – and I don’t think its easy, but for me, having a hobby means that I have some place to put my energy than dwelling too much in work mode or bringing too much work home.


What has been the biggest challenge you have encountered? Why and how did you handle it?


The toughest professional challenge I ever encountered was switching careers to insurance. I spent my first 10 years working in Washington, D.C. in public services. The switch to insurance came when my husband and I moved to London. Finding a new career was not easy – interviewers were fixated on the tasks and specific knowledge I had from previous roles – rather than looking at my broader skill set. I must have sat through over 75 interviews and phone calls all ending the same way: “you just don’t have the specific experience we are looking for.” It took a lot of time, and some help from a few recruiters to shape my narrative and hone my value proposition. The key was getting folks to think about my skills and then challenge my ability to pick up specific knowledge on the job.

How do you get your leadership team on board with diversity and inclusion initiatives?


At this point, I think it’s much more difficult to answer the question about how to incorporate diversity and inclusion into a corporate culture rather than having to justify it in the first place. Frankly, anyone who is questioning the value of culture in a work place is ignoring the facts – companies that are shown to focus on developing a strong corporate culture – that embeds diversity and inclusions initiatives – are constantly shown to out perform their peers. One of the more difficult questions to senior leaders is how to prioritize culture. Talking about culture as a business imperative and linking it to specific deliverables is the key to getting leadership teams to buy into diversity and inclusion initiatives.


What would you say is the most difficult part of implementing a D&I program/ culture?


A few years ago, I think the biggest challenge was showing businesses that diversity and inclusion matters – not just for the culture of the company, but that it actually increases productivity of employees, which has a direct impact on the bottom line. Now I see the challenge as embedding diversity and inclusion as a business as usual function – not just something you focus on for a short time. To do that well, you have to treat D&I as any other profit generating part of your business. You have to benchmark your D&I strategy to achievable, measurable outcomes – and play that back to senior leadership- making them accountable for delivering success or challenge when goals are not being met. This also means that it has to be led by the business – not just HR. At Aspen we formed Aspen Cultural Transformation (ACT) as a business led initiative to embed key deliverables and partner with our HR, IT and communications teams.  


What would the person you are today say to the person you were on your first day at work?


Stop worrying about what other people think so much. There is a time and place for constructive feedback- and you should welcome it- but that feedback is only useful to make you better at being you – never take feedback that is intended to try and make you someone else.


What is one interesting fact that we will be surprised to know about you?


For that, you have to buy me a drink first!

More about Josh:

Joshua (Josh) Brekenfeld was appointed Director of Global Corporate Development at Aspen in June 2019. Prior to this he spent six years at Lloyd’s of London, most recently leading the business oversight relationship between Lloyd’s and ten companies operating in the Lloyd’s market.

Previously, Josh worked as a development manager where he leveraged Lloyd’s insight to partner managing agents with business growth opportunities in Europe and Asia Pacific.

Josh also worked for 10 years in the U.S. Senate serving as the personal assistant to Dianne Feinstein, and later as the Deputy Staff Director of the U.S. Senate Rules Committee under Senator Charles Schumer. While in the Senate, Josh was also a member of the Joint Committee on Inaugural Ceremonies, which organized the 2009 Inauguration for President Obama.

Josh is admitted to the New York State Bar, a Liveryman of the Worshipful Company of Insurers (WCI) and holds a certification from the Chartered Insurance Institute (CII).

He is the chair of the iENGAGE group at WCI, founding member and former Chair of the Pride@lloyd’s resource group, as well as a founding member of the LGBT resource group for U.S. Senate employees. In 2018 Josh was named as a leading role model in the insurance industry and one of the Top 50 LGBT Future Leaders by the Financial Times.

In 2019, Josh became a Board Member and Trustee at The Insurance Charities.




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