On this episode of Denim Rivet, we are joined by Ann Dieleman. Ann is owner of Ann Dieleman Consulting, where she helps companies grow and adapt to changing market conditions. We’ve brought her on the show to discuss her thoughts on leadership and insurtech, her experience in the industry, and why she attended the inaugural Denim Summit on October 26. Ann is from Iowa and is endlessly intrigued by the intersection of insurance and technology – namely its ability to yield great consumer experiences for a product that has historically been viewed as a necessary evil. 

Leadership Qualities

For Ann, some of the best leadership qualities can be summed up by a “people first” mindset. She is firm in her belief that growth creates opportunities for others. Being a great communicator is critical to harnessing leadership potential, as people fill in the gaps where there is an absence of information. Being transparent is the best way to eliminate fear, which is the number one inhibitor of creativity and progress for any team.

Maintaining a servanthood mentality is another trait Ann mentions. Actively searching for the barriers that stop others from accomplishing their goals should be a daily task for any leader. She worked with one CEO who asked a single survey question: What is the number one thing stopping you from doing your best work? Figuring out how to get around those barriers becomes much more manageable once you know what those barriers are.

Constructive feedback is something Ann believes needs to be a daily focus, not just brought up in a yearly performance review. Feedback needs to be in real time and built in as a daily habit as part of a (hopefully fun) company culture that prides itself on progression and personal successes.

Challenges in the Workforce

Today we have multiple generations in the workforce, coupled with a rapidly changing technological advancements. It’s a lot to take in. A key to managing this is increasing leadership bandwidth, and this can be done by identifying and communicating what success looks like to those you lead. This is just one task that needs to be scheduled (daily) to drive you to your leadership goals. If you wait for a time to work on leadership all at once, that time will never come. Just like any product, your leadership should be advanced little by little and consistently.

Staying Relevant

For Ann, staying relevant in the changing marketplace comes down to attitude. She keeps the mindset of always being in “beta,” which helps her come to work every day driven by curiosity and improvement. Reading is a huge component of learning new things in order to better gauge an industry and its evolution. Just reading through a few tweets everyday doesn’t really cut it. Ann is an early adopter of technology as well – there’s no better way to put your finger on the cutting edge and see what eventually works (and why) or, just as important, why something failed. 

Career Advice

Ann surrounds herself with the best and smartest she can find – not so they can boost her ego, but so they can debate her and challenge her viewpoints. Hearing what you need and not what you want from peers is crucial to advancing. Another thing to accept is that great change rarely comes from within our comfort zone. Reaching out to other experts and industries helps pushes you to think outside of the box and broaden the scope of possible solutions to the challenges you face.

Contact Info

Ann Dieleman: 816-891-9888
[email protected]