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Managing Your Careers in the Future of Work

February 27, 2020



Managing Your Careers in the Future of Work

Managing Your Careers in the Future of Work

Ben Brooks is the Founder and CEO of Pilot Inc., a software-based employee coaching platform. Business leaders are struggling to find the right methods to keep their most talented employees away from the competition. Retention is highly personal and each employee has their own motivations, desires, and goals, yet we still approach retention with a one-size-fits-all approach. Ben explains on this week’s episode that there is a better way to keep those sought after employees.


[00:58] Every individual should plan to have 5 careers in their lifetime.

[01:52] Nurturing employees’ potential is key for engaging and retaining them.

[03:40] The Future of Work is self-directed, which means a greater reliance on the human brain, not less.

[07:03] Future of Work transformation has just started -- we are going through the teething stage now.

[08:22] Ben has had a varied career which he describes it as a zigzag.

[10:25] Why was Ben’s first job at Enterprise the most fun job he had?

[12:49] Why did Ben launch his career coaching platform, Pilot?

[14:54] Most people do not feel powerful at work.

[15:34] How to make employee growth and development a priority, not a hobby.

[16:47] We need help to focus as the attention economy pulls us in too many directions.

[17:56] One size doesn’t fit all for work or careers.

[18:35] Coaching helps unlock people being able to advocate for themselves.

[19:36] How Pilot handles the diversity of work across industries, organizations, and people.

[21:30] How Pilot helped a top salesman not have to choose between his health or success.

[22:25] Pilot enables users to focus on what really matters in life.

[25:24] Ben has a holistic approach when it comes to growth and development, focused on addressing current dissatisfaction and growing where you are.

[26:43] The commonalities in how to manage yourself as a professional and ensure the employee experiences suits you.

[28:17] The benefit of personal agility.

[29:42] A college degree is no longer sufficient.

[31:37] What employees need to future proof their careers.

[32:55] Leadership is not a position.

[36:09] How to manage your own inclusion by decoding and explaining yourself to others.

[39:30] The intent to democratize coaching to support employees owning their careers.

[41:59] The strategic role of HR and their need for data is supported by the product’s design.

[43:02] Pilot’s initial non-enterprise version.

[44:45] What are some of the biggest misconceptions of coaching?

[48:17] Immediate Action Tip: Look at any frustrations as an indicator to take action, advocate for yourself and own your life and experiences at work.


“The Future of Work is self-directed”.

“Most people do not feel powerful at work.”

“The intent to democratize coaching.”

“People seldom regret speaking up and advocating for themselves.“

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