Episode 009

The Art of
Leading Creatives

with Todd Henry

Artwork by Ionut Caras

Perhaps the most challenging aspect of leading creatives is relinquishing control.

Creative professionals have success when they are in control, perfecting their craft to make great work. Yet, the best leaders are the ones who are humble enough to realize that their team members need the freedom and autonomy to take risks and grow. The trick is to lead with influence, to elevate everybody else’s game and inspire your team to do the best work of their lives.

But how exactly do you do that? How do you transition from a mindset of control to one of influence?

Today, Jeffrey sits down with Todd Henry, the founder of Accidental Creative and self-described ‘arms dealer for the creative revolution.’ Todd is an acclaimed author, international speaker and respected consultant in the realm of creativity, productivity and passion for work. Todd shares his experience as a ‘free-range kid’ growing up in a rural area as well as the health crisis that sparked his creative journey in music—and how those events shape his work today. He speaks to the idea of leading with influence rather than control and the reason why so many creatives resist leadership roles. Listen in for Todd’s insight around the leader’s aim to do the right thing—even when it’s difficult—and learn how you are a leader by virtue of putting creative work into the world.

Our Guests:

Todd Henry

Todd Henry is a foremost voice and authority on how teams and individuals can execute brilliant ideas every day. CEO of Accidental Creative and author of the books Herding Tigers: Be the Leader That Creative People Need (Portfolio 2018), Accidental Creative: How to Be Brilliant at a Moment’s Notice (Portfolio 2011), Die Empty: Unleash Your Best Work Every Day (Portfolio 2015), and Louder Than Words: Harness the Power of Your Authentic Voice (Portfolio 2015), Todd travels the globe like a creative arms dealer to equip people and companies with the right systems and habits that lead to everyday brilliance.

» toddhenry.com

Twitter: @toddhenry

Herding Tigers Giveaway

What’s your greatest challenge as a leader of creative people?

That’s the question that I have been living in since I first read Todd Henry’s new book, Herding Tigers. Now I’m inviting you to consider it with me – and sharing your answer could win you a copy of Todd’s book, Herding Tigers.

How do you enter?

  1. Write your response to this question in the form of a post on Instagram, Twitter, or Facebook: What’s your greatest challenge as a leader of creative people?
  2. Include a link to this episode of the podcast at trackingwonder.com/podcast/episode-009/
  3. Include the hashtag #creativeleaderTW

On Tuesday, June 5, we will randomly select three winners to receive a copy of Todd’s book, Herding Tigers.

This giveaway runs from Tuesday, May 29 – Monday, June 4 at 11:59pm ET.

Key Takeaways

[4:01] Todd’s young genius

  • ‘Free-range kid’ growing up in rural area
  • Exploratory play (i.e.: make movies in the woods)

[9:24] Todd’s transformation through music

  • Shy kid as high school sophomore
  • Infection led to two-month hospitalization
  • Wrote first song, performed in talent show
  • Pursued music through and after college
  • Learned tactics to capture audience attention

[15:17] Mortality as a source of inspiration

  • Difficult moments shake out of comfort zone
  • Must embrace change as nature of life

[17:38] How Todd become an intentional leader

  • Creative director for nonprofit in mid-20’s
  • Humbling challenge to lead people to best work

[20:31] The structure of Todd’s current team

  • Built on foundation of freedom as core value
  • Sales pipeline, literary agent to represent work
  • Partnerships for projects (i.e.: Herding Tigers Workshops)

[23:13] Why creatives resist positions of leadership

  • Tension between need to be liked vs. effective
  • Can BE both, but can’t CHASE both

[28:27] How to lead with influence rather than control

  • Leading with control compromises work
  • Equip others to make own decisions
  • Challenge team, give permission to fail

[34:31] The motivational archetypes

  • Builder, fixer and optimizer
  • Do best work when wired for task

[39:49] Todd’s insight around leading remote teams

  • Stop talking and start listening
  • Find out how team feels via process questions

[43:35] Todd’s view of the global leadership crisis

  • Leadership = doing the right thing without credit
  • Must be willing to make tremendous sacrifices
  • Requires mindset of service, aim to elevate team

[48:00] Todd’s take on accidental leadership

  • Cannot separate leadership from contribution
  • Creative work influences thoughts, actions

[51:13] What Todd is pursuing now

  • ‘Make things I love for people who love them’


Each week brings you in-depth conversations with leaders, stories from change-makers, and provocative ideas from artists and scientists – all designed to inspire you to shape your best work with more possibility, impact, and – yes – wonder.