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9 Questions to Ask When You’re Looking to Land a Creative Leadership Role

“Are you a leader?” creative coach Tina Essmaker asked the crowd.

There was a brief hush as everyone considered this. At the very first session of a major conference like HOW Design Live, there’s always an incredible energy in the room. Some people are filled with excitement and possibility and can’t sit still. Others are anxious—and they can’t sit still, either, wondering, Did I make the right decision by making the investment to come here?

Regardless of which group everyone fell into, they soon knew they were exactly where they should be, as Essmaker gave them the tools to plot their own creative futures.

Read on for some of those very tools from Essmaker’s session at HOW Design Live 2019.


Tina Essmaker began her career as a social worker, and then co-launched The Great Discontent magazine. But after a while, she was burned out. She realized she was living a reactionary life. She decided she needed to take action. So she did.

As she said in her HOW Design Live Creative Leadership session, “We are all capable of leading, but before we can lead others, we must lead ourselves. Leadership begins with what already is, who you already are, and what you already have. Leadership begins with you.

She then shared some of the big questions she asked herself back then, which she uses today with clients in her coaching practice for creatives:

  1. What brings me satisfaction in my work?
  2. What are 3-5 North Stars that guide me home and fulfill me? (Essmaker’s included “growth,” “independence” and “creativity.”)
  3. What do each of these words mean to me—and how do I want them to manifest in my work life?

After, she suggested digging a bit deeper:

  1. What does my typical day look like right now? How do I feel during the day?
  2. What does my ideal day look like? How do I want to feel during the day?
  3. What one thing can I do in the next week to get closer to my ideal day?

Essmaker uses her mornings for deep, focused work (and puts her phone in Airplane Mode), saving the emails and calls for afternoons. She advises scheduling one day a week with no meetings; one day a month to be offline with no screens.

As you go along, she said, you can then begin to ask the bigger questions:

  1. What career/business goals do I want to achieve this year?
  2. What actions will I take to meet each goal?
  3. What are my yearly goals that I can break into quarterly milestones based on priority?

When you put the time in on these questions, she said, your work, life and perspective shift. And people begin to look to you for leadership—regardless of title. And that’s the key: You don’t have to wait until someone says you’re a leader to become a leader.

In other words: Leadership begins with you.

Essmaker’s session was an empowering and actionable start to the HOW Design Live universe—and served as a great preview to the life-changing sessions that would follow.

Join us in Boston in 2020 to begin your own journey. Registration will open in September, so be sure to check out our pricing and save May 4th–7th for our 2020 conference. We can’t wait to share all the extraordinary things we have in the works—and how they, too, will take your career and craft to the next level.