5 Questions Millennials Must Ask to Become Successful Leaders

By December 3, 2014Millennial

There will come a point in time in every Millennial’s career when we move from being primarily executioners to leading teams and managing others. That’s a shift I often looked forward to in the day-to-day grind of being on the front lines of production. However, as I’ve started making that transition in my own personal career, I’ve definitely learned the truth behind the idea that “everyone thinks leadership is easy until you become one.”

I’ve had to face some challenging questions for the first time…

How do I move from a “doer” role to a “manager” role? How do I change my mindset to effectively move from “hands on” role to one of directing and overseeing a team?

The short answer is… it’s not easy. The paradox I’m learning is that answering those questions begins by asking another set of questions.

become successful leadersThe Higher You Go, The Harder it is to Define “Success”

When we start our careers in more of an execution type of role, it’s easy to earn our stripes by what we can do. As we grow and get promoted, we start to get paid less for what we can do and more for what we know. The higher we go, the less defined our job description becomes. Our success depends on our ability to make other people feel powerful to get things done.

However, we still need something we can measure our work and effort by at the end of the day. That can be a challenge when our entire lives have been measured by meeting deadlines, cranking out projects. There’s definitely a mental shift that needs to take place.

5 Questions Millennials Must Ask to Become Successful Leaders

How can Millennials know if we’re being successful as we make the transition from doers to leaders? Here are 5 questions we can use to measure our efforts to determine, “Did I do what a leader should have done today?”

  1. Am I asking the right questions? Successful leadership isn’t about having all the answers; it’s about being able to find them by asking better questions.
  2. Am I listening for the best answers? We all know what it’s like to work for “know it all leaders.” The only way to avoid this is by disciplining ourselves to listen to the ideas of others.
  3. Am I taking time to think about our biggest problems and opportunities? This can feel weird, especially if we’ve been primarily in a “doer” role. It can feel lazy. However, this is an essential part of leadership. It’s the leader’s responsibility to look up and ask, “Are we even on the right road?”
  4. Am I effectively communicating the plan to our team and setting expectations? Successful teams are built on clear communication and direction. If we don’t communicate the plan or set expectations, we force the team to make assumptions.
  5. Am I stepping back to evaluate the strategy and observe the impact? Evaluation and experimentation are two words that are an essential part of leadership vocabulary. Are the things we’re doing working? Is our hypothesis right? Are the things we’re doing moving us closer toward achieving our goals? These are the types of questions leaders ask.

A Word of Encouragement for My Millennial Peers

Stepping into a leadership role for the first time isn’t easy. It’s a big shift from where we’ve been.

  • Do your best.
  • Be Yourself.
  • Don’t be afraid to say, “I don’t know.”

You’re not in leadership because you have all the answers; you’re in leadership because you’re going to help solve problems. My hope is that after a couple of years of doing it, leading others will feel as natural for us as putting our clothes on in the morning.

What questions do you ask to ensure you are becoming a successful leader?

Jeremy Chandler

Jeremy Chandler

Jeremy Chandler is a 20-something who loves coming alongside other Millennials to navigate through the topics of leadership, career development, and personal growth. He currently lives in Nashville, TN and jumps at any opportunity to connect over coffee.
Jeremy Chandler
Jeremy Chandler

Join the discussion 6 Comments

  • Paul Horne says:

    Some good thought. Thanks for sharing.

  • Alli Polin says:

    Great questions, Jeremy! I’ve also found that for many people stepping into leadership they need to ask themselves: 1) Am I playing favorites? and 2) Am I working so hard not to play favorites, I’m doing damage? It’s hard to ease into a new leadership position!

    I can still remember when I first made the leap and my old team and friends went out to lunch and didn’t include me. I get it, but ouch. Not to mention that I was still figuring out who I was with my new title. Turns out, like you wrote, I was still me.

    Thanks!

    • Jeremy Chandler says:

      Those are some really great points, Alli! One thing I’m learning is that it’s definitely not easy, but that it is totally worth it.

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