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Transform Your Leadership in 2020: The 5 Most Important Questions to Ask Yourself Now – Sherri Hilton MAL, CEC, PCC


The Leadership Series

by Sherri Hilton  MAL, CEC, PCC

It’s 2020!

Officially the start of a New Year and a new decade. Full of the promise of new beginnings. A new you. And for many with whom I’ve spoken, an opportunity to set new goals and resolutions.  Truth be told, I’ve never been a fan of New Year’s resolutions. I think it’s a lot of pressure to set big and sometimes unrealistic goals, often too many at the same time and many of them doomed to fail within the first 30 days. The dismal numbers of fitness memberships that are purchased and not used after the first month of a new year reflect that. We find ourselves floundering in action items, forgetting why we felt compelled to commit to that goal in the first place, losing our focus and well, feeling like a failure when we don’t achieve those big goals. I say get off the big resolution, big goal treadmill and instead get clear, inspired, purpose driven and intentional with these five questions that will help transform your leadership in 2020.

1. What really matters to me and why?

I believe this is THE most important question to ask yourself and to ask it often. How we spend our days is ultimately how we spend our lives. What energizes you and compels you to take inspired action? Are you leading yourself and others from a place of creativity and purpose? Do you focus on taking action in service to what you want to create and have in your life? Can you say right now that you spend the majority of your time with the people who matter most to you and on the things you truly care about? Ask yourself, what really matters to you?

2. How do I want to grow in the year ahead?

In my experience as a leadership coach, and having worked with leaders in a wide range of industries, the best leaders are the best learners. They are curious, open minded and hungry to evolve, not just as leaders, but also as human beings. They devour books, have conversations with diverse thinkers, try new things and reflect regularly on their leadership and their impact. They aren’t afraid to ask for and act on feedback and ask questions rather than give answers all of the time. So get even more curious. Read something provocative. Ask more questions. Ask different questions. Step out of your comfort zone. Do it often. And listen more.

3. What impact do I want to have in the year ahead?

Look not only inward at yourself, but at the same time look outward and beyond  to your communities and your world.  Asking yourself how you can contribute to making this world a better place, not just for now, but for the future, is critical to transforming your leadership. What is the positive difference you want to make in the year ahead? In the lives of others?  I like to think of it as the question that asks, “long after I’m gone, what will continue to live on from my work and what I spent my time on and will continue to make a positive difference to the world?” Even the smallest actions that we take from a place of purpose and intention can impact far beyond what we see and know.

4. What ONE BIG THING do I need to focus on to make the biggest positive difference to my leadership in 2020?

It can often feel like there is so much to think about, focus on and do, however if everything is important, then nothing really is. Decide what behavior or action will have the biggest impact on your leadership. Ask yourself how and why it will be a game changer for you, and then make it a priority.  Don’t be afraid to get creative with how to continually remind yourself of your ONE BIG THING (I am a fan of notes, post it sayings, calendar reminders, etc.) Ask for or get help if you need it (delegate more, get a coach, set boundaries.)  Remember, changing behavior or making changes is rarely easy, always possible, and critical to your growth as a leader.

5. What do I need to let go of?

In my work with leaders, I often observe that letting go is just as important as starting something new if we want to move forward with clarity and intention. This can look like letting go of an underlying belief that keeps us stuck in a reactive cycle of behavior, an outdated mindset that keeps us closed off from thinking differently or being open to new ideas or ways of doing things, or a personal narrative that keeps us playing out unproductive patterns of behavior.  Just as important as clarifying what you want to focus on is identifying what is holding you back or in your way and what you might need to consider letting go of.

So grab that notebook, journal, laptop or whatever inspires you to pause…take a breath, reflect and write on these 5 questions.  Yes, writing increases neural activity in certain sections of your brain, sharpens your thinking, and helps you learn and also allows you to revisit your thoughts.  Examining these 5 questions will allow you to take the first steps to transforming you and your leadership in 2020.

About Sherri Hilton

Sherri Hilton is the Manager of Leadership with a North American based energy company and also a private leadership coach for leaders in both the United States and Canada.

Sherri has a proven track record of helping leaders achieve personal excellence, build strong relationships with others and positively impact and contribute to the success of their organizations.  As an experienced and highly skilled executive coach, Sherri has worked successfully worked with senior and high potential leaders, business owners/entrepreneurs and upwardly in a wide range of industries and professions including energy, finance, legal, healthcare and construction to name a few.

She has more than 20 years of experience in individual and group coaching, leadership development, advanced facilitation and public speaking.


Sherri has both a Masters degree in Leadership and a Graduate Certificate in Executive Coaching from Royal Roads University and holds a PCC level of accreditation through the global International Coach Federation (ICF), in which she is an active member. She is also certified in a number of leadership development assessments and tools, including Emotional Intelligence 360, The Leadership Circle 360, MBTI, Korn Ferry Voices 360 and Personality Dimensions.

Join Sherri at on Linkedin at Sherri Hilton Linkedin


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