“How can I make your life easier?”

Guest Post by Debi Wolfe

“How can I make your life easier?”

That was the question one of my leaders used to ask me at the end of every one/one for over a decade. We caught up recently and he wrapped up our lunch conversation with this question. It made me smile and got me thinking about leadership impact and legacy as a result of asking questions.   There was a lot of intention behind this simple and memorable question.  It was not about helping me have a “cushy ride” or letting me abdicate responsibility. This was a servant leader question packed with meaning.

Questions behind the question:

1 – Do you have clarity? (Role, expectations, priorities, results, etc…)
2 – What resources are needed to accomplish what we are asking of you?
3 – What obstacles can I help remove to ensure you achieve your objectives?
4 – What information do you or others need to move things forward at pace?
5 – What distractions are diluting your focus?
6 – What is your opinion on ………?
7 – How can I get out of the way so you can fly?
8 – Where do you need my advocacy?
9 – Do you feel valued and recognized for your contributions?
10- Are you having fun? Have you celebrated your wins?

It turns out, these questions are rooted in key foundational leadership principles that inspire trust, teamwork, confidence, commitment, growth, impact and loyalty. All of which are valuable in building the next generation of leaders.

Several years ago, I heard a speaker talk on leadership and he said something I will never forget.  “Leaders will be known for the questions they ask and those questions tell their people what is important and will drive behavior”.  

What questions are you asking your teams and what message is it delivering?

Who has been a legacy leader for you and what have you admired about them that you want to emulate?

Debi Wolfe


Debi Wolfe is a dynamic C-suite executive and entrepreneur.  Debi is a contributing writer for Forbes HR Council, has appeared on Bloomberg TV and been profiled in Entrepreneur Magazine. She has been a guest lecturer at University of South Florida speaking on entrepreneurship.  Debi was recently recognized as Staffing Industry Analyst’s Global Power 150 Women as well as DE&I Influencer.  She was awarded Tampa Bay Businesswoman of the Year. In her personal time, Debi is deeply involved with orphan care and education in Malawi, Africa and Thailand.


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