Executive Director's Blog: To Understand Great Leadership - Eat Cake

This month I'm honored to share a guest blog post by Cathy De Rosa.  Cathy is a mentor, friend and one of the smartest people I know.  I hope you enjoy her thoughts on understanding great leadership.

How do we measure leadership? 

I am not referring to measuring a leader’s achievement against plans or goals.  I mean, how do we evaluate the act of leading?  Can we describe what great leadership looks like as it’s happening?

As the pace of change continues to accelerate at our organizations and across our campuses, most of us will serve in an organization or department “under new management” sometime in the very near future.  We may even be that new leader. 

How should we assess the performance or our new leader?  Of our own leadership actions?

The job description

Like many of you, I have read more than a few job postings seeking a new chancellor, president, dean, or executive director lately.  Is it my imagination, or are the postings getting longer?  It seems that we expect much more from our future leaders these days.  Based on postings published this month, we seek leaders who:

  • bring vision
  • are high-energy, passionate, and lead with integrity
  • are forward-thinking, innovative, and committed to perpetual improvement
  • will build momentum on ongoing initiatives and foster novel ideas
  • support collaboration and foster good governance
  • will be an ambassador and advocate
  • will strengthen diversity, inclusion, and mutual respect
  • bring a local, regional, and global perspective
  • will increase operational effectiveness
  • can advance fundraising initiatives
  • build cohesive and collaborative teams
  • are committed to learning, exploration, research, teaching, and entrepreneurship
  • are devoted to staff, student, faculty, stakeholder, and partner success
  • have a sense of humor.

There are no metrics provided, no yardstick suggested for measuring the minimum acceptable level of vision, passion, commitment, or global perspective.  Do we really expect our future leaders to excel against each attribute, or are we hedging our bets with these postings, hoping to find a leader who will succeed in any given scenario?

Leading in times of transition is challenging.  But very few leaders will deliver against every requirement on our growing list of qualifications.  So then, what matters most?

Speed, expertise, or something else

From the new leader’s first day, we are watching.  We are observing, learning, and of course, evaluating.  When will we know if we’ve made the right choice? 

Should we look for a fast start? 

Is a great leader the person who has the ability to get off the blocks quickly – making bold leadership moves in the first days or months?  Some leaders I know say that if a new manager doesn’t affect change quickly, s/he squanders a great opportunity.  A new leader enters office with a certain amount of “new leadership capital”.  Strong leaders spend that capital early to get things moving in a new direction.  They act.  Momentum begets greater momentum.  Great leadership is about taking action.

Or do we appreciate patience over speed? 

Are we watching to see if the new leader exhibits the qualities that we said we wanted in the job description?  Do we note if our leader is collaborative, builds consensus early, and strives to bring current initiatives to completion before starting something new?  One of the most experienced leaders I know believes that smart leaders take the first 90 days to learn and listen – they do not act.  Patience is great leadership (even if it is not listed in the job description).

Do we seek leaders who bring new proficiencies?

Are we looking for the new leader to quickly demonstrate their superior expertise in operations, scholarship, fundraising, or another functional area?  This requirement was clearly stated in the job description.  Great leaders bring something new to the organization.  Great leadership is building new competencies.  

Action, patience, expertise, or something else – how should we evaluate leadership?

A piece of cake

Let’s confess:  Few of us have a perfect track record for spotting great leadership when it enters our organization.  We do have high expectations.  But our expectations are quickly tempered by our concerns, even fears.  It’s not easy to forget those not-so-great new manager experiences.  We have a hard time being enthusiastic and cautious at the same time.  It’s hard for us to objectively evaluate leadership as it is unfolding.

While we may not recognize great leadership when it enters our organizations, I have come to believe that most of us recognize outstanding leadership when it exists.  

So if you want to understand what great leadership looks like, eat cake – or at least stand in the cake line at an admired leader’s retirement celebration and listen. 

When people wait in queue they talk.  It is a law of nature.  And when they wait in the cake and punch line at a retirement celebration, they talk a lot.  Next time you are waiting for your slice of the proverbial chocolate cake with vanilla “best wishes” icing, pay special attention to what you hear – and what you don’t hear.

What you won’t hear is much discussion about “Joe the collaborator” or “Barb the great fundraiser” or “Kate’s outstanding global, regional and local perspective.”

You probably won’t hear anyone speak about what the retiring leader accomplished in her first 100, 200, or even 365 days.  When it comes to leadership, days don’t seem to matter all that much.  But then again, you aren’t likely to hear accolades for leader Joe’s unbending patience or Barb’s “slow to make change” leadership aptitude either. 

I doubt that there will be much discussion of the departing leader’s specific operational expertise.  No one seems to recount a great story about stellar administrative skills. 

That “committed to entrepreneurship” job requirement might just come up in conversation.  People in cake lines do appreciate a leader who starts something new.  More correctly, staff appreciate a leader who helped them build something new.  It seems that staff like leaders who “start” things and then get out of the way and let the team run with it.

Most of the conversations will focus on the retelling of very specific events.  Many will be about a one-on-one mentorship moment with the leader – often over lunch, coffee, or during travel to a conference.  The leadership encounter will be a small part of a bigger story.  What happened after, or more specifically because of the mentorship moment, is the real story.  The promotion, achievement, or new career path will be center stage.  The protagonist is not the leader; it is the storyteller.

You will hear about the handwritten notes received or about the time when the leader showed up unexpectedly just as an important, non-work related event occurred in the staff member’s life.   

Vignettes will reveal how surprised a staff member was to discover that the retiring leader knew about a talent that had nothing to do with work – and how excited the leader was to celebrate their out-of-office success.

There will be humorous confessions of monumental failures and how the boss joined in the reconstruction efforts – and the ritual retelling in the years that followed.  But most of the discussion will be stories of achievement.  Our achievements.

What I have come to understand from my time in the cake line is that great leadership is not about leading; it is about preparing others to lead. 

Great leaders spend 80% of their time thinking about the people they lead, not about the things that they are trying to accomplish, or how fast or slow to act.  Great leadership is about making others successful. 

Leadership is the act of making teams better – one staff member at a time.  Great leaders act on this imperative on day one on the job, and on day 3,000.  It is urgent, and it takes patience.

So perhaps we can do our search committees a favor and help them draft the job description for our next leader. 

Seeking a leadership candidate who:

  • understands how to make others successful
  • has a sense of humor.

Cathy De Rosa is principal at CollegePatterns.  Cathy partners with libraries, colleges, and non-profit organizations to help them tell their story, grow new revenue sources, and develop future leaders.  Cathy can be reached at cathy@collegepatterns.com.


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