What CEOs need to know about Impossible Choices: 3 Lessons Learned When My Blog Went Viral

“You’re pregnant!”  I will never forget the joy of that moment when we learned we were having a baby.

Not long after, I found myself in a private meeting with then Mayor Michael R. White.  To my delight, he offered me the opportunity to serve as the Law Director of the City of Cleveland.  When we started talking a few weeks earlier about the possibility of this appointment to his Cabinet, I didn’t know I was pregnant.  Now, sitting in this stately office with this visionary, hard-driving Mayor talking about the career opportunity of a lifetime, I was about to have my very first courageous conversation about “work” and “life.”

I told the Mayor that I was honored to have the opportunity to serve, I appreciated his confidence in me, and that I would be thrilled to accept his offer, but I just found out I was pregnant, I did not believe the pregnancy would compromise my ability to serve him well in this post, I had every reason to believe that…. He raised his hand to silence me.  As I braced myself not knowing what to expect, he said, “That is wonderful news! You will be the second woman to serve as Law Director in the history of this city, and the first to give birth in office.”  I was stunned and jokingly responded, “I certainly hope not to give birth in the office!”  We both laughed and shook hands sealing the deal on our new partnership.

I served as Cleveland Law Director for 5 years – through my pregnancy, birth of my daughter (not in the office!), death of my husband 13 months later, transition to my new life as a widowed, single mom, and my very difficult decision to resign at the end of the Mayor’s second term of office when my daughter was 4 years old.

Looking back on that moment over 22 years ago, I know how fortunate I was that my first conversation with a CEO about “work” and “life” went so well.  I know that this isn’t as common as it should be from my own experience and the reactions of working parents to my first viral blog post, “Decisions I Don’t Regret – One Parent’s Take on Impossible Choices,” www.sheinthecle.com.

Yesterday, I shared 3 lessons I learned as a parent from the overwhelming reaction to my blog post.  But the many comments, shares and conversations on social media and directly with me also have shown valuable insights that CEOs need to hear.

So, this post is directed to those top leaders – CEOs, executive team members, senior managers – that are in positions to influence, impact and lead change in workplace culture right now.

Here are my 3 lessons about impossible choices for you:

  1. We should be laser focused on results, and more flexible about how we get there

“Our editors were all cheering you on as we read your article (and I am typing this from Chuck E. Cheese).” –Allison Slater Tate, freelance writer and editor for TODAY.com and NBC News.com.

The reaction to my blog validated what we have all known for decades.  Of the many reasons our team members are forced to make impossible choices, one tops the list – inflexible work schedules.  We are accountable to deliver excellent and timely results for our customers and value for our shareholders.  No one is asking us to compromise on that.  The conversation our team members want to have with us is about when and where their work gets done – the means to that end.  And what most of them want to talk about is “a bit more flexibility,” like Jean:

“I have been trying to get my employer on board with flexing my schedule to help my two children one with significant disability, so far no luck. I have been able to block my schedule occasionally for school events so that is a blessing. I just need a bit more flexibility with therapy etc. Thank you for the article I will be sharing.” – Comment by Jean on SheInTheCLE.com, May 12, 2016

Even when they’re talking about “a bit more flexibility,” it’s not an easy conversation to have with us.  Most workplaces dictate a rigid work schedule, so asking for flexibility often feels like asking for a favor or special treatment to get their work done.  It broke my heart to read this comment from Julie:

“But I do realize what’s important to me and I won’t miss any of their school events or when they are sick I’ll be home with them and you certainly just made me feel like what I’m doing is ok – it’s not perfect but you can still work and be involved in your children’s life. They mean the world to me, they are my life and I work for them not because I love my job to be honest. I wish my employer was a bit more flexible but I’m doing my best. My problem is I’ve wanted to ask to work from home 1 day a week but my boss I don’t believe would be welcome to it as she’s been with company for 30 years. Any advice?”– Comment by Julie on SheInTheCLE.com, May 12, 2016

As a CEO, I have tried to accommodate requests for flexibility when asked.  Why? I know that affording a bit of flexibility at work deepens commitment to the success of our organization.  I believe in my team members and their passion and ability to get results without rigid rules and directions from me on how to get there.  I trust that they would not make the difficult request for flexibility if they didn’t truly need it.

In my story, I was able to contribute to a successful result but did it in a different way than requested – a way that satisfied my responsibilities at work without sacrificing my time with my daughter.  Some have reacted to my story by saying that they’re glad I had the flexibility to choose my daughter over my work that day, but they don’t have that option in their jobs.  I recognize that not every job can be done off-site or during modified hours, but there is room for a bit of flexibility in every job.  We find our way there by staying focused on results and what our team members need to get us there.

  1. An investment of guilt-free flexibility can yield remarkable returns

In a world of choices, being good to your employees is one that too many employers see as “costing” them, but I tell you that this builds loyalty in your team…and a happier parent is definitely going to be a more productive employee!” – Comment by Toni Neary on SheInTheCLE.com, May 18, 2016

There is remarkable, often untapped, return on investment (ROI) in a little guilt-free flexibility at work.  For me, it was all about supporting my choices to be there for my daughter.  For others, it may be affording them the time to spend with a loved one at critical point in their life.  When Dawn Kendrick came to interview me, she immediately shared her story about when her father became very ill, just as she was starting her current job over a year ago.  She could not hold back her tears as she recounted how her current employer made it possible for her to be with her father during his final weeks and days completely guilt-free.  She so cherishes the memory of that time with her dad.  When I asked her how it made her feel about her current employer, she responded without hesitation, that because the company was there for her when she needed their support and understanding, “I would do anything for them!”

Morton Mandel, a successful business and civic leader, mentor and friend, taught me a lasting lesson about being a CEO with just one question.  He asked me, “What do you think about when you are driving home after work each night?” I started to respond by saying that I think about all the work I didn’t finish and all the work waiting for me the next day, but he cut me off.  “Wrong, wrong, wrong!” he scolded.  “You should be thinking about one thing and one thing only – the players on the field.”

What I learned that day, and try always to remember, is that my job as CEO is to take good care of the people that take care of my customers – to make sure they have what they need to be successful – because they are the ones that get the work done.  The company and I will be successful only if they are successful.

Loyalty, creativity and motivation to do what it takes to get the job done well dramatically increase when we honor and support a team member’s desire to live an authentic life – a life that reflects her values at home and at work.  This point was well-made by one of the most loyal and engaged members of my former top team in her comment on the blog:

“The best part of this story is that Sharon walks the talk! I joined her team at The Centers 9.5 years ago. I was only with the agency for 8 months when I got the call of a life time, to be the foster to adoptive mom for my angel on earth Kiara. Not only did Sharon offer guidance and support during my family leave, she understood that family time was as important as the critical work we were doing on behalf of this community. She did not once call me during my family leave time to discuss work. When I called into work during this leave, her mantra was always ‘We miss you but enjoy this family leave time.’ No guilt about all the extra work she and others were doing during my absence.  Sharon is the real deal! She understands and respects that working parents have a hard balancing act between work and family. Each of us must walk the talk and support staff that are daily facing tough decisions balancing work and family. And we need be gentler to ourselves as parents. Lastly, let’s make system changes -take the courage to change HR policies so all staff at all levels can be his / her best at work AND at home.” – Comment by Bernie Kerrigan on SheInTheCLE.com, May 13, 2016

Our team members want us to see them for who they are – whole people!  For many, that is both a devoted parent striving to do meaningful work and a dedicated professional aspiring to live a good life.  They so crave this from us that, when they hear a story about a CEO that does, they share it!

  1. Flexibility is the key to winning the war on talent

I gave your blog to my HR Director and told her this is the kind of company we need to be.” – Comment by Managing Director of National Investment Banking Firm at an event to me, June 15, 2016

My work and passion have focused on leading innovation inside large private and public sector organizations – intrapreneurship that happens inside our large organizations where much of the resources, talent and influence to make real change at scale reside, as opposed to entrepreneurship that happens outside them.  The unfortunate reality reflected in the reactions to the blog and my own experience is that impossible choices are causing too many talented people to opt out of our organizations.  They often leave to start their own businesses or to find other ways to do good work and create the guilt-free flexibility they need to live good lives.

When innovators opt out because they can’t reconcile work with life, the rest of us lose.  Joanna Barsh, director emerita for McKinsey & Company and author of Centered Leadership says, “Flexibility will become the norm for employers who want to win the war on talent.”  Fast Company recently reported about a new study by career site FairyGodBoss that shows,

“…after compensation, flexible hours trump every other factor when women are deciding on a job offer, regardless of their age or whether they have children. A recent study by McKinsey & Company finds that millennials of both genders are more likely to accept a job offer from a company that offers flexible work schedules.  Yet what drives most company’s recruitment efforts is demonstrating that it’s a “cool” or “fun” place to work. Instead of investing in ways to innovate flexibility, many companies are still spending money on foosball tables, onsite yoga, and free food.”

It is easier to manage a team with rigid work rules – if your end goal is predictability, accountability and compliance.  For those of us desiring so much more – engagement, creativity, inclusive innovation, growth, profitability – we need to be smart about how we attract and retain the very best people at all levels of our organizations.  They are telling us the key is flexibility.  It’s time for us to listen.

I’ve learned so much from the thoughtful conversations my story has inspired.  I appreciate the opportunity to share these lessons with other top leaders in positions to influence, impact and lead change in workplace culture right now.  I hope you will share your feedback with me.



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Sharon Sobol Jordan

Sharon is trying to make the world a better place for as long as she is in it. She is a devoted mom that strives to do meaningful work, and a dedicated professional that aspires to live a good life. Sharon is drawn to opportunities to work with others to create large scale, systems-level change that will last. She believes that every one of us can change the world in big and small ways when we are inspired and have someone that believes in us. She is inspired every day by her daughter, and does her best to pay it forward to others. When she is not working to change the world, Sharon enjoys every moment she spends with her daughter, traveling, taking photos, hiking with Dave and Charlie, and connecting with family and friends.

7 CommentsLeave a comment

  • My Dear Sharon…

    What a great human being you are…how great it is to have you as my friend and former colleague. I continue to wish you all the best in all that you do. You’re right, probably best you didn’t have the baby in my office…very difficult to explain to City Council and the PD…and they said I didn’t have a sense of humor!


  • This is a great blog — and fantastic for organizational leaders to read. As managers, it’s easy to forget that we are managing individuals, not groups. Each person is on their own journey and has different things that inspire them and help them succeed. Sharon, when you were my boss, you completely got that about me. And I learned how to manage better from you. Hoping that more and more organizations can focus on the results, and certainly not on the process of how (or at what time of the day) they achieved those results. Thanks for another great blog!

    • I have always valued and enjoyed our working relationship and friendship, Amy. Love how you are paying it forward, and grateful that we continue to find new ways to partner on this journey.

    • I learned from the best! So grateful to you, Lee, for your visionary leadership and friendship.

  • Sharon, thank you so much for sharing your story from both lenses: as a parent and as a CEO. I think it’s so important for people to hear that you can give AND take guilt-free and be enormously successful (and happy)! I hope your testimonial reaches far and wide to change work culture for parents across all levels and roles.

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