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How a Chief of Staff Role Can Bridge the So-Called Generational Leadership Gap

Many HR executives recognize the corporate chief of staff as an important tool for supporting a top executive by keeping the executive focused on his or her highest and best use of time, by preventing negative surprises, and by working with the executive and leadership team to make and execute great decisions. More and more are recognizing that the chief of staff role solves problems from retaining high potential employees to filling the leadership pipeline and succession planning. Desda Moss covers these benefits in this SHRM HR book blog post. But, did you know that the role also offers an option for bridging the so-called generational leadership gap? Assessing whether a chief of staff can help – whether or not the answer is ultimately “Yes!” for your organization – can help you identify gaps in your current leadership approach or team so that you can start making plans to address them.

The problems

  • You’re trying to get an edge in the competition for talent. That shows up in hiring, sure, but it also shows up in the cost of people leaving your organization (estimates range from $5,000-$12,000 as the average direct cost of a single employee’s turnover).
  • There is some truth in the adage that people take jobs, but they leave managers. There are many reasons people leave jobs, of course, but people often cite a manager’s failure to support their growth in the organization as a reason they leave a role.
  • Several recent articles* outline the so-called leadership gap between older generations of leaders exiting the workforce and the up-and-comers taking their places. Part of this problem is the difference in the number of people in the different generations. Also, organizations have spent decades flattening middle management layers to save costs. There’s no ready crop of mid-level managers ready to step into more senior roles.

So, how do you not only keep your high potential employees but keep them engaged and grow them into the leaders your organization needs as it evolves? Put them in a chief of staff rotation.

How the chief of staff solves these problems

The chief of staff role offers a learning opportunity, access to the seat of power (in an organization and sometimes beyond), and a big challenge or sense of adventure to tackle.

The learning opportunity

The chief of staff role is most often a rotational position with a defined time limit. Because it pulls high-potential employees out of a specific functional role to support a senior executive, helps them learn about and participate in the whole business from that executive-level vantage point, and then places them “back in the organization” as a more senior leader than when they left their line function, chiefs of staff come out of the role with a broader, more strategic perspective. They are ready to fill leadership positions that they previously couldn’t have. It’s an accelerated, targeted, and cost-effective way to develop employees and improve knowledge transfer from one leadership generation to the next.

The “cool factor”

A chief of staff has access to the seat of power. How many people in your organization wishfully say, “If I just had 5 minutes with the CEO on the elevator, I’d tell him/her what I think or what’s really going on in this organization….” Well, the chief of staff gets that opportunity, every day. They also get to be a fly on the wall to behind-the-scenes conversations that others aren’t privvy to. They watch funny and sad stories unfold in real time that they can’t talk about at dinner parties but will always carry with them. They might accompany the principal on trips to cool venues they otherwise wouldn’t have taken.

The big adventure

It’s cool to be a chief of staff when things are going well; it can be super stressful when things are not going well. Regardless, some people thrive on the sense of adventure.

Chiefs of staff often field seemingly impossible or vague requests from their principal executive, and no matter how good they are at thinking ahead they can never fully know what’s coming next. One chief of staff in Seattle fielded a call from his executive one morning saying that his exec was in Los Angeles, bound for Korea on a flight that would leave in a little over 5 hours – but he had left his passport in the Seattle office. After teaming up with the executive’s EA to research options from couriers to charters, he found himself on a flight to Los Angeles with the passport in hand. (To his spouse: “Sorry honey, I won’t be around for the plans we made tonight.”) With moments to go before the Korea flight boarded, the chief of staff hand-delivered the passport to his executive, then turned around immediately and flew back. The circumstances could be just about anything, a PR response to negative press or that big deal that comes through and needs the exec’s signature just when the exec is in the remotest region of Kuala Lumpur. That sense of adventure – never knowing what’s next – is what keeps many people engaged.

These “big three” of the learning experience, the access to power, and the big adventure accelerate development and can tap into the various motivations of future leaders – often at the same time – and instill a degree of loyalty that leaves many chiefs of staff wanting to give back to the organization or exec who afforded them such an opportunity.

Lainie Heneghan, “Closing the Leadership Readiness Gap,” HR Magazine (Sept 23, 2015): https://www.shrm.org/hr-today/news/hr-magazine/pages/1015-readiness-gap.aspx

Theresa Minton-Eversole, “Concerns Grow over Workforce Retirements and Skills Gaps,” SHRM HR Topics & Strategy, Staffing Management Articles (April 9, 2012):

Brandon Rigoni and Amy Adkins, “As Baby Boomers Retire, It’s Time to Replenish Talent,” Gallup Business Journal (January 28, 2015): http://www.gallup.com/businessjournal/181295/baby-boomers-retire-time-replenish-talent.aspx

“Effective Knowledge Transfer Can Help Transform Your Bottom Line,” American Management Association (August 5,  2010): http://www.amanet.org/training/articles/Effective-Knowledge-Transfer-Can-Help-Transform-Your-Bottom-Line.aspx


  • 18 January 2017

By Tyler Parris

Tyler Parris is a Hudson-certified executive and career coach, former corporate chief of staff, and author of Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization. His career has spanned operations management at Intellectual Ventures, program management at Advaiya, Inc., technical editing at Microsoft, and computer networking in...


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I’d like to dedicate this article to the late Martha Birtles, former HR exec at HSBC, A few years ago, she suggested I explore this perspective on the chief of staff role, and this article began as an outline on the back of a napkin after that call.

Tyler Parris says:

What a nice dedication, Tyler, thank you so much for your contribution. We are delighted to have you!

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