In Conclusion: Transitioning from a Bossy Boss into a Digital Age Leader

In this 8th and final installation of an 8 part series, Brad Szollose and Rob Hirschfeld invite you to share in our discussion about failures, fights and frightening transformations going on around us as digital work changes workplace deliverables, planning and culture.

We hope you've enjoyed our discussion about digital management over the last seven posts. This series was born of our frustration with patterns of leadership in digital organizations: overly directing leaders stifle their team while hands-off leaders fail to provide critical direction. Neither culture is leading effectively!

Digital managers have to be
two things at once

We felt that our "cultural intuition" is failing us.  That drove us to describe what's broken and how to fix it.

Digital work and workers operate in a new model where top-down management is neither appropriate nor effective. To point, many digital workers actively resist being given too much direction, rules or structure. No, we are not throwing out management; on the contrary, we believe management is more important than ever, but changes to both work and workers has made it much harder than before. 

That's especially true when Boomers and Millennials try to work together because of differences in leadership experience and expectation. As Brad is always pointing out in his book Liquid Leadership, "what motivates a Millennial will not motivate a Boomer," or even a Gen Xer.

Millennials may be so uncomfortable having to set limits and enforce decisions that they avoid exerting the very leadership that digital workers need! While GenX and Boomers may be creating and expecting unrealistic deadlines simply because they truly do not understand the depth of the work involved.

So who's right and who's wrong? As we've pointed out in previous posts, it's neither! Why? Because unlike Industrial Age Models, there is no one way to get something done in The Information Age.

We desperately need a management model that works for everyone. How does a digital manager know when it's time to be directing? If you've communicated a shared purpose well then you are always at liberty to 1) ask your team if this is aligned and 2) quickly stop any activity that is not aligned.

The trap we see digital managers who have not communicated the shared goals is that they lack the team authority to take the lead.

We believe that digital leadership requires finding a middle ground using these three guidelines:

First: Clearly express your intent and trust, don't force, your team will follow it.

Second: Respect your teams' ability to make good decisions around the intent.

Third: Don't be shy to exercise your authority when your team needs direction  

Digital management is hard. You don't get the luxury of authority or the comfort of certainty.

If you are used to directing people then you have to trust yourself to communicate clearly at an abstract level and then let go of the details. If you are used to being hands-off then you have to get over being specific and assertive when the situation demands it.

Our frustration was that neither Boomer nor Millennial culture is providing effective management. Instead, we realized that elements of both are required. 

It's up to the digital manager to learn when each mode is required.

Thank you for following along. Rob and I always have fun with these and we look forward to the next series...

Until then, enjoy the Digital Age. It's been an honor.

Rob and Brad

PS: If you are interested in book Rob or Brad or both for a panel or workshop on Management & Motivation in The Digital Age, Click Here to contact us.

Our point of view: About the authors

Rob Hirschfeld and Brad Szollose are both proud technology geeks, but they’re geeks from different generations who enjoy each others perspective on this brave new world.

Rob is a first-generation Digital Native. He grew up in Baltimore reprogramming anything with a keyboard—from a Casio VL-Tone and beyond. In 2000, he learned about server virtualization and never looked back.

As founder and community lead of the OpenCrowbar project, Rob is the CEO of RackN, which provides support, consulting and commercial extensions to the community project. 

Rob is also a board member for the OpenStack Foundation. A position he was elected to fill in 2012, 2013 and 2014 and the chair of DefCore committee.

Brad is a Cusp Baby Boomer who grew up watching the original Star Trek series, secretly wishing he would be commanding a Constitution Class Starship in the not-too-distant future.

Since that would take a while, Brad became a technology-driven creative director who cofounded one of the very first Internet agencies during the dot-com boom. As a Web pioneer, Brad was forced to invent a new management model that engaged the first wave of Digital Workers.

Today, Brad helps organizations like Dell and MasterCard close the digital divide by understanding it as a cultural divide created by new tech-savvy workers ... and customers.

Beyond the fun of understanding each other better, we are collaborating on this 8 part blog series for different reasons.

• Brad is fostering liquid leaders who have the vision to span cultures and to close the gap between cultures.


• Rob is building communities with the vision to use cloud products that fit the Digital Native culture.