Remote Leadership and Sharpening the Saw - Jay Millen

4 min readJan 10, 2023
Remote Leadership and Sharpening the Saw — Jay Millen

The challenges of leading a modern organization and maintaining or developing a team culture have never been greater than those we face in the current pandemic world. The old adage “Out of Sight, Out of Mind” is a warning for what we have been dealing with now for more than 2 years.

Early attempts to maintain engagement through zoom and video conferences often led to team and individual fatigue as they could drone on with a broad audience and unclear agenda. Additionally, not everyone has a remote work space or 5G internet connection facilitating this type of effort and technology glitches led to some frustration all around.

There also became a “two class” system as defined by governments of essential workers and “all others” creating a further separation in many businesses and institutions. Coupled with fear and uncertainty in the early stages and false promises of a quick return to normalcy many of our team members became frustrated and cynical not so much about our businesses, but more about how to balance work from home, educate their children remotely, and take care of aging parents or grandparents in isolation.

Given this we shouldn’t be surprised as leaders that we face a real challenge in getting team members reinvigorated and reenergized about their work and the role they play in our organizations. Just like with covid, while there is no magic cure, there are some common sense actions and operating rhythms we can develop to get team members reengaged and moving forward as we turn in another direction through this stage of the pandemic.

  1. At your next all hands meeting or corporate “broadcast” start with reminding everyone what the essential purpose of your organization or business is. As an example for me at Caldwell Partners in my most recent team session I started with our purpose: To provide clients with access to differential world class talent to meet their leaderships needs and give candidates their next great career opportunity in a culture that fits both.
  2. Talk to your direct leaders and staff 1:1 for just 10 minutes once a week as a “how are you doing” check in — no agenda just a check in — and have them do the same with each of theirs.
  3. Have a once a month live or remote “social hour”; coffee and breakfast, a lunch (send takeout if remote) to stay connected on key issues team members are having with customers, suppliers, each other; don’t let the frustration come to a boil
  4. Keep a positive outlook — be transparent with challenges but show a can do attitude and share monthly or quarterly results and metrics “live”
  5. Limit formal videos or sessions to 1 hour full stop. If you have more material than that break it into 2 or 3 parts with 30 minute breaks in between. Keep the entire session less than 3 hours with breaks. Attention spans and attitudes degrade significantly after 20–30 minutes via video, and diminishing returns get ugly.
  6. Finally, Encourage teams to begin socially distanced live meetings, routine social events or dinner together if appropriate, and plan for a “turn the corner” celebration — date unknown but event certain ! Create an anticipation for something fun to look forward to.

These can all survive as potential best practice for communication and connectivity post pandemic or may change dramatically dependent on what your “normal” live team vs remote workforce model is. Most importantly if you haven’t already started moving in this direction, now is the time. Let me know how your team responds and please share your own best practices that we can share across the community.

Stay safe and stay engaged.

Jay Millen




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