By Molly Rudberg, Executive Coach and Leadership Expert

Many retrospectives of 2020 invite us to ask, “Other than that, how was the play, Mrs. Lincoln??” Last year was most definitely not business as usual.

That said, my clients displayed incredible resilience and readiness for change in both their business and personal lives. And in many cases, those changes had a direct impact on the bottom line for their organizations.

Here are three areas where I saw (and highly encouraged) leaders at all levels to raise their game in 2020 and beyond:

Well-being actually matters.

My usually hard-charging, type-A clients found themselves being forced to slow down and cultivate relationships with their people last year. The command and control, the default style of “What does the Operating Plan tell us to do??” just wasn’t gonna cut it in a world where business was virtual, COVID could close an office at a moment’s notice, and they were having to rely on their 14-year old to set up Zoom.

Old school leadership tended to be transactional because it could be. 2020 style leadership required leaders to slow down and tend to a whole new set of wellbeing challenges they didn’t budget or plan for (physical, mental, emotional, financial, relationship, and spiritual). Turns out, maintaining productivity in a world where so many employees work from home requires a great deal of paying attention.

In my business, we call this “being in a relationship” which is just a fancy term for “spending the time to get to know people and genuinely empathizing with them”.

And honestly, the adaptations to this new way of relating were pretty brilliant.

Understanding that employees were nearing burnout (increasing number of hours in meetings via zoom to prove value sans in-person face time for example) a CEO I work with declared Tuesday and Thursday afternoons as “Meeting Free” allowing folks to focus on their actual work as many voiced frustrations their days had become back to back Zoom calls.

She also mandated a Friday monthly “Wellbeing Day” where everyone was required to take the day off and tend to their health. It’s now officially part of their benefit plan as morale increased significantly with its announcement and practice.

I have another client who keeps a list of her direct reports (25 total) and checks in with each of them, 1:1 every week to see how they are doing and if they need anything. Not related to work – strictly about their wellbeing.

If you are waiting for HR to tell you that you’ve got significant morale problems, then it’s already a way bigger problem than you imagine.

Flexibility and Reinvention are the new normal.

To see a Zoom meeting of 9 people go horribly wrong is, perhaps, one of the most common shared business experiences of the past year. It is also one of the most hilarious… if it’s not your meeting.

Take all of the usual issues that come up in any enterprise, then layer on top of that Wifi going out, screaming kids in the background, cats with a destructive keyboard habit, on top of employee stress as clients bailout of contracts and you have a recipe for chaos.

Those of us “in charge” have a deep need to control as well as lead (yes, they are different). When everything goes to hell, it’s very tempting to try and assert more control rather than “being like water”, flowing around the obstacle, and helping everyone move forward. This was especially challenging for leaders who are data-driven. What’s the best practice for Zoom set-ups and managing an increasingly unknown set of outcomes? How do you answer the question “When will we be back in the office (over and over and over)?”

The leaders I worked with last year worked diligently to reshape their notions of control. Rather than focusing on what they didn’t know and couldn’t know, they honed in on the core principles of shared enterprise that they knew would have a positive effect.

One CEO client accepted early on that remote work is here to stay and announced a Manager of Remote Work position. The position will focus on making sure the org is hearing from and delivering to their remote employees what they most need and want from company culture. In the space of not knowing exactly what this will look like completely – he decided based on feedback. This was a stellar example of committing to the new normal and running with it.

Another CEO client found himself irritated at the increasing pace of “are we there yet??” questions from his team during regular office hours. How was he supposed to know when they would reopen? Or how a pandemic would impact healthcare plans? And business goals? And the upcoming scheduled happy hours and annual holiday event?

At the end of his rope with frustration, I asked what might be possible if he shared his own fears, concerns, and COVID ups and downs at the next Company All Hands. Followed up with a request from the team for support. (In my world, we call it “vulnerability”. Choose whatever term you like.) He was reluctant at first… but ultimately took the swing.

And… the outpouring of response was surprising and gratifying. Employees not only wanted to support him, but they were also passionately concerned about supporting the entire organization. How could they play a role in making him and the organization thrive during this challenging time?

In 2019, this would have been seen as some feel-good, woo-woo move. In 2020, it was a crucial step in gathering his people to move forward together.

Inclusion and Belonging matter more than ever.

Diversity and inclusion have been significant issues at many companies. Getting the most from every employee is of passionate interest to all of my C-suite clients.

Making work remote meant that employees on the margins (whether for cultural, personality, or other various reasons) were more vulnerable than ever to see themselves as outsiders. Taking away the cultural bedrock of daily interaction meant that every team member was asking to be seen, respected, and supported more than ever before.

One CMO I partner with created a weekly stand-up for her team to gather and publicly acknowledge good works that had been done over the week. Only 10 minutes long – each person is to come prepared with some sort of detailed acknowledgment of someone else on the team. This does double duty by celebrating individual team members and making team members grateful for one another.

Another senior leadership team I coach chose to model belonging by going on a company “Listening Tour” with the intention of learning about employees in different roles/levels. A daunting task, yes… but modeling that every voice is important and there is a commitment to listening and building relationships outside of just doing our work.


In short, every organization is the product of its shared experiences. Prior to “Life During the Plague”, it was too easy to let the collected inertia of culture move us along. Once the equilibrium shattered, leaders had to make the choice to adapt or die.

2020 can be seen as a refiner’s fire or a dumpster fire. The choice is (always) up to you.


This article was written by Molly Rudberg, Molly Rudberg, LLC.

Molly Rudberg is an executive coach and leadership expert with clients in the United States and Europe. She specializes in helping C-Suite executives and teams identify and remove roadblocks to productivity. Her approach focuses on improving an organization’s bottom line while also strengthening the skills and relationships of its people. In practice for the past 17 years, Molly works with a wide variety of clients in verticals such as e-commerce, marketing, real estate, healthcare, and technology. She is a sought-after “fixer” for VC and PE groups who need help with the leadership teams within their investment portfolios. In addition to co-authoring “From the Yoga Mat to the Corner Office” (a book about integrating proven mindfulness techniques into management practices), she has been an invited faculty member at Dominican University in Illinois. Prior to the advent of the “Plague Year” of 2020, Molly was a frequent workshop leader and public speaker. Clients and audiences have described her work as “transformative”, “captivating”, and “wildly effective”. Her goal is to continue to live up to the high standards of her corporate and individual clients. Molly resides in Chicago with her husband, two children, and certifiably lunatic dog Rylie. She enjoys travel (and plans to enjoy it even more in the future!), her work with area non-profits, and spending time with her family.