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Re-skilling middle managers: New ways to lead for distributed teams

A recap of FORTUNE and the Future Forum’s second “Reimagine Work” summit.

Posted December 21, 2020 by the Future Forum team

Reading time 6 min

On December 15, FORTUNE hosted its second “Reimagine Work” summit roundtable in partnership with the Future Forum. The session, titled “New Ways to Lead,” focused on the challenges that leaders—especially middle managers—face in the remote work environment. How can they foster productivity, belonging, and connectivity, while combating burnout? 

Alan Murray, CEO of FORTUNE, moderated the discussion with panelists Raj Choudhury, associate professor, Harvard Business School; Jenny Johnson, president and CEO, Franklin Templeton Investments; and Darren Murph, head of Remote, GitLab. Brian Elliott, the Slack vice president who leads Future Forum, shared insights gleaned from the inaugural Remote Employee Experience Index, a survey of 9,000 remote knowledge workers. 

Middle management feeling the squeeze

Elliott started off with insights from the Index related to middle managers, who are feeling the stress of remote work more than individual contributors and senior executives. They are 91% more likely than senior leaders to say it is harder to maintain relationships in the workplace, and only 63% of them felt they could rely on their colleagues to support them versus 90% of senior executives. They are 51% more likely than top executives to say they are spending too much time in meetings. Only 61% at the midlevel said their workload was manageable compared to 81% of senior execs. Their top challenge was staying on top of their team’s workload.

“We’re grappling with the fact that middle managers are struggling, whether they’re in companies that ‘measure by attendance,’ or companies that are more progressive and thinking about how to lead with purpose. We are taking people who are newer to the job of management, putting them in a remote setting, and saying ‘be productive and get your teams cohesively moving together.’ ”

Brian Elliott
Vice President, Future Forum

Not just work from home, work from anywhere

Choudhury has studied remote work for years. His newest research, recently published in Harvard Business Review, focuses on “work from anywhere” (WFA): not just work from home, but giving employees the flexibility to live wherever they want. 

“There are three main benefits. Work from anywhere expands the search for talent because now you’re not constrained by immigration, dual careers, or the economics of living in expensive locations. Inclusion, because firms can recruit from all kinds of geographies, genders, and socioeconomic indicators. And there are proven increases in productivity.” 

Raj Choudhury
Associate Professor, Harvard Business School

He notes that achieving WFA requires an organizational transformation, including rethinking how leaders measure productivity, communicate, codify knowledge, socialize, and manage regulation of labor laws. 

When asked about peoples’ sense of belonging, Choudhury argued that people connect better when working remotely, because in the office environment, they socialize with much the same people every day. On the other hand, in the remote work world, there’s an opportunity to create “planned randomized interactions,” drawing from teams that span hierarchies, cross-functional groups, and geographies. 

Focus on the softer side

Johnson agreed that the virtual environment democratizes interactions, if they’re planned. At Franklin Templeton, a fair percentage of the population adjusted to working from home naturally. Others had to be coached into figuring out how to work in that environment. But another segment of people, ultimately, never got comfortable managing oriented around results or creating flexible workflows. Getting the majority of people comfortable with working and managing remotely has required experimentation.

“Several lessons we’ve learned: it’s all about the softer side. One of our subsidiaries has virtual cocktail hours on Fridays that have been amazingly effective. In terms of middle managers not having networks, we’ve told people to reach out, virtually, to five people within the company they don’t know. Giving them permission to do so, and that has to come from the top, makes a huge difference.”

Jenny Johnson
President and CEO, Franklin Templeton Investments

Transparency leads to belonging

Murph advocated putting an employee in charge of remote work, similar to his role, rather than adding it as a line item to another executive’s long list. He also talked about what he has found is the most successful way to build a sense of belonging.

“There’s an element of belonging that is rarely talked about and is woefully missing for middle managers right now, and that’s transparency. Many organizations were not set up to be transparent about how and where work happens…When you can’t see what other people are working on, you feel like you belong less. At Gitlab, it’s very easy to cross any of our virtual functions without tapping someone on the virtual shoulder and see their OKRs, goals, status updates, and progress. It makes us all feel like we belong to a team.” 

Darren Murph
Head of Remote, GitLab

Elliott supported the claim, saying Future Forum’s survey found teams that leveraged modern technologies to share content openly weren’t struggling as much with the middle-management task of wondering “what is my team doing,” while managers who defaulted to meetings performed worse. 

Train leaders for empathy and reduce meetings

Tracy Layney, senior vice president and chief human resources officer at Levi Strauss & Co., added a different perspective, because her company’s workforce has a large percentage of retail workers. She offered best practices for treating all employees to avoid burnout and overload. 

“We’ve really invested in mental health and wellbeing, and a key component of it is manager training. Globally, we conducted ‘Manager Reset,’ about leading with empathy and understanding how to take care of yourself, and how to meet employees where they are. Most of what we’ve learned and done during the pandemic, we need to keep doing.” 

Tracy Layney
Senior Vice President & CHRO, Levi Strauss & Co.

Flexible policies will be essential for talent

The panelists agreed that companies with flexible policies will be able to recruit and retain the best talent. Murph predicted that companies that don’t allow 100% remote work in the future will suffer in hiring. Several panelists offered closing thoughts about talent and remote work. 

“My message to managers six months ago was ‘Use this time to push the envelope about how you can flexibly work so that you’re the one recruiting the best talent from your competitors’…The tools and technologies exist for you to enable remote work. If you can’t accommodate your talent, others will.”

Jenny Johnson
President & CEO, Franklin Templeton Investments

“You can’t put the genie back in the bottle. Now that people realize that in some roles and in some industries, their jobs can be done from anywhere in the world, they’re going to try to take advantage of that, as they should.”

Darren Murph
Head of Remote, GitLab

“In 18 months, companies that manage this transition better will have a leg up in the talent game, in every industry. This is going to be a mechanism to attract and retain talent. And this whole ‘work from anywhere’ movement will allow talent to move back to smaller towns in middle America and all over the world. We’ll see a return migration from the coasts to places that have lost talent for decades. This is going to be great for society.” 

Raj Choudhury
Associate Professor, Harvard Business School