Managing in a Remote World

Brian Rothenberg, Partner at
6 min readDec 8, 2020

Covid-19 has brought unprecedented challenges to the entire world. We at Defy know that the challenges faced by each of our portfolio companies, team members, and friends are different. Many are tackling new business opportunities or challenges, some are taking on the disruption of kids learning from home, and we’re all figuring out how to be as effective as possible working remotely with our teams. In times like these it’s especially crucial to be able to lean on a community for learning and support in order to adapt to these challenging circumstances and come out ready for tomorrow.

We brought together the entire Defy roster for our recent virtual event, “Managing in a Remote World”, where we not only learned from leadership coach Jami Zakem, but from one another as well. Jami brought her wealth of knowledge from over twenty years of building, leading, and participating in exceptional teams at Yelp and Eventbrite, and team members from a wide range of Defy companies shared their current observations, revelations, and struggles. During her time in the industry, guiding teams through high-growth stages, re-organizations, acquisitions, and IPOs, Jami learned that there are three pillars that managers must balance, and walked participants through them. Explore some of the lessons we learned in our insightful conversation below.

Lesson 1: This Remote World is not a normal one

Jami kicked off the session with this very important preface:

“We are managing in a remote world. We are also managing through change, and pandemics, and homeschooling, and pivots, and layoffs, and fear, and social injustice, and call for reform, and fires, and whatever else 2020 is going to throw at us. And so I just want to acknowledge that. I have managed remotely for most of my career — I’ve been based in the Bay Area, I’ve managed teams in Arizona, in New York, in Nashville, in Sydney, Australia, in Dublin, Ireland — this is not remote management. This is something entirely different. And if it feels different and if it feels hard it’s because it is.”

As managers, you’re always responsible for a wide variety of things. In this season your employee’s physical and mental wellness have become a top priority. No wonder it is harder to manage remotely, for many managers for the first time. Jami takes care to organize the various responsibility a manager holds in both physical and digital settings.

Lesson 2: Go back to the basics, deliberately

In a remote environment, you need to be especially conscious of the basics.

“Remote management, really good remote management, is not about the tools that you implement, or wholesale change of what you do. It’s about being incredibly deliberate about everything that you do.”

There are fundamental parts of effective management, and these remain unchanged no matter the environment. There are tons of moving pieces involved in moving to a remote world, logistical headaches, platforms and tools to learn, and a plethora of “Best Practice” Medium articles telling us how to change every inch of a business, from meetings to happy hours. Jami was not saying that there is anything wrong with any of these ideas or changes, but that focusing on particular actions is not really what enables good remote management. Instead, you should focus on the intentionality behind the actions, and really deliberately think about the basics of good management in general.

Lesson 3: There are Three Dimensions of Sustainable Success: It, We and I

What are the three pillars of management for sustainable success?

  1. “It” — the task at hand
  2. “We” — how relationships are at work
  3. “I” — how people are doing as individuals

The manager is responsible for balancing each of these three pillars. The “We” represents the overall culture supported by managers and companies: solidarity and trust are to be strived for. The “I” is the emotional, mental, spiritual, and physical well-being of each individual. Jami pointed out that far too often, the “We” and “I” are forgotten or set aside by managers. For short term success, perhaps focusing solely on the “It” can be effective. But if you want to achieve repeatable, sustainable success, managers must be mindful of overall culture within a company as well as the individual well-being of everyone from the founders down, including themselves.

Lesson 4: Take time and care to know your employee’s authentic self.

How might a manager go about cultivating the “I” and “We”?

An invaluable resource in a manager's toolbox is the “one-on-one”. The one-on-one is a powerful tool for genuine connection and tactical progress in your direct reports growth and ability to support you and your team. It can be overwhelming to know where to start if say you’ve never had a one-on-one with your employees or you’re one-on-one’s are one-off, sporadic, and only execution-oriented. Jami suggests six core questions to kick start your one-on-ones with each direct report. If you can’t answer these now, then you might want to bring them up in your next conversation.

  1. What is your full story? Ask to follow ons such as: what was your first job after college? What did you major in? Where are you from?
  2. How do you like to be managed?
  3. What motivates you? Pro tip: Be agnostic to the response.
  4. What are your goals? You might find, their way of working towards goals is different than yours!
  5. What’s your work from home set up like? This is critical today, assess what might be a core difficulty for them. Kids, bad wifi, bad back etc.
  6. Anything else I should know?

It’s never too late to sit down with your individual team members and ask these questions. Their answers might surprise you and lead to a better understanding of their needs. If helpful, write these notes down in a Google Doc or Notion to create a deeper connection long term.

Lesson 5: Set Clear Goals Together and Leverage Structures to Execute Upon Them

When was the last time you asked an employee or yourself, what are your goals for the quarter? Probably longer than best serving either of you! Leverage the “SMART” framework for diving into these goals.

After encouraging employees to set their SMART goals, you might ask employees how they plan to execute. The following questions help to encourage progress and structure. They also provide space for your employee to ask for help.

  • Do you have a project plan?
  • Are you moving things forward?
  • Do you need anything from me?

Your job is not done yet, don’t forget to check-in! The most successful people managers over-communicate expectations. You can do this through your one- on-ones or as my team does through an Agile style daily stand up where we discuss blockers and key objectives for the week.

Lesson 6: Say Thank You

Ultimately, your role as a manager is that of a coach. As a former athlete myself, I recognize that being coached is mostly about receiving constructive feedback while being motivated to continuously improve over time. Jami reminded us that this philosophy absolutely applies in coaching a team of working professionals. One thing that’s easy for coaches to forget to say but that can be a powerful motivator: “Thank you for your hard work.” While this isn’t a “praise report” it’s a small way to make your employees feel valued and appreciated.

Applying these six core lessons could help your team navigate through another year of abnormal remote work. We hope you gleaned some insights from Jami’s expertise and apply some of these lessons as End of the Year review season approaches!



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