Becoming the Boss: Guidance for New Supervisors in an Era of Remote Work

Author: ISACA Now
Date Published: 30 June 2020

Editor’s note: Emily Tsitrian, senior manager of professional services at Castlight Health, presented last week at the Pride Summit in her session, “Boss Up! How to Become the Boss.” Tsitrian visited with ISACA Now following her session to share some of her guidance on transitioning to becoming a supervisor, especially in current times in which remote work has become increasingly commonplace. Below is a transcript of the conversation, edited for length and clarity:

ISACA Now: What are some of the most common missteps people make when they are new to a supervisory/management role?
It can take six months to a year for first-time managers to settle into their new role and set of responsibilities. During this time, it’s important to learn the ropes of “how to” when it comes to the responsibilities on paper, such as learning how to approve expenses, execute performance reviews and the ins and outs of hiring processes. The harder part is to navigate the new normal when it comes to adjusting to your new position of power and influence, knowing that your words and actions have a much bigger impact and so there is a need to be more deliberate, reflective and humble in your approach.

The biggest singular mistake I see most frequently is being afraid or sheepish around making decisions. Executive decision-making is both an art and a science, and new managers have to get comfortable with the fact that not all their decisions will be good ones and that not everyone will agree with their decisions. It’s almost like a constant state of vulnerability that requires a mental adjustment and practice to adopt. 

ISACA Now: For people who might be technical practitioners but have aspirations of advancing in their careers, what are some key management skills to cultivate and what are the best ways to go about attaining them?
My advice for aspiring people managers is to go for it! The world needs fantastic people managers across every industry to make lasting change and advance the human race forward. That said, here are a few practical suggestions for building a career path in management.

The first is to explicitly tell your manager and mentors that you’re interested in exploring this career path and to find extracurricular work opportunities that are similar to “management lite” – these can include volunteering to facilitate meetings, supervise interns, coach and ramp a new hire, or represent the department’s needs at a cross-functional meeting. These activities will both help you understand if these are types of responsibilities you enjoy, and will help make you a competitive candidate for a first-time management position.

The second is to work to establish yourself as a team “caretaker” when it comes to the general sense of emotional wellbeing and psychological safety of the team. Be intentional about setting up frequent 1:1s to just catch up and chat with various folks, focusing on deep listening and providing helpful suggestions and feedback. At the same time, it’s important to stay slightly aloof and have a little bit of social distance while maintaining emotional presence. Avoid the urge to engage in gossip or excessive venting – these behaviors may help you connect socially with your team but will need to be course-corrected when you eventually become their manager, so be mindful! If you have an established, trusting relationship with the team you may lead one day it will make you an ideal next-generation manager and help you adjust to the new normal once you do.

The third is to demonstrate active interest and dialogue with departments outside of your own – this is a core trait of great managers to be able to easily empathize and comprehend business needs and bigger picture goals in an inter-department sense. And, building relationships with colleagues across the company is what will help a new manager address issues and needs in their “home” department.

ISACA Now: How will the supervisor/employee relationship be impacted most by this trend toward remote work that the pandemic has accelerated?
I am very optimistic about how remote work will contribute to more functional and meaningful supervisor/employee relationships. In full transparency, I have led more remote teams than in-person teams and my personal preference is a distributed team, but certainly there are perks to being able to physically be in the trenches with your crew day in and day out.

Some of the business-related benefits include being able to offer more work-life balance and hire a more diverse team since you can source from cities outside of your company’s main headquarters. I also find it easier to connect with my team during 1:1s; there is a certain level of intimacy with speaking together in your homes. I find it easier to get to know their home and personal life as well as sharing mine. For example, if I’m taking a call on my porch and they’re next to their dog, it provides a natural way to connect about our home lives and what our day-to-day is like outside of work. I might show my new porch furniture and they might turn their volume up so I can hear their snoring dog beside them. These moments aren’t natural in an office setting.

I do think that managers need to be conscious of establishing both a casual/informal conversation norm as well as a more formal one, and that can be tricky to do. Since you won’t have those moments in the break room, good morning chit-chats and other opportunities to just connect and build a rapport with your team, it’s important to still make little moments of connection a priority. I recommend occasionally calling your team members to catch up, sending fun little gifs through your company chat channels, ensure you’re finding random things to connect on like the Netflix series you both happen to be watching, the new hobbies you’ve picked up, etc.

ISACA Now: Impostor syndrome is increasingly acknowledged as a serious challenge for people who are taking on new and more demanding roles. What is your take on impostor syndrome and how people can work through it?
My advice is two-fold. One, I encourage leaders to embrace the humility that comes with the sense of imposter syndrome. Humility asks us to show great respect for our roles and our positions of power, and fully grasp the impact our work has on our teams, our industry, and our clients. Acknowledging this and working with it, rather than against it, can actually make you an even more powerful leader. Vulnerability and power are two sides of the same coin, and imposter syndrome can actually *help* you approach your leadership role from a place of humility.

Secondly, I encourage anyone grappling with imposter syndrome to seek feedback from trusted peers in your professional to obtain an objective view of your performance, skills, and areas of growth from folks you trust. That way, you can “trick” your brain into an objective understanding of your work since you know it’s coming from people you deeply trust, rather than listening to the voice in your head that is overly self-critical.