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  • Writer's picturebrittany bennett

How I learned to stop worrying and love being a manager

Updated: Jul 6

When I first started as the Data Director of Sunrise Movement, I was terrified to be a manager. For the first five years of my career, from the time I graduated college until the time I started at Sunrise, I floundered from one toxic, underpaid job to the next. Throughout all of my terrible jobs was one consistent factor: my managers were horrendous. They were overbearing, not letting me send an email to a coworker without proofreading it first. They were micromanaging, forcing me to write a 12-page memo to prove I could place an order of tacos for an event. They were sexist, giving all the available work to my male counterpart and asking me to plan a happy hour instead. They made me feel small, stupid, and worthless.

So when I inherited Sunrise’s Data Team, I was petrified that I would cause the same harm to my team that my past managers had caused to me. I wanted my team to feel empowered, to feel like they were truly leaders just as much as I was, to feel safe in the workplace. So I took a step back. I let them be the deciders of their workload. I refrained from offering any kind of critique. I allowed my staff to manage their own projects.

My fear of being a bad manager led me to swing so hard the other way that I ended up not managing my team at all!

I was not allowed to stay within my comfort zone for very long. Within the first few months of my time at Sunrise, we had a set of performance evaluations. Across the board, every single person I managed came to me and said: “You are not managing us. We want you to manage us. Please be more hands on.” I was shocked. I thought I had been such a good manager! Look at how I was not managing! Obviously my hands-off approach was not working.

I spent the next year pushing myself to be more hands-on with my team. I sought for a way to be a manager that was still in line with my values: that recognized the people I managed as capable, intelligent leaders who were allowed to disagree with me. Along the way, I uncovered techniques and methods for managing my staff that were empathetic and supportive, not punitive and demeaning, and today I want to share them with you.

Management Methods

The following are a two tricks I picked up while managing my Data Team at Sunrise. These may or may not work for your team! I was managing a fully remote team of junior analysts and engineers, some of whom this was their first job out of college. Your case may (and should!) differ, sometimes wildly.

Daily Intention Setting Thread

Remote work has its challenges. The most common feedback I got was that people were dying to know what the other members of the team were working on. Since we all worked remote on different projects for different parts of the organization, it was challenging, even for me as the Director on the team, to know what everyone was working on.

So, I decided to institute a daily stand up. Now, I know many tech teams have some version of a daily standup meeting--I have not invented anything new her--, but this was not a practice for any team at my organization! I do not know too many nonprofit data teams that use a standup.

I decided that instead of mandating an early meeting for folks working across three timezones that I would opt for a much more lenient asynchronous standup. So I set up a Slackbot to kick-off the thread every work day at 10:00am ET and set a practice on my team that we would fill it out by noon in their time zone. The Slackbot poses three questions:

  • Did you accomplish what you wanted to yesterday?

  • What are your intentions for today?

  • Any blockers/requests?

The phrasing of these questions is very intentional. I could have asked "What are you working on?" and left it at that. Instead, I wanted to build in a mindfulness moment for my team.

mindfulness : the practice of maintaining a nonjudgmental state of heightened or complete awareness of one's thoughts, emotions, or experiences on a moment-to-moment basis

I believed that the best strategy I could employ as an empathetic manager was to create systems that allow my team to take a step back from the chaos of the day to reflect on their work, without invoking judgment or shame.

The first question, “Did you accomplish what you wanted to yesterday” asks my team in a non-judgmental way to reflect on how their previous day went. Did they get everything they set out to do? Or did they get distracted by urgent requests and emails? Did they really focus during that two hour block to dig into that new project, or did they instead use that time to take care of all the little tasks on their plate? I would first model this by commenting on my own work habits.

The second question “What are your intentions for today” encouraged my team to set priorities, and to stick to those priorities even when new and urgent work popped up in the middle of the day.

The third and final question started off as an innocuous place to uplift any blockers and ask for help, but slowly morphed into a chance for my team to share personal anecdotes about their day. The intention was to encourage my team to rely on one another for working through hard problems, but also grew into a place where folk could share pet photos, talk about the walk they were able to take before starting work, and describe any time off they needed to take during the day.

But how did I get my team to take this seriously? I modeled the behavior I expected from my team. My responses to the Daily Intention Setting thread showed off my productivity to be sure, but also opened up the window a little bit for my reports to see that I was human too. I talked about my challenges with staying on top of my work while feeding myself three times a day, the times I failed to complete a task or project on time, or when a script I was writing would take me longer than expected. I found it was easier for my reports to own up to their mistakes and shortcomings if their boss was doing the same.

Asana projects status reports

When I set off to write this blog, I promised myself it would not turn into an ad for Asana. But I need to be honest: I love Asana.

Asana was a total game changer for me and my team at Sunrise. It allowed me as a manager to have insight into the day to day work of my reports while giving them a tool to organize and keep track of all their incoming tasks. That being said, Asana is not the only project management tool out there. You can absolutely take these tactics and apply them using your tool of choice. Asana just happens to really scratch that itch for me.

A few months into our Asana experiment, I asked my team to start filling out Asana’s bi-weekly project status reports. You can see an example of what that looks like below:

Every other Friday a Slackbot would prompt my team to fill out their project status reports. Asana's template prompts the user to fill in a status update (On Track, At Risk, Off Track, On Hold) and then to respond to a series of prompts: a summary, accomplishments, blocks, and next steps.

These reports had a dual purpose. First, it gave me the information I needed as a manager to project manage my team. One of the challenges I was facing in my role was that I was not usually the person delegating work to my team. New tasks and projects came in laterally from our other coworkers, and I did not always know when a member of my team had been asked to fix a dashboard, or write a new report, or troubleshoot someone's Zapier. I was able to use this reports to manage my reports workloads, step in if they needed to reprioritize their work, offer a hand in problem solving, or simply praise them for doing good work.

But the real value of these project status reports came in the mindfulness moment it gave my team. It opened up a bigger space than the Daily Intention Setting thread for my reports to sit down and really reflect on their work.

Did they let a blocker halt all progress on their project? Did they solve a particular difficult problem? Did they finish a project and can celebrate a win? Are they letting a project drag on for weeks?

I found that these project status reports allowed my team to somewhat project manage themselves. I did not have the capacity to project manage the dozen plus active projects across my 5 member team, and I certainly did not want to micro manage any member of my team. By proving a structure for my team to engage in mindfulness, they were able to do 70% of project management on their own.

Holding Up the Mirror

"But brittany, you used all these techniques to totally escape having to manage your team!"

Look I admit it. Part of my rationale for setting up these systems was to remove myself from the management equation. I was still too stunted to really step into my role as a manager and give direction. But let me be clear, you cannot implement these strategies and walk away. These techniques require an active manager to guide employees through their self reflection, very much not unlike the role of a therapist.

It was my job as a manage to "hold up the mirror." There are a couple of business articles on what this practices entails, but I think of it as using a series of questions to guide your report into seeing a more accurate depiction of themselves. This active management technique combined with the more passive mindfulness exercises I described above became my staple as a manager.

Let's take a completely hypothetical situation. An employee is struggling with a project. During their Daily Intention Setting Threads they say they are going to work on each day, but end of getting distracted by other work. When they go to submit their project status report, they have not made as much progress on the project and they needed to in order to meet the deadline. Here is how I would "hold up the mirror" in our next 1:1 management meeting by asking a series of guided questions:

  • How did you feel about your work?

  • What did you find yourself spending the most time on?

  • Did you find that you were spending more time on your project work or more on the rapid response work that came up from our coworkers?

  • Have you noticed a difference in your productivity from before the pandemic when you worked in a co-working space and now when you work from home?

  • What time management techniques have worked for you in the past? Do you like to set timers? Do you find that blocking off portions of your calendar tend to help?

  • Can we take 5 minutes right now and block off at least 5 hours next week to focus on this project?

  • Is there someone else we can delegate this other task too?

  • What will you do if something pops up next week that needs your attention?

And so on and so no.

Look, none of this should be groundbreaking news if you have managed someone before. The trick here is withholding your judgment. Instead of coming in hot ready to solve your reports problem, take a moment to ask a lot of questions to really understand the situation. Are they dealing with a personal issue? How has the pandemic affected them? Are they simply having a bad week? Do they need a new time management technique suggestion or a reminder or one that works for them?

The goal is to guide the people you manage to a place seeing both their strengths and shortcomings without triggering their ape-brain judgment mechanism. I strongly believe that growth and learning cannot happen from a place of shame. If we truly believe in our reports, and we sincerely want them to grow and improve, we need to actively create safe environments that reduce shame. Modeling vulnerability, encouraging mindfulness, and holding up the mirror are all management techniques to create powerful teams.

Lessons Learned

When I started in my management journey, I thought the best manager I could be was a manager that did not manage at all. How cool would that be! A manager that never pointed it out when you when you missed a deadline or made a huge mistake in a report. One that let you make all the decisions and never gave their own opinion (because that would be micro-management).

I was wrong. Like, really wrong. Feedback is a gift, and to not give that gift to someone you love is a disservice. I want everyone I manage to become the best version of themselves that they can be, and it is my dream for the folks that pass under my wing to surpass me one day. To be a good manager, I needed to learn to be comfortable with pushing my team to grow, and to do that people need to know how they need to grow.

But I wanted to find a way to manage my team without falling into the same traumatizing management techniques I had experienced in my early twenties. I think my balance of creating space for my team to engage in mindfulness practice, modeling what that mindfulness looks like as their manager, and actively engaging in dialogue with my reports by "holding up the mirror" has really worked well for both me and my team. I would love to insert a testimonial here, or hold up one of my past performance evaluations like a child showing their report card to a parent, but I think all I can do is ask for you to try this out for yourself and see what happens (:

I am always excited to add more tools to my toolbox. What management techniques do you enjoy?

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