Learning While Leading

Last week I spoke about my ongoing career journey and my most recent turn into the Chief of Staff role. I expected there to be one steep learning curve but what I hadn’t considered was the fact that I was also stepping into leading a distributed team. At times, it’s felt like I’ve been learning how to build a ship while also steering it at the same time (I borrowed this analogy from a fellow team mate). It’s been one of the biggest career challenges I’ve taken on thus far but I’ve begun to experiment with some approaches that I hope others find useful.

Thin slicing until you see the first step

It can be overwhelming taking on a new role and team so it’s important to thin slice the work ahead of you. In other words, how can I break down the work needed into smaller steps and decide which is the first step I need to take? This Agile methodology helped me see how I could identify what I needed to learn. For me, I needed to map out my career development milestones and build a team charter to act as my compass. 

Before I began setting my career development goals, I sat down with other folks in Chief of Staff positions within my organization. My intent was not to structure my role exactly like theirs (unless one specific charter really resonated with me) but rather to collect different data points on what this role could look like in action, based on what the team needed. What I learned was as a Chief of Staff to a Director of a sub team within a larger organization, it’s important to focus on only a few core functions to keep the team connected. Our Infrastructure Engineering team would be best served if I focused on three key areas: people, program management, and business strategy. 

In parallel, I worked with my small but mighty team to build a charter (as well as team agreements but more to come on that later) at our first offsite. We explored the different projects we were currently working on and examined the “why” behind them. This helped us find common threads across the work we were doing and served as a guide to predict which types of initiatives we should lead in the future. We learned that there were many priorities so a regularly groomed backlog would need to be part of our operating procedure to help us make decisions on trade offs and where we have slack to lend a helping hand as needed.

Taking the first few steps outside of my comfort zone

I had enough data points  to set my career goals around being a strong people leader who could help my team autonomously make decisions based on priorities. It was also important to build my strategic mindset given that was the area I had spent the least time developing thus far in my new role. Knowing that I’m the type of person who learns by doing, I would have to throw myself into spaces I’d be uncomfortable. That included ensuring key business decisions, planning, and execution was happening. In order for me to do that, I had to grow my understanding of the business, products, and services. I was also going to consciously focus on role modeling the behaviors my team and I built into our team agreements. The agreement closest to my heart was about supporting each other.

Learning while leading in action

This is where learning while leading comes into play. The next slice of work was looking at how I could gain a deep understanding of our business while leading my team to focus on the right things that would make the most positive impact. This would require a mentoring team that included me leaning on different people within our organization to test my understanding of our products and how it fits into our overall strategy. For example, I’d work with different Engineering Managers and Tech Leads to learn more about what their teams do. I also looked to industry experts to listen to their experiences and pull their lessons learned into my planning. My favorite domain experts are Brene Brown (known for “Daring Greatly” among many other publications) and Kim Scott, who’s perspective I loved reading about in “Radical Candor”. I found building a team of people to lean on was a great approach to accelerate my learning in multiple areas while still enjoying it. 

Keep in mind I am leading a newly built team simultaneously. And if I’m being completely honest, which I always am (value #1!), I made a few mis-steps. For one, I took on too many priorities at first. I was learning how to get comfortable with saying no unless a trade off could be made. With this came burn out; I noticed myself showing up tired and not focused in my team meetings. That was not fair to my team and I took responsibility for it. For instance, one day I apologized after a 1-1 with one of my direct reports where I just felt not there.  Other important Agile methodologies that have been great guiding principles for me are the Responsibility and Accountability models. I encourage anyone who is part of a team to check them out if you haven’t already. They’re useful tools to help you think about how you inwardly and outwardly show up.

The path forward

I now meet monthly, at a minimum, with my manager Skye on my career development and track my progress against the milestones we’ve set together. I’ve also shared my career plan with my team so they can help hold me accountable as I mis-step again (which I will; it’s part of the learning process) and provide me with feedback. This is also a great way to know where you’re improving and to tie learnings to concrete observations. For example, part of my leadership development has shown up in a recent conversation with a fellow manager on my team where I challenged their thinking on how distributed teams become high performing  and how it might look differently than their own team. The manager thanked me for that and was something I could celebrate as part of my own growth.

There’s a lot I’m still learning about. This will be an ongoing process but what’s helped me push through most is having a team that I can be honest and open with. This includes my direct, cross functional, and fellow leadership teams. It’s not fun learning alone and that’s why I love my job; I can make mistakes, have stressful days, and still end the week with a smile because I have people that I can decompress with. Sometimes I need to talk about something interesting I’ve read, others I’m testing my application of a recent learning, and at times I just need to vent. Finding a team of trusted people that you can map a career plan and take those turns together with makes growing not so scary, even if you are directing that ship while building it. 

Lessons learned

  • Breaking down the work helps you know where to focus first rather than getting distracted by all of the steps at once. Taking bite size steps is an effective way to keep focused on what the most important thing is right now.
  • Find people, tools, and methodologies that will help you learn in areas that you have gaps. Tackling career development alone is not fun nor near as effective.
  • Build your findings from the above into your team operating principles and continuously check for ways on how you can keep improving. 
  • Celebrate the wins. It’s great motivation and a good way to call out progress. Plus, it helps balance out those stressful days.

Homemade Beyond Burger Bolognese my husband Max made me during another evening of Shelter in Place. If I’m going to be stuck at hime, at least I’m lucky enough to have someone to make me comfort food!

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