Six Leadership Lessons In Six Months: Learning On The Job As The Chief Learning Officer Of A Learning Company – Forbes

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Meeting with your manager on the first day, leading your first weekly meeting with your team, your first monthly check in on team objectives, and in month six, your first major organizational change are a lot of firsts. “Firsts” with any new job present a multitude of challenges. Learning about people, processes, and practices is already a steep learning curve. Doing all this while also getting to know your team and colleagues virtually adds another layer of challenges into the mix of “firsts.”
As leaders, we have all experienced our first days on the job, and with every new job, we take those lessons into the next one. I have written about what leaders can do to integrate with their team in the first 90 days. This is my personal journey, leveraging some of those best practices and more.
Hopefully, you can leverage these lessons along with your own as you take on your next leadership role: Here are six leadership lessons I learned during my first six months as the Chief Learning Officer of Udemy.
1) Small wins: When I started in past leadership roles, either in new organizations or through a promotion, I wanted to get that “big win” within my first two weeks. I had a mentor earlier in my career who said that if I didn’t get a big win by the end of that two weeks, I wasn’t likely to succeed. Big wins are important and you should focus on them. However, I began to realize that if I focused and looked for only those big wins, I missed all the small wins in between. And sometimes it’s the small wins that make the biggest difference, because they not only lead to those big wins, they help establish relationships and connections across the organization.
By little wins, I mean times when I asked a question that prompted a shift in strategy, or the time that I made that genuine connection with my team or when I unexpectedly shared about my mom’s passing. There was also that time when a team member wanted to talk through a difficult situation, and, together, we came up with a better solution than neither of us had thought of before. Those were all wins because they led to great results, together. Do not lose focus on the small wins while bringing others along. They make it easier to create those big ones.
2) Always learning: Too often, I have seen new leaders (including me) dive into wanting to make a change for the sake of change. We may have shared the same “big win-focused mentor”. Just like big wins are good, so is change, especially in an organization that needs a little shake up. However, the best change leaders I know listen and learn first before making any changes.
One of our values at Udemy is “Always Learning.” That has shown up for me through behaviors of listening, asking good questions, inviting constructive debate, guiding me to the right Google documents, and patience from others answering the same question I have asked a few times before (Ok, maybe more than a few times). It also can be observed when we make critical decisions about what needs to stay the same, evolve, or be overhauled altogether.
True learning is about change, whether it’s changing individual behaviors or organizational processes.Those kinds of changes can’t happen without listening. Take the time to share more about yourself, listen, learn the product, the business, and ask those questions that you won’t be able to ask as much after six months. Identify trends you are hearing and reflect on themes that are emerging. All of these are inputs to the strategy that you need to build with your team. In my first six months, I talked to over 100 employees and 50 customers. Through these discussions, I’ve been able to be a learner, and ultimately, a co-creator on some bigger changes that are contributing to our learning and organizational strategies.
3) Personal culture: In my upcoming book, ReCulturing, I share a framework about how to design and build organizational culture. However, it is challenging to make cultural changes at the organizational level without first looking at ourselves and our own system. I ask people to first look at their personal culture. A personal culture is like an organizational culture: values-based behaviors, practices, and processes, connected to our purpose and goals. When we define these components, we become more effective at managing ourselves and our team.
Psychologist Warner Burke, one of the most important leaders in the field of organization development, coined the term “self as instrument”. It means going beyond self-awareness; it is an active use of our awareness when we are working with and leading others. “Self as Instrument” reminds us that behind the slides, behind the frameworks, behind the theories is us. “Self as Instrument” is a reminder that we need to start with our own system in order to impact and influence the organizational one. Every person can lead, but leading effectively starts with first understanding more about ourselves and our own “personal culture.” During those first 6 months, I often revisited my values, practices and goals with my team.
4) Clarify Expectations & Practices: Speaking of personal cultures, it’s important to set expectations and practices for yourself, with your team, and colleagues. Too often, I have over-promised and over-delivered, leading to burnout. I have not been clear about what’s remaining the same and what is changing. Get clear on what’s important, identify what’s urgent, and re-visit working practices to get the priorities done. It’s important to focus on the day-to-day issues that have been waiting for you before you started with the company. It’s also important to connect these issues with the longer term strategy. Making space in your days to do the deep work as well as making time to respond to more timely issues is a key component to short and long term success.
5) Make Space: It can take as long as six months to a year to feel comfortable in a new leadership position. I’ve written before about the importance of creating space in our days. While it’s counterintuitive, this is especially true as a new leader. It’s not our full calendars, email, Twitter, or <insert latest app here> that’s distracting us. It’s our way of working, our practices that we haven’t defined or are not disciplined enough to follow. In a world of infinite distractions, we need to be better curators and masters of our time and energy. Clarify your working schedule, set boundaries and priorities, be clear about what you need and what you expect from others. At Udemy, we have a focused work block time on Wednesday afternoons. Our leaders work to model keeping that space open as much as possible. We also encourage teams to look at their work practices each quarter as new team members come on to identify if meetings, communication tools, and different ways of connecting need to be reviewed.
6) Emotional Agility: Just like we need healthy organizational and personal cultures, we also need evolving organizations and leaders. I remember a time not so long ago when VUCA was the new acronym that everyone was discussing. It stands for volatility, uncertainty, complexity, and ambiguity. It describes an environment in which change is constant and unpredictable. Now VUCA is just part of our everyday experience. When we don’t pivot fast enough with the changing circumstances, organizational change can fail and we can burnout. Emotional agility is being aware of what triggers us, working through our reactions, and responding neutrally toward a productive outcome.
As the Chief Learning Officer at Udemy, I am not only focused on developing Udemates, our internal employees, but also look at how we can evolve our learning products, solutions and services with our customers. There are a lot of changes to manage within my own team, our organization, our customers and our products. It’s easy to react mindlessly to issues that come up versus thinking through how you can effectively work through them.
It takes time to get used to new environments and learn how everyone works together, and, eventually, how everyone connects together. There’s a lot to get done, and it’s important to get it all done while building those relationships. Jennifer Aaker and Naomi Bagdonas, co-authors of “Humor, Seriously,” shared that, “We’re living in a time when empathy, inclusivity, and authenticity are important for all leaders. Building relationships takes time. Whether you value humor, connection, or alignment, keep that focus in mind with every interaction”.
It is important to remember that starting a new leadership role is hard whether you’re a CXO, business unit manager, or managing for the first time. My hope is that by sharing some of my own lessons from the first days and months on a new job, they will inform how you navigate future career moves and remember that learning lessons along the way is part of the journey.
Always learning.

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