You'll Manage

What do you do when you feel like an imposter or feel inadequate? Fake it till you make it? Or be forthcoming with your shortcomings?

Our guest Charlene Leung shares how when she first transitioned from individual contributor to people manager (less than a year ago!), she felt the pressure to project all-knowing confidence in order to earn the respect of her team, even when that confidence was false. But she came to see that putting up this false front was counterproductive, and that when she was willing to be vulnerable with herself and her direct reports, it brought her team together, built trust, and eased the anxieties that had often kept her up at night.

Why it matters

We often have an image of how a manager “should” act or come across. Confident. Cool. Capable. Ready to lead the way to succcess.

However, as Charlene shares, we may be doing ourselves and our teams a disservice by trying to mold ourselves into this archetype. In fact, showing vulnerability is a strength. Having open and honest conversations, including about your weaknesses and uncertainties, and enabling others to do the same is key to building rapport and trusting relationships within your team, as well as fostering an environment of collaboration, risk-taking, and growth.

Putting it into action

1. Be okay with not knowing everything, and ask for help

Everyone has limits and weaknesses, and we face new challenges every day. It's much harder to accommodate for and overcome them if you don't admit them though. Whether you're on day 1 or day 1000 of being a manager, don't be shy asking for help and guidance – and don't be too hard on yourself!

2. Admit to your team when you don’t know

Your job as a manager isn't to have all the answers. Your job is to guide your team towards finding the answers together. Get comfortable saying “I don’t know,” as long as you pair it with a plan to figure it out together. Inviting your direct reports to problem solve with you builds a stronger sense of ownership and engagement.

3. Create room for vulnerability within your team

Be conscious and deliberate about how you build trusting and mutually supportive relationships within your team. For example, Charlene created a regular forum for team members to share their challenges and seek help from each other – and she saw a dramatic impact on how they connected and collaborated with each other.

Other resources recommended by our guest

Bringing Up the Boss by Rachel Pacheco

Share your insights & experiences

When have you felt comfortable or uncomfortable being vulnerable with your team? In moments when you (or someone else) chose authenticity and vulnerability over false confidence, what impact did you observe?

We‘d love to hear from you at [email protected] or on Twitter @YoullManage!

Where to learn more about our guest

Charlene Leung is Group Product Manager at Ylopo. You can find and connect with her on LinkedIn.

“You'll Manage Challenge” episodes put theory into action, providing you a clear, achievable next step to up your management game within a week.

In Episode 11, Eusden Shing, an engineer-turned-product leader from Hulu and Pinterest, shared how he came about his set of core management principles, and how they have been key to effectively managing and guiding teams. Compiling a full set of "commandments" takes time, but in this week’s Challenge we’ll talk about how to get started, one principle at a time.

The management commandments You'll Manage Challenge

For this week’s challenge, you'll start identifying one or two principles based on the feedback you give to your team.

Here's how:

1. Note the feedback you have been giving this week and reflect on whether there are common or recurring themes.
2. Reflect on those themes and dig deeper to uncover the underlying reason for its prevalence. For example, a specific, prescriptive piece of feedback about how to conduct a meeting may reflect a broader principle or management truth that you believe in about communication or transparency.
3. Try to articulate that reason as simply and clearly as possible, such that you can then articulate going forward with your team. That’s your first principle! It doesn't need to be perfect – undoubtedly this will a forever evolving, iterative list.

Share your Challenge experience

Drop us an email at [email protected] or tweet us @youllmanage to let us know how your experience completing the Challenge was. What principles did you come up with? How did you uncover them? Or do you already have a set of principles that you've developed over time?

Even better, record a voice memo and attach it to your email, and we might feature you in a future episode of You'll Manage!

“No one is unreasonable.”

That's one of the 10 principles that engineer-turned-product guy Eusden Shing lives by. In this episode, he shares how having carefully crafted a list of principles has helped him lead teams at companies like Hulu and Pinterest. We learn about some of his top 10, including “trust is the foundation” and “focus on few things well,” and how he puts them into practice to manage and collaborate effectively.

Why it matters

Effective teamwork is often about effective alignment – around what matters and what doesn't, what success looks like, and how best to get there. Having clarity around your core beliefs helps us lead with focus and intentionality, but perhaps even more important is the ability to effectively articulate them. Building a shared understanding of how to collaborate and excel together not only helps align and mobilize your team, it also provides a framework for coaching your team members and giving them feedback.

What are your "commandments"?

Putting it into action

1. Start capturing potential principles

Reflect on your own experiences. What are some potential candidates for your list of operating principles? Is there anything you've learned from others that has stuck with you, whether from mentors and managers or books and podcasts? Are there concepts you often find yourself using to coach others? Start capturing it all in a live document.

2. Test them out

As you grow your list of potential principles, you’ll want to see which ones actually work. Try to put them into practice in your workplace – do these principles work in the context of helping you make decisions at work, collaborate with colleagues, and tackle tough challenges? Consider discussing them with your team and get their feedback as well to see if it resonates.

3. Communicate and incorporate

Once you feel you have a solid list that’s been tried and tested, it’s time to start spreading the word. Incorporate your principles into how you frame your actions, decisions, feedback, advice, and more. Make it part of onboarding for new team members. Ultimately, if they truly are effective, essential principles they should become an essential part of your team's culture

4. Iterate

Revisit your list periodically. Do the principles still make sense and still work for you and your team? Are there new ones you want to add and maybe ones that no longer resonate? What feedback have you gotten from others? Your journey as a manager is forever evolving, as well as the contexts you're working in, so it’s likely that your principles will evolve over time as well.

Other resources mentioned in this episode

• "No One is Unreasonable" by Seth Godin
• The Score Takes Care of Itself by Bill Walsh
• High Output Management by Andy Grove (introduces "task relevant maturity")

Share your insights & experiences

What are some of the principles you have on your list? How did you come to consider them essential? How do you propagate them within your team's culture?

We‘d love to hear from you at [email protected] or on Twitter @YoullManage!

Where to learn more about our guest

See Eusden's list of principles on his

“You'll Manage Challenge” episodes put theory into action, providing you a clear, achievable next step to up your management game within a week.

In Episode 9, Charlene Lee, head of product and design at Radar, spoke about the importance of building community and relationships at work. It's the perfect topic for a “You'll Manage Challenge”: A huge, daunting task that we can only start tackling bit by bit.

The community building You'll Manage Challenge

Your challenge this week is to take one deliberate step towards fostering a stronger community with your team. It can be small, like asking an icebreaker question at your next meeting, or bigger, like organizing a book club. It can be silly, like a dress-up day, or serious, like grouping new sets of people together on projects.

Every workplace and team community is different, so we can't tell you what exactly to try, but hopefully this episode provides some good options and a bit of inspiration.

Share your Challenge experience

Drop us an email at [email protected] or tweet us @youllmanage to let us know how your experience completing the Challenge was. What was your community-building effort? How did it go? What would you recommend to others?

Even better, record a voice memo and attach it to your email, and we might feature you in a future episode of You'll Manage!

We were electrified by two simple words in this interview: "community leader."

We've all felt how much more enjoyable and effective work can be when we're collaborating with people we have mutual trust, respect, and care for. By extension, Charlene Lee, head of product and design at Radar, points out, building effective teams means building community. And so, managers need to think of themselves as community leaders.

Why it matters

Charlene's perspective on management was shaped significantly by her time at Google, whose research has found that the relationships we have with colleagues aren't just a nice to have – they're a key foundation to effective teams. Google identified "psychological safety" as by far the most important dynamic for effective teams and creating "an inclusive team environment, showing concern for success and well-being" as one of the top 10 common behaviors of its best managers.

Thus, it's incumbent on good managers to build those connections – not just one-to-one with their direct reports, but among team members as well.

Putting it into action

Building community seems like a daunting task, but it can be done bit by bit. Charlene suggest starting with these three pillars:

1. Understand your community and get to know your all your team members. Who are they? What are their personal goals? (Listen to our interview about career conversations in episode 1 for more on this.)
2. Create space for community to get to know each other. Whether in small ways like icebreaker questions at the start of meetings or bigger ones like team activities, create opportunities for people to get to know each other personally.
3. Draw on your own experiences. Think back to when you felt included, psychologically safe, energized – times when you were excited to go to work and see your teammates every day. What made that experience so special? What can you do to bring that back into your own team, in your own authentic style?

Share your insights & experiences

How would you describe the communities you've been part of at work? What are ways you've successfully built and strengthened your team community? What aspects have been particularly challenging?

We‘d love to hear from you at [email protected] or on Twitter @YoullManage!

Where to learn more about our guest

Connect with Charlene Lee at charlenelee.me and visit her company Radar's website to learn more about the company and see the open roles in their fast-growing team!

“You'll Manage Challenge” episodes put theory into action, providing you a clear, achievable next step to up your management game within a week.

In Episode 7, CEO and co-founder of Remote Job van der Voort shared his passion for remote working and the incredible freedom and flexibility it brings. This week's challenge is about looking for ways to bring a bit of those benefits to yourself and your team, even if your organization is far from going fully remote.

The asynchronous work You'll Manage Challenge

Your challenge is to find something on your calendar in the coming week to make more asynchronous – and thus hopefully giving your team members more flexibility and leveling the playing field for those who are remote or unavailable.

Listen to the episode to hear some ideas for how you can do this, including Slack stand-ups, video introductions for new team members, making meetings partially asynchronous, and more.

For even more ideas, we also recommend GitLab's guide to Embracing asynchronous communication and Dropbox's Virtual First Toolkit.

Share your Challenge experience

Drop us an email at [email protected] to let us know how your experience completing the Challenge was. What did you try making more asynchronous? How did it go?

Even better, record a voice memo and attach it to your email, and we might feature you in a future episode of You'll Manage!

CEO and founder of Remote Job van der Voort has a message for all of us still adapting to working and managing from home – being forced to learn to operate remotely might be a blessing in disguise.

Once the VP of Product at GitLab, another fully-remote organization, Job was so passionate about empowering people to work from anywhere that he left to start a company that specializes in helping other businesses go remote. In this episode, he tells us why – and the lessons all managers can learn from managing remote.

Why it matters

Being able to manage a team well in person is already a big challenge, but in the past year, many of us have been introduced to another layer of complexity: Trying to do it all over Zoom. 

What Job has learned, though, is that it's a mistake to simply replicate what we did in the office for our new remote environments – we need to rethink everything.

Many of us have learnt, for example, that the awkwardness of interjecting on Zoom makes us a little less able or likely to pipe up in meetings. And what about those spontaneous watercooler moments when you build personal connections or informally catch up with what your colleague is working on — what do we do when those disappear? When we don’t intentionally readjust our working styles and processes, we run the risk of misalignment among team members, disengaged teams, and erosion of culture.

Putting it into action

1. Embrace it and be intentional. Redesign the remote working and managing experience from scratch rather than just copying what you did in the office.

For example, instead of just replicating the way you and your team communicated in the office, how would you rethink the format and frequency at which you communicate?

How would you redesign being a manager? Without the in-person interactions, how can you still build rapport and build strong relationships with your direct reports remotely? How do you know if someone is having a rough day if you can't see or hear them?

How can you still maintain and build culture remotely? Take decision-making for example – seeing how senior leaders think and decide is an important signal of culture and values. How can we enable people to listen, learn, and read about how decisions were made even if they weren't part of those discussions?

2. Write more. Since a lot of interactions in the office are fundamentally about information sharing, we need to be more intentional about how we communicate in a clear way that's accessible for all. Writing is key, whether it’s communicating big picture goals and vision or just letting someone know you have completed the work.

Reassess whether the meetings you're having are really necessary or if they can be replaced with email, Slack, or other written communication. 

3. Consciously connect with colleagues on a personal level. In a remote environment, we’ll need to compensate for losing those little interactions in the office that help us build personal connections.

Set up virtual coffee chats or lunches with your direct reports. Start calls with a bit of socializing before jumping straight into business. Play games or engage in activities that your team can continue to bond over (Job says he sent all of his team members a VR headset so they can connect virtually!).

Share your insights & experiences

What has your experience been like working and managing from home? What's different, and what's the same? What have you learned that you have or will bring back to the office?

We‘d love to hear from you at [email protected]!

Where to learn more about our guest

Find Remote co-founder and CEO Job van der Voort on Twitter

“You'll Manage Challenge” episodes put theory into action, providing you a clear, achievable next step to up your management game within a week.

In Episode 5, Tomás Campos revealed to us the one critical question he learned to ask at Uber: “What are your expectations of me as a manager?” It's not always an easy question to answer, though, so this week's Challenge provides some other ways to approach that question and start a conversation.

The expectations You'll Manage Challenge

Your challenge is to spark the conversation with at least one of your direct reports about how they expect and want from you as their manager. </p>

Here's how:

1. Ask them to tell you about:
2. something a past manager of theirs did that they really appreciated, and
3. something a past manager of theirs did that made them feel frustrated.
4. Dig into each and understand both the specifics of the events and the general insights you can draw.
5. Based on what you discuss and learn, talk about how you can best work with and support them.

Share your Challenge experience

Drop us an email at [email protected] to let us know how your experience completing the Challenge was. Did the Challenge successfully lead to a broader conversation about expectations? Did you learn something new about your direct report(s)? Did it change how you work with them?

Even better, record a voice memo and attach it to your email, and we might feature you in a future episode of You'll Manage!

Early Uber employee Tomás Campos circled the globe launching the service in new cities. Managing teams from different cultures, he discovered how essential it was to ask a simple, yet critical question: “What are your expectations of me as a manager?”

Listen in to hear Tomás share some of the painful consequences he faced before he learned to always ask – and why when he did ask, he says it was “one of the most interesting exercises I've ever gone through in my life.”

Why it matters

We often make assumptions about what others want based on our own experiences and therefore don’t take the time to explicitly ask our direct reports about their expectations of their role, the company, and, most importantly, us as managers. When we don’t ask, we miss out on an opportunity to truly understand what our direct reports care about, what they want, what makes them tick, and how we can best support them.

And when we make the wrong assumptions, often we find out the hard way—in the form of a conflict, underperformance, or even a resignation.

That's why it always pays off to just find out directly: “What are your expectations of me as a manager?”

Putting it into action

1. Find a time to sit down with your direct report or as part of your regular 1:1s, simply ask “What do you expect of me as your manager?” Don’t assume, even if you think you know.
2. Translate their expectations into a plan. How will you work to meet them (or, if needed, be clear about what you can't meet and what can be done instead)? For example, if they’re looking for more training, help them explore courses and programs. Or, if they expect you to help them get a promotion, work with them to identify milestones and metrics that will enable that.
3. Measure and track the progress of the plan. Check in together so that they know you're working to meet their expectations.
4. Ask the question at least once a quarter. As someone's career progresses or life circumstances evolve, their goals and expectations may change.
5. Clear expectation setting works both ways: Be clear and consistent in communicating your expectations of them as well. And as you demonstrate that you're working to meet their expectations, they'll be more motivated to meet yours.

Share your insights & experiences

Have you ever discovered the hard way that your assumptions about a direct report's expectations were wrong? Did you learn anything surprising when you asked directly about their expectations? Have you ever been asked this question yourself?

We‘d love to hear from you at [email protected]!

“You'll Manage Challenge” episodes put theory into action, providing you a clear, achievable next step to up your management game within a week.

In Episode 3 we talked about empowerment, and this week's Challenge will help you, well, challenge your direct reports! Using a four-stage framework, you'll be able to thoughtfully and carefully guide your team towards greater autonomy and responsibility (it's not the deep end or nothing!).

The empowerment You'll Manage Challenge

Your challenge is to take a clear, deliberate, calibrated step together with one of your direct reports towards greater empowerment.

Here's how:

1. Identify a upcoming task or project that you plan to involve a direct report in.
2. Locate where the direct report is in the four-stage model we discussed in the episode, in relation to this task or project.
3. Find ways to calibrate their level of responsibility and autonomy slightly higher than the stage you've identified them at.

Communicate these tweaks in expectations and processes clearly when briefing your direct report on the task or project.

Share your Challenge experience

Drop us an email at [email protected] to let us know how your experience completing the Challenge was. Did it change your perception of what your direct report is capable of? Did it change their self perception? How did the conversation with them go?

Even better, record a voice memo and attach it to your email, and we might feature you in a future episode of You'll Manage!