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DevOps / Tech Life

Help! I’m a Leader Now

Practical advice for overcoming some common challenges new managers face after taking on a leadership role.
Nov 3rd, 2023 10:30am by
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I’ve worked with new leaders across a lot of private, public and impact sector software organizations. I hear this story a lot:

I’m a new team leader, and I’m overwhelmed. My calendar is stuffed with all kinds of meetings, requested by all kinds of people. I go from conversation to conversation, trying to be helpful, and spend most of each chat orienting myself to this new person in front of me. I try to fit them into my world, find an answer, maybe even some action items, and then it’s time for the next call.

“I feel like I’m all alone. The team I used to be on doesn’t really know what I do all day, and to be honest, neither do I. I don’t have concrete outputs like I used to, or a tightly knit team to celebrate or commiserate with. My peer leaders are all off doing other things, leading other teams. We can talk about the larger organizational goals, but they don’t really see what I see. Even my boss doesn’t see what I see every day. Their advice on how to do the job is helpful, but nobody else holds all the context I hold and could help me be confident in my decisions.

“I have no idea if I’m doing the right thing. I don’t know if I’m focusing where I should focus, doing my work well or adding value to my organization. Help!”

I’m here to tell you that this experience is normal. It’s fine. And you’re not messing up your job. There are a couple things going on here, and naming them can help get them under control. Let’s start by looking at why it feels this way.

Challenges New Leaders Face

You’re Working up and across to Support the Team

When you were on a team, there was a group of people who had exactly the same goal as you: to deliver outcomes by shipping software. That meant you could work mostly with them; they knew your challenges, and they could really help.

Now your job is to make a safe environment for that team to do its work. You’re talking to a lot more different people. You’re coordinating across larger chunks of the organization to detect challenges to the team’s ability to autonomously deliver value, and you’re working to keep that team able to succeed. The amount of time you spend with a core group has gone way down, and the amount you spend negotiating with new people has gone way up.

You don’t have the same level of trust with everyone you work with, as you did when you were on a software team. You simply don’t know them as well.

You’re Prioritizing Different Kinds of Work

You used to just pick the work that got your team closest to the next milestone. Now you’re getting requests from all kinds of places for your time. And you’re having trouble picking between all the tasks coming at you. Here’s a set of tasks you might have to choose between:

  • Reviewing a team’s roadmap
  • Evaluating a new vendor
  • Interviewing candidates
  • Preparing for a promotion round
  • Unblocking a team’s access to users
  • Helping two people work together better
  • Making a case for increased investment in a key product area
  • Giving feedback on a proposed new office policy

These are all valid work, and they’re all in service of very different goals. So which one is most important? Hard to say. It’s worth being aware that there are two new things here for you: 1) The work itself is different, and 2) The prioritization decision — picking which task to do next — is harder.

Your Time Is a Scarce Resource

A lot of people want your help with a lot of things. None of them know everything you’re dealing with, and usually they assume that their issue is your No. 1 priority. When you were on a team, it was easy to prioritize activities together to move forward, and you could spend time together considering the options. That’s what a team does.

Now that you’re in leadership, your calendar is simply much fuller. Lots of people want to hear your thoughts, and even more people want you to hear their thoughts. They want to have input on the decisions you make, and they want to feel heard by you.

You’re representing the organization now, and what you focus on with your time is a statement about your organization’s values. More people in the organization will pay attention to how you focus, and what you think is important. Choosing what you do has a lot more impact than before.

How to Overcome Challenges as a New Leader

These are real changes from your previous role, and they’re part of what makes leadership hard. Here are some concrete things you can do to handle them.

Build a Network of Peer Leaders

They won’t know the details of your work, but you can learn from each other about the craft of leadership. You’ll need to be vulnerable. To really benefit from a community like this, you’ll need to take what you’re most afraid of and share it with others. Get their feedback and input. That’s how you can learn to grow as a leader. Even better: It models vulnerability for them and for your team, which supports a learning culture throughout your organization, which is, in fact, your job.

Make a Lot of Time to Plan Your Week

Picking the right work to do on a team is relatively easy. You’re choosing the thing that gets you closest to the goal. When you’re in leadership, you’ve got at least nine goals at any given time. Picking the right work to do is harder.

So, block time on your calendar to keep your to-do list under control and to make clear choices about where to focus. A lot of individual contributors, particularly in product and design, already do this. They take time at the beginning of the day or week to step back and plan where they want to focus to make the most impact. If you’re already doing that, great! In your new leadership role, block even more time.

Your plan will probably be disrupted by Tuesday. That’s OK. It’s both a plan for the time in the week and a statement of priorities. Having a plan means faster adjustments and better focus.

When you’re making that plan, try to put similar tasks — and working with similar groups of people — next to each other in your week. Switching contexts from project to project all day long is hard; it’s work in itself! By “defragging your calendar,” you can eliminate some of that work entirely.

Create Your Own Work to Do

If you just do what everyone’s asking you to do, you’re going to be carrying out someone else’s priorities. You’ll just be led by the nose from meeting to meeting, without ever deciding where you want to go. As a leader, your perceptions of what’s important to the organization — and what needs to be accomplished — are an essential contribution.

Make the time to figure out what you think needs to be done, and then make the time to do it. This will mean clearing even more time on your calendar away from all those things everyone else is asking you to do. It will mean going out on a limb to say what you think needs to happen, building support for it and then executing it.

That’s your job, too. If you just do what everyone else asks of you, you’re denying your team the benefit of your full brain.

Trust Your Judgment

You’re making a lot of decisions on your own. Nobody else is in quite the same position you are. You can share context, but it’s still your context, your responsibility and your decision. You’ve got to say no to a lot of people.

That’s OK. Your leadership trusts your judgment already. That’s why they put you in this role. Hiring a leader means asking, “Will this person do the right thing in private, when nobody will ever be able to check on them and they don’t have time to ask me for help?” And you only put someone in charge if the answer is yes. For you, in your new role, your boss said yes.

Trust that they knew what they were doing. Trust in yourself. Go decide some things and hope you get most of it right. That’s all anyone can do.

For more practical management advice born out of years of experience working with software teams in a wide variety of industries, download the e-book “Mindsets and Tactics for New Leaders of Software Teams.”

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