Management Mistakes I’ve Made

Last week, I gave a presentation at the Poynter Institute’s Women’s Leadership Academy about “Management Mistakes I’ve Made.”

This is kind of like my Greatest Hits album of work screw-ups over the last few years. I’d been thinking about some version of this presentation for about a year now, having kept a running idea list at my desk…

In my last leadership presentation, I spoke about our team’s core beliefs that helped us scale from 8 to 50 people. In this presentation, I’ll talk about my personal experiences as the lead of a growing team.

Here’s the presentation I gave to 30 digital women leaders at the Poynter Institute, loosely written in transcript-style, with slides embedded.

Management Mistakes I’ve Made… so you don’t have to. But… let’s be honest, you’re going to make mistakes, because failure is an ingredient to success. At the very least, though, I hope seeing someone else’s mistakes will help you expedite the learning – and you can power through the mistakes faster than I ever did.

You may be the only female lead in your organization. The only minority lead. You may be spearheading a new project. Creating a brand new position. Being a lead can be very lonely, and the mistakes you make can seem magnified. I’m giving this talk because these are things I wish I had known at the start of my leadership journey. I want you all to know that you aren’t alone, and many of these mistakes are part of the learning process.

When you become a lead, it often goes like this: Congratulations! You are now a lead! Now I’m going to give you added responsibility, without telling you what you’re responsible for, or, give you the tools to do your job. The reality is, most bosses are very busy, and all you need to do is ask.

There is a lot of inbound as a new lead, and it can be hard to get clarity through the chaos. Lean on your boss for prioritization and guidelines. Ask them to provide resources (like books, conferences, classes) or help (like coaching). Similar to how it’s your job to develop your team, it’s your boss’s job to help develop you as a lead.

I can’t tell you how many times, as a new lead, I sat in a meeting quietly and thought to myself – “Surely someone else must be seeing this problem, too.” No, that someone else is you.

You were promoted into a leadership position for your judgment and ability to follow-through. What may seem obvious to you does not mean it is obvious to everyone else. For high performers, this can be incredibly confusing – but if your instincts are telling you that something is awry, it probably is. Your teammates will most likely be grateful to you for speaking up.

In the early days, it was all too easy easy for me to blow by my one-to-ones. “We don’t have anything to talk about, so let’s skip it.” Or, I would just roll into each meeting unprepared. I was wasting a key opportunity.

As a manager, one-to-ones are the most powerful tool you have in building trust, gathering information, solving problems, and taking action. It’s okay if your first few one-to-ones is uncomfortable – that’s natural. You can strive to improve them over time.

I’ve found these two posts from Lighthouse, on great one-to-one questions, and on handling one-to-ones with your manager incredibly valuable, and I reference them often. I have one-to-ones with my direct reports every other week, and we keep a shared Google Doc on agenda items and notes.

Ugh, I cringe thinking about how awful I was at giving feedback in the early days. I would bottle up the criticism and tip-toe into giving feedback as if it would electrocute my teammate. No! Similar to one-to-ones, giving constructive criticism is a skill you can hone, and one your teammates will appreciate.

Feedback is one of the best things you can provide your teammates to help them improve and grow. And guess what? People stay at jobs longer if they feel a sense of growth and progress. So, the more frequently you give feedback, the more quickly you can help your team grow and improve.

It’s very natural for managers to give feedback on their direct reports, but what about the other way around?

I would definitely recommend creating an anonymous survey, or, asking your direct reports to provide written feedback to you a few times a year. While you are ultimately held accountable by your manager, this feedback may give you insight into things you may have otherwise not noticed, or, confirm that you’re improving the right things. Listen to your team if they’re trying to tell you something.

When you are given a team, or, promoted to become a lead, your relationships with the colleagues around you will inevitably change. Navigating that change is hard. My most challenging reporting relationships have almost always been with teammates that were former peers.

While no two relationships are ever the same, take a moment to acknowledge the situation. Don’t manage your former peers like you would your new hires. Be as transparent as possible with your report, and work with your boss on tactics to create a positive working relationship.

Have you ever noticed that Person A doesn’t work well with Person B? Maybe they are your direct reports. Or maybe, it’s someone on another team. Or, someone isn’t working well with you. As a manager, it’s your job to call those problems out early.

If you let the troubled relationships fester, it will calcify into people not talking to each other, teams not working together, and whole departments silo-ing themselves from other parts of the company. So tackle it early, and build a culture that celebrates collaboration and teamwork. And remember, don’t be a meddler that solves all interpersonal problems at the workplace, you can simply point out the issue to your reports or your peers and help them solve it on their own.

As a non-technical person on a very technical team, in the early days I really struggled with saying “I don’t know.” I assumed I was always the dumbest person in the room, and it was my fault if I didn’t understand something.

But guess what. If you don’t know, chances are, your teammates won’t know. And more importantly, your clients won’t know. If something feels like a black box to you, ask for clarity and you may end up shining a light on something that no one else understood, either. You’ll also set an example within your team – that it’s OK to say “I don’t know.”

This one is so hard, and I still struggle with it daily. My most successful strategy to date is to jot down three things I need to accomplish each week, and make sure I move one of those things forward each morning before I open Slack or P2 (our internal message-board system).

Most inbound will be distractions. Know what you must accomplish each day. Have discipline for yourself because it will breed discipline across your team. I know – it’s easier said than done, but the highest-ranking managers I know have impeccable organization systems they’ve honed for themselves over the years. And, they always have the eye on the big picture. So, I strive to emulate that.

One thing that’s helped me is to define boundaries for myself around meetings. Mondays and Tuesdays tend to be team support, like team gatherings or one-to-ones. Wednesdays and Thursdays are my “deep work” days. I avoid scheduling calls on Wednesdays where possible, and Thursdays are usually only working calls. Fridays are my social check-in days, where I have casual chats with folks on other teams or at other companies, or I have informational interviews with prospective hires. Of course there are always exceptions (especially when I’m hiring), but I try to maintain this schedule where I can.

As a manager, a huge part of your job is to make decisions, and to make them quickly. But do you understand how you make decisions? What drives your instincts? Where do your priorities lie?

It takes a while, but get a sense of where your gut instinct comes from. If it’s driven by fear, your team can smell it from a mile away. If it’s driven by ego, you’ll lose trust from your colleagues. Are your decisions truly coming from what you think is best for the team?

It’s not intentional, but managers often hold onto work way too long. Most of the time, it’s because you don’t want to bother your direct reports with more work. But other times, it’s because you’re holding onto work as part of your lead status.

The most successful team leads I’ve worked with are constantly delegating work to their direct reports, and grooming their lieutenants. Their team stops depending on their lead for All The Things, and become self-sufficient groups with empowered individuals. Those teams are learning the most quickly, including the manager, who has headspace to tackle bigger projects.

It’s super easy to be heads down on your team and looking at what your direct reports are doing. But, are there things you could learn from other teams? Or, are there ways you can help other teams in the organization?

If you are the manager of a team, people come to you to interact with your team. Use that position to build bridges with other teams – cross-team collaboration is often where the best work and most exciting opportunities come from.

You became a manager because you’re a hardworking individual. You go above and beyond all the time. But… watch out. Make sure you are operating at 100% before you give 120% to your work. Your team can sense it if you’re stressed out and overwhelmed, and it can be detrimental to their work, too. As a role model for your team, you don’t want folks to think “on the edge of burnout” is the status quo.

Being overworked prevents you from having good judgement and keeping an eye on the big picture. You’ll be a better, more thoughtful lead if you are well-rested. I’ve found that coaching has helped me prioritize the most important work and stopped me from wasting cycles. As counter-intuitive as it may seem, rest is an essential part of being a productive lead.

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