Management Mistakes I’ve Made (So You Don’t Have To) [Video]

I was reading one of those management books recently when a sentence in the opening chapter gave me a visceral reaction:

“Failure in a new assignment can spell the end of a promising career.”

What?! Though the book itself was great, I could not disagree more with this sentence. Failure is a key to getting better, and in fact, my employer has a page in our handbook called “Made a Mistake? It’s OK — We’re Human, Too,” which includes this paragraph:

“The way we see it: Every failure is an opportunity to learn — you have a chance to start new habits with a motivation that will be difficult to recreate, so if anything you should start committing more than ever.”

“… Another way of putting it: ‘Get back on the horse that bucked you.'”

Last October, I presented at a conference on the mistakes I’ve made in managing a growing team. Being a first-time manager can be really hard (see this post I wrote four years ago), and as I grew my team from 8 to 60+ people, everything was a first for me.

I’m usually a very comfortable presenter, and even though I knew that the audience was full of kind and wonderful people, I was intimidated. Many attendees had impressive careers, or had managed teams (or businesses!) that were significantly larger than mine. So, imagine my complete shock and surprise when I received some very nice tweets post-talk!

It made me realize that no matter where you are in your career, these mistakes that I shared can resonate. The conference had the amazing White Coat Captioning team live caption my presentation, so below please find the video, slides, and edited transcript. I hope you find it useful.

As for the conference itself – if you haven’t checked out Monktoberfest, please do! It’s one of the best conferences I’ve ever attended, and I get value out of it every year. I love that it’s a small group, with topics you wouldn’t hear elsewhere. The only way I can describe it is: “some very kind and smart people in technology gather to talk about interesting things and enjoy world-class food/drink in the beautiful city of Portland, Maine.”

Hello! Welcome back. It is so awesome to be here. This is, I think, my third Monktoberfest, and I remember standing in the back last year, thinking: All right, I’m going to pitch, I’m gonna do it, I’m going to pitch. So I’m really excited to present to you. My name is Steph Yiu, I grew up in Singapore, and I currently live in Boston, Massachusetts. About 7 years ago, I joined a company named Automattic, where our best-known product is I was hired as an account manager for a new team called VIP and we service large customers that want to implement WordPress. 

Fast forward 7 years, and we are an Enterprise WordPress platform and I learned to manage a team on the job. About a year in, they said, “Steph, do you want to manage a team?” And I said “Sure!” And then that was about it. Good luck, go figure it out.

That team started out as eight people. Today my team is 60, and my team is everything post sales, so it is when you sign up with us, my team comes in with onboarding, implementation, account management, engineering support, and support.

The reason I’m giving this talk is because my first couple years as a manager were really hard. I felt so alone.

One thing that I didn’t mention at the top was that our entire company is distributed. So we have no offices, so I was really figuring this out on my own behind a laptop.

On top of that, there weren’t a whole lot of female managers at my company, either. So I was looking for role models and not really finding many. So this talk is about all the mistakes that I’ve made so that you don’t have to! … Or at least if you’re going to make them, you know that someone else has made them, so you don’t feel so bad, and also that you can power through it and know that you can get through to the other side.

If you’re a female manager, just hopefully seeing that there are other female managers out there who have also struggled and just knowing that it’s really fricking hard. So we’re going to dive right in.

There’s a lot of mistakes, so we should get going.


So the first mistake is not understanding what drives your organization’s decisions. When I accepted the management job, I don’t think I had any understanding of how decisions got made at the executive level or how our CEO was making decisions. When your org thinks about how they, for example, add head count to your team, how do they do that? Is it mission-driven? Is it values-driven? Retention-driven? Revenue-driven? Understanding that empowers you and you know what levers you have to affect change and if you don’t know, ask your boss.

The other mistake I made – and I really like that Hadley talked a little bit about this this morning in his presentation – was understanding, mentally, in your personal experience, what drives your decisions. Is it ego? Is it fear? Is it truly what’s best for the team or what’s best for the org?

I have made plenty of decisions based on fear, not knowing what was going to happen and being like, “Well, let’s figure this out.” When you do that, your team can see it from a mile away, even though you try to hide it. So just understand and recognize where that decision is coming from, and know that sometimes it might not be from the best place, but when you figure that out, you can own up to it.

So I told you about a year in, I became a manager, and I felt like I had to put on this bravado, like, Cool, now I’m an a manager, I need to know everything and you’ve given me this new title so I should be brave and just figure it out. Turns out you really should lean on your boss for help.

What are you responsible for? How do you improve? And what is your priority?

That information is really good to know. You’re trying to figure out what your success metrics are. And here’s the thing about these mistakes. You make them over and over again. Because I actually made this mistake on Monday.


I had spent the entire weekend super stressed out and trying to problem solve something that I couldn’t figure out the answer to, and finally on Monday – my boss and I have our check-ins on Monday – I raised my hand, and I said, “Boss, I’m stuck, I need help.” And I was churning and freaking out and whatever. And his response to me was, “All right, let’s figure it out. I don’t really know the answer, either.” And the weight just lifted. So lean on your boss. It’s their job to support you, too.

Mistake No. 3: Assuming your suggestions are obvious.

I can’t tell you how many meetings in the early days, when I wasn’t super-confident, that I would be sitting in meetings and thinking: Surely someone knows that something’s off here. Right?

Surely someone knows that this scope is ridiculous, right?!

Turns out, you were hired or promoted because you have really good instincts, and sometimes you may see things in a room that other people don’t. High performers especially don’t recognize this. High performers kind of think that everybody sees the world the same way they do. So just state the obvious and be direct about it. Don’t be “Oh, I kind of think, whatever,” say “Hey! This scope seems ridiculous. Let’s think about this.” When you do that, you empower the room to see your perspective as well, and troubleshoot.

This one, I still struggle with. Avoiding “I don’t know” because it’s really embarrassing. Sometimes when you feel like you need to know or maybe you’re leading a big team and you think you should know and sometimes you have to be like,” I don’t know.”

What is amazing about saying “I don’t know,” when you get the courage to say it, is that it can prompt for clarity for other people on the team who also don’t know. It can also be amazing because your team might come back to you and say “Hey, we know, let us help you!” And that’s what’s really powerful, and especially in companies that work closely with open source, you know how powerful those voices can be in helping you find the right path forward.

Mistake No. 5: Starting your day with inbound. I had to work really hard to quit doing this. And the only way that I was able to do this was to put my phone to sleep at about 8 or 9:00 at night, which means that at that point my phone goes to bed in my office, and then I go away. I don’t touch my phone until after I brush my teeth in the morning.

And the reason I do that is because most successful managers and leaders that I know really try to only accomplish one significant thing a day. And maybe even one significant thing a week.

Your job is to determine the priority for your team, and lead from a place of clarity. So if you wake up first thing in the morning, and you’re just in Slack and Twitter and email and everybody else is driving your priority, it makes it really challenging for you to lead with a clear head space.

Your team depends on you for that clear head space, so really try to give yourself time. I think everybody does this a little bit differently, but it does seem a common trait is put the phone away. It’s distracting!

Another mistake that I made early on was rolling into my one-to-ones not prepared. Who here has done that because I’ve done that a whole bunch.


So guess what? Your teammate can help you prepare for your one-to-ones, it doesn’t just have to be you. The way I do that is we have a shared Google Doc between me and my teammates, private between the two us. We take rolling notes in that. There’s a date at the top of that, and you just add agenda items. I have in my Firefox browser a bookmarked folder of all my one-to-one Google Doc notes. So, I’ll click on one titled “Steph and Paul.” And throughout the week I can just drop in ideas and things I want to make sure I check in with Paul on. I check-in with each of my direct reports every other week. They can add stuff to the agenda, I can add stuff to the agenda. They can take notes in that Google Doc and I can take notes in that Google Doc. It becomes a pretty collaborative space.

More than anything else, I didn’t realize that one-to-ones were a skill that you can hone and if you Google it, there’s a million amazing questions that you can glean from other people and things to ask. What you’re trying to do is understand your teammate, and you can collaborate on a path together. 

I remember the first time I had to give someone tough feedback. Who here remembers the first time they had to give someone tough feedback? It’s so hard, and you feel terrible about it, you feel like you’re going to ruin their day and they’re going to leave the meeting crying. You think they’re going to talk badly about you behind your back and you just feel like it’s going to be the worst thing ever.

Now that I manage managers – I see that the managers who are really comfortable giving feedback to their teammates create high performing teams. It’s because the manager is giving their teammates the opportunity to get better. So really, feedback is a good thing.

And if you hold back from giving feedback, that’s the bad thing.

One thing we always talk about when my managers and I work through feedback is that you always try to think about what would be best for the teammate. You’re not giving them feedback to make them feel bad. You’re really thinking about: How can I get this person to be a higher performer? More productive? More creative? More focused? When you frame your feedback from that space, your teammate will be more comfortable because they know that you’re trying to help them.

The first time I asked for feedback from my direct reports, I was terrified. We have this anonymous tool at our company. You can write feedback questions and send it to at least 10 different names, and they can send it back anonymously. You’ll want to be specific, like, “Hey, I’m working on my X skill. Do you have feedback for me on how I can improve on this?” Then your teammates, your direct reports, your skip levels, they can write feedback back to you and it will be anonymous among that group, so hopefully they’ll be more honest with you.

I always think of feedback from people who report to me as a data point, not a decision maker. It helps inform me on my leadership style. It may not always be positive but I don’t want to immediately make a change all the time, sometimes it’s just a data point. But it’s really informative. Because your boss doesn’t always see what your direct reports see, so it’s helpful to get feedback from them.

This has been one of the most challenging parts of being a manager. Which is that at some point in your career, you will be working alongside a friend, or a peer for multiple years, and then one day, you will choose a manager track and they will not. Or one day you will get promoted above them, and you may not know all the details of why you were selected and they were not, but it can become a very awkward and somewhat tense situation. I think the best thing to do is to not turn a blind to it and not to try to manage your former peer just like you manage everybody else. If you can be, be honest with the person and say “Hey, this is a little uncomfortable, let’s figure this out.” If you can’t be honest with them, seek help. Get help from your supervisor or a trusted peer. It can be a really fraught and stressful situation.

Another mistake that I’ve made in the past is letting troubled relationships fester throughout the organization, and not necessarily people that report directly to me. For example: you have a small team and maybe you have one person in product and one person in marketing and they’re just butting heads and not getting along. If you don’t take care of that relationship early, what might happen is when you become 100-person organization, that original relationship calcifies, and your product division and your marketing division might be completely siloed from each other.

As the lead and a manager it’s your responsibility to call that out and let their supervisor know that “Hey, something’s going on here and it’s preventing these two departments from collaborating with each other.” Ultimately, all of you are working together toward a common goal, so turning a blind eye to that can be detrimental to your organization.

This one I do not intentionally. But sometimes it just happens. I think I did this last week. Hoarding your work and your status. Basically what this means is that you have a bunch of stuff on your plate and you’re refusing to give it to the people who report to you. For me, oftentimes I do that because I don’t want to overload my teammates, but what I’m forgetting about is that it’s an opportunity for my teammates to grow and it could be a really great challenge for them.

The other thing is that the best managers that I’ve seen are always grooming their replacement. You’re always working to have someone who’s able to step into your job, maybe at at 100%, but maybe at 60 or 70%, to take over for you if you move on to the next thing. It gives you the head space to start working on the next problems or the next challenges in a way that if you’re always heads-down and your plate’s too full, it prevents you from looking ahead.

This one I do all the time, being too helpful. It means that when I see things slipping between the cracks, I kind of swoop in and try to rescue, when in reality sometimes it’s not always my responsibility. This is a problem because it can really hold you back, and you may end up doing things like what people “office housekeeping work,” instead of strategic and valuable work.

One phrase that we use a lot across our team is the “Go where you are rare.”

Look for places where you are the only person that can make that decision, or the only person who can move that forward and work on that. It’s been really hard for me to recognize this sometimes, and I think it’s actually held me back for a long time. So this is a mistake I’m always working on.

Has anyone here heard of the concept of first team? Who here has heard of it? Awesome.

So this was actually shared with me by my boss, and I really love this concept. Essentially, I run the support and services org, and I report into a team that has a head of engineering, head of revenue, and head of marketing. We all report into the head of our division.

And who’s my first team? It’s not the support and services team. It’s the team that I’m part of. And so marketing, support, engineering, sales – we are working together as a group, trying to move things forward as opposed to my priorities being just my team.

What happens is that whether it’s product or engineering or marketing or support and everything else, we’re collaborating with each other. We move our business forward, and hold each other accountable. If I need something from my product team, and they’re not delivering, I need to make sure that they know that from me, and I’m not just focused on shipping things with my own team. This first team concept has been really powerful for me and I’ve taught my managers to also subscribe to that, so that their groups can collaboratively work with each other, as well.

The last one is going above and beyond all the time. Because sometimes you’re chosen as a manager because you’re a high performer, and you’re just working crazy hours and just completely underwater all the time.

Your team can totally tell when you’re under water and you’re scattered, and it may not be the best role model for them. If you’re running on fumes, it’s really hard to be a good manager.

Self-care is an essential part of managing, which means: getting help from your boss, taking breaks, and planning vacation well ahead of time so you don’t blow through summer realizing you didn’t take any vacation. For me it’s meant working with a business coach. Figure out the things that you need to replenish you, so that you can be the best teammate that you can be. Thank you.


You can find more of my posts about remote work, communication, and other topics here. Featured image by Barton George on Twitter.