My Worst Mistake as a Manager – Plato Event

Christian McCarrick Plato

Three great Engineering Leaders (from Datto, Trello, Uber) talk about their worst mistakes as Engineering Managers during the Plato event #1 hosted on May 15, 2017 in San Francisco.

Show Notes:

Article about the panel and full YouTube video

(Transcript provided by Google)

Note: The transcript for this podcast is not very accurate due to the different speakers and the quality of the sound.

Read Full Transcript

[0:00] I getting it to this.
I’ll start off with the quote by Oscar Wilde no experience is simply the name we give our mistakes right and I think that’s what comes from wisdom and lot of people talk about that right we’ve all been here.
Both new and seasoned managers make mistakes it’s not a question of if but when and when are you going to make the money to make your next one.
Important thing though is that we learn from them we learn from their own mistakes and we have all been up to learn from other people’s mistakes and that’s the purpose we’re here tonight,
to help others learn from our mistakes and share our knowledge so hopefully every software engineering manager here can become a better leader I’m going to jump into this now with with the panel’s questions and I’ll start with these for the topic of the day right.
What is your worst mistake as a manager I go left to right in this case you have the microphone that start with u.
So I’ll just categorically say.
Not giving the proper respect to people in a public setting basically it in front of others.
Addressing something in the in a way that wasn’t a constructive.
And that was a million that’s right I think that’s good I’ve been out of cases and how when you do it baby do it right away or after the fact okay.
What are you categorically I would say that my biggest mistake is misplaced Trust.
That’s either trusting somebody too much or not trusting them enough.
And I’m the biggest example of that would be trusting my career Arc to my manager too much.

[1:35] And stand expecting him to to guide me to become a manager instead of learning the things I need to learn and and making those mistakes that they come experience.

[1:49] Has been.
Is super interesting because I recently someone asked me and just in context to what you said recently someone asked me is like a what are your asks for your manager is like some very good question I’m not used to actually making masks of my manager because.
I’m used to just doing it because I cannot trust my manager to do it for me.
Important lesson you need to know what to get from your managers as well but for me it’s been.

[2:17] Assuming that my interpretation of.
A and asked on another person and other team and other part of the organization aligns with what they assume my ass cuz of them so communication is hard it’s just freaking hard no matter how hard you try.
And assumptions if you will on communication that may have happened at some point in time can lead down spiral down and pop of.
Little bit of mrs. assuming wrong intent can lead down the path of misplaced trust and all of that sort of like Spiral into just not achieving common goals at the end of the day.
For me it’s just making sure that his options are very very clear and all parties included as part of continuous learning continuous Improvement and.
Many many mistakes made on the front.

[3:13] Took back to a Benjamin for second you made a mistake as a question of trust at how did you bounce back from that right was there anything specific that you learned that you knew you that you learn better to not do next time.

[3:25] Yeah really just breathe like so sometimes I run into situations where I’ve asked someone to not do something a few times.
And then I see it happen and I’m pretty like go after things like that’s kind of my personality and if I don’t pay attention if I’m not having enough self-awareness that like I’m about to go through what are you doing.
Like yeah I just had that like to write it down.
Talk about an ex 101 text it back okay excellent going to the next thing we’ve all made mistakes and this isn’t necessarily about specific mistake with a butt.
In your career going back is there anything if you wish you could put at one point in time I would do something differently than anything that you wish you could go back in,
and change the other movie sliding doors for the hole in the whole life changes from one one decision to make,
anything that he wants to grab this one first anyone that you might go back and make a decision I mean I got a whole bunch of things but related to work experience right so like literally if I didn’t have this one dude I want to have known like don’t do that.

[4:31] Like it like it sucked and I don’t I wish I could like not do that again but I’m kind of glad I.
Did it in a sense turn from something before it was a massive one right yeah very much the same thing most of these mistakes become experiences there the things that.
That made me who I am and I wish that I could have learned some of them from other people.
But that you don’t watch other people’s mistakes and and I wish that sometimes I had been more teachable and just said okay I’ve got to learn this the first time instead of the fifth time.
But time you got to make those mistakes at some point.
Yeah I’d say that for me it has been becoming more conscious of.

[5:22] Practically asking for feedback because a lot of what’s been mentioned here is like you got to make a mistake and then someone’s got to tell you that he made the mistake.

[5:33] Often times you make mistakes and you don’t know if people don’t tell you until.
Tried really hard now to Cannery body language in fact this morning in a meeting I noticed one of my PM’s had a little bit of a Snappy moment that’s like hey dude what happened like.
Why did you snap in the meeting was.
Was it something I did and we had a really positive conversation after that cuz my my intent was misconstrued and he snapped at the moment because he was super anxious,
and that led to us having a good dialogue and make sure we corrected or intensive each other what are you trying to get out of the situation and that let you like a positive outcome in the end of it so for me it’s become very very important to sort of like.
Read people in the moment so that you can actually ask for feedback because unconsciously you may be doing things that.
Man you don’t just kind of rub people the wrong way.
I think a lot of Engineers have sort of that empathy issue if you will that’s very common.
I don’t know I mean so recently I was talking to someone and then they give me a very very interesting sort of.
Inside if you else like there are three things that you need to look for a plan to City logic and empathy and everyone of us have like one of them is a wobble.
It stings that you’re not super great at and a lot of Engineers apparently seem to have guessed why what empathy is a wobble.
And an essentially like we can’t necessarily tell when people when we rub people the wrong way it’s just kind of reading reading people who better.

[7:12] So what are the things out there so Google most of your hair.
Is it is a project and and you mentioned previously and part of their Project Oxygen and the really went out and I really don’t have a quantitative and I’ll analytics about what makes good managers,
and I found eight points which you can Google online and find them but the interesting thing is that the commonality that they showed for what made to the worst managers that they that they did the polygamist reviews on the worst managers were guilty,
of other day I said it was those who were too busy doing to be managing my continuing to be the technical versus the Teen expert.
So just raise your hand upon anyone here in the early days or continue how many been guilty of doing that trap.
Right knee to anyone in the audience here now how it was raised your hand with you do it today you’ve done it who has done more doing the managing right it’s a it’s a common trap it’s so many of us falling.

[8:02] I’m not I’m not making any tips on.
Is it as much when your first-time manager and you move from the individual contributor to the manager it’s one of the hardest things to do at any tips on how do you.
How do you stop doing and entrust your team to do what you what you know you’re telling them to do.

[8:19] I want to kind of take that a different way absolutely I want to caution don’t go too far the other way one of my worst managers.
I he was I like to call him a master of the system and nothing else he knew all of the right cards to play all of the right people to talk to.
And he would block us at a number of of avenues and would make life hard for us this when I was just new to the industry.
And and so don’t go too far the other way you do you still need to you need to know what you do.
You don’t just run the system but definitely definitely.

[9:01] You need to get the trust and respect of your team and still being able to be getting the weeds and know what you’re talking about if you’re not insert coating every single day.
So when I coach my managers I coach them about 3.
Three things that I index on as a manager process or project product and people.
They’re all equal lover so it’s not like one is more later than the other now of course within a week or month or a year you may / index in one versus the other but they’re all equally.
And when you’re too much into the weeds into the detail you’re probably likely neglecting one of these three levels lovers.
And so what I tend to kind of over and Ducks on,
is make sure you’re contributing on all of these three levels where is the product headed you need to look at the big picture as a manager understand where the product of the team is that it.
But then you need to be able to be in the detail and understand the project level detail so you know what the technical Direction the architectural decisions that our team is making.
How we’re going to be out of milestones and how we going to execute your job is to make sure you execute and deliver.
But then very importantly last finally is also the people which is probably the most important of them all what or how you going to get your people to achieve their goals and make them successful.
And so that’s kind of how I always just go by the 3 P’s and talk about the piece that 3 piece I just stopped going to scrum meetings.
And then eventually I was like well I’m going to jump in man I don’t even know what’s going on in Spanish like literally it depends it depends on your context right you know I’m assuming a lot of ass in here to use a gel some degree or not.

[10:43] Shop organizing teams you got to trust in yourself organized see if they’ll learn to evaluate whether or not that organization is happening at stop organization is happening and it requires having,
engineers at your trust Mustang just blindly give it over to have to develop a rapport and you have to see output that is been,
performance that is not just want to let you know they continue to deliver on that and then you can step away,
still check in now got to have a nice report for like your your Tech lead still got to challenge some of the decisions that you’re making great.
Quick question for you you’ve previously giving a talk about hard decisions and trade-offs one of the things I find to is that with some of my managers,
they’re so afraid of making mistakes that actually don’t make the decision,
red soak to that point you know quickly how would you advise some of these new managers going about making about some hard decisions without being so afraid about your messing up.

[11:40] If you’re afraid to make a decision you need more input.
So if if there is a decision to be made and you feel uncomfortable making it go talk to people talk to people who know more than you.
A lot of times that is the people underneath you.
So I I like to to tell the people that I work with I could not be hired into your job.
Because I don’t know as much as you I am not as good of a coder as you are in JavaScript because that’s what we use a language that I’ve never really spent a lot of time with.
So if you are uncomfortable making a decision go talk to people that that’s your job you talk to people until,
you either get enough people pushing in One Direction or you get enough Clarity that you can say this is the right way to go perfect.
I want for you in your talk that you gave with engineer that rocks right thumb engineer.
Again you talked in and previously talked about the mentor right the importance of getting a mentor early on and it’s something I can believe it to its owner change my career trajectory in the beginning and have one and I was like oh my God this is amazing.
Explain to look at why you know the importance of why you think having a mentor is so important and why you would advise people here to go out and.

[13:01] Yeah it say that a mentor is someone who has no real sort of Tire connection to your day today in a lot of ways and so.
There a sounding board in being able to give you an idea or suggestion or input.
From a neutral no investment insert of the outcome if you will answer.
I don’t necessarily believe in like hey there’s a One Mentor for like.
The rest of Eternity that you have one Mentor that’s going to work with you through the rest of Eternity I try to like optimize for what are the two or three skills that I’m trying to get better at.
For the next year and I tried to optimize for my mentors that can help me.

[13:47] That actually are good at those skills that can help me grow in those areas and so usually I’ll have maybe a couple of Mentor that I’ll meet with even now after having been in the industry for many years.
Can I bounce ideas off of work and lay out a situation I can’t this is what I’m struggling with what would you do in this situation and they would give you some info.
Three fourths of it may not directly apply to your situation and that’s okay but those three for that input will give you insight and perspective into how you should handle the situation that you’re in.
Answer for me that’s what mentors provide their likes there in one sounding boards if you just want to like really bitching complain they can be really productive.
But you ain’t most importantly don’t feel like giving you a perspective.
And perspective is he often received when people have been through their own life experiences.
People on this panel to give you ideas and how you can approach problems sometimes even lay down structure.
Basic how to even approach solving a problem there’s a heart problem you’re trying to solve your hard decision you’re trying to make you don’t really know how to make it they might provide you a structure that will help you make that decision at the end of it.
One very important piece to that structure is what you said get data.
That’s an important piece to that structure and how do you make hard decisions I think mentors help you provide that.

[15:10] Perfect n question for you or actually, if you been I noticed in a past life you did some soccer coaching.
In 30 45 seconds have you felt that that is helped you at all in Indian, during manager and leader your coaching middle school and high school boys at an all-boys Catholic school a lot of patience.
And you know it and it wasn’t a cheap school so it was not only like entitlement everything you can think of.
Your typical engineering perfect so on that note I want to do move into a couple of questions we have from the audience.
I and you know you can kind of pick a straw or go first one the first ones here and I hear this a lot.
How do you read how do you stay relevant right how do you not become the manager right they do the character of the manager who doesn’t know anything I was talking about you become a suit right how do you stay relevant right anyone to pick this one up.

[16:09] Going to get your name wrong is it Shivani Shivani I didn’t Let It Rock Sweet reiterating your point.
Management is an entirely different skill-set from coating so if you’re doing Bowl.
Then you have to stay relevant encoding if you’re not and you’re just doing management stay relevant and management leave the coating up to everybody else,
Benjamin one thing I would add to that is it depends on your contacts so I 100% agree,
you have to own management if their own leadership which is what we’re talking about earlier about making tough decisions without all the data that’s that’s being a leader get the own that button like in my contacts,
if I if I don’t have a clue technically I don’t get the respect of the engineer’s so what I do is I I I conduct all the interviews regularly review all the cold samples that come in so I’m staying relevant in measurements.

[17:03] Sure you got one going to answer I differentiate between code and architecture assign decisions and usually I never 60 people,
I’m not going to be in the cold details but.
What I do I’m still very very in tune is in the architecture of the systems and then I joined a new team and routinely if you owe I do architecture of you.
I just try to have the team tell me about what they work on such a really good cuz Engineers love talking to their skip level on,
hey this is the cool thing I built it’s a really great great way to get Engineers to feel like they’re talking to their skip level but also more importantly gives you a very good insight into what the systems are in,
how they work well together,
and you can abstract out and say okay why did we make certain design decisions on this particular product that are so uniquely different than this other product that are so similar,
so it really helps you identify patterns going to give it to you too cousin to keep in mind this is a very interesting I don’t think it’s enough.
Credit as you become a manager becomes more and more important to manage up right managing up and managing out to all the questions is your how do you manage your manager and it was one of the biggest mistakes I’m on the panel but it was not properly managing my manager.
How about you there two aspects to it so one is how I like to be perceived so that people who.
My skip level how they feel about coming to me.

[18:34] And then how I manage my manager you’re very different but for folks who are my skip level.
I try to the only thing I try to strive for is the comfort and Trust.
That they can come to me with anything that’s the only thing I strive for it if I have achieved that comfort and stressed that they can come to me with any problem that’s it that’s.
I thought means that they will if they have a challenger problem they’ll feel comfortable coming and talking to me but I’m managing my manager it looks very very different because.
At that point in time I’m trying to optimize for what is it that they want to hear the most about how do I get them to talk the most because honestly people love to talk.
You can see that right now so yeah you want to get your skip levels talk more and when you’re in a meeting with them you want to make sure that you understand how they think.

[19:30] Benjamin yeah absolutely I believe that my number one job is to make my manager’s job easier.
I’m I didn’t used to think that I used to think I had to fight them and stand up and you know I always contradict what they’re saying so once I realize that cuz I got smacked down too many times for doing the other,
ident a lord how I interact with my manager who’s Wicked Smart Way smarter than me,
and I I learn them so I got to a point where I actually understand before he even asked me what he’s going to be looking for and over-deliver on that before he asks it I send it to him,
and things of that nature.

[20:12] I concur oh perfect I think that’s about kind of the time for the session here ranting up just about on time owner thing.
Are you I appreciate your time up here from here.