36: How To Work

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This is a podcast episode titled, 36: How To Work. The summary for this episode is: If you liked this episode, we bet that you’ll love our blog content. blog.drift.com/#subscribe Subscribe to never miss a post & join the 20,000+ other pros committed to getting better every day. --- There's one thing no one tells you about your career: how to work. So, this week on Seeking Wisdom we're going to talk about how to work. We talk about how to run your 1:1's, managing up, and the importance of proactively communicating and showing your work. You could call this Carry The Water Pt. 2 (Episode 19; go back and listen). Come hang out with us at seekingwisdom.io and on Twitter @seekingwisdomio. Follow David (twitter.com/dcancel) and Dave (twitter.com/davegerhardt) on Twitter.

David: Woo, woo, that's the sound of the police.

Dave: I wish people could see you. You're in your travel gear.

David: I'm all sweat suited up.

Dave: You're catching a 9: 00 PM flight to Dublin, so you're in the sweatsuit. So today on Seeking Wisdom, we're going to talk about how to work.

David: Show me the money. Let's go.

Dave: All right. I want you to tell the backstory. We were having a conversation at lunch the other day about how to work. And this is something that you've seen this over the years. This could be almost a little followup to carry the water, but this is one of those things that you have to learn it, and it's also one of those things in your career that is so important, but nobody ever tells you that it's so important, how you actually work.

David: And why do you know how to do it?

Dave: Because that's how I started working. The first boss that I had, at the time, he drove me insane, and he always wanted to-

David: What did he do?

Dave: ...review every email and highlight this. And every time I'd write something, this was before people used Google Docs, just Microsoft Word, every email I got from this guy would be feedback and track changes.

David: That's good. So it's feedback driven.

Dave: Yeah.

David: Did he do it forever or was this-

Dave: No, it was a couple months. I was young, 23, and I didn't know anything.

David: Still young.

Dave: Yeah, yeah, of course I'm still young, but I mean, this was the first job I ever had. And at first it was hard because you get this thing back and it's just bleeding red. I spent time writing this thing and it's just blood red, all comments. But once you realize that everything this guy was saying was right, it changes how you think about things. So that's where this whole thing started from, but there's a bunch of different topics that I want to talk about with you today.

David: Yeah. It reminds me of this book I was reading, which I forgot the title of, of course, because there's so many. But it's a book by Colin Powell. I think I mentioned it. There's this part in it that I thought was interesting that reminded me of your experience, where he said whenever he would bring on a direct report, and I believe this is when he was Secretary of State. If you don't know Colin Powell, he was Secretary of State, he was the head of the joint chiefs, chairman of the joint chiefs and a, I believe three star general. So, he would tell people who came to work for him directly that for the first amount of time, let's say it's a month. I forgot what the timeframe was. Well, the first few months, that he is going to be all over them. He's going to be on top of the night and day and it will be hard for them to breathe. It will be relentless in terms of giving them feedback and what you were saying, being in their shorts. But his goal and the reason he was telling them this was that this was his form of training and getting them used to his kind of feedback and learning how he worked and how he ran a group or department or organization. And then over time, that he would pull himself more and more away. And then finally, he would hardly be involved in what they were doing. And I think he said this for a number of... Well, first I think he said it because he wanted to make clear that when these people were suffering through this, that they knew there was an end in sight.

Dave: Right, this is going to be over.

David: Yeah, man, this guy won't leave me alone. But that this was his form of training.

Dave: Well, it's also smart because he set that expectation up front. Because he went out and said that, you don't feel like, even if he is micro- managing, you're not like," Man, this fucking guy." It changes the-

David: He won't let up.

Dave: Yeah.

David: Yeah. So it was his form of training and it was really clear feedback, relentless, and then let up. But usually what happens is either someone micromanages forever, and so never stops, they never set that expectation, or they don't give you very detailed feedback and you're left guessing and assuming things and then getting negative feedback later on. So he really compressed the feedback loop, as we talk about it here, and put that upfront and then set expectations for when he was going to pull out.

Dave: Yeah. But, okay, here's the thing that I want to talk about and have this podcast is there's this whole layer of work, there's this whole layer of things you have to do at work that actually have nothing to do with the stuff that you're creating. So if you're a designer, if you're a marketer, if you're an engineer, part one is doing your job and creating the things you need to create. But part two is the way that you share your work, show your work, the way that you manage up and manage your manager and have one- on- ones and proactively communicate, there's this whole other layer of work that I don't think a lot of people tell you about earlier in your career. And oftentimes a lot of people miss that, because if you join an early stage company right out of college, you don't always have the structure in the process. So the people that I know that have had it have either worked for somebody who has managed them that way, or worked at a bigger company where there's more process.

David: That was very structured. Yeah, and process driven.

Dave: This is something that you talk about all the time, show your work, show your work, proactively communicate. It's something that we're really big on.

David: Yeah. I think you nailed it right there. I think it comes down to communication, and that's the part that everyone's missing about their jobs. So they know their craft. Let's say it's design, let's say it's marketing, let's say it's engineering, whatever it is, finance, they know that craft, but they've never been taught and they've never been in a process where they have to learn not only to communicate to their boss or the group or their investors or whoever they're working for. We all work for someone at the end of the day, including all of us right here. We have investors to answer to and we have lots of people to answer to.

Dave: I have you to answer to.

David: And I have investors to answer to. See? It's endless.

Dave: Yeah, we're good. We're good.

David: And they have investors to answer to. So either communicating to the person that you're working with and communicating to the people around you, and those might be people in your group and then people in your company across your organization. So you're never taught to communicate across and you never communicate to other people. You just assume that people know what you're doing. You assume that, oh, I'm doing my work and I'm getting it done and people should just know, but people shouldn't just know.

Dave: No, it's funny. September 1st we had two new people join our marketing team, Amy and Caitlyn.

David: What's up?

Dave: They're going to listen to this. They both do an amazing job of sending me things that they're doing in direct message on Slack. And it's just like a training thing. They both are sick of me saying it probably, but it's like," Hey, can you share this update in the marketing channel?"

David: Yeah, so everyone on the team can see it.

Dave: So that everyone... And it seems like such a little thing, but it's so important just to share, hey, here's what I'm doing.

David: Yeah, because most people do what they were doing, which is great, which they got half of it right, which is they're going to communicate to you. But the other half that was missing was how they communicate across the team, because across the team, those people may look like a black box. And I think the whole point of this talk that we have is you want to avoid looking like a black box. You want to be transparent about your work. You want to show your work and you want everyone around you ideally in your company, as well as the people that you work with or for, to know exactly what you're doing.

Dave: The other thing that happens all the time I think, is some people are really good at... They're starters. They'll be like," All right, here's our plan. Here's our sales plan for this month. Here's where we're going to do X, Y, and Z," and there's a Wiki post and there's Slack messages and all the right stuff happened, but then you're two weeks into the month and there's no follow- up.

David: Yes, follow- up is the key. And everyone's left wondering, are we doing it? Is this person handling it? Is that team handling it? What is going on? And the worst thing that can happen is for people to wonder. Because if they wonder, then that means you didn't do a good job doing your communication.

Dave: You said the exact thing as an employee, the number one thing that you don't ever want people to do is wonder.

David: Yes.

Dave: And whether that's your boss or whether it's the people on your team. So that's why one of the things that we harp on so much is the proactive communication. And the reason is-

David: Yep, over communicate.

Dave: Yeah. And it's easy for you to send me a message and remind me and be like," I got it." But I don't ever want to hear from you and have you say like," How's that thing, how's that thing, how's that thing?" It's your job as somebody who has a manager to make sure that they don't have to do that. This is like the whole art of managing up, is getting ahead of that.

David: Because then it feels like, oh, this is someone who really owns it, who's got it. I know the state of it. I don't have to worry. I never have to check in with this person. They've just got it under control. And that is so rare.

Dave: Okay. So this is your fifth company, I think. Who knows. Who knows.

David: Who knows. Unknown.

Dave: How do you as a founder and a CEO, how do you instill that in a company? Because it's really hard. Even at my level right now, it's hard to teach that. How do you set that tone?

David: That's a good question. I think one is selection bias. So you try to select people who are naturally this way. So aside from that, there's always going to be other people who may not have learned this yet, and so you need to help them learn this. One way could be the annoying way, which is like the Colin Powell way, which is I'm just going to be in your shorts enough until you get frustrated enough that you pick up on the pattern. That's not the most optimal way, but that is something that happens, and you just keep asking the same question of these people and hope that they magically get it at some point. Now, some of them do and some of them don't. And then for those that don't, you need a more formalized process. You need to train them. You need to do what you did with Amy and Caitlyn who joined your team, which was to say," Here's our playbook. Here's our standard for performance. Here's how we do things." And then even though you did that, you have to constantly remind them, say," Share, share, share, share," until it becomes a default state.

Dave: Yeah. And it's interesting. It depends on where you come from. Our company, we're always sharing ideas on the Wiki, and it's like," Oh, put it on the Wiki," and that's a hard behavior for new people to learn, which is if you're thinking about something out loud, it's just good to write it down and share that publicly. Another part of this I want to talk about you with is one- on- ones. I think this is a big... You have a post on our internal Wiki that's a new hire playbook. And it's like," Here's your one- on- one." What's the number one thing people get wrong with one- on- ones?

David: That it's their one- on- one to drive and their responsibility to own the subject matter, and the fact that the one- on- one happens and not the manager's to own.

Dave: So, you don't show up in that meeting and say," Okay, manager, what's up?"

David: Exactly. Or have it be unstructured. Just show up and just chat about random things or just catch up. Your manager will probably just go along with that, but it's really your meeting to own. This is the meeting that you're using to make sure you're in sync and to make sure that you're progressing in your career. This is your meeting.

Dave: Yeah. I don't think enough people take the one- on- one meeting seriously enough.

David: No, definitely not. Dave does.

Dave: Yeah. I mean, that's a type A, super type A organized thing for better or worse.

David: Tell them about your list.

Dave: First of all, this isn't just me. I read a bunch of people in books.

David: I'm sure.

Dave: Because books are great.

David: Yep.

Dave: That have mentioned this. So in my Evernote, I have a note, and it's called DC one- on- one, and that's just my note. So you and I talk all the time, but there's certain things that aren't day- to- day things I need to ask you about or bother you with. I'm not just going to randomly send you a Slack message and talk about our marketing strategy for the next month. That's not productive. But if there is something that comes up, comes to my mind, I put it in this DC one- on- one file. And that way, A, I get it out of my head and B, it has a place to live. And then every time before we have a one- on- one, I have a list of all these things that I wanted to go through.

David: Super productive.

Dave: And a lot of the times, those shake themselves out. I'm like, I have notes in there. I'm like, oh, we ended up talking about this. Don't need to do this. But it's just a nice way to A, have an agenda for that meeting and B, get those things out of my head so it's not always driving you crazy, and I'm not like," Oh, we're not going to talk until next Tuesday at 1:00. I've got to save this note."

David: Yeah. I think agendas, which you mentioned, they're an underrated tool to use. And another person on our team, Will, what's up, does a good job. I was just giving you crap about using... He uses Evernote too, to have a running list.

Dave: Well, I mean, yeah. You're a out loud thinker.

David: Yes, out loud. So true.

Dave: But yeah, it's a simple thing, having an agenda and then understanding that as an employee, this is your meeting. This is your time to say... Because I think what a lot of managers want to be is a roadblock remover for their employees.

David: Totally. That's the best state, for sure.

Dave: So if you can come to that meeting with a list of, hey, here's all the things. And then you're like," Okay, how can I remove these roadblocks?"

David: This is true of a lot of relationships. This is like investors and board members, advisors, all those kind of folks. They want the same thing, which is come with an agenda, come with a clear ask. What's the ask? What do you need? And then if they can, they'll try to help there. Otherwise it seems like a little bit of a waste of time. It's good to connect socially, but it's a waste of time if there's no, to use an old school term, action items, for the meeting.

Dave: Yeah. Or what's going to happen is you're going to shoot the shit for 30 minutes and then you'll be on your drive home, and you're like," Ah."

David: Yeah, I forgot.

Dave: "I needed to ask him about that." And then you don't have full attention. You've got to do it over email or Slack. There's something about the dedicated time of a one- on- one that is super important to have an agenda for.

David: Definitely.

Dave: Yeah. All right. So that's how to work.

David: That's how to work. Let's get to work. Will... I mean is Will-

Dave: Will's on your mind, man.

David: You know why Will's on my mind? Have you ever seen the movie Good Will Hunting?

Dave: Of course.

David: So I was reading through some of our five star reviews. Thank you, people. You know who you are. And someone compared me to Good Will Hunting.

Dave: In what sense?

David: I don't know. She said, it was a she in this case, said that I was... What the hell did she say? That I was the Good Will Hunting of whatever it is I do. And I thought that was an interesting thing.

Dave: That's great, that's great.

David: Because it's true.

Dave: I love it, man.

David: It's true. I think she was saying that as a street kid, which is true.

Dave: A street kid. And now you're at Harvard or something like that.

David: Yeah, yeah, yeah, I've done something.

Dave: So where are you off to? You've got some travel coming up.

David: I'm going to Dublin. I'm going to see my people in Dublin. Get ready for me, Irish. I'm coming for you.

Dave: And you're speaking.

David: I'm speaking at SAF Stock this Thursday, which I don't know the date on the calendar, but this Thursday this week. And then next week, I'm off to London to go hang with my Brits and a talk at Mind the Product.

Dave: Nice.

David: So hopefully, I'll see you at one of those two events. If you do see me, shout me out. Let's hang, let's party. I go to bed at 9: 30 though. So we got to make it early.

Dave: And do me a favor. Go follow David on Snapchat.

David: I'm blowing the Snapchat up. DCancel.

Dave: We're trying to run a little test. We're trying to see is Instagram where it's at? Instagram Stories has kind of been blowing up a little bit.

David: Also DCancel on Instagram. Follow me both places. Let's see which one wins. Pretty interesting results so far, which we'll share in another episode.

Dave: Cool. So that's the deal. Seeking Wisdom, how to work, five star reviews.

David: Only.

Dave: We'll take them.

David: Irish, I'm coming for you.

Dave: Peace.

David: Shout me out. Let's hang, let's party. I go to bed at 9: 30 though. Woo, woo, that's the sound of the police.


If you liked this episode, we bet that you’ll love our blog content. blog.drift.com/#subscribe Subscribe to never miss a post & join the 20,000+ other pros committed to getting better every day. --- There's one thing no one tells you about your career: how to work. So, this week on Seeking Wisdom we're going to talk about how to work. We talk about how to run your 1:1's, managing up, and the importance of proactively communicating and showing your work. You could call this Carry The Water Pt. 2 (Episode 19; go back and listen). Come hang out with us at seekingwisdom.io and on Twitter @seekingwisdomio. Follow David (twitter.com/dcancel) and Dave (twitter.com/davegerhardt) on Twitter.