Slack Best Practices Series: Optimizing Internal Communication & Engagement w/Jacob Gross

In this interview of our Slack best practices series, we speak with Jacob Gross, Community Marketing Manager at Slack. Jacob teaches us how to build an intentional asynchronous culture inside of Slack from the ground up.

Slack Best Practices Series: Optimizing Internal Communication & Engagement w/Jacob Gross
We speak with Jacob Gross, who teaches us how to build an intentional asynchronous culture inside of Slack from the ground up.

Hi everyone! In this interview of our Slack best practices series, we speak with Jacob Gross, Community Marketing Manager at Slack. Jacob teaches us how to build an intentional asynchronous culture inside of Slack from the ground up. Click below to watch the full recording, or read through the transcript at your own pace. We'll have one more interview coming shortly in the series, so stay tuned!

About our Host:

Abigail Caldwell has been a People Operations and HR professional for the better part of the last decade. She's had the opportunity to work with several startups and upstarts, and is particularly skilled in kickstarting and maturing People Operations at companies that have not had it before.

Abigail Caldwell (00:00):

Welcome everybody to our Slack Best practices for internal communication and engagement. While we are going to be talking about overcoming challenges in implementing an asynchronous culture today we have Jacob Gross, with us. Jacob is actually a community marketing manager with Slack (join the community today) and Jacob, would you tell us a little bit more about yourself and your journey up until this point?

Jacob Gross (00:22):

Sure. Thanks Abby. Great to be here. My name is Jacob. I'm on the community team at Slack. Uh, and that really encompasses three main different things. Uh, the user group program, the Slack Community Forum, and then of course we have a Slack community workspace. So I help run these, these programs at Slack help inspire our Slack users and community members, uh, and help folks advocate for Slack globally.

Abigail Caldwell (00:48):

Awesome. And how long have you been with Slack?

Jacob Gross (00:52):

I've been with Slack, uh, a little over a year and a half. Uh, and you know, we've had lots of fun in the last year and a half. We've, uh, you know, brought lots of different programming out globally, uh, for our leaders, for our community members, on the forum for any type of Slack user. So it's been a really exciting year and a half and I'm excited for what's ahead.

Abigail Caldwell (01:12):

Awesome. Well, we'll go ahead and set the stage. So how long have you been using Slack as a tool in your entire career, not just with Slack?

Jacob Gross (01:21):

Yeah, it's interesting, just a handful of years. Uh, historically at prior roles we've used either other similar tools or we didn't use a tool at all. So it's been quite an interesting development in my career in terms of team communication. And of course now that I'm at Slack and I know sort of how Slack uses Slack, I don't know that I can ever go back to anything else. It's, it's only a good thing. Only a good thing.

Abigail Caldwell (01:48):

Yeah, I have to say, excited is probably an understatement of how I feel chatting with you today because I am just absolutely thrilled to get all of the inside scoops of what it's like using Slack while also being an employee. So I'd kind of like to kick off with, wondering for you as a user of Slack, how does it compare to other communication tools like email teams or even something like Yammer that you might have used in prior organizations?

Jacob Gross (02:18):

Yeah, that's a great question. Popular question for sure. Uh, you know, when it comes to using Slack, I like to think of it as my central hub for everything that's integrations, that's team communication, that's file storage, anything and everything that falls under those buckets. So I really think of it as this one stop shop for anything related to work and getting work done. More specifically, if I'm thinking about automating my processes or mundane tasks or daily tasks that I have either independently or with my team, all of that can be done and managed in Slack as opposed to other tools which require you to hop between different tools in order get something done. And so that's been something really cool and exciting, especially being an employee at Slack, is seeing how Slack uses automations like Workflow Builder, for example, to get things done. You know, we always want to get the next task done in order to move on to the next one.

Jacob Gross (03:14):

So, that's been really exciting. The other thing I'll say is, one of my favorite tools of Slack is the intelligent search. Uh, and that's been really powerful for me because if I'm looking for an answer to a question or if I wanted to see if a customer of Slack has reported a certain piece of feedback before that I've recently received, I can conduct an intelligent search in our Slack instance. And I can funnel that down to a specific keyword in a specific channel, which I know that other tools, can conduct searches, but not as powerful as Slack does. And that's something that I found really useful because I don't even need to ask a question to the team. I can find the answer in what is like a knowledge base of information. Uh, and so that intelligent search has really served me and my colleagues well because we see it as this library of knowledge. So that's been really exciting and that really is the int intelligence search as well as automating our tasks and work day-to-day has really been the key differentiator, uh, between Slack and other tools. And I can really see it as that, like I said, that one stop place for everything that happens related to my work.

Abigail Caldwell (04:24):

Awesome. And what are some unique ways that Slack, the tool helps Slack the organization?

Jacob Gross (04:34):

Yeah, I love that it's sort of built into, uh, embedded in the culture of Slack. Uh, you know, we like to take the little sort of nuances and pieces of Slack and build it into our processes overall. For example, whether we're reacting to a message with a set of eyes saying that we're giving it attention or whether we're jumping into thread to start a discussion or do our weekly standup, you know, that really helps, uh, you know, foster a sense of collaboration amongst the team. And it also keeps everything we're doing within Slack. So we're building that culture of that one-stop shop in Slack. Uh, and that's been really powerful for us because we're really able to accomplish what needs to get done without having to jump between different platforms and spaces in order to find what we need.

Abigail Caldwell (05:20):

Awesome. And you were hitting on so many topics that I have for us today, so I'm going try and remember everything that you're saying so I can pull it back in. Before we get into the best practices, the culture and the efficiency, I would like to hear, you know, in your own words, what does an asynchronous community or organization using Slack look like to you?

Jacob Gross (05:42):

Great question. Um, it really, I fundamentally rests on what sort of culture are you building for your team, for your community, anything like that. It really starts at that foundational level. So what are the guidelines? What norms are we building in this space? What culture are we building for us? What are the expectations we have of our members within the workspace? It really starts at that foundational level because, you know, and I'm guilty of this too, we can get really excited and start to create channels and start to create workflows and start to create all of those fun things that is, you know, natural, the Slack. We really have to lay that foundation first, which starts with a set of guidelines for the space. And, you know, it's, it can be a slow burn, you know, building the norms of any space takes time and that's the patience we really need to give ourselves and our team, uh, in order to allow all of that to happen.

Jacob Gross (06:37):

So, building that asynchronous culture is a step-by-step process. It doesn't happen overnight. It's not the flip of a light switch. It really can be a slow burn and that's okay because it really takes time to adapt to everyone's working style to time zones. I know, you know, scheduling and time zones is a big topic these days with folks working remotely. So, you know, we really want to lay that foundation first, and really set those expectations, which will then lead to the norms that we see in our workspace every day. For asynchronous work such as standups, maybe you're creating a, a thread full of Slack clips for folks to jump in with a clip related to their update for the week. Uh, so we really wanna, you know, do those types of things once we've laid the foundation first.

Abigail Caldwell (07:22):

I like that. And this goes right back into our culture and efficiency section. I'm rather curious because every organization has their own culture already built up or being built. Does Slack as a tool have an innate culture that they bring to every single organization that uses them?

Jacob Gross (07:44):

Yeah, I mean, I really have to give credit to, uh, the team that works directly, our customer success team and our account team that works directly with our customers. They're really help expanding the message and, you know, extending the message of the brand, if you will, by embedding pieces of Slack, like reacting with a certain emoji or making sure you're using threads, which I know is a, is a common conversation that's had, or making sure you're conducting that search with the intelligent search that I was referencing earlier in such a way that gets you exactly what you're searching for. You know, using those different pieces to help build the slack culture in a workspace is what will ultimately lead to folks getting work done, moving the needle, moving to the next task, automating their work so that they don't have to worry about it. You know, letting Slack work for you is, is ultimately what it's all about. You know, slack can be your assistant in some ways. You know, setting those automations, building that culture of reacting with certain emojis or building workflows or applying in threads, that will really help set the standard for how work gets done in a space likes.

Abigail Caldwell (08:51):

Got it. And you being in community, how have you in particular influenced other organizations to organize their Slack channels and keep them efficient, easy to navigate for the audience that is actually using it?

Jacob Gross (09:05):

Yeah, that's a good question. I'm part of, uh, some Slack community workspaces outside of work as well, and I've noticed a lot of different great ideas as to how folks structure their Slack workspace. I've seen folks, attach a number to every channel so that their channels are listed in number order or so that users of the workspace can easily find a channel. Oh, it's number five or number eight. I've also, you know, something we adopt internally as well, which I know as a common practice in general is naming conventions of channels. So if, let's say we're working on a project with an external stakeholder and that project is specific to a conference, we will usually at the beginning of the channel name put P R O J proj the name of the external party, and then the name of said project or said conference that we're working on.

Jacob Gross (09:59):

That way it's easy to find that specific project we're working on, or if we're working exclusively with an external vendor about anything that we're doing, maybe we'll do E X T at the start of the channel name to designate. This is an external channel, therefore there are folks external to our organization in this channel. So we know that it's relevant to those folks. Naming conventions can really help, especially if you're conducting a search and trying to find a channel, that'll help keep content organized that'll help keep things streamlined and conversations organized both internally and with your external stakeholders. We use naming conventions all the time internally and it really helps keep me focused on, uh, the specific task or topic of that said channel

Abigail Caldwell (10:42):

That is so clever. I also really like the, folder functionality where you can kind of like create these folders and then p like click and drag the channels into them to kind of segment them out.

Jacob Gross (10:53):

Oh yeah, for sure. Yeah, sections, channel sidebar sections I should say, are really useful. I have a favorites sidebar section. I also recently created one. I started realizing how many channels were being created specifically for conferences or any sort of event. So I created an events sidebar section recently. That way I know which channel to go to for the employees that are gonna be on site for a session that I'm doing maybe, uh, for colleagues that I'm collaborating once I get on site. So, you know, having sidebar sections can really help organize sort of your workflow workflow, not capital workflow builder. They're like the tool but cap, but your work daily workflow. And it really helps streamline and organize sort of where you're at in Slack and where to find information.

Abigail Caldwell (11:40):

Yeah, I love that. So I'm, I'm actually kind of curious. Do you have any guidelines for using emojis or other visual cues in Slack to convey tone or emotion, whether that's internally inside of your own Slack team or throughout communities that you're part of?

Jacob Gross (11:58):

Yeah. Great. Great question. First and foremost, I should just say that when someone shares something in Slack, giving it an emoji, let's say even something as simple as a thumbs up or maybe you're giving it melting happy face, that new face emo that new smiley emoji of the melting face, you know, giving a reaction to something can really make a bigger impact than we think. You know, cause you want to have that visibility, but you also want folks to have some sort of way of engaging with your post, which is where emojis come in to play. And so giving that post a reaction just lets your folks know that you've seen it, that you've engaged with it, that you see the message that they're communicating. Something we've done internally, which I know a lot of folks do, uh, a lot of Slack users do, is we've developed a system for, for looking at a request for example.

Jacob Gross (12:52):

So let's say I have a request where I need, uh, help with an email and I have an email request that I need to work with the email team to help put out for an upcoming event. I will submit that request and they can put eyes, the eyes emoji on that message to say that they've say that they've seen it, that they're working on that message, no back and forth, no confusion, none of that. They just stick a set of eyes on that, which tells me as the person who submitted the request, that the email team is looking into it, they may attach a green check mark also to that same message. Once they've executed that email and it's been sent, of course we can jump into thread and have a conversation about the email. That's always fair game, but it gets, the emoji reaction gets rid of that unnecessary back and forth to say, I'm looking at it and the request has been taken care of.

Jacob Gross (13:43):

And so, you know, maybe you're talking about something completely different in a different channel and you're in a social channel and you're talking about maybe what your favorite musical genre is. Maybe you're attaching some dancing emojis and some, some specific custom emojis to that message cuz you identify so well with that question and you feel so strongly about your favorite musical genre that you're attaching some extra emojis to that message. It's always fun to add a little bit of lighthearted energy. Uh, and it can be, regardless of what the message is, of course we wanna make sure that it's consistent with what's being posted and asked, but you can add a few extra emojis to keep it fun and lighthearted. And maybe you, you may even show some folks some new custom emojis that you've uploaded to your workspace, which may cause them to use those custom emojis later.

Abigail Caldwell (14:33):

Yeah, I I really like that a little hack that I used to use. So I would put a post, a very important like company announcement post and then I would go ahead and set the tone with the emojis that I wanted people to feel. Yeah. And they would to me and they'd say, are you seriously liking your own post? But the goal with it was to kind of like set that tone of this is a positive post. Like I want people to be excited about it and it

Jacob Gross (14:58):


Abigail Caldwell (14:59):

Do that.

Jacob Gross (14:59):

Totally. And actually it's funny you say that on a similar note, if you're polling folks, if you're, if you're creating a poll and you're not using a third party app for polling in Slack and you just wanna get a quick, uh, you know, gauge on how people are feeling, you can use that same approach to create a poll message. So you're writing the message and you're reacting yourself with the specific emojis you told folks to react with based on how they want to respond to the poll. And that not only helps develop a very easy way to create a a, a poll in Slack, but also you're making it easier for your coworkers or your community members to react. They don't have to go searching for the emoji that you told them to use in the poll. You're making it immediately very easy for them to react and respond to the poll, which historically has brought more poll responses, more engagement to polls, folks have higher response rates for reacting to the poll. If you're giving that extra step of reacting yourself, you're already providing what the users need in the poll and it gets taken care of quicker. Right.

Abigail Caldwell (16:04):

So what advice do you have for establishing psychological safety inside of a Slack community?

Jacob Gross (16:11):

Yeah, that's a great question. So, again, it goes back to establishing the guidelines of a space and, you know, something that Slack natively does not have our moderation tools necessarily. You can of course bring in some integrations to help with that. Or you can build your own app to help moderate posts. And, you know, moderating posts could, could come in the form of a workflow where you're maybe, uh, reacting to a message in a certain way and it gets funneled to a private admin channel to help, you know, filter through what's being posted and what's being shared. And maybe you need to follow up with folks directly to help remind them of the set of guidelines of the space. Something we've done in our Slack community workspace is we have a channel called Welcome to Slack community, which is a view only channel, which has a reminder of the list of guidelines, not only what the space is for, but what the expectations of the space are for every user, no matter what type of user they are.

Jacob Gross (17:09):

And so it's really important for a space to be accessible of course, but it's also important for a, a, a space to be safe. Uh, and we really wanna help create that environment for folks. Cuz it can be overwhelming jumping into a Slack workspace, even for a Slack employee, you know, it can, it can be overwhelming. You have all of your channels, you have all the folks reacting and replying and sending you dms. That can be an overwhelming type of experience for someone. So we really want to lay a really good foundation as a community manager. I feel most strongly about onboarding. Onboarding is that first impression. What first impression are you giving a user? And that will help define how the space evolves and is created and ultimately how folks feel throughout that journey, if you will, to help create a psychological, psychologically safe, safe space.

Abigail Caldwell (17:57):

Mm-hmm. <affirmative>, I could not agree more about onboarding. I love when I join a Slack community and I get that message. I have no idea if it's automated or not, but I get that message from someone inside of the community where they're like, Hey, here are some channels that you can join. We'd really like to hear from you. And I really do think it sets just a really positive engaging tone if an organization, and by the way, I'll start by saying I love that the Slack community from last year's frontiers and it is kind of been ongoing. I love the amount of engagement, engagement that is continuous in it. Mm-hmm. Mm-hmm. I didn't expect that coming into it and it now it's literally one of my stapled, slack communities that I always pop into on a weekly basis. But if an organization is creating their own Slack community for whatever it might be, if they're at like 500 members, what are some basic principles to help them get to a thousand or a thousand plus members?

Jacob Gross (18:57):

Yeah, great. Great question. So as we did in Frontiers in 2022, uh, we used our Slack community workspace for that virtual event engagement. And in-person folks could, could use it as well. We really wanted to replicate what that experience would be at the conference in person, but in a Slack community workspace. So we had the help channel where we had a q and a workflow automation built in where folks could submit question. We had a welcome channel where folks had that first entry point into the conference. We had the on the ground live channel where folks who were on the ground could post their photos and videos and, and all of that content. And then we had the fun channels. Like we have a work from home setup channel we have where folks were showing off their desk setups for work from home. We had a pets channel, we had all of that fun stuff.

Jacob Gross (19:49):

And you know, what folks were realizing over time over the course of the conference was that this is the space that is valuable to me because I feel like I'm part of the conference. So let me check out the other spaces of this workspace to see what else is available to me that maybe is not part of the conference, but just as part of the Slack community workspace. And so folks started to realize that I can get my questions answered about Slack certified in the Slack certified channel from the Slack certified team, but I can also attend the conference and I can also go to the workflow builder channel and talk about a use case for a specific workflow that I have. And so folks started to see the value of the space and they started inviting their friends to the space. And we also built the invite link to the workspace in our marketing communication for the event.

Jacob Gross (20:37):

And so that is what help can grow. That's one idea of how it can grow, uh, a community workspace is to embed it in other things that you're doing in your like events, you know, slack. While it is a tool that's built for business, not necessarily communities, which is an ironic thing to to to say, but you can really build in those extra pieces and take advantage of what Slack can offer, like workflows and channel organization and sidebar management and view only channels to help grow the space. And once folks realize once they have an excuse or a reason to come back, that's when you know you've hit the sweet spot is they know that there's a spot where they can get their questions answered. They know that they can connect with other folks and they know that they can view how other people are setting up their work from home space in the work from home setup channel. You know, so we can build in those fun elements for folks as well as engage them in something like a conference.

Abigail Caldwell (21:35):

I can imagine also that, well, we would still need people to run communities run these slack mm-hmm. <affirmative> channels. How much work would you say that is? Is that a full-time job or is that part-time? <laugh>

Jacob Gross (21:47):

<laugh>? Great question. So, and all of these are great questions. I feel like I'm saying great question after all of your questions. But they are, they are great questions and they're important. So yes is the short answer. It requires a lot of admin work to make sure a workspace can be successful, especially if we're talking about a workspace being used for a conference. Something that we've done in the past and that we did at Frontiers is we put a call out internally for folks leading up to the conference for folks to sign up for shifts in the workspace. Someone would manage the workflow, built the workflow that was coming in, in the q and a channel, someone would manage the onboarding when folks were introducing themselves and welcoming them in the intros channel. Someone else was managing the backend of the workspace to make sure that there were no issues.

Jacob Gross (22:35):

So assigning members of your team shifts as if, again, replicating the conference, as if you are assigning them shifts at the conference, you are assigning them shifts in the workspace. And maybe it's channel specific like I just mentioned. It requires a lot of work administratively and I know some folks that are community managers out there that are their full-time job is running a Slack community workspace. Um, but for some folks it's just part-time and for some folks it's not their job, it's just something they enjoy doing, in their free time. So it really depends on volume. It really depends on what the goal is of the workspace. And it also depends on whether, you know, you have 510 or 10,000 folks in the workspace, so it really can vary.

Abigail Caldwell (23:21):

Awesome. Okay. That is really great information. I think a lot of people will be able to pull, some useful bits out of that. And then I know that we're running short on time. I have a couple more questions that I'd really like to chat about. What are your top three Slack features?

Jacob Gross (23:39):

Oh my, well my first one I mentioned earlier was the search. The power of Slack search is unbelievable. It's my favorite. Uh, that's how I find the information I need. The second one I will say is one of our recently released features, which is Slack canvas. Slack canvas is a document layer within Slack that will allow you to share information in a document format, uh, which has been very exciting and, uh, lots of folks are adopting canvas now. And at the time of this recording, it is currently rolling out, so you may have it, you may have it in a few weeks. So Slack canvas, the document layer in Slack, and then the other one, this sounds super simple, but shortcuts for emojis. I love using emoji shortcuts. If I know the name of an emoji, all you need to do is type colon, the name of the emoji, and then it will populate automatically in your message. No need to search for emojis. Sometimes what I like to do, we have like 50,000 custom emojis in our internal instance of Slack. I know it's wild. So what I'll do sometimes is I'll do the emoji shortcut, I'll type colon and then the word smile and I'll see how many custom smile emojis we've uploaded and then I just choose one and have fun with it. So no more emoji scrolling. I always do the emoji shortcut.

Abigail Caldwell (24:57):

I use the emoji shortcut as well, especially for hearts. I'll do like, oh yeah, you know, the heart search. I'm like, hmm, what color am I feeling today? Yeah,

Jacob Gross (25:06):

Exactly. Exactly.

Abigail Caldwell (25:08):

That is so awesome. Okay, last question here. I know we just chatted about your favorite, three Slack features, but can you tell us, is there anything exciting coming down the pipeline for Slack in the coming months?

Jacob Gross (25:23):

Yeah, so we have, as you know, we uh, released canvas recently and more will be unveiled for canvas in the coming months, but we've also released our new, uh, platform for developers and builders who are building on Slack. And a portion of that comes with the new workflow builder. So we have some more advanced features of the low-code tool called Workflow Builder coming out in the next sum, I would say in the upcoming summer months, give or take. Uh, so you'll be able to do more automation with Workflow Builder, get work done quicker. Uh, you know, you'll be able to share workflows as well with a link, which is very exciting. So more to come with that. But if you're looking for more automations and more ways to get work done quicker with your team, stay tuned because the new platform and the new workflow builder will blow your mind.

Abigail Caldwell (26:13):

I love the low-code workflow builders because it makes me feel so smart. <laugh>,

Jacob Gross (26:18):

You and I both, trust me, you and I both <laugh>.

Abigail Caldwell (26:22):

Oh gosh. Okay. So I know that we are a little bit over our time, so thank you so much for joining our call today. Jacob, I cannot tell you how, important your answers are to helping a lot of organizations build their asynchronous teams up. And I do wanna spotlight a call to action as well. In some of our previous interviews, we've talked a lot about the best practices for maintaining culture and evolving culture, but today we talked about the benefits of using different features to our benefits. So I would like to bring the call to action to everybody to explore a lot of these features and how they integrate in with your culture and how you can use them and then set those best practices up so that you set a consistent tone, a consistent way for people to perform and be efficient. So with that said, thank you again, Jacob. It was such a pleasure chatting with you today.

Jacob Gross (27:17):

Thank you, Abby. Pleasure to be here.

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