How a professor turned his passion for Slack into an old-school guide

Slack for Dummies author Phil Simon shares tips on switching from email to Slack, his favorite apps for Slack and more

Two people pasting signs on a wall, one of a cat with "Plz" written below it.
Image Credit: Ping Zhu

In 2017, business professor Phil Simon stopped responding to his students’ emails. Instead he’d say, “Ask me in Slack.” Not everyone loved this response, but eventually he successfully migrated all out-of-classroom communication with students to channels. Forcing them to collaborate in Slack was his way of preparing them for work life after university.

Now he’s helping slower adopters, like his professorial ex-colleagues, learn Slack. Simon penned Slack for Dummies, a 385-page tome on what he calls “a better way of working.” It’s less a printed version of our Help Center and more a power user’s quick start tutorial and an expansive list of essential features. Simon recently sat down with Several People Are Typing to discuss his motivation for writing Slack for Dummies and how to overcome challenges for email veterans trying to “get” Slack.

Slack: What inspired you to write Slack for Dummies?

Phil Simon: Whether it’s through books, webinars, keynote talks or seminars, I like to think I explain things well to people. If they don’t fall in love with Slack immediately, like I did, then a Dummies book makes it pretty simple. Even though your Help Center is great, there are people who want a linear way of going through it and need something physical. Hopefully, the book achieved that.

Slack: Can you describe what the first weeks of using Slack were like for your students?

PS: For the most part, the [students] adopted it because they really had no choice. When I first started using it in the classroom, I simply said to them, “We’re not using email. I’m not going to respond anywhere else but through Slack.” And I’d reinforce this by designing activities around Slack, like with in-class polls through Simple Poll or Polly, so eventually they saw that it wasn’t an optional tool. It was the hub of the whole class. Overall, it went well with the students.

Slack: What are some of the biggest challenges people encounter when adopting Slack, and how do you help them get past those?

PS: Some people struggle because there’s not a one right recipe for Slack. For example, some people in higher education ask, “Do you have one workspace for every class or do you combine them and have one channel?” There are pros and cons to each one, and that flexibility is both a blessing and a curse. Hopefully, that comes through in the book and readers understand that you can set up 57 different workspaces, but there are some real downsides to that. You might want to set up one workspace and just break people into channels or user groups.

headshot of phil simon

“When I first started using it in the classroom, I simply said to them, ‘We’re not using email. I’m not going to respond anywhere else but through Slack.'”

Phil Simon
Author, Slack for Dummies

Don’t overdo it with apps at the beginning; you don’t want four polling apps and 78 channels from day one. Guide people into it. And I always encourage new people: “You got this.” If they’ve used Skype or any IM tool in the past, they can do this too.

You do want to be patient with folks, but you also want to encourage them to use it more because after all, Slack stands for the Searchable Log of All Conversation and Knowledge. If some people don’t use it, then the tool has less value as a corpus of information.

Slack: What advice do you have for email veterans who are just switching over to Slack?

PS: Rip the cord out. I keep emails for external use, like if someone wants to interview me or inquire about a speaking gig or something. But I want my regular communication with folks to be in Slack.

For email veterans I ask, how many irrelevant emails do you get every day? Instead of an email, what if you could send those messages to a channel and mute that channel, or change notifications, and you only checked that channel once a week instead of having to check an inbox all the time?

When I talk to folks about Slack, I tell them that there’s a little bit of a learning curve but it will save you time in the end because you can target your messages. You don’t have to go back and forth with someone on email.

Say you get an email that says, “Hi, I’m in your blah blah class. I have a question about the homework assignment,” versus a Slack message in a public channel, where you immediately know it’s from Hairol and you know it’s about the website development project. You have that context, so you reduce that cognitive load. You’re still going to get emails, but they’re going to be more relevant.

Simon says, “Try these apps for Slack”

In an excerpt from Simon’s book, he shares a few of his all-time favorite Slack apps: 

  1. Google Drive: Emailing attachments back and forth seems so 1999. The Google Drive app allows you to grant access to Google Sheets, Docs, and Slides directly in Slack. Once installed, you’ll receive notifications on new comments, files, and access requests on your Google Docs—and you never have to leave Slack. Emails about others’ comments go poof.
  2. Workast: Slack’s native reminders get the job done, but Workast can serve as a reminder app on steroids. With Kanban boards, custom tags, and templates, Workast is much more powerful than Slack’s native reminder functionality. You may decide that it’s worth paying for.
  3. Pocket: What if someone posts an interesting article, video, and/or podcast in Slack, and you would like to read it later? Pocket lets you save content to read or watch from your mobile device or computer, even if you’re offline (after you’ve synced it). I’ve used Pocket long before I started noodling with Slack and absolutely love it. It helps me stay informed without creating a bunch of bookmarks in my browser.
  4. Simple Poll: For quick one-question polls, Simple Poll is the way to go. This app also allows you to turn a message into a poll with one click. If you like, you can anonymize polls so that no one knows who voted for each option—including the member who created the poll.
  5. Donut: Whether you work remotely or in an office, you may not know many of your colleagues. Maybe you’re an introvert and value your solitude. If you want to meet your peers, though, Donut encourages employees to interact with each other in person or remotely.
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Slack has transformed business communication. It's the leading channel-based messaging platform, used by millions to align their teams, unify their systems, and drive their businesses forward. Only Slack offers a secure, enterprise-grade environment that can scale with the largest companies in the world. It is a new layer of the business technology stack where people can work together more effectively, connect all their other software tools and services, and find the information they need to do their best work. Slack is where work happens.