New in Basecamp 3: Image Galleries

At Basecamp, we write a lot—from announcements to pitches, and everything in between.

Quite often, we’re presenting something that has a Before and After, like a mockup or interface design that’s been revised. Until now, this was always kind of frustrating. Basecamp only supported full-width images, so it could be difficult to quickly compare two images at once.

Today we’ve added support for side-by-side image galleries inside written posts!

This is a subtle but substantial change: galleries support and enhance your writing by making it more fluid, expressive, and precise. They’re great for sharing screenshots, comparisons, mockups, sketches, photos, and so on.

Here’s how it works.

Creating a Gallery

In any rich text field in Basecamp 3, you can make a gallery of images by uploading multiple images at the same time. You can do that in the file-browser dialog, or by dragging and dropping files into Basecamp directly.

Dragging images to make a gallery

When you do that, Basecamp will automatically group the images together in a nice arrangement. There are a few different layouts based on the number of images you’ve posted together.

If you upload two images at once, they’ll be oriented side by side.

If you upload three images at once, they’ll be shown 3-up in a row.

If you upload four images at once, you get a 2×2 grid.

And then finally, if you upload 5 or more images, they’ll be arranged in 3-up-sized rows.

You can also make a gallery by uploading images one by one. Just upload one image, then immediately upload another. Basecamp will notice that the images are directly adjacent and bundle them for you.

Adjusting a Gallery

If you don’t want the gallery layout, you can split it up by putting your cursor between images and hitting return. That will break up the gallery at that spot and resize things accordingly.

If you prefer a different arrangement (for example, maybe the second image should be first) you can drag and drop them to reorder.

You can also drag and drop images outside of galleries into galleries, and vice-versa.

It all works like you’d expect images in a text editor to work!

Related Changes

New toolbar for images

Clicking on attachments in Basecamp’s text editor has changed a bit. You’ll now see a balloon at the top that shows the file name, size, and the trash button. (Formerly this was just a trash button.)

New attachment toolbar

A more prominent caption field

Did you know you can write custom captions for any image you upload in Basecamp? If you didn’t, you’re not alone! This feature used to be rather hidden, but we coaxed it out of its hiding place.

Now just click on any image in the editor and you’ll see the Add a caption… field at the bottom. Click on that to type any caption you like.

This is a caption for the picture that shows adding a caption. 🌀

Popup menus on gallery images

Every image in a gallery has a small ••• menu adjacent to the caption. Click that and you’ll see a popup with the original file name and file size, plus links to download the image, or view it at full size.

Popup menu for details

That’s it!

Galleries work everywhere right now, in our mobile apps and on the desktop. We hope this update helps you create richer posts, and makes writing in Basecamp a little more enjoyable. Let us know how you like it!

New to Basecamp? Head on over to basecamp.com and see what it’s all about.


New in Basecamp 3: Image Galleries was originally published in Signal v. Noise on Medium, where people are continuing the conversation by highlighting and responding to this story.

Managers: You’re not prepared for your one-on-one meetings. Here’s what to do.

Four steps to take when you’ve got a one-on-one meeting coming up.

You’re not prepared.

Or at least that’s what employees think when it comes to one-on-one meetings. In a recent survey we conducted of 125 managers and 45 employees, we found 35% of employees believe their manager is only “somewhat prepared” — and 15% of employees think their manager is “not prepared” or “not prepared at all.”

That’s almost half of employees thinking that their managers aren’t as prepared for one-on-one meetings as they could be.

Managers seem to agree. Sixteen percent of managers we surveyed said their biggest frustration with one-on-one meetings is they’re never sure how to prepare or what to ask.

Fortunately, preparing for a one-on-one meeting is neither hard nor time-consuming. Before your next one-on-one, here are the four things you can do (and each takes ten minutes or less):

#1: Get up-to-speed.

You waste time when you’re not up-to-speed. When you walk into a one-on-one meeting not knowing what the person has been working on for the past month, you squander 10 -15 minutes to get caught up on old information. That’s 10 -15 minutes that could’ve been spent discovering and discussing new information. Instead, spend a few minutes getting up to speed before the meeting rather than during it. Specifically:

  • Review status updates ahead of time. You’ll save time by not rehashing “What’s the latest on X?” And you’ll better orient yourself on what the focus of the one-on-one meeting should be.
  • Revisit notes from the last one-on-one meeting. You’ll realize there’s an important topic you need to circle back on, or an action item you need to complete. These notes can also help inform the questions you want to ask for this upcoming meeting.

#2: Ask your direct report to create an agenda.

Ask the employee to create an agenda ahead of time with what might be on her mind. You can say or write something like: “Mind kicking-off the first draft of the agenda for our one-on-one meeting? I want to focus on what you want to talk about, first. And then I’m happy to take a pass and add anything else to it.”

By letting her take the lead and initiate the agenda, you demonstrate to her that it’s her priorities that you want to address first. She’s in the driver’s seat, not you.

Then, of course, you’ll want to review the agenda before the meeting, and offer any additions for what you want to talk about.

#3: Clearly define for yourself: What do you want to know?

Yes, you’re asking the employee to write the agenda — but you also want to think for yourself what you want to know. Is there a concern you have about this person’s ability to work well with others? Are you wondering if they feel challenged enough by the work itself? If nothing specific comes to mind, consider these four areas of focus for a one-on-one meeting:

  • Concerns and issues. What potential problems might be bubbling up that you don’t know about, but should?
  • Feedback about work performance. What does your direct report need to be doing differently? How can you improve your own management style?
  • Career direction. How can you help support this person progress toward their career goals? Are you both on the same page for what progress looks like?
  • Personal connection. What outside of work in their life is going on that you want to know more about?

Reflect on these four areas to generate ideas for questions you should be asking, or topics you think should be covered during the one-on-one meeting.

I’d recommend picking one or two of these focus areas, and then brainstorming at least 3 -7 questions for each area. You may not ask all the questions (or any!), but they are helpful to have in your back pocket should the conversation lag or veer off-topic.

To help you get started, here are some examples for one-on-one meeting questions in each focus area:

Questions that uncover concerns / issues…

  • “When have you felt most motivated about the work you’ve been doing?”
  • “When have you felt bored in the past quarter?”
  • “Is anything holding you back from doing the best work you can do right now?”
  • “Is there any red tape you’d like to cut at the company?”

Questions that elicit feedback about work performance…

  • “Would you like more or less feedback on your work? Why/why not?”
  • “Would you like more or less direction from me? Why/why not?”
  • “What aspect of your job you would like more help or coaching?”
  • “What’s a recent situation you wish you handled differently? What would you change?”

Questions that help provide career direction…

  • “What have you been wanting to learn more of, get better at, and improve on?”
  • “What’s one thing we could do today to help you with your long term goals?”
  • “Is there an area outside your current role where you feel you could be contributing?”
  • “If you could design your ideal role in a company, what would it look like?”

Questions that foster a sense of personal connection…

  • “How’s life?”
  • “What have you been reading lately?”
  • “Been anywhere recently for the first time?”
  • “What have you been excited about lately?”

I always try to ask at least one question focused on personal connection, and use that question to open up the meeting. This helps break the ice at the beginning of your meeting, and builds rapport with your employee. Without this sense of rapport, your employee won’t feel comfortable divulging anything meaningful — nor will she find the conversation much fun.

For more ideas for questions to ask during a one-on-one meeting, you can visit here.

#4: Calibrate your mindset.

Take a minute to remind yourself: This meeting is not like other meetings. You aren’t running it. Your primary job is to absorb the information being shared with you, poke holes to figure out how an employee is actually feeling, let things marinate, and then figure out when you need to do. You shouldn’t be talking. You should be listening and scanning for the truth.

These four steps takes 15 minutes, maybe 30 minutes at most, to complete in total. That’s 15 minutes — 30 minutes of preparation that ensures your hour-long one-on-one meeting is not an hour wasted. Invest in preparing for your one-on-one to get the most out of this time together.

Enjoy this piece? You might enjoy the guides I wrote on one-on-ones too. You can get our Guides to One-on-One Meetings here…

P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @clairejlew.)


Managers: You’re not prepared for your one-on-one meetings. Here’s what to do. was originally published in Signal v. Noise on Medium, where people are continuing the conversation by highlighting and responding to this story.

Take a Break

Smell ya later! We here at the Rework podcast are taking off the month of August. Before we left, we interviewed three business owners about sabbaticals. In this episode: Adeline Koh of Sabbatical Beauty shares the story of how she ended up starting a business while on leave from a different job; Jason Fried explains why Basecamp offers paid sabbaticals as an employee benefit; and Rachel Winard of Soapwalla talks about what it’s like to go on sabbatical when you’re the boss.

We’ll be back in September with all-new episodes of Rework! In the meantime, you can catch up on episodes you missed at rework.fm or peruse the archives of our previous podcast, The Distance.


Take a Break was originally published in Signal v. Noise on Medium, where people are continuing the conversation by highlighting and responding to this story.