Dear Instructure: Please Don't Become the Next Blackboard

I was classically trained on the five-paragraph essay and took my fair share of AP classes, so "compare and contrast" is like a reflex for me. When I read Michael Feldstein's article on Canvas taking Blackboard's spot on the LMS totem pole, it got my gears spinning. If Instructure is finally taking top shelf, what are we going to do to not become exactly what we set out to fix in the first place?

Instructure is working on new leadership in marketing, sales, product, operations -- oh, and we've also got a new President. Maybe a little history lesson isn't such a bad idea (here's quick refresher of how we got started). My goal here is to say, "hey, here's a list of things we should all keep an eye on so we don't go all you-didn't-learn-anything-President-Coin-from-Hunger-Games." Back in the day I used to take some time in every onboarding helping new hires to catch the vision of why we were different and to understand the Instructure Way. So if you like you can consider this your old-school onboarding indoctrination session.

(It's probably worth noting that I can't help but say "we" even though I'm not at all involved in Instructure anymore, other than the occasional lunch with my old coworkers. It's hard to let go, I guess. see: footnote)

1. Focus on the User, not the Dollar (It's Okay, the Dollar Will Still Show Up)

We showed up on the edtech scene in 2008, and people were more than happy to not just give us the time of day, but to unload their frustrations with Blackboard -- and ideas for new hotness they were afraid they'd never see. Blackboard was really stinking it up from what we could tell. We crashed their user's conference in Vegas after a few years and told everybody we were the anti-Blackboard. We didn't need a better value prop than that. Just "not Blackboard" and a bunch of t-shirts was enough to get people excited.

Mind you, we had a lot more than that going for us. Blackboard and D2L have continually had a hard time figuring out what makes us better. That's probably partly because *we* had a hard time explaining what made us better. All the "easy to use", "end-user-oriented" claims felt like hackneyed platitudes. The truth is what we built was a fresh take on the LMS, starting with students and teachers and grand instructional design ideas instead of with administration and management. Devlin Daley and I were fresh out of college, we felt the pain on the student side and as TAs, and we picked the brains of every teacher we could find.

What was so different about Instructure is that we said "teaching and learning is hard enough without technology getting in the way" and we meant it. There were a hundred little fibbly bits that we coded into the product, not because they were on the top of someone's feature list or because they'd close a deal, but because they were the right thing to do. We gave teachers permission to make their own content public, we gave students ownership over any files they uploaded, we made sure that there was a rational way to get to any piece of course content, we let people set their own email addresses, etc. etc. Sometimes this caused problems because we still had customers pushing from the management side, but almost always we fenagled a workaround that didn't compromise on "making teaching and learning easier". And even though nobody calls out those little finishes in their "why we chose Instructure" blog posts, they are a major part of our "different" approach, and they help close deals.

So yeah, that's gotcha number one. Are we still the student/teacher advocate? Nobody pays us to do that, and plenty of decision-makers push us to give it up, but we've got this in our DNA and we can keep it up. The edubloggers that would function as our checks and balances have mostly written off the LMS entirely, so that leaves it on us. Keep an eye on it or you'll find people getting less excited about our products, but without a clear reason why.

2. Keep Solving Interesting Problems

Blackboard's user conferences had a reputation when we showed up. They threw a great party, everyone said so. But people also said that they made a lot of noise to hide the fact that nothing interesting was actually going on with the product. Merging Blackboard and WebCT into a single company could not have been fun or easy, so they had a valid excuse, but at the end of the day interesting things just weren't happening.

Instructure is also known for throwing a great party. InstructureCon has always been a blast, with great swag, surprise performances, and a fun theme (I better see some Greatest Showman references this year or I'll be sorely disappointed). But it's also been a place to grow a strong community and to introduce people to the latest and greatest in Canvas.

Innovation isn't easy, and it doesn't come just at an annual user's conference. You can't just suddenly show up and say, "look! Innovation!" which plenty of people got at Instructure. Devlin and I made a great combo getting this stone rolling because we weren't straight execution (despite my misplaced best efforts) and we weren't just grand ideas, we had room for both, and it was awesome to see that keep going. You have to be deliberate about allowing new ideas to develop or you'll end up too demand-driven. Nobody asked for SpeedGrader, or a fully-public API, or an LTI app ecosystem. We have a great head-start with our strategy of openness, but watching some other companies, I'm surprised with how quickly "open" can die on the vine if you don't keep on it.

3. Don't Rob the Cash Cow to Pay the Pied Piper (And Don't Mix Metaphors)

When we talked to schools about their beefs with Blackboard, people kept saying Blackboard was focusing on too many things. Multiple times we heard "I mean, they're even running on-campus payment systems and swipe cards! It's no wonder they're not doing anything new with their LMS." Me, I'm more pragmatic. I get that you need multiple revenue sources, especially if you want to grow. Sometimes they don't make much sense to outsiders.

Instructure has had the Canvas product for a lot of years. After a bit we tweaked it for K-12. Then we did some work to get it ready for international. Then we introduced Bridge and Arc. Then we bought Practice and added Gauge. Then we started expanding our HCM suite. That's a lot of pots to stir, so you have to pay close attention if you want to do it right.

Investors ask a lot about the breakdown of our R&D and marketing investments. Are we putting everything into Bridge and ignoring Canvas? Are we giving international the attention it needs? Can we add a new product without jeopardizing our existing product quality? There are plenty of easy, reassuring bizspeak hush puppies, but the questions themselves are worth thinking hard about.

Are we solving interesting problems in all the markets we're going after? If we're not doing anything interesting then what are we doing? We have some great products, and I'm confident we don't need to start milking any of them as a legacy product just to siphon cash off into our next growth target. Maybe that would be a good use of funds, but it's frankly not enough, none of our products are *that* legacy. If we're going to add new products to our repertoire, then let's definitely make them awesome, we've got the ability to keep doing that. If we don't have the bandwidth to keep making all the things awesomer, then we have too many things going on, investor pressures be darned. But hey, the good news is that we have enough employees that people should be able to be innovating just about everywhere.

The red flag for me will be if we don't see innovations being discussed at InstructureCon. It's a bit of a coal-mine-canary for continued investment in our existing customer base. We can sell complementary products for more walletshare, and we can expand into new markets, but we have to be really careful. We don't want to move all the Risk pieces over to Asia and leave Europe covered in little onesies.

This one is particularly tricky, because it'd be easy to justify by saying "we're still investing heavily in Canvas", when really most of that "investment" was just ongoing support and maintenance. I'm more interested in the breakdown of the innovation budget, and, like I said, the best external proxy I can think of is InstructureCon announcements. There's a lot of interesting work we've been a part of, so keep an eye on what makes it to the surface. We've had some great years and some meh years as far as innovation goes. Don't let the conference get all hollow and stuff, and don't pretend to be excited about "innovative" iterative enhancements. People will notice. Customers know when they're being pandered to, and lipservice is transparent and boring. Keep the awesome going, instead.

4. Make Sure People Still Like Hanging Out With Us

This is getting long and a bit rambling, but stay with me. I'll put a cute unicorn at the end. The biggest gotcha, and the one I really don't have any visibility into anymore, is company culture. From the outside, Blackboard of 2008 felt stuffy and overbearing. The D2L lawsuit didn't exactly help that image. People didn't like talking to tech support, they felt like they were getting nickel and dimed on upsells, and nobody would have called them "cool". That's in spite of the pockets of earnestness we early Canvasites saw when we made a surprise visit to Blackboard's new corporate offices. There were people at the company trying to do the right things for the right reasons, but it just wasn't breaking to the surface.

Let's not get to that point, eh? We built an awesome company that didn't take itself too seriously, where everyone was genuine and genuinely trying to make things better. Everyone knew we needed to get to the root issue before crafting a solution, and that every touch point with our customers needed to be an impactful one. We weren't a company that hired young single dudes to squeeze extra work out of them with catered dinners and ultimate frisbee. But we also weren't a company where people took three-hour lunches and tried to beat the commute home. We worked hard because we felt we were doing something important. We had an open floor plan because private office jockeying is a joke. We made our panda pinata be the office receptionist by hooking it up to a speaker with text-to-speech. We came up with goofy meeting room names because it was fun to watch people in expensive suits file into a room called Battletoads. We didn't take all that stuff seriously because we we were too busy trying to make a difference where it mattered.

Obviously you have to grow up along the way (that panda receptionist could be rude), but we never have to lose the passion that draws people to work for Instructure because, hey, it seems like an awesome place where people are doing awesome things. When the new hires I've talked to have still felt that vibe, it made me happy, let's not lose that. We didn't always get everything right (ask Ryan Shaw how many times he had to re-merge master into the SpeedGrader branch before it was ready, or Sunny Washington about inter-departmental lunch invitations), but we did get a lot right. We were extremely lucky with our timing, I'll be the first to tell anybody. But it would be a gross oversimplification to assume that the only reason we're doing a "Canvas:Blackboard" exercise thing right now is because we showed up with cloud-plus-modern-web right at Blackboard's weak point. Who we are bleeds into everything we do.

Keep Doing Awesome

I haven't kept the best count of how many early employees are still at Instructure, it's been ten years and people move on. I like to believe that the culture transfer has been happening seamlessly all along. We've changed offices six times, we've shuffled through plenty of execs, but I hope Instructure is still the awesome place to work that it used to be. I'm actually very confident that with the right energy we can keep doing awesome things all over the place, just like we have in the past. I hope people are emotionally invested and trying to make a difference for education. I hope that people on the ground working their heels off to do the "right" thing in spite of the all inevitable corporate pressures to not bother, can be proud of the end result. If that remains true, then I'd say we've earned our place at the top of the list.


You made it! Here's your reward:

Ooh, bonus gotcha for the road. Blackboard Ultra is still not really a thing. I'm sure there are plenty of internal Instructure jokes about it. But turning a ship that large is hard, and with private equity on your back and ongoing reorgs I get why it's taking so long. It may be asking too much to try to get Canvas through the next technology wave (blockchain-based LMS, anyone?), but please let's don't promise a product years before it's ready. Personally, I don't think you need to promise new features unless they're imminent, just release the things when they're ready to run amok, but that's more an opinion. This market isn't heated enough that you need to get the jump on anybody, just do awesome stuff and share it when it's ready, I say.



Footnote: Somebody somewhere is probably going to call me overly simplistic or naive. That's fair, ex-founders and their rose-colored glasses is probably a meme somewhere. I've seen Instructure change and evolve a lot, and hopefully people will agree that I took the changes in stride, I didn't keep pining for the good old days every time we moved up a rung on the corporatiness ladder, progress means you lose a bit but you gain more. But maybe I'm all negatively nostalgic, I'm obviously not the best judge. I doubt there's a shortage of castaway founders shaking their heads over the grand insights nobody is asking them for anymore. Whatever, this is getting too introspective to actually be productive. Let's focus, here.