The Development Hell Death Spiral is one of the most frustrating, difficult-to-solve, and demoralizing experiences in SaaS—and nearly everyone who's built product has been there.
It goes something like this:
- The product needs a “big” change to support future work. Think: brand new frontend, big dependency update, major integration
- Since this change is so large and important, no other work is done at the same time (or perhaps can be done)
- And, because it’s so large and important, it’s harder than you expect. What was supposed to take 1 week turns into 2, then 4. The dev process is now single-threaded and jammed. You’re fully in Development Hell.
- Then, the Death Spiral starts: because of the gridlock, you're hesitant to talk to new customers—and even worse, you don’t know what to say to your existing ones.
Sound familiar?
If not, you’re either new to SaaS, have never made a big software change, or are just really, really good at computers.
For everyone else, let’s tease apart what's going on here. We’re going to disassemble the monolith that is the Development Hell Death Spiral so we can solve it incrementally and get unstuck.
“You done goofed”
Getting stuck in Development Hell is embarrassing.
A successful entrepreneur acquaintence once told me:
“It’s extraordinary how wrong—and how frequently wrong—we are, considering how long we’ve been doing this.”
Here’s my take: if you’re truly building something new, there's no way to predict exactly what your product will need to become in order to be successful.
At the intersection of
- “do important things,”
- “make huge progress,” and
- “move quickly”
is running full-speed into huge technical challenges.
It’s human nature to think you could’ve avoided Development Hell with just a little more planning, research, or foresight. There are a large number of people whose full time job is creating project plans with charts and graphs to avoid these “blockers.”
Here’s the truth:
There are no Gantt charts in rock and roll, baby.
If you’re in the situation where you need to make large changes to your product, that means you’re working with your customers and building around real problems experienced by real people.
Entering Development Hell is a rite of passage. It might even mean you’re on the right track. </cope>
An (abridged) tale
I’ve gone through Development Hell recently due to my fundamental misunderstanding of how people would use our product.
I’ll share the short story here, and include the full details (and specific, somewhat unrelated learnings.)
When we started Changebot we assumed that the product would be primarily a churn reduction tool, sharing changelog updates with existing customers.
We said: why not get credit for the work you’re already doing? Having gotten owned many times in the past by customers assuming we were DOA, this felt like a great idea.
The problem, of course, was our customers. The first (and only) feedback was “these updates suck.” We continued to get that feedback until, well, we made the updates not suck. Then the feedback exploded into a million different things and it became clear that people did not just want Changebot to generate updates for their current customers, they also wanted Changebot to engage and convert leads.
Quickly we learned that “changelog” is a word that nerds use, and normal people either don’t know what that means, or think it’s a word for nerds.
Our customers didn’t want a tool that passively sent content for our that they could share, they wanted a tool to create updates, remix them, distribute them — anything to get their message in front of their customers AND leads.
The bad news? Everything that we had built so far assumed that our frontend only needed to report on work that had already been done.
We attempted to build around it, but we realized we were actively avoiding building features because we knew there would eventually be a new frontend needed and couldn’t bear doing the work twice.
So then the front-end rebuild started. <thunderclap>
That was when I felt the Death Spiral creep up:
- I hesitated just a moment longer doing cold outbound.
- Social posts started getting shipped a bit more slowly.
- Trial signup outreach started to become more superficial and less specific.
- Existing customer check-ins started slowing.
All for the classic reason: if they needed a product improvement I didn’t know when we could deliver, so why get their hopes up?
I was standing on the edge of the cliff with the Death Spiral beckoning me to take a step further into its inky depths.
Here’s what I did instead.
Disassembling the Spiral
Development Hell is only the inciting incident, not the cause of the Death Spiral.
Development Hell turns into a Death Spiral when our fear of failure freezes the funnel. (DH becomes DS when FFFF.)
You stop cold outbound.
You slow down social posts.
You avoid trial follow-ups.
You pause check-ins with customers.
Because you’re worried the product isn’t ready. That it’ll disappoint. That someone will say “no,” or ask for something you can’t deliver on.
You start playing the conversations out in your head:
- You: Hello prospect, interested in some software?
- Them: Yes of course, but we need it exactly now and with the following modifications.
- You: Ah yes, of course, but could we perhaps show you what we have so far?
- Them: UNSUBSCRIBE. (Marked as spam. Reported to the SEC.)
Or…
- You: Hi Customer! Enjoying the product?
- Them: Yes, but I need one small thing.
- You: We can totally do that but it will take a bit…
- Them: CANCEL. (Chargeback issued. Lawsuit filed.)
Silly, right?
Well you’re the one doing it, Goofus.
This is all to make the point:
Radio silence is the actual cause of the death spiral.
When things get hard communication needs to go UP, not DOWN.
So, practically: what can we do? Like, specifically? How can we Escape the Loop of Doom?
Funny you should ask.
Introducing the HELD Method
How to Escape the Loop of Doom
You were HELD in Development Hell… now you're breaking free.
Hype
Build up your hype backlog.
Document (or create) a stockpile of all improvements, wins, points of interest, and anything worth sharing that’s not blocked by your current dev efforts. Think:
Non-product improvements: Think about what, outside the currently blocked product, has been or can be improved and shared with customers. Consider:
- 3rd Party Plugins like leveraging your existing API / webhook emissions to build a Zapier add on, or even more fun a TRMNL plugin.
- Process improvements like “better security” (which is usually just writing things down), faster support, or any other internal upgrade.
- Even taking the time to clean up your documentation can be worth talking about.
Work In Progress Updates: While we usually avoid sharing updates before a feature is done, if you’re going to be in Development Hell for a bit it’s worth sharing a quick update to explain what’s going on, why it’s taking time, and why it MATTERS.
You can also write a blog post about the process and publish it all over the internet… not that I know anything about that.
Retrospectives: Who says you can’t go back in time? This is getting published in the beginning of Q2… congrats, time for a Q1 recap!
While this might feel like the ultimate copout, I promise people love a recap. And, for the record, this might be most valuable for you and your team as a reminder that when you zoom out this current patch of Development Hell is just a temporary state.
Momentum Starters: Thought about starting a newsletter?
A podcast?
A book club?
Haven’t done that because you don’t have the time? Well, guess what, now you do! Starting a newsletter is the perfect reason to reach out to your customers and share all the cool content you’ll be getting to them, and it also creates a marketing asset that will exist and return dividends long after Development Hell has been conquered.
If you're blocked on shipping, shift focus to sharing.
Establish
Establish your comms plan.
With the above achievements in hand, pick where you want to engage with customers. There’s a huge number of choices which is why it’s important to plan with channels we want to engage on.
My suggestions are the usual suspects, but consider the following for your list:
- Social (ala X, LinkedIn, etc)
- In-app
- Forums (ala Reddit)
- Your marketing site
- Your blog
- Podcasts
- YouTube
You don’t (and shouldn't) pick all of these, but if you’re already active on social media it probably makes sense to add another channel, at least for the short term.
Light up
Double your output.
Whatever communication you’re doing on these channels historically, double it.
In the scenario 2 * 0 = 1, and scope your count to weekly—so if you’ve been doing one social post a month, get ready for 1 a week.
Again, we’re trying to force MORE communication and set a floor for how infrequently communication can happen.
Lean on the Hype backlog. Share work in progress, backstory, interviews, improvements, anything that’s potentially interesting, shows movement in the right direction, and definitively says “we’re alive.”
Go Direct
Finally, go direct.
Everything we’ve done above sets the stage for our piece de resistance.
Book calls with as many customers as you can. Get on chat. Find as many ways to interact with your customers as you can. A 15 min conversation with a customer does more lifting than 30 tweets a month.
As the ultimate hack—you don’t need to spend the whole time talking about yourself, the product, or whatever’s got you stuck in Development Hell.
Use this as a time to get new inputs. Ask how their business is going, what they’re working on, what they’re excited and or worried about. Ask how their cat is. Run some tattoo ideas by them.
By creating this framework of communication in steps 1-3 we’ve created a conversational environment to take advantage of. The secret silver lining is that since your hands are tied from talking too much about your product, now is the perfect time to step back, learn, and bring new info in.
In Closing
Getting into Development Hell is inevitable, but the Death Spiral is avoidable.
Remember that when product updates slow down, communication needs to go up.
Use the HELD method to get out of the Death Spiral, but here’s my final secret: don’t stop the communication cadence after you ship.
We can exit the Development Hell Death Spiral much stronger than we started, provided you catch the spiral early, put great systems in place, and stick to it.
