challenge_type in (‘rabbit’, ‘mustang’, ‘ocean’)

How to navigate instead of drown when your challenge is untameable

This one’s for the ocean boilers and the detail-oriented, the completionists and the over-achievers.

But it’s also for the cowboys and the wranglers, those who take pride in their ability to tame unruly projects and processes into well-documented and governed cross-functional alignment.

This is both a warning and a consolation.

Some challenges cannot be tamed. Attempts to do so will leave you exhausted and overwhelmed, with little to show for your efforts.

But that doesn’t mean you should give up on them. Too often, we walk away from a problem that can’t be tamed because we don’t realize that it can be navigated.

So hop on board, cowboy, and let’s talk about how to ride these waves.

Violence and Containability

Something can only be tamed if it’s containable¹. And how easy it is to tame or navigate has a lot to do with how (metaphorically) violent it is.

A containable problem is one that you can fully understand, that you can “wrap your head around”.

A violent problem is one that resists solutions because it’s dynamic, complex, rapidly evolving, etc.

Based on high/low containability/violence, we can sort our challenges into three categories: Rabbits, Mustangs, and Oceans².

Rabbits

Rabbits are easy to contain and not particularly violent.

Rabbit-like problems have finite scope and a clear path from problem to solution. You can wrap your head around them, and they don’t resist being solved.

Consider a minor software bug: once you understand the expected behavior of the software and the architecture of the program, you can apply logic deterministically to resolve the issue.

Little solvable problems like this are as ubiquitous and common as, well, rabbits³.

Mustangs

Wranglers love mustangs. Taming a mustang is a great story. And while mustangs are violent, they’re containable, meaning you can still form a pretty complete understanding of the problem space. They may have a feisty streak, requiring maintenance to stay in-line, but such maintenance is possible.

Consider an algorithm to detect fraudulent use of software. Once you ship a solution, bad actors adapt their behavior, resisting your solution. Even so, it’s still possible, with appropriate resources, to keep percent fraudulent usage within a tolerable level.

A lot of impressive B2C data solutions fit into this category: ride share routing, pricing optimization for travel bookings, distribution logistics, etc.

A key trait of the mustang is that the primary value is directly measurable. This is part of what makes these stories so compelling.

Impressive as they are, all those problems are ultimately easier than our next category…

Oceans

Oceans are both uncontainable and violent. They resist solutions and evade comprehension. Those who believe they’ve tamed the ocean are most likely to drown.

Often wicked problems, these challenges are entangled with emotional, moral, and cultural questions.

Any time our value prop is something like “wellness” or “success” or “alignment”, we’re operating in these waters. And this is particularly common in B2B SaaS⁴.

“Value based pricing” is inherently more amorphous than merchandise margins. Customer retention is meaningfully affected by the quality of human relationships, which are far harder to measure than clicks on a web page.

Consider a service like data visualization. It’s not an end in and of itself. Companies want to visualize data so that they can use data so that they can make decisions so that the company can be successful.

How does a company even know if it’s successful? How do we account for cases when high-quality decisions still have bad outcomes, and vice versa? How do we control for all of the other variables that affect decision quality beyond the visualization tool? What if it turns out the tool makes a lot of money from customers that don’t even get that much legitimate use out of it, just because they like the tool and having it makes them feel good?⁵ We don’t want more customers like that, right? Or do we?

We might let existing customers vote on what features we should work on next, but what do we do when growing the company requires attracting prospects that have different priorities than our current customers?

The primary value of data visualization cannot be directly measured.

And the same is true of data warehousing, marketing automation, financial record keeping, and so many other B2B SaaS products.

These spaces are untameable. But they can be navigated.

A Navigator’s Mindset

A tamer first asks: “What am I dealing with?”

A navigator first asks: “Where do we want to go?”

Let’s apply this to NPS⁶:

• Tamer: What are the drivers of our current NPS?

• Navigator: What are realistic steps we could take to improve customer experience? What features might help us choose between them?

If NPS for this organization is a tameable problem, the cowboy’s approach to understand the full problem space is going to pay off. They may come up with novel ways to improve NPS. And even if drivers aren’t things the company can directly impact, the team can at least identify leading indicators.

But what if NPS for this org isn’t tameable? What if there’s a lot of noise, and the key drivers vary significantly region to region or day to day? Attempting to understand all drivers to NPS is like trying to bottle the ocean.

Here, the navigator pulls ahead. With an unshakeable focus on “where are we going?” the navigator doesn’t have to understand every current in the ocean—only the ones that will get the team from point A to point B. The navigator starts moving early—spinning up an experiment to see if if an onboarding tutorial improves satisfaction—and comfortably changes course if that approach doesn’t move the needle.

Navigators prioritize direction over certainty and think in terms of knowing enough, not knowing it all.

Talented navigators are masters at tolerating uncertainty. Though experienced navigators will have expectations for the direction and force of certain wind and water currents, they’ll always defer to what they see in front of them. An unexpected land mass could be missing from the map, or an indicator that the boat isn’t at all where they think it is—they’ll keep collecting information and acting on the most probable truth.

Navigators think in three dimensions. They’ll keep the end destination in mind, while making effective decisions about whether to push through a storm or change direction in the short term to navigate around it.

Let’s return to our customer NPS example. A product manager pitches an idea to use natural language processing and machine learning to analyze all written responses to the NPS survey to figure out what customers are saying. But there’s not yet any machine learning infrastructure in place—so a storm is ahead.

A cowboy, eager to tame their mustang, jumps into the deep end and isn’t able to demonstrate value before the business’s attention moves on to the Next Big Thing, leaving the efforts unused and the cowboy demoralized.

Whereas an apt navigator surveys the waves and asks a key question: “Where are we going?” With the bigger picture in mind, the navigator is able to help the product manager spot a tail wind and sweep around the storm: simply showing how often the words “bug” or “doesn’t work” appear in negative NPS responses gives the team the sense of progress that they were looking for.

When you’re effectively dealing with a mustang, it will feel like you’re wrapping your head around the problem.

When you’re navigating an ocean, it will feel like you’re finding a path through the problem.

The AEndian Ocean

One area that’s particularly tempting to treat as a mustang is career progression.

And (nearly) every talk, article, or book about tech careers wants you to believe that this is a tameable problem. That it’s possible to understand, codeify, wrangle, contain the concept that is a career in analytics⁷.

But this, like “success” or “wellness” or “alignment”, is also untameable.

A career isn’t quite something you wrap your head around, as it is something you navigate through.⁸

We can still certainly learn a lot from each other, but I think it’s important to remember that the same tactics, in different environments, can yield opposite results. After all, the sun leans to the South in Boston—and to the North in Australia.

So while we can share local weather patterns with each other (like shifts in our respective industries) and discuss the merits of various north stars (like prioritizing happiness, or title progression, or early retirement) and learn concrete skills to keep our boats afloat (like warning each other about hidden biases)—beware anyone who claims to have tamed the ocean.

And ignore anyone who tells you that you have to know everything before you set sail⁹. Skills will serve you far longer than facts.

You don’t need to know where all the storms are, if you can spot them on the horizon.

You don’t need a map if you have a sextant, the stars, and a lookout.

It’s more about responding and adapting than controlling or predicting.

So for you cowboys: try to figure out whether you have a mustang or an ocean before you drown.

And for you ocean boilers: don’t let cocksure cowboys keep you from pushing your boat into the waves. Some challenges are impossible to wrap your head all the way around. Just ask:

Where are we going?

And what’s the next small step that will get us there?

1. Think: paddocks, saddles, bridles. Even if you tempt a feral cat to your back door, you’ve still captured their attention.

2. You’ll notice that we’re missing the ‘low violence’/‘uncontainable’ quadrant of this 2x2. While the expanse of space fits this metaphor nicely (since it’s uncontainable but significantly less violent than the ocean), I couldn’t think of many real-world problem types that sort into this category. Once something is relatively static and predictable (like space travel), it can be sub-divided effectively into lots of smaller tameable problems. Landing on the moon, for example, is a tameable problem. The ocean, being much more dynamic, dense, and violent than outer space, defies this kind of tidy sub-division.

3. They also tend to multiply if you let them linger 👀

4. Business to business software as a service

5. Or because the account team is so nice and helpful that customers feel a bit bad churning.

6. Net Promoter Score, a common customer metric that gauges how likely they are to recommend the product to others.

7. And within that, what’s even a “career” in general. And within that, the abstract concepts of currency by which we (not always successfully) transmute hitting a lightning-filled rock into acquiring food from one shelter and carrying it to another shelter that we are reasonably confident we will not be forcibly evicted from.

8. The same is true of all of our most pressing societal challenges. These are wicked problems, and expecting that it’s even possible to have a complete set of answers is already a flawed premise. The more we’re focused on navigating through what’s around us, instead of trying to have a tidy understanding of the whole thing, the more likely we are to actually be able to take advantage of the opportunities in front of us.

9. Even/especially when that person is yourself.