The Cone of Uncertainty

Erratum: an earlier version of this post made it sound as though this concept was my idea. My friend Christina Wodtke rightly called me out on it; the cone of uncertainty is a concept with a long history in project planning. I must have read about it at some point and buried it in my subconscious. Apologies for any confusion this may have caused; I’ve edited the post to clear it up.

“The beginning is always today.”
— Mary Wollstonecraft

Imagine you’re ramping up to work on a new project that will keep you and your team busy for many months. Before you start, you must define a plan for how you will tackle the work. For example, you must figure out what resources you will need and by when. This requires that you make predictions about the future state of the project: “By the fourth week, we should have already produced high-level design directions. At that point, we’ll be ready to engage a UI designer and a prototyper.”

The problem is that you can’t predict the future with certainty; the best you can do is make educated guesses based on previous experience and best-practices. And of course, reality has a way of messing with things: By week three, the team may uncover a vital requirement they initially missed that forces them to re-think their direction.

Because of this, the team’s confidence in their plans should drop the farther they cast into the future. They must be sure of the activities they need to undertake immediately, and doubtful of the things needed in the more distant future. I often visualize this as a circle of uncertainty around the team:

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How To Grow a Digital Business Without Sacrificing Its Soul

Photo by Benreis CC BY 3.0 via [Wikimedia](https://commons.wikimedia.org/wiki/File:Bagel_lox_sesame_seeds_St._Lawrence_Market.JPG)
Photo by Benreis CC BY 3.0 via Wikimedia

Many years ago, my wife and I heard about a new bagel shop that was opening near our apartment. We decided to check it out one Sunday morning. The place was charming: roomy enough to feel comfortable, but not bustling. There was a large selection of fresh bagels, an assortment of fixings (including many flavors of cream cheese), and a well-stocked self-serve coffee bar. We loved it; lounging there over the newspaper became part of our Sunday morning routine.

It wasn’t long before other people discovered the bagel shop. Soon the place was crowded, and the experience suffered. Ordering became a chore, with lines that stretched out of the store. The once quiet place became packed and noisy. Worst of all, open tables became a rarity. We changed our routine to arrive close to opening time to get one​, but then we would feel guilty about lounging around when others were waiting to sit.

Eventually, the owner leased the store next door and the bagel shop grew to three times its previous size. The expansion relieved some of the shop’s most pressing issues; now it was easier to find a place to sit. However, the quality of the food suffered and the relaxed experience of the early days was gone. The new shop was OK — but it wasn’t the same. At three times its former size, it couldn’t be. That’s not to say it wasn’t a good business anymore; it probably made more money in its new digs. But the soul was gone.

Change is a central part of doing business. If things aren’t going well, you must do something about it. But when things are going well, you must also do something about it. Staying still is the only option not on the table. How the business responds to the always-changing context it participates in (and helps create) will be one of the factors that define its level of success.

Architecture is a critical factor in that response. The bagel shop responded to increased demand with an architectural intervention that changed the character of the business. Even though on the surface things looked the same, a threefold increase in the shop’s physical environment made for an entirely different experience.

The laws of physics don’t apply to digital businesses in the same way they do to a bagel shop. A digital business can scale without needing to physically grow. However, the architecture of its information environments plays a critical role in how customers perceive and interact with the business. As with the physical business, the architecture of a digital business must change if it’s to evolve.

A digital business looking to level up has many options open to it. For example, a product could be on track to become a family of products or a platform. Or perhaps the business is expanding from an advertising-supported business model to a paid-membership model. “More of the same” is not on offer in such cases. The business must rethink its information architecture. Yes, this will impact its website and app navigation structures. But more than that, it’ll result in a new conceptual model that will affect all aspects of the experience.

A thoughtfully designed architecture will result in a new UX that will enable the business towards the next stage of its evolution, without compromising the things that made it great. A solid information architecture is a platform for enabling directed emergence: aimed towards a fixed objective, but open-ended enough to respond to real-world conditions as they arise; a platform for sustained growth that doesn’t sacrifice the soul of the business.

Giving Feedback

“Can I give you some feedback?” You hear the words, and immediately get a sinking feeling in your belly. “Uh oh,” you think. “What did I do wrong?…” For many of us, the word feedback has negative connotations. It’s become a polite euphemism for criticism; something we offer up only when our expectations aren’t being met. But feedback is not inherently negative.

Feedback refers to the means by which a system can alter its behavior. (The outputs of the system “feed back” into it as inputs, which the system then acts on.) Considered it in this light, feedback can be seen as a steering mechanism: a way of keeping things within bounds. Too much of a good thing can be as bad as too little; knowing where you are relative to the bounds you’ve set allows you to correct course. If you step on the gas, yoiu see the needle on the car’s speedometer creeping up. Past a certain point, you know you’re exceeding the speed limit, so you take our foot off the gas. The speedometer is one of the car’s mechanisms for giving you feedback.

Feedback applies to relationships as well as other systems (such as cars). If you’re managing someone who is performing below the expectations that are expected of him or her, part of your job is to act as the speedometer; you must let them know. (Hence, the sinking feeling.) But the speedometer doesn’t only tell you when you’re going too fast; it also lets you know how fast you’re going in general. Sometimes going too slow is not good either. Giving (and receiving) clear, frequent feedback is essential; it allows team members to assess how they’re doing and whether or not they’re on the right track.

What I Look for in Collaborators

Recently a student asked me what I look for when hiring people. I sent an abbreviated response but thought it worthwhile to expand on it here since it may be useful to others.

When I’m evaluating somebody as a collaborator, I want to know about four factors:

Is s/he a solid thinker?
This comes across in how they express themselves in interviews and written communications, and what they express. Do they demonstrate a solid grasp of key concepts and relationships between them? Can they explain difficult concepts without resorting to jargon/cliches? Can they explain their decision-making process clearly? Are they confident in what they’re saying?

Is s/he a solid maker?
This comes across in the artifacts in their portfolio. Do artifacts communicate clearly? Do they get to the point? Do they demonstrate mastery of medium? Do they demonstrate mastery of craft? Do they demonstrate clear intent? Do they demonstrate a willingness to experiment/push boundaries?

Is s/he a team player?
This is difficult to evaluate through portfolios and interviews; references come in handy. Still, there are cues that reveal how they relate to others. For example, do they give credit to their teammates or do they claim all the glory for themselves?

The character factor
Most importantly, I want to know about their character. Are they upstanding? Do they behave courteously towards others? Do they demonstrate a clear value framework? This is rather difficult to evaluate over brief interactions. Again, references help.

I place less weight on other things such as formal education or a record of having worked at the “right” places. The four factors above go a long way towards identifying​ the people who will help us be successful.

How Do You Know It’s Good?

We do not describe the world we see, we see the world we can describe.

— René Descartes

Let’s say you’re working on a project. The project launches, other people start using it. How do you know it’s good? 

This is an important question, but trickier than it appears at first. I divide it into three parts:

  • Someone is being cast as the arbiter. (“You.”)
  • A continuum is implied: from no-good to good.
  • An objective is specified: you want the thing to lean towards the “good” end of the continuum.

All three are up for examination. Let’s start with the arbiter of “good.” If the project is being developed within an organization, it’s likely that many parties will have stakes in its success. And even if you’re working alone, there will still be other parties involved. For example, there will be people interacting with your system. They, too, will have a say on whether it is good or not. “Good” will likely mean different things to different people.

There’s a point along the continuum at which the thing is obviously no-good; it’s not meeting anyone’s criteria of success. As it evolves and (ostensibly) improves, it moves closer to meeting more criteria. (In theory, this process ends with a “perfect” artifact. In practice, this is an impossibility; the context around the system continues to evolve as the project progresses, changing the criteria for success for at least some participants.) Eventually, the system moves far enough along this continuum to flip over into the “good” side. (We say it’s “good enough.”) In other words, it meets the success criteria of a large enough group of stakeholders.

Who defines the threshold where the artifact flips from no-good to good enough? How is this measured? This is the crux of the matter: What “good” means in a particular context is up for grabs. Often there will be one lead stakeholder who will be calling the shots. There is an expectation that this person (or team) will be the arbiter of “good”. But these stakeholders are often buffeted by political forces that influence their decisions one way or another.

Designers working on complex systems need to understand how success will be measured. The criteria stakeholders will use to evaluate success will have an important influence on the structure and form of the system. For example, if the organization defines success and an improvement of a Net Promoter Score (NPS), the system’s designers will be strongly incentivized to structure it in such a way that feeds that measure. (As Jared Spool has pointed out, this may not be a good idea in the case of NPS.) Stakeholders and clients using NPS as a filter will see the world through that lens. This can leave out important factors for success.

What’s good for an internal team may not be good for an organization as a whole. And — more importantly — what’s good for the organization may not be good for society as a whole. As designers of complex systems, we’re called to see beyond the world we (and our stakeholders) can describe and measure. Our vision needs to encompass a wider (and longer-term) perspective if we are to provide real, enduring value.

Aligning Incentives

Incentive structures work. So you have to be very careful of what you incent people to do, because various incentive structures create all sorts of consequences that you can’t anticipate.

— Steve Jobs

What incentives drive your actions?

I don’t mean this in an aspirational, high-level, mission-statement sense. I mean: How is the value you add to the ​world remunerated? How do you put bread on the table? If you’re rewarded for a particular set of behaviors, you will most likely engage in those behaviors.

Some consultants charge by the hour. They get paid more the longer they focus on a problem. But the client doesn’t want the project to take longer (or cost more) than it needs to. In fact, the client wants a good job done as fast as possible. He or she is driven by different incentives than the consultant; time is usually a key factor. This is a case in which incentives are misaligned.

If you look around, you’ll find many such misaligned incentives. For example, as a citizen, ​you want to be well-informed so you can make better decisions. However, many mass news media are driven by engagement — how long they can keep you around so you can watch more advertisements. Engagement is a very different metric than elucidation; people will write and say outlandish things if they think it’ll make you pay more attention. (And if they get paid more when you do.)

We’ve never before been able to learn so much about what drives people, and instantaneously re-define their contexts based on what we learn about them. Incentive structures become reified in information environments. So when designing an information environment, we should work towards aligning the incentives that drive the environment with the incentives and goals of the people who will use it.

Design as a Way of Knowing

“The act of envisioning possibilities and elaborating them is itself a pleasurable and valuable experience. Just as realized plans may be a source of new experiences, so new prospects are opened up at each step in the process of design. Designing is a kind of mental window shopping. Purchases do not have to be made to get pleasure from it.”

— Herbert Simon

After years of kvetching, designers finally have a “seat at the table.” Large organizations increasingly acknowledge the importance of good design, and many have developed internal design capabilities. But many also misunderstand what design is good for.

Design is not just for creating more engaging experiences, or seamless interactions, or driving conversions, or reducing call center volume. The point of design is to envision and test possibilities in a tangible way. What would the world be like if this product/service/system existed? How would our customers react to it? What would it do to the rest of our product line? How does it fare compared to competitors? What do people call something like this? How do they interact with it? What effect does it have on our systems?

We can argue about these things and build mathematical models to compute the odds of success. But there are limits to the things we can know about the future using only words and numbers. Design gives us a different way of knowing; a way that involves making and testing models of the thing we’re imagining. What would the effects be on our customers/our organization/the market/the world if something like this existed in this particular configuration? Does it feel natural? Does it make us more or less assertive? What changes does it ask of us?

Trying on possibilities is very different from imagining what it would be like to do so. The acts of making and testing (even if it’s just a rough sketch of the thing we have in mind) provide insights that no spreadsheet can account for. Design allows organizations to sample different ways of being in the world without committing to production — a more strategic role than merely making things better and making better things.

Aspire to Ever-Fatter Markers

 

29-3_Cava_Thinking2.jpg
A design exploration for the Dominican Motherhouse by the architect Louis Kahn. Kahn surrounded himself with people who could realize his ideas at greater levels of fidelity. Image: Arcade

 

A design career is a progression from thin markers to fat markers.

When you’re starting out, someone else gives you direction. You’re expected to fill in the details using very fine lines. To do so, you must understand the characteristics of the materials you’re representing on the paper, whether they be code, words, images, or bricks.

Once you’ve mastered the details, you can graduate to Sharpies. You can’t get too granular with Sharpies. This is good since it allows you to focus on the relationships between elements without getting lost in the details. You now understand how things can fit together locally. You can also identify, define, and convey patterns that allow designers with finer markers to work faster.

Eventually, you move up to whiteboard markers. With these blunt tools, you explore systemic issues: how elements relate to each other at the highest levels, how the outside world interacts with the system, how the system will evolve resiliently, who is responsible for what. You do this with collaborators in real-time; this includes stakeholders with concerns that are very different than yours. You develop gravitas and political savvy. At the whiteboard, you have an audience, and the stakes are high.

This audience includes designers wielding Sharpies and fine markers. Now you’re the one giving direction. As the person wielding the fat marker, it’s your responsibility to nurture the people using markers finer than yours, so they move on to fatter markers. You must also bring in new people to take up the fine markers others have left behind.

And what if you’re a team of one? Then you must keep markers of varying widths at hand. You must know which work best in which conditions, and when you need to switch pens. (You must still work on the gravitas and political savvy, by the way.)

You can’t design exclusively using whiteboard markers any more than you can with only fine markers. You need a combination of both. Good design managers help their teams master their skills and broaden their perspectives, and keep a vibrant mix of line widths in play. As a leader, you don’t necessarily stop being a practitioner; you just move on to a fatter marker.