The Broken Caterpillar

In the spaces where I work, we hold three things, above all-else, to be sacred. Focusing on individual strengths, making clear our intent, and making leadership everyone’s job. This is a proven, if not over-simplified, base formulae for team success. As long as you’re providing meaningful work to individuals that aligns with their strengths, and a vision that aligns peoples intentions with organizational goals, the rest will, for the most part, work itself out.

Work places are like caterpillars. The legs all have to move in a smooth, efficient sequence for things to progress.

Work places are like caterpillars. The legs all have to move in a smooth, efficient sequence for things to progress. This “three things” model is meant to keep the caterpillar propelling forward. But like any leadership model worth it’s salt, there’s ongoing maintenance. Things get off-track, individuals intentions wander, engagement sags, work needs re-aligning, etc. When someone’s intent waivers, or when someone is being given work that doesn’t align with their strengths and interests, we have a broken caterpillar. It’s up to us as leaders to find effective ways to get things moving again.

Think of a rowing crew. This simple example of a team satisfies all three work conditions: 1.) all crew members are doing work that focuses on their strengths (rowing, generating power, propelling the boat forward), 2.) they have clear intent (to win, or to beat a previous time), and 3.) they are all leaders (they share equally in the work of rowing and encourage/empower each other). When someone slows down, stops rowing, or drags their oars, you have a broken caterpillar.

Does it help to point out this individual, make an example of them? No. This only focuses on what’s not going right, and even if their performance recovers a bit, the motivation is to not get called out again as opposed to being part of the team win. What’s more, it’s a distraction to the rest of the team, and creates rifts where their wasn’t any before. In short, the caterpillar is more broken than before.

The best course of action is to remind the team as a whole to step back, look at the big picture, and recommit to being leaders and to the intention to achieve their shared goals. In essence, in the rowing example, look at the person in front of you and behind you and re-engage. In our places of work, this means understanding when and why things falter, reassessing work arrangements to make sure they’re aligned with individuals’ strengths, and instilling in those individuals a renewed sense of leadership, a renewed commitment to modeling the behavior and traits that will motivate the whole team.

Develop the Filter, Not the Perspective

A black and white photo of a person pointing a camera directly ahead close up, with the camera lense in focus.

It’s well established that diverse perspectives lead to innovation, a critical component of organizational growth. As long as your organization or agency is articulating and broadcasting consistent vision and value to your customers and employees, you should be enthusiastically collecting as much perspective as you can.

But too often today’s managers operate in a way that suppresses perspective. They assume that they’re position endows them with expertise that is somehow more valuable than those they supervise, and they focus on forcing their perspective on their departments or divisions. This is one fundamental difference between theory X and theory Y managers–between managers who seek control and practice more dominance-oriented techniques and managers to who are more participatory and govern through trust, open-mindedness and empowerment.

A simple example of this is the manager who attends a webinar or conference and edits down the content and re-presents the material to their department, often with their own qualifying content. This is fine, to an extent, as the original content might not all be relevant. But this is also an example of a manager deciding that they don’t trust their subordinates to think for themselves and examine the source content through their own lens. It’s a decision to develop perspective, not filter.

When we talk about filter, we’re talking about the collective experience and knowledge that inform our choices. This ability to filter is critical to survival–it helped our ancestors avoid getting eaten, it helps us make nutritious food choices at the supermarket so we can stay healthy, and it helps us build networks, bridges, and collaborative engines in our places of work. It makes it possible for us to self-select into groups and teams that draw from our strengths and drive the greater good.

Rather than spending time rehashing a webinar, the manager could simply forward the presentation along with a quick recap of how they feel it’s relevant. But that alternative just removes the theory X factor from the equation and doesn’t help those on the receiving end develop their filters. Here’s what theory Y has to say about developing filters.

Be a Coach

Theory X managers are tellers. “Do it this way.” “This is not what I had in mind.” And the death knell of many an organization: “This is how we’ve always done it.” Theory Y managers are coaches who ask questions. “How do you think this will turn out if we take this approach?” “How does this support the project goals?” “What do you envision our next step to be?”

Coaches are critical to organization growth and engagement. They use inclusive language that implies teamwork rather than 1:1 relationships of dominance and subordination. Coaching requires less energy and work–it’s exhausting and inefficient to constantly tell others what to do and maintain a bank of strong opinions. Coaching requires patience and deep listening, both things that co-workers, supervisors and supervised alike, respond to well and appreciate. By coaching through questioning, you’re helping those you manage to develop their own filters in a guided, proactive way.

In our example above, the manager could send along the presentation and ask those on the receiving end to write down five things they found insightful, or five questions the presentations raised, then pool the responses and encourage group discussion.

Make Opportunities for Growth Readily Available and Accessible

Theory X management tends to put people in narrowly defined career predicaments. This is due to a variety of factors. First, managers who dictate rather than encourage self-initiated growth tend to pigeon-hole their employees and drive them to become specialists, and then rely on them to provide a very specific subset of tasks for them. Second, the employee, in turns, feel less valuable and becomes disengaged, preferring to keep a low profile and just “get through the day.”

Get to know your employees’ strengths and skill sets, and align them with work that will help them flourish.

It’s one thing to be really good at a narrow set of things and be celebrated for it. It’s another thing to be regulated to jobs that you don’t necessarily love doing and dread work as a result. Get to know your employees’ strengths and skill sets, and align them with work that will help them flourish.

Especially in creative fields (design, videography/photography, stack development, etc.), it’s important to encourage well-rounded skill sets that cover a diverse set of disciplines. This is the glue that holds teams together–sharing knowledge and bouncing ideas off one another because of overlaps in interest and skill sets. Even in more “disciplined” fields (accounting, i.e.), it’s good to have people job-shadow and take on work outside of their comfort zones. They will develop new perspectives that will pay off in unexpected ways.

In our example, the manager could ask people to identify topics from the presentation that interest them and aren’t necessarily part of their current job description, then follow up individually to discuss what opportunities might be available for them to explore those topics.

Follow the Rule of Thirds

During your one-on-one meetings (you are regularly holding weekly one-on-ones with those you supervise, right?), follow the rule of thirds:

  1. One third of the conversation is about how you can help them with what they’re currently working on.
  2. One third of the conversation is about how they can help you with the work you’re currently doing.
  3. One third of the conversation is about how they can grow and develop their filter, and how you can help.

The first two are fairly straight forward. This is a great opportunity to level the playing field and build rapport and trust with employees by setting your respective workloads side-by-side on the table. The critical and often missed element to one-on-ones is step three. Make sure you’re devoting time to talk about their career paths and how you can help them grow and reach their professional goals. Be a coach, ask questions about their interests and capacity in relation to their current duties. Connect the dots between what they currently do and their potential.

It’s crucial to remember the real goal of leadership – to create more leaders, not followers. Finding ways to develop filters is like sending your team’s brains to the gym. Each time you encourage someone to ask questions and step outside of their comfort zone, you’re helping to develop their filter and their ability to lead others through similar circumstances. A cycle that will pay endless dividends to your company’s bottom line.

Managing Creatives: the Baseline

A black and white photo of nine people rowing a crew boat on a still lake.


Adobe recently conducted a study that made a strong case for the increasing importance of creativity as an essential job skill. Their study dovetailed with another study by the U.S. Department of Education looking at the role of technology in education, which recommends the following skills if America wants to stay globally competitive:

  1. Critical Thinking
  2. Collaboration
  3. Complex Problem Solving
  4. Agency/Self Development
  5. Multimedia Communication

What lubricates this system of skills? Creativity.

Whether you push products down a production line or create and edit rich digital media, creativity plays a role in what you do. Creativity is what we use to solve problems, regardless of size or scope.

So, should you hire for creativity? And once you’ve acquired it, should you cultivate and create a healthy environment for it? Do you own/run/manage an organization? If the answer to this last question is yes, then the answer to all of them is yes. Here’s a cursory, highly-simplified list of management principles to help keep creativity flowing in your organization. They just so happen to be good life skills and general management/leadership skills, to boot.

Use Future-Based Language to Grease the Wheels

Environments with many problems to solve, especially environments that rely heavily on creative input, also include a lot of “noise.” Digital communications flying back and forth, multiple deadlines piling up, meetings that enforce shifting or changing priorities, relationships and personnel dynamics – we increasingly operate in very complex work environments. And we often get bogged down in those details and start to mistake them with the identity of our work or, worse, our organization. Staying competitive as an organization requires a focus on the future. Shockingly, according to Gary Hamel, author of Competing for the Future, the typical firm spends less than 3% of it’s time formulating and executing on a vision of the future. What is your organization doing to anticipate and address future problems? How is the vision of your organization driving its culture, and HOW you approach problem-solving and work, in general? Can your most rudimentary employee, an intern, perhaps, articulate in simple terms your organization’s identity and where it’s headed?

Get involved, however you can, in cultivating and communicating the vision for your organization, and then set to work weaving that vision into your work and that of your teams. In the process, you’ll leave behind the language of the static present and past. With future-focused cultural goal posts in place, your teams will have something to shoot for, instead of just piles of work to “get through.”

Give Away All the Credit

The key concept here is that you’re part of a team, no matter what your position or rank. Creativity doesn’t work nearly as well in a vacuum – ideas are made stronger/better when they are bounced around, and rarely do they come back to the originator in the form that they sent them out into the world.

Praise your team, and authentically THANK them CONTINUOUSLY for their contributions and achievements in the creative process.

Taking credit is not necessary, and it can be quite demotivating to your creatives if they feel like they’re not being given due credit.  Praise your team, and authentically THANK them CONTINUOUSLY for their contributions and achievements in the creative process.  In fact, THANK them for their failures as well!  Failures are the often overlooked or even shunned contributors to the creative process – we learn so much from failure, but our instinct is often to sweep it under the rug or try to pass it off. Taking credit for accomplishments not only dampens others’ enthusiasm for contributing, it magnifies this instinct to bury failure, and you could be missing out on a boatload of creative cargo.

Ditch “But” in Favor of “And”

This takes a little practice, but it’s worth the mental effort and will pay out in spades, not just on the job site but in everyday life.  Stop using the word “but.”  When you are providing feedback and you put “but” in your sentence, the assumption (which is right 99.99% of the time) is that you’re about to get critical. The effect is that your listener immediately has a tendency to disagree or want to negate whatever it is you’re about to say, even if it’s constructive. Or worse, they shut down and tune you out completely. Replace “but” with “and” and watch the magic unfold.

“Hey Margo, I love the layout you came up with, but I think the calls-to-action are buried too much under those strong elements in the middle.”

“Hey Margo, I love the layout you came up with, and I wonder if we could strengthen the calls-to-action a bit, which seem to be buried a bit under those strong elements in the middle.”

See the difference? You’ve included them in the conversation and built upon your initial positive feedback. It also causes you to rethink how you might phrase the concern you have – you can’t help but deliver it in a more constructive, empathetic way.

There’s No Such Thing As an Online Captive Audience

A black and white photo of movie goers dressed in formal wear and wearing paper 3D glasses.


I have a fair amount of nostalgia about flying as a child. I remember with a fondness those airplane safety manuals, the first time I got to visit a cockpit and got pinned with my first set of wings, getting a pack of playing cards from the stewardess so my sister and I could play go fish or cribbage, and so on. And those SkyMall magazines – those wonderful, quirky marketing wonders that held all those exotic products that solved all of life’s little difficulties. You could only annoy your sibling with those directional air ventilators for so long before you found yourself rummaging in the seat pocket through the magazines. The airplane represents the quintessential environment for captive audiences – with nowhere to go, you’re everything short of forced to browse SkyMall.

I remember another captive audience situation I found myself in that wasn’t so nostalgic. My wife and I were in Hawaii on vacation and signed up for a tour of a facility that produced pearls and coral jewelry and gifts. It all started with them loading us and about twenty other tourists on a chartered bus. We were offered a glass of wine during the ride while the tour guide gave us a spiel about the company’s divers and how they sustainably harvest materials from the sea floor. Next we found ourselves getting off the bus and directed into the facility, which was a labyrinth of hallways with windows into museum-like display rooms and videos that showed the divers at work. In the end, we were funneled onto a large showcase room, where several sales associates proceeded to hard-sell us on expensive jewelry items.

These are real situations, both good and bad, that we find ourselves in as consumers from time to time. We’re constrained, we’re systematically compelled, we’re captives.

I was told, ad nauseam, that the only way to clearly show my wife that I still loved her was to buy her a $1,500 string of pearls. We were captives – the only exit was clear across the showroom, hidden behind some trade-booth walls and low hanging lights. The only way out was through the sales associates, and it was questionable whether we would make it out alive or not.

These are real situations, both good and bad, that we find ourselves in as consumers from time to time. We’re constrained, we’re systematically compelled, we’re captives. When it comes to the internet, however, we’re none of those things. A colleague of mine recently told me that it would be a mistake to link off to another site because it could mean losing a captive audience. Not only is this fundamentally untrue, but it’s a dangerous approach to thinking about UX and the basic needs of your users. In an age largely dominated by search and API-first infrastructure, the user is king, and there are several compelling reasons why the internet, rightly so, is not the domain of captivity.

Low Switching Costs

Your users are constantly one of many touchpoints away from bouncing from your site – clicking out, closing their browser, abandoning a purchase, etc. Sure, sometimes the reasons are because you’re not doing a good job of compelling them to take an action, but there are plenty of external reasons that users exit.

Bounce rates get a bit of a bad rap – there are scenarios in which bounce rates, even high ones, are healthy.

Bounce rates get a bit of a bad rap – there are scenarios in which bounce rates, even high ones, are healthy. A high bounce rate can mean that the page in question has done a good job of explaining or covering the topic of interest, and the user is now off to gather a different context, to compare products and pricing, or perhaps to get some other, maybe tangible, affairs in order before making a decision. I talk to companies and managers all the time who are trying to find ways of drastically reducing or even eliminating their bounce rates, often without a clear understanding of what a bounce rate indicates or how it might be aligned with their goals and primary UX actions. With a strong sense of your site’s core and how it aligns with your strategic goals, some A/B testing is all it takes to “optimize” your bounce rates and other key metrics.

Unless you install malicious software with the intent to infect your users’ devices so that they’re locked onto a page, the fact is web transactions, by themselves, have low or even no switching costs. As internet marketers, we have to be compelling without being restrictive.

Low Hanging Fruit

Some recent studies have shown that we use the internet much in the same way that our hunter-gatherer ancestors kept themselves fed and clothed. We hunt for what we want, and we’ll keep hunting, regardless of where the trail leads, so long as we feel that we’re still tracking what we’re after and making progress. I rarely, for example, rely on just one site or app to get my news. I might see something that interests me on Twitter, click into it, and then leave the site to corroborate the story elsewhere or research a particular topic. It’s virtually impossible for a news organization to provide the entire context and scope of information in regards to a news item or topic. Rather than trying to keep an audience captive by trying to cover everything, it’s better to be the expert or leading authority (again, be compelling without being restrictive) and control the acquisition channel(s). There’s plenty of reason to think, in fact, that overwhelming your user with too much information or context will drive them away and dissuade them from adding that item to their cart.

Wikipedia might come the closest of any site to attaining captivity status. One can certainly click from topic to topic and not need to leave the confines of wikipedia.org in their quest of knowledge. Wikipedia brilliantly delivers comprehensive content as low hanging fruit. But even Wikipedia relies heavily on outside sources and articles to fill it’s pages, and you just won’t get the same user experience reading a wiki article on NASA, for example, as you will from going to NASA’s site. Both are valuable, depending on what you’re trying to accomplish.

Low Investment, Long Tail

It’s estimated that 140,000 website get created every day worldwide, and there are well over 1 billion websites in existence. Talk about redundant information. SEO is largely a battle for the attention of users who’s attention spans are getting shorter and shorter, and who demand information faster and faster. Speed trumps accuracy, most of the time. The internet’s tail is long – you can find over 16 million articles on Google related to “How to Mix a Martini.” For this reason, the API market has expanded, in part, as a response to the need to link information more accurately and appropriately. Rather than thinking in terms of a singular site that needs to dominate the information landscape on a particular topic or for a particular niche, one should consider what a system of information around the topic or niche looks like, and how it might be navigated. Persona development comes in handy in this regard – try to obtain an accurate picture of who your users are, what channels of communication they prefer, and what auxiliary systems, sites or services they consume. Partner, as much as you can, with these complimentary systems and mediums. Or try to buy them out. Just don’t waste your time trying to recreate content that might presented better or more prominently elsewhere.

Repeat this Mantra: Quality Over Quantity

There’s a massive spectrum of sites and systems, in terms of core purpose, to be sure. Ever site on the web could be described as falling on a sliding scale of “approaching a captive experience” in some sort of terms: from SAAS vendors’ marketing sites to sprawling government sites. But the very nature of the internet is ease of access and delivery of information. Since it’s virtually impossible to win at quantity, go for quality. Chances are, my 16,000,001th article on how to mix a martini isn’t going add a whole lot to the conversation, unless it’s truly innovative and offers something new and highly valuable to martini lovers.

With enough marketing savvy and the right strategy, you can certainly create perceived switching costs and increase a user’s reliance on your site or application, which will lead to better click-throughs and conversions.

There’s nothing wrong with striving for something that resembles a captive experience. With enough marketing savvy and the right strategy, you can certainly create perceived switching costs and increase a user’s reliance on your site or application, which will lead to better click-throughs and conversions. Just don’t insult your users or take them for granted. Do your homework, develop your personas and strategies with care. Be aware of the competition and complementary systems and applications, and strive for the best experience that you can deliver, given the big picture.