How to Make Your Startup Communications Antifragile


As a coach, I often wish that I could tell clients how “easy” it is to craft persuasive communications that respect the integrity of complex ideas while winning over the audience. But the truth is that using language and visuals to convey thought is challenging work, even using AI as your helper.

Building any communication product—such as pitch deck, a cold email, a website, a one-pager, or a blog series—is like constructing any physical product, such a chair or a house. Try to cut corners, and you just won’t get the personalized product you need to grab your audience’s attention and nurture trust.

For more than 20 years, I’ve taught an “agile” method for generating communications, which involves frequent touchpoints with the target audience and multiple iterations to get the message right. Nassim Nicholas Taleb, a former trader and the Distinguished Professor of Risk Engineering ant New York University’s Polytechnic Institute, is now helping me understand why this approach works so well.

When you assume that your first communication attempts will be imperfect, you build an error-correction loop into your development process. As a result, you create communications that become stronger each time they “fail.” To borrow Taleb’s term, your messaging and collateral become “antifragile.”

Customer discovery for communication products

When I work with clients, as either a coach or a writer, all I can promise is to help make the creative process more streamlined, more effective, and more enjoyable. Reaping those benefits, though, first requires a mental shift away from the belief that producing communications is a matter of “once-and-done.”

When it comes to finding the right language (written and visual) to win over your specific audience, aiming to “get it right the first time” proves counterproductive. That perfectionist attitude racks up significant costs: wasted effort, high fees for creative services, and missed opportunities to genuinely connect with the people you want to reach.

In contrast, pursuing an iterative approach means embracing failure as the path toward success. This is the wisdom behind the customer discovery process, right? So why do so many entrepreneurs apply it only to physical or technological products, not to communication products?

When I help entrepreneurs with the communication skills it takes to navigate customer discovery conversations, I give them this warning: “If your discovery conversations don’t surprise you, then you aren’t leading them effectively.” In other words, if your customer discovery doesn’t upend some of your assumptions, then you’re not risking enough with the questions you’re asking.

The validation process always involves invalidation as well. Only by discarding features your audience considers useless can you shape the product they’ll crave. Likewise, only by discarding false assumptions about how to communicate with your audience will you learn how to connect with them at that deep level where trust grows.

Why aim for antifragile

Embracing failure as part of developing communication products gets you out of the sand trap of “spray and pray,” where you craft your message once and disseminate it widely. Welcoming missteps as part of the process enables you to create communications in collaboration with your audience. The result: communication products with the quality Taleb calls “antifragility.”

I’ve just dived into Taleb’s 2012 book Antifragile: Things That Gain from Disorder, which I recommend as a heartening read for any innovator. Taleb rails against our culture’s obsession with de-risking complex systems and situations. Instead of trying to protect the fragile, he says, we should think about how to create the “antifragile.”

Here’s how Taleb defines “antifragility”:

Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile.

Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better (p.3).

Communication is by nature a process subject to random shocks. As much market data as you gather, you’ll never be able to perfectly predict how a person will react to your words and visuals. People aren’t machines, or Vulcans like Dr. Spock, so they don’t always respond in ways we think logical.

That doesn’t mean we shouldn’t create detailed personas, analyze market data, and rehearse for important meetings. But it does make nonsense of the notion that we can craft the perfect brochure or website without subjecting it to the “random shocks” of audience interactions.

Once you let go of the belief that great communications hit a home run on the first try, you can start creating communications that get better with each swing. Your third (or thirteenth) draft won’t just be a slightly modified version of your first; it will be a creature that has grown to become stronger and fitter for the purpose it’s meant to serve.

How to create antifragile communications

The evolutionist perspective is significant because antifragility, in Taleb’s view, is the property of organic entities. As Taleb explains, inorganic things tend to be fragile whereas organic things exhibit antifragility. Under physical stress, a piece of plastic breaks, but the muscles of a bodybuilder repair themselves and become stronger.

Communication, we must always remember, is an organic process. When I present a first draft to a client, I often compare it with a lump of dough that we’ll knead and shape together. Taleb has helped me realize why I use this metaphor instead of reaching for mechanical concepts such as “tinkering” or “fixing.” Dough is an organic substance, and the process of flattening and punching the dough activates the gluten that will cause it to rise during baking. The stress of kneading makes the dough more elastic and the bread tastier.

Reframing communication as an organic activity is the first step toward creating antifragile communication products. Here are five practical tips for putting that understanding into action:

#1: Design stress tests

A few years ago, a startup asked me to develop a suite of marketing materials, including a presentation deck, website, and white paper. At our kick-off strategy session, it was obvious that the team had thought through their value proposition backwards and forwards. But they hadn’t yet had the chance to communicate it to real customers and observe their response.

Rather that jumping into the collateral I’d been engaged to produce, I suggested that we add, at no charge, an additional item: a one-pager to use as a test piece. We needed an external audience of real customers to validate the language that resonated internally.

“Do you have any customer meetings coming up?” I asked.

Fortunately, the co-founders were about to head to a conference where they’d be meeting their ideal clients at an exhibition booth.

We quickly created a one-pager, using the language and visuals the client felt sure would land with their audience. The co-founders and I discussed how they’d observe the way people interacted with the headline, key points, and visual design.

The conference became a pivot-point in the startup’s messaging. The co-founders had terrific conversations with the people who stopped by their booth and picked up a flyer. They also discovered that the messaging they found so clear left their audience cold.

We had successfully put the first expression of their value proposition through a stress test, and it had failed. Great news!

Because the co-founders had treated their exhibition booth as a testing lab, they could report on specific aspects of the messaging that had worked and those that had flopped. As we turned our attention to developing larger communication products, such as the website, we were able to build stronger messaging with clarity and confidence.

#2: Invite friendly collaboration

You can spend hours, if not days, playing through “what if” scenarios involving your buyer personas. The best audience to give you feedback on your messaging is always an authentic audience.

Early in your creative process, invite real prospects to give you feedback on your draft. The key is to choose those prospects carefully. Your best collaborators will be people who are keen to see you succeed. These could be people who participated in your customer discovery process, for instance, or people in your network who can easily identify with your ideal customer.

One of my clients calls such folks “friendlies.” Friendly reviewers have bought into your value proposition, so they understand what you’re about and why it matters. They’re well-positioned to give you constructive feedback because they already grasp your intended meaning and can help you express it.

There’s always a place in the creative process for naysayers as well, those reviewers you can count on for a merciless critique. But don’t overlook the value of an appreciative audience with both the background knowledge and the goodwill to help you fine-tune your messaging.

#3: Develop assessment criteria

A wise colleague once told me, “A piece of writing is never finished. You just decide to abandon it.”

What’s true of written documents also applies to slide decks, animated videos, and any other communication product you can name. You’ll never reach perfection. Consequently, it’s easy to get stuck in a loop of feedback and rework that goes on and on.

As Taleb points out, just enough stress on an object or system will strengthen it, but too much stress will break it. When you’re developing communications, you must be able to recognize when to keep criticizing and revising and when to consider your draft “done” (or “done for now”).

This is impossible to do, however, unless you and your team agree on objective criteria for assessing the quality of a draft. Without such standards, it’s too easy to waste time arguing over personal preferences, which may or may not be anchored in sound principles and practices.

The remedy to such chaos is to create an orderly approach to assessing a communication product. For some products, this could be as simple as a checklist, but for most products, I recommend a scorecard. Here is a basic scorecard for an infographic, for example:

The more complex the communication product, the more detailed the scorecard should be. It’s also possible to develop a single scorecard to apply to various kinds of communication products across an organization. Below, for example, is part of the scorecard I use in one of my group programs. It has proven relevant to knowledge translation (KT) products as diverse as podcast episodes, blogs, impact reports, presentations, and infographics.

#4: Establish a review protocol

Optimizing antifragility usually requires more than a draft or two. One client told me that he and his team had prepared 27 versions of a proposal, and that didn’t surprise me. I think my personal record is 39, which I reached while revising a complex eLearning course a few years back.

To cope with multiple revisions, you’ll need a system—even if you work mainly on your own. When I work with a team, one of my first questions is “What’s your file-naming protocol?”

My own protocol is simple: <file name_ver#_initials>.

As each reviewer makes comments in the document, they update the version number and change the initials to their own. For example, let’s say that Shane Williamson and I are both working on a document called “Project Plan.” If I started the document, I’d name it <projectplan_ver1_DH>. After Shane’s review, he’d label it <projectplan_ver2_SW>.

Besides a method for file-naming, you’ll also need guidelines for commenting on and editing shared documents. Here are some of the practices I use:

- Provide summary comments to put marginal comments in context.

- Call out strengths as well as weaknesses. (The easiest path to antifragility is to build on strengths.)

- Change the color of comments to a color other than red. (Red makes edits seem punitive, not constructive.)

- If someone else “owns” the draft, use a comment rather than making a direct edit. (You can suggest a rewording in the comment.)

- If phrasing is unclear, ask a question rather than trying to correct it. (How can you correct what you don’t understand?)

#5: Control the means of production

I’m no Marxist, but I have learned some tough lessons what happens when you, the founder, become alienated from the fruits of your communication labors. While you’re in iteration mode, make it as easy as possible for you or your team to update drafts.

When you’re faced with a tight deadline, or when you feel doubtful about your own abilities, outsourcing writing, graphic design, and basic video editing may seem the best solution. But what happens when that beautiful brochure your freelancer created in Adobe InDesign needs a quick edit to the color scheme so you can get it to a new prospect by EOD?

Then, my friend, you’re stalled, at the mercy of your freelancer’s schedule and subject to their fees for change requests. When you’re a startup, you can’t afford that kind of delay or hassle, no matter how gorgeous the end result.

Create a communications tech stack that will enable you to work efficiently and produce high-quality products without having to over-invest in training. While you’re iterating, create collateral in Canva or Microsoft Office. When you get to your ready-to-release version, then you can, if time and budget permit, take the time to use more complex software (or hire someone to use it for you).

Controlling the means of your creative production takes a bit of setup, but it’s definitely, as Marie Forleo says, “figureoutable.” Take a cue from the teenager-next-door and YouTube your way to becoming a competent copywriter, graphic designer, or video editor. Or sign up for any number of online courses in those areas, read a book, or get a few sessions of one-on-one coaching.

At the same time, keep an eye out for the latest tools that can smooth out your workflow while keeping you close to the creative process. For example, I used to dread video editing until I discovered Descript, an application that allows you to edit video via the transcript.

“If you want to become antifragile,” writes Taleb, “put yourself in the situation ‘loves mistakes'" (p.21). The easier it is for you to access and edit drafts, the better equipped you’ll be able to do that with your communication products.

In Taleb’s view, fragility and antifragility exist on a spectrum. It’s also possible, as the above quote suggests, to move along the spectrum, to “become antifragile.”

As you develop communications for your startup, where on the spectrum is your creative approach? Are you hesitant to put any message out into the world before it’s perfect? If so, you’re operating from the fragile side of the scale.

Or are you willing to test early versions of communication products with “friendlies,” to invite collaboration, and to set up the internal processes that will let you iterate quickly? If so, then you have at least the attitude, and probably some of the skills, to operate from a place of antifragility.

Either way, you have the power to cultivate greater antifragility in your communications. And learning to “love mistakes” in communication will help you “fail fast” in other aspects of your business so both you and your organization can learn and grow.

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[1] Taleb, N. (2012). Antifragile: Things that Gain from Disorder. New York: Random House.


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