Getting to the punchline, it goes like this.

If peers perceive you as smart, senior, or experienced, your use of AI is perceived to be a good thing! You are being proactive by outsourcing administrative and other lower order work so you can work on higher order, strategic items. Good for you!

If you’re perceived as junior or inexperienced, your use of AI is perceived by a bad thing! Clearly you can’t hang with people with credentials, certifications, and tenure, so you’re using AI to shore up your deficiencies. You’re a poser using AI to fake who you are not. Shame on you!

I’m kinda/sortof embellishing a bit, but not by much. We see AI as either a way for smart people to get more leverage as well as a way for ignorant people to fake it.

This is an important cognitive bias to be aware of, because it can amplify mistrust to people based on age, sex, role, experience, etc. We should all be using AI to amplify our abilities while not holding it against anybody.

At the very least, we should be aware how we’re not applying our perceptions evenly, and that can lead to unfair biases.

The Matrix: “I know Kung Fu”

In The Matrix, Morpheus plugs Neo into training simulations that allow him to achieve mastery level skills in minutes.

WALL•E: “cupcake-in-a-cup”

In WALL•E, we first see humans living life like sloths: confined to chairs, watching screens, with blended sugar meals (“cupcakes in a cup”)

Why am I juxtaposing these two scenes?

To me, they represent the two extreme ways which humans approach AI:

1. Rapid upskilling to learn more and perform faster, smarter, better.

2. Outsourced thinking, handing over all human agency to AI.

The latter is a big fear for AI skeptics. They see a society where people stop thinking because they just listen to whatever ChatGPT tells them to do. After all, if AI is supposed to be smarter than them… why not?

The other approach is more intentional and empowering. Humans always had access to vast sums of knowledge (ie libraries and The Internet). However, it still took a lot of searching, sifting, and synthesizing to find the right facts, for the right context, and apply them in the right way.

AI shortcuts this process in a profound way. It’s like having 24x7 access to the smartest people across every field imaginable. LLMs can do the heavy lifting of connecting the dots in ways that can help us get to more of those Eureka moments. It’s the perfect embodiment of the data, information, knowledge, insight, wisdom, impact meme below.

Of course, LLMs are still a far cry from Morpheus being able to download skills into Neo’s brain (which is what Neurolink will eventually do).

However, if you approach AI like Neo (trying to rapidly acquire skills), you can run circles around people taking the WALL•E approach of being spoonfed blended answers without taking the time to understand WTF they are consuming.

The best-known exception is Amazon.

They have two policies to prevent meetings from slipping into the abyss.

1. The meeting owner creates a detailed, written document.

2. Before the meeting starts, everyone reads the document.

This doesn't guarantee a productive meeting. Someone could hijack the conversation to talk about God knows what. However, it ensures every meeting has a purpose and everyone is prepared.

Compare this to recurring status check-ins.

My experience is that most people show up late and unprepared. Because the meetings are ineffective, people try to multi-task, further reducing their effectiveness. Sometimes a leader drives the meeting, but often it becomes a watercooler conversation. Half the people on each call may not need to be there, but continue to show up because it's on the calendar.

Familiar?

It happens to almost everyone UNLESS you are extremely disciplined.

What's the solution?

You can double down and salvage a previously productive meeting.

Or take the Shopify approach: purge everything periodically.

Delete all recurring meetings.

Resist the urge to replace them! See if a meeting can be an email update or occasional async Slack conversation.

If you need to add something back in, call it something new with a new agenda. Don’t just add everyone back. Be strategic. Don’t just pick 30 or 60 minutes because they’re the defaults. Keep it to a tight 15. Maintain a 1 meeting, 1 goal focus.

It's not a cure-all, but it's better than limping along doing the same ole same ole for the past 1-10 years.

Sometimes you need to change things up. A change of attitude, posture, and positive pressure can make a meeting more creative and effective.

Business and tech leaders were stressed about AI but in an uncharacteristic way.

Usual frame: AI is going to put us all out of business.

New insight: Humans are struggling to apply AI in their business.

Ironic, no?

Here, we are witnessing an explosion of superintelligence in the form of large language model (LLM) models. Yet, the bottleneck to adoption still remains... the less intelligent humans.

In the past two weeks, I've had over two dozen conversations with business owners and leaders. The common theme? Most people are nowhere near applying AI in a meaningful way within their company. And if they are, they are terrified that their peers or competitors are one or more levels ahead of them.

Digging Deeper

A problem with trend spotting is you can extrapolate from a small data set to come to an incorrect solution. After all, I am in a specific industry in a specific role in the middle of the country working with early stage startups. My next question was, does this trend hold globally?

I dug deeper with OpenAI's Deep Research. The key highlight was that while AI is being applied and making an impact, as many as 40% of teams and companies are lagging behind where they want to be.

Companies are trying various approaches to address this issue. Public company CEOs are making public proclamations that all employees must use AI. Team leaders are blocking off their team's calendars to do 1-2 day hackathons. And people are hiring AI coaches and trainers to help skill themselves up.

Last week, I predicted that the only way this issue could be resolved in the long-term would be through the emergence of a new role. Call it an "AI Lead" or a "Chief AI Officer," but companies would have to hire specialists that would be able to

1. Keep up with trends.

2. Find high ROI places to apply AI to solve business needs

3. Train team members and implement lasting culture changes

And, bingo! Today, we are witnessing this new role emerge.

Tweet Source

History Rhymes

Anyone familiar with the cloud software space in the mid-2010s may be aware of the role of a "DevOps engineer." Initially, it was just a philosophy of how businesses shipped software better and faster. Everyone was supposed to embody it, but that's a huge burden to place on every employee on every team.

Eventually, dedicated job functions and roles emerged. These DevOps engineers were sometimes glorified labels, but the point was businesses knew they needed someone with the skills, experience, and intention to ensure the company could benefit from this philosophy.

The same is happening with AI.

Attempts to mandate "well, everyone needs to learn how to use AI" won't be enough. Individuals still have to spend the majority of their day performing the job functions at hand and can't dedicate an additional 5-10 hours per week to continually upskill.

No, we will need specialists (at least for now) to help companies achieve sufficient AI fluency so that this can self-sustain. Until it becomes as common as typing skills.

Until then, expect to see a new wave of AI training products and services to help everyone get AI into their businesses.

Time to catch this trend!

Imposters think they lack sufficient knowledge or experience to achieve the goal at hand and believe others will catch them.

The Curse of Knowledge is the other extreme. A person has specialized knowledge and experiences that make it trivial to achieve the goal at hand, and they think everyone else can do the same. Why? "Because everybody already knows this."

Spoiler alert—they probably don't.

I experienced this phenomenon multiple times this week.

First, in a CTO Slack channel. A member had joined a new company and was sharing their week one findings. Shockingly, the senior developers were committing numerous junior-level mistakes, ignoring best practices that had been codified and taught for over a decade. I'll spare you the details, but they were bad enough that I blushed while reading them.

Second, in multiple discussions with senior leaders about their team's AI fluency. I had expected that most companies would already be learning and applying the latest and greatest tools, achieving 2-5x gains in productivity. NOPE! Most were struggling to even get their lead engineers to try. Worst, many were struggling with where to start, where to invest their time, and what tools and playbooks to run.

And so on and so on.

In every case, my first instinct was to assume that the things I found easy (after paying the price of time, money, and energy to learn them myself) would be easy for others.

This, my friends, is The Curse of Knowledge biting you in the ass.

So why does this happen?

I think the best explanation I've ever come across is XKCD Comic 1053: Ten Thousand.

Given we all start with no memories or facts in our brains, everyone has to be exposed to a fact for the very first time. Using simple math assumptions, this means that every day, 10,000 people in the US encounter a fact for the very first time.

This is the perfect antidote to "But Everybody Already Knows This" thinking.

And if you're in the business of training or mentoring, it means there is NEVER a lack of opportunities for new users or customers.

If what you have is valuable to learn or know, there are 10,000 new potential leads every day.

And now you know that!

People love it when you care about them. One of the ways you can do this is to remember the important things they share with you. It sounds like common sense, but it's not common practice. That's why it often surprises people. They are used to people forgetting about their sick mother or their kids' names. If you remember them, they take notice.

But let's face it, that's a lot of work. And you can only do that with people you know.

When meeting new people, it's a good idea to do some digging on the web to learn about them. The more you know about their interests, the better your odds of connecting with them.

Unfortunately, this sleuthing can take lots of time to find, synthesize, and remember.

Enter: OpenAI's Deep Research.

Many of the simpler ChatGPT AI models are optimized for speed with decent accuracy.

However, this can lead to very shallow details from the first few websites in a search result. So if those search results rank high, bingo. But if that's not the case, the result can be weak or non-existent.

Deep Research is optimized to keep pressing for 10 to 20 minutes, using each webpage as a potential jumping-off point to find additional resources. It also reasons longer and harder, trying to make educated decisions about follow-up questions and queries to pursue.

The net result? A comprehensive, 10-20 page report about a person, their company, and suggestions/advice on what you may or may want to ask based on the objectives of the call. All information contains source links that you can visit and verify yourself.

This is a game-changer. I've done this for the past 10 calls with people I've never met. It gave me tons of information about them to break the ice, find rapport, and show them that I cared enough about the call to do my homework.

Sample Prompt

Here is one I recently used before an investor meeting.

I'm meeting with VC firm X.

• Website https://www.company.xyz/

• LinkedIn https://linkedin.com/in/company.

About me:

• I'm the CEO of Y

• We focus on Z

• Our pitchdeck is X.

• My LinkedIn is https://linkedin.com/in/rickmanelius.

My goal is to be maximally prepared for this 1st round of conversation, so I would like to know the following:

1. What's their investment thesis? This includes the types of projects, themes, and teams they invest in.

2. What is their typical level of investment. Are they very early with smaller checks? Or are they typically a lead investor through a series A?

3. What is their appetite for projects that are equity only vs ones with a token. Will they only/solely invest in projects with a token?

4. What is their current exposure to projects in my sector? Are they excited about that category, or are they more focused on other sectors of the space

5. Do you recommend any specific insights, tips, or strategies with them versus other investor conversations?

Please summarize any announcements or milestones in this company in the past 12 months.

Please summarize any key information about person X, including anything relevant they've been talking about on social media in the past 3-6 months.

Compare our LinkedIn profiles and determine if there are any mutually overlapping experiences around companies, locations, education, etc. Please find any areas of rapport.

Summarize into a 1-pager that I can read a few minutes before the call and be ready to rock.

Starting Smaller

This may be overkill for you. To get started, you can do something even simpler.

"I'm meeting X about Y. Here's their social media handle Z. Please summarize any key news about them or top interests they have."

Repeat and Automate

This may seem like a lot of work at first.

However, if you make these into templates, you can swap names, companies, and links in under a minute. This kicks off the equivalent of 1-4 human hours of searching, analyzing, and compiling a report you can read in minutes.

If you want to go crazy, you could rig this up to your Calendly and Zapier, automatically kicking off a job to do this research whenever someone schedules a meeting with you. Bonus points if you have it append the research right to the calendar invite for you to review before clicking on the Zoom link.

That said, start small and get a few wins under your belt. From there, the sky's the limit.

I’m a huge fan of Wardley Maps. It’s a framework that helps entrepreneurs compete in a dynamic marketplace. In an era of accelerating change, the ability to assess your current situation rapidly and make good decisions is crucial for success.

My key takeaways from the framework are as follows.

All technology follows an inevitable, 4-phase evolution.

1. Genesis (i.e., the first transistor invented in a lab)

2. Custom

3. Product

4. Commodity/utility (i.e., trillions of transistors on billions of CPUs)

All technology stands upon other technology.

• Your app runs on Vercel.

• Vercel runs in the cloud.

• Cloud data centers need software and hardware.

• Hardware needs networking and electricity.

• Electricity comes from power plants.

All parts of the stack are evolving at once.

• Your industry may be immature, relying on delivering custom software solutions.

• Over time, patterns will emerge, and products will come out.

• Also, the tech you rely on will also become better/cheaper products and commodities.

Becoming aware of where all the pieces are in their own evolution helps you make better business decisions in the following ways.

• Knowing when to outsource vs build your own.

• Knowing when the industry is about to shift from custom to commodity.

• Knowing what strategies and tactics work best in which environment.

I could go on and on, but I think it’s best to learn from the man himself. Simon Wardley came up with this while attempting to navigate his business in a complex and changing tech environment. The resulting framework makes it easy for other CEOs/business leaders to assess where they are and where things are going.

And in the age of AI, where we are seeing a massive acceleration of change, places within the map are going from genesis to commodity in months to years instead of years to decades. This increased speed means that some businesses will be building towards a future that is already out of date, and it’s better to abandon and figure out the next place to attack.

If this sounds intriguing to you, I’d highly suggest reading the first five chapters of his series here.

Below is a sample map from Simon showing both a value chain and where the different pieces of said chain exist at each part of their own evolution. Being able to view your business in the same way can be powerful.

In layperson's terms, they switched from requiring humans to maintain a global design file to allowing AI to write its design elements on the fly.

In technical terms, they abandoned global CSS templates rooted in a global branding guide in Figma and instead let AI generation tools generate Tailwind code.

Why was this change profound?

Practices around CSS (cascading style sheets) have steadily improved for almost two decades. Most of these best practices revolved around groups of humans managing them to optimize their workflow. Without a unified workflow, designers, and developers can easily trip over each other.

But that all changed when AI software development tools like Cursor appeared. After all, if AI is writing more than 90% of the code, then it can handle all the overhead of managing the style changes as well (instantly).

Driving the point home, one software release completely changed the calculus of what constituted a best practice for an industry of 200,000 developers. If people were managing it, then a unified CSS document was critical. But if AI was in charge, this was unnecessary.

AI is causing these paradigm shifts to happen more frequently. Eachdustry best practices are being challenged (and, sometimes, changed overnight).

This is a blessing and a curse. The blessing is that it lowers the barrier to entry for people joining this profession. The curse is that we will have to constantly change how we work to keep up with new, evolving best practices.

In short, the half-life of best practices might change from 2-10 years to 2-10 months (or less). That's a profound change.

The following article was originally published here at drud.com.

My bold claims:

1. Every feature within a website RFP can be delivered with a low, medium, and high level of effort (LOE) solution.

2. While the difference between low and high can be measured in single or double digit percentage (e.g., 1-99%), the difference can sometimes span several orders of magnitude (10X to 10,000X).

3. One or two of these massive discrepancies can kill the budget and, as a result, the entire project.

4. We can learn a lot by reviewing GI Joe, the line item scenario.

Why Do I Believe This?

I’ve spent over a decade in the web development space working on the project budgets ranging from the very small (circa $1,000) to the somewhat large (circa $1,000,000 account). I’ve also worked across all stages of the project, ranging from pre-contract as a sales engineer to post-delivery for ongoing iteration and improvement. During this time I’ve experienced (much to my joy) spectacular successes. I have also experienced (much to my dismay) complete and utter failures where the delivery of a 30K project was 4-5X over budget.

Oops.

When these things happen (and they will happen), there is a lot of focus and blame on the estimation process. Unfortunately, I’ve observed that most people and teams spend time in the wrong places. Too much time is spent trying to gain an additional 10-20% of precision when the real issue is they have completely missed an important detail that moves the level of effort up or down a level of magnitude. This is particularly true in web development. Vesa Palmu, the former CEO of a 200+ member web development agency, once stated that “With Drupal features are cheap and details expensive.” This quote has struck a chord with me the second I heard it because it mirrors a truism that I’ve seen again and again: that a single feature can span between 5 minutes and 1,000 hours. You may be skeptical, and that’s fine. I’ll illustrate this with analogies and prove it with some real-world examples from the field.

Author’s Note: This is ONE expanded aspect of my talk: Estimates, Expectations, and Evolution During a Project's Journey from RFP to Release, which I will be presenting on at Drupalcon Nashville. The recorded presentation and slide deck will be linked here.

Let’s begin!

It Started Off So Innocently…

The first pass through an RFP reads so innocently. While I don’t discount the value of missions, visions, goals, and dreams, the real work starts once you get to the subheading marked “Requirements,” which is often represented by a bulleted list. If you’re lucky, you’ll get a description that is at least a couple of sentences long for additional detail and context.

GI Joe, The Line Item Hero

However, imagine coming across a line-item request that containing two simple words: “GI Joe.” Now, of course, this is a website RFP, but let’s further imagine the client wanted an actual, physical action figure as part of their deliverable. At first, you might scoff, but this client seems serious about this request because they did include a graphic and stated that it would go along with the launch of their online 80s nostalgia store.

With no additional information, what would you even guess as a starting point? 5 minutes? 5 hours? Let’s see just how extreme we can make the overall LOE.

99.9% of us might start with the expectation and assumption that the client merely wants an off-the-shelf GI Joe. However, anyone who has built a website has realized that assumptions are not always correct.

The 5-Minute Solution

At first, you might think, “This is easy! I’ll go to Amazon.com, find the first action figure that looks GI Joe-ish, and Amazon Prime two-day ship that stupid thing to their office.” The longest part is filling out the shipping address for the client’s office.

The 1-Hour Solution

The client receives the package but then says “Welllllll… I was looking for a specific outfit, one that matches our company colors.” You think, no problem! Your resourcefulness kicks into high gear, you find a second GI Joe of the same height but with an outfit that kinda/sort of matches the style on the RFP letterhead. You then ship both action figures to your office, where you then swap clothes, repackage, and ship to the client.

The 10-Hour Solution

You then receive a message from the client. “Welllllll… this solution is certainly better, but it needs to match our branding guidelines exactly. See the attached PDF with exact Pantone colors.” Again, no sweat… maybe. You print out the PDF hoping that you did a proper job of color syncing before you high tail it to the nearby home depot. There you do your damndest to try, and color match the pain for the shirt and pants. An hour later you are Google searching while trying to Craigslist or Task Rabbit a designer that can apply the paint in a way that doesn’t look like a four-year-old did it. By the end of the day, the GI Joe with somewhat dried paint found it back into a package and sent over to the client.

The 100-Hour Solution

The client calls, squeezing with delight! “It’s almost perfect!” Almost? He then goes on to tell you that he forgot one critical bit, that the action figure has to be two inches taller to exactly match the other six that will be featured at the retail stores grand opening the same day the website is launched. Your heart sinks. So do you get out a blowtorch and melt the plastic? Or do you attempt to get a Stretch Armstrong doll and get it the right size before trying to freeze the body in place?

Then inspiration hits. 3D printing! Of course, you’re back on Google, but this time searching for a contractor with Autocad skills. You’re also searching for a more talented artist that can paint and match the skin tone. Additionally, you hope/pray this same person can sew (from raw materials) the shirt and pants to match the size.

At this point, this one feature is almost a third of the 300-hour budget, but you’ll try and skimp and save on some of the development tasks.

The 1,000-Hour Solution

The client hears your story of how you went above and beyond for them. They are impressed and eager to see the new deliverable. TADA! It looks very, very impressive… but something is not quite right. Yes, you fixed the height issue, but the 3D printer (using a low-end model to keep costs down) has left the surface with a somewhat grainy texture. And the skin color is not only off, but it’s literally flaking off because it didn’t bind to the plastic.

The client tries not to hurt your feelings, but they firmly insist that they need

1. The body proportions, look, and feel of the 5-minute solution.

2. The clothing style of the 10-hour solution.

3. The colors of the 100-hour solution.

4. The height of the 1,000-hour solution.

And while you’re at it (NEW IDEA), can you change the gender? And the owner is heavy into metaphysics, so can you also insert a rose quartz heart into the center even though nobody else can see it (but maybe they can sense it)?

The 10,000 to 100,000 Solution

If the project hasn’t gone to a legal dispute by this point, it’s a bloody miracle. Still, the engineering mind will still try and solve problems that are far beyond what any sane budget would allow. Maybe you go directly to the manufacturing plant and try to create a new, one-off mold. Maybe this gets you back down to 100 or 1,000 hours (depending on how fast they can retool their machines), or maybe it opens yet another can of worms.

The Aftermath

Ultimately, a $10 GI Joe with small yet “must have” changes can cost $10,000 to $100,000 to produce. And in the end, would anyone at the grand opening even notice or care about the small differences in size, color, and outfit?

It’s not the client's fault (usually). It’s not always easy or obvious for them to know when a “simple” change request will do this because the outward changes appear too trivial and they mask all the behind-the-scenes heroics that (sometimes) need to occur.

It’s also not the manufacturer's fault that they didn’t (or can’t, or won’t) make every conceivable version of a GI Joe action figure. In their business, it’s a game of margins, and they know that a generic, mass-produced version will meet 90% and this will maximize ROI between the company (profit) and the people that collect them (happiness).

There are many parallels to draw in the Web CMS space. Solutions like WordPress, Drupal, Magento, etc. provide a ton of value out of the box, but seemingly reasonable requests can push the project to require a significant amount of customization that can kill a budget and therefore the project itself. Let’s explore.

eCommerce Functionality

In Drupal feature are cheap, and details are expensive. - Vemu

This example hits close to home because it includes several actual project outcomes woven together as a singular example. It is also a cautionary tale because clients (usually) try to both squeeze in features while squeezing down the budget. When this happens, we can begin to rationalize how the project is still possible if more features are moved into the “low” end of the estimate. This rationalization is a trap because clients do not always fully realize how and where a change will move them up or down an order of magnitude.

One example that I used for years was a Drupal 7 site with Drupal Commerce. The requirement included a store that had coupons and sales tax. Both features by themselves were trivial and could be installed within 1-2 hours each. The challenge occurred when combining these modules. They were both attempting to apply to the original price instead of applying the tax after the discount. Nobody had solved this exact problem in the contributed module space, so we had to write the custom code. One week and 30+ billable hours later, we had a solution.

Could we have predicted that 10X overage? Yes and no. One of the things I love about Web CMS Frameworks is that they represent 100,000s of hours of open source contributions that we can all download and use for free. That’s amazing! And out of the box, they can deliver a ton of functionality. They are also highly configurable to meet a wide range of use cases, although that is just the beginning of where time/effort starts to ramp up. Eventually, you hit a point where you can’t do something directly from the admin interface and need to start writing custom code. Compared to configuration changes, custom code requires a higher degree of skill and significantly more time. Even then, there is pluggable custom code and built-from-scratch custom code. The latter is where the LOE ramps up even more.

While the following example is using Drupal and Magento, it probably applies equally to WordPress, Joomla, TYPO3, etc. Let’s begin…

eCommerce: The Quick Snapshot

A client wanting eCommerce could span these use cases.

• ~5 Minutes: Paypal Buttons

• ~1 Hour: Out of the box Shopify

• ~10 Hours: Custom Drupal Commerce Kickstart

• ~100 Hours: Custom Drupal Commerce

• ~1,000 Hours: Full-blown Drupal Commerce/Magento Experience w/ERP Integrations

• ~10,000-100,000 AND BEYOND!

Let’s break this down in more detail.

~5 Minutes: Paypal Buttons

The client has 1-2 products with an expectation of selling only a few a month. Simply creating and dropping a Buy Now button and pasting the snippet in a WYSIWYG Editor is enough to get the job done.

~1 Hour: Out of the box Shopify

Here the client may have a dozen products representing a few sales a month and is still looking for something that’s a step up from PayPal Buttons but quick and turnkey.

~10 Hours: Custom Commerce Kickstart

Here the client loves what the Commerce Kickstart distribution provides out the box, but needs a bit of time configuring the right modules to meet the needs of the client. The client is willing to use the default theme across the site.

~100 Hours: Custom Drupal Commerce

This falls into the bucket of a “standard” Drupal Commerce site in the sense that the customer has some reasonable requests that will take additional time and care. Multiple features need to be enabled and tested together to ensure compatibility. A custom site theme needs to be created to match the organization branding guidelines. Some existing content and orders must be migrated over. There may be some off-the-shelf API integrations, such as the ability to sign up for a newsletter or push a lead into a CRM.

~1000 Hours: Full-blown Commerce Experience w/ERP Integrations

This is where things escalate. To be fair, when you’re at this level, there should be an incredible amount of detail about the specific needs of the project to warn you that you are likely to meet/exceed this threshold. However, this is not always the case. I still remember the punch-in-the-gut feeling I had when a customer’s “inventory management” feature was a full-blown ERP integration with real-time inventory management, customer-specific pricing, warehouse allocation management, pick lists, etc. We later learned that over a million dollars was spent over several years and it took a full-time developer to maintain and operate it.

~10,000+ AND BEYOND!

Piggybacking off the last example, there was one situation where a client was trying to effectively replace their ERP with Drupal without an API integration. Even standing up a ad-hoc API would have cost an obscene amount of money and the retooling costs across 100 end-users made this project dead on arrival. Ultimately, Drupal was not the right approach here, and trying to do otherwise would have cost north of a million dollars. The project ended early before we ultimately spent the time and budget it would have taken.

How to Blow a Website Budget

Earlier I claimed that a single 10X feature could be enough to derail the entire project. Here’s a simple calculation to demonstrate this. Suppose you had a site that had 10 key features each requiring about 10 hours of time for a total of 100 hours. If one of those features goes 10X, you’ve effectively doubled your budget because 9*10 + 100 = 190, which is approximately 2X the original budget of 100.

Can’t happen? In each of the smell tests below, I have at least one project example where a single feature caused a 50% to 100% increase in the overall budget. Thankfully, some of those were not losses to the company because we had to have some difficult but productive conversations with our clients. Still, we weren’t always so lucky, and we sometimes had to eat the loss.

Smell Tests for Website Customizations

When you see these words or phrases in an RFP, you are potentially pushing deep into customization territory.

• “API”: While some services connect with WordPress and Drupal out of the box (Google Analytics is a popular plugin that can just drop in), many are non-standard, and ANY deviation from standard behavior can be problematic.

• Integrations: Anytime you need to connect with additional systems, particularly those that are using completely different technology stacks altogether with no known or publicly documented API, you are likely going to spend several hours/days/weeks just getting a proof of concept going.

• Extensive Requirements: If a client goes into a page of detail for a single feature, chances are there are strict requirements as well as data not yet surfaced. I encourage to try and simplify if the client is willing and able to make said simplifications but beware if they come back and expanded.

• Migrations: Sites involving only 5-10 pages of content are trivial to migrate. Sites that have 1,000s of records across multiple content types with multiple fields and quickly absorb a ton of time setting up the proper translations. Additionally, you may have dirty or incomplete data that needs to be filtered and processes to be compatible with the new data model.

• Products: In the simplest case, all products have a title, SKU, image, description, and price. Ultimately, products can become way more complicated than this and have dozens if not 100+ metadata fields per type.

• Mobile Apps: While CMSes like Drupal 8 exposes REST APIs to provide a means to communicate with other applications and devices, the second you add a non-trivial mobile app on top of a web app you are already adding a decent amount of complexity.

• Features with Known Complexity: Most modern CMSes can provide internationalization and Localization, but edge cases can make things tricky (e.g., swapping out image assets to provide language-specific versions).

The Key: Ongoing Evolution of Estimates and Expectations

Given the impossibility of perfection, how does one move forward with any project knowing that you could hit a landmine at any time? Yes, developing a spidey sense on how to detect and avoid these will serve you well, but you will never catch all of them. The key is to set expectations in the beginning that you will iterate through the estimates at each stage of the project, further refining them with the additional information you’ve gleaned. Ideally, you’ve at least sized each feature to the right level of magnitude, and you can hone in the last 10-30% before your 20% through the project.

For more details on how to do this, be sure to check out my Drupalcon Nashville talk (or the recording if you can’t make it).

Photo by Helloquence on Unsplash

As a subscriber to the Startup CXO Playbook, you will be the first to know when it’s getting closer to a release date (I hope to have all edits done within 2 months). At that point, I would love to get an advanced copy into a few hands for feedback. If you would like to be part of that, please hit reply and let me know.

As for this newsletter…

Now that I’m through the arduous 1st draft, I’ll return to posting here approximately 2 times a month. However, my main focus will be on getting all the finishing touches in order to get this book polished and out the door.

Many thanks for your continued time and attention.

Let’s say your new software startup needs 100 customers to break even.

• Want 100 paying users? Then you need 1,000 free users.

• Want 1,000 free users? Then you need the attention of 10,000 people.

I can already feel you laughing at me.

“Oh, Rick. That’s crazy! My product will be SO awesome that I’ll only need to show it to 100 people. And even if ONLY half of them buy it, they’ll love it so much they’ll tell at least two friends. I’ll be at 100 customers in no time!”

Tragically, I’ve seen an alternative version of this story dozens of times.

• Steve has an idea.

• Steve believes 50% of those who see it will buy it.

• Steve empties his 401K for funding.

• Steve gets an LLC, an office, and starts his new venture.

• All the money goes into building the product.

• The big launch day occurs! Celebration!

• Steve tells everyone he knows, but…

• Less than 1% convert.

• Steve fiddles with the price point over and over.

• The conversion rate barely moves.

• Steve runs out of money, can’t continue, and abandons his idea.

True story

Steve (not his real name) was adamant his new app would sell 10,000+ subscriptions at launch. We sent an email to his list of 25k people, and waited eagerly to see how well the $10/month price point performed.

Less than 250 people subscribed. Oof.

We tried fiddling with the price for months, thinking that was the objection. Should we charge $8/month? What if we offered $50/year?

Unfortunately, all this price-point tweaking did little to change the number of paid members. Months later, the number of paid members spiked to 500, but kept returning to 250.

Not good.

The company was losing money and needed to validate that there was enough demand to continue.

So we sent a Hail Mary offer to the email list and offered a free 6-month trial (no credit card required). Surely, this would open up the floodgates!

Only 1,000 free trials kicked off (oof). Worse, 90% of these free trials stopped using the service within 1 week (double oof).

We didn’t we a price problem. We had a product problem.

People weren’t using the app, even when we gave it away for free.

Spoiler alert. There are times when this is a solvable problem, and other times when it isn’t. Sometimes a product just doesn’t have a market.

The latter can be a tough pill to swallow, but it’s better to acknowledge.

The “Happy Ending?”

After a 2-year grind we changed the product until it hit resonance. We ended up selling 2,500 subscriptions in a month and the business went from bankrupt to sustainable. From there, we knew that to grow the subscriptions we had to widen our funnel. For every 10K social media followers, we could expect another 1,000 free users and another 100 paid users. That’s why this exercise is so valuable to determine for your own product or service.

If You Gave It Away For Free, Would They Use It?

Given credit where it’s due, the exact phrasing of this question crossed my Twitter feed a few weeks ago. Thanks, Jen Abel!

https://twitter.com/jjen_abel/status/1643319202462289923

This is a powerful question to ask to gut-check yourself when starting your go-to-market strategy. Of course, getting revenue is important, but verifying that a person even wants the product or service is critical.

Conversion rates vary widely, but I always start with 10% to get your mental model going. Start with what you need and work backward.

• Need 100 paying customers? Then you need 10X the number of free users.

• Need 1,000 free users? Then you need 10X that as social media followers.

And if those numbers are unreachable, you must focus very hard on testing and validating your conversion rates. Maybe your product is so fantastic that you actually do hit 50%. Realistically, you’ll be at 5% or 1% out of the gates. But test early and often, and don’t bullshit yourself about how easy the first sales will be. They won’t be unless you happen to strike gold.

eBay is for customers that value money more than time.

Amazon is for customers that value time more than money.

On eBay, you may find dozens of matches for the product you're looking for, but then you have decisions to make. Do you trust the vendor with only a few ratings? Do you trust the one with 4 out of 5 stars? Can you wait up to a week for shipping?

On Amazon, you may pay a much higher price. However, you don't need to spend 10-100x the time in the decision-making process. With Amazon, you are 2 clicks and 10 seconds away from same-day delivery. And you get the confidence of a bulletproof return policy.

Now let's flip this around.

What are YOUR customers like?

Do they treat you like an eBay vendor? Are they shopping around to 10 different places, haggling to try to get the absolute best deal?

Do they treat you like Amazon.com? Are they ready to find the top result, quickly scroll to verify it all checks out, then 1-click buy regardless of the price?

I've worked with both in my life.

The eBay client wants detailed breakdowns of all hours worked for each invoice. Then they want to debate (on your dime and time) specific line items just to see you sweat. You (eventually) capitulate and remove a few hours after they made a veiled threat to try a competitor.

Now the Amazon client can be equally picky but in a different way. $5K to 10K a month retainer? No problem! But you better save them at least 2 to 10X that a month. If you don't, they'll quickly find someone else who can deliver results quickly and consistently.

In my experience, it's a no-brainer to optimize for the Amazon customer. They have and are willing to spend the money if you can deliver the results.

So it's worth asking again.

What customer type do you have?

Which type do you want?

Malcolm Gladwell popularized the “it takes 10,000 hours to achieve mastery” meme in his book Outliers: The Story of Success. The lesser-known follow-up claim was that the right mentor could reduce those hours by 1/3. That’s a massive amount of time! 3,333 hours is equal to 80 40-hour weeks. And yet, most people are unwilling to invest the time or the money to work with a mentor/coach for 2-3 hours/month.

Or what about this claim?

Startup accelerators like Y-combinator or Techstars promise to get your business 1-year further in 12 weeks. That’s 40 weeks saved! Now those 12 weeks might be the most stressful, intense weeks of your career. You’ll be immersed with dozens of mentors, advisors, investors, and other startup founders. It’ll be like drinking from the fire hose, which will level you up pretty damn quickly.

Of course, there is an alternative. You can always figure it out yourself.

You can find all the books and blog articles on the topic to gain knowledge. You can then try assimilating the pieces that matter the most to you. You can then take action, gauge the results, and iterate. You may stumble upon something novel and powerful that nobody has ever seen.

Or you could just be reinventing the wheel.

This is one of the reasons I love to mentor startup founders. They may grapple with difficult challenges for weeks without a clear way forward. Fortunately, I may have hit upon this same problem 2-3 times and tried 2-10 things that didn’t work and 2-3 things that did.

It doesn’t always happen, but it happens more often than not.

And when it does happen, hours/days/weeks are reclaimed to tackle the next problem and then the next.

Is this something of interest to you?

If I’m not a match, I know many startup CTOs and CXOs I can refer you to. At the very least, I would love to know your big hairy problems and whether I might already have some ideas on how you can take it on.

Everyone struggles with some level of procrastination. We say, "I'll get to it tomorrow" and "when I find the time." Or the most nebulous of all... "maybe someday."

But what if circumstances change? What if we have no choice but to act?

Moving is a pain in the ass, but not if you discover your house is perched on a foundation that is about to experience a landslide.

And what if tomorrow isn't guaranteed? What if you're diagnosed with a terminal illness and have days instead of decades?

10 years ago, I heard a quote that I can't get out of my head. It was a statement by Joel Roberts as he addressed a room full of entrepreneurs looking to take their businesses to the next level. The question was, what do you do "when the stakes are high, and the moment is brief."

Mic drop.

The stakes are always high because we've been given this miracle we call life. No matter how bad our current situation or how unfair life may have been, we live on this statistical improbability called Earth. We live at the pinnacle of our creation or evolution (whichever you believe). We live in a time of infinity, where virtually anyone reading this article can access the internet and, therefore, learn any new skill or start any new career. The stakes are high because we can fulfill our potential to the degree we want and live a great story.

The moment is brief because we have one life. ONE LIFE. And while the average lifespan maybe 80 years old, any one of us may die tomorrow. 

The business that we started may have X months of financial runway, but X months will blink by and become tomorrow. Will we have achieved our goals, or will we have pissed the time away?

The projects and dreams we wish to start "someday" will soon become the regrets of yesterday. Are we willing to live our tomorrows in that regret?

I have many regrets, most of them because I'm overly ambitious. No. That's a cop-out. The reality is that I acted like I had all the time in the world and pretended like the goal wasn't enticing enough to take action. The fact is that neither was true. 

The stakes of life are high, and our moment on Earth is brief. 

This is why that quote rings in my ears and why I've developed a bias toward action. Netflix will always be waiting for me when I can no longer get out of my chair. But, even then, there is still so much to experience in one's final days... if you have something that moves you.

Where are you holding back when you need to act now?

Tick tock.

I say this a few times a week, and it stings each time.

Why?

Because sometimes, it’s true, and I made choices that overloaded me.

Because sometimes, it’s false, and I’m procrastinating out of fear.

Either way, I know it’s my responsibility for how I got there AND why I’m staying there. I both HAVE the time and can MAKE the time if I have the courage to make new choices and take new actions.

This is why courage compresses time, and fear expands it.

## The Cost of Fear and Resistance

When we are afraid, we procrastinate, avoid, and deliberate. We say yes when we should say no. We hedge our bets by having plans A, B, C, and D versus putting as much energy into plan A. We take hours to work up the nerve to ask the prospect of the business. We spend days writing a press release that should have taken 30 minutes.

When courage trumps fear, we slice out the superfluous shit.

All of a sudden, people start noticing.

More leads get called, and more deals get closed.

More content gets generated on a consistent basis.

More emails get discarded while the important ones get addressed.

More time is created, resulting in more success at completing things, which creates more confidence. This becomes a virtuous cycle.

## Courage is Critical When Time and Energy Are Limited

I’m no longer the 20-something college kid that can whip out 80-hour weeks or multiple all-nighters. I have created a life where I need to finish my startup work in sub-50 hours/week to have time for my family and myself.

As such, I don’t have the luxury of wasting time during the work week. I know this. And still, I can find myself spinning when fear or resistance hijacks my thinking.

The trick for me is awareness. When I find myself swirling, I identify it and reset it. I recognize that I’m pissing time away, distracting myself with secondary and tertiary tasks when the 1-2 critical things need my full attention now. And by now, I mean right now. Not when I have days of uninterrupted time (which never happens). But what can I do right now?

Courage compresses time. It may not always end pretty. Sometimes taking a leap without all the necessary research can blow up in your face. However, the few times this happens are far outweighed by the gains of moving everything else along more quickly.

What about you?

What big decision or action have you been sitting on for days, weeks, months, or years? Can you make a decision right now? Can you take action right now?

Or will you find yourself saying (again) “I don’t have the time.”

The choice is yours.

Time is ticking.

Long before no-code solutions like Webflow went from a neat demo in 2015 to a 4 billion dollar company in 2022, I was in a meeting with one of its early power users. Let's call him Zack.

Zack scheduled a meeting with me and showed off a new way of building websites. After the presentation, I admitted that it was intriguing. However, it would completely change how we ran our business, and it felt like too much risk without a clear return on investment. So I said that I wasn't interested.

Zack got hostile. "Are you stupid? Don't you see this is the future? Are you willing to ignore this and put your company out of business?" Technically, he was right... eventually. 7 years later, I recommended a Webflow competitor (Bubble.io) to a Techstars startup. In less than 10 weeks, they used the platform to build an MVP that they used to raise over $4M.

Not bad! It was indeed the future of website development.

Unfortunately, Zack and his I-know-better tactics were off-putting to me. He continued to badger me over email until I told him to pound sand. What a bummer. My career path would have benefitted me by keeping up with the no-code industry. However, I wasn't willing to follow a condescending asshole, so I kept plugging along as usual.

And so it goes for many misunderstood geniuses out there.

Product Market Fit Requires Being Understood

Some are legitimate geniuses who can't translate their vision in a way others can understand. I knew dozens of people at MIT with off-the-chart IQs that couldn't explain-it-like-I'm-five (ELI5) to the layman. As a result, they struggled to get others to see what they could see... to buy into their vision of the future.

Achieving product-market fit in a startup is already hard enough. But, it's made so much more challenging if you can't tell a compelling story and speak to the problem/opportunity of the customer. Or if you can't help frame your solution in their own words and from their worldview. Or if you can't speak to the customer's most pressing wants/needs/values.

This misunderstood genius eventually becomes frustrated with this communication barrier. Sometimes, they turn this frustration into insults or ineffective coping mechanisms. "If only they could see what I see! But those dumb customers... they just don't get it!"

Meanwhile, people with clear communication of simpler solutions can have a much easier time gaining customers and traction in the market.

Sad Zack

As much as I disliked him, it was sad that Zack didn't capitalize on his grand vision. When I checked his LinkedIn profile a few years ago, I saw that his business ended before Webflow rocketed to its unicorn status. It's a shame. He was intelligent but early. He was right but repellant. He was correct but confusing.

Now, a bit of humility.

Sometimes, I'm like Zack. Sometimes I think something is clear as hell, and I fail miserably at creating an effective metaphor or using the right example to land a customer. I can see the confusion in their eyes, but I'm flailing at finding the right words. Sometimes I get frustrated (for a moment) that they can’t see what I see.

The difference is whether or not you blame them for not understanding or take ownership for not being unable to help them get to a place of understanding. Huge difference. The former will stall your progress. The latter will help you achieve resonance on the journey to product-market fit.

The idea was great but a hard sell 20 years ago. The devices were expensive, the accuracy wasn't perfect, and not everyone loved the idea (yet). This was years before the release of the iPhone.

Zach and his co-founder were also "young," which made pitching investors, businesses, and clubhouses challenging. They could feel the objections. "They are just kids. What do they know about running a business? How can we trust this will work?"

For sure, this was ageist. Still, it was a barrier to overcome.

Hiring Token Adults

One bit of advice Zach received was to hire a more seasoned executive on the team. Ideally, (and I wish I was joking) someone with some "graying hairs" with a solid 20+ years in the industry. This person's fundamental value proposition was attending meetings as the token adult.

Isn't that ridiculous?

As a 5x startup founder and Techstars mentor, I talk to many first-time founders. Unfortunately, most struggle with balancing optimism (which you need to be to start a startup) with delusion (which can lead to SBF-like disasters).

The result?

Zach's adult-in-the-room addressed a fundamental concern of their audience. "Well, this older guy looked at the business model and didn't quit. So it must be somewhat legit. What could go wrong?"

What Could Go Wrong?

Turns out a lot.

When Terra collapsed (spectacularly) in under 24 hours in 2022, many were baffled. But Mike Novogratz is a serious VC and went as far as getting a tattoo on his fucking arm. How could he not have done due diligence?!

But it wasn't just Luna.

FTX. Celcius. 3AC. BlockFi. Terra.

All lost billions of dollars and had adults in the room as investors or operators.

The point is that having adults in the room won't guarantee success or integrity. Fraud can be perpetuated by anyone at any age. Flops can happen even for people with an excellent track record.

And someone in their 40s or 50s can become so blinded by their greed or ego that it can hijack their ability to think clearly. They can also create a reality distortion bubble around them, duping otherwise intelligent people into going along for the ride (before going over a cliff). Hell, SBF took out Tom Brady and Shark Tank’s Mr. Wonderful. Anyone can be pulled under if they aren’t doing proper due diligence.

Bottom Line

So, sure, a seasoned pro can bring a lot to the table and help shore up trust in a way that a first-timer cannot. However, silver hair isn't a silver bullet. While age may and experience can be used as proxy for intelligence, experience, or probability of success, it can also blow up in your face if you trust it too much.

Back? Good.

So now we need to get started, build momentum, and reap the benefits.

I encourage you to refrain from following these lists verbatim. Experiment with them. Figure out what works for you, and discard the rest. Make it your own. 

I'll finish with the exact format I use at my current company, which you can use as a template. But first, let's begin with the end in mind.

My 1x1 Wishlist

Suppose YOU were on the receiving end of a 1x1. What would the best possible outcomes be?

• I have clear targets on what success looks like.

• I'm set up with a clear path to winning.

• They understand my larger career objectives and, when possible, align my work responsibilities against those goals.

• I feel heard and understood.

• I feel safe and supported.

• I have the opportunity to ask hard questions.

• If I get feedback that stings, we can talk it through.

• I can surface issues.

• I can propose ideas.

• I feel appreciated and connected.

• We don't just make empty promises, but we revisit our previous commitments.

• We admit if we fucked up, but forgive (as long as this isn't an unfixable pattern) and figure it out.

• We re-align if day-to-day work doesn't match our key objectives.

• I feel like they have my back.

• I feel like they are genuine human beings.

• I can trust them, and they can trust me.

And so on.

Yes, this is an extensive wish list, and no, you can't nail all of these in a single 30-minute meeting. However, you can make progress towards a handful of them each time.

Strategies and Tactics

• Rapport: It can't all be about business. The other person needs to feel a connection, which isn't always easy. Besides small talk, you can use ice-breakers like "Ask Deep Questions" to create novelty and surprise in the conversation. Heck, you may find out you both have a secret passion for 80s arcade games or baking artisan bread.

• Running 1x1 Document: I use a private 1x1 Google document for each direct report. It should go without saying, but this file MUST be confidential and never opened up to anyone. Break this rule, and trust is shattered. The benefits of this document include the following:

  • Capture: It's not always appropriate to address issues as they happen. Having a place to capture them between meetings ensures they don't get swept under the rug.

  • Accountability: If decisions and commitments are made at previous 1x1s, they should be reviewed upfront to ensure progress was made. Otherwise, trust in the process is eroded. Say what you'll do; do what you say.

  • Evidence of Progress: In the day-to-day hustle, it can be easy to lose perspective regarding how much time has passed between topics. This 1x1 document can help anchor these milestones over more extended periods.

• Checks: Similar to ice-breaker questions, it's possible to have a set of recurring prompts to surface any issues across various factors. Examples:

  • Clear Target? On a scale of 0 to 10, how certain are you that you know the highest and best activities you could work on? How can we increase that 1 unit higher?

  • Flowstate: Are you feeling in the zone on the Challenge/Skills balance? Bored? Stressed? How can we pull you back into the sweet spot? 

  • Team Check: On a scale of 0 to 10, how well is your team hitting its targets? How could you (be specific) help make that 1 unit higher?

  • Leadership Check: How are your direct reports doing on a scale of 0 to 10? Are there any challenge areas that need to be addressed?

  • Company Check: How's your overall sentiment of the company and your position within it?

• Feedback: In the checks above, we mainly focused on the direct report and wanted to hear from them and draw out wins and challenges. Here we flip that around.

  • Conversation for Commitment: Surface any new/updated needs from the direct report. Once there is mutual clarity on the ask, ensure an explicit ask for commitment and a clear agreement. If something else has to be negotiated to take on that new commitment, do this now.

  • Conversation for Complaint: If a previous commitment was made, but isn't being met, revisit. Drill down any factors that can be contributing to it and figure out a way around them. Once again, get mutual clarity and an explicit ask for commitment.

Again, this is a lot to cover in a single conversation. You may get stopped anywhere along the way and may need to take the rest of the session to address that one thing. That's ok! If both sides are doing the work and holding themselves accountable, there may be fewer and fewer things to discuss in future conversations. Many of these items become optional or a simple gut check.

However, it's better to linger on one part to resolution than to just bulldoze through the list.

My Current 1x1 Template

So what do I do?

In my current role, I use the following agenda:

• Unstructured chat time to catch up (10 minutes max).

• Ask if anything is missing from their conversation capture list.

• Review any commitments from the last conversations.

• Checks:

  • Targets check-in

  • Flow state check-in

  • Company check-in

• Any burning comments, questions, ideas, or needs?

• Feedback: Any new asks or areas to address.

Ultimately, you want to grease the wheels to get the conversation started and only rely on the prompts when you feel things stalling, OR you want to be comprehensive / not gloss things over.

Do this every 2-6 weeks for a few months/quarters, and you should start to experience the ROIs discussed in part 1.

Questions? Let me know!

1. Direction: Do we agree on WHAT to build?

2. Distance: Do we agree on WHEN what’s built achieves the goal?

Lack of clarity on either can lead to miscommunication and frustration.

In part 1, we explored distance (i.e., WHEN). Is software considered done WHEN you get it to work the first time? When can someone else repeat it? When it’s in production use? When it’s stable and bug-free? When it’s delivering value to the customer? How far do we need to go until done means done?

When have I made the point? Hopefully, by now!

Let’s address the other dimension: direction.

This challenge crops up all day, every day, in software development.

A classic example: a hard-working employee spends days, weeks, or months delivering a solution to the wrong problem.

Big oops.

The costs of this mistake can be considerable ($10K to $100K or more). Not only did you lose every billable hour from this employee, but the opportunity costs and timeline delays of a feature, project, or product launch can be a killer.

The solution is simple, yet often skipped over. First, we need everyone to be on the same page on the target.

Agile Development popularized the concept of “Acceptance Criteria.” Typically, this is the laundry list of things the software must do to be considered testable and complete. For example, an e-commerce feature might be described this way.

• Users can add a product to their cart.

• Users can update the quantity of a product in the cart.

• Users can remove an item from the cart.

• Any changes to the cart must check against available inventory.

• If quantity isn’t available, send an error message and reduce inventory.

To its credit, this is a powerful approach to use, particularly for backend software without any front-end user interface.

However, there’s another approach I like better. Brene Brown uses the term “painting done,” which is an exercise that two or more people do to describe the target TOGETHER. The together part is key because the acceptance criteria strategy often results in a list just being handed to a developer. In painting done, the focus is on a discussion until both sides can repeat each other with shared clarity.

An example might go like this.

• Person 1: “I’d like to sell my books on my website.”

• Person 2: “Excellent! Let’s paint done together. I’m assuming you want the books to appear with the title, subtitle, picture, price, and checkout button. Correct?

• Person 1: “Yes, exactly! Let’s do it.”

• Person 2: “Not so fast! Do you want a full eCommerce backend so they can purchase and pay directly on the site? Or can we just link to Amazon?”

• Person 1: “Oh, to hell with Amazon. I want them on my website!”

• Person 2: “Ok, great! So there we have two options. We can install a dozen or so plugins and configure them within the backend. This full-blown integration would take 50+ hours, but it’ll look seamless. Or we can set up a Shopify subdomain and have it ready and configured in 5 hours.”

• Person 1: “Oh, that 1st option is expensive. Let’s just use Shopify.”

In this example, the request to sell on a website had three viable options:

1. Full e-commerce integration.

2. Redirect to an ecommerce platform like Shopify.

3. Direct link to Amazon.com.

By not attempting to mind read from the initial request, a few minutes of back-and-forth conversation zeroed in on the correct direction. They can now get into the nitty-gritty details.

With this decision, the developers and designers have a (more explicit) target and, as a result, a better shot at winning. Next, they can decide how far the Shopify configuration needs to go before its considered complete:

• Just get it up and running with a default theme?

• With complete branding?

• With promo codes?

• With sales tax calculations?

• With fulfillment workflows?

• With the migration of existing customer records?

Now we can shore up these remaining bits into acceptance criteria. Once complete, we have a more robust definition of victory. And by making this clear up front, the team has dramatically increased its odds of success.

Lack of clarity can be a killer. This is where “somebody-itis” rears its ugly head.

* “Somebody should take notes.”

* “Somebody should follow up with that client.”

* “Somebody should address this emergency.”

And the all-time favorite of ambiguity.

“Somebody should do something.”

BUT! Like /The Tragedy of the Commons/, “somebody” often means “nobody,” and no things get done.

The key to curing somebody-itis is never letting the conversation end without naming a specific somebody.

* “Who (specifically) will take the notes?”

* “Who (exactly) will follow up with the client?”

* “Who needs to drop everything and deal with this emergency?”

And regarding someone doing something, let’s define what that something is, not in abstract terms, but in clear, concrete terms.

Left uncured, somebody-itis is a killer.

You lose clients. You lose colleagues. People are frustrated, but they can only point fingers at some abstract “somebody.”