What is a Wildcard Person?

You've Probably Met One

You know that person on your team who seems to be good at everything? I mean the literal definition of the word good. Not master. Good.

When a problem comes up that nobody else has any experience with, this person volunteers to jump in head-first.

They don't produce masterpieces, but that was never the intention. The intention was for the problem to be solved, which it now is.

They are masters of producing minimum viable solutions in a diverse array of subjects. Some of these solutions never need to be replaced. The rest are viable until a full-time dedicated specialist is required.

Their job titles bear no resemblance to what they actually do on a daily basis, which also makes them hard to find and describe. I like Andreas Klinger's description of "Chief WTF Officer".

They're usually a "Product Manager", "Full-Stack Engineer", "Head of Growth", or similar. Sometimes their official titles are hilariously out-dated, but everyone knows what they do, so it doesn't matter.

A friend called them "Wildcards", and I think that's a perfect label.

Wildcard — a card that can have any value, suit, color, or other property in a game, at the discretion of the player holding it.

Instead of a card in a game, think about a person in a startup.

A Wildcard is a person who can take on many different roles as needed. They are fundamentally problem solvers who enjoy tackling new challenges. A Wildcard's role at any given time is dictated by the problem that needs solving.

These people thrive in early stage startups, and not all have the desire to be CEO. Most just enjoy the challenge of doing new stuff.

The Strengths of Wildcards

Wildcards are highly valuable because of how quickly they can fill in the gaps in times of uncertainty.

Some examples of Wildcard behavior:

• Need to run Facebook ads? They'll figure it out.
• Product video required for a presentation? It will be done by Thursday.
• Blog post needs editing? Yep.
• Landing page doesn't work on mobile? Give them a few days.
• Subject-matter expert required? They'll find one today.
• Don't have a customer success person yet? Now you do.
• Scrambling with a broken demo, 2 hours before a conference starts? They'll get it working.
• Need a vector version of your logo? Done.
• Massive bug in your app dashboard? They'll figure it out.

Not all Wildcards are the same. They tend to have a large cluster of skills rather than a linear set, but the content of each cluster is different for each of them.

Example: a Wildcard joins a startup as a "full-stack engineer". Their best skills are in web development, but they also know how to write quality copy, use digital marketing tools, wield Figma, edit videos, create 3D renders, grow social media accounts, and optimize SEO. As the startup grows and these problems arise, this "full stack engineer" solves them in quick succession.

This Wildcard spends equal parts of their time on programming, design/UX, writing copy, configuring an arsenal of marketing tech, and making sure the startup is found on Google. They even volunteer to attend the tradeshow and do a great job demoing the product.

Is "full-stack engineer" an accurate description of this person? If not, what would you call them? How would you find them in the first place?

Beyond the inherent productivity advantage a Wildcard can offer, there is a cohesiveness in their connect-the-dots nature. The startup will enjoy a unique advantage in having an engineer capable of building an app, writing landing page copy, creating the demo video, and pitching it to customers.

The Drawbacks of Wildcards

"A multi-tool can do many different things, but not all at the same time."

Wildcards do not have unlimited time or energy. If the full-stack engineer example from above is tasked with leading customer demos for a week, that's a week not spent programming.

This is logical, but is not always considered. Managers should not be dismayed when their multi-talented full-stack engineer solves a critical emergency but doesn't finish their other assigned work that day.

Furthermore, Wildcards thrive with new tasks and suffer from repetitive ones. They also have a hard time staying outwardly organized.

If your Wildcard is a Product Manager, their team will ship feature-complete products on time, but without the neatly organized armada of JIRA tickets or burn-down charts you wished to see. The friction of keeping things organized is less stimulating than the instant feedback of just doing the work.

Wildcards often get so focused in on a current problem that they forget about other, low-priority work somewhere else in their queue. They tend to prioritize the most recently assigned task first, so keep that in mind.

They also aren't the right people to maintain things over time. Expecting "hygiene tasks" like test suites, expansive documentation, or neatly organized design docs to be maintained while a Wildcard is simultaneously fighting fires will leave both of you frustrated.

Wildcards thrive doing new things. They also don't have unlimited energy.

Creating a new documentation portal for your startup's API is a good task for a Wildcard. Maintaining it for the next 18 months is not. If you want a maintainer, hire a maintainer, not a Wildcard.

"Tell me why this needs to be done now, then get out of my way and let me do it."

Wildcards require a sensible level of urgency, logical prioritization, clear feedback, and a generous amount of flexibility.

That's why they fit best in startups.

Wildcards in Summary

Wildcards flourish by taking on unknown challenges rather than known routines.

Wildcards thrive with fast-paced, high-value work. They have a large constellation of skills instead of one specific direction of mastery.

Wildcards perform best in the chaos of the hunt and suffer in the monotony of the repetitive. Giving them a single, permanent job function is a waste of their talents.

Wildcards are poorly described by job titles. They are creators, firefighters, and problem solvers. They are not specialized tools.

Wildcards tend to be labelled as "Swiss army knife", "generalist", or "jack of all trades". Each term fails to describe the full range of value that a Wildcard brings to the table.

Wildcards fit best into the chaotic nature of early-stage startups.

Wildcards get shit done.

How Wildcards Thrive:

• jumping head-first into things they've never done before
• venturing into unknown territory
• creating, building, designing, making, upgrading
• solving problems, fighting fires
• connecting dots between diverse subjects
• learning new skills & tools
• automating routine tasks

How Wildcards Suffer:

• repetitive tasks
• low-value work
• micro-management
• strict, multi-step, high friction processes
• unclear expectations
• minimal feedback

What Wildcards Need:

• clear, routine feedback
• appropriate urgency
• flexibility with processes
• explicit rules (and the freedom to break them)
• unambiguous priorities
• bullet points, not essays
• permission to not ask for permission

Want to read more like this? Check out my book on ADHD productivity