Becoming an Expert Generalist

Becoming an Expert Generalist

In her post Stop Pitching, Start Storytelling, Sunflower Fund’s GP Sydney Fulkerson, wrote:

Contrary to popular opinion, pitch decks don’t raise money.

Founders do.

Though true, what is a founder without his/her team?

What is a startup sans those myriad designers, engineers, operators, and more that not only construct the trains, but also ensure they both stay on their tracks and run on time?

This cast of characters brings a startup’s story to life.

It’s a tale — pun intended — as old as time: Every Zuck needs a Sheryl Sandberg, every Don Quixote a Sancho Panza, every Batman a Robin.

Put simply, a story is nothing without its characters.

That said, who should an entrepreneur recruit to help write the chapters of his/her entrepreneurial journey?

How does he/she determine the right people to implement the processes that create groundbreaking products?

That trillion-dollar question is a bit above our budget (now, that is!), however, every single team needs a utility player: the expert generalist.

Expert generalists are the mortar to a startup’s bricks: they’re ubiquitous, fit every crack and crevice, and help to hold the entire business together. As David Epstein wrote in his book Range: Why Generalists Triumph in a Specialized World:

The challenge we all face is how to maintain the benefits of breadth, diverse experience, interdisciplinary thinking, and delayed concentration in a world that increasingly incentivizes, even demands, hyperspecialization…[Ironically, o]ur greatest strength is the exact opposite of narrow specialization. It is the ability to integrate broadly…

Successful problem solvers are more able to determine the deep structure of a problem before they proceed to match a strategy to it.

But how does one tune into signal in a world inundated with noise?

How does one deftly delve into the macroscopic and microscopic — ensuring enormous progress via small steps?

Put simply, how does one become the elusive expert generalist?

Well, it takes one to know one. That’s why we asked expert generalist Nick DeWilde.

Co-founder of a stealth startup in the talent development space, co-founding faculty member at Invisible College, and author of career strategy newsletter, the Jungle Gym, Nick is a skilled operator and one of the best thinkers this author has ever met. Below he generously shares six traits he uses to distinguish expert generalists from novices.

Over to Nick!

What Distinguishes an Expert from a Novice?

For most professions, expertise gets defined through the skill maps, competency frameworks, and leveling matrices that HR departments use to make their workforces legible. But what about the generalists who operate outside these systems?

Having worked with plenty of generalists and embraced the career path for myself, I’ve settled on six traits that distinguish expert generalists from novices. In this post, I’ll explain what they are and how you can cultivate them for yourself.

Trait #1: Delivering Day-One Value

A product’s magic moment happens when its users get their first substantial hit of value. Often this moment solves a problem, provides delight, and motivates users to stick with the product.

Working relationships also have magic moments.

As a generalist, your value proposition to potential collaborators is often a bit murky. Since you aren’t an engineer or a salesperson, people naturally want to know how you will make their lives easier. Expert generalists are able to answer that question quickly by adding what I call “Day-One Value.”

Day-One Value means that you quickly provide enough value so that your collaborators experience “the magic moment of working with you.”

How you create this value will depend on your unique set of skills. For example, if I’m advising a founder, my Day-One Value might come in the form of an insight that relates to their go-to-market strategy. If I’m doing consulting work, it could be actionable changes to their sales narrative or a nicely-designed piece of marketing collateral. When there isn’t something obvious, a helpful introduction often does the trick.

While your magic moment doesn’t need to be delivered on day one, it’s useful to have this goal as it sets the tone for your working relationships.

Trait #2: Developing Quick Context

To deliver value quickly, you need a tried-and-true way of gathering quick context on new situations. This skill is more complicated than it seems. It requires:

  • Knowing what information you need
  • Asking reliable questions that will elicit the information
  • Building rapport and trust, so people feel comfortable divulging the info you’re seeking
  • Developing a framework to make sense of what you’ve learned
  • Honing the process, you use to synthesize and articulate your learnings so you can validate them with others

Despite what some people say, these skills can be taught and learned, but they also need to be practiced a great deal if you want to use them in real life.

Trait #3: Self Awareness

It’s perfectly reasonable to take on responsibilities that are outside your comfort zone. But, if you don’t have the self-awareness to understand how you operate, you are likely setting yourself up for failure.

In practice, self-awareness can help you set expectations with stakeholders and structure your time appropriately to match the demands of your work.

Unfortunately, self-awareness is hard to develop on your own. Cultivating it often requires getting a lot of feedback from managers and colleagues or, better yet, 1:1 coaching so you can learn to see yourself as others do.

Trait #4: A Get-Smart Playbook

Every expert generalist needs to have a battle-tested playbook for getting smart in new domains. My personal Get-Smart Playbook has three pillars:

  1. High-quality Information Diet
  2. Reliable Research Habits
  3. Robust Expert Network

I’ll quickly dive into each:

High-quality Information Diet

Your ideas are a product of the information you consume. Improving your outputs requires actively directing your attention to high-quality information streams and diverting attention from low-quality ones.

The tricky thing is that our information ecosystem is full of talented marketers who masquerade as experts with convincing copywriting techniques. While we’ve gotten good at spotting click-bait blog posts from Buzzfeed, we still fall for people with big Twitter audiences who know how to write threads that game the algorithm for engagement.

Cultivating a quality information diet requires consciously selecting the domains that are essential for your work and seeking sources that can keep you informed about those topics.

Reliable Research Habits

You can’t always expect useful information to flow your way serendipitously. Often, you’ll need to quickly get up to speed on new topics through a structured research process.

That means you need a better research process than just plugging queries into Google and praying that you surface a decent piece of content marketing.

Strong researchers know that there is scholarly research that touches upon almost every topic. The key to uncovering these hidden gems is to construct a strong-enough foundation of knowledge so that you can identify the right terms to plug into Wikipedia, Amazon, or Google Scholar to gather the sources that will actually help you get smart on a new topic.

Expert Network

The answers to your most important questions can rarely be found via Google. Instead, these answers reside in the minds of experts with years of experience putting theories to the test. In order to become an expert generalist, you’ll need a strong network of specialists and the ability to convince them to share their hard-won wisdom with you.

Further Reading:

Trait #5: Clear, Multi-Modal Communication

Ultimately, it doesn’t matter how great your ideas are if you can’t communicate them clearly.

In our increasingly-asynchronous paradigm of remote/hybrid work, clear communication is only becoming more important. Expert generalists should be able to articulate their ideas via multiple modes of communication:

  • Speech (Zoom meetings & Loom videos)
  • Writing (Email, Google Docs, & Slack Messages)
  • Design (Presentations & Figma files)

Mastering clarity requires understanding how to construct a logical argument and share a narrative that will make your ideas stick.

Trait #6: Stellar Execution Habits

In any working engagement, there are moments when you need to stop strategizing and start shipping. These are moments where the expert generalist can leverage their experience to play at a higher level. The best generalists I’ve worked with tend to have well-honed execution habits like:

  • Task management to keep track of all things they need to do.
  • Time management to work on those tasks at moments when they will be set up for success.
  • Energy management to ensure they’ll have enough energy to complete the work for which they have made time.

While this isn’t a comprehensive list of what makes an expert generalist, I think it hits on six of the most critical traits to cultivate for those who are playing the generalist long game.

Nota Bene: The above was originally published here. It has been lightly edited for clarity, Stonkyness, and vibes.

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