Becoming an Expert Generalist

Six traits that distinguish expert generalists from novices

Owen D. Pomery

👋 Welcome to the latest issue of The Jungle Gym – the newsletter that helps you build a more fulfilling career by integrating your work and life.

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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:

• The T-Shaped Information Diet

• How to gain an information edge by asking better questions

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.

Quick shout out to Tom White, who whipped this post into good shape with his brilliant editing. I’ll be syndicating it over at Stonks next week, so keep a look out and give it some ❤️.

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For Your Information Diet

🔎 Understanding the strategic situation – One way to think about a company’s strategic situation is to consider what lies outside of an organization and what lies inside of it. What’s outside tends to constrain what the organization can do and what’s inside represents resources for the company’s work. (Vaughn Tan)

🎁 Dealing with hard feedback – One of my fundamental beliefs about education is that work is the best environment for learning. Because stakes are real at work, everyone tends to be much more motivated to grow and improve than in academic settings. One way this learning takes place is through receiving feedback if you have the emotional tools to handle it. (The Hard Parts of Growth)

💸 Fake life, true wealth – Why do wealthy people keep working, even after they have more money than they could spend in several lifetimes? To retain access to a network of other influential people who will do favors for you because they believe you are in a position of power to do favors for them. (Old Rope)

🤝 Prioritizing “real friends” over “deal friends” – While I like this post, I disagree that “deal friends” need to be prioritized over “real friends.” In reality, a lot of meaningful adult relationships start out transactional. What transforms a transactional relationship into one that feels genuine is that both people build enough trust that they stop keeping score of the transactions. But I do agree that if you find a relationship can’t move beyond the point of transactional, it’s worthwhile to deprioritize. (Petter Attia)

⏰ Your Career Is Just One-Eighth of Your Life – “Work is too big a thing to not take seriously. But it is too small a thing to take too seriously. Your work is one-sixth of your waking existence. Your career is not your life. Behave accordingly.” (The Atlantic)

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Personal Updates

Career Moves
In the next couple of months, I’m going to announce a big career update. In keeping with the tradition of this newsletter (see May 2020 & October 2021), I’ll give it a dedicated post and explain all the reasons I made the leap. But suffice to say, I’m feeling really energized about the new gig (which long-time readers know is the game I’m playing).

All that said, if you’re an early-stage investor or a People/L&D leader and you want to learn more, drop me a note 🙂

Invisible College
One of the reasons I’ve been able to make this move is because for the last few months, our amazing Community Lead, Lyle McKeany has been running the Invisible College community and collaborating with my co-founder Rockwell Shah to make it better and better (web3 cohort-based course?). I’m excited to keep playing a role in the community and collaborating with these two wonderful humans. If you don’t already subscribe to the weekly Invisible College newsletter, you should check it out here.

Jungle Gym
Last week, we passed 9,000 subscribers (which is nuts).

I appreciate all of you who hit the subscribe button at some point, whether it was one week ago or back in February of 2019, when this thing started.

Despite the rachet-up of intensity that’s accompanying this new career move, I’m going to do my absolute best to keep publishing each month. Based on the experiences I’m having each day, I expect to have lots of cool learnings to share.

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Thanks for reading today’s issue of the Jungle Gym. If you enjoyed what you read, I’d really appreciate it if you could forward it to a friend, family member, or colleague who you think might like it too.

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Until next time,

Nick