Field Notes · 20 October 2026

Hire More Outsiders

Complaining about the cost of labor in a buyer's market? Sounds like a lack of imagination

It's hard to find good people

Perhaps. And yet perhaps we're looking for the wrong things. Put aside the typical hiring checklist — 'maximum experience'; 'has previously done exactly this role in exactly this category'; 'says they buy in to our mission' — and imagine a world where we think about traits rather than identity.

A third of our time is spent at work. It's easy to mistake what we do for who we are, and natural to do the same when it comes to applicants. Some roles really do require the most senior, experienced, on-paper excellence. But if you're using the same approach to hire everyone, there's a better approach that almost no one follows. Hire more outsiders.

Traits over identity

To find outsiders to take chances on, you need to identify the essential traits of the role you're hiring for. Imagine that's an Account Manager (AM). The kind of AM I want on my (agency) team:

  • Is easy to like; can both tell a joke and explain a technicality in terms the client can understand
  • Thinks in relationships; they will keep in touch with clients even when they're no longer clients
  • Cares more about the client than their own employer; they will fight for resources internally to get the client what they want
  • Advocates for the person on the client side; the client rep. being promoted is a personal win for the AM

This short list of traits far outweighs the rote resume of the average applicant, which would read like the following:

  • Supported a team of four account managers across 20+ client accounts
  • Prepared weekly status reports, meeting agendas, ...

ZZZZzzzZZZZzzz

It's easy to be impressed by resumes. You should care far more about what you can learn about people who effortfully apply to roles that are new to them or 'above' what might be expected. No resume will honestly dissect:

  • This candidate's contribution
  • Their ability to speak up when something feels off; to see around corners
  • Their willingness to tell you when they're too busy/need more work
  • Their proactiveness to learn on and off the job; they learn quickly

The answers to these four points will determine success in ways resume bullets never will. Imagination, enthusiasm, and effort will bridge experience gaps quickly in a learning organization, rapidly outpacing the value of candidates with more 'correct' experience, reinforcing your ability to teach what you do to the people with the appetite to learn (and the energy to put it into action).

Outsiders never stop learning

The highest value quality you can buy in an employee is 'low-ego-big-appetite.' Something outsiders have in common, despite the gaps in their resume.

Some examples of outsiders we might consider for hiring as an AM:

  • Bartender: reads a room, trades banter easily, remembers regulars’ names and stories, and balances what the patron wants against what the house allows
  • Teacher: turns complex material into plain language, uses humor to keep people engaged, and counts a student’s later success as their own win. Stays in touch with former students
  • Nurse: explains medical jargon to scared non-experts. Pushes back on their own institution to get the patient what they need
  • Wedding planner: stays calm when things go sideways, centers the client’s day over their own preferences, and wrangles vendors on the client’s behalf. Business runs on referrals from past clients
  • Agency recruiter: thinks in long-term networks, keeps in touch with placed candidates after the deal closes, and genuinely celebrates when someone they placed gets promoted

Outsiders inject new life into groups. Their perspective, especially if they're used to working in a different category, enriches the status quo, challenging the local norms and enhancing our ability to adapt to change. That's a competitive advantage and a winning characteristic too rare in small firms.

A buyer's market

Further down the list of reasons to hire outsiders is that they're more affordable if (and it's a big if) you're trying to run a learning organization. If you're open and determined to run a properly leveraged firm (you employ a mix of junior-, mid-, and high-level professionals) then part of the deal is opportunity. You're hiring a junior in this discipline (AM, in our example) and they're a level one AM. But because they're voracious learners (and you excellent teachers) they will rise disproportionately fast. Hiring outsiders is a good idea on its own, but if you're in need of help but struggle to afford it, it's a great idea to find someone who understands what you're doing:

We're giving you a chance; we expect you to work hard, learn quickly, and contribute fully; you will leave here with a wealth of experience

Complaining about the cost of labor in a buyer's market? Sounds like a lack of imagination.

Hire more outsiders.