Being an “a” vs. a “the”

I began writing this series with the goal of providing a tactical behind-the-scenes look at what I was working on and what I had learned at Greenhouse Software. After 18 months at the fast-growing startup, I left to join the even faster-growing WeWork, a global tech and real estate organization with over 3,000 employees, operating in 20 countries around the world. While both roles were functionally defined as Business Development and share the overarching goal of creating long-term value for the company, that is where the similarities end. At a large organization, you’re an “a” - meaning one of many in the same role or with the same primary function - while at a small company, you’re more likely to be a “the” - the one and only of that specific job or function. From my experience, both an “a” and a “the” will come with challenges and opportunities and while I have a personal preference based on my strengths and personality, one is not inherently better or worse than the other. I’ll highlight the dichotomy to help identify which might be a better fit for you based on:

1. Focus
2. Resources
3. Impact

Mile deep vs. mile wide

When you’re a “the” you’ll find yourself constantly jumping from one initiative to the next, never feeling like you’ve ever really gained expertise. This is often times a function of being pulled into something (read: forwarded an email or pointed to in a meeting) that while not part of your domain, happens to be closest to it by either function or title. Other times you become a victim of your own ADD or lack of organizational bumper lanes to wander into something new. While it can be exciting, some people will find this constant state of change to be frustrating and stressful. Also, without having the benefit of constant repetition, it becomes difficult to achieve mastery - jack of all trades, master of none. An “a” is able to focus for months at a time, if not longer, creating comfort and bankable hours toward 10,000 (h/t Malcolm Gladwell). This repetition drives expertise which builds confidence, creates concrete results, and could make you more employable to a larger organization in the future looking for a specific job function.

Personally, this was the biggest change I needed to adjust to between Greenhouse and WeWork. Despite having functionally the same title, at Greenhouse I worked on an outbound partner referral strategy, a consultant certification program, signing event sponsors, and structuring product partnerships - not staying on one ever long enough to gain mastery (a mile wide)! At WeWork, I was hyper-focused on creating channel partnerships with other businesses that were looking to reach our Members or that our Members were looking to reach - building somewhat of an expertise along the way (a mile deep)!

Dilbert knows best

Resources at an organization are typically driven by clear objectives and team headcount.  By definition of being a “the,” you’re a headcount of one and the amount of budget you get will match accordingly.  With a focus that can be ever-changing it’s also challenging to get time and non-financial resources from other teams. This lack of resources will create frustration from time-to-time, but can also become a driver of hustle and creativity.

Relatively speaking, the resources that come with being an “a” will be abundant. You have a clear focus that you can use to formulaically justify a required budget. You’ll also have a team to amortize a larger budget and one-off expenses across. Similarly to having a consistent focus, having a larger budget and access to more resources creates a level of comfort for an “a” that is hard to imagine for a “the”.   

A classic question about fish

From schools to sports, we’ve been asked if we want to be a small fish in a big pond or a big fish in a small pond. For anyone not familiar with the metaphor: the idea is that in a smaller surrounding you will have greater impact than in a larger surrounding. There are a lot of great ways to visualize this, but here’s my favorite :)

As a “the” you’ll have more impact and influence on your organization, but that organization (almost certainly) will have less of both on the universe. As an “a” your contribution will be smaller in context, but collectively all of the small fish will be having a greater effect on a company that in turn will have a greater effect on the world (see the visual above again for confirmation). I think this is the most difficult dimension to come to terms with on the internal debate of being an “a” vs. a “the” as it incorporates ego, humanity, and a sense of self. Having a large impact on a small organization can be extremely gratifying and energizing for some, while others will feel unfulfilled until they are able to impact millions of people which is much more likely to happen at a larger organization.

So which is better?

As mentioned in the intro, an “a” and a “the” both come with challenges and opportunities. While I don’t believe that one is inherently better or worse than the other, I do believe that one can be a better fit for someone and ultimately lead to more professional success. I’ve been fortunate in a relatively short career to have been able to experience both and I hope that by highlighting the differences it will help you better position yourselves for success.

Stay tuned

I’ll continue to write this series on some of the interesting things that I’m learning along the way. I love feedback so any questions or comments, please feel free to reach out directly to [email protected]

Thanks for reading!

David

David Sagalov is the Director of Enterprise Growth for Flatiron School at WeWork. Prior to joining WeWork, he helped start a partnerships team at Greenhouse Software. David earned his MBA from the Haas School of Business at UC Berkeley where his experience was focused around Entrepreneurship and Venture Capital. David began his career as an investment banker at Merrill Lynch in the Energy & Power Group before joining Jefferies where he eventually went on to lead the High Yield Research Technology vertical. He’s also earned a Bachelor’s in Business Administration, summa cum laude, with a dual concentration in finance and international business from The George Washington University, spending a year abroad at the London School of Economics. Connect with David on LinkedIn.