I avoid writing about topics that is a direct reference to where I work. You never want people on your team to feel like you're writing about them on a personal newsletter. However, I will write about themes I feel are universal challenges every company encounters and spans beyond my own experience. With that, let's talk about the Oil and Water Problem.

Oil and water don't mix because they have different molecular structures and polarities. This difference in polarity prevents them from forming stable mixtures, causing them to separate into distinct layers. Oil and water are the metaphor for startups rapidly growing when one polarity mixes with another.

The first group are the old guard (OGs)—tenured employees super early when the company started. The second group is the new guard (NGs)—tech veterans who contributed to successful scale at previous companies (those from the minestrone of talent). The Oil and Water Problem is the most common points of contention within companies and crucial to address. Let's make sense of the points of view of both groups, identify typical tension points, and what you can do to mitigate the segregation of cultures.

The old guard point of view

The OGs at startups are the earlier believers who joined before others joined. Many of them are the first community members who sent the founders feedback and ideas. Because of this early start, OGs have superior knowledge of the product, not only how it works, but all the gotchas and skeletons in the closet. This context is crucial and are a big reason why OG team members are a lynchpin for historical information.

Since the OGs joined early, they may not have the experience of what happens next when a company goes from scrappy startup to a larger scale. They might wonder why new hires are coming in and taking over in areas of leadership and strategy as they've ben the earliest believers and loyal.

The new guard point of view

The new guard are the minestrone of talent that arrive when a startup found product market fit and growing. These individual come from roles as operators of a specific function (such as Product, Design, Marketing, etc.) and have expertise scaling those groups.

Despite having a lot of experience at other companies, the new guard are unproven in the eyes of the OGs and founders. Whereas the OGs have gone to war with the founders for many years, the new guard have no battle scars. They don't have the same organization and product context of what's happened internally before.

Common tension points

There is a famous Looney Toons scene (E25 - S23) where Bugs Bunny and Daffy Duck argue over Elmer Fud's hunting license—is it Rabbit season or Duck season? What ensues is a back-and-forth of Bugs and Daffy ripping that sign that depicts the other one being the season hunted.

Bugs: Duck season!

Daffy: Rabbit season!

Bugs: Duck season!

Daffy: Rabbit season!

(Repeat)

Find-replace for Bugs and Daffy, and you have the old guard and new guard. In my experience, there are a few common areas where tension points occur like two tectonic plates colliding on the Earth.

Process

The first tension point is processes. Operational excellence is not the top priority in the early stage. Process done the wrong way can hinders progress and result in performative work. However, how a 20-person team runs and a 2,000 person company runs are drastically different (and should be). What results is a debate on when processes need to evolve.

OG: "We've always done it this way."

NG: "This won't scale. Here's how we did it at [Company Y]."

Decisions

Stakeholders and who make the decision changes in this phase.

OG: "We should have input in this decision."

NG: "It's been decided."

Communication

In addition to operating procedures, you can expect meetings and communication constantly change in the growth arc of a company as it multiplies. In places where I stayed for four years, it felt like four different companies based on the growth.

OG: "I need to be in this meeting to know what's going on"

NG: "We'll send out meeting notes for everyone"

Access to founders

The hardest thing for a founder to deal with is when they can't scale the relationship like in the early days. They used to be able to hand write the holiday cards personalized to each employee. At a point in time, the cards then become branded company cards with a printed message.

OG: "I used to be able to Slack message the founder easily."

NG: "I'll let you know what comes out of the exec meeting"

The new guard becomes the old guard

A universal truth working in startups is eventually scale will get you. Those who were the new guard at the Series B growth become part of the old guard after years of being at the company. What happens next is an even newer new guard comes in to take the company to next level—late stage to IPO. Suddenly, the original OGs and former new guard have shared experiences of what it feels like with a new regime coming in. For the new guard, it's important to have empathy for the OGs because how they feel with you coming in will happen to you at a point in time.

Turning oil and water into ice tea and lemonade

I've been part of the new guard at the previous place I worked. I've learned what worked and what didn't. Whether you're an OG or new person coming in, be that person who infuses the two cultures together. This meant spending a lot of time with the founders to expand and scale their mission, talking to as many customers as possible, and dog fooding the product daily. You have to jump right into battle to gain trust. Spend time with the OGs, understand what's been important to get here. If you aren't able to integrate, you won't make it and things will quickly fall apart.

To be abundantly clear, integrating the two cultures isn't about making everyone happy as that's not alignment. Larry David once said, "A good compromise is when both parties are dissatisfied." The goal is constantly having input and continued improvement in blending the best of both worlds together.

Avoid the Oil and Water Problem and strive to be the Arnold Palmer of tech companies—a harmonious blend of two delightful substances (ice tea and lemonade) that create a delightful experience.

Hype links

Collection of what I read and related to this week's post

• Barron Webster from Replit is speaking at Config. You won't want to miss this!

• The four types of software in the future → Posted this on my website so it’s free for all¹

• Congrats to Stashpad for launching Stashpad Docs (instant collaboration)²

Job opportunities

• We're hiring at Replit

• Design Intern at Replit

• Sanity is hiring a Senior Product Designer, Growth → Go work for Linda!

• Mercury is hiring a Head of Product Design, Growth

• Mercury is hiring a Head of Product Design, Banking

• Lindsay M. Pettingill has an awesome newsletter of curated jobs. Here is the March edition