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  • Writer's pictureBen Kettle

🗺 Evolving Your Organizational Culture

Updated: Jan 3, 2022

Ridding ourselves of personal culture fit opens opportunities to improve our workplaces. Here's how.

Hey Everyone,

This is my second post on culture fit. Is it the last? Definitely not.

If you missed last week’s post on Personal vs. Organizational culture fit, here’s a link to check it out. To provide a little extra encouragement, I made a meme last week, and whoa, did people dig it.

Thank you again for reading!



Way back in May 2020¹, the CEO of Shopify, Tobi Lutke, tweeted this:

He makes a great point.

Last week I wrote about how “Culture Fit” has been co-opted to mean “Personal Culture Fit,” why that’s no good for anyone, and that we should screen candidates based upon Organizational Culture Fit instead.

This week I’ll talk about how Organizational Culture Fit can empower you to create an adaptable organization. Much like Mr. Lutke advocates.²

My goal with this post is to:

  1. get you to think about the factors that contribute to your ever-evolving organizational culture fit

  2. help you can anticipate those factors

  3. Ultimately develop a roadmap for where you need to be

Let’s start with why your organizational culture fit will change.

The Catalysts for Cultural Change

What constitutes a culture fit at your organization will evolve. Those catalysts include, but aren’t limited to, the following factors.

Generalists vs. Specialists

Smaller companies and decentralized teams at big companies tend to be made up of generalists. These are the people who “can just figure it out,” “can wear lots of hats,” and “hustle.” Conversely, larger, more complex organizations tend to be made up of specialists. These specialists are good at a skilled task or specific piece of a process.

In general, the bigger you are, the more your need specialists.

For example, lots of successful startup salespeople are good at the entire sales and marketing process. They can make their own sales collateral, have zero problems cold calling, and don’t expect or even want training.

But if you’ve ever hired a big company sales rep for a startup, you know that it doesn’t often work out. Why? Because big company reps tend to be specialists. Sure they’re better closers, but they expect an extensive support organization and struggle with the constant change and ambiguity that’s common at less mature companies.³ It’s no surprise it doesn’t work out.

Moving from Culture Fit to Culture Add➕

Another evolution you’ll need to make is from “organizational culture fit” to “organizational culture add.”

“Culture Add” has become a popular way to think about candidates, and not without good reason - “culture add” positively frames cultural differences as assets rather than liabilities.

As your organization grows, you will become aware of your cultural deficiencies. Maybe you’re too demographically homogenous, or perhaps your workforce doesn’t reflect your community or your customer base. Either way, you’ll encounter a time when your current organizational culture fit isn’t a competitive advantage - that’s when’s thinking in terms of “culture add, ” rather than “culture fit” becomes critical.

Rise of Remote Work

Plenty has been said about the effects of the pandemic on our work culture so I won’t belabor the point here.

The bottom line is that the COVID-19 pandemic has dramatically changed how most people work. As a leader, your job is to understand the effect remote work will have upon your organization and navigate your cultural values accordingly.

Intentionally Evolving Your Culture

Changing, improving, and adapting your culture starts with an intentional acknowledgment of what needs to change and when.

Before posting a new job, sit down and think to yourself about what your organization will need to be in the next six months/year/decade and how you can intentionally move toward those goals with this hire. Need some help? Here are some example questions to ask yourself:

  • Is this person a generalist or a specialist? To what degree do we need them to be either?

  • Can we afford to let this person develop, or do we need them to produce now? Realistically, how much guidance and training can we provide?

  • What does this person bring to our organization in terms of how they see the world? Are their experiences materially different from our own?

  • Will this person make us think differently and challenge assumptions? Realistically, do we want them to?

  • Does this person reflect our customer and community base?

When asking yourself these questions, it’s essential to be honest about where you, your organization, and your current culture resides.

It’s equally important to be transparent with the team. It can be challenging for a company consisting primarily of loyal generalists to embrace the input of new specialists. Just like it can be disruptive for recruiters used to one, homogenous, talent pipeline to find new sources of candidates who represent a more of a culture add.

No one ever said evolving is easy, but it’s a lot easier if you’re aware of where you need to go. With a little planning, foresight, and honesty you will get there.

Further Reading


1 It feels like ten years ago, doesn’t it?

2 Shopify’s stock is up 5x since that tweet.

3 SaaStr has a great article on the 48 types of VP of Sales that outlines, in great detail, the different kinds of VP of Sales you need at every stage of growth. If you’re in sales leadership or needing to hire sales leadership, it’s worth the read.

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