The Elephant in the Room 🐘

She isn’t so scary after all

Diana Smith
3 min readNov 1, 2016

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When you join an early stage startup, the company as a whole is the most important thing. There are no this department’s or that department’s goals. You just need to get shit done, ideally the right shit, as quickly as possible.

Because you’re fighting for your existence, every decision is critical. Debates are vigorous. All sides are raised. Inconvenient truths are welcomed because each new piece of information could tip the scale one way or another, and everyone desperately wants the company to succeed.

I call these unwelcome yet fairly evident realities the elephants in the room.

I’ve noticed recently that as companies get bigger, new employees find it much harder to point out elephants—mostly because they haven’t built enough trust yet.

An elephant might be the contrarian idea that your support team should stop spending a ton of time helping customers with particular work around, and the product team should address that use case in the platform instead. Another fairly common elephant is the glaring and unfortunate fact that you underestimated how long a project would take or overestimated its results.

When you’re focused on the best thing for the company these elephants feel more like puppies. They are welcome.

However, it’s not easy for most new teammates to gather up the gumption to jump on the table and give Dumbo a rub behind the ear. What if you’ve made an incorrect assumption? What if no one wants to hear it? Pointing out these elephants to people you barely know and who don’t trust you yet is a lot to ask.

The consequence of a fast-growing company means that new people come into your family at a rapid pace. It’s easier for them to prioritize themselves or their department over the whole company because that’s the context they have.

Trust building takes longer because instead of meeting 10 people to start, and each new person 1 by 1 as they come in, you have to meet 100 new people from the beginning. It takes longer to learn your teammates’ quirks and hobbies, the names of their kids, what they were hired to do … and to find that north star of the whole company.

All of these things are required to be able to say the hard things, the things no one really wants to discuss but are waiting to trip you up at the most inopportune moment.

The early folks, on the other hand, had the privilege of building trust and credibility over time. At Segment, we exposed many elephants, and nearly every time, we were praised for this behavior. Our CEO even annotated our company value of Tribe to encourage our “unfailing willingness to face reality head-on, happily give tough feedback to anyone in the company, and know that we appreciate every last word of it.”

This type of encouragement is rare. Many company cultures actively discourage elephant airing. And when teammates brush off an elephant you so kindly introduced, or reprimand you for welcoming her to the table, the next time, you might just keep her in the corner and wave to her under the table, letting her know you saw her even if no one else did.

That doesn’t help build strong companies.

I’ve been thinking about how we can speed up the trust building required to welcome elephants into the room at Segment. One thing I’ve done is is document and promote a culture of “Elephants Welcome on my team. I’m hoping that by communicating elephants are indeed welcome during onboarding, via our strategy documents, and continually at meetings, I can help newcomers feel comfortable with the gentle giants.

After all, fresh eyes have the best chance of spotting the elusive animals we can’t see.

Thank you to Peter Reinhardt, Maya Grinberg, Brian Hertzog, Brent Summers, Skip Everling, Kevin Niparko, Chris Sperandio, and JJ Nguyen for reading versions of this post.

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Diana Smith

Curious. Park wanderer. Devil’s advocate. Learning every day. Marketing at Twilio.org, previously Segment.