‘Speak Your Mountain,’ ‘Hug Your Mistakes’ — How Postscript Embraces Humility

Postscript looks for humility in its candidates and fosters it in its employees to create a culture of honesty, trust and diversity.

Written by Avery Komlofske
Published on Nov. 30, 2022
‘Speak Your Mountain,’ ‘Hug Your Mistakes’ — How Postscript Embraces Humility
Source: Postscript
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How would your detractors describe you?

That’s not a question you’d expect to hear when you sit down for a job interview. At SMS marketing platform Postscript, though, it’s just one of a handful of questions that test for an essential company value: humility.

“It yields some very interesting answers, as you can imagine,” said Jen Raines-Loring, Postscript’s SVP of people, laughing as she spoke. That question is one of four that register with Raines-Loring as successfully measuring a candidate’s humility.

“Another question I like to ask is about the best constructive feedback you’ve received, and I ask it right at the top of the interview because it sets the tone for the right level of vulnerability,” she said. “It’s not just about the feedback, it’s about what made the feedback helpful to you. How did you navigate that? The way people tell that story really gives us a lot.”

Other questions include asking about a mistake the candidate made at work and what they consider their greatest accomplishment.

“We intentionally left that last one open-ended,” she explained. “It’s about how the interviewee talks about their accomplishment — and if they consider how other people got them there. If it becomes a ‘we’ victory, that helps us see the humility side.”

“It’s a good litmus test for where they place themselves in the broader context,” agreed Director of Customer Experience Alyssa Edelman, who works with Raines-Loring on many of these interviews. “When we ask these questions, we don’t want to know just what you did — we want to know how it helped the people around you, how you translated it into learnings and takeaways, and what the impact was of what you did. Those pieces are the heart of these answers.”

Humility is a key value at Postscript, which is what inspires their interviews to test for it. Postscript employees, from entry-level to leadership, are encouraged to approach every problem with a child-like curiosity, listen to everyone’s perspectives and accept feedback thoughtfully and gracefully. That attitude is built into the company’s DNA, and it has not lost its significance.

“Humility is my favorite of our values,” said Adam Turner, co-founder and CEO. “I love it.”


Five of Postscript's employees posing in a cardboard cartoon bus that reads "Group Chat! The Tour"
Source: Postscript


What does humility mean to you?

Director of Customer Experience Alyssa Edelman: Humility means accountability – admitting mistakes and taking ownership where it’s due. But also, as a leader, it means modeling what good looks like and representing that value in the way you work, leading to a culture of psychological safety. When you’re all moving towards the same goal, it gets you there faster and in a way that everyone is proud of.

SVP of People Jen Raines-Loring: The best version of humility is about the group, not the individual. On top of that, I think it’s about loving your own mistakes — actively seeking them out, hugging them, being very comfortable with them and not hiding at all.

Co-Founder and CEO Adam Turner: Coming into a challenge and thinking that you’re right probably won’t yield the best results for the customer — coming in and saying, “okay, I have a perspective, but there’s probably a lot I could learn here” achieves the most growth for everyone involved. It means embracing a diversity of ideas that will probably lead to a better outcome than you originally pictured — the combined vision that people have is much larger than one person coming in. We don’t have room for people who want to be right more than they want the company or the customer to succeed.



How does staying humble contribute to company culture?

Turner: We add a layer of patience to everything. One of the things I do that’s become kind of infamous — or famous, I’m not sure — is creating really long, awkward silences at meetings when you ask for questions. The questions always come in the last second of silence, even if you wait for like 30 seconds. All the best questions and comments come at the end — and especially in a remote situation, I want to overcome the awkward and hear out all the ideas. Other people have taken it on, too, which I’m really grateful for.

Raines-Loring: My favorite humility story actually involves Adam — I’d say it even if he weren’t here, because it was a watershed moment in my Postscript journey. At an all hands about 18 months ago, Adam really changed my life: He got up in front of the company and was really open about how hard a period of the company’s growth had been for him. He showed really authentic emotion as he described how the pace of change, the amount of change and the pace of personal growth was really hard for him. It really changed how I think about being a leader of groups and teams of people and how I communicate. People here are more open, more vulnerable and more willing to share what they think — which has made the idea of staying at Postscript for a long time much more sustainable for me.


“No matter who I talk to here, I can come back to the fact that they have this value and be open and honest with them.”


Edelman: For me, it’s little moments between two people that really demonstrate that quality the most. Because we scan for humility in our interview process, no matter who I talk to here — regardless of how different we are as people — I can come back to the fact that they have this value. This allows us to be open and honest and drive toward the best possible outcomes together.

There’s a phrase that gets tossed around a lot here: “Speaking your mountain.” It’s led to people disclosing things about their lives and what they’re going through that I haven’t seen anywhere else. For example, this is the first company where I’ve let my whole team know that I’ve been diagnosed with anxiety, because some days, that’s my mountain. It allows us to be very human — there isn’t a completely different work version of me and home version of me.


Seven of Postscript's employees posed outside of a bus near Nissan Stadium.
Source: Postscript


How does this translate to how you partner with your teams? 

Edelman: We have a slack channel for FEACH — which are our core values — and everyone at the company is encouraged to shout people out for their achievements, as small or big as they may be. 

Also, the career ladders for our support team include both inputs and outcomes. We evaluate for promotions based on those outcomes because we want to celebrate the different ways of getting there. This lets people bring their unique strengths to their job.

Turner: In engineering, we’ve built recognition into meetings. Every week, we have an engineering management meeting, and we spend the first five minutes just sharing wins. It’s a great way for people to advocate for themselves and others and keep momentum up. I build it into all of my one-on-ones, too — at the top of the agenda, we share a win from last week. I like keeping the positivity up. What we’re doing is supposed to be fun!


“Humility is best complemented by fearlessness.”


Raines-Loring: Humility is best complemented by fearlessness, which is the F in FEACH. That combination is really important — while we’re focusing on humility today, fearlessness is also about being bold, putting yourself out there and not being afraid to make mistakes. I think we do a good job of talking about both, and making people see that Postscript culture rewards all the core values, not just humility or fearlessness on its own.


Responses have been edited for length and clarity. Images from Postscript.

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