How to banish fear from company culture (Part I)

By Henri Hyppönen

“How are you feeling?” Lisa asks Alex.


“Terrified” Alex replies.

“I feel like you’ve been out gathering information about questions you can ask me. To make me feel uncomfortable.”

This dialogue between Lisa Chow and Alex Blumberg on StartUp, a podcast about building up a start up, was most likely hard for both of them. It started out in an light manner, but there was an anxious undercurrent to the conversation. They were about to discuss things that were not functioning well at the company where they both work, podcast powerhouse Gimlet Media .

To be precise, Alex Blumberg is not only working for the company—he is also the co-founder of Gimlet. So the podcast we hear is in many ways the brainchild of this accomplished producer. Aside from being a superstar editor, Alex is also the host of StartUp. Lisa Chow, as you most likely figured out, is the other host—and they are both living up to the promise to tell the start-up story that you never hear. In the last two episodes of their podcast, they went at it, and in doing so may have taught us an invaluable lesson: How people behave in companies when they are not afraid.

StartUp is as honest as a podcast can be. It’s as close as one gets to a thorough autopsy of a company. Of course, there is the lure of “good material,” which I am familiar with from my personal experience working in radio. If something real happens when the microphone is on, there is a high chance that it is A-quality material. A “good material lure” lowers the barrier to publishing even the most embarrassing conversations, but even if it does, it is still rare to witness the nakedness and often brutal honesty that you hear in the StartUp podcast.

On the last two episodes of the StartUp mini-season, Alex and Lisa took their brutal honesty to new heights. First, when it was time to talk about diversity at Gimlet Media, Alex conducted some uncomfortable conversations. Although Gimlet is likely to be one of the more liberal workplaces, some surprises surfaced. I can’t say what Alex was going through on an emotional level, but it sounded like it was unnerving for him to hear about things he hadn’t even thought about (such as a religious colleague who’d rather keep his convictions to himself).

After that episode, “Diversity Report,” Lisa started walking around the company digging up problems—especially the disorganization of the whole company. Unfortunately, that is generally one of Alex’s responsibilities, so as a result people couldn’t tell who their boss was—causing ongoing confusion about who would make the last call on editorial questions. This was the case with the Reply All team (another hit podcast from Gimlet). They got into a big fight—and for good reason: Alex Blumberg and co-host PJ Vogt had changed the final edit of the show after everyone else had gone home. Co-host Alex Goldman only found out when he heard the show that was already aired. Members of the team were ready to quit.

The hardest part was still to come. Lisa turned to co-founder Matt Lieber to find out how the co-founders saw the current state of the company. Lisa asked both Matt and Alex a set of questions whose aim was to find out if there was any discrepancy in their assessments. Lisa asked them to rate on a scale of 1 to 3 (1 being low, 3 high) how Gimlet Media was doing in comparison to expectations.

Alex gave Gimlet the following grades: Quality of the shows 3 Listener numbers 3 Team dynamics 2

But then it was Matt’s turn, and he saw most areas in a different light. They both agreed on listener numbers, but Matt gave a 2 for the quality of the shows and only 1 for team dynamics.

This was difficult for Alex to swallow. “It’s really hard for me to hear numbers like that and not take them personally.” It seemed to imply to Alex that he should be doing something that he was not doing. “It’s really hard, shockingly hard.”

As the show progressed a common theme would surface for Alex: He was getting different information from people when he was talking to them in person than what he was getting now. “I feel like I’m in a bubble now,” he says. And such a feeling is always horrifying. It steals the confidence from your ability to sense what is going on and nags away at one’s trust in people’s willingness to speak their minds. That can be somewhat scary. For a while you lose your reference points as a boss.

“It’s so frightening. I will go and have the same fucking lunch with the same fucking person. And I come away thinking something totally different.” Alex felt frustrated and at the moment didn’t know what to do about it. But instead of accusing anyone else (maybe he did so in private), he went on to self-reflection. “I don’t know if I’m doing something wrong. Or if I’m somehow creating the expectation that I only wanna hear good things. Or if people are afraid to tell me bad things. Or if I’m just hearing it in a warped way that I’m not acknowledging what they are saying.” Then Alex turns to Lisa and asks, “What do you think?” Lisa tells Alex about how optimistic he is. But then there is another turning point. Lisa explains how she replayed her comment for her husband, who told Lisa she was sucking up to the boss. Lisa explains that she wasn’t saying anything that she didn’t believe. But she held something back: She didn’t say that Alex’s optimism wasn’t always a good thing.

This is what I love about StartUp. Aside from being the ultimate peer support—and also entertaining as hell—it drills deep into core of what a company can be. They are tackling hard topics and emotions head-on. They don’t avoid nerve-wracking, angering, saddening and awkward conversations. And in doing so they are not surrendering to fear-based culture. It takes a lot of nerve for Alex and Lisa to do what they are doing in those episodes. It wasn’t easy, they didn’t have all the answers—hell, some of the time they didn’t even have the questions—but they still did it. They kept their emotions in check and talked about difficult things.

I would argue that most of these conversations never happen in ordinary workplaces. Who knows if Alex and Lisa would even have had this conversation if it wasn’t for the sake of the podcast. And the reason is simple: This kind of conversation is unpredictable. It’s not safe for anyone in the conversation. Shit just seems to surface in the most unexpected places, and then you find yourself in all kinds of trouble. This could be the reason why most managers just opt out. It’s easy. It’s safe. And if the conversation surfaces anyway, you can always ignore or downplay it. And if it still persists, some managers choose to get angry and basically end the conversation there. These critical thoughts are not appreciated in the eyes of management.

After I wrote a book about fear, people stated to bombard me with the question “Isn’t a fearless culture a utopia?” and my answer is always that it is. Being fearless is unrealistic and undesirable, but being able to handle your fears in a constructive manner is an essential skill in the human jungle—and the modern workplace essentially is the new jungle. The point is to acknowledge that there will always be conversations that make you ache and conversations that push your defense mechanisms into full gear. The workplace is simply ground zero for facing one’s fears.

I’ve noticed, as a creative, that this is the thing: The ability to do scary stuff and socially risky stuff and still maintain trust-based social connections to others is the propellant for creativity. But we are prone to regress to evasive and defensive behaviour when faced with risky situations. When we go down the path of fear, it starts to derogate the superpowers of even the most potent teams. Ultimately, fear’s role in a company’s culture can be either that of rocket fuel or kryptonite. It seems that at Gimlet, they choose the former.

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