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Our Office Snacks series is where we have an informal conversation with expert members of our community to delve into their varied buffets of experience and come away with juicy insights and ideas.

This time we chat to Jenn Oswald—regular speaker, Head of HR at tech startup Goodtime.io, and founder of Chief, a network built to help more women occupy positions of power.

It’s always fun and inspiring to chat with Jenn. Listen/watch/read to get her valuable insights into building an entrepreneurial culture, remote working, the role of managers, servant leadership, recreating the office vibe at home, warding off digital fatigue, and of course, favorite office snacks!

Becca Banyard

Hey Jenn. Let’s get started right off the bat. You’re Head of HR at Goodtime, could you explain a little bit more about what you do there? 

Jenn Oswald

What I'm working on right now is building out the people function. So that's HR, recruiting, culture, talent, all programs, all systems. We're building a lot of the HR infrastructure and basic strategies and processes. That and lots of working with the employees to build programs that work for them in order to scale our culture.

Becca Banyard

Amazing. So I'd love to take a moment and to talk about remote working because and how it applies to culture. First off, do you think remote working is here to stay? 

Jenn Oswald

I do, especially because we can't seem to shake this darn Coronavirus and all its variants. The majority of companies that I've seen are remote or hybrid now, and I just think it's going to become a thing of the past to be a hundred percent in the office. Companies are going to be either more remote friendly than they used to be or hybrid or fully remote. We're going fully remote.

I have a little theory that people decide in their first 30 days how long they're going to stay with an organization.

Becca Banyard

How has that process been and  how have your employees handled that change? 

Jenn Oswald

The interesting part is that people are so resilient and adaptable, but one thing that's hard for most people are the gray areas. So I think knowing what our plans are and how we're moving forward was a sense of relief for people. 

We are headquartered in San Francisco and had a pretty large office there and really only hired a few roles outside of San Francisco. We did have people outside of San Francisco that were fully remote, but we didn't have the strategy around that. If someone that we knew was remote we’d hire them there, but this has been more about really having a remote strategy. 

So far, I think people are happy. We made the announcement in September and we asked people “Where are you, where are you located?” So we made sure we're doing all of the employee things correctly based on the state, and we do have a couple of people in Canada too. 

Becca Banyard

Nice! It's really exciting that you're going to this new remote model and I'd love to know how you stay connected with your team members in this new environment without suffering from Zoom or digital fatigue?

Jenn Oswald

You know as far as the Zoom fatigue I can only answer that for me personally. But I can talk a lot about how we stay connected. Some days, as you know, being on Zoom all day is harder than others. What keeps me from being Zoom fatigued is the fact that most of the meetings that I'm in are highly worthwhile. 

I get Zoom fatigue when I'm in a meeting and I'm like “Cool. Why am I here? What are we trying to accomplish?” So, for me, it's really about that engagement factor. Also, we're a GSuite based company so there's a setting in your calendar settings where you can basically shave 10 minutes off every meeting. So an hour meeting is 50 minutes, a 30 minute meeting I think has maybe 25 or 20. That gives a little  break so you can walk or get some more water.

Also, maybe I shouldn't say this, but I have a device that connects to Amazon that plays music in another room and I've started playing low volume music out there. That kind of reminds me of being in the office and so, when I remember that, that makes me happy and I think happiness combats fatigue. So those are kind of just my thoughts on Zoom fatigue.

Related Read: 10 Best Board Meeting Software For Board Management Online

Becca Banyard

That’s a great idea!

Jenn Oswald

Haha yeah. And the way we are staying connected is we have a group at Goodtime called the EIA or the Emotional Intelligence Agency. They’re a group of people—we try to have someone from every department—who are plugged into the culture; what's working, what isn't.

We also have virtual happy hours, virtual coffees. We use a product called Donut that introduces people and has a water cooler chat feature, which is kind of fun. One of the most popular things that we do is a new hire lunch every Monday and anyone can come. Each week we ask a different, fun question. 

Our question this last week was, ‘when you were a child, what did you want to be when you grow up?’ You learn lots of different, fun things about people.

That's what culture is, it's the difference maker in any company.

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Becca Banyard

That's awesome. We recently started using a Slack integration called Know Your Team, which I think is similar to Donut, and prompts the team with different questions like ‘what movie have you recently watched that was really good?,’ or ‘what was your first part-time job?’ And you mentioned your new team member lunches, are there any other ways that you onboard employees in this remote environment? 

Jenn Oswald

Yeah. So we've really spiced up our onboarding program. 

First we try to have all of our systems talk to each other so that, when someone goes from applicant to a new teammate, there's minimal work inputting themselves into the system. That’s the technology side and we also send out a new hire email to the entire team, and to the person, as soon as someone accepts a job. That means everyone is welcomed before, and people just reply all, and it's just a nice intro. It's unexpected. Little things like that go a long way.

We also have a digital onboarding training curriculum that is about three days long—not three days total but it takes people usually about three days to complete— and then we also have a first day program that’ s led by the people team. That's talking more about our business and Goodtime by the numbers. Then, after that we hand them off to the team and every team is responsible for helping the new teammate create a 30, 60, 90 day plan.

That’s important so that people can feel like they're learning the right things and like they're moving the needle forward and being successful. Also, from the people side, we do a 15 day check-in and a 45 day check-in to see how they're doing and how they're adjusting.

Becca Banyard

Interesting. Can you tell us a little bit about that?

Jenn Oswald

So the 15 day check-in is really focused on if the job is what they thought it was. And then at the 45 day you're measuring that but then also what's changed, what's the overall kind of mood of the new hire? I have a little theory that people decide in their first 30 days how long they're going to stay with an organization. 

Becca Banyard

Oh really? 

Jenn Oswald

There's no science behind that. That's just my theory. So it's a hypothesis. Maybe if I go back to school, I'll do that as my thesis. 

Becca Banyard

Even if it's not ‘scientific’ it goes along with how important first impressions can be.

Jenn Oswald

Yeah, totally. 

Becca Banyard

Let's just switch gears a little bit and talk a bit about the importance of management. How do you see the role of managers in an organization?

Jenn Oswald

I believe the more someone is a coach and a mentor versus a manager, the more successful the people that work with them in the organization will be. Management is a space that does take a lot of finesse and a lot of work, so really tuning into the higher EQ people and informal leadership is as, if not more important than, formal titles of “I'm a manager” or something like that. 

Becca Banyard

What does informal leadership look like to you? 

Jenn Oswald

It's kind of the basics, it’s doing the right thing in helping people out when you see that someone is struggling, checking in with others, modeling the way. Those are the basic things and then also staying away from the negative. I don't want to do the whole ‘let's just be positive’ thing, but I believe focusing on the good, rather than honing in on the bad, does a lot for leadership and also just the human psyche. 

Becca Banyard

Yeah it's really good. Kind of following along those lines, is there anything else that you base your management style on?

Jenn Oswald

I tend to be a bit high-level and a bit hands-off. I ask people what they want and I think it's my job to flex to their needs rather than the other way around. Overall, I think people like questions and they like being asked “How do you like things? How do you like to be led? How should we handle it if there's a problem?” Having that type of frank discussion before anything gets too dicey is really helpful. 

Becca Banyard

Are there any companies in particular that you admire for their approach to HR or how they manage people?

Jenn Oswald

Yeah I admire Atlassian, Asana and, this is a little basic maybe, but Netflix—they’ve done so many groundbreaking things that we're still doing today. And there are a lot of companies that I admire but maybe I don't know as much about their HR practices.

Becca Banyard

Talking about big companies like Netflix and Atlassian, how important is company culture in general and also personally to you?

Jenn Oswald

I think it's the number one thing, both to a company for me personally. It's what keeps you with an organization. If you're all a part of the same culture, you're speaking the same language, you deal with things in the same way. You have healthy conflict, you have successes, you have failures, you have safety, right? You have celebrations and you have, “Okay guys we could have done it better.” 

That's what culture is, it's the difference maker in any company. At places like Atlassian, who have done a really great job of scaling their culture, they're really communicative with their employees. So I think communication and culture go hand in hand and it’s a big part of culture too.

Related Read: 5 Subtle Signs Your Workplace Culture Is Turning Toxic (And How To Fix It)

Becca Banyard

Agreed. I know you said that you're building a culture of entrepreneurship at Goodtime, what is a culture of entrepreneurship and how do you go about building it?

Jenn Oswald

You know, it's so funny because I was talking to somebody today just informally and they said “I was always told when I was looking for jobs if someone said we're looking for entrepreneur types to run far away, ‘cause that means they want you to work 80-90 hours a week.” And I was like, “Oh my gosh, you never know what perceptions people might be coming in with.”

So that was really interesting. But our culture of entrepreneurship was born because at a time when we had what I would call a ‘fractured culture.’ We had a group of people that were very disengaged and dissatisfied with things and were very vocal. We tried but sometimes, when that happens, there's really nothing you can do to appease that group, and I've always been of the mindset—and my mentor taught me this—of being like “Don't worry so much about why people go. I mean, yes, care about retention. I'm not saying don't. But think about why do people stay?

And so what we've done is study why people stay and what are those trends? And so our culture of entrepreneurship is really built on three pillars: autonomy, accountability and collaboration. So we’re a very flat organization and people understand what decisions they can make and when they need to collaborate.

We don't want a lot of bureaucracy here, we want people to feel empowered to make decisions. So we are working through some of the tricky things like how do we launch that from an HR, people perspective? Can people get more compensation? Absolutely. Should we have annual performance reviews? We have bonuses, we have equity, things like that.

We want to recognize people for the impact that they have in the company and a title can't describe that. So we stopped calling our leadership team the executive teams because what does the executive team do? They don't exec, right? So we're the strategy team. So my job is people strategy; it’s more like using a title as a way to describe your function.

But, also, we’re wary of people thinking there's no opportunities for growth. That's what I think people were a little scared of: “Is this just a way to use some fancy talk so that we work harder and don't make more money?” And that's not what it is.

Related Read: 6 Tips For Effective Employee Compensation Discussions

Becca Banyard

And how do you measure whether your employees are happy or not? 

Jenn Oswald

You have a lot of conversations. You build trust, you do continual check-ins, you get to know people, you do what you say you're going to do. We do use the employee net promoter score as our main source of measurement, but we measure our programs as we go too. So gathering constant feedback or really thinking about “What's our listening strategy. How do we listen?” 

Becca Banyard

You mentioned just now and recently on the People Managing People forum all the reasons why people should stop doing an annual review. I'm curious what your recommendation is for organizations to replace their annual review? 

Jenn Oswald

Yeah, so we want to replace the annual review but we need people to feel good about how they can grow their careers. So what we're really looking at, and what my suggestion would be, is an iterative process and making sure people know “If I accomplish this, then I get this.”

But annual reviews are so outdated. Sometimes what you get done in a quarter is more than some people get done in a year or so! So why would I get the same increase as someone else? I think there’s a lot of bias in annual reviews, and I've not seen very many places do them well, so why do we keep doing them? Because, you know, in the 1950s we decided it was a great idea.

We've not evolved very much in the people space in some of those instances. So now I think it's being iterative. You have a feedback loop, and you're continually managing people up or out, and you should be continually growing people and making sure they're rewarded for that.

People that aren't working out will either find their own way to a different place, that’s a better fit for them, or we'll ask them to do that and, hopefully, those instances become fewer and farther between as you continue to grow the culture. So that's my ideal state.

We don't have it fully baked as to what the alternatives are, but people associate the performance review with compensation, so let's look at compensation separately and do it as a reward for your impact versus a budgetary experience.

Becca Banyard

And for organizations who are looking to remove the annual performance review, do you have any advice for them on how to go about that? 

Jenn Oswald

I think you have to test some different things before you just completely shut it down. So think about your strategy for ensuring that people are moving in the direction and are aligned with the mission, vision, values. Then also if there is a high level of accountability or are things lacking? 

Take a look at those things first so that you set yourself up for success but, if you move away from the performance review, you still need a meeting cadence. So we have daily stand-ups, we have weekly huddles where we're solving problems, and then we have strategy sessions as well as ad hoc meetings depending on the problem.

Related Read: 10 Best Board Governance Software for Board Members

What works for us is having each team doing things the same and then everything is aligned with our overall purpose and what we're doing. But every organization is going to be different and my recommendation would be to first understand your current state, what works and what doesn't, and then make small changes and see how they go.

Of course, if the end result is getting rid of that annual performance review, you do have to figure out how compensation works and how people will grow their careers. So you will have a few things to figure out along the way.

Related Read: Best Employee Compensation Management Software 2024

Becca Banyard

That's great. Thank you. We're just almost at a time so I wanted to end things just with an important question. What is your favorite office snack? 

Jenn Oswald

Ooh, gosh, I'm a sucker for potato chips. I can't help it. Really, any form of potato is kind of my thing. But yeah, give me potato chips and I can't avoid them.

Becca Banyard

Do you have a favorite flavor? 

Jenn Oswald

I like the cracked pepper or the jalapeno. What's your favorite? 

Becca Banyard

My latest favorite is apple cider vinegar. We have a Canadian brand called Hardbites and they're really not too greasy, not too salty, just the right amount.

Jenn Oswald

Yeah we'll have to exchange. We can be potato pen pals and exchange our favorite chips.

Becca Banyard

I love that! Thank you so much, Jenn, for spending a bit of time with us and sharing all your insights into the world of people and culture. I really appreciate it and we’re so excited to have you in the People Managing People community as well as an expert.

Jenn Oswald

Pleasure!

Enjoy this? Have some insights of your own to share? Connect with Jenn and other HR and people experts in the People Managing People Community forum

Or gain even more exciting insights by checking this article out: Maintaining The Candidate Experience Through Rapid Scaling

By Becca Banyard

Meet Becca, the host of the People Managing People podcast. On the show, Becca connects with People & Culture thought leaders and HR & Leadership experts from around the globe to tackle the most pressing issues in today’s world of work.

With her love for people and her desire to make a meaningful difference in the workplace, she is committed to building a world of work that is joyful, human, and inclusive.

Beyond her work on the podcast, Becca is also the Multimedia Producer at Black and White Zebra.

In her free time, you can find her snapping pics for her foodgram, singing songs with her guitar, or honing her figure skating skills (that are almost non-existent).