CTO Connection Podcast

Short Byte: Tim Olshansky - Managing hybrid remote teams

June 17, 2021 Peter Bell
CTO Connection Podcast
Short Byte: Tim Olshansky - Managing hybrid remote teams
Show Notes Transcript

Short Byte: Tim Olshansky - Managing hybrid remote teams

We can't put the remote genie back in the bottle, but with some people desperate to get out and go back to the office, how can organizations manage the two?

In today's Short Byte, I speak to Tim Olshansky, EVP of Product, Design and Engineering at Zenput, a foodtech startup focused on food safety. Tim embraced a hybrid remote model long before the pandemic and has been successfully managing hybrid remote teams for 11 years.

In this chat, hear Tim talk about his remote first but office-centered approach to remote work, and the three driving principles that make sure employees are happy, productive, and enjoy similar experiences, whether they're in the office or across the country or world.

Peter Bell:

Hi there, my name is Peter Bell. And today I'm speaking with Tim Olshansky, EVP of Product Design and Engineering at Zenput. Tim, thanks so much for taking the time to join today.

Tim Olshansky:

No problem. Thanks for having me, Peter, big fan.

Peter Bell:

Thank you. Likewise, it was fascinating talking to you just a few minutes earlier, where you introduced this idea. Everyone's trying to figure out what to do, as the pandemic becomes a little less of an issue, at least in, you know, kind of the first-world US places like that. And we're seeing that, clearly, we can't put the remote genie back into the bottle. We're not going to go back to a world where every single person has to be in the office five days a week, it's not gonna happen. But equally, there are people who are like desperate to get out of their homes and to interact with human beings again, who liked the water cooler talk. So we have to manage the two. And as somebody who's been building remote teams for years, remote, I'm like, it's fine. Here's the 17 things you need to do. It's easy. Hybrid terrifies me, because I have no idea how you manage the balance and the power dynamics. But you're describing that you actually had a model, even before the pandemic, that you call hybrid remote? Could you give me just a little bit of a sense as to what that's about?

Tim Olshansky:

Absolutely. Yeah. So, and for maybe a little bit of context, from me, I've probably been doing hybrid remote for the last 11 years, in some fashion, maybe somewhat successfully, somewhat unsuccessfully. And the things that I've learned and the things that we're doing now, currently, at Zenput, I think, work quite well and should hopefully work quite well when the world somewhat gets back to normal. But I think we consider it or I consider it a remote-first, but office-centered, call it, you know, culture or approach to remote. So, you know, there's there's kind of three guiding principles to how we do things around that. And I found that that's actually quite a good set of basic, call it, driving principles to help approach it. So the first is leveling the playing field. And making it super, super, consistent for each person in their respective locations, whether they're in an office, or in a home office, to basically have the same but not identical experiences. And I'm happy to talk more about that. So that's one element. The second is about being very intentional, and being very clear about how you do things, right? So being structured. And I think that's generally good practice when it comes to any sort of remote, even remote-first approach. And then the third is not forgetting that we are still people, and people, even the biggest introverts still like to spend time with people. And it's important to ensure that people still have an opportunity to connect with one another, even if they're mostly remote, in an office, but in an office two days a week, whatever it happens to be. And so keeping those things alive, putting that at the center of how you approach management, how you approach your office culture, and non-office culture, right, the home office culture, is super important.

Peter Bell:

That makes a bunch of sense. So I'd love to, let's dig into those one at a time. So you talk about the same but not identical, and that I think has always been one of my biggest issues. Like I remember building a large remote-first team for a company but realizing that I probably had no capacity to get promoted beyond senior director because I wasn't in the same room as the boss, right? And there was just this, it was an HQ centered company where I happen to have built this remote first appendage. So how the same can you make it and how not identical is okay?

Tim Olshansky:

Yeah. So I think it is an extreme where you create an environment where people are not allowed to socialize, right? Taken to an extreme, right, that you can go that far. And I've actually heard of organizations that are doing exactly that, where they have an office, and they have a large number of remote employees, and they're very clear that those office employees should not go to happy hours together and should not do these kinds of things that you would expect of people being in the same place, which is insane, right? That to me, that's it's just utterly insane, for a number of reasons, which, you know, we could probably spend the next 45 minutes talking about but that's, that's one extreme. The other extreme is what you're describing, right? You've got people who are remote, feel completely left out, they have no idea what's going on, they can't get promoted and whatever else. And that's obviously not the extreme that anybody wants to, to go down, right? And neither extreme works. And I think the sweet spot is making it clear how those things work to everybody upfront, right? So everybody can choose what they want. And I'll give you some examples. Right, so, taking promotions, and I think that's often a topic that comes up when people think about remote, in company cultures where everything's office-centric, where a manager is sort of the sole arbitrary decider of a promotion, or a senior manager, I should say. And they, you know, basically make their judgments on fairly subjective elements, like how many times did we go get a drink or a coffee throughout the day? And how much do I like this person, right? Definitely, an absence of face time is going to hurt and hinder one's career progression. However, if you're intentional about your company culture, if you're very intentional about how these things work, then the promotion process should be something that everybody understands upfront. The measures around it should be very clear. Expectations are set at the beginning, right? Beginning of the quarter, beginning of the half year or year, whatever the cycle is, that the frameworks around how a promotion gets, you know, decided upon, which includes like a career leveling type framework, or OKRs, and a combination of individual goals and all those other things that go into the consideration, are made known up front. There's a playbook around it. There's key rituals that happen on an appropriate cadence quarterly, semi annually, annually. And that's what you focus promotions around. Right? You don't, it's it's hard to separate the subjective pieces, of course, we are likely to want to promote people that we like, and not promote people that we actively dislike. But that's, I hope, a rare occurrence in a company with just like a decent group of people who are not so fixated by those subjective measures of career progression. And I think management is one of those areas where colocation around the kind of common manager or the more senior manager is still being figured out. I think, promoting individual contributors, in a remote, even a hybrid remote environment is typically a lot easier to do because the measures can be a little bit more clear, right? Anyway, so that's, that's an example. I can keep going. But getting clear, documenting, having clear expectations up front, making decisions, not based on subjective things that involve a group of people who are not just in one place, sort of eliminates that challenge, right? Going down the like socialization path, right? Like, how do you ensure that people have a somewhat common experience and that, that can be acknowledging that if you have remote folks and an office, as well, that you bring the remote folks to that office, that you try to build those connections in person. Of course, you can't bring them as frequently because who wants to be on a plane every week. But at the same time, you can go out of your way, as an organization to invest in bringing people together. And those are some flavors of things that you can do that create a same experience, but not an identical experience.

Peter Bell:

So that makes a lot of sense. And I think a lot of this is really an extension of the remote first principles, the things you get for free in an office-centric culture, you have to work for in a remote-first culture and specifically schedule water cooler time and things like that. So again, to dive even a little more into the same but not identical, like, what might be a conversation you'd have with an IC, would this be like almost an onboarding conversation like, congratulations, you're an individual contributor in this org. You can never come into the office, come in once a quarter, come in twice a week, or come in every day? What would be some of the things you would say to them? Now, here's the trade off: if you're never in the office, X, if you're in five days a week, Y?

Tim Olshansky:

Yeah. So, there's a couple of things. One, we've published our, kind of, principles around this, and what the trade offs people are making. And we make that front and center for everybody. So they understand what they're getting themselves into. Think right now, and I've done that in the past. Right now, it's an interesting time, because nobody is really yet in an office. And so we're making a lot of assumptions about how things will be in the future. But in all honesty, I expect things will revert back to how they were pretty quickly for us, once things kind of open back up. Now, to more directly answer your question around the conversation that's had, for us, it's usually at recruiting time, actually, before somebody even starts. And I think that's really important because you don't want to join a new organization with one set of expectations, to then show up on the first day and be told all these things, right? And so that typically happens. I think the best time for those conversations to be occurring is before somebody joins the organization, not once they join the organization.

Peter Bell:

Surprise!

Tim Olshansky:

Surprise, right? It's, I think, everybody likes to know what they're walking into. No one wants to walk into a company that turns out to be a disaster after they started. So, for example, for us, you know, for folks who we actively recruit who are not next to an office and example, we have three office locations, or we'll have three office locations. There's, there's a conversation that happens during the recruiting process around what they might experience not being in an office. That's usually common. That's often a conversation I'm having, sometimes the hiring manager, sometimes the recruiter, but it usually translates to, effectively one of three things, right? If we're hiring you, you're not at an office, then we ask you, are you willing to travel, and would you be happy to come once a quarter? Right? And we have some things that we do around that, that people generally enjoy. And that's, I've never had anybody say no, at least not yet. So in kind of all of my history, I've never had anybody say no to that level of travel. The folks that are in an office or close to an office, we haven't, we haven't found anybody that is within 15 miles of an office who says that they absolutely do not want to come in.

Peter Bell:

Right.

Tim Olshansky:

Right. And so I think in that scenario, it's more of a work from anywhere type of mindset. And it's, "I'd like to come in at least once a week, because I want some of the social connection", more often than not, is like the sweet spot we're finding amongst all the folks that we've either hired or in the process of hiring is two to three days a week feels right. So I'd like to be able to come in two to three days a week. And this, there's a conversation that might happen where it's, you know, if you're coming in two to three days a week, that's fine, we just want you to stick to it. Because we're going to get office space, right? And the worst thing that happens to organizations that embrace the hybrid model, where with people can work from anywhere, is that they overbuy, or over rent or over lease, they get frustrated with how much you're spending on an office that's practically empty all the time. And then one of two things either happen: either the company says you must be in the office five days a week as a negative reaction, or they shut down the whole office and go full time remote. And so that's the conversation we have for those folks. So with the kind of dichotomy of someone in the office, and not at all in the office, we explain some of our guiding principles and the experiences that they'll have.

Peter Bell:

That makes sense. So a whole bunch of things come to mind. I'd love to hit some of the special cases. So one thing I'm fascinated by, do you think differently about managers or even directors versus ICs? For example, if I want to come in, let's say, as a manager, or a team lead, my entire team is based in one office, and I'm across the country. Do you do that? And if so, how do you make that work?

Tim Olshansky:

I have done that, we're not currently doing that. And I think the view I've developed over the last 10 or 11 years around this is that you generally don't want to do that. Because it has, there's sort of anti patterns that arise that are just not beneficial for a team or for an organization. So I think that if somebody is a manager of a whole team or department, and all of their people are in one place, that's probably a hire that shouldn't have been made. The company should have probably hired this person in that office location, because, again, unintentionally, unconsciously, conversations are going to be happening where the manager is not privy to or not a part of that won't happen well, right.

Peter Bell:

Yeah.

Tim Olshansky:

And, and so what we, what we're doing, and what I think is sort of the go forward model for us as well, is to hire intentionally with people spread out. And so that as a remote manager, if most of your team is also distributed, but they might be in an office, your management style doesn't have to change, it doesn't have to adjust, right? It's effectively the same as managing a fully remote team.

Peter Bell:

And I feel like there's some kind of cutoff point, like, let's say, you've got kind of a traditional team of like seven or eight employees, couple of them happen to be at HQ or a couple of them are in one office. That's fine, but there just needs to, it's like when five out of eight are in one location and you're not, that it becomes much, I mean, I did it once and I literally told the team, okay, firstly, I persuaded half of the in-office people not to come in again. I'm like "Look, who wants to commute? Wouldn't you like to live in France for a year?" Like, I was like, all this stuff.

Tim Olshansky:

Absolutely, yeah.

Peter Bell:

And then secondly, I'm like, okay, there are still three of you left in the office. You're not allowed to be in the same conference room for standup. You have to be one screen per person.

Tim Olshansky:

Exactly right.

Peter Bell:

Do you have any exceptions to that? Do you do standups where it's not one screen per person, where you just have like, five people in a room, and three people Zoomed in? And how do you make that work, so that again, there is at least some similarity in the experience?

Tim Olshansky:

Yeah, so something I've done in the past, and I think we will do in the future is, you have everybody, everybody who's in an office, have them in the same meeting room. Because open, I mean, open plan is the devil, right? And, so if everybody's on a call, and everybody's talking all the time, it becomes a nightmare. And so having everybody take standup at their desk, and everybody else around them is taking standup at their desk is painful. So still going into a meeting room, still going into a conference room, we have Zoom rooms, right, and all the conference equipment, but everybody still brings their laptop in and dials in and their video is on. And so you can see every individual's face as if they were at their desk. But there's just one common microphone, and one common speaker, and it kind of creates the noise barrier and everything from what's happening outside and makes sure, it makes everybody focused on what's happening in this meeting.

Peter Bell:

That makes a lot of sense. Have you run into any issues with that? Or do you find that generally works well, or any other enhancements people need to make?

Tim Olshansky:

Yeah, I think, first is Zoom preferences of not automatically connecting audio need to be, right, because, you know, how many times have we been on Zoom calls in the last 16 months? Like, "Can you hear me? Can you hear me?" There's the echo, there's the noise, right? So just, there's that, those kinds of things. It is a bit of a cultural shift. And people often forget that, you know, the intention here is to sort of level the playing field for the folks that aren't in the office. And so they, you know, because they're in a room, in a meeting room, they've got the people around them, you know, they look directly at people or they try to have side conversations. And so that's where there's a little bit of, you know, call it behavioral change, where you try to keep everybody looking at the camera, and make it feel the same.

Peter Bell:

Adding to that, so one of the things I find for standups that I found works pretty well. What do you do for like the brainstorming meetings and things like that? Where there's, there's the one executive, and he's like, "Wait, let me just draw it on the whiteboard". And nobody can get a good angle on it because there's like, glare of the light off of it? Do you move them to like Miro or MURAL or something like that? How do you think about that?

Tim Olshansky:

Bingo, yeah, we use MURAL. And so pre-pandemic we were using, basically, Google Draw, or I think it's diagrams.net now, where people would sort of draw collaboratively in the diagramming tool. Wasn't great. Tools like MURAL and Miro today, much better. And they work really effectively. We slap on another's hands anytime somebody tries to reach for a pin in a meeting or a brainstorming session so that they're not doing that. There are, I will say, though, that in the last 12 months, I have noticed a number of good tools pop up that allow you to draw on paper in front of you, hold it up to the camera, and it sort of automatically turns it digital.

Peter Bell:

Oh, interesting. Yeah.

Tim Olshansky:

And I think Google Jamboard is doing that. And I, there's another one that's front of mind, but I can't quite remember the name, that does something like that as well. So, you know, you basically create mini whiteboards for people. And so they can have the same tactile experience of drawing, which I think is, you know, it's easier to do that than to drag boxes around.

Peter Bell:

Yep.

Tim Olshansky:

And then that makes it something that everybody can see effectively.

Peter Bell:

Well, that makes sense. Um, another thing that often comes up, how broad a range of time zones are you working with? Is it pretty straightforward that you can just have standard overlap hours? Or do you do round the, you know, follow the sun? Like, how do you think about, especially feature development over time zones?

Tim Olshansky:

Yeah, great, great one, because I'm pretty passionate about time zones. In a prior life, I was responsible for teams basically 12 hours apart from one another, right? So there's eight different, eight different offices, and it was almost impossible to get people on the phone or have synchronous conversations when it was necessary without flying. And I don't ever want to do that again, and I don't think that that's healthy for the people on those teams, right? So one, one thing that we do is in both in the recruiting process, and again, in our sort of like approach to remote or hybrid remote, we're very explicit about time zones. So by and large, we try to keep a common timezone. And so we have, we have folks in Europe and Eastern Europe. We have folks in, on the east coast and we have folks on the west coast. And you know, we have people in the company in Asia, but broadly speaking on the kind of product design, engineering teams they're not that quite far out. So what we do is we align on a common time zone or a common, yeah, let's just pick pacific time, and we

say our time zone is 8:

30 to 5:30. And anybody who is, within three hours of Pacific Time, needs to align their day roughly 75% with that time zone. Right. And if you're more than three hours, so Europe is a prime example, 50% is the desired goal. So we hire folks who are willing to shift their schedules, and, you know, work into their evenings and make it work. And that's, that's worked well for us. And every, the people that we're hiring are fine with that and actually like that, so.

Peter Bell:

That makes perfect sense. Just to ask, would you ever go back to, "Hey, I'm going to add some people in India, some in Jakarta, some in Singapore"? Or do you feel like once you get beyond a certain point, it's just not what, you don't get an ROI in terms of the extra complexity you're bringing into managing the org?

Tim Olshansky:

Yeah, I think there's this like a four quadrant way to think about remote, right? There's synchronous, asynchronous, fully, fully distributed, and centralized, right. And I think depending on which of those four quadrants you feel you fit into, you can make those decisions around whether you, you know, hire diametrically opposed time zones or something else. I think for me, I, I would prefer to stick to the same rule, regardless of where people are in the world, so long as they're willing to align with that time. And I think that's the difficult part. So if you're hiring somebody in India, and they're trying to overlap with Pacific Time, 50, well, yeah, 50% that's rough, right? They're working

4:

30 in the morning, and-

Peter Bell:

Right.

Tim Olshansky:

You know, unlikely to happen. But I have, I will say that I have interviewed some folks who have been very adamant that that's what they want, and that's what they like. And for other reasons, it didn't work out. So they probably exist, but we haven't done that.

Peter Bell:

That makes sense. So we've been talking about intentional and structured, are there any other structures that you bring in? Like, how do you think about documenting conversations? And like, what's the tooling so that there is a shared understanding of what's being communicated, if you weren't in the room during a given conversation?

Tim Olshansky:

Yeah. So I would say that this is, this is generally good, best practice with, you know, entirely distributed teams or hybrid teams. Hell, I'd argue that it also makes sense for teams in an office as well, right? Just write everything down. It's really not that difficult in principle. But of course, there are reasons why people don't write things down. And I think they often stem from not knowing, you know, what should I write down? How much should I write down? What's the best structure for what, what should be included? Where do I put it? How do we find it? There's 100 questions that come up. And that tends to get in the way of people writing things down, not to mention that not everyone just likes to write. And not everyone's great at it. So we have a couple of different things that we do. So we use Confluence, which I don't think the tool necessarily matters, but you want one tool for all documentation. And I think that's, that's like the bare minimum that if every team is, you know, using their own tools, so you've got Google Docs, you've got Office 365, you've got Notion, you've got Confluence, you've got GitHub, you know, Pages, and whatever else. Like that's a recipe for disaster. So number one is only one place for all documentation. A sensible navigation structure. And this is like now getting into UX design, right, with information architecture, and things like that. But like something sensible, it doesn't have to be great, but just something everybody can follow along with, so everyone knows where to find it. Template, template template. Turn everything into a template, anytime somebody has to write something more than once. It's kind of like writing code, right? Sort of, don't repeat yourself, create a template, and have everybody follow it. For common things create some structure and rigor around it. So for example, we, we use a number of different things like product requirements documents, PRDs. We do technical design documents, we call them RFCs, right, which is, I think, a common pattern. Any major architectural decision, we record in an ADR, an architecture decision record. And so all of those things have a template. All of those things have a very easy way to get started. The template describes everything that should be included. There is a very clear playbook that's documented both in the template as placeholder text and sort of where that template is found, for people to follow. And honestly, like, I don't think I've heard anybody complain about writing documents beyond like, they don't feel like they're good writers. And so there's that piece. But things like that make it super simple. And yeah.

Peter Bell:

Now I've got to ask. So around that, one, the challenge I always run into is like, the first challenge is getting everyone to write things down and document it. And a lot of that is cultural, a lot of that is making it easy by having templates. And a lot of that is just like, well, where's the ADR, right? We require you to do this. The challenge I run into is, "Great, so we now have 17,400 ADRs, 12,000"- like, how do you actually map those in an intelligent way so when you're looking at screen 43 mocked up, you can determine how and where the ADRs are that relate to the decisions around the discount code logic and the automated location determining?

Tim Olshansky:

Absolutely, yeah, the the model I found there, and this is maybe why I'm, I'm a fan of Confluence, not not trying to shill any particular products, but.

Peter Bell:

Go Atlassian!

Tim Olshansky:

Go Atlassian, right. I'm Australian, I have to say that.

Peter Bell:

Yeah you're from Sydney, you have to.

Tim Olshansky:

Exactly. So one of the things I like about Confluence is they have the macros, the ability to create some structure out of the documentation. And I think that's important, right? So at a certain point documents need metadata to make it easy to find and for people to understand how things relate. And so that's something that we're doing, right, we include a lot of metadata in our documents, the templates themselves call out important metadata, at kind of the top that people need to fill out. It's overkill for where we are right now, it's not like we have 1000s of these things yet. But trying to see around the corner exactly, as you say, when you're trying to understand well, you know, why should, what should I find out about how this thing is supposed to work? You need that metadata to look it up. And so that's something that we do. Yeah.

Peter Bell:

That makes perfect sense. The last of the three points you talked about was to remember that people like being with other people. What are some of the cultural things you implement, or provide to make in a hybrid remote environment, to make people feel like they're connected and a part of the team?

Tim Olshansky:

Yeah. So there's the, maybe the standard get together that remote teams do anyway. And that is making sure that we get together on a quarterly basis, at a minimum. I think one of the things that we try to encourage, particularly managers, is to maybe do that a little bit more frequently. So if they have a group of people kind of reasonably close by, you know, if they're within, you know, a couple of hours drive of one another, you can do that maybe once a month, or something like that. So there's the in-person physical get togethers that are happening or will happen, again, that are very important, and a core part of our company culture, and a core part of company cultures I've been a part of have done this. So that's one. Two, allow the teams themselves to do things, so not try to drive everything top down. Because, you know, forced fun is no fun for anyone. And, and so the teams that create bonds will, will naturally do that. And that is okay and that should be encouraged, and in fact, supported with budget. And that could be a monthly kind of game night, or bi-weekly, fortnightly, whatever, whatever makes sense. Making sure that there is support from the organization, might not be a lot, might be 50 bucks, right? That can actually go quite, quite some distance to make that happen. And then there is the forced fun, that I think is, is still useful if it's genuine fun, not just like imposed upon everyone like some organizations might have done. So something we've done, I think that folks had a lot of fun around is a cooking challenge. We're a food-centered software company, so we work in food retail, food service, and so we had a great cooking challenge. And we have some chefs on the team, for sure. They're amazing. And so we turned it into a thing. We turned into a event. People got all kinds of goodies that they could use, and they didn't have to participate. But we made it something that people felt like they were a part of a company that was trying to do something and everyone had a lot of fun. So things like that, right?

Peter Bell:

Yeah, that that makes perfect sense. Unfortunately, we're running out of time, but maybe just one last thing that I see a lot of people struggling with. So, how, I'm gonna constrain this to within the US. So I understand that you can have different compensation probably for your Ukrainian or Belarusian team or Indian team versus the San Francisco team. Within the US, how do you think upon how you determine compensation as a function of location? Do you, is it just like San Francisco rates for everyone, San Francisco minus 15%? Or do you do it based upon cost of living, cost of labor? What thinking do you bring to that, that kind of debate?

Tim Olshansky:

Yeah. I I don't know that I necessarily believe that everybody gets paid exactly the same no matter where they are in the world because everybody's doing the same job. Because the truth is, there are different levels of performance to begin with, different levels of experience. And there are many things that happen, where if you pay people with the same title the exact same amount, but performance is uneven, you know, that things play out in negative ways. So I think from that perspective, I generally don't start from the premise of everybody who's doing the same job gets paid exactly the same, because that might be true if everybody's performing at the same level. But that's not, that's not how it happens. From a location perspective, same deal. I think San Francisco is the premium, right, rather than the, kind of, the standard. And so that's kind of how we look at it. There's, broadly speaking, a national average, and people get paid a premium who live in San Francisco because the cost of living is higher. And people who don't live in San Francisco get paid, I think, from what I can tell, at least based on how we've understood salaries and things like that in the market, get paid great, according to both the national average and the, and their local cost of living. So that's, that tends to be how it plays out. Now, when you think of it from a premium perspective, well, we're paying all these people so much more money in SF or New York or whatever the major Metro is, maybe we just won't hire anybody there because it's too expensive. And that does happen. I won't pretend otherwise. But we were intentional about offices so we want to ensure that we have people close by. And there are often skills that we need that we can only find in certain locations. And that's where we'll hire.

Peter Bell:

Tim, thank you so much for taking the time to talk today.

Tim Olshansky:

Thank you, Peter. Was a pleasure.