536: Managing a Hybrid Team | Hassan Osman

Podcast Cover Image: Managing a Hybrid Team Featuring Hassan Osman
Podcast Cover Image: Managing a Hybrid Team Featuring Hassan Osman

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Are hybrid work environments the future?

Let’s find out on this week’s episode as we chat with an expert, Hassan Osman, a virtual teams and project management thought leader. He is currently a PMO Director at Cisco Systems (views are his own and not those of Cisco), where he leads global virtual teams on delivering large and complex programs.

Before joining Cisco, he was a management consultant at Ernst & Young LLP, where he helped business leaders and executives at Fortune 500 companies run their programs more effectively.

He is the author of several #1 Amazon Bestselling books, including “Hybrid Work Management,” “lnfluencing Virtual Teams” and “Don’t Reply All.” Hassan has also conducted research at Harvard University related to virtual teams. He holds Master’s degrees in management from Carnegie Mellon University and Harvard University, and PMP, CSM, and lTlL certifications.

To learn more about Hassan’s writing on managing remote teams, visit www.thecouchmanager.com.

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Managing a Hybrid Team


George: This is the “Conquer Local” podcast, a show about billion-dollar sales leaders, marketers leading local economic growth, and entrepreneurs that have created their dream organizations. They wanna share their secrets, giving you the distilled version of their extraordinary feats. Our hope is with the tangible takeaways from each episode, you can rewire, rework and reimagine your business. I’m George Leith, and on this episode, we welcome Hassan Osman. Hassan leads virtual teams in delivering large and complex programs for strategic customers in the Americas region. He also did research at Harvard University related to virtual teams, and he holds a master’s degree in management from Carnegie Mellon and Harvard. Prior to working at Cisco, he was a management consultant at Ernst and Young, where he helped business leaders and executives at fortune 500 companies run their programs more effectively. Hassan is the author of Amazon bestselling books about team management, and his latest book, “Hybrid Work Management: How To Manage A Hybrid Team in the New Workplace” is due out soon. “Influencing Virtual Teams”, “Don’t Reply All”, “Effective Delegation of Authority”, “Project Kickoff”, “Write Your Book on the Side” and a bunch of other great books have been written by this prolific author. We’re going to be speaking to Hassan Osman, our guest this week on the “Conquer Local” podcast when we return.

George: Welcoming Hassan Osman on the show this week. Hassan, welcome to the “Conquer Local” podcast.

Hassan: Hey George, thanks so much for having me.

George: Well, we’re excited to learn about all of the great content that you’ve been producing. It’s interesting, your hobby is writing these actionable books and it’s different than your day job. So maybe we should talk a little bit about that because I did mention your day job in the intro. So maybe we could talk about that and your book writing that you’re doing.

Hassan: Yeah, absolutely. So my day job is a PMO or Program Management Office director at Cisco systems, where I lead a team of senior program managers on delivering complex IT programs. And one thing George, I always want to mention is that views are my own and not those of Cisco. So I always wanna be clear that I’m not representing my company here, but as you kindly mentioned, yes, my hobby is writing books on the side. Drives my wife crazy sometimes, but to me, it’s this therapeutic time that I spend sitting down and writing. I absolutely love teaching. I absolutely love putting together my thoughts on paper.

George: Well, and how did you stumble into writing eight books? When the first book came out, what happened that led you to stepping into being an author?

Hassan: Yeah, great question. It’s hard for me to remember. This was back in like 2014. I think it stems from the love of teaching what I know and trying to simplify concepts that I learned in my day-to-day job as a manager. And I think my focus being writing short books for busy managers was sort of scratching my own itch. So I love reading books, I’m a voracious reader, but I don’t have time to spend reading four or 500 pages just to get the 50 pages worth of meat. So I decided to, hey, why don’t I start writing short books that I like to read and that have helped me in terms of their content?

George: Well, I’m always excited to find content that is too long, didn’t read is what it sounds like. This is TLDR. You’re like let’s get right to the action. The email etiquette… I gotta bring this up at the beginning because we’re writing more emails than ever. Some of them are being read, some of them were not being read, and you’ve got a very interesting take on email etiquette in your “Don’t Reply All” book. Can we start with that?

Hassan: Yeah, absolutely. So “Don’t Reply All” is a book with a collection of 18 email tactics that really help everyone write better emails to improve communication within their team. So if you are in a corporation and you work with three or more team members via email, then this is really going to help you improve the quality of the emails that you write. And you mentioned TLDR, that’s one of the tips in the book. Write emails that are five sentences or less. And one of my pet peeves is 17 paragraphs with a call to action in paragraph 12 buried somewhere with a question or something you need from someone. So really trending towards going for fewer sentences in your emails, because people don’t have time to read. They only scan emails these days.

George: I was in a debate yesterday with a colleague around this. I’d love to get your take on this then. When I’ve made or built a relationship with somebody and we’re working actively on a project, do I really need to write an introduction, have a beautiful body in there or is it okay that I just get right to the point because I’ve already established the relationship? What’s your take on that?

Hassan: Yeah, definitely the latter George. I would say get right to the point. I think every recipient is gonna thank you for it. It’s not gonna waste their time guessing what exactly is the point of your email, and it just minimizes the back and forth. So one of the things I actually mentioned in the book is this concept of three Ws. So if you work in a team and you need to assign tasks to someone, you’re a project manager, then focus on the three Ws, the who, the what and the when. So who do you need to do something, a specific person? What is it that you want, and when do you need it by? So very simple and a clear bullet point and you’re gonna get some really great, cool points from your recipients and your team.

George: We mentioned in the intro about the nine books and we wanna specifically talk about book number nine, which thank you for sending the manuscript through. I had to read through it. It’s great. “Hybrid Work Management: How to Manage a Hybrid Team in the New Workplace”. And we’re gonna spend a lot of time on that. And I’d love to hear from you at a high level, what’s the book all about?

Hassan: Yeah. So post COVID, nearly every organization, got a taste of what remote work feels like and they wanted to return back to the office, but every organization realized that, well, it’s probably not gonna go back to pre-COVID times where everyone’s in the office from 9:00 to 6:00. And so the world shifted to a hybrid work model where it’s a combination of working on-site and remotely. And the book is basically about how do you transition into that and how do you manage a hybrid team in this new workplace. In this new way of working, because it is still foreign to a lot of organizations.

George: And it continues to come up. When I’m working with organizations they’re talking about in their quarterly business reviews, it’s still one of their major challenges. So we’re a long way from figuring this out. And I find it in any of the companies that I’m working with today, that management of the hybrid team is a really important component. Now in that, what you call phase three, managing the hybrid team, you’ve come up with some tactics and some concepts to help with this very important component. So let’s unpack those.

Hassan: Absolutely. And just to clarify, it’s a four-step process. So it’s analyze, plan, manage and evaluate. So it’s a simple framework to manage your hybrid team and then with step three, which is to manage your team, there’s a lot that goes on there because that’s where you’re gonna spend most of your time in terms of managing and leading your hybrid team. And there is a few tips that are gonna help you out. One is top of mind to manage fairly and avoid what’s called the two-tier system. So the top priority George of a hybrid leader is really to make sure that all employees are treated fairly. And what I mean by that is that hybrid models could create a two-tier system of first-class versus second-class employees. In other words, two different employee experiences where those who spend more time in the office are treated as first class and those who spend more time remotely as second class, and those might feel left out or that they’re missing out on opportunities. So you wanna make sure that you avoid that potential leadership bias and favoritism by constantly emphasizing inclusion. And this is sort of a recurring point in the hybrid work management field is to make sure that fairness is front and center while you’re managing your team.

George: It’s funny when you look at the data, sometimes I’ve found organizations have been saying, Hey, we’ve been doing this remote thing or maybe doing a hybrid thing for the last two and a half years, three years, and it seems like all the remote people leave and I’m like, it’s a self-fulfilling prophecy. You haven’t set up a system for them to feel included on the calls so now they’re just talking head that usually doesn’t get a chance to participate. So you’re calling this out and thank you for doing that because I find a lot of times when people go, yeah remote doesn’t work, hybrid doesn’t work, they just end up leaving. It’s like, it’s the way you set it up.

Hassan: Absolutely. It’s really in the details. And you wanna make sure that the mechanism and the planning of a hybrid work arrangement has to factor in taking care of your employees and really understanding or setting the guidelines of what does work-life balance actually mean. And building that culture, which can be really, really tough.

George: And how do you position tracking so that it’s not big brother? I know our CEO said, you gotta have camera on when COVID hit. During Google Meet, you gotta have a camera on. That was the policy. And we work with lots of companies and there’s one company, in particular, we’re working with right now, they never have their camera on. And because those two cultures don’t line up, how do you know what’s being done on the other side? How could you can’t see it? So do you have any tips on that?

Hassan: Yeah. I mean, listen, video can be a double-edged sword, so on the one hand, it’s good because it builds a little bit more intimacy and cohesion because you get to pick up on facial expressions and you get to see what someone’s actually saying or thinking maybe if they’re not talking, on the other hand, we went through a phase of what’s called video fatigue. So meaning people are just behind their desks for hours on time and feeling like they have to put on a face and just constantly concentrating on their screen, which could lead to burnout. So there is a fine balance, and one way to kind of counterbalance that negative effect is to say, well, a staff call every week let’s have video on every other week. So kind of spread it out a little bit where you might have a walking meeting maybe on the days where its video can be turned off and that could incentivize a little bit of the exercise aspect of things. But the key, George, is to make sure that you have a conscious hybrid work policy in place, meaning you can’t just leave it up to well, we’ll see how it goes or what the norm is, and just gravitate towards that. Set it up, have the feedback from your employees, understand what their needs are and define it. Kind of put it that there and say, Hey, video can maybe be turned on for the first 15 or 20 minutes of one hour call, and then unless you’re presenting, you don’t need to have it on. I mean, there’s so much work you can do with that as long as you have it documented somewhere and posted.

George: I was reading through your manuscript and also I’ve been experiencing hybrid and it’s kind of one of those things that everybody’s experiencing this, we all have our opinions and some people’s opinion are I wanna work remote because it’s easier. I wanna work remote because I can communicate with people all over the world and I don’t have the commute and they really see it as being easier. But in order to truly do hybrid, when I read through your book, it talks about you’ve gotta put the effort in to over communicate. To me that doesn’t seem easier because if I’m right in a room with somebody, I just walk over, punch them in the shoulder, then we dig into the thing we’re discussing. So now you’re saying if we wanna be effective with this, we have to over communicate, but there’s a huge risk if you don’t do that. I understand.

Hassan: Absolutely. The challenges that with remote employees, they tend to be very siloed in nature where everyone is working on their own thing and this transactional feature easily leads to isolationism. So this whole out of sight out of mind think kicks in. And what happens is that managers who are on site with other employees, usually have more information about what those employees are working on because to your point, they can just walk over, they bump into each other in the water cooler or the hallway, and so what you wanna do as a manager and a leader is to keep track of what your team is working on and over-communicate with them for extra visibility. So you don’t want your team, especially your remote team, to feel like they’re in the dark. So checking in with them frequently, by over-communicating with them about what they’re doing is important so that they feel as supported as other onsite team members.

George: And I wanna reiterate something that I hope people are getting, this isn’t just in your own company. This is, if we’re working with a prospect or a customer, you gotta get good at this stuff because it’s not going away. There will be customers, of course, CFOs are loving this because there’s not as much travel, we got less people on planes, we’re saving money, but it also is you gotta meet your customer where they are. And there may be organizations that you just can’t get in the same room with, or maybe you can once, but you’ve gotta drive a project forward and that’s all gonna happen online. So I think that there was a catalyst when we had COVID, everybody had to get used to this thing. Some people think they can go back to the way that it used to be, but it’s never gonna go back to where it’s all face to face. Things are just moving forward. So now I’d love to talk about how to run a hybrid meeting effectively because you’ve got this nailed down in the manuscript, in the upcoming book, and everybody is struggling with this. So if you would be so kind, what are your four tips on how to run hybrid meetings effectively?

Hassan: Yeah, absolutely. So one of the main activities that you’ll spend a lot of time on when managing your hybrid team is meetings, of course. So a few tips that will help you out, the first is to conduct all meetings online. And what I mean by that is that all team meetings should be conducted as if everyone is remote, including your onsite employees. And this is in line with a concept called remote first where you default to remote on everything. So asking everyone to turn on cameras really helps. I know we just talked about that, so you kind of think about the balance there, but if you have a conference room, if you have a large team and you’re in a conference room with 15 people and then 30 other people have dialed in, then it’s also a good idea to share the video feed of your remote participants on the conference room screen to make them all feel like everyone’s connected. So that’s one tip there. Another idea behind conducting meetings online is to mix up your breakout groups. So a lot of times, especially with training, for example, and you need to have breakout sessions for brainstorming the tendency is to have groups in the office huddled together, and those who are remote huddled together as well. And while that might make sense from a logistics standpoint, you want to think about inclusion by mixing up both groups. So maybe you have a couple of folks who are remote, a couple who are in the office kind of conduct their own breakout session to mix it up a little bit. So that’s one of the tips, conducting all meetings online. Another is to batch your meetings. So what you wanna do is schedule meetings that require face-to-face coordination on the same day or two in the office. And the goal here is to maximize the benefits of the team being together in the office for your meetings. So one thing that’s kind of tongue in cheek is that you don’t want someone to drive and commute all the way into the office and spend the day on WebEx or Zoom. That’s not really a hybrid model of work. That’s just forcing people to the office for the sake of forcing them. So by scheduling maybe weekly or biweekly, even open office hours with options of onsite and online, you can use those for non-urgent interruptions and then kind of build that relationship with people. So I’m a big fan, George, of having one-on-one discussions in person, if possible, because that’s where you get the maximum return on investment of your hybrid model.

George: No, and those are great insights, Hassan, on just basic little things that could make people feel a lot more close to the organization. And you’ve got a great idea around including team building. Why stop doing team building?

Hassan: Yeah, exactly. I mean, I think I’m a big fan of team building. I know even pre-COVID organizations used to spend hundreds of thousands of dollars on team-building activities, offsite excursions, things that bring the team together and make them collaborate and coordinate a lot more effectively, and most importantly, build trust. And those informal interactions in the office, including drop-in and water cooler conversations, used to lead to higher cohesion and intimacy and we lost a lot of that during COVID because everyone was remote and it was very transactional. So you want to focus on those team-building activities by creating dedicated sort of fun outings or what have you that enable those moments of engagement to develop relationships. And you can do this online or offline. So it works in a hybrid model. So offline, keep doing team excursions, make sure that when everyone comes into the office, have those free pizza lunches, maybe do some community giving or volunteering or maybe escape rooms and team challenges. And then with online, when you’ve got long stretches of time, where everyone’s sort of remote, maybe come up with trivia or charades games or virtual coffee breaks, which are like 15-minute check-ins every other day, and you can come in and talk about the latest Netflix movie that you will watch, anything unrelated to work. So anything like that, George, I’m a big fan of, because it actually does link to increasing productivity at work.

George: No, I love that. We just recently acquired the Calendar Hero organization a few months back and they had a virtual water cooler event once a week where you couldn’t talk about business. It was all about what was going on in your life, that water cooler discussion that you would have that usually doesn’t talk about the project. You have one warning that I wanna make sure that I don’t miss in your tips, and that is be aware of those offline meetings that are happening. And if you didn’t include it, there’s a big risk there, isn’t there?

Hassan: Yeah. I’m glad you brought that up. So what happens is that important decisions are sometimes made in the office without the input or approval of remote team members. And so what you wanna do is you want to set guidelines and protocols that help keep remote employees informed and included in offline decisions. And one simple way to do that is to use a common tool for documenting and approving decisions. So what you don’t want to have is John and Mary bump into each other in the hallway and say, Hey, you remember that thing? What we talked about, let’s just move forward with option B, and they leave the remote team members uninformed. Whereas if you have a centralized common tool for documenting and approving those decisions, it doesn’t have to be anything fancy. It could be any even just group chat system. Then by forcing that you’re defaulting to a remote-first culture, which helps with offline decisions and moving them to online ones.

George: No, I love that. And I’ve been involved in organizations that didn’t use a decision log and you’re right, it can be a very simple process. And even if you’re not doing remotely, I’m just, even if you’re making any decision, just to know we made this decision on this day, at this time, with these people present, just having that can be very, very powerful. But what you’re highlighting is one of the big struggles of remote, is that meeting after the meeting that happened in the hallway and they made a decision and the rest of the people feel left out and that that’s really gonna hurt that hybrid model. So we went through the two steps around phase three in your plan of managing your hybrid team. But I always like to give the guest the last word, what of all the analysis you’ve done when you’re putting together the book and getting this thing ready to release, is there any silver bullet out there that you’re just like, this is one thing you just have to do.

Hassan: Yes. I love that question. And here is a takeaway. It’s not so much what to do, but what to think. No one has figured this out yet. And so you have to think about an iterative process, meaning you’re not gonna get this right the first time around, you’re gonna have to analyze this, you’re gonna plan for it, you’re gonna manage it, then you’re gonna evaluate. So you’re gonna think through whether this worked or not, but then after you evaluate, you go back, you reiterate the process and go back to analyzing because you’re not gonna get this right the first time, everyone’s still learning, and no one has a silver bullet as of this date.

George: And is it fair to say, Hassan, that the reason nobody’s got a silver bullet is every situation is a little bit different?

Hassan: Absolutely. I think there’s even within the same organization, there is no one size fits all. There’s no way that you’re gonna have team A follow exactly the same protocol as team B because they have different needs and they have different customer needs. So you have to balance all of that.

George: And we have our internal teams, everybody operates a little bit different. If we can get to some level of commonality, that would be cool, but to just know that no one has this figured out, constantly iterating, we’re all trying to get it right, and then it’s gonna be different. That actually helps my anxiety when it comes to the hybrid B2B because we’re not alone. Everybody is in the middle of figuring that out. And your analysis has shown that. So thanks for sharing that, Hassan. We really appreciate your learnings that you’ve brought to us. And if people wanna reach out to you and you have the business work that you’re doing, we talked about that off the top, but if they want to consume this hobby that’s driving your wife nuts, but is very, very valuable. How can they get more Hassan Osman?

Hassan: Thanks for asking, George. So it’s thecouchmanager.com, all one word. This is my blog where I write about management topics. My books are listed there. I’m on social media. My LinkedIn links are there. My email’s there. So simply go to thecouchmanager.com and I’d be super interested in connecting with you.

George: Excellent. And our team’s gonna put that link into the show notes so that everybody can get connected with you and then also follow you on LinkedIn and just start to learn more about the great material that you’ve been producing. Hassan, thanks for sharing with us today on the “Conquer Local” podcast.

Hassan: Thank you so much. I really enjoyed this.


George: One of the biggest struggles that all of us are facing right now is this new hybrid, remote, live, and what it all means and how to do it better. And it’s great hearing from an expert like Hassan, that this is an iterative process that no one’s figured out yet. That actually makes me feel better because sometimes you’re sitting there going well, how the heck do we make this work? And some great takeaways from the episode, this gent, he is super sharp, writing these short books for busy managers. I’m like, I wish more people would do this. TLDR, too long, didn’t read, get me right to the meat. And if you ever read through one of these pieces of pros, you’re gonna find that Hassan cuts to the chase. And I love that. There’s two sides of the coin when it comes to virtual meetings, building that intimacy and cohesion virtually is a bit of an art. We gotta learn how to do it. And remember there’s video fatigue. And I don’t mean on a Netflix and chill for two days of the weekend. I’m talking about when you’re at work and you’re on Zoom meetings over and over and over again, it wears you out. It wears you down and it’s leading to that burnout and we’re not having effective meetings. And then what happens is our remote workers start to not feel included. They start to miss out on the decision-making process. They feel like second-class citizens in your organization, and that’s not gonna work out when we’re building a team and we wanna have that team to be cohesive. If you take a remote-first approach, according to Hassan, to all meetings, then the remote workers will feel included. And the other thing that I’ve found to be really effective and I get to do this because I’m on the road. So I’m that remote individual on a lot of calls, come back and communicate to the team in the boardroom and say, Hey, have you ever dialed into one of our meetings and see how horrible it is for the remote people and just get them reminded that there’s a whole bunch of other people there that need to feel like they’re a part of the process and of these steps that Hassan has outlined in his four-phase approach when it comes to managing the hybrid team, a lot of it is around how do you conduct those meetings effectively? And I love the idea of the offline decision-making. You gotta be aware that those things happen and how do we loop everybody in to make them feel like they’re a part of that decision-making process. If you liked Hassan’s episode discussing managing a hybrid team, let’s continue this conversation. Check out episode 333, Onboarding a Remote Workforce with my good friend Tricia Score who leads all of Microsoft’s business sales in the Scandinavian countries. Or episode 407, 10 Tips for Remote Selling with the master sales training series. Please subscribe and leave us a review. And thanks for joining us this week on the “Conquer Local” podcast. My name is George Leith. I’ll see you when I see you.

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