Spencer O’Leary of ActiveOps: Five Things You Need To Know To Successfully Manage a Remote Team

Enabling decision making & execution — I drive myself and my team to make decisions, make mistakes, fail fast, learn, and move on. But to act in this way requires confidence, and in operations management confidence is often influenced by the level of certainty of an outcome.

As a part of our series about the five things you need to successfully manage a remote team, I had the pleasure of interviewing Spencer O’Leary, CEO of ActiveOps North America.

Spencer has a background in operations management in the UK banking sector, and 20 years’ experience in sales — particularly the sales of workforce management and employee productivity monitoring solutions, where Spencer has developed a track record of sustained results achieved through the creation of sales cultures and capabilities that drive significant growth. Spencer joined ActiveOps in 2012 as Head of UK Sales, with responsibility for managing and expanding the UK sales team. After assuming additional responsibility for sales in South Africa and India, he was promoted to Head of Global Sales in 2017. Spencer relocated to the USA in 2020 and is now responsible for ActiveOps’ operations across the North America region.

Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit better. What is your backstory?

When I left school, I decided that a career in banking would get me the best paid job — I was wrong! I worked for Barclays in the UK in a local branch, but before long I moved to a mortgage processing center. I quickly progressed to management, first of a call center, then of a document image and workflow unit. That was my first introduction to IT, and to Filenet, Ross Perot’s workflow engine — and my first trip to the US! At the age of 21 I presented to over 1,000 people at FileNet’s annual conference at the Disneyland hotel in LA! My presentation was about tech and its effect on managing people. From that point on I knew I was going to work in IT — with a balance of tech and managing people!

Can you share the most interesting story that happened to you since you started your career?

One of the most interesting things is that I never wanted to be in sales! I joined a startup software company as a consultant, having just implemented their system in Mortgage Servicing at Barclays. It was a system that provided work and time data to allow managers to better manage. I worked with clients across the world implementing the solution, until one day the sales exec (one of three owners) left the business unexpectedly. The other two owners called me in and said, “we hope you can sell!” 25 years later, I hope I still can!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

In my first management position I thought that if I told people to do something, it would be done. I also didn’t think I needed to explain myself — I thought my team should do as they were told without needing to understand why! Then I realized my team was made up of humans who all had feelings, ideas, reasons, personalities, and preferences — and they were all different. When I told people to do things, 9 times out of 10 those things either were not done or done poorly! I quickly learned that when I asked people to do something (rather than told them), explained what doing something well looked like, and explained why it was important to me, the company and to them, they did a great job! That valuable lesson has stuck with me — today I invest as much time explaining why something needs doing as what needs doing or how — if not more. And over the years that has helped me recruit, grow and develop highly capable teams.

What advice would you give to other business leaders to help their employees thrive and avoid burnout?

I do believe that a key part of helping employees thrive is to get your hiring strategy right. Many senior execs want to be the best person in the room — which leads some to recruit people who are less experienced or capable than themselves, or avoid recruiting people who are more experienced or capable than themselves — the effect is the same! I only recruit direct reports who are more experienced and capable than I am. They make my job easier, they make me more successful. I also recruit for behavior, preference and skills over proven capability. As long as you demonstrate the right attitude and have some basic fundamental skills (like the ability to learn!), you can achieve anything you put your mind to! Once you have recruited the right talent for a role, you should find that managing that talent — and so helping employees thrive and protecting them from burnout — becomes easier. Personally, I adopt a coaching management style where I provide people with clear goals, metric-based definitions of success, and complete ownership to deliver. I would also argue that leaders need to be actively watching for burnout in their people. Assume that everyone is at risk of burning out, and go from there. After the year we’ve had, you’re probably not far off the truth. Look for emails at odd hours — or no communication at all. Look for who’s quiet in group meetings. Don’t wait for productivity to fall before you act — that’s a consequence of burnout, not a cause! Any data you can gather than lets you spot burnt-out employees before they affect productivity is a must.

Ok, let’s jump to the core of our interview. Some companies have many years of experience with managing a remote team. Others have just started this, due to the COVID-19 pandemic. Can you tell us how many years of experience you have managing remote teams?

The financial services industry has been working with some remote team members for ever — either remote offices or people working from home. My first IT role in the 90s had some team members working from remote branches, or on the road, or from home on certain days. So I have been helping organizations manage dispersed workforces for over 25 years.

Managing a team remotely can be very different than managing a team that is in front of you. Can you articulate for our readers what the five main challenges are regarding managing a remote team? Can you give a story or example for each?

A key consideration in remote management is the manager themselves. One of the most important changes we have seen since pre-Covid times is where the manager is located. Managing some employees who are working from home isn’t anything new, but pre-Covid most of those managers would be office-based. The managers themselves are also now at home. As we enter a hybrid workforce model, businesses have people everywhere — managers might be managing from home or the office, and have team members at home, the office, another office — all moving between locations dependent on the day of the week. Remote management was hard pre-Covid, and it was harder during Covid, but at least during lockdown everyone was always at home. Hybrid management — without the right tools, processes, and data — is nearly impossible to get right!

My 5 key challenges for managing remotely are:

1. Understanding output — Whether you call it productivity, utilization, or something else, we’re talking about the rate at which people work. This has always been hard to manage, predominantly because it is hard to measure. If businesses can’t understand, in real-time (or at least intra-week) how much works gets done in how many hours, per member of the team, they are not in control of their production line. Imagine a supervisor of a car production plant not knowing how many cars they could produce in a day — it wouldn’t happen, but in the service industry managers often don’t know how many cases or tasks they can complete in a given number of hours. It’s difficult, the data requirements are complex, the math is challenging and the average manager’s ability to control and improve the situation is weak. And now, those managers have to do it all remotely. The key is to revisit the processes managers follow. ActiveOps teaches managers about capacity management, people management, and the link between the two — as well as providing data that helps managers get the insight necessary to make decisions while working remotely.
2. Protecting wellbeing — Workplace stress has always been on the radar for organizations. In the office, managers used their eyes and ears to sense issues early and hopefully intervene to keep employees healthy. Preventing (or at least reducing) workplace stress was hard, but possible. Managing remote workers, remotely, makes it 100 times harder to identify and remediate wellbeing issues. Managers can’t see or hear their team during the day, and have very few opportunities to pick up on body language on Zoom or Teams. Their interaction time is reduced, maybe 10 mins a day or 30 mins once a week. Their workplace stress prevention capability has been reduced — so their activity focuses on responding when something has gone wrong. In a world where moving jobs has never been easier, sickness and attrition caused by poor wellbeing has a real and significant cost to business. Having systems, metrics, processes in place to highlight early signs of poor wellbeing is critical for managers, and organizations as a whole.
3. Maintaining control — Humans like to feel in control. Pre-Covid managers had a degree of control over resources and workload, because they could observe what was happening in the office — did they enough resources today to get the work done? Did they have enough work in today to keep everyone productive? When everyone works remotely, there’s a risk that control starts to deteriorate. Managers can’t see their people, they can’t see the work, and they can’t hear the challenges the team faces. Instead of managing production, they just deal with service failure; instead of managing productivity, they report it after the event; and as we’ve said, instead of managing wellbeing, they resolve crises and problems after they arise. Without the right tools, managers can’t manage. They fire-fight, resolve, and fix — when they should be preventing, minimizing or avoiding. It’s a challenge for the manager of a team of 15 people — now imagine their boss, who manages 5 team managers and has the same challenge across 75 people. Or their boss who manages the business unit with 400 people in it, or their boss who manages the organizations function with 2,000 people, or their boss with responsibility for 20,000 people. The challenge, problems, and financial impact of a lack of control increase exponentially as you move up the organization. Mix that with multiple locations, geographies, time zones, currencies etc. and you can end up in a mess!
4. Enabling decision making & execution — I drive myself and my team to make decisions, make mistakes, fail fast, learn, and move on. But to act in this way requires confidence, and in operations management confidence is often influenced by the level of certainty of an outcome. If a manager does X will they get Y? If managers don’t have accurate, consistent and scalable data across their operation then how can they be confident of their ideal outcome? It’s like taking a paper map and planning a route to your destination — without knowing where you’re starting from! In a remote setting, all a manager’s traditional sources of confidence when making decisions disappear — as we’ve said, they can’t see their team, or their work, or the challenges that crop up. As a result, they end up making nervous decisions, or making decisions too soon, leaving their teams unsure of their direction and next steps.
5. Reducing attrition — Attrition is going to hit many US businesses hard. You have a perfect storm where employees want flexibility at work which their employer may not provide as time moves on; many employers don’t measure or manage performance & wellbeing, leading to an unfulfilling workplace for employees; lots of people are not going back to work because it doesn’t make financial sense; and more work is coming onshore as Asia and India struggle with Covid and home working. On top of that, it has never been easier to move jobs — you get the same chair, desk and office, and your new employer just ships you a new laptop! The problem is, staff turnover adds an extra complication to the already busy life of the remote manager. On top of everything else, they need to recruit, onboard, train and deliver capable, efficient, effective new recruits into their team — all remotely. New starters are less productive than their experienced predecessors, make more mistakes so increased checks are needed, and have variable performance — so now the manager’s control mechanism needs to be further calibrated to take this into account. Research from Achievers shows that 52% of employees are planning to look for a new job this year. Managers need a capacity and production management system to equip themselves to deliver the desired outcomes of the business.

Based on your experience, what can one do to address or redress each of those challenges?

In my experience, one of the trickiest parts of managing a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote.

On top of this, the most important thing an organization can do is to start gathering data that tells them about their workforce. Managers need new tools to manage in a remote setting; they need data to replace the insights they would have gained from looking at what was going on around them. Better still, that data needs to be aggregated and analyzed for them, so they can see insights that help them make better decisions about capacity, productivity, and wellbeing.

Can you give a few suggestions about how to best give constructive criticism to a remote employee?

In many ways we need to adopt the things we would do face to face. If you do the little things well, people will accept constructive criticism. Make sure you are both alone (on Zoom or Teams), not in a room with others. Make sure distractions are at a minimum (background noise, backdrop etc.) Make sure you have a good internet connection (there’s nothing worse than having to say difficult things twice because you can’t be heard!) Make sure cameras are on, and that you are looking into the camera as much as possible, and that the camera is at eye level — remote sessions can be impersonal, but in the same way as face to face, not looking at someone when you have a challenging conversation makes you lack credibility. The content of the conversation should be data-driven — meaning you need to have the tools to obtain and share that data! Quantitative conversations are always easier than qualitative conversations — they help you set measurable targets, define what goods looks like and then allow people to self-manage how they track towards it. Many managers do the opposite, and demand unclear expectations, make the assessment subjective and then provide feedback weeks or even months later — a missed opportunity!

Can you specifically address how to give constructive feedback over email? How do you prevent the email from sounding too critical or harsh?

Email is a hard medium as a written sentence can carry very different emotions depending on how the recipient chooses to interpret it! I always try and use email to book the call, not share the news. If email really is the only way (and I would argue that such situations should be incredibly rare after the year of Teams and Zoom that we’ve all had), then a regularly used technique is the good/bad/good news sandwich — sandwich the bad news between two good news messages. And just as with face-to-face conversations, keep things data-driven — quantify targets, keep feedback objective, and track progress.

Can you share any suggestions for teams who are used to working together on location but are forced to work remotely due to the pandemic. Are there potential obstacles one should avoid with a team that is just getting used to working remotely?

Set a clear rule book of how you are going to manage the team and how you want them to work together. For instance: in my online meetings I always ask people to please turn their camera on, we always start and end on time regardless of who is late, and we use the 5 minute rule: if people are late without prior warning or rescheduling, don’t just wait! We also use the ‘raise hand’ or chat functions if someone has a question or wants to say something. Beyond that, managers should work hard to involve everyone. Have more shorter meetings rather than long, once-a-week sessions. Have a regular non-work session — 15 mins around the virtual coffee machine — and make it fun. Team socials are possible remotely — think drinks, bingo, and storytelling — but it takes effort to make it happen. Finally, manage by example. Don’t be late, be organized, and allow children, pets, and things at home to affect your day — show you are human and struggle working remotely as well!

What do you suggest can be done to create a healthy and empowering work culture with a team that is remote and not physically together?

Give people ownership — allow different team members to manage meetings, delegate some activity to people — it demonstrates your trust in them and makes them feel important. Encourage people doing things for charity or balancing a busy work life with some corporate responsibility activity. Meet 121 with as many of your team members as you can — especially more junior team members. Take 30 mins and ask them what they think, how it is going, what else could the company do, etc. And then follow through; take action based on their feedback. Doing so makes the notion that their ideas matter a reality.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Thank you! If I could inspire a group of people to act differently it would be a movement in the education sector. I didn’t enjoy school and left as early as I could. Reflecting now I think it is because my teachers tried to teach me facts, rather than skills. Teachers have a unique opportunity to help our next generation learn how to learn — learn the skills to enable innovation, achieve the impossible and deliver outstanding results. Don’t focus on memorizing and recounting facts!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I have a lot of respect for Richard Branson, not because of any singular success, but because of the way he builds great teams of people who deliver outstanding results. One of my favorite quotes is: “respect is how to treat everyone, not just those you want to impress. Train people well enough so they can leave, treat them well enough that they don’t want to.” It encapsulates two of my core beliefs — firstly that treating people like you want to be treated is a free opportunity we all have, but for many it isn’t a behavior that is practiced. Secondly, many managers create a culture where employees feel trapped in their role — so they underperform compared to their potential. Give people the support, training and motivation to fulfil their potential — a few people might leave but most people will stay loyal and grow with the business. I always believe that people might join a great business, but often leave because of a poor manager!

Thank you for these great insights!