Remote Leadership

Published in

MatterScale Ventures

18 min readMay 13, 2020

(last version 4/27/2020)

It is highly likely that remote work -either working from home or working from nearby coworking locations- becomes prevalent after the Covid-19 pandemic. Having led and experienced a remote management culture for the last 15 years, I believe the challenge for firms will be migrating to remote leadership, not remote work. The reason for this is that while there are plenty of system tools and software available, and employees can adapt to a remote setup easily, with a few bumps, and at low cost, the real obstacle is that the CEO/C-Level will need to adapt and adopt a remote leadership culture, or everything else will fail.

Take something as simple as having a CRM. Companies with a CRM should have an easier path to become remote, while companies without it will suffer. CRM software implementations have been around for decades as they are relatively simple to use and understand, and yet studies show that over the last 13 years, between 30 to 60% of CRM implementations completely fail. Please stop and read this again. How can a company fail at implementing a tool like Salesforce, for example? It is basically an Excel file with more macros, and it registers customer information which should be important, and yet 30 to 60% of implementations fail? How? Data shows that the number one reason for failure is because the CEO did not put enough care and time into making it work.

If the CEO and all business unit leaders don’t adapt and adopt a remote culture, their companies’ efforts to migrate to remote work will fail. This guide is precisely about remote leadership, or how anyone with a position of leadership can shift their behavioral pattern to drive results.

Part I. Context: The Societal Benefits of Remote Work

Barring a catastrophe that forces mankind to stay at home forever, the main benefit of remote work is not the avoidance of infection. Rather, extensive adoption of remote work could become one of the most important and beneficial societal changes in a century. Remote work implies fewer commuting times for both remote and onsite workers. Those that can work remotely reduce their commute times to zero or close to zero (if they chose to work from a nearby coworking space), while those that cannot will also see a reduction in their commute time due to an overall reduction in road traffic at peak hours. The time gained can be significant for everyone, particularly in big cities where commute times tend to be longer. According to Geotab, 84% of New Yorkers have a daily commute (round trip) close to 90 minutes, which means they spend an entire month per year commuting. If an employee is suddenly given 12% more time, what would they use it for? Sleep, exercise, relax, or hobbies come to mind.

In addition to making cities flow better, remote work will have a beneficial impact on the environment. During the Covid-19 lockdown, social media is filled with images of “nature returning” and reduced smog levels, offering a glimpse of how clean life could be if we reduce emissions. While some of the social media posts are hyped and faked (dinosaurs in Central Park), there is no question that less road jams and less burned gasoline will reduce emissions. According to the Intergovernmental Panel on Climate Change 2018 report on Global Warming of 1.5°C, transport represents close to 23% of global emissions, and driving is responsible for ~70% of such emissions. A reduction of 10% in global driving, for example, could reduce global emissions by ~1.5%.

Working from home will also become a great detonator of gender parity. Under remote work conditions, women caring for infants may have a leveled playing field. If companies allow individuals to work from home or near from home without penalty, it would presumably allow mothers to stay in the workforce, get their promotions, and spend as many hours as needed to get the job done. The traditional “mom” role could have an important business meeting call while the “dad” role does the dishes, since there is ample evidence that men staying home spend more time helping in household chores. In households where both parents work from or near home, parenting responsibilities also become more evenly distributed, and the lower commute times discussed above imply more time for family activities, from time spent with kids, to parent-teacher meeting attendance, to the division of household chores. Last, it is possible that household income increases if both parents are able to find and stay at remote jobs.

It is expected that remote work implies significant cost savings for some firms by reducing their required office square footage. The savings depend, of course, on their current lease obligations, and to some extent part of the savings from the CRE lease should be transferred to the employees working from home or near-home, either to pay for the membership at a coworking space or to make certain modifications to the employee’s home, say, a new chair and desk, or support with cleaning services, or even the acquisition of a phone booth inside the house. Still, for service-based firms located in big cities, (factories and farms are not located inside big cities), it is expected that their savings from reducing their lease obligations will be significant. Data from The Square Foot, a startup that allows firms to find office space in the US, firms in New York spend an average of $14,000 per year per employee on rent. In Miami, the number is closer to $6,000 per year.

Given the benefits of migrating to remote work, it is more important than ever to do everything we can to help companies achieve effective migrations. Simple to follow guides can help managers and CEOs realize that with discipline and a few digital tools, remote work can improve productivity, results, and overall quality of life for millions.

Part II. The Role of the CEO & Business Unit Leader

“Time is the scarcest resource and unless it is managed, nothing else can be managed.” Peter F. Drucker.

Peter Drucker is considered the father of modern management, onsite or remote, period. He believed people become better leaders if they learn to manage oneself, then learn to manage a team, and finally learn to manage opportunities, in this strict order. Managing oneself refers to the efficient use of time and communication skills. Managing a team refers to the discipline of guiding a team towards a clear and strong mission statement with ambitious goals and aligned objectives. Finally, he believed that if one excels at managing time, communication, and a team, then managing opportunities would become a simple routine.

2.1 Learning to Manage Yourself: Time and Communication

You’ve won a ticket to have a live meeting with Bill Gates. You must choose if you’d rather exchange ideas with him via email or to have a face-to-face meeting while he is using a whiteboard. Which one would you choose? The same preference applies to individuals on your team who prefer to have a face-to-face meeting with you, rather than receiving an email. Communication is more effective when speaking in person, and less effective when written on an email. Given that this knowledge is so obvious, one must ask the question of why are CEOs then spending so much time sending emails.

The challenge with effective communication tools is that as they increase in effectiveness, they also increase the time required to execute them. Preparing and hosting a face-to-face meeting presumably takes significantly more time than sending an email. Bill Gates probably prefers to send you an email with some of his thoughts and a few links than spending an hour of his time preparing and hosting you in person. Scott Ambler, a former head at IBM Agile, illustrated the effectiveness of communication by channel, shown in Figure 1. A simple adaptation to Ambler’s chart, shown in Figure 2, shows that communication effectiveness and time required are positively correlated. CEOs send emails because it takes less of their time.

As this holds true in an onsite working setup, it is even more relevant in a remote setting. Distance favors emails while it kills face-to-face meetings. Efficient management in a remote setup, thus, requires a thought approach to time management and clear communication rules.

Figure 1: Communication Effectiveness and Richness

In Figure 1, effectiveness of communication refers to the power of different communication delivery methods, such as email vs face-to-face meetings. Richness of the channel refers to the interpersonal relationship: an email is cold, a face-to-face meeting is warm. Adapted from Scott Ambler, IBM Agile.

Figure 2: Communication Effectiveness and Time Constraints

In Figure 2, I adapt Ambler’s chart to include the time required to prepare and host the communication channel. An email can be written and sent in 20 seconds. A face-to-face whiteboard meeting takes time to prepare and deliver, if done well. Effectiveness of communication requires more time from the communicator.

“The most important thing in communication is to hear what isn’t being said.” Peter F. Drucker

2.2 Learning to Manage a Team: Defining Parameters and Providing Leeway

Ask any high performing employee about their preferred management setup and most likely their common response will be that they strive when the parameters of their role or domain are clearly set in stone, while at the same time, they are given plenty of leeway to execute any actions within their domain. People want to have clarity of expectations, clarity of the metrics that matter, and clarity about their career path, yet they also want to have the freedom to execute their work without anyone telling them what to do all the time.

In well-functioning organizations, leaders must merge their ability to set strict rules (expectations, definitions, and parameters) with their ability to provide autonomy and trust (independence to make your own decisions) to their team. In other words, effective leadership has to do with micromanaging parameters and macromanaging execution. The marching orders for a product manager should be, for example, to launch the product at the lowest price and with the highest customer satisfaction in less than 30 days (very clear parameter oversight), using whichever tools available and with feedback loops as needed (very loose execution oversight).

Choose any Management Framework As Long As It’s The OKR Framework

While I was responsible for the growth of Endeavor from 9 to 35 offices around the world, I decided to adopt the OKR framework to help us manage remotely. Our challenge was that we needed to make sure that every office and every employee would be fully aligned to the mission, would work towards the same goals, and would share a culture of results accountability, yet at the same time everyone had to feel and act with leeway and without constant oversight. The only way to achieve that was to have a simple to use framework that would make those goals and results transparent to the whole organization, encouraging recognition and nudging for everyone involved. OKRs (Objectives and Key Results) are precisely designed to keep existing teams aligned to common goals in a collaborative environment. While OKRs as a tool for startups or very small firms (by employee count) is less effective, I have no question that in a remote setup and for firms larger than 40 employees they become one of the most important tools for the effective management of teams. Between 2010 and 2018, Endeavor grew from 50 to 500 employees using OKRs. I struggle to understand how any firm will be able to manage remote work effectively without having an OKR framework, or at least something that looks extremely like it.

Like any solid management platform, OKRs forces a firm to clearly define its mission statement (where do we want to be in 5 years), to set ambitious goals to reach such a mission (what needs to be accomplished this year), to specify certain objectives that if reached will help meet the goals (what needs to be accomplished this quarter), to measure results to make sure the objectives and goals are being met (how do we know we are accomplishing anything), and to define which tasks are people and teams supposed to do be doing on a regular basis (what needs to be accomplished today).

Image source: Arnaud Meunier, What SpaceX Can Show Us About OKRs, Medium.

The OKR methodology covers the decision-making process for the leadership of an organization, yet it stays away from day-to-day tasks. A task -or set of tasks- is an action that a person must do in order to reach an objective. Except for complex operations such as operating a machine, employees don’t like anyone telling them how to perform tasks. They want leeway or freedom to perform them as they see best. Day to day on-the-ground actions produce significant knowledge that when used properly, build a knowledge center of best -and worst practices.

A full picture of effective team management should be emerging now. In order to shorten the span between the 30-thousand foot view (mission statement) with the actual work getting done at ground floor (tasks/to do’s), CEOs and business unit leaders need to set rules and parameters such as the mission, the goals, and the objectives with absolute clarity and accountability measurements (accountability implies goals and objectives need to have a clear owner). Yet CEOs should stay away from setting any parameter for task management. Once the objectives have owners, let those owners and their respective teams figure out which tasks require priority. In exchange for this freedom, task managers are then expected to create a knowledge platform that feeds leadership with valuable on-the-ground information.

For a good discussion about implementing OKRs, read Arnaud Meunier’s Medium post here.

2.3 Merging Time Management, Communication Skills, and OKRs:

The first priority of a CEO or business unit leader is to decide what needs to get done, by whom, and when it needs to happen. The second priority is to provide and encourage the dissemination of feedback based on measurable performance. Both priorities require strict time management and communication skills.

As a CEO, for example, you are in charge of coming up with a strong, ambitious, inspiring mission statement that rallies the troops and provides a clear path forward. This is no simple task, yet it is not something that gets done regularly. In fact, this is an action that should happen maybe once, and have revisions maybe once per year or so. So the “what” in this case is to set up a mission statement, the “who” is the CEO, and the “when” is once every 5 years with annual revisions.

The second priority is to provide and receive valuable and timely feedback to the team while enforcing the same from all supervisors. The pace of feedback sessions depends on the hierarchy and experience of the individuals. I believe the CEO should get a performance review once a year from the board, while the board should receive feedback from the CEO as well. C-Level executives should get a quarterly review from and to the CEO. Directors and associates will require and should benefit from more regular feedback, probably once per month. Table 1 summarizes these actions.

Table 1: Setting a Management Framework Optimizing Time and Communication Tools

Table 1: Starting at 30 thousand feet and all the way down to the ground floor, it shows what, by whom, when, and how things should get done. The “What” column refers to the rules or parameters set by leadership. The “Who” column refers to the main owner of the rule. The columns for “When and How” define the right time and delivery method for each action.

Part III. Onsite vs Remote Work

Onsite:

Table 2 shows an example of the physical places where management actions could normally take place. For example, setting up the annual goals gets done during a one or two daylong meeting at the office. Those goals get documented on a whiteboard. Quarterly meetings to review the goals or set the objectives take place at the meeting room in the office with a whiteboard and paper easel. The big paper sheets are then pasted all over the office. Monthly reviews of objectives and results take place at the same meeting room and documented in an Excel / PowerPoint presentation sent via email to everyone. Tasks get done at people’s workstations and documented on post-it notes, while the knowledge system is done via email chains and a Word document. We’ve all seen the dreadful email chains with “knowledge”, such as the infamous …can anyone share with me the file with the A/B test experiment we did for Nike last month? I saw someone share it via email, but I lost it. Something’s wrong with my Gmail 😊”.

If any of this sounds very much old school to the point of exaggeration, it means you probably work at a tech-driven early stage firm. The described scenario is probably the modus operandi for 90% of all firms. How many times have you entered a meeting room at a client’s office and seen all the post-it and paper sheets glued to the walls? Or how many post-it notes are glued to workstations? And email chains sent with the results of last week? Worse, it is not uncommon to see a CEO sharing a new mission statement every year over email to the entire organization, bypassing everything we know about effective time management and communication skills.

Table 2: The Boring Life of an Onsite Firm

Remote

We have enough material to plan a migration from onsite to remote setup. Migrating to remote work, assuming you operate under certain efficient management methods such as OKR or similar, should be straight forward. You can replace an office with a combination of tools such as Zoom (or other conferencing tools), Breather* (or other meeting rooms for rent), offsite locations, home desks, and restaurants. You can replace physical storage and communication with productivity apps such as Slack (day-to-day conversations, searchable), Asana (tas management software), Betterworks (OKR and performance review platform), and Salesforce (CRM). Let’s go over each of these tools summarized below on Table 3.

In a pre Covid-19 world, our fictional company was used to managing their team and day to day operations in the most boring way possible inside a beautiful office on the 15th floor of a corporate building. Now they have no option but to migrate to remote. Here is their game plan:

Board meetings take place via Zoom, and once a year, the CEO and the board meet in person by renting a meeting room location using Breather, an online rental place of meeting rooms. Other options to Breather are coworking spaces that offer the rental of meeting rooms per hour, or even a board member that has an office and agrees to host everyone.

The company has decided to use Betterworks, a software management tool designed to ease the process of setting and documenting in a collaborative way the goals, objectives, and key results of the company, as well as to track, measure, and provide real time feedback on individual performance. Other options are as simple as the documentation of goals, objectives and results using any cloud based and real-time editing tools such as Google Docs and Google Sheets. The key is to make sure that every person on the team has access to and follows the plan. The company has decided to have an annual strategic session in an offsite location, in person, with all the director level and up personnel. Further, quarterly meetings between the CEO and the C-Level team are done via Zoom, yet one of these meetings will be done off site in person. All other meetings including monthly and weekly will be done via Zoom.

Results will be documented and tracked using Salesforce, where the team can prepare dashboards showing the funnel, conversions, engagement, and attrition screens. Senior team members will have regularly scheduled breakfast or lunch sessions at local restaurants, paid for by the company, with individual members of their teams to go over objectives, results, and reviews.

The team has settled on using Asana, a task management tool that is specifically designed to link goals to tasks. Using this tool, associates are able to keep track each day of the tasks required to reach an objective and see how those tasks are aligned to the company goals. It also provides transparency and accountability to everyone, as the tool makes it easy to share and see the tasks and progress of others.

Finally, the company has agreed to support people to work effectively from home or from a coworking space near home. The decision as to who works at home or at a hot-desk is made by the individual. Some people have a quiet, well lit place at home to do work while others don’t. A solution for those that want to stay at home but don’t have the right room or privacy to do so should get a budget from the company to refurbish a place inside their home or to purchase a phone booth, such as those sold by Room. The company should agree to pay for cleaning services at their employee homes, removing a common obstacle that people typically find when working from home (the house is a mess and people procrastinate by pretending to clean up). Alternatively, the company allows employees to work from a desk at a coworking space near their home.

Table 3: Going Remote

Table 3: Replacing the Onsite physical hardware, storage, and communication applications with Remote based applications, the setup allows for people to do most of their work from home. *Breather refers to a US based company that rents meeting room spaces per day. Other countries may have coworking spaces that rent meeting rooms for a day, such as WeWork Now.

And there you have it. For companies that were well-functioning before the Covid-19 crisis and before having no option but to migrate to remote, their migration is actually easy.

People And Advocacy

All of the above is probably too much for a single person to coordinate and manage, particularly the CEO who is probably busy with not just managing the company but also doing key business development. In my experience, the team that should own all the tools mentioned and the OKR process (make sure every staff member understands and fills out their tasks and objectives, coordinates retreats, meetings, scheduling, etc) needs to be a strong and independent area within the company with direct reporting to the CEO. In my case, I built an area called People and Advocacy, which separate from HR, owned the entire OKR process, all the systems involved (Salesforce, Slack, Asana, etc), and all the meetings. A calendar invite from this team in your inbox meant the highest priority and non negotiable attendance. For example, you would receive an email asking you to fill out the quarterly objectives for Q3 on a specific calendar day, and to participate in a mandatory quarterly meeting with the CEO. This role became the Slack content moderator and at the same time the Salesforce adoption teams reported straight to her. In my calendar, I had my first Monday morning meeting reserved exclusively to meet with the head of People and Advocacy. That was a signal meant to tell everyone else that this was my number one priority, always.

Putting It All Together: Final Thoughts

CEOs and business unit leaders are required to adapt and adopt the tools that everyone on the team will be using. Migrating from Excel to Salesforce to capture customers will be a failure unless the CEO uses Salesforce to produce dashboards every day. Likewise, no one will follow a mission statement, or a goal for that matter, that was communicated via email. Remote Leadership is about how CEOs manage their time, how they communicate, and how they manage their team. Remote Work is about the tools required to make things seamless. The latter is easy and low cost since, for example, changing a lease from an office to a coworking space is no big deal, or having a meeting in a room or via Zoom is also a relatively easy and painless change. The former is the most difficult part. Figure 3 presents a summary and guide. This one chart can be printed and posted on the CEOs window (in his house). Everything else goes to the cloud.

Figure 3: A Remote Leadership System

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The author is a managing partner at Matterscale, a venture capital firm. He is also an Adjunct Professor at Columbia University SIPA. Previously, he was the president of Endeavor Global, a non-profit supporting entrepreneurs in 35+ countries. He lives in NY and works mostly from home. Contact information:

Fernando Fabre

Email: fernando@matterscale.com

Website: Matterscale.com

Twitter: @fabref