How to Lead Remote Workers — A Guide for Managers

Sharlene McKinnon
The KickStarter
Published in
4 min readMar 30, 2020

When people move from working in large, consolidated, office spaces to remote or distributed work environments, a shift towards Lean ways of working and thinking happens almost overnight.

Catalysts for this change are events like pandemics, downsizing, adoption of an offshore or nearshore team, and natural disasters (e.g. flooding, storms that prevent travel).

At the same time, a move towards remote work can expose preexisting weaknesses in typical management practices and structures that have no value in a modern, rapid-paced, distributed workplace. These weaknesses can cause unnecessary noise, slow down progress, create artificial “gates” or barriers, and hinder the ability of a team to reach success in a timely manner.

In both Lean and Design Thinking the core focus is on eliminating waste, validating assumptions, and adapting to customer feedback. These principles help teams get closer to the rapid deployment of small but valuable features that can be tested within a build, learn, and adapt cycle.

Managers don’t need to create artificial “tasks” to help teams be successful (e.g. long meetings, checklists, complicated communication ceremonies, weekly 1:1 meetings). These are all distractions from what a team really needs: an understanding of the direction, an understanding of the customer, and an understanding of what needs to be built.

What teams need can be broken down into 4Ws:

  1. Where are you going? What direction is the company going in? What is the goal or purpose? What milestones are essential in helping reach the company’s vision or goals?
  2. When do you need to be ready? This ties into a direction. Timing is more than setting arbitrary dates for software releases. Reaching a goal is a long and challenging journey that doesn’t magically happen overnight. It takes a lot of learning, mistakes, and pivots to achieve goals. But, when you understand timing, you can work backwards to evolve what is needed to get there.
  3. Who is the customer? Who is the consumer of the software or product? What do these people want? This is where iterative learning comes into play.
  4. What are you building? Focus on getting requirements for people and prioritizing only the most valuable features so you can test these quickly with customers. This focus means cutting all the noise and surfacing only the most valuable things.

Companies and teams that don’t have the above details worked out will flounder in a remote work scenario. Or you’ll have difficulty motivating people because they don’t see the value in what they are building.

Tough times expose dysfunction. This is terrible news for all those companies that have existed for a long time in a flawed, maladaptive state.

What is the role of management?

The role of management is to understand and communicate everything above. Let the teams figure out the “how.” If you give teams everything above, they are empowered to do their job.

This means less focus on watching people and more on reiterating direction, purpose, and what needs to be built.

Your job as a manager is to remove distractions and blockers to success. Remove unnecessary meetings and only communicate what is necessary.

The most important thing a manager can do in a remote working scenario is to communicate, so the individuals on teams don’t have to. This means setting up information gathering structures:

  1. Daily communications (e.g. stand-up, design stand-up, product-tech stand-up) → short daily meetings designed to gather information about progress and blockers to success. This also serves as a means to communicate changes to the team. A great example of this is Prime Minister Justin Trudeau’s daily communication with Canadians.
  2. Shared understanding sessions (e.g. iteration kick-offs, project kick-offs, mini-hackathons, campaigns) → longer sessions for sharing information that comes from technology, product and design team working sessions (tech investigations, design charettes, customer usability sessions, data analysis, JTBD analysis). The objective is to gain a shared understanding of customer and technical requirements.
  3. Stakeholder checkpoints (e.g. stakeholder stand-up, weekly checkpoint, goal/milestone checkpoint) → To communicate progress or remove blockers gathered during stand-up. These should be short and focused. These include quick checks of company milestones and goals.
  4. Learnings & pivots (e.g. retrospective, postmortem) → To share learnings, issues, blockers and figure out how to adapt or evolve. Continuous learning fits into a Lean build, learn, adapt cycle.
  5. Celebrations (e.g. showcase, fail party) → To celebrate and close work. To share learnings and help people understand that it’s ok to fail.

For all of these, there are plenty of remote tools (beyond video) that can facilitate these activities.

How do you manage in a remote situation?

The best thing you can do for a team as a manager is cut through the waste and focus on what is truly important and has value. Empower the team to help figure out what is valuable.

Finally, it’s your job as a leader to remind people of the goals and directions. You’re on an expedition; it’s essential to keep reminding people to stay grounded and focused on the goal.

The goals shouldn’t change because people are remote. If the goal changed, there’s a bigger problem. If the goal is not clear, you have work to do. This is the first thing that will come to the surface when teams go remote.

The companies and teams that will survive are the ones that can adapt and work together without all the noise.

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Sharlene McKinnon
The KickStarter

Geek. Multiplier. Leader & Mentor. Digital Humanities. I work at the intersection between humans + technology.