Why Remote Leadership Training Saves Your Company Money

Toolie® Garner
6 min readJun 21, 2023


The success of remote and hybrid teams rest on whether leaders have these key skills.

So what’s the difference between general leadership training and remote leadership training? Probably more than you know, or you might not be asking the question. Let’s start with some general skills and traits, some of which leapt to the forefront because of the impact of the pandemic on companies in the last 3 years.


As a leader, what impact do I have on my team members?

“People don’t leave companies, they leave their managers.” I’ve seen arguments on both sides of this trope: leaving because of the job the manager designed, or leaving the manager for a variety of other reasons. I’ve experienced both. One way or another, your role as a leader impacts your employees, and self-awareness is the first step in making your team loyal to you as well as to the job. Keep reading…


You could always count on someone’s pet to take the edge off a tense meeting.

If there was one thing the pandemic did for business, it was that it reminded us that businesses are made up of people: human beings with responsibilities, concerns, fears, and dreams. Working from home gave us a sometimes-uninvited look at our colleague’s homes as well; their kids, their pets, the art on the walls (or lack thereof), and the worn couches. Whether from embarrassment or necessity, managers, leaders, and bosses needed to be empathetic for their teams to get through the crisis with some semblance of self-respect and dignity.

Now that the worst of the pandemic appears to be behind us and companies are insisting that employees return to the office, somehow that empathy is also waning. Companies that behave as though nothing changed are losing out to companies who are more flexible, offering hybrid or fully-remote work options to retain their employees. I’ll talk about the costs of employee retention in a minute.

Creating Structure

If you don’t measure, how do you know when you’re done?

One of the differences between teams that thrived and those that struggled is structure. When we stopped being able to tap each other on the shoulder for a quick answer, we learned that having the worked structured in a way that it could be measured and tracked made it easier to determine when it was done.

I worked in software tech as a project/program manager/scrum master, where tools like Jira and Azure DevOps helped us stay on top of the work. But even then, I was constantly having to remind the team to document the work so it could be tracked and marked complete. Don’t even get me started on the Definition of Done! But I can say that having that Definition and having the process that leads up to Done is a recipe for success.

This approach isn’t just for software developers; I led 2 different Marketing teams within a task-oriented structure like this, so I know that it can be applied to teams in almost any industry.


Getting the team to talk to each other is challenging even when they’re all in the same room. Listening and asking questions are skills that are likely not taught at home (parent to child: “what did I say?”). Listening and asking questions are not often taught as revenue-generating skills in business courses, but they really are.

Early in my time at Microsoft, I took a beta version of two-day class on precision questioning which had a profound effect on my career. It taught me how to listen, observe, ask questions in a systematic way. That moved me from a passive role to a proactive, leadership role. I took those skills with me wherever I went: through the rest of my time at Microsoft, through my first 9 years of entrepreneurship, through the last 10 years as a software program manager and scrum master, and now back into entrepreneurship.

Being able to listen between the lines is just as important. If you think a team member is having a hard time with work, knowing how to ask questions in a thoughtful and non-invasive way engenders trust, and reinforces that empathy we just discussed.


Listen more than you speak.

It may seem strange to discuss negotiation as a skill when you’re the boss. But smart leaders know that teamwork involves getting team members to work with each other as well as responding you.

If you have two talented employees who seem to regularly butt heads over stupid stuff, it’s your ability to ferret out the details of the situation and find a resolution that’s going to keep both of them on the team and staying productive. Simply issuing an edict and expecting the appropriate response might work for a while, but sooner or later, one or both will leave for a better opportunity.

And then you’ve lost an experienced employee (or two) and demoralized the team in the process. And if your team wasn’t in the habit of documenting tribal knowledge and the history of recent decisions, all of that information is gone too.

And There’s the Rub

Keep your good employees — don’t let them walk away.

Employee retention is the rub. Despite the recent layoffs in tech, for example, top employees are still keenly aware of the leverage they have to find jobs in companies with a more flexible working style. The Society for Human Resource Management (SHRM) reported that on average it costs a company 6 to 9 months of an employee’s salary to replace him or her. For an employee making $120,000 per year, that comes out to $60,000 — $90,000 in recruiting and training costs. That’s a lot of money to waste, when investing even half that in remote leadership training would save a lot of angst as well as dollars.

As someone who regularly on-boarded new employees in my assignments, I can tell you that it’s a labor-intensive process. Yes, you can automate the compliance and security training with generic video training programs, but that’s not all there is to onboarding.

It’s a lot of work to get employees up to speed on their new jobs; to help them fit in with the rest of the team, and for the team to embrace the newcomer. One of my former colleagues looked at me a couple of months ago and told me that yes, it was flattering to be moved into leadership despite being hired originally as a peer hands-on developer. “But it’s not as much fun anymore.” Having to train new people when he himself was not given leadership training was taxing. He was the most talented developer on the team, and he confessed that he was looking for another job.

Now add remote and hybrid work into the mix, and it just gets complicated all too quickly. Why? Because communication over video is limited to what you can see on camera, and sometimes the body tells you something that the face does not. Communicating by video doesn’t have to be a limitation, though, if you have the aforementioned skills. This is where precision questioning, listening skills, and empathy (and more) make up the difference.

You’re Not Crazy! But There is Help Available

So no, it’s not your imagination that leading remote and hybrid teams can be challenging. Somehow we made it work during the lockdowns, but now we have choices about how to leverage what we learned and really help our teams work effectively.

It’s not something you can necessarily figure out on your own. Plus it would be helpful to have a trusted circle of people working through the same issues with whom you could share ideas and solve problems. That’s why I created a confidential, closed-door group mentorship to help.

I’m nearly done creating my Remote Leadership Success Group Mentorship program, and I’m looking for a small but motivated group of leaders who are ready to join the pilot and help me refine the final details. If this sounds like something you’d like to do, visit www.TalktoToolie.com and let’s have a no-obligation conversation.

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For details on the program, visit www.rlsgroupmentorship.com. For general questions, email me at toolie@toolie.com.



Toolie® Garner

Toolie® Garner is a remote leadership expert, technology expert, professional speaker, author, and consultant at www.RemoteLeadershipSuccess.com.