Manager Training: How to Help Your Managers Manage Their Remote Team

When the pandemic hit,  people started to wonder: How can I help my managers lead their teams remotely? How do I help them engage with their work — and more importantly, with their teams?

Our Co-founder, Chris Zaugg, partnered with 360Learning’s Head of Learning, Jonah Goldstein, to answer these questions and more on the Post-Pandemic Manager Training: How to Help Your Managers Manage Their Team Remotely webinar.

Didn’t catch the live webinar? 👉 check out the recording here

Don’t worry—there’s no “fear of missing out” here: We’ve summarized the key points from the webinar below. 

Manager Training is Really Important to Get Right…

For Chris, manager training should set managers up to understand how to get the best of their team members and have them feel like they “won the workday”. And for Jonah, it’s vital that manager training enables company culture to scale as managers engage with their teams and as they grow into role models. 

As Jonah said, “Manager training is collaborative and explains what expected behaviors are: It’s not canned jargon. It’s about transforming your company’s culture and having your managers deeply investigate their management behaviors independently and with each other.” 

“Manager training is collaborative and explains what expected behaviors are: It’s not canned jargon.”

Ultimately, your manager training should serve to give your managers the skills they need to deepen their relationship with their team members, resulting in a better work environment for everyone involved. 

…But Manager Training is Difficult to Do Well

According to a study we conducted last summer, only 5% of managers think managers training actually works. Gulp. 

It’s clear that traditional manager training methods aren’t working: In-person seminars and workshops unload broad, generic knowledge through long lectures — and don’t hold managers accountable for implementing what they learned.

If traditional training methods weren’t effective when we were all in an office together…then they’re even less effective now that the majority of us are working remotely. So how can you fix this?

Make Manager Training Asynchronous and Collaborative

Instead of making everyone sit down together and listen to the same lecture before going back to their workday, you should strive to make your training asynchronous and collaborative. 

The pandemic presented a lot of opportunities to go asynchronous with training, allowing managers to get the training they need — on their own time and in their own way. But when it comes to this method of training, you have to be mindful about striking the right balance between being asynchronous, and still encouraging and making space for collaboration. You don’t want managers to feel like you just assigned them a training and now they’re on their own!

One way to promote collaboration around asynchronous training is to encourage your managers to discuss the training amongst themselves and even with your HR departments. A great way to encourage these types of discussions is to create a space for managers to post questions and comments they have on the training, as well as to share their takeaways. As an added bonus, you can use these informal conversations and training assessments to update lessons and continually improve your training program.

Train Managers on Expected Behaviors

If you have defined expectations or cultural frameworks at your organization, then your manager training should clearly outline and detail them. 

Jonah shared that at 360Learning, they have a very specific and clear set of values that they’ve defined and refer to as “Convexity”. It is their belief that in order to lead remotely, their managers must demonstrate “Convexity” — so their manager training is clearly organized around the specific behaviors and expectations that make up “Convexity”. 

One example of how 360Learning centralizes their training around manager expectations is the idea of “Rationality” and the “Pyramid Principle”.

One of the pillars of 360Learning’s “Convexity” is “Rationality” and the idea of communication (especially written communication) needs to be clear, fact-based and transparent. In this day and age when opportunities for face-to-face communication are so limited, it’s vital that managers communicate clearly and in a matter that leaves little room for misinterpretation, so 360Learning trains all their new managers on the “Pyramid Principle”. The “Pyramid Principle” provides managers with a framework for starting with the answer first, grouping and summarizing their points, and logically ordering their ideas and results in clearer communication across the organization. 

Train Managers on Transparency and Help Them Break Down Communication Barriers

Building a strong relationship with team members can be challenging for managers during the best of times, and is infinitely more difficult to do remotely. 

Managers often feel like they needed to share all their victories and none of the failures, but the opposite is true. When managers are transparent, they become more relatable to their team. Their team then feels more comfortable opening up about their roadblocks and challenges.

You can help your managers model transparency by creating a communication framework that helps keep their team connected.

Your framework might include:

  • Expected response times: Establish how often managers and team members should be checking their email, or responding to Slack messages. And don’t forget to create guidelines  around who to reach out to for emergencies, and how to contact them.
  • Promotion of non-work socialization: Yes, the work has to be done. But what a lot of people are really missing in a remote environment are the casual “water-cooler” conversations. Casual conversation is a huge part of office culture, so look for ways to recreate those candid moments. At Uptick, we’ve created fun Slack channels like #pets-of-uptick and have a weekly Friday am zoom call where we talk about anything but work — while eating donuts!
  • Weekly one-on-one meetings: These are another space for your managers and their team members to talk about something other than project updates (those can be handled via email or Slack). One-on-one conversations should serve to clarify expectations, remove roadblocks, define goals and build relationships.

When creating fun, conversational spaces you should be transparent about their intention: People want to build connections, yet they also understand that they have a job to do. While you have to ask your team about status updates, you don’t want every conversation to be so work-focused that they feel like a machine.

But what if people don’t participate in those spaces? How do you get out of just status updates and move beyond the numerical values of your company goals? This is where the one-on-one meeting comes into play. 

Remote One-on-One Meetings

One-on-ones are hard to get right — even when your managers and team members are able to meet face-to-face. Luckily, Chris shared some actionable tips and tricks that you can relay to your managers. 

Leverage open-ended questions

The key to making any conversation great is having both parties participate, and open-ended questions are a great way to get team members talking. Here are some examples that your managers can start using in their one-on-ones today.

  • What are you finding most challenging about working remotely?
  • What’s your favorite thing about working remotely?
  • What could we do to improve our remote meetings?
  • What are the unique gifts and talents you bring to the team?
  • What’s missing from your workspace?
  • What’s your biggest distraction during the day?

One-on-ones aren’t status updates

You can handle status and project updates over email or Slack. Your managers should be using their one-on-one time with teams members to clarify expectations and priorities, remove any roadblocks in their way, and deepen the relationship/

Consistency is key

One-on-ones should be scheduled in advance and rarely skipped or re-scheduled — we’re talking, emergency situations only. When managers cancel or reschedule their one-on-ones, they signal to their team members that the meeting isn’t all that important.


Your managers and their team members should both contribute to the agenda — that way they each have a stake in the meeting. And any agenda items should be shared with team members in advance, nobody likes surprises at work!

Manager Training for Remote One-on-Ones

The pandemic shook up the workplace, but one thing remains clear: Your manager training should provide your managers with the tools and skills they need to help their team members reach their goals. In this webinar, Jonah and Chris provided valuable insight for you to help managers empower their teams during this time. But now it’s time for you to consider how you should go about implementing this at your organization.

Our Next-Level One-on-One Course is everything that we’ve learned and trained our own managers on when it comes to one-on-ones. The course covers everything from leading teams, to managing priorities, setting goals and building trust. Your managers will walk away knowing how to plan, implement and run productive one-on-ones that don’t just fall into the “status update” rut. Learn more or enroll now. 

Wish your team was performing at a higher rate?
The Next Level One-on-Ones Course is an accelerator for you in your leadership journey.

It’s everything that we’ve learned and trained our own managers in how to lead their teams, manage priorities, set goals and build trust — without falling the rut of aimless status update conversations. 
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