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The CEO’s Ultimate Guide To Remote Work, Part 1: Boosting Manager Effectiveness

David Hassell
David Hassell, CEO of 15Five

While many of the management skills you normally lean on in a co-located environment are relevant when you go remote, it’s critical to have the right set and cadence of practices to do it well.

In my opinion, 75% of a manager’s effectiveness, especially when it comes to managing remote teams, comes down to ensuring they’re engaging the right cadence of activities and having the right conversations at the appropriate time. By designing a structure upfront and putting that in place, it ensures these things happen.

Here’s the structure we encourage our managers to use at 15Five.

1) Weekly check-ins

Because you and your managers can no longer “manage by walking around,” you’re forced to grant trust and work in a high-autonomy relationship. In exchange, what you need is transparency, not micromanagement.

A weekly check-in is the best solution I’ve found to accomplish this.

Recurring check-ins ensure frequent and regular communication between managers and their direct reports. Research shows that regular check-ins are shown to improve objective factors such as productivity and goal accomplishment as well as subjective factors such as morale, trust, and engagement.

Each week, every employee reflects on their role and provides a brief update, sharing the following things with their manager:

A quick pulse on how they’re feeling
A simple 1–5 scale works great, and they can optionally add some commentary about their rating.

A green/yellow/red on their current OKRs/Rocks/Objectives/MBOs
The color simply represents the confidence level that the objective will be accomplished by the deadline, along with the status of/progress towards any measurable key results.

This gives you as the manager a near real-time assessment of which of your team’s objectives are on track and which might be at risk, with time to actually do something about it if things get off track.

A brief list of their top priorities for the coming week
In addition, they can share the status of the priorities they laid out for the week prior with a simple done or not done.

Bullet point answers to a few simple questions
We always include some version of “What’s going well in your role? Any wins you’d like to share?” as well as “Any challenges you’re facing? What’s not going well?”

I find these two questions to be essential, but you can also add another question each week to break up any sense of monotony, get some great information, and spark important dialogues.

While I admit I feel a bit uncomfortable about being self-promotional at this time, I’d be remiss if I didn’t share about our product.

Check-ins is one of the things that 15Five is absolutely the best in the world at. I built our initial product for this very purpose, for myself, to manage my own remote teams. It works extraordinarily well and we now have thousands of customers using our check-in based platform to drive high-performance and engagement in their organizations.

To that end, I’ve instructed my team to make 15Five free for new teams of up to 50 people through June 15 during the peak of this crisis as our way of supporting you through this challenging time.

So far we’re hearing that it’s been a saving grace for many teams. Kristi Faltorusso, VP Customer Success at Intellishift just emailed our team today to share:

I just want to send a quick note to thank you for allowing organizations like mine, to leverage 15Five during this challenging time. I’ve only been using it for a few days but I already see a shift in how my team is engaging with each other. I hope to be able to continue with the service long after this, as I see immense value in it.

Be well and stay safe

To be clear, you don’t need 15Five to do this. You can certainly create a system that models the framework I’ve outlined above where you can have your team email you those updates in that format once each week.

However, if you choose to leverage 15Five as your platform, it will:

– Ensure that check-ins actually get done by managers across your entire company, by managing all the reminders and responses, and allowing your team to respond via the web or on their phones

– Give you the ability to respond in threaded conversations around specific points, even looping in other relevant parties who can help resolve an issue, and add key items to your next 1-on-1. CEOs I’ve spoken with claim that teams that use 15Five Check-Ins surface and resolve issues far faster than teams who don’t.

– Easily allow both your managers and their direct reports to build out their next 1-on-1 agenda as they interact with feedback from the check-in.

– Give you rich reporting and the ability to run interactive custom reports across your entire organization, allowing you to (optionally) engage with not just your direct reports, but employees and their answers across large cross-sections of your workforce. I relate to this as giving you superpowers as a CEO.

– Allow you to review your entire team’s check-ins quickly and in one place, so you (and your managers) can get briefed on every important project and initiative being led by each of your direct reports.

– Finally, 15Five also invites each of your employees to give their peers “High Fives” as the final step of each weekly check-in, which ensures a constant stream of peer acknowledgment and appreciation across the organization. You and the rest of your team can see a steady stream of those through the High Fives Dashboard or even have them piped into its own Slack channel.

To give you an idea of how customers view 15Five, our newest customers, Alexandra Erman, VP People at StreamSets, just posted on LinkedIn yesterday about her experience.

She shared, “Our teams are very distributed, and we can’t always grab someone in the hallway. 15Five is really helpful for improving communication at StreamSets,”

She also shared, 15Five is definitely an employee-centric product. It encourages employees to take ownership of their individual milestones. It provides an opportunity to check in asynchronously for those who are still building their comfort with a culture of two-way feedback. It allows for agile movement and change.

2) Regular 1-on-1s

So if I’m doing check-ins, why do I need to do 1-on-1s?

Check-ins are NOT a replacement for in-person (or in this case, video) 1-on-1s, which are an essential management practice, especially with remote teams when face-time doesn’t necessarily happen by default.

That face-time is important for building a relationship and trust, driving accountability and results, supporting an employee in their growth and development, and helping to resolve more challenging issues.

Check-ins do however have the ability to supercharge your 1-on-1s. The reason for this is simple. Because your 1-on-1s are what I consider expensive time (because they’re synchronous and require mutual scheduling), they should be designed for maximal efficiency and impact.

Check-ins get the updates out of the way, and even allow you to converse about, address and even resolve issues in between your 1-on-1 meetings. They also allow you to tee up the most important conversations by adding them to your next 1-on-1 agenda as you move forward. That way, come 1-on-1 time you’re ready to go and able to spend less time getting up to speed, and more time digging in on the few, more critical items that need your time and attention.

I recommend a regular cadence of 1-on-1s on the same time and day so you can set them and forget them. Depending on the situation, they can happen either weekly or every other week, for between 30 to 60 minutes; however, I’ve found that when combined with check-ins they can happen less frequently for less time.

Because I rely on check-ins to keep me informed, I have standing 30-minute 1-on-1s every other week with my leadership team, but we connect for ad hoc work sessions in between. However for many of your managers, a weekly cadence is likely more appropriate.

3) Spontaneous messages or calls to check in and see how your team is doing

It can also be good practice with remote employees to reach out periodically via Slack, text or a phone call just to check in. One of my leaders will often do this during his daily runs or chores and ask his team simple questions like:

– How are you doing?

– How’s XYZ deal going?

– What’s the latest on ABC?

– Anything I can do to help you?

– What do you think about _____?

Sometimes these are just two-minute conversations, otherwise 45 minutes. They just talk, no agenda.

4) Office hours

Because you’re not sitting at your desk in the office, your team can’t just walk by and ask you to chat or hop into a meeting they are having with their team in the conference room.

Having a weekly block of office hours available on your calendar where any one of your managers or team members can book a slot is a great leadership practice. You’re making yourself available for the inevitable issues that come up throughout the week and provide your people another key touchpoint with you.

5) Reviews

Finally, the weekly/bi-weekly cadence of check-ins and 1-on-1s is a great rhythm for reflecting on and staying on top of the work that needs to happen in the near term, it’s not a great structure for reflecting on things happening on a longer trajectory.

For these, we do recommend some sort of regular, more zoomed out review. We practice a lightweight form of performance review that we call the Best-Self Review (because it’s designed to not only assess past performance but also focus on the future growth and development of the employee over time).

We recommend doing these reviews anywhere from 2–4 times per year (vs annually) as they serve as more detailed checkpoints over time to assess performance, growth and an employee’s career trajectory.

Keep reading The CEO’s Ultimate Guide To Remote Work:

– Part 1: Boosting Manager Effectiveness

– Part 2: Individual Work Practices

– Part 3: Company-Wide Practices

– Part 4: Shifting Your Mindset

David Hassell, CEO of 15Five

David Hassell is a business columnist, speaker, and serial entrepreneur who believes that when leaders institute cultural practices that support each person in being and becoming their best self, high performance and uncommon loyalty naturally result. As co-founder and CEO of 15Five, David created the science-inspired Best-Self Management methodology that helps leaders and managers address the hidden factors that stimulate sustainable growth and development – things like intrinsic motivation, strengths, and psychological safety. David has been featured in The Wall Street Journal, Inc., Entrepreneur, Fast Company, and Wired. Follow him on Twitter @dhassell.

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