How Clockwise Helps Greg at Asana Be a Better Mentor

Cathy Reisenwitz

by Cathy Reisenwitz on November 26, 2019

Greg Sabo is an Engineering Manager at Asana, responsible for ten Engineers across four teams. In between his weekly, 30-minute one-on-ones with reports, he does a lot of what Asana calls “white space work.”

This is work that doesn't fall neatly into any one category or chain of command. It could be identifying opportunities for running Asana more efficiently or establishing better business practices. “Sometimes that includes mentoring somebody else that doesn't report to me,” Greg said. “I'm usually juggling at least at least three to five different major projects in addition to my reports.” All of this involves plenty of meetings.

Challenge 1: Too little Focus Time

While meetings are an essential part of Greg’s role, they cut into his work time. Meetings also cut into his reports’ work time.

“As an Engineer, it's very hard to make consistent progress when you only have 30-minute slices of time to work between meetings,” Greg said. “It’s almost like that time is wasted, in terms of focus. You can only really do trivial things during that block of time.”

The research bears this out -- context switching decreases productivity.

“Because I schedule lots of meetings with my reports, I often worry that I'm turning their schedule into Swiss cheese,” Greg said. He needs his reports to have plenty of Focus Time for them to be able to accomplish their objectives.

Challenge 2: Too much manual work

Not only were meetings taking up precious Focus Time for Greg and his reports, but they were a lot of work to schedule.

Whenever Greg was scheduling a new recurring one-on-one he’d have to schedule the first few weeks individually because he couldn’t find one consistently available time slot. “And then like a month out I would start the recurring meeting,” Greg said. “So that was pretty annoying.”

He’d also need to proactively identify conflicts and then spend time every week manually moving his one-on-ones. “So I would have a recurring task to look through my calendar and pick up on conflicts that had happened with my one-on-ones and all the other meetings that had cropped up and try and reschedule them,” Greg said.

First solution: Fewer, longer one-on-ones

Greg’s first solution was to meet less often, for longer. “I tried to reduce the amount of context switching by doing 60-minute one-on-ones with my reports every other week,” Greg said. This solution bought him and his reports more Focus Time and reduced the amount of time and effort he had to put into scheduling them.

Drawback 1: Hard to develop trust

The big problem with this approach is that one of the main purposes of a one-on-one is to foster trust between a manager and their report. But trust is harder to gain when the meetings are less frequent.

“I've found that it's really hard to develop a trusting relationship at that frequency of meeting,” Greg said. “If you only see someone once every other week, it takes a lot longer to build that trust. I found that was very important to have that weekly cadence.”

One way that lack of trust manifests is that it becomes harder to sell reports on improvement suggestions.

For example, Greg was coaching one of his reports on the importance of storytelling for leadership and communication. “That idea was very strange to them,” Greg said. They didn’t immediately understand why they needed to get better at storytelling.

Greg explained that they needed to be able to tell the story of what they’re building to their team to motivate them and help them understand how it all fits in the bigger picture. Plus, the story needs to be clear to stakeholders. “So that was the idea that I put in their head at first, but that's the sort of idea that at first sounds very strange,” Greg said. There wasn’t a lot of buy-in right away.

Drawback 2: Hard to keep momentum

Greg also found that the longer delay between meetings stalled progress. “I also found that many topics are best discussed over a longer period of time,” Greg said. “Rather than spending an hour going really deep on a topic, it's just as productive, if not more so, to bring up the topic in one meeting and then let them sleep on it for a week and then go deeper on it next week after they reflect on it on their own a bit.”

For example, Greg would bring up a growth area with a report such as improving followthrough. “We’d talk about it in-depth for an hour, and I would say, ‘I'd like for you to think about how to apply this over the next couple weeks on your own.’”

The problem was that two weeks is a long time. “By the time the next one-on-one came around it wasn't top of mind for them anymore,” Greg said. “They hadn’t been thinking about it. The idea had kind of dissipated in their mind in the past two weeks.” Perhaps unsurprisingly, the report with a followthrough problem hadn’t really followed through on improving their followthrough.

“So that's a case where that cadence really did a disservice to that conversation and made it slower for us to make progress,” Greg said.

The Clockwise solution

Clockwise gave Greg and his reports back some of their Focus Time without having to cut down on their number of meetings. The Autopilot feature moved their meetings automatically to maximize Focus Time.

“I do need blocks of Focus Time,” Greg said. But, “I have less need than my Engineers. For me, it's very important to preserve their Focus Time, which is a big draw for me for Clockwise.”

Crucially, Clockwise makes it easier for Greg to see his reports every week. “I've seen each of my reports in-person, face-to-face, one-on-one, every week to build up that trust faster and also to give feedback on things a lot sooner than I would be able to on a biweekly cadence.”

For the report who needed to improve their storytelling abilities, progress came after weeks of talking through real-life examples of storytelling playing a role. They began to see where storytelling would have helped in particular situations.

Meeting more often “helped me kind of just gradually chip away at that mindset and start to extend someone's vocabulary with a new way of thinking and a new mindset that helps them do better in their work,” Greg said. “After a couple of months of consistently bringing up storytelling as a leader every week I found that they suddenly got very excited by the idea,” Greg said. “They started applying a lot more of the specific things that I recommended. And the team just really grew as a result.”

Greg really values that progress, and those relationships. “One thing I really love about Clockwise, I have this confidence that I'm using their time as mindfully as possible, and even taking advantage of the time that would be sort of unproductive as independent time, and still able to develop a really deep relationship with them.”

Are you looking for a way to be able to get more Focus Time without having to sacrifice your valuable meetings? Try Clockwise today to see how it changes your work life, and helps you make time for what matters to you.

Cathy Reisenwitz

Cathy Reisenwitz

Cathy Reisenwitz is Head of Content at Clockwise where she oversees the Clockwise Blog and The Minutes Newsletter. She has covered business software for six years and has been published in Newsweek, Forbes, the Daily Beast, VICE Motherboard, Reason magazine, Talking Points Memo and other publications.

Sign up for our newsletter

Ready to try Clockwise?

Get started for free