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Preparing your team for in-office or hybrid work

How to challenge existing norms and redefine the ways you want to work together

December 2, 2021

It almost feels like just as soon as we all got comfortable with this whole “new normal” of working from home, many of us will soon be shifting back to work in the office at least some of the time. We sat down with Sarah Milstein, VP of Engineering at ConvertKit, as part of our Lead Time Live series to discuss what opportunities lie ahead and how teams can use time now to start adopting more effective, inclusive ways of working when we come back together — in whatever capacity that looks like.

What will “going back” actually look like?

Here’s a quick look at different ways companies might approach their return plans:

  • Traditional model: Everyone’s back at HQ, full-time
  • Distributed model: Everyone’s back in a physical office, but some are at HQ and some are at satellite offices
  • Hybrid model: Some people work in the office, some work remotely
  • Synchronized hybrid model: People can WFH, but are expected to come into the office on agreed-upon days — maybe the entire company comes in on Monday, Wednesday, and Friday; or certain teams come in on certain days of the week
  • Activity-based hybrid model: People can WFH, but come into the office for certain types of activities — maybe Tuesdays and Thursdays are designated meeting days, so folks tend to come into the office to meet in person
  • Fully remote model: Everyone will continue to WFH

Different approaches will obviously benefit different teams, and there’s no right or wrong way to do this. A lot of it depends on things like team size, geographical location, and team and personal preferences.

From years of experience leading hybrid teams though, Sarah says a model that mixes flexibility with some structure around office time generally works well for most teams.

“What I’ve seen to be most successful are companies where you can make a choice [to work from home or the office] and the systems are set up where you can do that most days, but there are also clear agreements about when you come in,” she explains, “whether you have team days that are Monday and Wednesday or the whole company comes a couple of days a week.”

Sarah says this model works well because it accounts for two important things: giving people the flexibility to work how they’re most productive, and prioritizing spending time together when situations require it (like for meetings or team building activities).

She also cautions about choosing a model where it’s up to team leads or managers to decide for their function (rather than the org as a whole), because this can create unintentional inequity depending on how teams are made up.

“I think it’s important to raise the question of equity now,” she shares. “We’ve had everyone working from home, in most cases very effectively, for a long period of time now. We have an opportunity to ask ‘What is it that we’re optimizing for?’ And what have we gained in this time? What have we learned? What have we lost? How can we be careful about accounting for those things rather than just defaulting back to where we were.”

If, as a manager or team lead, you find yourself in a position where you’re being asked to set the policy for your team — Sarah offers a few pieces of advice:

  • If you’re not in the position to set the policy, raise the issue upward
  • Frame the problem around business benefits — “It’s important to have an office policy that’s fair to everybody because hiring is difficult right now. We don’t want to foster resentment or incentivize employees to leave.”
  • Talk to peers who are managers in other departments and build some alliances and soft norms on what you’ll agree upon for your teams
Learn more about the pros and cons of different hybrid work models

How to prepare your team

A moment of opportunity

Remember back to the spring of 2020? Yes, the initial move to remote work was jarring. But chances are your newly remote team got some real, tangible benefits out of it too — whether that was more focus time, greater empathy and understanding for one another, new collaboration tools and processes that seem to work well, or new ways of checking in with each other that folks actually really love.

Now, fast forward to today. Rather than thinking about this upcoming shift back to the physical office as a challenge or pain — why not reframe return plans as an opportunity? A chance to help us move away from some of our autopilot norms around working in in-person offices and more intentionally decide how we want to work together.

Sound exciting? We think so too. Here are some ideas Sarah shared around hybrid work planning to help your team get ready for this next new normal.

1. Make sure you have good management in place

Managers should be having regular 1:1s with folks, finding out where they’re challenged, where they’re thriving, and where they need extra help or visibility. This should be the case always, but is especially important when going through a big shift. Keeping communication channels open, checking in with each other proactively, and ensuring remote folks feel equally supported as in-office ones will be critical.

2. Begin to challenge existing norms and processes now

Sarah recommends trying out new things and beginning to make changes now, so you’ll already have some strong foundations in place and the team will better know what to expect. Going back to the office isn’t a new thing by any means, but eliminating as many of the unknowns as possible can help folks feel more prepared for the transition.

Sarah pointed out that hybrid work models aren’t all that new either — many companies have had satellite offices or remote employees for years. She recommends looking to these companies for inspiration as we move into this phase.

If you’re not sure where to start thinking about your return to office plans, Sarah’s got a few ideas. She recommends using this time to revisit old norms and challenge existing beliefs and ways of doing things. Here are a few examples.

  • Meeting facilitation: In hybrid work planning, be intentional about who presents, who runs meetings, and who demos work — rotate between office workers and remote folks. You don’t have to be in the office to lead a great discussion.
  • Proximity to execs: “But won’t people in the office get more opportunities for promotion?” Many people believe think that working in close proximity to an exec team gives you some sort of advantage, whether that’s the opportunity to bump into them in the break room or chat at an event. In actuality though, Sarah says being removed from execs can be quite valuable.
“It’s less of a distraction,” she explains. “In the office, there’s usually quite a lot of focus around a few people and speculation on what they’re doing and thinking. It’s kind of a waste of energy.”
  • Career growth: If you do find that remote folks aren’t getting equal career attention — do some analysis. Diagnose what the problem is and then experiment with ways to solve it. Do you have a strong happy hour culture where office workers go out after work and build relationships in that way? (Try quarterly get-togethers or encourage folks to come in for team-building activities once per week.) Are people less aware of remote folks' work? (Build systems that promote it — regular check-ins can be a good place to start.)
  • Meeting technology: Sarah says you don’t need to invest millions of dollars to run a solid virtual or hybrid meeting. Instead, take some inspiration from meeting facilitators who came before us — companies have been running conference calls for decades. Sarah recommends investing in really good audio in your meeting or conference rooms, video is far less important. A great hack for video is to have everyone in the meeting (in-person and remote) join the meeting from Zoom on the laptop (muted, of course). It may feel awkward at first, but it really levels the playing field and allows for people who aren’t in the room to participate more fully.
  • Coaching interns, new hires, or grads: Coaching new teammates, in particular interns or folks right out of school, has been particularly challenging remotely — since so much of that process typically revolves around shadowing someone with more experience. There are ways to make it work though. Sarah recommends scheduling regular pairing sessions and designated time for asking questions. (Questions can and should come up at any time, of course, but she’s found that actually scheduling these things makes people more likely to use them.) It’s important to have a strong feedback structure in place too — whether that’s a weekly check-in with a manager or team leader, scheduled time with other ICs for idea-sharing and feedback, or ideally both. Constructive feedback is essential to everyone’s growth — check out our tips for giving stronger remote feedback.
  • Asking for help: Working remotely often means it’s harder to track down answers to problems you’re trying to solve, since you can’t just spin around in your chair and ask a neighbor. Normalize asking for help — no one should be fumbling around for an entire afternoon looking for answers. If they can’t find it on their own in 15 minutes – encourage them to ask a peer or team manager. There’s nothing wrong with that. You might try creating a help channel in Slack with very strong norms around “no dumb questions” — ask leaders to replicate the behavior (posing questions of their own within the channel) and teammates to be quick and generous in their answers, so that folks actually feel comfortable putting their question out there.

3. Use this opportunity to experiment

As we’re gearing up to return to the office or a hybrid model of working, now’s a great time to start thinking about the shifts your team might make in the coming months. Rather than simply change what we’re doing now though, Sarah says teams should use this moment for experimentation.

“Experimenting and trying new things is a new opportunity and possibility that we have now,” she shares. “This wasn’t something that came up as much when we were just working as we always had in our day-to-day.”

Got a new idea or something you’d like to try? Share it with your entire team, explain your hypothesis around it, and give a clear timeline for when you’ll check back in around how things are working.

“When people are given an end date to something — “we’ll check back in 3 months from now” — they’re a lot more open to trying something new,” Sarah explains.

Predicted challenges with hybrid work (and ideas to solve for them)

The shift back to an office or hybrid work environment is full of opportunity, but it would be unrealistic to say there won’t be challenges ahead of us too. Sarah shared what she believes will be some of our greatest challenges going forward, and some ideas for how teams might think about and approach them.

1. The lack of personal connection

When we don’t see each other in person, it’s really difficult to make personal connections. Facetime really makes a difference for a lot of people. Without in-person facetime, it’s harder to read how people are doing, get to know each other, and feel like you’re part of something.

How to solve for it

“On a personal and business level, knowing whether people are having a good or bad day helps,” she says. “When someone’s not as responsive or short, you have that context so you don’t have to worry if there’s subtext you’re missing.”

  • In-person moments for the whole team: If your team is remote or hybrid, carve out certain moments throughout the year where it’s agreed upon that everyone will be together in-person. Maybe that looks like a weekly in-office day, a monthly dinner or happy hour, or an offsite a couple of times a year. This will help folks build relationships in a way that might not be possible when working remotely.

2. Collaboration — especially on strategy

It’s hard to collaborate on certain kinds of work when you’re not together. In particular, generative work and things that need group focus and attention, like strategic planning. These activities typically require long chunks of time together to explore and dive deep into things, but let’s face it — nobody wants to be on a 6-hour Zoom.

How to solve for it

  • Restructured generative sessions: Strategy and planning meetings can happen virtually, you’ve just got to think outside of the box when it comes to the way you structure them. People tend to be able to focus on Zoom for up to 90 minutes, so use that as guidance in how you shape these types of sessions.

How to structure virtual strategic planning

Day 0:

  • 30-minute tool session: Schedule a half-hour on the day before your meetings for folks to download and learn any new collaborative tools you’ll be using. They can do this independently, but make sure you schedule the time so folks actually prioritize it. Doing this ahead of time means you won’t be stumbling through when you come together to meet.

Day 1:

  • 90-minute kick-off: In this first moment over video, you might do a group icebreaker, review metrics and progress towards company goals, and outline what you’re trying to accomplish together in these sessions.
  • 1-2 hour break: Give people a break for reflection, silent writing time, stepping away from work, or whatever feels necessary. Encourage folks not to use this time for other meetings – which will just be more depleting.
  • 60 minute regroup: After the break, come back together — this might be for brainstorming, research findings, breakout discussions, or deep-dive presentations.
  • 1-2 hour break: Another break to give folks time to re-energize.
  • 90-minute end-of-day session: Wrap up the work you’ve accomplished that day and outline clear next steps.

Depending on the level of planning, you might repeat these spaced-out planning sessions over the course of a few days or a week.

3. Trust and visibility

Trust doesn’t come quite as naturally when you can’t directly see the person you’re working with. Managers might worry their direct reports aren’t getting work done, or reports might worry their work is going unnoticed.

How to solve for it

  • Real conversations: Sarah recommends posing an open question to your boss or report on the matter — “What do we need to demonstrate in order for each of us to feel comfortable with this work setup?” — and the co-create some agreements on how you’ll show progress. That might look like a daily check-in, a weekly email summary, or something else.
  • Written check-ins: To bolster trust and prevent micromanagement, you might try adopting a practice around daily or weekly written check-ins to detail progress and blockers on in-flight work.

With a little foresight and planning, your team can solve for these common pitfalls before making the actual shifts back to the office or a hybrid environment.

An opportunity for learning and growth

To be a successful team during this time of transition will mean to trust each other, be open to trying new things, and lean into consistent communication. Effective communication and regular feedback is always essential — even more so as you lead your team through change.

As you gear up for the new, new normal, unite around a smooth transition as your common goal and hold yourself and team members accountable towards reaching it together. Schedule regular check-in moments where everyone can share their feedback and ideas, and know that the process will be an interactive one. Just like the transition to remote work — you probably won’t get it all right on the first try. But you will learn and grow a lot as a team along the way.

Preparing your team for in-office or hybrid work
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