Remote Work

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Offsite planning for Everyone

Allison McMillan • April 24, 2023 • Atlanta, GA

The video titled "Offsite Planning for Everyone" features Allison McMillan discussing effective strategies for planning off-site meetings, whether in-person or virtual, especially in the context of the increasing shift toward remote work. The presentation emphasizes the importance of fostering connection among team members, aligning company missions, and enhancing employee engagement in a virtual landscape.

Key Points Discussed:

  • Understanding Off-sites: McMillan opens by acknowledging the emotional and logistical challenges associated with off-sites during and post-pandemic, noting the mixed formats that companies have adopted: in-person, virtual, and hybrid.
  • Goals of Off-sites: Defining clear objectives is crucial for off-site planning. McMillan stresses that off-sites should have specific goals beyond just team bonding, such as fostering alignment, collaborative problem-solving, or sharing departmental roadmaps.
  • Logistical Considerations: Effective logistics are vital to reduce cognitive load on attendees. McMillan highlights the significance of clear communication regarding the agenda, timing, and necessary materials in advance to enhance participation.
  • The "Special Sauce": To make off-sites memorable, McMillan suggests adding thoughtful engagement activities, using gifts, and fostering collaborative experiences. Examples include sending craft kits, using interactive tools for virtual meetings, and incorporating fun group activities to break the ice.
  • Examples and Case Studies: McMillan shares various anecdotes, such as a successful team bonding experience at a conference in Portland where personal discussions and bonding occurred in a relaxed setting—showing the impact of off-site engagements on team dynamics.
  • Insights on Virtual Challenges: She acknowledges unique difficulties in virtual settings such as home distractions and needing to manage engagement across different time zones, proposing innovative solutions like varying session times and interactive online platforms to maintain interest.

Conclusions and Takeaways:

McMillan concludes by reiterating that off-site meetings, when planned thoughtfully, can significantly enhance team collaboration and satisfaction, thereby contributing positively to workplace culture. She encourages participants to avoid trying to replicate in-person experiences when planning virtual off-sites, but rather to embrace the unique opportunities that remote settings offer. Ultimately, effective off-site planning requires balancing logistics, engaging content, and a clear focus on team needs and organizational goals.

Offsite planning for Everyone
Allison McMillan • April 24, 2023 • Atlanta, GA

Over the past couple of years, we’ve all needed to sharpen the tools in our virtual toolbelt. More companies than ever are providing employees with the opportunity to work remotely… but how can we keep those individuals connected - to each other and to the mission of the company and their team? Effective in-person offsites are challenging and now we’re working to achieve the same alignment, engagements, and happiness for our employees virtually as well. It may seem impossible, but it’s not! In this session, you’ll learn about how to plan an effective offsite (in-person or remote) and what specific planning considerations can be made to make your virtual offsite just as good, if not better, than an in-person one. Skeptics welcome!!

RailsConf 2023

00:00:19.100 It is great to see all of you in person, and today we're talking about off-sites.
00:00:24.119 Just the word "off-site" brings up a lot of feelings for folks, especially after most of us have taken a few years off from attending them.
00:00:30.119 Think for a moment about the word that comes to your mind when you think of an off-site.
00:00:37.980 Over the past few years, off-sites have been on a roller coaster ride. We planned them, we canceled them; are we getting together?
00:00:45.360 Is it virtual? Is it in-person? Is it hybrid? How are we reconnecting? And these days, do we have the budget to do so? I think I heard someone mention that off-sites can be expensive, but people are still craving the ability to reconnect with each other.
00:01:01.140 There is something special that happens when we're together. We take ourselves out of that day-to-day grind, our work, and our responsibilities, and focus broadly on other things.
00:01:12.720 I'm Allison McMillan, an engineering leadership consultant and a fractional VP of engineering who works with startups that aren't quite ready for full-time VPs but need that perspective and experience on a part-time basis.
00:01:19.080 I am also on the Ruby Central board and I host a podcast called "Parent-Driven Development." Today, we are going to talk about off-sites and what makes them awesome. The best thing about off-sites is that they should be interactive and engaging.
00:02:05.600 During this session, we're going to have some discussions, so if you're not near someone you're comfortable with, I encourage you to move now.
00:02:17.220 I plan to ask a few questions. For each question, you'll have about three minutes to share your answer and discuss, but please introduce yourself first so that you can meet a new Ruby friend.
00:02:36.480 The first question is: What was the best off-site you have ever been to? And if you've never been to a good off-site, think about the best conference you've attended.
00:02:48.060 I'm going to give you three minutes, and I will start the timer now.
00:03:01.680 Hi, I'm Mike Monroe, founder of Obelisk Rails Consultancy based in the Boston area.
00:03:07.920 One of the best off-sites we had was when we brought our entire team out to a conference in Portland, Oregon. The team was based in Boston.
00:03:15.000 We went there to do some bonding and escape the office for a few days. We really enjoyed the time away.
00:03:30.120 The best part about these questions is that you get to talk. The worst part is me standing up here awkwardly for multiple minutes while everyone discusses.
00:03:46.200 For those of you who came in late, we're in pairs or small groups discussing a few questions. The next question is: How did it make you feel while you were there?
00:04:06.299 You have two minutes for this question.
00:04:25.139 While we were at the conference, I felt very light because we had escaped the office. This allowed the team to bond without the constant pressure of client work or day-to-day responsibilities.
00:04:37.680 It gave us the opportunity for deeper personal discussions that we do not always have the chance to explore during office hours.
00:05:01.740 The next question is: What was the purpose of the off-site, and try to think of something beyond just getting everyone together.
00:05:13.500 You have three minutes for this question.
00:05:19.080 The main purpose of the off-site was bonding. As engineers, we spent our days at the office dealing with client requirements for various projects.
00:05:39.900 Many of the team members were working on different projects, and opportunities for meaningful conversations outside of work were rare.
00:05:57.840 By getting out of the office, we allowed ourselves to bond more deeply.
00:06:10.800 The fact that we traveled to the other side of the country helped us escape our typical distractions.
00:06:22.560 Make sure to introduce yourself to another new Ruby friend.
00:06:26.930 Now, think about what made that experience enjoyable. Please share a short story from what made it fun.
00:06:44.820 The trip was enjoyable because our team did not travel much together. The work itself didn't usually involve much business travel, so being able to experience a new setting and learn together was exciting.
00:07:06.780 All right, are you all ready for the next question?
00:07:14.780 What made it draining? You have two minutes for this question.
00:07:26.400 Although the conference was fun, it was also somewhat draining. The travel was positive, but it was still a lot to handle.
00:07:39.120 At the end, we were all pretty tired, not just from the trip but from learning and engaging for several days.
00:07:52.080 Finally, the last question is: what made it special? What was something you walked away with that you didn't expect?
00:08:05.400 What made this event super special was that our team was small enough to bring the entire group to the event. Unfortunately, we enjoyed it so much that we decided to hire more people.
00:08:23.340 The downside is that it makes it harder to get everyone together now that the team is remote.
00:08:40.500 Having teams in person makes a lot of things easier.
00:08:52.920 Okay, that concludes the sharing time for now, but there will be more at the end of the session. Hopefully, you haven't used the little note cards on your seats yet.
00:09:04.519 Off-sites, especially for remote teams, are critical. They're super important because they create connection, bring alignment, provide information, and increase engagement.
00:09:22.920 This can be more challenging to accomplish virtually.
00:09:29.640 You need to deal with additional challenges, such as home interruptions, time zones, and distractions that don't occur in person.
00:09:48.240 Today, we'll cover ideas for both virtual and in-person off-sites, different components to think about when planning, and alternatives that cover the same overarching topics.
00:10:05.820 Here's the key point: when considering the differences between virtual and in-person off-sites, don't try to recreate an in-person experience virtually. Instead, think about the opportunities available to you because you're remote.
00:10:36.720 What are you trying to accomplish, and how can you achieve those same goals with a different approach? Today, we're going to discuss three key parts of planning an off-site: goals, logistics, and what I call the special sauce.
00:10:54.060 First, let's talk about goals. Knowing why you want to do something is very important. What does your team or department need right now?
00:11:12.240 An off-site can involve a number of folks, and there are huge differences in planning for an off-site with a small team versus a company-wide event.
00:11:32.760 An off-site can have more than one goal, particularly these days. You typically can't just fly everyone together for a casual hangout.
00:11:54.240 Even if you can, it's worth thinking about creating a purpose that digs deeper into why you want everyone to gather.
00:12:08.800 Perhaps the goal is to establish a team vision, improve personal connections, or share road maps and dependencies with other departments.
00:12:32.460 The structure of your off-site will depend on the number and type of goals you want to achieve, as you likely won't be able to address everything in a single event.
00:12:46.380 For example, it would be great to do a mini hackathon or establish buy-in around a team culture while aligning with broader company goals.
00:13:06.660 To prioritize effectively, think about what can be done asynchronously, such as in an hour-long meeting or a series of team meetings, and determine top priorities.
00:13:26.520 Critical to an off-site is taking your brain to a different space. Much like when we take a walk to think something through, distance from our work can lead to great insights.
00:13:48.600 Consider how long your off-site can be, and how often you plan to hold them. This helps to shape future opportunities for growth.
00:14:04.200 Also, think about who will follow up on action items after the off-site. Is it you, engineering managers, or volunteers? Knowing who will take on tasks is vital.
00:14:23.440 Ensure that this group has the bandwidth to accomplish the tasks soon after the off-site.
00:14:46.680 Next is logistics. Although it may seem mundane, smooth logistics can have a huge impact on the energy of attendees.
00:15:05.520 Logistics encompass the little things that take up mental energy. We have enough on our plates already, and making logistics easy is vital.
00:15:21.240 Today, it's crucial to simplify logistics so that attendees can show up ready to engage.
00:15:38.640 In advance, make sure folks know what to expect: the goals, agenda, breaks, and links to virtual platforms if you're accommodating different time zones.
00:15:56.520 Plan core hours and time zone-friendly sessions. Repeat similar content in different time zones so attendees can choose the time that works best.
00:16:10.560 It's good practice to highlight when certain time zones may miss meals, ensuring everyone is prepared.
00:16:27.120 If you’re planning an in-person off-site, coordinate arrival and departure times and suggest carpooling to make logistics smoother.
00:16:49.320 Make a packing list or note the weather to help prepare everyone.
00:17:09.300 Thinking through logistics signals that you care, and it can help get everyone into the right mindset.
00:17:19.680 For virtual off-sites, use travel days on Monday and Friday to prepare mentally. Encourage attendees to wrap up loose ends before diving into the off-site.
00:17:41.520 Provide practice tutorials for whiteboarding or tools that will be used during the sessions. Take some time to read pre-event materials.
00:18:04.500 Regardless of the format, successful participation requires different energy. Fridays can be a time for reflection, filling out surveys, or having casual chats.
00:18:24.600 An important aspect of logistics is ensuring that attendees are unavailable for the week. Set up emails or status updates to inform others about the off-site.
00:18:57.600 With ample communication, attendees can feel free to engage in off-site activities without worrying about outside distractions.
00:19:19.680 Finally, for off-sites to be memorable, they need a bit of special sauce, or 'sparkle.' Adding fun elements creates a lively atmosphere.
00:19:40.320 This special sauce can come in many forms and doesn't need to be expensive, just thoughtful.
00:19:51.720 I often incorporate gifts, experiences, and thoughtful facilitation during off-sites.
00:20:07.680 For gifts during virtual off-sites, I ensure that everyone has the supplies they need, as not everyone owns the materials.
00:20:25.080 I follow a formula that includes fun items, leadership lessons, and opportunities for bonding.
00:20:47.000 For fun, I've sent a whiteboard headband that also serves as a whiteboard, and many enjoyed using it during the event.
00:21:06.720 I also send children's books that teach important lessons. I like to include a character of color to promote diversity.
00:21:24.420 In addition, I've provided arts and crafts kits for creative breaks, which is especially beneficial for those with kids.
00:21:42.720 Snacks can serve as a great conversation starter, and sometimes I can budget for fun department swag.
00:22:07.800 I encourage an unboxing party at the start of our off-site to foster connection among attendees.
00:22:30.539 Now, let's talk about experiences. In-person off-sites often include engaging team experiences like volunteering or special dinners.
00:22:50.160 For virtual events, there are some fantastic options available, including Airbnb experiences, often across various budgets.
00:23:02.760 These types of experiences lead to inside jokes and increased camaraderie among colleagues.
00:23:25.560 Finally, engaging sessions through thoughtful facilitation are essential for effective off-sites.
00:23:44.160 If the off-site is filled solely with frontal presentations, it will likely not resonate with attendees. This is even more true for virtual events.
00:24:06.840 Thoughtful and engaging sessions encourage conversation. Use breakout rooms or interactive tools to stimulate participation.
00:24:24.720 For example, the balloon building exercise engages attendees while prompting discussions about team communication.
00:24:42.120 We also had a craft activity where groups worked together in breakout rooms to build designs, which encouraged deep conversation about teamwork.
00:25:06.900 It's vital to ensure varied voices and perspectives facilitate the off-site effectively.
00:25:23.940 We'll cover additional resources for facilitation, including the Luma Institute, which offers helpful tools, workshops, and articles.
00:25:43.440 Planning an off-site can be challenging. While logistical support is often provided, the actual agenda creation is usually on the lead organizer.
00:26:09.120 I’m here to help you determine what your team needs and assist in planning and facilitating the off-site to ensure productive outcomes.
00:26:28.680 So, what have we learned today? We've explored setting clear goals for off-sites, making logistics easy, and considering that special sauce for great experiences.
00:26:50.280 To conclude, please take a note card from your chair and write one thing you'd like to discuss or accomplish at your next off-site.
00:27:09.840 You will share this in a moment, so take around ten seconds to do this.
00:27:26.280 Now, find two other people with similar themes on their cards to discuss.
00:27:34.680 If anyone didn't get the chance to discuss, feel free to find those people later during the conference.
00:27:50.100 As you go through next week at work, think about the meetings you're in or leading. Consider what could be solved through an effective off-site.
00:28:07.320 Reflect on which meetings you stay engaged in and which you tune out to shape your goals better for the next off-site.
00:28:26.280 That's it, thank you!
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