The Ultimate HR Director's Guide to Offsites: Maximising Team Potential and Engagement

How are high-growth companies leveraging offsites to enhance HR strategies and employee engagement?

The role of the HR and People Director has become increasingly expansive in recent years as it take on more business strategy, which presents exciting opportunity and challenges!

Context: The Evolving Role of HR Directors and People Directors

In today's dynamic business environment, HR Directors and People Directors play a critical role in shaping the workforce and culture of high-growth companies. These leaders are at the forefront of navigating challenges such as remote work trends, the shifting economic landscape, and the integration of AI in the workplace. Their position demands a versatile approach, drawing from a diverse skill set to foster innovation, ensure employee well-being, and drive organizational growth.

Phew! That’s a lot.

There are many new pressures defining the CPO or CHRO role, as discussed in the highly acclaimed episode "The first 6 months as a CPO" from The Modern People Leader podcast. Featured in this episode is Q Hamirani, a former Airbnb executive and current Chief People Officer at Paper, who also serves as an advisor to WorkTripp.

So, the starting point of this HR guide to offsites is first of all to salute the collective wisdom and diversity of HR and People leaders, all of whom do an incredible job to align and grow their organisations on a daily basis. 

Offsites as a Strategic Tool for HR and People Directors

The TaxScouts Offsite: a chance for deep discussion and human connection

Given this backdrop of volatility, why are offsites increasingly becoming a strategic tool for HR leaders? 

Many of the HR and People Leaders we talk to are working in extremely fast-paced environments, with scaling teams internationally. The organisation can no longer rely on the trust and alignment of the original core team steadying the wider ship, and they are likely operating in some form of distributed model of work. 

In an environment where the dynamics of teamwork and collaboration are continually evolving, offsites offer a unique opportunity to bridge gaps, enhance communication, and build a cohesive company culture. 

(The best-distributed teams in the world understand the need for a new model of work which balances convergent and divergent modes of working.)

For example, Atlassian employs a hybrid model, using offsites to bridge the gap between remote employees and those in physical offices, enhancing collaboration across its distributed workforce; Buffer’s offsites and retreats are central to bringing their global team together, showcasing the company's commitment to team unity, and Zapier's regular offsites and retreats are key to their success in team bonding and collaboration. 

These gatherings go beyond mere team-building exercises; they are a testament to the belief in the power of bringing people together to achieve greater alignment towards the company's vision and goals whilst still accessing all the benefits of distributed work and access to talent.

In academic speak, "Effective global virtual teams engage in a deep rhythm of face-to-face and less intensive communication, leading to improved outcomes." - M. Maznevski, K. Chudoba 📢

In common sense speak, this just means sometimes we need to be in heads down execution mode and sometimes we need to slow down to speed up, and to connect in-person as a team, to muddle through the big ticket items.

Budget & the ROI for Offsites 

(Research by Kneeland & Kleinbaum (2021) underscores the transformative impact offsites can have on team dynamics, notably in fostering network tie formation and enhancing collaboration across dispersed teams.)

But, if one of your tasks is getting your offsite plan past a finance head who might be thinking this is all a bit “fluffy”, listen up; many of our customers are reviewing operational cost in tandem with team benefit. 

We are working in times of extreme volatility: the climate-crisis, wars, AI disruption, a shift from growth to profitability. 

Distributed working is a direct response to that. Allowing for operational agility at a time of rapid pace of change. 

For example, one of our customers, with under-utilised office space, gave up its WeWork leases and switched to flexible desk passes & a year-round offsite plan, using WorkTripp to deliver x6 offsites globally, saving an estimated £800k. 

Or check out this case study from Chase Warrington:

A COO recently challenged me on our investment in co-located team gatherings (retreats/offsites), citing that this goes against our remote-first approach to teamwork and that the high costs of bringing people together surely produce a negative ROI.

I responded by sharing some data from a recent survey, where my teammates reported the following after attending an offsite:

- 92% felt more connected to their teammates

- 94% felt more aligned with our vision and path forward as a company

- 95% felt more enthusiastic about working for Doist

If that's not worth investing in then I'm not sure what is - but I can guarantee ping-pong tables and happy hours won't achieve those results.

He was still not convinced, so we went deeper and calculated the actual tangible costs

- He's spending $11k/person/year on office space that is 60% occupied, while his team is begging for more flexibility and to lift the mandate on in-office days.

- We're spending $4000/person/year bringing our fully remote team to retreats attended by 95% of our employees, and who have voted almost unanimously that location independence + 2-3 meetups per year is ideal for their productivity and work-life balance.

This was before we got into employee attrition rates, re-hiring costs, access to global talent, and satisfaction/engagement scores.

In short, think about how the cost of your best performers leaving, or your strategy not being fully understood when it comes to execution. Would you spend a % of that overall cost to ensure its success?

When it comes to budget, it definitely depends on the size and seniority of the team (ie All Hands vs management team), length of stay and where you go. 

For senior leadership, you’ll be looking at around $1500 per person(will give you budget for nicer venue and coaching support), $500 per person for 'manager' groups of 25-50 people (to include mid-level accommodation, workshops & local activities) and $250 per person for All Hands events (depending on whether you want to stay over, share accommodation etc) - all excluding travel costs.

This is for one offsite. At WorkTripp, we think about creating a new cadence of connection with a mix of teams and we create our clients a year-round connection plan suited to their needs…

But beyond all of that, as HR directors you’re always thinking about attracting and retaining the best talent and positioning your employer branding.

We all know that distributed and flexible work still reduces the regrettable churn of top talent, and reduces salary costs. 59% of millennials and Gen Zs prioritise remote work in their job search and these are the future leaders of today and tomorrow. 

Offering an employee experience which delivers learning, in-person connection and flexibility can help you achieve your talent plans economically.

Make it stand out

A recent job ad highlights the yearly retreat as one of the employee benefits of working at the recruiting company, as seen in The CultureAmp People Geeks Slack community

Some leaders will attempt to craft in-person connection through RTO mandates. This will have limited success as after a year of RTO experiments, productivity has remained flat.

Others will use their office footprint more intelligently using hybrid models like Bloom and Wild’s squad assemble sessions which combine remote and in-person with office time.

But many of the companies we speak to are fully-distributed and then use offsites to craft that in-person time.

(My favourite recent example is Sasha Haco, who featured on BBC Radio 4 last week about her journey as co-founder and CEO at Unitary - an amazing multimodal approach to harmful video content moderation. Unitary has raised $25m and has team all across Europe. They are scaling through a winning remote-first work model for a wider talent pool and strategic quarterly offsites to build a connected team.)

Introducing the Ultimate Guide for HR Planning Offsites

With that all said, this guide is designed to provide HR Directors and People Directors with comprehensive insights and practical tools for planning and executing impactful offsites. From selecting optimal locations to crafting agendas that resonate with both corporate and employee needs, our focus will be on maximizing these events for profound organizational and personal growth.

1.How to get started. Avoiding the offsite overwhelm

An offsite isn’t complicated but it is complex. Avoid the overwhelm by

a) working with an ops ninja colleague - or an external partner - to get things done and

b) breaking down the to-do lists into manageable tasks

We’ve helped you get started with our offsite planner. Simply enter your proposed offsite dates and voila! You’ve got a series of task deadlines to work through so you don’t forget anything. 

2.Strategic planning and goal alignment

Understanding the importance of aligning offsites with company and team goals is paramount. For example, strategic planning offsites provide a unique opportunity for HR leaders to step back and align on long-term human resource objectives. This section will explore how to tailor offsites that align with broader company goals while also addressing specific HR strategies such as talent development, leadership training, and succession planning.

(Don’t get trapped by starting with logistics first and losing your goals in the process).

At WorkTripp our Future of Teams™ methodology synthesises the top academic research into team behaviour and performance to understand the critical factors for team success in the new world of distributed work and personalise offsite programming accordingly.

Each factor is connected and sequential: trust is critical to having uncomfortable conversations; and we can’t solve problems effectively unless we’re aligned on the goal.

That’s why we help HR Leaders to understand their goals for connecting their teams before they even start thinking about where they are going or other logistical questions. 

For example, with TaxScouts - a high-growth FinTech - with a new CEO and new mission and vision, the goal was for the team to connect and understand the big picture. In addition to helping them plan and book their offsite. We were able to help them identify double-digit increases in all six traits related to high performance as well as +76 ppt in familiarity of the team and +40 ppt in clarity of values. 

So, what are the reasons you are gathering your team? Get this nailed before you move on.

3.Building trust and enhancing team dynamics

At the heart of every successful offsite is the enhancement of trust and teamwork among participants. Why is this so important?

Anyone who knows their fundamentals about high-performing teams (see Amy Edmondson, Caroline Aube ́ Vincent Rousseau and Patrick Lencioni) will know that trust and psychological safety is the basis of anything epic happening in the workplace. Toxic drive can only get you so far. Then everyone burns out and the whole thing falls over. Indeed, Slack hit the nail on the head with their new research which revealed that “trust is the key driver of productivity” and that people who don’t feel trusted are far less productive, two times more likely to leave, and far less likely to put in "extra effort".

And psychological safety famously comes up as the most important factor for team effectiveness at Google. In the context of distributed teams this is even more heightened and more conscious work needs to be done to engender trust to unlock our most fantastic work. 

Indeed, McKinsey’s report on psychological safety and leadership identified that there were significant competitive gains to be achieved for team leaders that invested in “leadership-development experiences that are emotional, sensory, and create aha moments.”

And the Chartered Institute for Professional Development recently listed quality in-person team building as the number one intervention to build a high-performing team within the context of remote work being more prolific (“increasing team building activity…focused on helping people to get to know each other and build social ties”). And, the World Economic Forum and Harvard Business Review listed distributed work + offsites as one of their 5 office work trends that will define 2024. 

The most effective team-building exercises create an environment where open communication and trust can flourish. From fun team-building activities in London to leadership events that challenge and grow your team's dynamics, the focus should be on creating lasting bonds.

"The teams where I felt most seen... have been where the leader of that team has committed strongly to offsites and the idea of gatherings" -

Tom Hall​​, GM, Lego Education International on The Future of Teams Podcast 

When we come together, we open up more. We enjoy synchronous moments in an asynchronous world, inspiring a sense of belonging to the same tribe, tackling the same problems. This is extremely powerful in guiding us in the same direction. Don’t be tempted to ignore this by thinking of this aspect as “just a social.” Really lean into authentic experiences which connect you.

4. In a rush? Don’t forget the offsite agenda

Knowing how to build an impactful agenda for an offsite isn’t something that comes naturally to all of us.  

All too often, there is usually an internal catalyst which means organising the offsite suddenly becomes a top priority and the focus falls on the logistics of booking the venue and sharing the comms with your team.

But what’s the point of all this investment if you haven’t spent time on the programme? 

Think about a mixture of time to share or co-create the vision of the company matched with at least or if not more time for the team to actually connect and create those all important authentic moments. This could be sharing food, hiking, or co-working on a passion project together.

Remember optionality! The best leaders have always sub divided their teams to avoid groups becoming too unwieldy. Theirs no reason for everyone to all be doing the same thing at the same time all the time. Allow teams to split up into different activity groups, and benefit from the buzz of sharing when you recombine.

"Sometimes some of that time is just spent they just want to sit down and code next to each other and that's fine. That builds those connections"

Stephen Janaway​​, VP Engineering, Bloom and Wild on The Future of Teams Podcast 

"Encouraging employees to do someone else's job on those offsites worked really nicely for culture building and also for generating new innovations"

Sarah Ratner, former COO of Lendable on The Future of Teams Podcast 

(If you are in a rush, our Future of Teams™ methodology matches your team goals to a ready-made editable offsite agenda and survey set so you are good to go within 24 hours.)

5. Choosing the right location & venue

Whether it’s the vibrant streets of Berlin, the serene landscapes of California, or the historic charm of New York, selecting a site that resonates with the company's culture and objectives is crucial. At WorkTripp, we guide you through evaluating executive offsite locations, corporate retreat locations, and how to book team offsite venues that align with your vision.

Our ethos at WorkTripp as a pending Bcorp is to select venues which allow for time in nature to help your team get into that “slow productivity” mindset and connect to the world around them.

This aspect can be a real time-drag, so consider working with a partner or platform to get you more quickly to your ideal spot.

“I saved at least 70% of the usual time I would spend using WorkTripp. It helped me to create a vision for our offsite, to understand the goals and create a plan from there.”

— Paola Tartaglione, Head of People | TaxScouts

Want some inspiration on venues?

6. Maximizing ROI: the Post-Offsite Follow-up

Investing in an offsite is an investment in the company's human capital, from the immediate benefits of improved collaboration and morale to the long-term impact on company culture, decreased turnover and improved employee engagement

Measuring the impact of that spend is important so you know what worked and what to focus on in the next few months to keep the momentum up.

Our measurement approach measures the underlying traits of hgh performance teams, as well as the specific goals of the teams getting together. We always advocate for a post-offsite connection plan to ensure those all important new ties keep engaged until the next time!

Like this guide? Thanks for reading!
Please consider sharing it with anyone you think would benefit :)

Shout out to our friends at Elevate HR, and People GPT for supporting all the amazing HR and People Leaders out there!

(Want more inspiration? You can listen in to more leaders on our Future of Teams Podcast here.)