Why should I have an Offsite today?

Right now, at the end of the summer, just before the holidays, the Q4 of 2022 begins, followed by 2023 coming in a storm, we have all already felt the current crisis in one way or another — recruitment, layoffs, cost of living, August…

This is exactly the time to look and gather inward in order to expand outward.

This is true for entrepreneurial teams, management teams, VC’s partners, and also for you with yourselves.

Why and how Offsite can strengthen leadership, communication and a sense of ownership among founders?

There are different types of offsites, which as they are called – are out of the ordinary, something different from the routine. Some aim to produce team building and fun, and some aim to strengthen relationships, produce work plans and converge in favor of a specific challenge that the team is required to address.

In recent months I have been able to lead a number of offsites with different startup teams in different stages, with the aim of strengthening the relationship between the founders and producing a different type of business strategy.

Here are some thoughts on how I experienced it from the-most-inside-of-the-outside:

  1. Offsites allows us to make a pause – stopping the stress and the noise, a break from all the storms and roller coasters that we experience in our business and personal life. This will usually be forced, but it’s not necessarily bad. Sometimes we’re not strong enough to stop ourselves and need a summon in the calendar.

Here and now – offsites allows us to take a breath and draw an area where we’re present only in what’s happening here and now, not everything that’s happening around us, not worrying for a moment about what will be in the future, but giving space to what’s happening here in our interaction between us.

  1. The very act of stopping and being present allows us to bring to the surface a new mental layer, a more emotional discourse, that is sometimes difficult for us to produce on a daily basis with all the fast pace around us. We need to put in this unit of time, the attention and the focus to be able to observe what we’re going through and what we’re feeling. This conversation, which we often don’t allocate enough time resources to, is the most important thing there is.
  2. The ability to flow within this pause. What does it mean?

As the one who leads and manages the offsite, there is the prep part, where I coordinate expectations with the entrepreneurs in advance, hearing what’s important to them and what they would like to achieve through this – the offsite’s goals. From those goals I create the flow I think is right in order to achieve the desired result. But, in offsites as in life itself, alongside the initial plan we need to stick to, it’s not less important to make the space, to listen and allow new things that emerge from the plan, and move within that. To go with the flow. Using examples that emerge from the discourse and experiences and direct them to the right directions. So for any good plan, there’s also plan B, which is listening to what’s happening in the moment of truth and navigating it. In fact, the better the plan, the simpler it will be to steer and navigate the surprising reality from a place of strength and security.

An offsite has several stakeholders: on the one hand, the people for whom the offsite was made for – it could be co-founders, management team, product team, the organization’s leadership. And there are those who are facilitating the offsite, for that matter – me (and when CEOs do it even in their professional team meetings — then they themselves). 

It’s important to give space to how we look at the situation, how we can come mentally prepared and how we also check with ourselves afterwards — what worked and what didn’t, and what we take from it to the next time. Where we intervened just in the right amount, where we created a pivot in the conversation, where we drew a boundary, where we took additional roles to reflect a certain angle to them, where we had to put a different emphasis, and where we were able to help the progress of the people for whom the offsite was. Internal questioning and learning go in all directions.

Setting – In psychology it’s known that a very significant part of therapy is the setting – what the room / space looks like, what’s the environment, where is the right sitting place for creating a feeling of security and comfort, boundaries – a framework. Part of what’s beautiful and fun about working with startups, and yet not easy to contain at all and even challenging, is the need to know how to flow and navigate in situations that are unknown. Just like them.                 

For example, in the last three offsites, I found myself in three different locations in the world that even though I was in before, I didn’t know what specific physical environment I was coming to – I didn’t have the option to preliminary tour the locations and the entrepreneurs were more dynamic and less planned.

I had to flow with the situation – to own it, and know how while moving and spontaneous location changes – to manage the times, the goals, the conversation, the exercises, the breaks, the nerves, the arguments, the anger, the joy and everything within that flow. It’s very similar to what happens to us at work and everyday – we have meetings that in many times are in changing and in unknown settings, and many times there are disruptions and a roller coaster of emotions and this is reflected in our ability to conduct ourselves in an environment that is VUCA – Volatile, Uncertain, Complex, Ambiguous.

And it requires us as entrepreneurs to constantly conduct ourselves in two dimensions at the same time – to be present in what’s happening and listening to the situation, and in the same breath to look at ourselves and see how we understand the situation, how we navigate and manage it, how we flow in it in the right direction. And this is a very important muscle to train for entrepreneurs – to adopt these 2 perspectives and move between them. The entrepreneur alongside the founder and the leader that all exist within us.

  1. Enjoy it – to have gratitude along the way, cherish that our work brings us to wonderful places, constantly takes us out of our comfort zone, and allows us to grow. It can be in any role and in any capacity, it’s just a matter of how we choose to experience life and the situations we’re in and see the beautiful moments, alongside the challenges. This requires constant work on our mindset.
  2. Visual and experiential anchors – an offsite will usually be conducted in places that are not standard. And there – it would be right to see how we can use the environment within the managerial situation and what we want to bring from the visualization in favor of conveying the message. For example, at the last offsite we found ourselves sitting in a wooden house in a stunning hotel in a coastal town in Europe, sitting on bean bags that we brought spontaneously, the sea in front of us to the west. And this view summoned us to a special atmosphere that made me open the offsite in a mindfulness session of a few minutes, before we dived in, to relax a bit from the stress and complex feelings that were in the air. The end of the session was when I looked up and noticed the amazing tree we were literally sitting in, a beautiful bloom of thousands of green leaves in lots of shades and colors – I took that stunning image into our discourse and asked them at the end “What pops out of this tree in their eyes?”. And each answered from his own unique perspective: “The variety of possibilities and opportunities they have to move and grow out of the situation – fifty shades of green”; Someone else saw – “the sunlight shining through the leaves” and likened it to the positive direction they had opened up through the offsite.

Using what’s in our environment, and most definitely in nature to put it into the session, into the presence, into what’s happening – also really connects people, gives them some grounding and helps them a lot.

  1. Structure – an important thing to pay attention to in my opinion, is to the structures of the sessions, how each session should stand on its own two feet, and even if there are nerves, pains and conflicts – the next session always opens ‘Tabula Rasa’ for it to be effective.
  2. Equality in conversation – another thing that needs to be noticed is how all those who are present get an equal space to speak, that no one takes over the conversation, and that everyone can express their opinion in a balanced way. It’s our responsibility as those who lead the discussion to see and pay attention to this. There are those who will not take the right to speak and need to be helped to get to the front of the stage.
  3. One of the most important things, at the end of each session and at the end of the one-three days offsite, is to reflect on each situation on what worked, what didn’t work, what to take on, and how you feel – because no situation is similar to another, and we need to bring this variance into the discourse, in order for us to internalize it. Only from this feedback do we all learn and get better.
  4. Post offsite – As I opened at the beginning that the offsite allows stopping and connecting to some more emotional and feeling based layer that manages us, it’s not less important that the offsite conclusions and results are maintained through an ongoing routine that we continue to sustain – once a week / two weeks / month, so we have the environment and place to continue the discourse, to preserve the mental health that nourishes our physical health, to continue forward and not pressing the gas while in neutral.

From precisely these areas, fertile ground is made possible for effective action.

Go have an offsite. Now is the time.

Are you convinced?

Pin it in the calendar.

About the Author
Gali Bloch Liran is the Founder & CEO of The Human Founder; Executive Coach & Startup Advisor; Entrepreneurship Lecturer at Reichman University; Host of The Human Founder Podcast and an Author. Gali is a certified Executive Coach working with CEOs, startup founders & VC entrepreneurs & Investors, helping them gain focus, manage their day-to-day challenges, develop their leadership skills, psychological resilience, and work-life balance required to scale a venture sustainably.
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