• Ariana Friedlander

A Virtual Success

How do we have productive, strategic conversations when we cannot retreat in-person? That was the question my client and I were discussing. Despite the fact that COVID was making it impossible for his team to hold their strategic planning retreat in-person this year, he felt it of the utmost importance to still hold the retreat virtually.

It was a bold decision. For many leaders, the disruption to work caused by COVID has resulted in them hitting the pause button on such efforts, waiting until life gets "back to normal." Doubting that a virtual meeting can allow for the same quality and depth of an in-person conversation, they skate along focusing on the urgent.

And it's not that one way is right and the other way is wrong. A leader must always be attuned to their team, aware of when to push them and when the focus is on getting by day-to-day.


As one manager I spoke with said, "We've been in crisis-crisis mode. I'm looking forward to just being in crisis mode when we can focus on stepping back and looking at the big picture again."

But it is important to be aware of the story you are telling yourself. Are you waiting to step back and look at the big picture together because of severely limited crisis-crisis bandwidth (in which case there's usually also tremendous doubt that your business will even be around in a month or two) or due to the belief that it's not possible to have these types of conversations as a team virtually?

If it's due to a limiting belief that's very problematic. A leader must model adaptation and flexibility to their team, which requires an awareness of the stories and limiting beliefs being clung to.

For this client, he understood that there were ways to both adapt to the present circumstances while bringing his team's focus back to the big picture. That while 2020 was not going according to plan, he could still remain true to the essence of his vision for this year and the values that guide them.

For him, realigning his team to the big picture was an important aspect of adapting to meet the dynamic changes unfolding before them this year. As an internal service provider, it's easy for his team to get pulled into the urgent yet unimportant tasks others are struggling with. The projects they are responsible for stewarding have major consequences yet often take a lot of time to plan and implement making it easy to perpetually push them to the back burner.

So, we explored the question - How do we have productive, strategic conversations when we cannot retreat in-person?


Like any well-run retreat, the answer came down to preparation and appropriate use of the tools available. I worked with a design team using my co-creating retreat experience process. And because this was a first for the team, our preparation took a bit more time and effort.

That is where a lot of leaders lose momentum with their teams, assuming that preparing for a retreat is as simple as drafting an agenda. And with the added layers of retreating virtually instead of in-person, there is so much subtlety and nuance that gets lost with insufficient preparation.


We not only wanted to gather input from team members as part of our preparations, I needed them to train me on their internal systems for virtual collaboration. With their input, we co-created the why and the what as usual but with meeting virtually, the how took on extra dimensions that required the design team to make intentional decisions.


Whereas before, the decisions about how were pretty clear cut, now we had to take into account new limitations. Based on my experience facilitating virtual meetings, I advised we do small group discussions to ensure the conversations had the depth and engagement necessary. But their platform of choice doesn't do breakout rooms like Zoom, so we had to figure out a workaround.


We couldn't take notes via a whiteboard or flip chart, so we had to identify a way to capture notes from the retreat that were visible in real-time to everyone and available in one place. So, we used a PowerPoint deck accessible on the cloud for providing direction on activities and documenting ideas and decisions.


And perhaps one of the more challenging aspects we had to figure out was how to have fun virtually. In years past we did things like play yard games and have catered lunch (great food is often one of people's favorite parts of any well-run retreat) but those things only work in-person. So to add to the fun element, we got out noisemakers to celebrate wins - this was an opportunity for people to get really creative while learning more about each other - one team member used their talking robot!


And throughout the retreat, we had a GIF competition. The GIFs provided levity and related to the discussions being had so they weren't a separate, and distracting chat which sometimes can happen. The winner of the GIF contest received a gift card.


It turns out that meeting virtually doesn't mean we can't break bread together. Everyone was given an allowance and encouraged to use NoCo Nosh (a local restaurant delivery service) to order the lunch of their choice. As a result, everyone got exactly the lunch they wanted, which is a sure recipe for a happy team!

As we debriefed afterward, this is what the client said, "I am very happy with the results from the retreat! The team seemed to be engaged for the majority of the event and I think folks got a lot out of it. Our newest team member was very impressed and felt very involved despite being only a few days on the job."

In other words, the retreat was a virtual success!

So, if you need to get your team's input on the big picture but can't retreat in-person, know that it's still possible to engage in these high-level conversations. With some preparation, expert facilitation, and the proper use of the tools at hand, you too can have a retreat that builds camaraderie, gets your team all working together towards a common goal, and goes better than you ever expected possible.

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