Creating Strategy with a Remote Team

creating strategy with a remote team team anywhere leadership podcast episode 16
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Today we speak to Tara Rethore, about leadership strategy development for remote teams. Tara is the CEO and Strategic Advisor at Strategy for Real on how to create a remote team strategy. First, she explains how to utilize the mindset of taking a company on an adventure in a strategy retreat. Then, she describes the keys to preparing for and leading a successful remote strategy offsite and a secret high tech tool that she uses to keep her teams engaged.

As a result, her mantra, which I think we all need to adopt, is to Be Open to Ambiguity…something we all need in these times.

Because of the changes in work we’ve experienced this year, leadership strategy development is different on a remote team. In-person Strategic thinking benefits from the energy in face-to-face interactions. In fact, leaders have to avoid the mistake of copying and pasting the strategic planning process that they do in person and think it’s going to be successful online. Given that, in-person strategic planning won’t achieve the same results on a Zoom call. For one reason, it’s because it’s harder to read the room on a video call. Another reason is that video calls are extremely exhausting compared to in-person meetings where the strategic planning process balances the exhaustion with building energy. 

Strategic Planning Process:

Leaders have to look at leadership strategy development with a strategic planning mindset and consider the balance of what needs to happen in person, what can happen online, and when to have breakout rooms and personal work. The strategic planning process is really an art now with so many dynamics to consider. Tera says it’s especially important to look at the whole, plot it back, and get the right people in the room.

Strategic Planning is An Adventure

  1. First, you must think of planning for your strategic plans as a production. 
  2. Second, how do you engage the members?
  3. Next, what are the different steps along the way?
  4. Finally, make sure you have a backup plan, in case you are confronted by a wild beast. Be flexible and able to pivot, switch or move, consider calling it early, or regrouping when needed.

Leadership Planning Development with the 5 W’s

WHY-  Identify the End Result

In order to plan the most effective strategic planning session, start with why. Why are you having this retreat? What does a successful retreat look like? What are you trying to achieve? What do you need to resolve to be successful? Who or What might get in the way? What would it take for them to say yes to this? What would it take for this day to be successful? 


Who are the key players in this process? What is their most important part?


When creating a remote team strategy, leaders must ask, “what is the outcome we are trying to achieve?”

  • What can you be doing to save the conversation in advance? Don’t focus on sharing information but on processing that information and defining clear outcomes. 
  • During the strategy retreat, what tools will you be using? 
    • Flip charts during in-person meetings – encouraging people to write their own notes- on paper, and share them on the screen, take pictures of what they’ve written, get a picture of what’s going on in the room 


Keep it simple: 2-Day Intensive Retreats need to be broken down and simultaneously energizing. After all, remote strategy retreats are only exhausting, they don’t replenish the energy like they would if you were in-person. So you need to break down your strategy retreat into bite-sized chunks. In that case, you can consider replacing a 2-day Intensive with a Strategic Planning Week.

When will we meet? How frequently? For How long? How can we break this down into smaller bite-sized chunks?

Elements of Planning for Strategic Planning Agenda

  • Pre Work
  • In Meeting Work
  • Group Work
  • Buddy work
  • Homework


In your remote team strategy retreat, Who will meet in person? Who will meet online? When will the meeting be Hybrid?

  • Having someone on the phone for the entire strategic meeting doesn’t work. In this case, video calls work better, keep the video on.
  • Another example is to consider a smaller group of people attending in person and have the subject matter expert on call and bring people in as needed. 
  • Are we in a better place to think about having remote team strategy meetings at home? Does it spur more creative thinking? Is it a production? 
  • What’s the desired outcome? Who’s needed so that you have a chance at reaching that desired outcome? Put those people in the room. 
  • Characterize the work: Which pieces of this strategic thinking planning/thinking most benefits from that interpersonal interaction. Not everything you’re doing in a strategic thinking/planning session has to be in person. If you’re doing breakout groups in person, you can do those virtually, but consider doing them on different days, grouping them with different groups of people. 

BONUS: Remote Strategic Planning Team Building Idea

  • Replace meals you typically have in person at your strategic planning meetings with ordering meals and sending them to everyone’s houses so you can all have a meal together online. 

BONUS: Up Your Remote Team Strategy Retreat with This Skill

Consider hiring a Graphic Facilitation Designer to up the game during your next strategic planning retreat. 

Executive Leadership Round Tables

  • Insights with CEO’s and executives who value peer insights and make the time to think differently about their business. These leaders know that right now they have to be deliberate in nurturing connections because we’re not just running into people like we used to. These leaders show up with questions and challenges.
  • What’s on the minds of CEO’s right now? 
    • CEO’s are wondering, how do I lead?
    • How do I get connected?
    • How can we create a virtual water cooler again?
    • What is this pandemic teaching us about our culture and what do we want to preserve?
    • How do we budget for next year, since last year was completely different than today?

Messages for Leaders:



Get out of your office whenever you can.

To learn all the details of leadership strategy development, listen to this full episode.


How to reach Tara Rethore:

Strategy for Real

Linked In


Lizard Brain Solutions, Brian Tarallo

Online Courses for Leaders Leading a Team From Anywhere:

Check out these online courses for remote leaders from the Team Anywhere Team.

How to Be an Effective Remote Manager | How to Build Virtual Accountability

Strategic Planning Quotes

  • leadership strategy development
  • leadership strategy development
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  • leadership strategy development

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This episode is brought to you by Marymount University, School of Business and Technology: innovative solutions up-skilling for the what’s next economy. Oyster Organizational Development dedicated to higher performance, business success, and leveraging team. And Wejungo designing customized talent acquisition solutions.

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