Strategic Offsites: 5 Steps to Success

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According to Sun Tsu, the ancient Chinese military strategist, “Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat.”  These words were just as relevant then as they are now for today’s business leaders. If you’re worrying that your strategic plan is missing part of the picture, or that new entrants are gaining competitive advantage, you most likely need to step back and realign your strategy with the market environment. For many organizations, the catalyst of meaningful change is a strategic offsite.

With a little bit of planning and a few tricks of facilitation, an offsite can transform your business by (1) uncovering market misalignment, (2) finding new opportunities for growth, and (3) aligning your leadership team for execution. The secret of planning a successful offsite can be broken down into five simple steps:


1. Determine who needs to be there. A successful offsite/planning sessions should involve no more than eight people total. Ensure key departments, such as sales, marketing, product, technology and customer service are represented, but inviting too many people will likely impede any productive discussions. Attendees should be the decision-makers — any others who should have input can be consulted before or after the offsite session.

The last essential person is the facilitator, who ensures everyone is engaged, asks probing questions and keeps the agenda on track. If you need help with facilitation, you can contact me or my colleagues at Chameleon Collective to help.


2. Ensure the executives attending are prepared. Send your decision-makers homework in advance of the offsite. Everyone should review the most recent strategic plan and measure results against goals. You can assign individual executives to each of the following tasks: study the market, collect market feedback (from customer service, sales and/or even a survey), analyze the competition, update your product roadmap and map out your partnerships. The more thorough your prep work, the quicker your leadership team can dig in and take action.


3. Create a detailed agenda for the offsite. Two-day offsites are ideal: the first day  focuses on the strategic direction and the second day focuses on execution. But, don’t expect to leave the offsite with your strategy all wrapped up and ready to go. Ideas will still require vetting and refining outside of the offsite group, so the second day not only outlines a potential plan, it also assesses what’s missing and creates action items for finalizing the strategic plan.

Here is a sample agenda that I’ve used in the past:


– Team Introductions

– Review Current Plan

– Market: Competitive Analysis

– Market: Environmental Scan – Where is it going in 1 year, 3 years, 5 years, 10 years?

– Alignment with the Market – How do We Win?

– Discussion on Organization

– Evening Team Building Activity



– Thoughts from Yesterday

– Product Roadmap Analysis

– Review Partnerships

– Review Budgets

– Goal Setting: Converting Strategies Into Company Goals

– Implementation Plans

– Individual Goal Measurement

– Communication Plan

Every agenda item is pertinent to the end goal, but staying on track throughout the day, with so many analytical minds in the same room, can easily be a challenge. Mitigate the chances of disruption by allocating specific times for each topic and, of course, include short breaks for relaxing, resetting and returning calls. Just don’t make the breaks too long so people get completely distracted with other priorities.

Your agenda should also incorporate multiple methods of engagement to ensure everyone on the leadership team has a voice. Some parts of the agenda can be an open discussions, with others better suited to small groups for more productive and cohesive brainstorming. And you’ll never know when arts and crafts may be needed — bring along some supplies, like stickies, in case you need to have a vote or discussion that requires individual, versus collective, opinions. If you know of any communication styles your executives prefer, find a way to incorporate them so all voices are heard and can relate their ideas in an effective and productive manner.


4. Plan what you want to get out of the offsite. Leave your offsite with plenty of ammo for the next phases, including strategic recommendations, clear action items (each with its own accountable party and due date), and an internal communication plan. Since it’s difficult to finalize your strategy without market and team input, the action items should cover the steps required to quickly research and vet the collective recommendations. People will also want to know what transpired over those two days outside the office, so the attendees need to be prepared to disseminate a cohesive message about the progress, even if the full strategy is not yet finalized. Your communication plan should encompasses instructions for both managing up (e.g., board, corporate management) and managing down (e.g., employees, team).


5. Set up accountability and support. The work only begins at the offsite. Before leaving, schedule a weekly touch-base meeting with your leadership team to track progress of action items and address any impeding issues. Within 30-45 days of your offsite, you should have a solid draft of the core strategy that can be presented to the broader stakeholders and team.


If set up correctly using this recipe, your two days away should be a productive and effective reset button for the entire team. Skipping the offsite is not an option. In today’s dynamic, rapidly changing market landscape, the only way to win is to constantly re-evaluate your strategy based on where you think the market is going. This means doing a deep dive at least once per year with lighter quarterly reviews.

If you’re putting this off because you don’t have time, give us a shout. Chameleon Collective has a strategic assessment and planning program that can easily help. We’ll manage your strategic offsite from concept and planning to day-of facilitation and post offsite execution.

Let us know if we can help, and may your next offsite be a huge success!

About the Author:

Veronika Sonsev is a Partner with Chameleon Collective and also an advisor to a number of startups. She works with B2B clients in retail and digital media to help them accelerate revenue through strategy, marketing and business development. Prior to Chameleon Collective, Veronika founded and ran inSparq (acquired by Adiant Media), a software company that worked with some of the largest retailers and brands to market their trending products in real time.  She has also held senior leadership roles at Jumptap (acquired by Millennial Media) and AOL, and has experience launching to international markets, building new business lines, and developing strategic partnerships. Clients rely on Veronika to help them develop strategies for growing their business, tell their story in a way that gets customer attention, and secure those all-important deals to help their businesses scale.

Veronika is an active advocate for women in business, and in 2009, she founded the global non-profit Women in Wireless, which now has over 12,000 members and 10 chapters around the world. Her success as an entrepreneur combined with her support for women in the digital industry has led Fast Company to include her in its League of Extraordinary Women and TechWeek to name her as one of the Top 100 digital leaders in New York.

Veronika holds a B.A. in Economics and Russian Studies from American University and an M.B.A. from the Wharton School at the University of Pennsylvania.  You can find Veronika on Twitter at @vsonsev and on LinkedIn at

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