Strategic Offsites: 5 Steps to Success

Strategic offsites are important for the health of a company. When done right, an offsite establishes a market position, internal alignment on a vision, and actionable steps to making that vision a reality. We asked expert Veronika Sonsev from Chameleon Collective for advice on how to plan a successful strategic offsite. If there's a strategic offsite in your future, this is a must read because her simple steps will make a big difference... 

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:


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 [www.chameleoncollective.com] to help.


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.


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.


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).


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 [www.chameleoncollective.com] 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!


Veronica 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.You can find Veronika on Twitter at @vsonsev and on LinkedIn

Checklist for Planning Your Next Corporate Meeting

If you’ve been tasked “planner” of your next corporate offsite or meeting, use this checklist to ensure that your event is on brand and set for success.  


Determine the main goal of the meeting. A good (and quick) assignment for each member of the offsite committee (yes, have an offsite committee!) is to list the following in the order of priority:

  • Educate - something new is being introduced that needs everyone’s attention and participation
  • Motivate - heading into a busy selling season, it’s time to get the team working together to meet the company goals
  • Celebrate - huge wins, high fives for bringing home the gold


Identify what would best reflect the brand, the company culture and the goal you’re setting out to achieve. If the sessions are long, consider the furniture to make sure the seats are comfortable and set up to support the meeting goals (i.e. education = classroom style). Looking for site inspiration in NYC? We have you covered!


One that will remain on time, with Q&A for each session and has time for socialization and discussion built in. Assign someone to capture the key take-aways to recap/share at the end of each day.


Ensure that your menu has variety and healthy options, including good snacks. Is there a celebration one night? Consider a more substantial breakfast for the next day. You can also add items that reflect your brand. I.e., if you have a red dot in your logo, red sour candies in clear vases can decorate your tables.


Is it easy to use and ready for all participants? Plus the smaller touches - Soft-talker? Get a microphone. Screen not visible from all seats? Get another screen and / or reserve the “obstructed view” for support staff. Powercords? Get more. You don’t want participants sitting on the floor. Wifi? Make sure it’s strong enough. It’s the #1 complaint of most conferences.


Create a survey to be shared at the completion of the meeting. Include general questions to capture any culture shifts. Some good questions include: I have confidence in the future of this company;  I have confidence in the leadership of this company, etc.


Think of ways you can make participants more comfortable throughout the meeting. Create a “running club” for the mornings or secure spots at the yoga studio nearby. For the person who has to get to the airport before the meeting ends, have a car service scheduled, space to store their bags and a to-go bag with food for their trip. 

Taking the Team Meeting Offsite in NYC

Conference rooms are booked. Teams are taxed. Companies large and small are breaking away from the expected to spark team creativity! Check out these unique NYC offsite locations, hand-picked by our friends at Splacer, ready for you and your team to tackle your next challenge.  


A space for those with real taste. This one-of-a-kind culinary museum located in Williamsburg/Greenpoint offers 20-foot ceilings, industrial details, and a unique collection of scientific gastronomic gadgets. It’s the perfect spot to throw a sweet event.


Just North of Grand Central Terminal, catch spectacular views, elegant lighting, and a modern inspired café at this reinvented Midtown space. Elements of the location come together to create the ideal setup for your business, workshop, or networking event. The space is also highly configurable, able to meet most event specifications.


Located in a beautiful Brooklyn neighborhood, this former tile factory has been renovated into a more welcoming space. With modern architecture, exposed brick, and a relaxed atmosphere it’s the ideal space for your next big meeting. Step out of the old office and into one with character.


If you are looking for a more versatile location, this Midtown Penthouse is for you. Entertain guests out on the terrace, conduct business meetings in one of two spacious studios, or lounge by the cozy original fireplace.


Foster your creativity in a space that truly inspires. This enchanting private library stimulates the imagination with its extensive collection of books, records, and art. The space is great for anything from reading a book to teaching a small class.

All images borrowed from Splacer