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Strategy Session and Retreat Facilitation

Strategic planning sessions and firm retreats are crucial to your firm's success and competitiveness. This is when leadership convenes to bring everyone’s thinking together to develop a clear and compelling strategic plan.

Yet service firm leaders are often disappointed with the process and outcomes of these sessions. Plans are set without commitment from the team, old conversations and patterns of thinking derail progress, and the most important matters often never get addressed.

Powerful strategy sessions and retreats help set direction and goals for your firm, get key stakeholders involved and on board, and keep your firm moving forward in the right direction.

Wellesley Hills Group consultants know how to facilitate breakthrough sessions, avoid the traps that can bog down discussion, and get the most out of your strategy session or firm retreat.

As specialists in professional services firm strategy and facilitation, Wellesley Hills Group clients not only benefit from skilled meeting facilitation, but also get experts in service business growth that can add critical insight into what works and what doesn’t for growing a professional services firm.

Through our Strategy Session and Retreat Facilitation services, we will:

    • Work with you to clarify your goals for the session, including setting an agenda that is focused and goals that are achievable
    • Facilitate your session while balancing the desire to hear all voices appropriately with the need to move forward and make progress
    • Make sure all appropriate topics are brought out in the open, leaving no elephants in the room
    • Keep you from getting bogged down in unproductive lines of conversation and thinking
    • Add critical insight based on our deep experience working specifically with professional services firms
    • Prepare post-retreat summaries and action plans, along with critical advice for how you can implement the insights gained at the strategy session


At the end of your strategy session or retreat, firm leadership will have a clear understanding around the direction of the firm, what has to be done, and how to generate an actionable and clear path to get there.

Along with facilitating the process, we also deliver keynote presentations at firm retreats to energize the team and educate on important marketing and business development strategy topics.

Can Wellesley Hills Group help you plan strategy?

Give us a call at 508-626-9991, send us an email, or fill out our contact form to learn how we can help facilitate a strategy session for your service business.

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Client Quote

The Wellesley Hills Group has facilitated a number of strategy meetings for us, helped us clarify our niche and focus, and helped us penetrate our market more successfully.

Sandy Wilder

President, Communico, Ltd.