Case Study:

A Strategic Executive Retreat Designed to Ignite a New Business Engine

Watershed Strategy has been at the forefront of digital media since its founding in 2022, helping campaigns and advocacy organizations break through the noise. But in the years they had been supporting their many clients and partners, founders Marina Orcutt and Helen Hare had not had the opportunity to strategically review their past challenges, identify future opportunities, and plan for growth. Watershed hired Center Mid Consulting to plan and execute an executive retreat that would create space for the founders to reflect and strategize, and provide them with an actionable plan built from the retreat’s insights.

The Quick and Dirty

The Challenge

Create dedicated space for reflection and planning:

Founders wanted accountability to ensure they devoted time to this exercise
Shifting industry trends required hard looks at positioning and offerings
Needed a formal business development plan to break into new markets

The Solution

A custom-designed, all-day executive retreat:

Detailed timeline with activities and prompts
Onsite facilitation to activate agenda and drive conversation
Insight identification to highlight “a-ha” moments
Real-time identification of themes and priorities as they emerged
Comprehensive notes and action items

The Result

A rewarding executive retreat and subsequent readout/action plan:

Founders felt the value of third-party facilitation
Readout surfaced trends cutting across topics discussed
Action plan turned big ideas into concrete to-dos tied directly to business goals

“Bringing in Center Mid Consulting to run our executive retreat kept us accountable and focused on the big picture. It's so easy to get caught up in the day-to-day work, and working with Hilary was integral in helping us strategize for the future."

Marina Orcutt

Partner - Watershed Strategy

The Deep Dive

Watershed Strategy's retreat wasn't just a day off-site. It was a structured process designed set the stage for years to come. Center Mid Consulting built a custom agenda and activities that:

Identified key trends across discussions
Prioritized workstreams for each founder
Analyzed competitors and how to reframe offerings to stand out
Pinpointed strengths, weaknesses, opportunities, and threats to the business

As a result of the project, the founders were able to articulate challenges, brainstorm actionable next steps, and prioritize solutions.

To sustain momentum following the retreat, Center Mid assembled a comprehensive readout that summarized the takeaways, themes, and action items from each activity and conversation, categorized into five key buckets.

Five Key Buckets
That Categorized Retreat Takeaways

01

Business planning

02

Client and Team Allocations and Dynamics

03

Optimizing Consultant Relationships

04

Self-Promotion and Marketing

05

Project Management Platform Optimization

The readout then distilled big ideas and concepts into tangible, actionable tasks that linked back to the company’s priorities for the year. Key action items included:

Identifying opportunities to delegate operational tasks to consultants
Scheduling a “reset” meeting with staff to set the stage for 2026
Creating deliverables to help the company stand out among competitors
Building tiered service packages to support business development
Ideating around how to better leverage existing contractors to drive strategic results
Developing a new business plan to break into new verticals
Deepening relationships with current network to grow among existing clients and partners

Watershed Strategy leveraged the readout as a working document to strategize for short- and long-term goals with an eye towards business growth.

"The way Hilary designed our executive retreat helped us verbalize and solve challenges in real time. It's easy to add something to a list and plan to deal with it later, but she pushed us to create actionable next steps, which was invaluable to our overall business planning."

Helen Hare