90 Minutes of Problem Solving: Boston Area

For a limited time, Deep Why is offering free 90 minute sessions with Boston-area nonprofits. This is your opportunity to explore how we work and make real progress on a stubborn operational problem. These are applied, working sessions that are be best in person so we can access a whiteboard or flip chart.

During our time together, a Deep Why Partner facilitates a conversation with up to 5 relevant staff (or volunteer leaders). Attendees can expect to learn about and begin to use at least one new tool to clarify operational needs and next steps.

When you sign up, you will be asked for:

  • A brief, informal overview of the operational challenge you want to tackle, including some reflection on why this challenge and why now. If you're not sure, people often value using our time to identify and prioritize opportunities for improvement.

  • Any history (again, informal) of trying to solve this challenge.

  • Your preference for meeting at 50 Milk Street, Boston or your location. Please provide your address if you prefer to meet at your location. We’re sorry but we can’t travel more than 30 minutes from downtown Boston for these appointments - if you’d like for us to plan a day near you, please let us know!

When we confirm your appointment, we will ask you for:

  • Any documentation of the current process that is to be discussed/re-designed (if available and appropriate to share)

  • A list of people expected to attend the mini-workshop (names and roles)

Each session is adapted to the organization's needs. The high-level agenda for the workshop is:

  • Introductions of attendees and the operational challenge

  • Brief orientation to some of the key concepts we'll be using throughout this exercise

  • Facilitated mapping to illustrate the stakeholders, expected processes and tools, process and tool gaps and other common sticking points

  • Reflection, insights, and suggestions for next steps based on the map and Deep Why's experience of clients with similar challenges


What kinds of problems can you help me solve?

One way to think about operational pain points is to ask yourself the question: “Planning for the upcoming year, what challenges do I have internally that I know I must tackle or I won’t be able to get my job done?”

Operational pain points often manifest as:

  • Reports that are impossible to get, always wrong, or generally untrustworthy.

  • A lot of disruption when staff leave. Examples:

    • Key activities suddenly stop because nobody knew the now-absent employee was in charge of them

    • Nobody knows how to get information out of the former employee’s spreadsheet-based tracking system

    • Other staff are given extra work to compensate for the staff member’s absence

  • Poor cross-departmental communication. Examples:

    • Fundraising can’t get information from program, or program can’t get information from finance

    • Feeling like the organization spends a lot of time “getting on the same page” whenever more than one department is involved

    • Feeling like departments aren’t moving toward the same goal or are not supportive of each others’ priorities

    • Not knowing who is in charge of which decisions or activities during a project or initiative

  • Reinventing the wheel on things you’ve done before. Examples:

    • Figuring out from scratch how to launch your 3rd site

    • Having to scramble to remember all of the things required to onboard a new staff member

    • Spending a lot of time on the basics of planning your annual event.

Can you really solve my problem in 90 minutes? What do we get out of our 90 minutes?

If it’s a stubborn problem that you’ve tried to solve before, we almost certainly can’t solve it in 90 minutes. When people come to us for help. they usually present a symptom of a more systemic or structural problem, which is why they’ve had trouble solving it in the past.

What we can do in 90 minutes is help you see your operational problem very differently than perhaps you have in the past. Our approach usually clarifies or uncovers new information that ultimately leads to a workable solution. We use techniques that help uncover disconnects in the ways people are thinking and talking together that often show up very early in a conversation and are most often the cause of persistent problems.

In short, we can jump-start your problem solving, teach you some new techniques, and start you on the road to a solution.

And if your problem happens to have a fast solution, then that’s great too! We want to get you un-stuck and moving forward.

Do I quality for this workshop?

Are you:

  • A nonprofit, educational or public sector institution, or socially-focused company

  • Within a 30 minute drive of downtown Boston

  • Who has a problem that causes your staff or volunteers a lot of headaches, lost time, or aggravation?

Then we’d love to spend some time with you!

Who should attend this workshop?

We encourage you to engage staff from multiple departments who care about, affect, or are impacted by the operational challenge you have selected. When possible, it is helpful to have staff at different levels of seniority attend in order to bring to light different experiences of the same process.

Can I do the workshop more than once?

We do have a limit on one free workshop per organization, sorry. Talk to us about pricing for a private full-day workshop or consulting services - we work hard to make our services accessible to a range of clients and needs.