What I’m Changing About Strategy Planning in 2026

Last month, I wrote that we are living under an authoritarian regime — and that every plan, strategy, and tactic must be shaped with that reality in mind. 

In the weeks since, I’ve been helping plan two strategy meetings of very different sizes. The experience has pushed me to rethink not just what we plan, but how we plan — and who we center in the process.  

Below are a few reflections that may be useful to others navigating this same moment. 

Strategy & People 

Create space for people to process their thoughts, feelings and emotions. These conversations are hard. They force us to imagine painful scenarios and name real risks. This requires gentle facilitation to allow people the space to process and talk about their feelings and how they or those they love may be impacted.  

These conversations can surface emotions people may not have realized they were holding. Resist the urge to power through the conversations to “stay on time.” Better yet, plan ahead. Build additional time into agendas or scale back the number of items you plan to cover when you know that a meeting could touch on these types of subjects. Identify what work can be done asynchronously after the meeting and hold those to the end in case they need to be cut.  

At the same time, it’s important to be encouraging and motivational. They want us to be demoralized and intimidated. Don’t let them stop us.  

Start strategy conversations by grounding the work in our current context. For the next several years, we’re operating inside an ecosystem shaped by an authoritarian federal government willing to override state and local control. Both meetings I am organizing start with discussions of what the current context means for our work. The purpose is to create through lines to inform planning, but not overtake them, and surface realistic scenarios to incorporate into planning.  

Question past strategies and successes. If we had all the right policies, programs, strategies, messages and campaigns we wouldn’t be in the position we’re in. Resist the urge to point fingers at others and assume what you’ve been doing is the correct path. This moment calls for honest self scouting: 

• Where has our work fallen flat? 

• What “successes” didn’t actually move the needle? 

• What opportunities did we miss? 

• What would it take to win over the next 30 years? 

Don’t just ask yourself these questions, but also some of your allies, partners, communities and funders.  

Safety & Security 

Safety and security have become non-negotiable parts of any event planning. When I ran the Funders’ Committee for Civic Participation from 2015-2018 we hosted a large, annual convening every year. Not once did we have to consider if any of our attendees would not feel safe passing through TSA at the airport or ask what the hotels’ policies were with regards to ICE enforcement actions. In 2026, these must be front and center questions. 

I’ve already heard from people who don’t feel safe traveling or leaving their families in communities with active ICE patrols. Some organizations are considering restricting staff travel altogether. 

There are two concrete steps I have taken with one of my clients to address these concerns: 

• Built a full remote option, even for meetings originally intended to be entirely in person. 

• Worked closely with our host hotel to understand their law enforcement policies and build additional layers of privacy, safety, and deescalation support. 

We’ve communicated all of this transparently so attendees can decide what feels safe for them. 

Putting the Prompt Into Practice 

Living under authoritarian conditions means rethinking not just our tactics, but our planning culture: slowing down where it matters, being clear eyed about what has and hasn’t worked, and creating spaces where people feel both safe and challenged. 

Strategy doesn’t happen in the abstract. It happens among people — real people, under real conditions, with real risks.