This spring, we had the pleasure of partnering with The Street Trust, a multimodal transportation advocacy organization based in the Portland Metro area, to revamp their strategic plan for the post-pandemic world.
Sarah Iannarone, the organization’s interim executive director, had collaborated with Pregame in her role as director of First Stop Portland and as a guest speaker at our PDX Clubhouse. As part of her small business advocacy, Ciara Pressler was also on the steering committee for Sarah’s 2020 mayoral campaign, contributing her perspective on Sarah’s agenda for supporting entrepreneurs and creative professionals.
Here, Sarah and Ciara debrief on our unique approach to turning a strategic planning opportunity into an actionable game plan.
Ciara: Sarah, let’s jump right in. How are 2021 challenges unique for nonprofit?
Sarah: 2020 undid all the best-laid plans. I don’t think there was a plan that went unscathed. The murder of George Floyd, the pandemic, economic upheaval, the climate crisis… all of these created chaos… chaos is the new normal.
My organization had been in a bit of upheaval prior, so the plans we had on the books needed urgent review. We needed a roadmap to navigate uncertainty and create a steady footing for the future.
One of the best things about doing a strategic action plan update was the individual polishing of each component for a healthier whole. Even if we hadn’t changed a thing, the process of having everyone think through it again together reaffirmed our dedication to our work. It was a good time to have our people come together and recommit to our renewed vision, mission, and values.
What is it like to enter an organization as an interim executive director? How does your approach differ from an open-ended employment engagement?
Liberating. The short-term contract meant that I didn’t need to center myself in the process. I was able to stay focused on what would be best for the organization, not for me as its leader, and what would ensure long term impact and sustainability.
After this experience, I would even recommend for new executive directors to start as an interim and go through this process with your board, staff and stakeholders as a chance to assess who you’ll be working with. Do your vision and ideas align with your community’s? Going through this process together was enlightening and unifying.
We’d collaborated before, and we’re friends, but this was the first time you hired me and Pregame for a project. What made you come to us?
I’ve watched you for a while and I appreciate your style and approach. I thought they would be of value to our organization. In particular:
I appreciate your clarity of vision and certainty of voice. When approaching things from 30,000 feet, you can’t equivocate. I appreciate how you decisively assess the landscape, ask the right questions, and don’t get mired down in a lot of deliberation. Especially in a city like Portland, where we have meetings to deliberate the schedule of a meeting about a meeting, your ability to wade out of that quickly with assertiveness and grace is an asset, especially given the urgency of my organization’s need for clarity and action.
As much as I knew and trusted you personally, knowing you’d just finished the strategic plan for PF&R legitimized my choice to bring in outside with my Board. Here was someone with demonstrable results from a major institution in our city. I respect Chief Boone and that plan turned out well. I knew you’d do a great job with The Street Trust.
In my sector in particular, you encounter a lot of strong voices from the dominant culture who are accustomed to shaping outcomes. I wanted someone who could hold their position in the face of that with assertiveness and certainty. You are adept at demonstrating the executive leadership traits that challenge the dominant culture, without falling prey to this “I have to be the antithesis of the dominant culture to be successful.”
Your presence in this place of strength and certainty allowed me to just be myself as a leader – it’s as though you ran sweep for me with stakeholders so that I could have the greatest efficacy at the helm of the organization. As a female leader, you’re often having to tamp down certain personality traits to be perceived as “leaderly.” You gave me space to be my own kind of leader — you empowered me, and made me look really good!
You have good boundary setting; you set clear goals and guidelines. I remember at one point I wanted to go wide on the process, but you guided me to a different timeline, which ultimately defined which stakeholders to engage at which part of the process and in what ways.
How was our strategic planning process different from other high-level planning you’ve done in the past, particularly with outside consultants?
Most significant difference was right at the beginning: cutting through unnecessary deliberation to get to the heart of the matter. We were more practical than theoretical.
You moved us through quickly with very good results, so we didn’t get overly complex and our action items were concrete. It helped us connect our plan to real world things like staffing and the budget. I’ve used our plan to build out job descriptions for the roles that became apparent through your game plan process. The plan is very good at keeping me on track day to day as an administrator and manager.
What was your Board’s experience with our strategic plan approach? Be honest!
They’re all happy with our plan- they passed it unanimously just four months after I joined the organization.
We had positive feedback after each of the work sessions you facilitated. At first, there were one or two people who didn’t understand the value of bringing in an outsider or the cost of paying a consultant, but you were worth your weight in gold because of efficiency and clarity in moving us through the process. Ultimately, we arrived at something better than if we’d been left to our own devices; there was a grounding factor of not allowing us to sit there and wallow in our own sector and our standard discourse.
What advice would you give to someone who is intimidated by beginning their own strategic planning process?
When chaos is the new normal – politics, economic, climate, migration, pandemics – instability is going to be surrounding us indefinitely, and that can be pretty suffocating. It can make it hard to know what to commit to, what investments to make.
This strategic plan has given us such an important tool. Think of it like a very good recipe book; it’s the tool to guide you through the work. You want your tools to be good. You want recipes that are tested and knives that are sharp. Powerful tools increase your impact in the world. When you think of your strategic plan like that, it becomes a buffer against uncertainty.
Now I know that if I need to pivot in my organization, I can come back to our values and what we outlined in this plan to keep us on track.
Anything else you’d like to add?
I’m thinking of you as a doula – the person who gets you from one side of a really painful process to the other (laughs).
Sarah! We already have enough trouble as women in leadership. Give me another metaphor.
Ha! Okay, we can use the word Coach. Someone who can turbo boost your thinking and your decision making. They get you from point A to point B much faster and with better outcomes than you would by yourself.
Learn more about The Street Trust at www.thestreettrust.org