Strategic questions for strategic thinking for nonprofit leaders with Carol Hamilton
12/16/2025
“Strategy is deeply human work. It’s about how we take care of ourselves and each other. It’s about the conversations we’re willing to have—and the ones we avoid. It’s about pausing long enough to identify and test our assumptions, seek new perspectives, and ask the deeper why beneath the first answer.”
Strategy for nonprofits is not a plan to perfect but a human practice—built through care, curiosity, and intentional choices in the face of uncertainty.
As the year draws to a close, episode 138 of Nonprofit Mission: Impact brings together reflections from a wide range of nonprofit leaders and thinkers, all responding to one central question: What should nonprofit leaders ask themselves to be more strategic?
Across topics as varied as crisis management, equity, careers, evaluation, organizational design, culture, and innovation, a clear throughline emerges—strategy is deeply human work. Rather than offering abstract frameworks, the episode highlights:
practical, grounding questions and practices that help leaders navigate uncertainty with clarity, intention, and care.
An invitation to slow down, resist urgency, tend to themselves and their teams,
Why it's important to surface assumptions, seek multiple perspectives, and make decisions rooted in both alignment and capacity.
Together, these reflections offer a steadying guide for leaders facing complexity in the year ahead.
Highlights
Setting the Frame: Strategy Through Reflection and Humanity
[00:00:00–00:01:13]
Strategy is not just a technical exercise. We review a set of reflective practices that help nonprofit leaders navigate uncertainty with humanity. The focus is on questions that anchor day-to-day decision-making as well as long-term direction .
Caring for Basic Needs to Make Better Decisions
[00:04:10–00:08:01]
A core reminder emerges: leaders make more grounded decisions when they attend to basic human needs—food, rest, space, and care. Small, practical actions build capacity in moments of chaos and help leaders remain steady under pressure .
Don’t Go It Alone: Expanding Perspective Through Support
[00:08:01–00:10:31]
The conversation emphasizes that leadership is not meant to be solitary. Whether through accountability partners, peers, coalitions, or outside facilitators, seeking support is framed as a strength that broadens perspective and improves decision-making .
Two Essential Leadership Questions: “What Am I Missing?” and “Tell Me More”
[00:10:31–00:12:03]
Leaders are encouraged to assume they do not see the full picture. Asking these two simple questions helps slow conversations down, surface new information, and invite perspectives that might otherwise remain hidden .
Surfacing Expectations and Assumptions
[00:12:03–00:14:27]
Another strategic practice highlighted is examining expectations—another form of assumption. Leaders are invited to ask whether their expectations are realistic and to consciously test the beliefs shaping their decisions rather than taking them as givens .
Asking “So What?” to Get to Strategic Impact
[00:14:27–00:16:45]
The discipline of evaluation is framed as an act of curiosity. Repeatedly asking “So what?” helps leaders clarify why information matters, what change they seek, and how learning should inform decisions and communication .
From Individual Practice to Organizational Insight
[00:17:00–00:18:03]
The episode transitions from individual leadership habits to organizational strategy, emphasizing that personal practices scale into collective impact when embedded in how organizations operate .
Interrogating Organizational Design
[00:18:03–00:19:00]
Leaders are encouraged to ask foundational questions about what their organization actually is. If results aren’t matching intentions, the design of the organization itself may need to be examined and realigned with strategy .
Culture as the Silent Driver of Strategy
[00:19:00–00:20:33]
Organizational culture is named as a decisive force. Leaders are urged to look honestly at “what is,” not just what they wish culture to be, recognizing that unspoken norms and assumptions shape behavior more powerfully than stated values .
Filtering New Opportunities Through Alignment and Capacity
[00:20:39–00:21:59]
Strategic discipline requires saying no. Leaders are encouraged to evaluate new initiatives by asking whether they align with strategy and whether the organization has the capacity to take them on without harming morale, operations, or impact .
Resisting Frantic Urgency in Favor of Sustainable Focus
[00:22:05–00:24:00]
A distinction is drawn between urgency and frantic urgency. Leaders are invited to slow down, focus, and make thoughtful choices that support organizational longevity rather than reacting to every immediate pressure .
Closing Reflection: Strategy as Moment-by-Moment Human Practice
[00:24:08–00:25:53]
The episode concludes by reaffirming that strategy is built through curiosity, presence, and care—moment by moment. Leaders are encouraged to choose sustainability over urgency and to approach the year ahead with clarity, connection, and intention .
Important Links and Resources:
Independent Sector coalition data base
Related Episodes:
Episode 126: Navigating Nonprofit Careers
Episode 127: From Guilt to Responsibility
Episode 128: Building psychological safety in nonprofit organizations
Episode 131: When the stakes are high
Episode 132: Demystifying government grants
Episode 134: Rethinking nonprofit program evaluation
Episode 135: Designing nonprofits for impact
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Carol Hamilton: A while back I started ending my conversations with the question, what is one thing that you would want nonprofit leaders to ask themselves to be more strategic about whatever topic we were focused on? And as we round out 2025, I'm pulling together my guest's answers to that question. The topics that we tackled were wide ranging from what white leaders can do to become more anti-racist to government grants from nonprofit careers, to building psychological safety within organizations, to managing crises with your humanity intact.
Carol: From organization design to creating program evaluation from innovation to what it means to be an interim director. And yet each guest answers. Pointed to a deeper set of practices that help leaders navigate uncertainty with clarity and humanity. The responses were rich, touching on how we can care for ourselves, how we make decisions, how we test the assumptions, and how we can stay connected to mission and community.
Carol: My hope is that these snippets give you a chance to step back, pause, and reflect as you close out your year and head into the new one. And if you're listening to this leader, there's no reason to not use these at any time to enhance your strategy, as well as some great advice to anchor your day-to-day decision making.
Carol: Nonprofit Mission Impact is the podcast for nonprofit leaders who want to build a better world without becoming a martyr to the cause. I'm Carol Hamilton, your podcast host and nonprofit equity centered strategic Planning and evaluation design consultant.
[AD BREAK]
Carol: Are you leading a nonprofit right now and feeling like every week brings a new wave you just didn't expect? You're not alone. So many leaders tell me they're tired of being in constant reaction mode, just trying to get through the next board meeting, the next deadline, the next crisis. If that's you, I wanna share something that can help.
I've created a scenario planning service designed specifically for nonprofit teams, navigating uncertainty scenario planning helps you imagine multiple possible futures, not to predict the perfect one. To prepare with confidence for all of them. Together we explore what's within your control, where to focus your energy, and what decisions will help you stay true to your mission.
Even when the world feels unpredictable, you walk away with clarity, alignment, and a grounded plan you can actually use if you're ready to stop reacting and start steering your organization with intention. Learn more about my scenario planning packages@gracesocialsector.com, all one word, grace social sector [dot] com [slash] scenario [dash] planning.
Let's help you steady the ship so you can keep moving your mission forward. At Grace Social Sector Consulting, we help mission-driven organizations like yours create clarity, alignment, and momentum so that you can focus. Your energy on what truly matters. Learn more at gracesocialsector.com slash scenario planning. That's gracesocialsector.com/scenario-planning.
[END AD BREAK]
Carol: I always spend time at the end of the year reflecting on what's gone well and what could have gone better. And by looking back, I am better positioned to envision what I want to be true in the upcoming year. It's a mini version of what I do with organizations as they set their direction for the future in strategic planning and scenario planning.
Carol: Most of these questions and tips for my guests will serve you in moment to moment decisions that you have to make every day. You may find that one or two of them jump out at you and you want to add them to a checklist or a post-it note as reminders for whenever you're faced with any big decisions. We first hear from Melissa Kessler from episode 131.
Carol: Melissa and I talked a lot about how to retain your humanity as you deal with crises, especially hard choices involving people and how to communicate these. Melissa's advice for managing a crisis is very down to earth. Let's listen.
Melissa Kessler: I was in a job that was very chaotic for a long time. I had someone working in my team and she said something to me.
Melissa: We were talking about things like schedule and busyness and whatever, and she said, I see you take care of yourself. And I was like, uhoh, you know, like, what does that mean? And it really stuck with me because I thought about it and I was like, she's like, no, no, no, I see what you do. And I thought, that is so interesting because when I thought about it, I was like, what she meant was when I needed, you know, lunch, I went and got lunch.
Melissa: I may not have gotten lunch the minute I needed it, but there was a snack in my drawer, you know, when I needed, like really, I needed to go home and work on something. Like I would do it when I needed, you know, just peace and quiet, I'd shut my door. And that was not always popular. But I think understanding, like, I mean, going way down to basic human-level needs. Having some sense of what really matters to you as a leader feels really important because in the melee, in the chaos, I think people do get lost, and you can end up not taking care of your own, like physical self, but also not taking care of relationships and your mental health and other things that once that stuff starts to fall away, you have bigger problems.
Melissa: Like you, you cannot possibly manage a chaotic environment. Under those circumstances. So for years and years I did like crisis management. Crisis communications, and in my list of instructions, which I would say maybe this is like tangible tip number two or whatever, but like if you don't have already like a basic written crisis plan like you should just on a piece of paper, because we know that humans in moments of surprise, especially like we don't know how we'll react, it's not exactly predictable, but you will not be thinking clearly.
Melissa: For years and years, I kept a post-it on the inside of one of my cabinet fronts that said, do these things in this order. And so it's like if something wild happened, I could pull out my post-it and like literally just go through my list. And that was enough to get me to a stable state. But one of those things was always ordering food.
Melissa: If you have to put, well, you, if you have to put a group in a room to figure out something acutely. You don't have that much time until people start getting hungry and peckish and hangry and all of those words we have. And if you, you know, it's like taking care of that human need that can be done in five minutes on your phone or asking someone to go out and do it or whatever.
Melissa: And then cross that off the list you, you've built capacity. I think that's probably the headline for this moment is anywhere you can build some capacity, you should do it because you're gonna need it.
Carol: So that's your first to do is we continue to serve the crazy times we're in Rule number one from Melissa, feed people and yourself when you are faced with really hard decisions.
Carol: It's become such a cliche to quote, put your oxygen mask on first. Yet, how often do we actually do it? We make better and more grounded decisions when we take a minute to take care of our basic needs. Taking a deep breath, eating something, drinking a glass of water, moving our body, getting enough sleep.
Carol: All of these simple practices definitely help me be better resourced to manage what gets thrown my way. Another good reminder that I've heard from guests again and again over the years is the invitation to not go it alone. Cat Lazaroff from episode 127 stresses a. She's talking about individuals learning new things where accountability buddies are so helpful.
Carol: And the same can be said for organizations. Don't go it alone. Chances are what you're working on. A lot of other people are too. Get to know them and connect. In fact, the independent sector recently created a searchable database for coalitions and networks so that you can find one that connects to the work that you do.
Carol: I'll put a link in the show notes so that you can find it, and on the individual level, leadership can be lonely. Getting help and support you need is a sign of strength rather than weakness. Let's hear what Cat has to say.
Cat Lazaroff: Nobody should do this work alone. You need help. You need help. And it doesn't have to be a consultant like me.
Cat: It can come in other forms, but if you do the work alone, then the only perspective you're seeing is your own. And that is not the only perspective that is valid. And I would also say. You need to create a, a brave culture where folks feel safe enough to say the hard truths and the benefit of working with a consultant with somebody from outside is that they can, they can create that safer, braver space for anonymity if needed, for people to say what needs to be said so that everybody can hear it.
Cat: And, and also not have the person who is going to be transmitting those tough things back to the organization. Be somebody you have to go sit next to in your next meeting. So there's lots of reasons for working with somebody. I don't do this work alone. I do this work with wonderful accountability partners in a lot of different spaces, and I always will, and so should you.
Carol: Michael Randel from episode 128 also spotlighted the value of multiple perspectives. He reminds us to not forget that all of us have things that are less obvious to us that we might not consider from our point of view. He poses two questions that are useful in a wide range of situations. First, what am I missing?
Carol: And the second, tell me more, to go deeper when you're talking with somebody, let's dive into his insight.
Michael Randel: I think there's, there's two questions that I would love to see leaders using more. The first one relates to how they communicate, and so the question would be asking, what am I missing? So it starts on the assumption that I'm not seeing everything.
Michael: I dunno, everything. Others have got useful things to bring. So let me invite you. The second question is about how you're listening and it's about me more. So be curious. Don't just accept the first thing that gets said, but try and understand more about it. Right? And I think those things together, deliberately inviting.
Michael: More information, more perspectives, and then being curious about what gets offered really will help you slow down, and sort of broaden your perspective on what's going on and what you might do about it. So those are the two practices I would encourage leaders to pay attention to and try it out and see what happens in your next meetings as you, as you try those two questions.
Carol: When I talk to Matt Hugg about nonprofit careers in episode 126, his advice and questions for folks also reinforce what Michael recommended Matt's question. Am I being realistic about my expectations? Requires you to think through what your expectations are. Let's hear it directly from Matt.
Matt Hugg: Am I going in with my eyes open?
Matt: Am I being realistic about my expectations here? You know, it, it, it, it's going to be hard if they like, like we talked about, come in and feel everybody's gonna be nice and fuzzy and softer and that there won't be expectations that they'll be the first person out there instead of being the second person behind the first person.
Matt: And that, but also keeping that mission. It's all about the mission and, and that's the other thing too, that I'd say is that the more contact, even if you're an accountant or a gift processor or a researcher or whatever, the more contact you can get with the end user, the people you benefit from, that's gonna sustain you.
Carol: Expectations are another way of saying assumptions, and both can trip up if you let them stay hidden in our conversation about innovation, organization, cultures, and nonprofits and associations. In episode 136, Elizabeth Engel makes a similar suggestion. She encourages leaders to make sure they identify the assumptions they're working with and then think about how they might be tested.
Carol: Rather than taking them as givens. Here's how Elizabeth puts it.
Elizabeth Engel: For me. I guess this goes back to the thing that sparked the original white paper in 2015 in the first place, which was working on a previous white paper around evidence-based decision making. The big question that I, I would like association execs to ask themselves more often and truly, I mean like startup methodology is, is a type of evidence decision making is.
Elizabeth: Like, what are, what are my assumptions? How am I going to test them? And so really what that comes down to, to put it in an even simpler way, is how do you know? Just ask yourself, how do I know? How do I know this? I think this is the case. How do I know that?
Carol: Kayla Meyer's question is a great follow up. She says asking.
Carol: So what frequently is important now is not to try and sound like a fed up teenager, but to push us outside of our own viewpoint and get us to consider an angle that we might be missing. Link to Elizabeth's point about evidence-based decision making. My conversation with Kayla in episode 134 about program evaluation.
Carol: A discipline that is about gathering evidence for whether what we're doing is having the impact that we're hoping for. So let's hear what Kayla had to say.
Kayla Meyers: And it's really the, so what? It's truly it. I feel like most of my job is me saying, so what? And, and so you can, you can cut me out and just ask that yourself, but, but to really explore why they wanna know something or why something's being asked of you so that you can really mm-hmm.
Kayla: Onto it. Right? So being brave and bold in those conversations where someone says, I would love to give X amount of dollars that you can expand services to. A thousand people kind of saying why, you know, what, what are, what are you kind of being able to put, put those pieces together, and not necessarily in a defensive way, but just saying, what are, what are you excited about?
Kayla: What change do you believe that we can make? And, and why a thousand? What are you looking for? What do those thousand people represent to you? And being able to bring that back into your learning strategy. So what do we want to know? For what reason? What's going to help guide our decision making or guide the way we communicate about our work.
Kayla: We're not just handing out meals after school, so families have fresh food when they get home. We're creating shared meals in, in a family structure, and we know that shared meals are linked to increased mental health outcomes, increased academic resources, like being able to really get to that. So what of your work?
Kayla: In those conversations with funders and your conversations with your staff and your conversations with the community and being able to then say, okay, how are we gonna measure that? How are we gonna really try and, and pull that threat apart so that we can fully understand where we are being really strategically impactful?
Carol: So to recap, don't make any big decisions on an empty stomach, and make sure you feed your team too. When you're faced with sorting through a C challenging situation and make it a group affair, whether you're pairing up with an accountability buddy, hiring a coach or consultant as a guide, or looking for your allies in the wider ecosystem you work within, don't go it alone, including when you're making decisions.
Carol: As Michael said, remember to ask, what am I missing? Matt encourages you to consider your expectations. And both of these are another way of getting at Elizabeth's tip to uncover the assumptions you're working with and to figure out how to test those. Kayla's question. So what also pushes you to consider more than your go-to or business as usual answers
Carol: the questions and tips that Kat, Melissa, Matt, Michael, Elizabeth, and Kayla provide are all ones that you can enact individually and and incorporate to your own practice. Now they definitely have wider impacts. Yet the following questions and advice are squarely aimed at the organization as a whole. The first two are about getting at the root of what you do.
Carol: What is your organization and what is your organizational culture? Actually, my conversation with Julian Chender and episode 135, we focus on a topic that doesn't necessarily get a lot of attention in the nonprofit sector, organization design. And his question goes to the heart of our conversation.
Julian Chender: I think the really fundamental question is, what's my organization?
Julian: Hmm. I think it's taken for granted that the way they're designed is the way it's always been and the way it always should be. And I think critically interrogating the design is the first step to understanding if it's matching to the strategy. So yeah.
Carol (in clip): I love the thing you said before is like, what is the essence of what we're doing?
Julian: Right. Because if you're not getting the results you wanna get, I tell you, your organization is always designed to get the results it's getting.
Carol (in clip): Mm-hmm. So if your results are off,
Julian: mm-hmm. Look at the design.
Carol: Now another reason your results might not be matching your strategy is your organizational culture.
Carol: In my episode with Elizabeth Engel and Jamie Notter, we talked about the intersection between innovation and organizational culture and the fact that despite all of the slogans changes and how you do things will not stick unless they're supported by your culture. Culture will win every time. Here's the clip from Jamie.
Jamie Notter: All leaders should be asking themselves, what is my culture? Actually? What is it? Well, not what I think, not what I want it to be. Not the ideal, not the core values. Like you can have those things, those are fine, but if you don't know what is. Then you're gonna get tripped up. And again, the secondary questions are like, and when you look at what is, be aware that there's gonna be these contradictions.
Jamie: There's gonna be these, these things where it's not like you thought it was and like just accept that. Like that is, that is and is what it is kind of thing. And, but, but most people, when they start thinking about culture, like we need a culture of innovation. Let's do that. Let's put some posters up and let's talk about innovation, and let's measure our innovation.
Jamie: Let's do innovation. And they're like, go, go, go. And it's well intended. But if you, if you don't have the, yeah, but no one's gonna admit they're wrong. No one's gonna run an experiment that doesn't succeed.
Carol: It goes back to those hidden assumptions, the hidden assumptions of how we do things around here.
Carol: What behavior is acceptable and what is not, regardless of the rhetoric. As we round out, I appreciated both Justine Krank and Elizabeth Stratford Owens' point of thinking really critically about new things that we take on from a variety of angles. Justine, in episode 132 encourages leaders to think in more depth about their capacity to have a set of decision making criteria for vetting new initiatives.
Carol: Here's how Justine framed it,
Justine Krank: alignment plus capacity, asking themselves about. Both alignment plus capacity. Um, some leaders maybe wanna go after a really big plan or something, you know, whether you've got a strategic plan or not, but pursuing some really big projects. But one, is it aligned with the strategic plan and what we're doing already.
Justine: And two, knowing your organization's internal capacity, um, and where folks are at and. And really kind of having a pulse on your program staff, data finance, whatever your departments may be. But yeah, just really stopping to ask themselves about those two things, alignment and capacity.
Carol: Erin, in episode 137, emphasizes a similar sentiment from a bit of a different angle.
Carol: She invites leaders to slow down and resist the trap of constant urgency. To give yourself the permission to focus. Let's drop into that conversation.
Erin Stratford Owens: Everybody's so sick of the word sustainability, and I'm, I'm tired of hearing it, tired of saying it, but we know what that means. I would love to see less of a focus on urgency and more of a focus on sustainability.
Erin: That's really hard to say when in the current climate, when we feel like the world's burning down and oh my gosh, we gotta get this stuff done yesterday. But it will get done and we need to do it the right way and we can be strategic and without being frantic. So shiny object syndrome where you go, okay, there's money here, we can start this program, so let's go after the dollars.
Erin: It really, you gotta filter it through your strategy, through your strategic plan, but also just can we handle this? It's a part of our strategic plan, but can't, how is it gonna affect our operations, our morale, our culture, how we serve people that we're currently serving, serving right now? How, how is it gonna affect that?
Erin: So I would say, I wanna give folks permission to focus. On the work of the future, the work that you're doing now, and the work that you will do in the future versus this frantic urgency. I wanna be clear about frantic urgency because you can be urgent and understand that the problems that we are facing need to be dealt with immediately, but being smart about how we deal with them can help us to, and can speak to the longevity of the organization years to come.
Carol: Pulling together, this episode has reminded me how strategy is actually deeply human work. It's really about how we take care of each other and ourselves. It's about the conversations we're willing to have as well as the ones we avoid. It's about pausing long enough to identify and test our assumptions.
Carol: And seek new perspectives, ask deeper questions beneath the first answer. It's also about realizing that we can never actually know whether we're choosing the right path. We just have to choose, my guess, this year, to offer wisdom that meets us in the real world. Messy, fast moving, uncertain, but gives us tools to navigate it with a little more steadiness and intention.
Carol: Strategy is built moment by moment through curiosity, humanity, and presence. It doesn't actually need to be super complex. Feed yourself and your people. Don't go it alone. Slow down long enough to ask, what am I missing? What assumptions am I making? And so what? And when something new comes your way, remember to check for both alignment with your current strategic plan as well as your organization's capacity before jumping in.
Carol: My hope for all of us as we enter the new year is to give ourselves the permission to focus, to give ourselves the permission to question, to connect, to choose sustainability over urgency. I hope these insights support you as you lead your organization towards greater alignment, clarity, and impact.
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