Are You Making Enough Mistakes?

0:00 You're listening to the Nonprofit Power Podcast. In today's episode, we investigate the question, are you making enough mistakes? So stay tuned. If you wanna have real and powerful influence over the money and policy decisions that impact your organization and the people you serve, then you're in the right place. I'm Kath Patrick, and I've helped dozens of progressive Nonprofit leaders take their organizations to new and higher levels of impact and success by building powerful influence with the decision makers that matter. It is possible to get a critical mass of the money and policy decision makers in your world to be as invested in your success as you are, to have them seeking you out as an equal partner and to have them.

0:52 Bringing opportunities and resources to you. This podcast will help you do just that. Welcome to the Nonprofit Power Podcast. Hey there folks. Welcome to the Nonprofit Power Podcast. I'm your host, Kath Patrick. so glad you're here for today's episode. One of my New Year's resolutions for 2026 is to make more mistakes. And I gotta tell you, it's been very interesting to see the reaction it gets when I tell people that. A few people get it and cheer me on. But a lot of folks look at me kind of funny and ask, why on earth would you wanna do that?

1:34 That got me thinking about how much energy people put into trying to avoid mistakes and what that can wind up costing us. It also got me thinking about how this applies inside Nonprofit organizations. How important it is for Nonprofit leaders to have the freedom and space and support to make smart mistakes. Action brings clarity. If we wait to take action until we have everything figured out, we're missing opportunity. And we're also very likely missing the chance to do something really brilliant. I think it's helpful to look at this from two different lenses.

2:17 There's how you look at mistakes yourself as a Nonprofit leader. And your team. Because as a leader, you're creating an environment for and with your team, and that environment matters a lot. There are kind of three main principles around why making smart mistakes can be so incredibly valuable and why it's actually better than not making mistakes. Than avoiding making mistakes. The first thing is action brings clarity. Most new directions won't open themselves up without your having taken action that reveals those new directions and those new opportunities.

2:59 I observe this happening all the time, and it's really the primary motivation for me having this New Year's resolution of make more mistakes. What I've noticed is that if you leave me to my own devices, my tendency is to wanna have stuff all figured out before I make the first move. I love to plan. Planning is awesome. I love to map out strategies and think through the details and game it out, figure out where this could go, what happens if scenario A happens, scenario B. And that can be really valuable. I use that a lot to my advantage and it works great and I use it with my clients and it works great. That said, when you're doing something new, when you're doing something innovative, when you're doing something that's taking you into the unknown at least a little bit, you can only plan so much.

3:50 You can't really know exactly how something's gonna play out. That's the context in which action brings clarity. A lot of times when you're moving towards something new that's unknown, you have an idea of how you're gonna get there. You have a pretty good idea. You've mapped out a strategy you think is gonna work. But until you take actual action and get results from that. You take an action, something happens in response to that action, then you learn from that. You say, oh. Okay, that went exactly as I thought it was going to. Yay. And it was successful. Double yay. I'll then proceed more in that direction.

4:31 But sometimes something doesn't work, and you then have to figure out why it didn't work. And based on the answer to that, what do you think will work instead? It's a bit of a trial and error process. It's smart and strategic trial and error, but it's still trial and error. And if you don't take that first action step and keep taking action, you'll never get the clarity on where you go next. Second principle is that certainty and creativity seldom go together. I'm just gonna let that sit there for a minute. A lot of Nonprofit leaders, especially now in the chaotic environment we're in with funding volatility and all sorts of other volatility.

5:18 The desire for certainty, the desire for stuff to be reasonably predictable is very powerful. But the thing is, if we want certainty, then where's the room for creativity? How does that work? So it's a balancing act. We don't want things to be completely upended all the time and no certainty at all. But if we insist on certainty in every area before we're willing to take action, there's not a lot of room for creativity in that worldview. And it's creativity that gives us the breakthroughs. That's where the really exciting breakthroughs happen.

5:58 That brings us to the third principle, which is to focus on the vision of the outcome, and be flexible about how to get there. Again, this is a balancing act. There's a balance between this and a detailed strategic plan. So let's get into that a little bit. 'Cause I can already hear the objections coming up. Like, wait, but what about this? And we just spent a million hours on our strategic plan, dah, dah, dah, dah. That's cool. I am not against strategic plans. I think they're very useful. But I also think they contain pitfalls. It is possible to over plan and in a quest for gaining certainty, we can wind up boxing out opportunity. And that we never want to do.

6:40 So first of all, let's be clear. Let's talk about what this doesn't mean. It doesn't mean that you just go try every random idea. Of course you wanna be strategic. You want to have some solid reasoning for why you think the idea you want to try out is a good one, and is likely to lead to the results that you seek. But once you've done that. You've made your solid reasoning, you have a reason to believe that a particular course of action is gonna move you toward that outcome. Once you've done that, don't try to overthink it or overplan it. Take the first couple of steps and see what that reveals. What it should reveal is clarity about what the next smartest steps are gonna be.

7:26 And here's the thing. They probably aren't gonna be what you thought. I have this happen to me all the time, and I am a super strategic thinker. I love planning. I'm good at it. I got a lot of years of strategic planning under my belt. That said, when I'm doing something new that I haven't already done before, I don't exactly know how I'm gonna get to this new and exciting thing that I want to get to, or to create this new and exciting program or product or whatever it is. I don't know exactly. I have a solid idea. I've got a solid rationale. But until I start doing, until I start taking action, I'm not gonna really know if I've first of all, considered all variables.

8:16 And secondly, typically when we're doing stuff like this, it involves other human beings who are reacting to the actions we're taking. And so we have to take a look at that and say, oh, okay, I did this thing, it did exactly as I planned. Yay. On to step two. Or I did this thing and I got a result that I'm not unhappy about, but it's not the one I thought I was gonna get. Huh? What does that mean? Okay. Does that mean that I should maybe now look down a slightly different path for my next step? Because maybe the reaction I got actually revealed something even more promising, even more filled with possibility.

9:00 You don't know until you take the action. The reality is you're gonna learn something new when you take those first few steps. And maybe throughout the process. Maybe every step will a new learning experience. Another thing it doesn't mean is that cost doesn't matter. If you wanna experiment with something that's a fairly expensive proposition, your goal is to find the MVP, the minimum viable project or prototype. You don't wanna build something out in full detail before you have a sense of whether it's gonna work and what other changes are gonna have to be made in order for it to work.

9:41 So, MVP. Figure out a way to test your idea on a small scale. Make your refinements there. Cause again, you're gonna be learning a ton of stuff and it's not gonna go the way you think. And the other thing it doesn't mean is that you don't need buy-in from others on your team. When this is your baby, this is your thing that you wanna put out there in the world and see if it'll fly. It's your job to help the rest of the team understand why this is a good idea and why it's worth testing. Be clear about what you think can be gained if it's successful, but also. What can be learned along the way that will be valuable to the organization and to the team?

10:24 Our goal is to make smart mistakes, and make quite a few of them. There's no set right amount of how many smart mistakes you need to make before you get a breakthrough. But I promise you this. If you're not making any mistakes, chances are there's no breakthrough on the other side. If you're not making smart mistakes, it probably means you're being overly cautious. And again, I get it. I get the instinct to operate from that. But we have to think about, what does that cost us? In our quest for security and certainty, what is it costing us in terms of possible breakthroughs, possible opportunities that we can't even see if we won't give ourselves permission to make some smart mistakes?

11:12 Be aware, there's definitely some things that will get in the way. Even if you say you wanna make smart mistakes, there's some things out there waiting to trip you up. And the biggest one probably is lack of safety. This is an organizational culture thing. If the organizational culture is one that doesn't tolerate mistakes or that views mistakes as failures, nobody's gonna wanna make a mistake. They're gonna feel that it is way too risky to experiment with anything. Because if they make a mistake and it's automatically labeled failure. Well, that doesn't look good. That gets a note in your file. That gets the boss barking at you, telling you you shouldn't be making mistakes.

11:56 So we have to make sure that we're creating an organizational culture that says we value innovation, we value creativity, and we value what we can learn from a smart mistake. Because there's always a lesson. When you take action and you're not exactly sure how it's gonna go, you're gonna get one of two things. You're either gonna get the result you wanted, in which case, great, you can take the next step as planned. Or you're gonna get a lesson about where you need to aim your efforts instead. And usually, most of the time it's a minor adjustment. It's a small pivot. But it's critical.

12:36 Because until you take the action, you're not gonna know that. So pay attention to language. Pay attention to how you talk about mistakes. Pay attention to how you talk about things like trial and error. And maybe think about talking about a culture of experimentation, a culture of learning, a culture of investigation and testing hypotheses. All those kinds of ways of talking about making it possible and acceptable and desirable to make smart mistakes in pursuit of a really breakthrough outcome. Another huge thing that gets in the way for almost everybody at some point, myself included, are the internal barriers that are going on inside of each of us as humans.

13:25 Beliefs about what it means to make a mistake, worrying about what others will think of you if you make a mistake. All of us acquired a big pile of beliefs about what it means to make a mistake while we were growing up. And many of us are still carrying around a lot of negative beliefs about what it means when you make a mistake. Even if you just think about the language that your parents, your teachers used when you were growing up, your coaches, whoever else. All the adults in your life who were trying to mold you into a wonderful, productive, super successful human.

14:05 A lot of times there's someone in that environment, maybe a lot of someones, who were telling you that mistakes are bad, mistakes are failure, and you should strive not to make mistakes. When we take that into our adult life and we then want to create breakthroughs and be able to foster innovation and be super creative and come up with really brilliant new ideas and follow through on them. That's really hard when there's still a voice inside of us saying, yeah, but you might make a mistake. And that's bad. That's failing. Never fail. Really bad things happen if you fail. If we've got that internal yammering going on in our head about mistakes are bad, don't make mistakes, then we will be very resistant to doing that in a work context, especially.

14:58 But it'll show up in your personal life too. There'll be all kinds of things. If you have this going on, you'll be able to think fairly easily of multiple examples where you wanted to go after something, but you were worried about failing. You were worried about making a mistake, and so you didn't take the action. We have to deal with that. We have to surface those beliefs, identify them, and then do the basic process of belief replacement work, to install in our reticular activating system a more productive set of beliefs around mistakes that are gonna support us in our quest for innovation and creativity and breakthrough.

15:41 Another thing that'll get in your way is lack of metaphorical space. If your plate is so overflowing with stuff you already have to make happen, and it's already more than you have time or bandwidth for, there is no room for new ideas or experimentation. That in itself is a mistake, and it's an unhelpful mistake. That's an organizational mistake. If you don't make room for creativity and innovation, it will cost you long term. It will cost you quality team players who may leave to go somewhere else where there is room for that. You may burn out your best players and lose them that way.

16:23 Plus, there'll be opportunities you either don't even see, or that you see and refuse to consider. It might be the most brilliant opportunity ever, but you don't pursue it because there's no room. We don't have staff for that. We don't have money for that. We don't have time for that. We don't have bandwidth for that. There's nobody who can do it. I hear all those arguments from Nonprofit leaders all the time. They see an incredible opportunity and they don't go after it. And those are the kinds of things they say as they are deciding not to go after it. The thing is, when you do that, what does that do to the organization's health long term?

17:05 It tends to lead to stagnation and cuts off the very opportunities for the additional resources that might allow you to create more time and space. The other thing that'll get in the way is waiting for perfect conditions. Oh, as soon as we have more staff, as soon as we have more money, then we can go after that thing. Then we can try that innovation. Then we can go after that new idea or that opportunity. Don't wait for somebody to give you a grant to be creative. Not gonna happen. I mean, if you're shortlisted for a MacArthur Grant, yay for you. But the odds of that are statistically pretty slim.

17:46 So don't be waiting for some external thing to happen that finally allows you to have the time and space for creativity and experimentation. Instead, make the decision that you're going to create that space. And then sit with your team and figure out how you can do that. And maybe you start out on a really small scale, but find a way to begin to create the space. Here's what I invite you to think about. How have you and your team been treating mistakes up to this point? Do you see them as valuable learning opportunities? Do you see them as a necessary part of creating new things, of pursuing opportunities, of creating breakthroughs?

18:33 Or do you see them as things to be avoided, things that cause problems. Now, the caveat is always we're talking about smart mistakes here, not dumb ones. Smart mistakes are the ones where you have thought through what you're trying to get to, and you have a reasonable rationale for how the set of action steps that you've laid out are gonna take you there. And then you allow yourself the possibility that not all those action steps may be exactly right, and that that's perfectly fine. It's an opportunity to learn. Oh, okay, how do we tweak that just a little bit to make it be the right path? But you let go of the need for certainty in that process.

19:15 So think about, have an honest conversation with yourself and with your team about how you've been treating the concept of mistakes in your organization, and how have you been viewing mistakes personally. Both of those are critical questions. If there are any lingering negative beliefs or hesitations or aversions to making mistakes, making smart mistakes, those have to be dealt with before you can create a culture that will support true innovation, true creativity, pursuing big opportunities and creating breakthroughs. Start with that. And unless you're already about 90% of the way there with this as your organizational culture, this isn't a one-time conversation, as I'm sure you realize.

20:04 If it's gonna represent a big shift, it's gonna take a number of conversations and it's also gonna take you backing up the new way with your actions. You've got to walk the talk. I have seen it happen and it's really problematic, where leadership says, okay, yeah, we get it. We get why we need to make smart mistakes. Okay, we're gonna tell everybody that's the deal. That's how we're gonna operate. And tell everybody, we're gonna have your back if you make a mistake. Don't worry about it. And then they sort of turn people loose and one of two things happens. First of all, a certain percentage of people simply won't believe you because if it's been the other way, if mistakes have been bad things up until now, telling people one time, okay, now they're a good thing.

20:51 Obviously you know that that's not how organizational culture change works. You gotta really have multiple conversations about this and back it up and talk about, well, what will that look like? What will people need, to feel like that's really true? What kind of support and guidance and coaching and whatever else will they need to feel secure and safe in taking that risk? Because it is a risk. And then we also often have to have honest conversations exploring our own personal beliefs about mistakes and what they mean, what they mean about us.

21:33 Because you can have the most supportive organizational culture in the world and someone who holds onto the belief that making a mistake says something bad about them, that it means they're a failure or they have failed. It doesn't matter what else you say. They're gonna be operating from that belief, and they will not agree to take actions that might result in mistakes. Even if they are labeled good mistakes, learning opportunities, et cetera. You have to address that piece. So I would invite you to start there. Ask yourselves those two questions and explore them and really have some interesting conversations with your team about that. And ask the question, what could be possible if we allowed ourselves to make some smart mistakes in pursuit of bigger breakthroughs?

22:22 What could that look like? What might be possible if we were to adopt that approach. And then how can we do that? How can we begin to create that here in this organization in a way where people will truly feel supported and like leadership has their back when they make those smart mistakes? And then go ahead and take action on that. Even though you don't know exactly what all the steps will be. Yet. But through action, you'll gain clarity and find the way together. Thanks for listening, and I'll see you in the next episode right here on the Nonprofit Power Podcast. Before you go, I have some news I think you're gonna want to hear.

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24:31 And as a founding member, you'll have the opportunity to direct the focus of the coaching as we go. Think about how many times you've been frustrated with a decision maker not getting it, not getting the true value of your work and its impact. This is where we fix that. So come on in. Shoot me a message on either LinkedIn or the podcast website. I'll put those links in the show notes. And let's make a plan to work together in the new year and start getting you those next level results.