Episode Transcript
NATALIE: So we’re back again with the Purposeful Planning Podcast. Kathy Wiseman and I had so much fun last time as we were talking about systems, and one of the things that came up as an undertone, and I think really comes up in Kathy’s practice, and probably for all of us, is the role of mistakes in systems as advisors and how we learn from that. So, Kathy, tell me a little bit about how you think about mistakes.
KATHY: Well, hi there, and Happy New Year. I had kind of an awakening. I kept going to conferences where people got up and told their success stories. Many conferences, many successes, and I would sit in the audience and think, “Oh my goodness, I have made a lot of mistakes. Could I ever get up to this audience and talk about my mistakes? What would be the value?” I know that in my own practice and with people I work with, we often review where we could have done better, where we made a glaring mistake, where we had to go back and change something. I learn best by looking honestly at my mistakes, talking to people about them, and sharing ideas. Somehow, my brain engages about mistakes. And so, of course, I went back and looked at all the people who’ve made good mistakes by keeping trying, by identifying mistakes and going on. At the time, this was a number of years ago, Atul Gawande, a physician, talked about compiling mistakes in the healthcare profession. He was a doctor, and the valuable learning. And I thought, imagine being able to share mistakes. So that kind of led me on this goal of yearly looking honestly at where I could have done better. It really is an exercise that I can keep in my head for the next time a similar situation comes up. We are in a culture where people don’t like to talk about mistakes. You don’t put your mistakes on your CV. You talk about what you’ve accomplished. But the learning, I think, is much deeper from going over mistakes. And you think about Christopher Columbus, Thomas Edison, Sir Alex Fleming, who was considered sloppy but developed penicillin. So it’s a mindset change, and for me, it’s been very valuable to look at my mistakes honestly. In fact, I’ve always wanted to do a session at all the family business gatherings, “The Best Mistakes of the Year,” as a way to kind of shift the thinking.
NATALIE: You’re still accepting PPI Rendezvous applications. Maybe we should put that together for this year, Kathy.
KATHY: The best mistakes of the year.
NATALIE: Yeah, agreed. This idea that we’re impervious as we’re doing this isn’t true. These systems that we talked about, they’re so nuanced. They’re so unique, and I don’t think just your brain learns that way. There’s a great book called The Power of Regret by Daniel Pink that talks about how we engage well with our learning. And from some of my studies with neuropharmacology, actually, all medicine, almost always, what the drug is used for today wasn’t its intended usage. But I think when you apply that system's lens, you’re able to see that, right? If you’re too focused on what you’re looking for, you miss the rest of it. So would you mind my asking, what was your most profound mistake in 2025 that’s got you thinking about 2026?
KATHY: Profound? Well, I am really working not to make as many mistakes. I think one of the biggest mistakes I made early on was with a referral source that was very important to me and I knew would be a wonderful business referral source. He referred me to a client that he was going to fund a business, and he wanted me to fix the family. And I was young enough at the time that I thought, “Oh, I can fix this for sure.” And when I went back to him, I realized that I had not explained the system. I hadn’t explained his part in it. I had accepted this referral without any content, background information to let him know what I was thinking. I wanted to look as professional as I could. This was early on in my career, many years ago. But I think when you receive a referral from someone who matters to you, whose professional expertise you admire, one of the things that I continue to do is not explain the situation as fully, as complicated as it is, not as a way to say it can’t be done, but just to include the referring source in the broader systems picture. And I think that is my biggest mistake that I think I did this year, in taking on the client and not being as perhaps transparent about the challenges. They know the challenges on one level. Often, I think people think this work can be done very quickly, so being as thoughtful and as transparent as possible, I think that’s my desire to say, “I’m good, I can do this,” and be less humble, that it will take time, it’ll have some ups and downs, but that there is a way through this. So it has to do with that triangle between the referring client, the referring person, the client, and myself, and wanting to stay completely open and transparent to both of them. I think, “Well, I want to look really competent, so I want to make very sure that I put a rosy light,” and there’s always complications. So being more open about that, that’s a personal failing.
NATALIE: Yeah, it’s really interesting that you talk about who that referrer is, or if that client is famous, or whatever. That increases those stakes. It almost makes that genuineness, that curiosity you mentioned in the last session, dissipate really quickly with wanting to look good, wanting to look right. And so, in fact, the opposite is what we end up getting with that. So how do we start raising our awareness? Because my guess is there are some situations that make us more conducive to making these mistakes.
KATHY: Well, I’m going to ask you the same thing. I think when there is an intense referral, meaning the client’s in an intense situation, and the thinking is not as clear as it could be in the client, to just make sure that people know that it takes time to get thinking clearer and the anxiety down and the worry down. Often, the referring person wants it done yesterday. So I think one of the key things is staying in contact and just describing a process that we all go through. While we want it today, it often takes a bit longer. I think it seems so simple, but in the course of rapid transactions, we often forget to describe what it takes to get the brain thinking and not reacting. So I think that kind of comment, that kind of preparation ongoing, is one that I’ve had to do. What mistake did you make this year? It doesn’t have to be a big one.
NATALIE: Yeah, one mistake I made this year is I used a lot of assessments in my work, and this family was really excited about a very simple one that they took. I usually do a simple, easy, descriptive one, and then I do a more complex one relative to the issue. And they kept using it wrongly, which is fine, that’s part of learning the language. But I didn’t understand why they were using it wrongly. And we all use things wrong, so it’s not that they did anything wrong in particular, but the way they were using it wrong is they hadn’t actually looked at the data. They weren’t making up a story about the data that was slightly incorrect but still using it. They were literally making up a story based on their past histories, applying it to whatever the random letters involved in this assessment are, and I didn’t catch it. And so when we were coming back to actually mapping the information, it was so new to them, it was so like Greek, even though they’d had their individual debriefs, that I had to completely stop. But I told them, I said, “Look, I missed this. I thought because you kept using these random letters or numbers that you all were very involved in this, and it was a new door opening for you all, and you were learning your information. But what I hear, that I think you all did, is you’re actually applying it to your old stories, and you’ve been guessing about each other instead of actually sharing the information.” And they all sat down there, and they were like, “Yeah, I guess so.” And so we actually, we were in a series of three meetings, and it was the second meeting that I realized that this wasn’t being used in a way that was powerful. And so we just had to go back, and that’s okay. I can’t actually remember a time I’ve worked with a client that I didn't sit at a meeting there and say, “Oh, this is what I didn’t realize was happening at that moment.”
KATHY: So this continual evaluation of your thinking, when you don’t do that, that’s a mistake. But you’re always primed to think about your strategy and, “Is it working or not?” I think that is a mistake lots of people make because they’re on a track that is very defined, but you’re saying you are always making that assessment as you go along.
NATALIE: I am now. I wasn’t when I was younger. When I was younger, I’d gone to a bunch of these programs, and there was a very specific track I took everyone on. But the first mistake I realized was that one of my clients wasn’t getting the thing that the other 60% had gotten. The thing that had led to a breakthrough for everyone else was getting this client stuck, frustrated, and in fact, it was hurting their system. And I was really attached. I was in my early 20s. I got into this work really young. I was really attached that if they just did it better, it would work. And I wouldn’t say that to them. And it took me a minute to actually say, “Maybe that doesn’t work.” And so one of the analogies I use for a lot of advisors when I talk to them is I had to take blood thinners for a long time. And blood thinners, when you buy them over the counter, are called rat poison. Actually, it will not just kill you, but it will be a slow, painful death if you don’t need them. So your prescription is poison if we don’t see it. So now I’m very careful to try to always evaluate with each client if it was working, but because I’ve gotten pretty good at it, I don’t always know when I’ve missed the mark right away. Like I said, for this client, a whole weekend had gone together when I didn’t see it. So I am trying to look at it, but we all smoke our own dope, right?
KATHY: I like that. That should be the title of this one. “We all smoke our own dope.” I like that. I think another mistake, and this is going to be hard to describe, is doing for a client what they can do for themselves. That’s a tough one. This is hard for an oldest sister of sisters who wants to be helpful. That’s often what we get paid for, but it’s a redefinition of help. So I am always looking at, “Am I being too helpful? Is this something this family can figure out, get the resources for?” This is a tough one for me, and I think this would be the way you define the work you do: to generate a family’s own capacity to help themselves and think through these kind of relational problems. Can we walk alongside them, giving them some guidelines, but leaving the responsibility of helping themselves on them? That’s one that, if I’m anxious, I will do too much.
NATALIE: And forget it’s everyone’s most powerful self-soothing mechanism, to just fix it. I even wrote that down when you said that: “Am I being too helpful?” And I think that’s probably the biggest risk for most of us, of advisors in this field.
KATHY: What do you mean?
NATALIE: Think about it. When you’re in grade school, the kid who has the right answer gets the grade. If you came from a traditional consulting background, which I came from, you put the perfect solution out there. That’s the thing that people pay for. But that’s part of the reason why a lot of these consulting firms, the implementation doesn’t happen. So we get paid to be the smartest person in the room, say the thing that we know, don’t give the space, don’t give the time. And so if I’m the one who has it and it will take you time to get it, why don’t I just give it to you? That’s a lot easier than watching you struggle.
KATHY: That is one that I am always aware of. And when I scope out an agenda, I do make notes of where I think I am at risk for being too helpful and not being able to generate the capacity in the group to be able to figure it out. So that is one that I’m trying to be proactive about.
NATALIE: And tell me what the note system looks like for you?
KATHY: When I scope out the agenda and they’ve got a question about the conflicts, about the estate plan, instead of giving them examples of what others do, I ask them what they’ve seen others do. Very simple. And I give them time, and often a walk around the block, to think about stories they’ve heard about failures of transfer of assets. Instead of me telling the story, and Natalie, it is exciting to hear you think, “Well, where is a 22-year-old inheritor? Where does he know from that?” But he’s heard stories in the media or from friends. It’s as simple as using their wisdom. It might be accurate, might not, but they’re bringing it to the group rather than me giving three case histories of success, less success, and no success. That is just a trick for being less helpful, not having all these stories. But there is a time for a good story. I always try and frame it as a question, not as my insight. It goes back to what you were saying about being the smartest, having the answer. But when you turn it and flip it as a question, “What’s your experience? What have you read in literature? Have you seen a movie about a trust or an estate?” That’s digging in one’s mind for that, and it provides more energy for the outcome decision than if I share my wisdom.
NATALIE: You mentioned that you go for a walk sometimes around the block. Tell me, when did that start, and what prompted you to do that?
KATHY: This is a very personal question, but you always ask personal questions. In my move from Washington, DC, where I often took walks as my exercise, I moved to the Southwest, and I found that my nervous system, because of what was happening in my family, was dysregulated. So I decided to very consciously extend my walks up into the mountains, and that had a certain quieting effect. I’ve been using, with family meetings, asking people to take a 10-minute walk outside, to breathe, to count their steps, but just to get out of a building, have your feet on the ground, and walk. I don’t know why, but it has had a profound effect on me. And I think being alone without your phone and without electronics, I think it generates some brain cells. This is not scientific, but I often have people take walks and come back in.
NATALIE: If you move your body, you actually change the chemicals that are happening, right? So that anxiety is present-focused, and so you can pull it to nourishing your body instead of that anxiety. The reason I asked is because I don’t think you say anything accidentally. And so this idea of taking that space when you’re asking your client to do some work feels disciplined, both for you, but also for them. And it’s really interesting, right? I think sometimes advisors, not only are we afraid, especially if you come from law, there’s the “don’t ask a question you don’t know the answer to,” but it’s also watching that anxiety they’re having. That’s harder than maybe stepping out from it.
KATHY: Is there something that you use to help people think deeply about something when there’s a lot of noise and busyness in the room?
NATALIE: I tend to do games, right? We will play a game that seems really silly, that might have a governance lens, might have something else. There’s one I like called Arrowheads. You tell them there are five arrows there. They have all the materials you need, and one is just already an arrow, and the other three get more and more complicated. But what they find is they’ll later say, “You didn’t give me enough because it’s only four.” And they actually have to put the four together so that that fifth arrow is made of negative space. And so one of the things we do, besides the game, and people will pull the— they’ll do all the stuff they do anyway, like the controlling person rips pieces out of the hand, they’re not listening, they’re doing all this stuff. But what that game really helps people see is they had all the tools. They just weren’t putting them together the correct way. And if you can take that anxious, excited thing that we can laugh at, “That was silly, I had those behaviors,” we can reflect on it and talk about it more neutrally.
KATHY: Well, that’s a wonderful example of the antidote to a mistake I made early on, which was jamming these meetings with content, cortical content, one hour after another. And years ago, I realized that you couldn’t, in these emotional configurations, do that. So a game like that would be a wonderful way to regenerate the thinking, rejuvenate the thinking, I guess is the better word. But that was an early mistake, just packing meetings without the time—
NATALIE: To say more about that, Kathy, because I think that’s a really common mistake in our field.
KATHY: How do I want to say it more? When you have a meeting, or have a large meeting or a small meeting, my guess is that you think through a process that has to do with problem-solving at the end. But I think often people need a robust place to think or a quiet place to think through. And I remember early on just having like three exercises in the morning and four in the afternoon. I didn’t appreciate, in emotional fields, what it takes to think for yourself. And so I would have one exercise after another, or one content-generating experience. And I think taking time in a family meeting, if it’s a husband and wife, building in thinking time is really critical. And that’s really how the walking came about. It was a chance not just to have coffee, but to get out by yourself, not have electronics be your interaction. So I’ve been trying to think about how to use that well for a long time.
NATALIE: Yeah, I think this distinction between content and process is so important, and we tend to, in our meetings, like you said, put a lot of content in there, and then we wonder why it doesn’t stick. Because they’re not able to think about it, integrate it, or do anything with it.
KATHY: Right. Interesting.I think being able to step back and watch what you’re expecting of people and the way you structure time together is really important. And I think the early mistakes I made, I was able to say, “Well, that didn’t work exactly the way I liked it.” People were exhausted, or the comments, which are usually deeper, were kind of shallow and off-putting. So assessing what you’re doing, to me, is really important. Observing, accurately observing what you’re experiencing, I think is important. I was writing about what it means to observe well. So I’m trying to get myself operating in the best possible way and to be honest when I’m not. That’s a big one. That’s a huge one.
NATALIE: What did you write down?
KATHY: What does it mean to observe well? Attentive presence. You’re engaged in the moment, but not thinking about your response. You notice what is happening rather than what you assume or expect to happen. I mean, there’s a whole slew of them. The most skillful observers can watch themselves, their thoughts, their reactions, their postures, as clearly as they watch others. It’s kind of internal double vision, acting and watching at the same time. So I did this so I would be more honest about myself and my ability to observe, because what my observations are is what I think about for the family. So am I being straight? I have a whole list that I love.
NATALIE: Yeah. So about that, in meetings, you mentioned this thing about, “Is it getting the intended results?” And just for time’s sake, this does probably have to be our last question on this, but I do think we should definitely apply to do a session on it. What are those two or three things you’re looking for to know you got there?
KATHY: Or know you missed? Can you ask that another way?
NATALIE: What are those metrics for success in a meeting, or when you know you’ve really blown it?
KATHY: That’s a hard question. I mean, Natalie, really, if people in the meeting are leaving with a sense of curiosity and reality and opportunity, not complaining or finding fault with the other, if they’re thinking of what they can do or what the future might look like, that’s different. I know their brain is in the right mode, that there’s opportunity. If they’re still locked into “This one’s bad,” or “That’s bad,” or “We can’t do this,” it doesn’t have to be a big move toward the future, but possibility. They can see a little bit of possibility for a change in the situation. Now, in the more intense differences in family meetings, a planning meeting where they’ve got some hard choices would be that they narrowed their choices and they’re somewhat excited about them. They’re not bemoaning it. It’s me figuring out if there’s a change in the opportunity for the family. But that’s a hard question. I’m going to have to think about it when I walk in the mountains.
NATALIE: There’s probably no one answer, but what I loved about your answer wasn’t that everyone was parroting exactly what we taught them. They’re not just the minions we made, and I think that’s important. And you said things like opportunity, excitement, less judgment. And I think that’s the content versus process. It’s not that content isn’t helpful. Like you said, if we’re making a decision, we need to get to a decision, right? But it shouldn’t be an hour meeting, everyone’s in agreement, and everyone knows all the details of the gnat’s eyelash. That is probably not an effective meeting.
KATHY: Well, once again, you’ve asked me thought-provoking questions for the rest of my day.
NATALIE: Wow, it’s always a pleasure. Kathy, thank you so much for taking this time.
KATHY: Pleasure to talk to you. It gets me thinking about things that are hard to put words to.
NATALIE: I love your little list. I think it’s definitely an article, maybe a presentation, maybe both. So I’ll be in touch.
KATHY: Okay. I love your superpower. It’s asking really probing questions. Thanks for your time, dear. Happy New Year.
NATALIE: You too. Bye.
