EP 2 The Power of Experimentation in Leadership with Erin Winkler-McCue
Julie Harris Oliver: Welcome to Deep Work Out Loud, the thinking that fuels our life, our work, and our leadership. I'm Julie Harris Oliver. This is the podcast where I sit with another professional coach and we do some work around a single concept, a piece of inspiration, a topic maybe we've seen come up in coaching. If we're really lucky while we're talking about it, we might get a minute where we might see what coaching might look and feel like, but we'll see how this goes.
This is all an experiment. With any luck, you'll leave with something that you can apply and use in your work or your life, or both. So today I'm here with Erin Winkler-McCue. As a coach, advisor and company builder, Erin unlocks potential for leaders who refuse to settle for good enough.
She works with established and emerging leaders to expand their leadership capacity and organizational impact, and she has an exceptional ability to unlock potential. Sometimes this means crafting solutions. Other times it involves thought partnership and building awareness. Clients choose to work with Erin because she's been in their shoes and [00:01:00] has the coaching mastery to surface what's actually blocking their progress. She spent two decades building world class organizations leading operations strategy and customer facing revenue efforts at five successful startups and two public companies.
She's also an I-C-F-A-C-C certified coach with formal training from the Hudson Institute and Leadership Circle. This combination is the real differentiator. And if you're Erin's clients and you're facing your biggest leadership roles to date, this can be a game changer. Hi, Erin.
Erin Winkler-McCue: Hey, nice to be here.
Julie Harris Oliver: Before we dig in, will you tell us what led you to become a coach?
Erin Winkler-McCue: Uh, good question. So you probably hear this a lot, but it's not a traditional path. As you said, I was, I was at a number of companies. I was at small companies. I was the ninth hire. I was also at large public companies. Over time, over 20 years, I will say I saw a pattern, which was that what I liked doing most was helping people with the, the less tangible stuff.
Um, digging into the things that got in their way of having [00:02:00] greater impact. But it didn't always mean, most of the time, it didn't mean that it was functional knowledge. It wasn't a VP of finance needing to better understand. Finance, but it was him maybe reconnecting with his values in order to be able to successfully execute a reo.
And that is an actual example. But I realized that's what really gave me passion and energy. And so it's very meta, but I realized that I wanted to spend my time doing that, and I realized that I wanted to spend my time helping others find what they were passionate about and unblock their leadership so that they could take it to the next level.
Um. What I realized I'm most interested in doing is working with leaders who are in their biggest role to date, because that's really where I feel like the rubber hits the road.
Julie Harris Oliver: That's great. What topic did you bring today to talk about?
Erin Winkler-McCue: Well, I was hoping to talk about experimentation because. I have worked with a number of people who get stuck and it seems like you get these things that are such big [00:03:00] ideas that week over week they sit with them and think about them and think about them.
And so I have really seen experimentation how my clients not overnight make change, but gradually make change in a way that's very sustainable. And I thought it was something you may have had experience with as well.
Julie Harris Oliver: I'm literally doing it right now.
Erin Winkler-McCue: Exactly. We do it while we help our clients with it.
Julie Harris Oliver: Yeah. This podcast is a whole experiment. But tell me what does that, what does that look like in your coaching? Because I'm imagining a leader, like, I gotta make this giant change. I have to think through every eventuality before I even take the first step. Okay.
Erin Winkler-McCue: Yeah. Is that
Julie Harris Oliver: what we're talking about?
Erin Winkler-McCue: Yeah, I mean, can, can I give you an example that is not about coaching for a second? Because I think people might, it might work for them. One of my favorite movies is Goodwill Hunting. Mm-hmm. And so in that movie, there's one scene, I was remembering this as I was thinking about talking to you because I like to use examples sometimes that people can relate to regardless of if they've done coaching [00:04:00] or not.
So in there, beautiful scene. Robin Williams is the therapist and he's brought in to help Matt Damon, who's the student, the really brilliant student. Um. We've seen scene after scene where he's, Matt Damon's character is commenting on things like, well, I know about art and I know about books and I know about this, and in this scene I can, you can, you know, if you share this podcast, I can give you a link to use.
But it's,
Robin Williams character says, you know. There's a lot more than reading in books. And he talks about like, if I ask you about art, you'll probably say what you read, but have you seen the Mona Lisa up close? Or I may be misquoting it, but it's something like that. And if I ask you about something else, what it feels like Yeah.
To stand up. Right. And have you tried it? And that just really appealed to me. And it's weird 'cause I haven't watched this movie in years though. I do like it a lot. And so I went back and tracked it down to see if, first of all, my memory was correct. Mm-hmm. And it really touches on for me, what is one of the most critical things to making change with clients, which is this knowing and doing gap.
I think leaders have probably read a lot of books.
Julie Harris Oliver: Mm-hmm.
Erin Winkler-McCue: Read a lot of articles, seen a lot of stuff, [00:05:00] but are they doing what they've read or are they doing what leadership should look like for them?
Julie Harris Oliver: Yeah.
Erin Winkler-McCue: And so that's why experimentation is, I think, really critical. And I have done it with clients a lot and seen really, really fantastic results.
Julie Harris Oliver: Do you have an example you could share with us?
Erin Winkler-McCue: Well, we, let's go back to the example I shared a second ago, actually, because I thought it was a really impactful one, was working with his VP of finance. Mm-hmm. Um, and he had grown up in the public organization where he was working at the time when I was working with him.
And he began as an intern actually. And so he's now leading, a lot of the finance function. He's not CFO yet, but he's in line for that. And he was thinking a lot about what leadership looked like. And imagine if you've been in an organization for so many years, you've learned a lot, but you've also got some associations with being the intern who started at the company,
Julie Harris Oliver: and I imagine you've seen how leadership has done there.
Erin Winkler-McCue: Yeah. Yeah. And so for [00:06:00] him we were, we were facing, you know, the challenges for him getting ready for what was next, and we needed to figure out what he could try. And also if you're already a leader, you're, I think it's very visible, right? Mm-hmm. So you're, you feel a little bit under the microscope and you also, , don't wanna misstep if you're so close to having an even bigger role.
And you're currently, like I said earlier, in your biggest role to date. And so we really would say like, what feels comfortable? And for me it really started with defining what is a, I wanna call it a bite-sized experiment or sort of a measurable. Experiment with a start and end. So not making it a big thing, a a year long experiment is not gonna help.
But saying like, what can we try, what has been in your mind for a while, you know, and you keep returning to it, but you haven't done it. Can we take it apart and say, what's one step to, to take and to then see how it feels.
Julie Harris Oliver: Now when you're talking about a step, yeah. Excuse me. Are you meaning [00:07:00] like behave in a slightly different way or implement a different policy?
Like what? Mm-hmm. What kind of thing you're talking about?
Erin Winkler-McCue: Well, first of all, I don't think it's one or the other. It's figuring out what is their goal. And so for example, if they've been thinking, oh let's choose someone else. Um, you know, I had another client who was trying to figure out, um, they're a tech technical co-founder trying to figure out how to reengage with the rest of the business because they have been, you know, in this technical co-founder role for so much time for so long that in a sense they've sort of abdicated their role in the business strategy conversations.
There's enough to do on the technical side. And so it's like that's a big change to make overnight. So it actually, in that case, came down to when in meetings with the other co-founders, what can you do to try to show up in a different way? Now, you and I both went to the same coaching school, [00:08:00] so I think we, you would agree that it's, it's leading from behind, but asking the client like, would that be a meaningful stretch?
For him. And would that feel like something that, I'm gonna say it's gonna scare him a little, not too much, but like a, a measurable level of scariness? Like is it something you haven't tried? Are we looking to just confirm something you already know or are we actually bringing curiosity to the conversation and saying.
What could happen. I love experiments where you're not immediately gonna say, well, for sure I'd feel this. So it's the ones where they just pause and it's a nice awkward one minute with a client and they're like, I don't know. As long as I get it, I'm willing to try it. That's an experiment worth running.
And one of my favorite coaches said something to me early on, which was, an experiment never fails. If you run it, it. It. You know, if you run the experiment to try something and you end up not liking it, you still ran the experiment. And so if your question is you've [00:09:00] got a hypothesis and you wanna get some data on it, running it is, is really how you succeed
Julie Harris Oliver: because that is success even if the experiment fails.
Right.
When we were talking about doing this podcast, you said to me that this is the hill you're gonna die on. Yeah.
Erin Winkler-McCue: I think that change, what I've seen is, is that experiments lead to change in a way that a lot of other stuff doesn't. Like I was saying, you know, you can pick up a bunch of books.
How many of us, me included, have a bunch of books on our shelf that we haven't read. Right. And I would love to put my hand on the book. I would love to put my hand on the book and suddenly know all the information. Yeah. But even then, I'm not able to live it and sort of, um, manipulate it and try it. And so for me, this is how I have seen clients make.
The most effective, and I will say sustainable change is by taking steps because I think it teaches muscle memory and even before that, it teaches an awareness. And a lot of it is not just running the experiment, but [00:10:00] committing to, in a sense, debrief it. Mm-hmm. Even if it's with yourself, you know, I'll say like, if you and I are running one, I'll say, and I don't know if you wanna use a real example here. I could do a coaching moment, but it's like, if you're running an experiment, tell me ahead of time what you think success will look like or what will, if you get a yes from that experiment, because I don't wanna say success 'cause I think it's successful if you just run it.
But if you get a yes from that experiment, what are you gonna be looking for? And so, yeah.
Julie Harris Oliver: And then what, what's the next thing that makes possible?
Erin Winkler-McCue: I think it makes possible greater awareness. I think you start picking up in those moments about how do you feel? What did you learn about yourself?
What were, how did everyone else behave in the room? Using that example of going to meetings and, you know, in this case it was actually going to meetings and being more involved early on and framing the conversation and not just being a recipient in the conversation. And how do you feel? How do others feel?
Is there a business outcome? You know, are you getting to more of the stuff that you want to see move [00:11:00] forward? , Do you leave the meeting feeling that you were more engaged, therefore you talked more, therefore you felt like you were more part of the conversation? And then you start getting into this muscle memory over time?
Because I don't think it's, I'd love to say go run an experiment for one, you know, join a meeting for an hour, get deep meaning, but I think you have to, you know, get your reps in, try other things. I think you build experiment on experiment and over time there's a muscle memory that happens there.
And that's what I think leads to change.
Julie Harris Oliver: Is there any element of what else needs to be true in order for you to engage in the experiment?
Erin Winkler-McCue: Good question. So, um, yeah, I mean, I think you start, I like to ask that before, I'm not sure if you use a coaching plan with clients. Mm-hmm. But sometimes I do, depending on how they learn best and how they make change best.
But I often say like, yeah, what are we gonna need to try this? Is there a mindset you wanna talk about ahead of time? Like, are we going in with an open mind or are we going in with this and that? Do you want to [00:12:00] enlist others to help with that experiment? I would say if you're gonna do that, it can be helpful.
But also thinking about like, is that going to, in a sense, produce the signal you're looking for?
Speaker 2: Hmm.
Erin Winkler-McCue: Or if I enlist others and then I enlist you and then you tell me I did a great job. Like, is that gonna help me with my own self-awareness of how I did in the meeting?
Julie Harris Oliver: Well, on the other side of it, is it helpful to.
Warn anybody or get any buy-in if you are gonna show up at a meeting completely differently. Right. Is there any point in saying, I'm gonna try something here?
Erin Winkler-McCue: Right, right. Okay. So that's, you know, that's a hard one because I do like to get the read of, of the situation without fully enlisting everyone else.
Speaker 2: Mm-hmm.
Erin Winkler-McCue: Like, again, if I, if I'm gonna use this example, if I'm gonna tell you I'm going to a meeting and trying something, you might be predetermined as my friend to say, Erin, you did a great job.
Julie Harris Oliver: Right. Or set you up.
Erin Winkler-McCue: Right, right. Oh yeah. You'll challenge me in the meeting. What do you mean? Yeah. Um, or
Julie Harris Oliver: let me lobby you an easy one.
Erin Winkler-McCue: Right. So I'd, you know, ideally I'd say, you know, not if you're gonna do something [00:13:00] dramatic, then maybe you enlist a few people. I mean, there's that whole concept of pre-wiring a meeting. Mm-hmm. But I really do sort of want that early experimentation to let you get the raw read of the situation. So I would say actually, if you feel like you need to pre-wire a meeting in order to run something.
Maybe you start with a, a less high stakes experiment so that you can get the read. You know, I, I have a client who currently, for example, I would say coaching is sort of an experiment for him. And he is, , he is a founder, but he chose to pay for this outside of his company's budget because he doesn't want to let other people know he's doing this.
Julie Harris Oliver: Oh.
Erin Winkler-McCue: Because he wants to have an experiment and be able to see what the feedback is over time, as he hopefully changes in the ways he wants to change without having people just sort of preemptively saying, you're doing great. I noticed, you know, you're going to coaching. That's great.
Julie Harris Oliver: Right. How's that coaching going?
Erin Winkler-McCue: Right. Right. So it's interesting.
Julie Harris Oliver: Yeah.
Erin Winkler-McCue: How do you use experimentation in your own client work?
Julie Harris Oliver: [00:14:00] Mostly when a lot of my clients are looking for, the next rung on the ladder or looking how to get promoted or get to that next level. Mm-hmm. And so we're talking a lot about what is the, what are the gaps there and what is it gonna take to get you to that next level? 'cause there're a lot of them are at that position of that moment when you've been a really good soldier and you need to make that flip to be a leader.
Mm-hmm. So then what are those behaviors that have to change? And what is a mindset that has to change to go there? Mm-hmm. And so we're looking at experiments in that. Context of how could I try to go into this meeting differently? Right. How could I try to lead this rather than just being reactive?
Mm-hmm. I think those are the kinds of experiments we look at.
Erin Winkler-McCue: Yeah, I mean, it feels like that gets at the, what's stopped you from doing this so far?
And as I, I'm guessing, I don't wanna speak for you, but like there are those people who go to coaching for accountability.
Julie Harris Oliver: And sometimes they're in a position of, oh, I didn't know I could do that. Right, right. Oh, I didn't know that was my job. I didn't know [00:15:00] that's how I get ahead.
Erin Winkler-McCue: Right, right, right. I think that's, those are the great moments, right? When someone. Try something that they saw as this massive thing.
And they've been thinking about it for a while and so that's when I said accountability a second ago, I don't mind if it's accountability to say, you know, that's sort of like I said earlier, sort of the thing that scares you just enough. Mm-hmm. Like if, if, if we're talking about accountability, which is, I'm gonna keep nudging you.
In a very polite way, and you're paying me to nudge you, but like we're going to keep moving you forward and sort of seeing like, what's the extent of, of your ability to, like, at what pace can you learn and try new things And to your point, you know, if they're moving from, maybe it's, you know, a good soldier into a leadership role or a bigger leadership role, like there are those people who don't like that next step.
Julie Harris Oliver: Mm-hmm. Um.
Erin Winkler-McCue: I know in the world of engineering, there are people who end up discovering that. You know, when you get more senior, you always envision stereotypically, you start managing people. I've known engineers who say, you know, I wanna be a [00:16:00] principal. I don't actually like managing people. I miss my other work.
Julie Harris Oliver: Yeah. And I think there's a lot of companies fail because they put those people in management mm-hmm. Who have no interest in managing people. Right. They've been the best engineer for the last 20 years. Right.
Erin Winkler-McCue: The, exactly. Yeah. Yeah. And so I think that's an emerging recognition. I've seen it happen more in engineering than I think other departments right now.
Julie Harris Oliver: For sure.
Erin Winkler-McCue: I don't know if there's like a sales principle. I've never heard that role. Maybe they move you into like enablement, but I think that is a recognition and so how, instead maybe do you give an opportunity to experiment, you know, do they lead a project where half their job is to manage the people and end up realizing they would rather be the lead person with the technology and have the technology be what they're managing, not the people.
Julie Harris Oliver: Right? Right. I think sometimes there's also an element of permission. That they might be waiting for permission. Mm-hmm. Mm-hmm. And so the experiment might be what if you didn't wait for permission on that,
Erin Winkler-McCue: right?
Julie Harris Oliver: I You ran with it.
Erin Winkler-McCue: Yes. I love that one. There's definitely a lot of, there's a [00:17:00] lot of people out there waiting for that, and I would rather use the constructs we're talking about to help them move forward in whatever feels good to them than letting a layoff say happen.
And force them to try something or having someone else, you know, I myself was in this position where someone else raised their hands earlier in my career and became chief of staff of a company I was at guess what I wanted to do? I wanted to be chief of staff. That's what you
Speaker 2: wanted? Yeah.
Erin Winkler-McCue: Yeah. And what.
I didn't think, you know, it's that stereotypical, like, I didn't think I had everything that would check every box, by the way. There was no job description, there was no job description, but it was in my head was why I couldn't move into that.
Julie Harris Oliver: Yeah. Um,
Erin Winkler-McCue: it was a man, I mean, I'm, yeah.
Julie Harris Oliver: We could do it another hour.
I'm not gonna say it's
Erin Winkler-McCue: always a man. Yeah.
Julie Harris Oliver: But the data shows women will wait till they have 12 of the 10 boxes checked and men will wait till they have three to throw themselves in.
Erin Winkler-McCue: So I did do this a few years later, but my point was I learned from seeing a role that I really [00:18:00] wanted go to someone else and thinking.
I could have done that. I actually had more of those boxes than he had to check. I did learn, at least I learned later. It's not my ideal for clients I work with, but I did learn a few years later and I ended up I ended up proposing on a walk with another founder and CEOI worked for, I was one of the leaders of the customer success team.
And I said, can we take a walk? And I said. I'd love to become chief of staff. There is no role like that. Can we craft it? Can we do this and that? This is why I'm qualified. I totally practiced the pitch in a sense before I took this walk because I knew that he liked to have working meetings while we walked.
So I knew I couldn't have notes in front of me or anything. And so I practiced this whole, like I say this and I say this didn't totally follow the script, but it worked. But it's 'cause I learned from it, you know, the example in front of me a few years earlier.
Julie Harris Oliver: What steps did you have to take between watching that happen and doing it yourself?
Erin Winkler-McCue: So, I'm not proud of the fact that I think it took longer than I, you know, needed, needed to act. But, , I think a lot of observation, a [00:19:00] lot of understanding of what were the unmet needs what did I want to do. I did, you know, I think one thing for me in terms of an experiment, one thing for me was really getting to know the people I would then be working with to see if I liked them.
Julie Harris Oliver: Oh.
Erin Winkler-McCue: And how did I show up? Was I able to be my best self when I was in a room of people who were more senior than me? And sort of starting to test that sort of thing. I did not pitch this role to someone I didn't know. Right. I knew how we'd work together. That role in particular is very dependent on the person you're working for.
Julie Harris Oliver: Mm-hmm.
Erin Winkler-McCue: And so I guess you could say, I'm thinking about it now. I actually didn't think about this before, but it was sort of testing the water to see if I enjoyed that because I wasn't sure, I'm an introvert. I didn't know if I wanted to suddenly be in a role where one of my jobs was rallying all the leadership team on a regular basis, orchestrating, offsites helping with investor meetings, things like that.
Julie Harris Oliver: When you said just a minute ago that you were thinking about, do I wanna be working closely with all these people and being in situations [00:20:00] mm-hmm. To see how you interacted with them. Was that conscious at the time of, this is something I wanna make sure of before I go for this, or is this in retrospect you're thinking, oh, I was doing all these things that led to this other thing?
Erin Winkler-McCue: That's a good question. I think I knew it to some degree because I don't typically seek roles that are highly visible with large groups of people, and that was exactly what this was. At least this role, I'm gonna say chief of staff, you know, depends a lot on the organization. But I think to some degree I wanted to see if I liked doing it.
We didn't call it an experiment. I will tell you because of the situation, I, at the time owned more revenue than anyone at the company when I wanted to move into this role. So I was actually told, we forecasted you to close X, y, and Z revenue. And so for a quarter I needed to do two jobs.
Julie Harris Oliver: How how'd that go?
Erin Winkler-McCue: It was a lot of work, but I was, you know, to what we said earlier, I had energy for it.
Julie Harris Oliver: Yeah.
Erin Winkler-McCue: I wanted to try something. It wasn't [00:21:00] something that was being put on me. I had actually proposed this role and because I also, you know, knew what the company needed, you can't really just walk away from a revenue role in October.
You'd like to try something. Um, it was a series B startup, so I needed to really, even if I was in chief of staff, we would care about revenue. So I needed to try things. And in retrospect, maybe I could only do that 'cause I was so much younger and had so much more energy because it was crazy. But I did it sounds like a lot and I think Yeah, but it's driven, I mean, sure.
I mean, I'm guessing there's things in your life where. If it's, if you're on the outside, you're looking in and you're thinking, wow, is there anything like that for you?
Julie Harris Oliver: Oh, all of my forties when I was a single mother of three kids with a big sales job that was 24 hours a day and a podcast on the side in LA traffic.
Like, right. The thought of doing that now, I, no, no way, but,
Erin Winkler-McCue: , Someone else might say, do you need the [00:22:00] podcast? Right.
Julie Harris Oliver: The podcast was the only thing keeping me alive.
Erin Winkler-McCue: Exactly. No, that's my, no, that's my thinking. But someone else on the outside might say, what? What revenues attached to the podcast?
Let's talk about this. Zero. Let me be quite clear. Exactly.
Julie Harris Oliver: Yeah,
Erin Winkler-McCue: exactly. But it's all about right. And so learning that I think matters a lot. And that's one of the reasons back to what you said, like, why do I do coaching? And part of it is. Being able to help people figure out whether it's in the role they're in now, or where they want to take their role in, let's say five years.
Like what gives them that energy?
Julie Harris Oliver: Mm-hmm.
Erin Winkler-McCue: And I find that experimentation helps with not getting hung up on a very perfect plan that either you never implement or when you finally implement it. Turns out it may not be what you wanted. And that's unfortunate
Julie Harris Oliver: is that sometimes a tough sell with the Type A striver.
Erin Winkler-McCue: I think with coaching, they lead the client leads. So I'm not starting the hour talking to 'em about how we're scientists and let's go run an experiment. Right. Um, but as they're talking about, you know, what goals do you want, you know, do, [00:23:00] going back to the traditional, like the contracting for the larger engagement and then the contracting for the specific session.
How do you wanna test, how do you wanna learn? What would a milestone be if we're moving towards a certain goal and then breaking that apart? Okay. How do you get to that milestone? I don't want to ever be a coach who's in like a, you know, a Gantt chart or something. I don't wanna be this project manager but I think it's helpful to say like, where do we go?
Like, we are here and we're talking. But I think at the end of the day, they're probably gonna measure coaching by how they change. I had a great 60 minutes with Erin and I have another one in two weeks. I love that they, I have lovely clients. I love to talk to them, but at the end of the day, we're there for, because they have things they want to change.
Julie Harris Oliver: Mm-hmm. So you gotta try something.
Erin Winkler-McCue: Mm-hmm.
Julie Harris Oliver: And also, may I never see another Gantt chart?
Erin Winkler-McCue: I did have a client who busted out her, shared her screen and showed me a Moro board, and I do like Moro
Julie Harris Oliver: Uhhuh, but
Erin Winkler-McCue: still it was, I was like, well, you know, I think, I think, what are we talking about here?
And the truth was actually she was too in it. She was in a strategy role [00:24:00] and she said, yeah, I think I've gotten, you know, I've taken, what's a challenge for me anyways, about checking boxes and. Managing things and not going deeper. And she was doing that with me. And so in the moment we really used what was happening and I said, I noticed you've shown this thing and you've got, you're moving around your little, whatever it is, little, uh, visuals.
And I said, is this, is this what you wanna do together? What are we really talking about here? And we were talking about the fact that she had a very nice. Very secure role, and she wanted to move into a different part of her organization, which she has since done, but she was hung up on that for a while.
Julie Harris Oliver: Isn't it amazing how the coaching parallels what's going on outside of,
Erin Winkler-McCue: tell me more.
Julie Harris Oliver: I, I've had that happen as well where I was with a client listening to what they said and finding myself getting frustrated. I was like, is this and thinking is this. Is this really how you wanna show up with me right now as they're describing, showing up this way with their boss and getting a [00:25:00] very similar reaction as I was feeling in my
body.
Mm-hmm. , And it took a couple of sessions for me to really have the courage to reflect it back. Like, here's how you're showing up here. Are you also showing up that way someplace else? And it, it ended up being kind of a breakthrough because it was like, oh yeah, that's, that is what I'm doing.
Erin Winkler-McCue: Wow. I mean, that takes courage.
Julie Harris Oliver: It took me several sessions to work it up.
Erin Winkler-McCue: I know you said that, so, so my question would be do you do that more frequently now? When it feels like the situation would benefit from that?
Julie Harris Oliver: I do, I do do it faster now. 'cause I think, 'cause I just think it's true that mm-hmm. That typically happens.
Yeah. You can, you can use how that showing up.
Erin Winkler-McCue: Yeah. I've been reading a book about coaching and gestalt and a lot of it is about the using in the, what's in the moment. And awareness to what you're saying. And I think it's important, and I think it's part of our job is, you know, there's a reason I put a blocker before every coaching session and after because I need to [00:26:00] be rested and present and all of that stuff.
So you can notice what's happening in the moment. So, so to your, your comment earlier, like, I don't, it's not experiments all the time, I just think they're a very helpful tool for coaching.
Julie Harris Oliver: Yeah.
Erin Winkler-McCue: Because you also just have to be aware and see what's bubbling up.
Julie Harris Oliver: When you're working with people on their experiments, what are some of the things that might get in the way?
Erin Winkler-McCue: Sometimes I think it's helpful to have the the container of saying, I'm gonna run an experiment because it's in a sense. Giving yourself permission.
Julie Harris Oliver: Mm-hmm.
Erin Winkler-McCue: Regardless of how senior you are to try something new.
And so the art, the act of, of labeling, of framing it in that way, I think helps deal with maybe this traditional sense of possible failure. I think people get a, get really hung up the more senior they go traditionally on adhering to certain roles or, you know, the stories we tell ourself about what we do and what we don't do.
And then you get someone who's [00:27:00] spent 30 years in a career maybe not being fully connected to what they'd most want to do,
Julie Harris Oliver: and perhaps looking back with regret.
Erin Winkler-McCue: Maybe. Yeah. And it does, I'm not talking about just leaving a job. I'm talking about making sure they're connected to what they wanna do.
Julie Harris Oliver: Mm-hmm.
Erin Winkler-McCue: I mean, I think leaders are used to feeling competent and in a sense, experiments make you feel, could make you feel temporarily incompetent. They're awkward. I don't think most of us like to be awkward. They're vulnerable. I had this conversation with someone the other day, a client who said, even just asking, how can I help you?
Was making him feel vulnerable.
Julie Harris Oliver: Him asking him the question? Um, yeah. Or you asking him the question,
Erin Winkler-McCue: Him asking the question. He's very senior and he felt like he was then opening himself up. And how about if he didn't know how to deliver what was being asked of him in that moment?
Julie Harris Oliver: Oh,
Erin Winkler-McCue: and it wasn't, it was, there was an element of skill, but there was also an element of him not having a ton of time.
So Julie, am I asking you for some, am I asking you for something that will take an hour [00:28:00] of your time or am I asking you for, it'd be great if all next week we could do such and such. Yeah, and he, deep down, one of his values is supporting others even beyond work. But to the whole coaching thing about asking these questions, I didn't know that's where it would lead because like you, you had a look on your face, which was how does asking can I help make you vulnerable?
Julie Harris Oliver: But yeah, that makes total sense. Right. Because then you're wide open to, oh, I may have just asked something that's gonna cause me to have to say no or set a boundary that I didn't want to. Mm-hmm. And which reminds me, I just went to the Francis Frei workshop about trust and I mm-hmm. Just talked about this the other day, about the triangle and one of them being, um, authenticity and logic.
Erin Winkler-McCue: Mm-hmm.
Julie Harris Oliver: Mm-hmm. And if, if you really wanna deliver the thing, the things that you say you are, but you've set yourself up to not be able to do that.
Erin Winkler-McCue: Right. Right.
Julie Harris Oliver: Yeah.
Erin Winkler-McCue: So I didn't respond and jump in, you know, I don't believe in this copy paste coaching, so I didn't respond and say, let's run an experiment.
But I just said, is there something you could try? Because here you're [00:29:00] saying you want to, play this role. Is there something you could try without feeling so vulnerable that you won't do it? How do we get very close to that level but not go until you won't do it?
Julie Harris Oliver: Yeah.
Erin Winkler-McCue: How do we get you near that boundary and how do you try something?
You know, do you, for example, he says yes to things that are clear and that he knows, he knows and that things that he knows are easy to deliver. So do you just ask another question? We're not talking about these life-changing things overnight, but do you ask another question, Julie? What do you have in mind when you say, can I help you on the project?
That kind of question. Yeah.
Julie Harris Oliver: Is there, is there a way to put boundaries around a question?
Erin Winkler-McCue: Mm-hmm. Right, right. Yeah. Or is there a way to drill down? I mean, one of the visuals I talk about way too much as a coach is an onion and peeling the onion.
Julie Harris Oliver: Mm-hmm.
Erin Winkler-McCue: And so is there a way to just ask a few more questions to sort of zero in on what's really being asked?
And then you can say no if you, you know, and that's a whole nother coaching topic, which is how to say no, but, and boundaries. But, uh, you know, where, where can we take it? We can take it by [00:30:00] just narrowing it a little before you have to say yes or no.
Julie Harris Oliver: Yeah.
Erin Winkler-McCue: In that moment, I would say to him, do you feel like you have to say yes?
Regardless.
Julie Harris Oliver: Then what's that about?
Erin Winkler-McCue: Yeah, that's an even better question, right? Like, going, going deeper with him. Like, what's that about? So if he says yes, it's why? What's driving you to say yes? Maybe it's something in his past, maybe it's maybe it's this belief about doing service for everyone.
And then the question is. What does doing service for everyone look like?
Julie Harris Oliver: What happens if you say no?
Erin Winkler-McCue: Yep. That's a common question probably for a lot of our clients. 'cause there's this, there's a lot in society associated with saying no.
Julie Harris Oliver: Mm-hmm.
Erin Winkler-McCue: So you play that out. What happens if you say no or if you say not right now it does. It doesn't work for this week.
Julie Harris Oliver: And then how do you feel sitting in that?
Erin Winkler-McCue: Right, right. Yeah. And I also think there's a lot, you know, if we go back to the original premise for what we're talking about, is it just no and yes. Or is there this liminal space between the [00:31:00] two? Are we stuck with some traditional constructs?
Julie Harris Oliver: And what could you try.
Erin Winkler-McCue: Right. So what happens if you say, you know, you ask a few more questions, you find, find out what's really being asked. Where's the urgency, where's the nice to have versus the must have? And you say, I can help you with this. Unfortunately, I can't help you with this right now. Or Actually, I don't even know anything about the second ask, but I can introduce you to someone.
And so it's being a good listener, asking good questions in the moment. I think caring enough to be curious to say. Tell me more versus no
Julie Harris Oliver: being willing to have the conversation. Mm-hmm.
Erin Winkler-McCue: I think in a sense that's being, that's being sort of, um, other oriented more than even just saying yes.
Julie Harris Oliver: Mm-hmm.
Erin Winkler-McCue: Where do you wanna go from here?
Julie Harris Oliver: Oh, what an excellent coaching question. I think we got it. I think we did it. Where can people find you?
Erin Winkler-McCue: They can find me on LinkedIn. I also have a website, https://erinwinklermccue.com.
Julie Harris Oliver: Thank you so much for doing this. Yeah. Thanks for joining my [00:32:00] experiment.
Erin Winkler-McCue: Thanks for welcoming me.
Speaker: This has been deep work out loud. I'm Julie Harris Oliver. If any of this resonates with you, please subscribe and leave review at all the podcast places. If you'd like to work with me, you can find me at julieharrisoliver.com and let me leave you with this. What's an experiment that you can try this week?
Go try it. Report back. Thanks for listening. See you next time.