- Diane Flynn
Diane Flynn, Will Bachman
Will Bachman 00:02
Hello and welcome to Unleashed. I’m your host will Bachman and I’m thrilled to be here today with Diane Flynn, who is a multi talented she has two books. One is the upside better outcomes when everyone plays. Another book is 50 Questions inclusive Leaders Ask. She also is the instructor for two very popular courses on Udemy growth mindset and communicating with confidence. She’s an executive coach and BCG LOM. Diane, welcome to the show.
Diane Flynn 00:39
Thank you. Well, it’s a pleasure to be here.
Will Bachman 00:42
So, Diane, maybe you could give us before I dive into my questions, give us a bit of an overview of your practice.
Diane Flynn 00:51
Sure, I will give a tiny historical perspective because I think it’s relevant to what I do today. I had a career in consulting and then worked with electronic arts for over a decade, had three children and found that I wanted to I needed to pause my career, my third child was born as a medical issues and, and it just, I had the good fortune to be able to pause my career, that pause turned into about 16 years, I did keep active during that time with nonprofit boards and whatnot. So I felt like my networks and my skills were maintained. But about a decade ago, at close to 50 years old, I had the opportunity to go back into the workplace full time. And I loved it. I always say I felt like Robert De Niro in the intern where he wakes up in the morning, and he’s so energized to get up and get out of bed and get dressed and go work with a team. And when I did that, I found that it was with a tech company here in Silicon Valley. And I found that there were so many other women at my children’s schools. That said, I want to do what you just did. But what I kept hearing is I don’t feel current with today’s technology. I don’t feel connected with a professional network. And I have no confidence. And I heard this enough that I thought, you know, I can help these women I did it. I love to learn, I love to teach and I love to coach. And so with four other friends, we started a company called reboot Excel, which I’ve been running for the last 10 years. And initially, the aim was to get women current connected and confident to return to work. We’ve had 1000s of people go through our programs, and we still have resources on our website, coaching workshops, etc, to help women. However, my personal practice has evolved quite a bit. I did that initially. And then I started working with companies worked with Visa, and found that people in the workplace need a lot of the same leadership skills that women returning to work need. And I really enjoyed the b2b work working with companies retainers and longer term contracts, that was a lot easier than trying to, you know, fill seats in our in our programs. And so that has evolved into the work I do today, which is primarily coaching executives, coaching leaders, helping them build more inclusive cultures and workplaces, and also empowering individuals to do their best work.
Will Bachman 03:36
Amazing. Talk to us a little bit about the work of helping women reboot their careers. Just tell us a bit about what was the typical client you worked with? And what are some what’s the what’s sort of that process look like for women who are doing that.
Diane Flynn 03:53
What I observed well is that these women were immensely talented. I was president of our parent association at our school, I had 80 mostly women, a couple of men work with me, and they had been successful, whatever’s in their in their prior careers. And we’re taking a career pause. And I would have hired almost any of them to you know, manage events, manage budgets, run projects, they were reliable, responsible, capable, however, and when you talked to them about trying to get back in the workplace, you would hear the biggest confidence crisis you can imagine. They would say things like, I’m just a blank and which is something I say in my communications class, get that word just out of your vocabulary. It diminishes you and what you’re capable of delivering. They wonder who would ever hire them? And I keep thinking, you know, they would be great Chief of Staff. So there’s a lot of things sales, you know, and the main thing that I would encourage them to do is to reframe their achievements and their skill sets based on what they have done, whether they got a paycheck for it or not. So if they manage the auction at school, they have amazing skills. In fact, I’ve always found it’s harder to motivate and manage volunteers than it is people that are getting a paycheck, because you don’t really have any carrots to put out there. But they have run budgets, they have met deadlines, they have managed people manage teams, they’ve motivated, they’ve been creative. They’ve, you know, they’ve done so many things. And yet, what I find is that a lot of people, if they’re not getting a paycheck for what they’ve done, they dismiss it or discount it. So a lot of it was just reframing it getting on a resume as, as a skill that they could bring to a company, or role. And many, many of these people, I’d say most of them have landed amazing careers. There’s a number of women that have been through our program who are holding significant roles at Stanford University right now, which is in my backyard here, I think, come to organizations like higher education, really value that kind of experience, that pattern recognition, and just a little, you know, wisdom and maturity that they bring to the table.
Will Bachman 06:25
Where can employers go? If they’re looking to tap into that talent market? If you’re trying to hire someone who’s, you know, rebooting their career? How do you make it clear that you’re open to hiring someone like that? And is there any great websites other than just posting something on LinkedIn? Is there ways to tap into that talent pool? Absolutely.
Diane Flynn 06:47
The company I would send them to, and I worked very closely with Carol Cohen, who founded I relaunch. They work with companies, they started with McKinsey and JP Morgan, Morgan Stanley, Goldman Sachs, they and now they have lots and lots of companies that offer a program called a return ship. So think internship for someone who is returning to their career, not necessarily returning to one of these companies, but returning to their career. Got it. So what these are just like an internship that maybe one of our kids would would have out of college. It it’s about usually three months. And it’s a think of it as a try before you buy program where both the employer and the returner, have a chance to onboard and and check each other out. They get a little extra, I’m all caught handholding, you know, mentorship, especially, I know, when I went back into the workforce, I wasn’t even familiar that my calendar could be shared with everybody. Because when I exited the workforce, that was not a capability. Now we have a I think there’s a lot of people that probably aren’t familiar with how to use that in your roles. And I use it daily, by the way, so so they might get a little extra mentorship around some of the latest, you know, workplace technologies and, and ways to navigate the culture that they’d be working in. Typically, I think it’s about 80% or higher of the women who go through these returnships are hired into full time roles. So I would check out their website, I relaunched.com. I think they’re doing some of the best work around this area. Great.
Will Bachman 08:44
I’d like to turn to just one of your side gigs that I’m fascinated with, which is you are an instructor at modern elder Academy. And this is a website that I’ve followed for a while. Tell us a little bit about what is modern elder Academy and what’s the what’s the course that you teach there?
Diane Flynn 09:03
Sure. So, Chip Conley founded modern elder Academy we overlapped in, in graduate school. And so I’ve known him for lots and lots of years and I’ve always been impressed with his work he was a hotelier by trade had a very successful boutique hotel chain for about 25 years sold it then has been advising Brian Chesky at Airbnb. And when he was at Airbnb, he tells this story, people he was 52. And he said the average age of the engineers he would work with were probably like 28 and they started calling him an elder. And at first he resisted it. He didn’t want to be the elder but then they said no chip, you are a modern elder. And he started to adopt that identity of being a modern elder and really relishing all the positives that come with that the wisdom the He again the experience the pattern recognition, the mentorship. And so he started his new, I guess, what would you call it? Kind of a resort community a high end resort community. The first one is in Cabo. That’s where I’ve been for the last five years. He’s opening one this year in Santa Fe. And he calls it the modern elder Academy. And his tagline is the first midlife wisdom school. And we are very much aligned in terms of how can you stay relevant and purposeful and motivated and energized in quote, midlife. And midlife people I was asked What’s What’s the age of midlife, it’s whatever you want to define it as it’s when you have that maybe confidence crisis or that life transition. Or that time when you know, maybe you want to find something different to do, but you’re a little bit afraid to step out of your comfort zone. And so the class that the week long course that I have always delivered is a women focused course on finding your purpose and passion. And the people who come to our week are typically 45 to 70 ish. But we’ve had older and we’ve had younger, we had the 35 year old when I was there a few months ago. And so it really is not important, what the age range is as much as what the mindset is of the person attending. And we do a lot of different coaching techniques to help people identify their strengths, what sparks joy, what drains them, what impact they want to have, who they want to work with, probably the most important thing that I start with when I coach people is their core non negotiable values. Because I have found over and over that if your values are not aligned with your work, you will never find fulfillment in your job, true fulfillment. And so that’s that’s one of the you know, first exercise we do but we do a whole bunch of different exercises. And then there’s a lot of one on one coaching throughout the week, we have meals together. It’s a very fun experience and, and what the participants I think really value is the community that’s developed through this experience. And chip has created a very strong alumni program, I have 1000s and 1000s of people, I can’t remember exactly how many. But they come back for reunions. And they the cohort I was just with is still meeting once a month to support each other and give each other assistance. Chip, by the way is launching right now. The his newest book, learning to love midlife and it’s 12 reasons why life gets better with age. There’s a little couple pages about my story in the book. So I’m grateful to chip for, for sharing the Word of how you know people can really I helped to model that, you know, I’m now 61 As of last week, and I think I’m living my very best career life I feel incredibly fortunate and and energized. And I’m just having a really fun time. And then you know the other the other thing is I’m an empty nester, I have three children, they all live in Austin. Now, I have plenty of time to really dedicate to my work, which is another reason I think companies should think about this, this demographic because we you know, I’m much more focused and engaged than I was when I had three toddlers at home, for instance. So there’s lots of reasons companies should think about this talent pool as they’re seeking the best talent out there.
Will Bachman 13:54
What are some outcomes from this week? So can you give us some examples of a participant that found her purpose and passion and decided to go off on a new career trajectory, or
Diane Flynn 14:10
there are so many somebody asked me last week to send her she wants, she’s been a corporate executive for years and she wants to become a coach. So I sent her your materials for Umbrex. And there is one that stands out there was a younger woman in her mid 30s, who has always been an instructor and a writer and an author. And she felt that this was not meeting her needs for impact. And she walked away at the end of the week deciding that she was going to start a new type of University and she had already started calling some people who could help fund it. Some people who could help her develop it. A board of advisors we were brainstorming for her So that was really exciting. But there are people, a lot of people are going through a transition, maybe a divorce, maybe they’re widowed, maybe they’re making a move geographically, or they’re really unhappy in what they’re doing. And I always say, take time to pause to reflect on what it is you can bring into the world and what impact you want to have. Because there’s no benefit to anyone in staying in a role that you just that is soul sucking, you know, unless it’s well paying and you need the finances, then you know, that’s justified. But there’s a lot of people who just aren’t happy in general. And so it’s a chance to, you know, remove your goals and motivations and think outside the box and explore some opportunities that perhaps, you know, never came up in your radar.
Will Bachman 15:58
For people that want to try this at home and work on finding their purpose and passion. Could you go in a bit more detail about some of these exercises that you walk people through? You know, let’s spend 10 minutes or so on this? Of what what would you assign someone if they’re going to do it at distance on their own? How can someone get started? Sure.
Diane Flynn 16:19
And I have this on my website, I’m happy to give people the link. It’s a two page, I call it a personal inventory. And I always encourage people to start here, what it is when when I went back to my business school reunion 12 years ago, I met with a coach, and they gave me a great book, but it was about 156 pages of exercises and thought questions, which many of which I did. But I find most people can hardly do two pages. So what I did for my own benefit is I synthesized it down to what were the key questions that really spoke to me and helped me the most. So these are two pages of questions. Every time I coach someone, I send it to them, and I say fill this out, and then let’s set up time to talk. Again, I’m happy to make it available. It’s it’s, it’s openly available on my website. And so it starts with what fills your tank. And that could be anything from you know, being part of a team, for instance, is something that I love collaborating, project management, organizing, even, you know, working from home, working from beautiful spaces, a good cup of coffee, any anything at all that fills your tank, and then what drains you, and my gosh, I have a long list of that. But you know too much to do, working with people, I don’t respect, whatever that is anything too much conflict, anything that drains you throw it in there, then we’ve got the the non negotiable values that I already mentioned. Then we have my strengths. So things I’m particularly good at areas that I would like to develop, maybe I want to be an executive coach, but I don’t have the tools or the skills yet. And so I might want to take a course and or sign up for a program, then we have what do friends think you do? Well. And that’s a really interesting one that maybe sounds like a throw away. But I probably learned more from that one than anything, the rest. Because I asked my friends I said, What do you think I do well, and what I didn’t appreciate is i They said, when we go away on our women’s weekends, you know, you’re always holding Apple tip classes for us, like helping us optimize how we use our iPhones or software or Canva, or whatever it is. And I realized that probably if he had to summarize my passion, it is learning and teaching, I love to learn. I’m a lifelong learner. And then I love to share what I’ve learned and help make other people better, more energized, more productive, you know, enjoy life more. And that is it’s as simple as what I love to do. And that is what I do for a living now and that’s what I did when I started reboot was learn what people need to know and teach them what I think they need to know. Alright, so
Will Bachman 19:28
to clarify on this one, this is not just sort of hypothesize about it like what are your strengths? What do you think your friends, but you’re saying, actually go out to your friends and say, Hey, I’m doing this exercise. And I know it sounds silly, but one of the things is ask your friends what you think you do well, so please tell me what do I What do I do? Well, I mean, it’s not it’s something like that you actually ask your friends.
Diane Flynn 19:51
Absolutely. Here’s another one. I always hated public speaking, hated, hated it like I got so nervous. I really didn’t like it. People after I was president of the parent association, and I had to do a lot of it, people would say, Wow, you’re really good at that you really are comfortable up there. I didn’t believe it in myself. But hearing it from other people started to give me confidence. I thought, you know, maybe I’m missing, maybe I have a blind spot. And that is why this exercise is so valuable. And now, honestly, well, I love public speaking. And it’s not because it’s about me, it’s because I have a message I want to deliver. And I feel like doing it publicly is one way to hit the most people with it. So, you know, I always tell people are nervous, get out of yourself and get into your message. What is it you’re trying to offer your audience and when you focus on that, it usually the nerves dissolve. But that’s why this exercise is important is sometimes we miss our own strengths. Yeah,
Will Bachman 20:56
no, I love the exercise. It’s um, I suppose it’d be, you might get less honest answers. If you ask the reverse is like, ask your friends, what do you think you need to improve on or something? But maybe
Diane Flynn 21:09
yeah, you know, sometimes what I tell people because most people shy away from conflict. And when I when I coach people in the workplace ever on getting feedback, because one of the courses, as you mentioned I’ve offers is one on a growth mindset. You really do need to embrace feedback if you want to grow. And so I always tell people, instead of saying, Is there anything I could improve on? Say, Hey, you know, well, I’d love to hear a couple things you think I do? Well, and tell me one or two things you think would make me more effective in my job? Because if I asked you specifically for one or two things, you will think of them. But if I say is there anything that is a closed ended question that can be easily answered with no, you’re doing great, which is the way most people get away with. So you will never grow. We do. feedback forms after every single workshop or new program that we deliver, because we are always trying to learn and improve as a team. And so I take that to heart. Getting feedback. Okay,
Will Bachman 22:11
so I love you. So I’ll recap so far we got what fills your tank, what drains you? What are your non negotiables? What are your strengths? What What would you like to develop in? What do your friends think you do? Well, and then I interrupted you. So what are the other options?
Diane Flynn 22:25
There’s a few more, and I may not tick them on doing them from memory. One is, what impact do you want to have? You know, most people are much happier in their job when they feel like there is some greater purpose to what they’re doing. I mean, even you know, if you’re cleaning hospital rooms, but you feel like you are helping people live healthier lives and saving lives. That is awesome. So thinking about the purpose. And then there’s a section on how much do you want to work very tactically how, you know, maybe I want to work halftime, maybe I want to work 80%? Where do you want to work for me at my age, and with three kids and now a grandchild in Austin, I want flexibility. That is a huge value for me. I love working from home, I feel highly motivated. I don’t feel you know that that is a detriment. So thinking through those logistical things. And then the other one I love, and I’m gonna spend a minute on this is having a Northstar or a mantra that guides you. And I developed mine debt 10 years ago, and it has hardly changed if at all since and I’m happy to share it if it helps anyone else. Yes,
Will Bachman 23:42
yes, absolutely. What’s your mantra? Yeah.
Diane Flynn 23:45
So it’s a synthesis of everything I learned from doing this exercise. And by the way, this is not a 10 minute exercise. This is I tell people take at least two hours and then continually, continually reflect on it. It’s going to change over time. And it’s I say, you know, you have seasons of life. And when I had no kids and then kids and then empty nester, you know everything changes each time your season changes. But anyway, my mantra right now is to engage in creative collaboration with people I respect to change lives and build community. So it has to be creative, and I just need to feel creative every day. And I do lots of things to do that collaborative. I love. I think we’re better together. And I know that I don’t have all the answers, but I love working with people who bring creative ideas to the table. So that’s collaboration. People I respect I’ve worked in my life with people I don’t respect and it really drains me. I won’t do it anymore. And then why do I do it? It is to change lives. That’s all the coaching and leadership work I do. And building community is something I’ve realized I love doing I love in our reboot community we we bring people together who you know I have similar interests and, and they really support each other in the leadership coaching work I do, we always do group coaching, and we build community through the groups there. When I get asked to do something pro bono, I run it through that filter. And I think if it if it hits all those boxes, I just did something in my faith based community at the Stanford Business School last week, because it hit all the boxes, I, I find that really meaningful. And I think if you can come up with a mantra that works for you, or whatever you want to call it a short descriptor, it can be the filter through which every opportunity, whether it’s paid or unpaid, can travel. And it’s a very easy way to help you say yes or no to opportunities. So that’s about oh, the last thing on the list on the personal inventory that is coming to mind is, what’s your next steps? What are you going to do? When are you going to do it? What are you going to do this week? You know, if it’s a big thing, like I need to get a credit to in coaching, you know, what are you going to do this week, I’m going to look at programs next week, I’m going to sign up for one, then I’m going to, you know, I just went through an excellent one, through the Center for executive coaching, and I did it, it’s all online. And I thought I’m gonna do this in six weeks, it was around the holidays. And I just went on a lot of walks, and listen to this coaching program for executives, and I probably did about an hour and a half a day at 1.5 speed. And I got through the whole program. So that that’s an example of having a very concrete goal, putting time lines on it, and then making sure that you’ve put the discipline together to make it happen.
Will Bachman 26:53
So once someone has done these different kind of inventories, or reflective exercises, or asking your friends for feedback, what are your see you’ve gather all this insight, or data? What are your advice to kind of? What’s the chemistry that helps you go from that to finding your purpose and passion or figuring out? Okay, what’s my career move? Should I move across the country? Should I start a new job? Should I go back to school? Like, how do you how do you make big seems like a big leap? Right?
Diane Flynn 27:29
Well, that is there, there are plenty of options. You could find a friend, you know, an accountability partner who could reflect on In fact, when we do this in groups, in larger groups, I pair people up and say, read them some of the highlights from your two pages. And watch use third level listening, which is watching for body language watch for excitement. I coached one woman who did this exercise and she said, Well, I guess I could go back into law. And I looked at you are not going back into law. Everything about your body language looks like you absolutely hate legal profession. Do not do that. So sometimes just having an accountability partner, watch how you respond to things can be helpful. You could hire a coach. That’s what I mean, there’s tons of coaches out there that could help you navigate this. You could go to you know, there’s workshops, our team offers workshops from time to time at the reboot Excel team does that. You could. All right, what I love is something called Iike. Guy, ik IGAI. And it is Japanese. And I’m trying to remember exactly the Do you remember the what it stands for it? Well,
Will Bachman 28:54
it’s, I’m familiar with the concept. It’s
Diane Flynn 28:58
like finding that perfect fulfilling spot in your life. And I’ll just describe it’s four circles for it’s a Venn diagram. So this is how I think about my own career. And I found this to be incredibly insightful. One is your gifts or talents, one circle. The second circle is your passions. And we’ve already done this on the personal inventory. So you should have these by now if you’ve done the exercise. The third is what the world needs. And the fourth is, and this assumes that you want to make money doing it but what the world will pay for. If you’re at a point in life where money is not the important then you just take that circle off. But the idea is that if you get to the middle of this Venn diagram, you are doing things you’re passionate about you’re gifted at the world needs and the world will pay for. Then you have probably found you know that ultimate satisfaction. I love this. I found that in the early years of doing the reboot program, I was working full time at the same time in a different capacity. But we’re offering this program and we had to, you know, sell butts and seats, and it was a lot of work. And what I found is it was hitting three of the four boxes, I was passionate about it, the world needed it, I thought I was, you know, decent at it. But it was really hard to get paid to do it, you know, and at one point, we were in seven different cities, because so many people loved this mission of helping, you know, women reboot careers. And so I had seven cities of people running this program. At the end of the day, though, it was a lot of work for everyone, and no one was really making a living doing it. So that was partly why I decided working with companies is a much better business model in terms of meeting that fourth box, which is a fourth circle, which is the what will people pay for? Because companies have a lot more money to put into programs like this, then you know, and we have companies that are in their seventh iteration of the leadership program that I offer. So you know, when you get the the flywheel going, it’s a much easier way to make a living than, you know, selling it to new people every every time you offer the program. So anyway, that eek guy diagram, I found find very helpful if you just want to take the inputs that you’ve developed through the personal inventory, exercise, and then put them into something that could translate into a career that helped Well, or did you still feel like,
Will Bachman 31:48
that’s helpful? That’s helpful. I’d like to talk a bit about one of your courses on Udemy, which is growth mindset, the key to confidence, impact and fulfillment. Tell us a bit about your, you know, that course and what are some of the key exercise you have people do in that course? Sure.
Diane Flynn 32:11
About three years ago, I guess, right, right. Before the pandemic Udemy reached out they had heard me speak at an event about growth mindset, which is of Carol Dweck ‘s body of work at Stanford, I want to make sure she gets credit, she she has been doing this work for decades. And, and there’s lots and lots of books about the growth mindset, if you want to check those out. They asked me if I would do a course because they felt that there was a need for a course on this in their in their course, whatever, in whatever inventory. And so I said, Sure. And they said yeah, you know, you never know how many people are going to watch or whatever. Well, anyway, this week, I will have hit my 60,000 students worldwide. And the reason I think that’s so interesting, is not only because it shows how powerful the Udemy platform is, but it shows how many people are desperate for changing their mindset. And it’s really about getting out of your comfort zone. A fixed mindset is playing it safe, not taking risks, not asking for feedback, not worrying about, you know, failing. And a growth mindset is that kind of uncomfortable space that we have to step into, to really make great things happen that, you know, I for me, every good thing that’s happened in my life has really come when I’ve stepped out of my comfort zone. And so what I go through in the, in the course, is six, you know, what, what is the growth mindset? What does it look like? What does it look like in a person? What does it look like in an organization because organizations have mindsets as well. Some organizations limit growth because they don’t invest in their people, they punish failure, they fire people when they don’t succeed, you know, at trying, you know, a noble experiment. They don’t, they’re not feedback organizations, they don’t help people grow. So those are, you know, there’s a whole bunch of things that define a fixed mindset organization. But then I go into the six roadblocks that I’ve seen through my coaching that hold people back from having a growth mindset. And what I encourage people to do is reflect on which of these are speaking to them, and some people say all six, and that’s fine. You have to start somewhere. But then I have a bunch of strategies for each one on how to address it. So the six are fear, lacking confidence. That’s often called impostor syndrome. Most of us have that if not every I think it’s universal at some point. One is fear of failure. A third is fear of success, which can actually hold us back. A fourth is perfectionism. So many times, I have friends who really want to try something, but they won’t do it until they know they can do it perfectly, I have never done anything perfectly the first time I’ve done it. So getting over that, and just, you know, in design thinking, we call it rapid prototyping, stepping out and trying some new things. And then learning from it is how one can get around perfectionism. And the fifth one is inertia. And that is like, the people I coached that have wonderful task lists, they want to write a book, they want to take a course they want to do this, this this, but nothing ever gets done. So I call that inertia. And the last one I identify is just not knowing what to do. Being stuck being stuck. So really having no clue. And that’s where the personal inventory can really help people get unstuck. Because if you can start to tap into that which sparks joy, that is the best way to find a meaningful something to do. And not every joyful hobby or interest can turn into a job. But hey, I have friends who are professional organizers, they have always found joy in organizing. And now they do it for other people as a very successful career. So starting with what sparks joy can really help create some new ideas and opportunities. So that’s what the mindset course is, is about. And I’m about to you know, give it out for free for a month as a thank you to hating so many students. So I’m happy to give you that link as well. Well,
Will Bachman 37:06
fantastic. We will include those links in the show notes that you’ll send over including the link to your website. Which one of your websites is Diane hyphen flynn.com? That’s D I A N E hyphen, f l y n n.com. So we’ll include that as well as any other links you want to send over. Diane, this has been a fantastic conversation. Thanks so much for joining today.
Diane Flynn 37:35
Thank you. Well, I really appreciate all you do for this community and look forward to stay in touch