Episode 28

The Power of Intent: How Clear Communication Drives Success

June 26, 2024


Randy Wootton
CEO, Maxio
Amber Wendover
Principal, Thinking People Consulting
Tom Perry
Chief Career Officer/Founder, Engaged Pursuit

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Video transcript

Randy Wootton (00:04):

Hello, everybody. This is Randy Wootton, CEO of Maxio and your host of SaaS Expert Voices, where we bring experts who work in and around the space of SaaS and help us understand what’s happening today and what’s going on tomorrow. I am delighted to have two people I’ve known for a very long time join us, Amber Wendover and Tom Perry. Tom and I have known each other basically since I’ve been in a professional setting outside of the military. From [2000], we worked together at Avenue A, which became aQuantive. I liked him so much, I brought him over to Microsoft when we started in 2004, and he worked with us there in 2012 when he made a jump into L&D, and we’ll talk a little bit about what that is and why he had that career change.


Amber also, I didn’t know her back in 2000, but started to get to know her in 2006, when she joined a group that we were doing building out Microsoft’s search engine and search media operations. She spent time at Microsoft, made the shift into L&D in 2008, and then has been deeply involved with unlocking people’s potential since then. And so we’re going to talk about the seven secrets of success today and how CEOs need to focus on unlocking their peoples’ potential. But welcome, Tom and Amber. Really excited to have you guys.

Amber Wendover (01:24):

Thanks, Randy.

Tom Perry (01:24):

Yeah, thanks for having us.

Randy Wootton (01:25):

So maybe, Tom, since I’ve known you the longest, why don’t you start with that career transition. I know how much, when you started as a manager in our organization, how much you cared about the people and trying to get the most out of them and really took on all of our work around management excellence. But what was it that you were like, “No, no, no, this is what I’m going to go focus my career on going forward”?

Tom Perry (01:47):

Yeah, you’re right, Randy. I consider myself to be a people builder. It’s sort of at my core. I love to build teams and culture and organization, and I did that throughout my time at aQuantive and Avenue A with you and throughout my experiences at Microsoft. And for me, I experienced some bumps along my career path. I was experiencing a pretty wild ride at Microsoft, and then all of a sudden, like with most folks in their career at some point, I experienced quite a big struggle, and I was not in an organization where I was thriving. I found work that I was doing not to be at my core strength, and I really struggled for quite a while.


And I really learned that support within that struggle, support for people like me, who were doing really well and then all of a sudden hit some sort of rough patch, just didn’t exist, and so I decided to think about that experience for myself and build a solution, build a business, out of that experience. And so I experienced something firsthand and have been doing some consulting business around tech and people’s experiences within the organization for just about nine years now, and it’s going really well.

Randy Wootton (03:13):

Well, that’s great. I think it’s part of that finding that passion, finding what you really care about and trying to align the avocation with your vocation.

Tom Perry (03:21):


Randy Wootton (03:22):

And just to be clear, you liked it when you were working with us, right?

Tom Perry (03:24):

Oh yeah.

Randy Wootton (03:24):

It was some other group that you were working with at Microsoft where you weren’t feeling fully engaged and-

Tom Perry (03:28):

That’s right. Wasn’t feeling the love. Yes, yes.

Randy Wootton (03:32):

Okay. But I love the other thing, Tom, is you talk about this idea of the forgotten community. Can you define what you mean by the forgotten community, because I think it’s a really interesting sweet spot that you’re focusing on?

Tom Perry (03:43):

Yeah. It’s really that core professional, that varsity squad, I like to call it, those folks who are in the middle, doing the work. I found that a lot of organizations focus on the edges. They think about the new employees, those college hires, those interns who are coming on board, and then, of course, they think about those executives and the senior leaders who are defining the strategy, helping to drive revenue, getting new products out the door. But those folks who are in the middle, those individual contributors, those frontline managers, those high-potential varsity players, unfortunately those folks don’t get a lot of love. And I was in that community for the majority of my career, and when those individuals hit a rough spot or need help with stuff like manager relationships or working with other team members or just feel stuck, there just wasn’t a lot of love there, and there continues to be, I think, a lot of need to support that community.

Randy Wootton (04:49):

I think that’s great. I know just from my own experience, that, and well, I’ve been studying and failing at leadership since I was 18, but just in building organizations, that first inflection point of where you move from an individual contributor to a manager and you’re being recognized and rewarded for all the work you did as an individual contributor, where you were probably out in front and leading the way, and then all of a sudden you have a group of people who aren’t necessarily all type As or aren’t necessarily the strivers, and how do you really bring that initial team together and learn how to be different is a really important career transition. And we called it at Microsoft, and have continued to call it, management excellence. And there are very few companies that are able to invest the money and time in that development area. They do spend time, for example, at the leadership level, to your point, how do we get the effective leadership team? Well, great.


And then you, Amber, similarly had an epiphany in your career, having been at Microsoft with us as a search media strategist, operation and sales, and then in, I think it was 2008, you made this transition to embracing L&D and working with Insights, which we were actually using at Microsoft in terms of helping people better understand their interpersonal effectiveness, their style, et cetera. So tell us a little bit about your career journey. What was the insight that you had while you were at Microsoft about what wasn’t working for you and how this led you down this new path?

Amber Wendover (06:16):

So Randy, I’m a salesperson. I’ve always been a salesperson. I thought I would have a phenomenal career in sales, and was at Microsoft when we were getting MSN.com up and running. And at that time there was a lot of early career people that were starting, myself included, although back then, I was in my mid-20s and felt like a grandma, because we had a lot of people who were starting just out of college and didn’t have business acumen and professional savviness, and didn’t understand how to communicate challenging situations with grace and how to manage up to their leaders.


It happened by happenstance. I just got really interested in the human dynamic of people, and was like, oh my gosh, I can sell. What if I sold things to people? What if I sold people to people, basically? And started helping people understand, okay, this is what it means to have personal power and presence. This is what it means to manage up, this is what it means to communicate, and fell in love with Insights, the personality assessment, and actually was really inspired by one of the facilitators that was at Microsoft and I was like, I want that job. That’s what I want to do for a living. Microsoft wouldn’t give me that job, so it’s been a little bit of a trial and error to get enough experience to be able to end up being where I’m right now in my career. But I love bringing people together.


And I just want to echo what Tom said, we get lost in the middle. And so I think when you go to the middle, it’s almost like you have two paths, you can either stay as an individual contributor and be successful or you have to be a manager. But if you want to switch careers in the middle of that, your functional group, I think Tom and I are actually really lucky that we were in a group where there was this guy named Randy, who was our general manager, who allowed us to switch careers and still have a phenomenal relationship with Microsoft because I actually think that’s really unique, Randy. I don’t think that happens to everybody.

Randy Wootton (08:20):

Well, thank you. I think that one of the advantages of being at a large company is you can help people make transitions, and if you’re focusing on the whole person and trying to figure out what is it that really makes them excited, how do you have them be great contributors in different paths and make that transition is a great luxury. It’s one of the things we take great pride at Maxio. We’re much smaller, we have about 240 employees, but really celebrate those individuals who discover their next adventure at Maxio. Because you spend all this time and money to hire them, and they usually have an enormous amount of experience, background, and knowledge, and to lose that from the organization is crushing, so if you can redeploy them, like we’ve had people come into BDRs who have gone into customer support, who have gone into product management. We’ve had support folks move to product management. I think I have one guy who’s on his fourth job, and he’s only been here like five years.


So I do think there is this balance in terms of coming in, making an impact, making a name for yourself, and if you are one of those people, one of those HIPOs, which both of you all were, how do you meet those folks, as they say today, where they are and say, “Where do you want to be?” And I think having that conversation, which we probably had, which I have with everybody, is, “Tell me where you want to be in five to seven years. What does that look like in terms of the type of work you’re doing, the type of role you want, what industry you want to be, and then what can we do for you, in this case at Microsoft, to get you on that path?” And you have that conversation. It is all about investing in the people, and software is a people business.


Well, great. Well, it’s just been great to watch your careers unfold, and then to reconnect at this stage and see how much you each have done just makes me so happy and grateful for what we were able to share. One of the things we were talking about for this podcast, in particular, was focusing on those seven secrets of success for CEOs, which I’m doing a little bit of writing about, and we shared them with you and people can find it on our LinkedIn in terms of driving results, establishing a winning strategy, shaping values and standards, and a couple of other ones.


And you guys, classic you all, said, “Yeah, Randy, we like the seven, but we think there’s an eighth.” And I was like, “No, no, no, no, there’s only seven. There isn’t an eighth.” But maybe, Tom, because I think you were the one that initially suggested an eighth, can you tell me what you think we’re missing and what should be the eighth secret of success for successful CEOs?

Tom Perry (10:37):

Yeah. Well, I love the concept of seven, Randy, but I am going to push you to maybe go for an eighth one, and your last one around investing in your tribe, I think is so critical for leaders, especially in a startup kind of environment, a group that might be forming or storming or norming. You as that leader have to have support. You have to have your coach. You have to have your executive committee. You have to have the community around you that’s going to allow you to be the most successful. And I wonder if your folks need that tribe, as well. Your peoples’ tribe, I think could be that eighth secret to success, going from that kind of I focus as the CEO or CFO within an organization to maybe more of a we approach. We grow, we learn, we need each other and a community to grow. That’s where I think organizations can really thrive, is focusing on that eighth crucial part of success.

Randy Wootton (11:45):

And Amber, how about you? How would you think about the eighth, the me versus we alignment?

Amber Wendover (11:51):

I echo Tom, Randy. I think you’re going to follow up with us in a week and say, “You guys, I hear you. I have eight secrets of success now.” There’s two things that come to mind. One is a model that I absolutely love is it’s called the It-We-and-I. And so in the most simplest forms, that it is our business. How do we make money? What do we need for profitability? Who do we need to hire? Roles, responsibilities, functional customers, all of that stuff, right? I think we talk about this all the time. We as a company, it has to be successful. The we part of that model is the people with this kind of overlay of cross-team collaboration, our customers, marketing has to work with sales, operations has to work with finance. We talk about kind of cross-teaming all of the time.


And I think this eighth secret of investing in your broader group, the peoples’ tribe, it really hits on the third part of this model, which is the I. It’s where our enthusiasm comes, our engagement, our passion, our purpose, our mission. It’s helping us individually be the best version of ourself that we can possibly be. And Randy, to your point a few minutes ago, I remember so clearly the day I decided to leave Microsoft and I was going to go work full-time for Insights Learning and Development and I wanted to come back and be a facilitator at Microsoft. Insights said, “You have to go to your GM and get them to sign off on letting you turn around and come back.”


And that person was you, Randy, and I was so incredibly scared to send that email to you. And if I would have had this model and really thought about the I, right? What excites me? Where’s my passion? Where’s my enthusiasm? You said yes. I don’t even know if you remember. You wrote back with a yes and was like, “Absolutely.” And I wish there could have been a more collaborative conversation, and almost like I got so worked up and scared that I was letting Microsoft down and I wasn’t able to articulate how my unique value proposition could actually better Microsoft and make me happier. And so I think that I, the eighth secret, let’s invest in our people, is so important.

Randy Wootton (14:13):

It’s funny, because I fundamentally believe in that, but I hadn’t articulated it in the seven, so you’re making a strong case, both of you all are in sales, to argue for an eighth. One of the things that we do, as you may remember probably, back at Microsoft, I’ve had book clubs and had people get together because we always talk about operating at the edge of our own ignorance, and that means exposed to new ideas, new concepts, and how do you grow. We’re doing that at Maxio, as well, and we read a variety of books.


The one that I’m reading right now is Cultures of Growth, growth cultures versus genius cultures. And this idea of how do you create that environment, what you guys are describing, where people feel like they are empowered to be their full self, they’re feeling challenged, and they see it as a collaborative experience versus what I think Microsoft was when we were all there, was it was really a culture of genius, genius culture, where you were rewarded and recognized for the best idea. You would walk into the meeting and the person who won points because they were the smartest person in the room would take everyone else out.


And I give an enormous credit to Satya, because all the people who stayed there and done very well with Satya and the stock price, has said that within the four years or five years that he was there, he was able to absolutely transform the culture through this focus, I think to your point, around leadership and management and helping people unlock their potential. So I guess it’s a question for you all, are you familiar with that growth culture versus genius culture construct, and how do you use that in your own coaching or experience?

Amber Wendover (15:41):

Yeah. I love the book, Randy, that you’re talking about. I also love Carol Dweck’s book Growth Mindset, I think-

Randy Wootton (15:47):

Which is the original text, and this woman, I think it was Mary something, I was looking for it, built on that, and I think had her as her advisor.

Amber Wendover (15:54):

Yes. Yeah. It’s brilliant, right? You know I have a 20-year-old son, and even in college they’re talking a lot about growth mindset and creating this space where I think that, at the end of the day, we’re all human. So if you believe that we’re human, and bear with me for a second, if you believe that we’re animals that belong together, right? We’re pack animals. Randy, I want you to like me. Tom, I want you to like me. I want to have a good hour with you guys today. And so if we’re animals and we belong together, we’re meant to be together, and so in order for us to thrive together, we all need to be at our best.


And so I think this whole notion of a growth mindset and a learning organization, it’s like at the end of the day, the way I think about this and the way I use it is like what do you need to be at your best, and how do we put you in a culture that allows you to be at your best and values that unique perspective? And then with values and competencies and all the structure around a culture that a company has, it’s like then we can put the building blocks together so that we’re actually building whatever it is we’re going to build. I don’t know if that makes sense.

Randy Wootton (17:04):

Yeah. No, that’s great. And so Tom, how about you? This growth mindset, the growth culture, which is the newer idea, are you playing with that or seeing that play out in your consulting?

Tom Perry (17:17):

Yeah, absolutely. I think that is crucial. I mean to think in bigger terms, to think around the corner, to be more strategic overall. But I’ve really found, Randy, that in order to do that effectively and to lead cultures into this new, high-paced, ever-changing environments, people miss the real basic core of humanness, which I have found to be authenticity. I have found that people in high intense cultures, like we experienced at Microsoft, where you have to be the best in the room, you have to come up with the best idea, folks become a little robotic, and they feel like they have to have the best answer at all costs.


And I have learned over time and in my consulting business that the best leaders are ones who show up as their true selves, who are authentic, who don’t have all the answers, who are inspiring, who can have meaningful conversations, who talk about their weekends, who talk about their families, they want everyone to get along and to work well. And that’s really the secret to great leadership and growth mindset and ever-changing environments, being that human is really the path to that success.


And I’ll go back to one thing you told me, Randy. This is during my early days as a manager of Microsoft. I had made that transition from IC land into manager land about a year after I started within the company, and I was really stressed about all of those elements of management that we’re all taught to convey, the hypercommunicative, all about results, making sure you’re maximizing people’s strengths, having the swim lanes defined. And I remember coming into your office and having a one-on-one with you, and you said, “You know, Tom, people don’t care about that stuff as much as your manager. They want to know you, they want to know Tom, they want to know who you are and what makes you tick and how you’re going to get them to a success.”


And that was so impactful to me. Taking that shield down, taking that wall down, not being that robot has just been really impactful for me, and so I take that into my business today and help people every day be more authentic, and that’s what I’ve found to be the real strength to being a good leader.

Amber Wendover (19:51):

I think about you and actually Anna Collins, who was a leader when we were there, and I was young in my career, but you guys, I think, created a growth culture without the title of it being called a growth culture because we had the ability to explore and experience and make mistakes. I made so many mistakes at Microsoft, and I remember different leaders throughout my time at Microsoft said, “Amber, what did you learn from this?” And as long as I had a learning, nothing was held over my head. And if I couldn’t figure out the learning, you guys helped me find the learning, right? Anna was notorious of this. And so this whole premise of growth culture, we’ve been doing it for decades, it’s just now we have a label. And I think if you’re a small business, a startup, remember that you’ve got to create a space for your team to be successful, and part of that success is making mistakes and figuring out who they are.

Randy Wootton (20:52):

So let’s go there. I think that you guys have both… Well, thank you for that walk down memory lane.

Amber Wendover (20:53):

You’re welcome.

Randy Wootton (20:58):

I appreciate that. I do think that was kind of both Anna, who was my boss at the time, who’s a very close friend, shares the same commitment to people and development of people. Look, we were both in the military, and I think a lot of people are like, “Well, the military is robotic.” Not really. The military, people don’t get paid a lot of money and they’re out there to do missions and they’re working super hard. And so you’ve got to get at the essence of mission-oriented, you’re there to do service, et cetera, but then also how do you make people successful because they’re part of this machine? And so I do think that was something we bring with a real empathy and desire to help people become their best.


The thing that you mentioned, Tom, and you reinforced, Amber, is this idea of authentic leadership. And honestly, it’s interesting I gave you that feedback way back then, Tom, because it’s something I work on regularly.

Tom Perry (21:46):


Randy Wootton (21:46):

Because I think, with my disposition and personality, I tend to be about results, and I want to get to know you in the work that we’re doing. And so sometimes people feel that’s very transactional or it could be intimidating. It could be like, “Okay, what did you do this week? Let’s talk about it and let’s solve problems.” And to your point, Tom, part of it is backing up and just letting them see who you are and being a bit vulnerable. And I think I may have started this at Microsoft, but at Maxio I send out, it’s not consistent, it’s probably every couple of weeks, a thing I call View from the 30,000 Feet.


And it’s usually I’m coming back on an airplane from somewhere, and I’m giving a perspective on the meetings I’ve had or where I’ve been, in part because I remember when I wasn’t CEO, I always wondered what the heck CEOs were doing. And part of it is also just speaking to the pathos, when Aristotle talks about eros and logos and pathos, it speaks to the humanity of, “I was at this trip and it’s been a long time being on the road and I can’t wait to see my family,” but there’s nothing transactional in it. There’s nothing about, well, sometimes they’re about business results, but the whole idea is to provide a view into who I am. And so I hope when people who knows how many read it, when they see, it’s like a different side of me. And as CEO and as leaders, I think it’s so important to show that you’re human and that you make mistakes.

Randy Wootton (22:59):

I think it’s also important, especially in this hybrid community, hybrid work, the how do you create connective tissue with people? So one of the things that this team told me in my executive meetings was I tend to just jump into the results and, “All right, let’s talk about what happened last week. Let’s get going,” and we do 10 to 15 minutes a round of good at the beginning of every executive meeting, and the round of good is what good thing happened to you over the last week, over the weekend? Did you go off and do this? Did you do that? And it’s this really nice, connective time which I, in my core being, am like, “We’re wasting 15 minutes. We could go solve another problem.”


But I think, to the point that you guys are both making, is for an organization, especially in this new reality that we’re working in, is how do you create human connections, right? It’s all about relationships. So maybe I’d ask you guys, maybe Amber, you could start, is what are some of the specifics? You’ve worked with a bunch of companies now, a bunch of early-stage companies, when you go in and you’re talking to probably mostly a technology leader type, what are the recommendations you’re making to them so that they can build this growth culture so that they can help set the context to unlock people’s potential?

Amber Wendover (24:10):

I think the first thing that we all need to do, no matter what level we are in the organization, is think about our brand. And so even when I listened to you, Randy, and you talk about you’re results-oriented, getting things done, I mean, part of the reason why we reconnected is because Tom and I reached out to you and said, “Hey, Randy, we need some help.” And you were like, “Oh, I have an idea. Let’s do this. Let’s get on a podcast.” So it’s like own your brand, and I think knowing your brand and owning your brand right there humanizes you.


So I think one thing that everybody could do, CEO, all the way down to the organization, take 20 minutes, turn off your computer, turn off your phone, and sit down, and I’m not telling you to leave your job, so don’t worry, but it’s the last day of your job and we’re all there to celebrate you, what do you want said about you? Write that down and feel really good about that, because if you know what you want said about you on your last day of your job, now you have it written down, now you can put it on your piece of paper or you can tape it to your desk, you can have it in your journal, on your phone, reflect on that and say, “Okay, am I doing the things every day that aligns to this impact statement that I want to be said about me when I leave my job?” It’s the most simplest, but yet maybe the most powerful exercise that I think all of us can do.


And then the other thing I tell people is state your intentions, and even if you have unintentional impacts. So it’s like knowing that you’re a drive for results type of guy, Randy, then just tell me that, right? “Hey, I’m a drive for results type of leader, so this is what I do. And Amber, if you need something different, let me know.” So I think as a leader, when you ask your team, “Hey, if you need something different, let me know,” that creates a place where we can have a discussion and a dialogue. And so if you say your impact and if you need something different, let me know, then, “Hey, Amber, what’s your impact?” Right? If you’re my leader, Randy, “Amber, what’s your impact? What do you want your impact to be?” And I think you create a discussion and that creates a culture of growth, authenticity, trust, I mean all the things we’ve been talking about.

Randy Wootton (26:19):

Those are two great points. Tom, did you want to build on either of those, or do you have another suggestion before I react?

Tom Perry (26:26):

Yeah, I’ve got a couple. And my focus, Randy is more on those frontline managers. So Amber is looking at the executives and those senior leaders. I love that middle, varsity squad, as we talked about earlier, the newbies to management, the HIPO community. And I totally agree with Amber, I think your brand is critical. I call that your story, so what is that elevator pitch that you have as your discussion around where you want to go and what you’re doing? You know, Randy, that people have those kinds of conversations all the time, whether it be at the water cooler or over Zoom or during formal career discussions, having that is critical. I also love the intent piece. I think that is critical to management, letting folks know where you are headed in a particular conversation or where your lens is in a particular dialogue.


I also think it’s really critical as new managers, in particular, to let go. I think that new managers who are coming from that IC community have a tendency to hold onto that control, try to have that power, and I found real strength comes from those leaders who can empower individuals, have folks think about solutions. You don’t have to have all the answers. That really has helped leaders evolve and grow and become true organizational heads over time, so that’s been one piece of advice that I give them.


And then I also think, just sort of tactically, I think as you’re doing within your current organization, Randy, I think creating time just to be human is really critical. So having those first few minutes to talk about the weekend, to create time maybe at the end of a discussion around feedback, so how did this conversation go for you? What did you learn from this? What are you going to take away from this conversation? I think in lots of Zooms and team meetings that we’re doing, we’re go, go, go, we’re solving problems throughout the whole hour, and if we can just tactically give us some room to talk and to connect, I think that can make a world of difference, too.

Randy Wootton (28:32):

Great. Great recommendations. A couple of specifics that we’re doing at Maxio right now, for example, is the book club. So the book club, I love reading books, and so people find it… We have had 5 to 10 people show up for these book club meetings, but it’s an opportunity to get us all to know each other, and it’s something I really like doing anyway, so I facilitate that. We also have water cooler times where people just get together and chat. We also have a program where, I think it’s like once a week, we have someone who says, “Hey,” you show up, and they talk about who they are and where they’ve been and what they’ve done. And so how do you create these opportunities for connective tissue when you don’t have as much of an in-person dynamic? I think that’s great.


I loved your comment about the personal brand, Amber. I do think now I’m 56 or something, you start to think more about your legacy, like what have you done and who have you lived? Who’s going to show up at your funeral? What are you going to fill between the birth date and the death date, other than the dash, right?

Amber Wendover (29:31):


Randy Wootton (29:32):

I went through this exercise. I’m in a program, it’s a leadership program I’m doing for a bunch of years, it’s called Pathwise, Pathwise Leaders. Highly recommended it. It’s a yearlong program. It’s a four-year sequence, and I’ve done it several times now because I’ve just got to keep learning it. But we did a exercise this last time, which was for the people who love you, who know you very well and who love you, how would they describe you?

Amber Wendover (29:56):

Love it.

Randy Wootton (29:58):

What are your strengths? How do you show up? And so part of that is the positive idea of the legacy, but you do it through the lens, pick two people. Pick your mom and pick your best friend or pick someone at work, what would they say? The people who love you, not the critics, but the people who love you. And I thought that was a really powerful exercise for me because I know, as a CEO and, gosh, I don’t know, eight, nine years now, in roles at different companies, it’s super lonely. And so part of that idea of having that peer group and that build your tribe, for me, it’s around a mentor who’s been in the context you’ve been in who can give you specific advice. It’s about a coach who can help you with interpersonal effectiveness. So managing the board, managing your team. It’s about having a peer group. So I belong to Vistage. There are other groups out there, like YPO and EO, where you’re able to be in a safe space and talk about things you’re struggling with.


And the fourth component is just having a peer group of people who know you really well and who love you, and when you come to them and you have some crazy idea they’ll say, “Well, that doesn’t seem resonant with who you’ve been and who you say you want to be.” And I think the CEO job is really lonely, and if you don’t have that dynamic and support structure in place, it can feel like it’s you against the world. And so this exercise of thinking about who loves you and what they say about you is a really affirming opportunity. And so to your point, Amber, I think it’s both this building your brand and taking a minute to say, “You’re okay, we’re okay.”

Amber Wendover (31:26):


Tom Perry (31:26):


Randy Wootton (31:27):

The other thing you said, which is one of my favorite tools that I use, is the most respectful interpretation. So when you’re having an issue with someone, you’ve got constructive tension, you feel like it’s gotten a little personal, it’s to say, “Well, what could be the most respectful interpretation for what they’re saying?” And so you try to give them the grace or you’re gracious in letting them, they had a bad day, their kid was sick, they were up all night, or something along those lines, and try to say, “What could their intention be?” And if it’s not clear, ask them. Say, “So right now, I’m not feeling great about this or I don’t fully understand. Tell me what your intention is of your questions or the intention of this line of inquiry.”


I know, to your point, Amber, with my personality, it is often super helpful to just say, “Hey, here’s my intention. This is what I’m trying to accomplish. If this isn’t working because you’re feeling the dynamic going sideways, let’s back up. Take a break, go for a walk, come back. But my intention is to be in relationship with you. My intention is to drive business results. How do we do that most efficiently and effectively?” And it’s like a reset for the conversation and the experience.

Amber Wendover (32:36):

Randy, I thought of two things when you were talking about it’s lonely at the CEO at the top. I went through Conscious Capitalism leadership training when I worked for Whole Foods, and one of the things that they encouraged us to do, which I thought was brilliant, is first of all, they reminded us we’re having impact on each other and we don’t even know the impact that we’re having.

Randy Wootton (32:55):


Amber Wendover (32:56):

So they said, “Find somebody that has been in your life 10 or 15 or 20 years ago, call them up, ask them how you impacted them.” And it is such an amazing exercise. If we all did that at work, I mean, think about today, Randy, I told you a story about me being worried about asking you to let me come back to Microsoft. That story impacted me way more than it impacted you, right?

Randy Wootton (33:18):


Amber Wendover (33:19):

And your response was just, it was awesome. And so I think if we all knew these tiny, little moments that have big impact on each other, and if leaders would ask their team members and former team members, I think that would be really helpful. And then on most respectful interpretation, that’s one of my awesome tools, too. I love it. And we’ve evolved it a little bit to the… Have you heard of the rule of three when it comes to MRI?

Randy Wootton (33:46):


Amber Wendover (33:46):

All right. I know you’re a rule guy, right? A rule of three, it’s very [inaudible 00:33:50]. First time somebody rubs you the wrong way, just let it go. Give them MRI like, “I’m going to assume that we had a miscommunication. You’re having a bad day. I’m not going to let it stick with me.” Second time, that same person, something happens, rubs you the wrong way, second time, it’s a coincidence. So maybe we have a 9:00 meeting, I’m running 15 minutes late, maybe 9:00 is really hard for me because I’ve got to get the kids off to school or whatever.


So I’ve been late to the meeting two times. You don’t want me to be late. So you might say, “Hey, Amber, I’ve noticed the last two times we’ve had this meeting at 9:00, you’ve been late. Is there something going on?” And then I can say, “You know what, Randy? Yeah, 9:00’s really hard for me. I’ve got to get the kids out the door, I’ve got to get the puppy, whatever. If we could start this meeting at 9:30, that would help me.” So you’re like, “Great, we’ll start the meeting at 9:30.” And then you tell me punctuality is really important to you, right?

Randy Wootton (34:44):


Amber Wendover (34:44):

Third time something happens, start the meeting at 9:30, Randy, I’m late. Third time, it’s a behavior.

Randy Wootton (34:51):

That’s great.

Amber Wendover (34:55):

You have to address that behavior. You have to hold me accountable, set expectations, let me know if it’s going to get in the way of my job, my performance or whatever. Because if you don’t hold me accountable to that behavior and you ignore me, or what they say now, you ghost me, and you just stay quiet about it. You’re excusing my bad behavior, so you’re in this with me. So I just think MRI is such an awesome tool, and then I love the rule of three on top of that.

Randy Wootton (35:22):

Oh, that’s great. And then the other thing is if you’re a leader and you allow that behavior, you’re sending signals to the rest of the organization that the punctuality is not valued. And you know me, if you’re not five minutes early, you’re already 10 minutes late, so let’s just be clear about how important punctuality-

Tom Perry (35:37):

We’ve learned from the best.

Randy Wootton (35:40):

It’s like high school, just have your meetings go for 50 minutes and then you’ve got 10 minutes to go to the bathroom, and then get ready for your-

Amber Wendover (35:46):

Let’s set the norm that the meetings are running for 50 minutes.

Randy Wootton (35:49):

That’s right. Set the norm. Set the norm. Tom, did you have a reaction to that, or I had one other thing I wanted to bring up, but please, was there something about the MRI or the intention that you thought resonated for you and what you use in your practice with the manager group?

Tom Perry (36:04):

Yeah, I just think that creates such clear communication. I think as you mentioned before, Randy, with all of our hybrid working styles and being on Zoom and Teams, it’s now important more than ever to have crystal-clear communication. So I think having intent, having that MRI, that’s just going to help you be a great leader and communicate really effectively with your team, whether they’re next to you in the office or across the globe.

Randy Wootton (36:31):

I think, just two other thoughts. One is I love Insights, and I’ve done DISC and I’ve done all those other things. I talk to people about if you do it, one, it indicates, so for CEOs that are listening and they haven’t done that, I think it’s an incredible mechanism, relatively low cost, we’ll talk about this in a second about how to budget for this stuff, but Insights is a way for you to create better understanding of how people interact with each other and communication styles.


I tell people it’s like a year’s worth of one-on-ones. If I get your Insights profile and you validate it’s true or 90% true and I give you mine, then all of a sudden you can have this really powerful conversation about, “Oh, you process the world this way. There’s no one right way. There’s different ways,” and I think building that collective understanding of the different colors and how they show up. I use it every single day. And people will ask me, “Randy, what’s your management style? And I will say, “Well, I don’t know. Who am I managing? What is their essence, and then what are we working on together?” Because it could be very different.


The other thing which you called out, Amber, which is something relatively new I’ve started to do, is I have this working with Randy document, and it was in part, I built this and it’s like, “Here’s my expectations. This is what it means.” So, for example like, “There is no space between the line.” When I’m giving feedback, “The report doesn’t look good,” there is no extra context, it’s just, “The report doesn’t look good,” and so don’t read into it.


And there’s other components on that and running the one-on-ones, and I’ve just found over the years it’s been helpful to just say, “Here’s my operating system, my ReadMe file.” And to your point, Amber, we can have some conversations about what your ReadMe file is, my ReadMe file, and how we can build better interactions. I would say at this stage of my career, I am more excited about saying, “Here’s my ReadMe file, and let’s make sure it works for you,” and then especially with executives, right?

Amber Wendover (38:17):


Randy Wootton (38:17):

Because as executives, they’re functional experts on an executive team, your expectation is that they’re going to be able to be the smartest person in the room around that function, but building the connective tissue across the first team is really important. So us understanding, how am I going to co-lead with the head of engineering, which is, I mean, I’ve been in technology for a long time, I’m not a computer scientist, but how do we work together where there’s space for us to co-lead? That working with Randy document allows me to be able to say, “Hey, I’m going to ask questions.” And they may be questions you think, why is he asking? This is absurd. But here’s my intention or here’s where that’s coming from. So I think that’s great.

Amber Wendover (38:55):

If anybody needs an Insights profile, we can get them one. We can get them one, Randy, if any of your listeners-

Randy Wootton (39:00):

Yeah, no, I think this is where we’re having you here-

Amber Wendover (39:03):

We can get them an Insights profile. In the comments section or something, I can give you a promo code, because Tom and I both use that a lot and I love it. When you think about someone that has a lot of data and needs information, and you’re just reminding me, Randy, even if just your style, it’s like I always tell people, the more questions someone asks, chances are the more interested they are in whatever you’re talking about.

Randy Wootton (39:23):

Right. Yep.

Amber Wendover (39:23):

So it’s like we get scared by your questions, but instead I want to be excited by your questions because you’re engaged, you’re listening, you’re contributing, so I think there’s a whole bunch that Insights can do. And the operating system and your ReadMe file, that’s a great tip, too, and how many ReadMe files conflict.

Randy Wootton (39:46):

Yeah, that’s right. Well, that’s where you’ve got to be clear, how’s it going to work. I’ll give one last tool, and then I want to talk about how do people engage folks like you and how do they think about the budget? So my last trick is, I remember being in Microsoft and you would spend all this time to build a presentation, and one of my biggest presentations, another story at some point. And then out of the gate, the executive you’re presenting to just jumps on, and you don’t even get into your flow yet. And so one of my tools I use is when I’m at my best is I’ll tell, “Hey, present for 45 minutes, I’d like to hold the last 10 minutes for me to ask questions.”


During that time, I try to find at least two things that they did really well in the presentation. I write down all my questions. Often, you find that your questions are answered through the presentation. You’ve just got to let the person tell their story. And then the third bucket is guidance. Here’s the one to two things that I think you need to do going forward. And so in doing that, if you let the person get through their [inaudible 00:40:43], and you can ask clarifying questions, but you just let them get into their story and you let people be great. And you start off with the feedback was, “Here’s the two to three things I think you did really well in this presentation,” their openness to the feedback and guidance when you give it is radically different.


They felt like they got in, they got to dance their gig, they got validated and they got a couple of points, and they’re going to go off and go kill it. And so I think that’s another one of those tools if you find… You should not be the first person, as the most senior person in the room to speak. That was something I learned, Tom, from Brian McAndrews.

Tom Perry (41:20):


Randy Wootton (41:21):

He would be CEO of Avenue A/aQuantive, he would let everyone else speak, and at the very end, he would come back with one or two things to consider. I’m not that good, but I think of that as the model, the paragon of how do you let people really be extraordinary in meetings?

Tom Perry (41:33):

Yeah, that’s so true. And especially for new managers, as I mentioned earlier, that tendency to jump in, to be that solver, to come in and to have all that immediate feedback. I tell those new managers to hold up, have some silence, be a good listener, like you said, take some notes, create space within that meeting so you can have questions. Those tactical efforts can really make a big difference, not only for you as the consumer of that information, but for the person who’s presenting to you, which oftentimes that’s a huge opportunity for them. They’re super nervous, they want to do well. That really impacts them, too.

Randy Wootton (42:12):

Yeah. I think people forget what it’s like when you’re walking into the office of the CEO or you’re walking into the director. And I think at Microsoft, we ended up with a lot of people where the director would, if not take credit for the people that were working below him, definitely felt like they had a lead and tell that story versus if you’re in a space, like we were talking before, where mistakes are okay and you’re using it as a learning opportunity, that’s the opportunity for that first-time manager to present. And of course, you want to give them coaching upfront, you want to give coaching afterwards, but resetting the expectation of the people in the room that this is a learning opportunity. It’s not a judgment activity where you’re going to rip them apart.


Okay. Well, in the last three minutes we’ve got, look, everybody says it’s a good idea, they want to do it. You’re in sales, Amber, how do you help people think about budgeting for the investment in CEO coaching? And Tom, as you think about unlocking the middle, the forgotten community, do you have a rule of thumb in terms of how much money people should be spending on L&D per employee? We budget T&E, what should we budget for L&D?

Amber Wendover (43:18):

So my rule of thumb is you should budget 5 to 10% of everyone’s salary for L&D. Super simple. And if you could take 5% of my salary and invest it back into me, you’re going to get three, four, five times of that from my potential. So if you just want a quick and dirty, I would say, especially your high performers, whoever you want coaching, 5 to 10% of their annual salary, dedicate that to some type of coaching, learning and development, the program, there’s lots of programs out there. And I think with working with an outside consultant like Tom and I, the more people you invest in, kind of the bigger bang for your buck. So you think about Insights, right? There is a cost per profile, which is a few hundred bucks, and then some facilitation fee, but the value of that, it goes way beyond that program. So that’s my quick answer. What do you have, Tom?

Randy Wootton (44:11):

That was great. Tom?

Tom Perry (44:12):

Yeah, that’s right. 5 to 10% is what I’ve heard, as well. And I think when it comes to the actual program and the content and the curriculum that is provided around this stuff, I think one of the pitfalls I think most organizations are experiencing is that they feel like they have to define what that is for folks. And I have found that the best organizations, whether you’re huge in size or just starting out, is to let the employees come up with what they want to build their learning plan.


So that could include some coaching like with us. It could include some real-life transforming content like Insights. It could include going to conferences or taking online training or getting certified in something. Let the employee be the person who is defining that for themselves. Now, of course, you might have some organization-wide stuff around topics like better communication or how to deal with conflict or things like that. But I just find that letting the employee be creative in how they want to spend those funds, that can really be the biggest bang for your buck, because they are invested in what they want to actually get better at.

Randy Wootton (45:31):

Yeah, I think that’s great suggestions on both fronts in terms of you need a commitment to it, I would suggest probably like what we did, we hired an enablement director, and that person is helping us to build enablement programs, to build the skills broadly from our leadership excellence program, our management excellence program, and then very specifically, the courses that we want everyone to take to learn about product. We rolled out Insights across the whole company.


But then beyond that, Tom, I think you’re right. People have to participate in their own rescue, they have to participate in their own development. And if they have ambition, to your point, Amber, the ones that are the HIPO that are always like, “I want more, I want more, I want more,” is how do you help them give them access to funds or an understanding with an expectation that they’re going to go someplace, learn it, and share it?

Amber Wendover (46:17):


Randy Wootton (46:18):

Well, you guys, we’re at the top of the hour. It was awesome catching up. Thank you for your insights and the experiences you’ve been sharing. If people wanted to connect with you, is the best way through LinkedIn or is there a website you want them to go to, Amber, or what would be… They need coaching tomorrow, where do they go?

Amber Wendover (46:34):

They could do either. They can connect with me on LinkedIn, which is Amber Wendover, A Wendover, or our company website is thinkingpeople.com.

Randy Wootton (46:43):

Thinkingpeople.com. And you, Tom, I know you’ve worked with Amber. Is there another way you’d like people to check in with you, or is that the best?

Tom Perry (46:49):

Yeah. So, of course, you can go through my personal LinkedIn, as well, or my company is called Engaged Pursuit, and so I’ve got a company page on LinkedIn, or my website is just engagedpursuit.com.

Randy Wootton (47:01):

Awesome. All right, y’all. Thank you.