110: Maximizing Personal-Professional Growth with Jonathan Raymond

Pete Mockaitis
Jonathan, thanks so much for joining us here on the How To Be Awesome At Your Job podcast.

Jonathan Raymond
Hey Pete, thanks for having me on.

Pete Mockaitis
Well, sounds like you’ve got so much great stuff. I’d love to dig right into it. Can you start us off by maybe giving us some background or context with your philosophy that personal growth and professional growth are in fact the same thing.

Jonathan Raymond
Yeah. In my career I kind of bounced back and forth between business guy and personal growth, spiritual seeking for about 15 years. I had graduated law school in the late ’90s and went on my own personal growth adventure, diving deep into meditation and yoga and different forms of psychology.
And at the same time I was founding and growing businesses. I worked in the tech industry, I started a renewable energy company, and then without any plan to end up there, as life has it, I ended up in the business coaching field, which was at least theoretically supposed to be this place where personal and professional growth go together.
And I was surprised at how little integration there was, and how difficult it was to do. So many people talking about… You read leadership books and there’s always quotes from famous personal growth and spiritual teachers, but when you work in those companies it doesn’t feel that way. And so that was puzzling to me, and I struggled with that myself. And so that’s where I came to launch Refound and write the book out of my own experience of being a CEO and seeing how hard that is – to create a culture that goes beyond stated values and into embodied ones.

Pete Mockaitis
Oh, that is well said – stated values versus embodied ones. And I think I’ve seen a lot of hollow mission statements and then a few fantastic organizations that really lived their values and operating principles, and the words mean something. So could you maybe give us an example on how the notion of dividing personal and professional growth seems crazy, or an example of how personal and professional growth are absolutely like yin and yang, or supportive or integrative or the same?

Jonathan Raymond
I think that the challenge that most managers have is, we stop short a truly personal conversation. And an example that I think of sometimes, I used to have a guy on one of my teams – this was 4-5 years ago – and he was coming to the office and he was depressed. He just was not in good way in his life. And he had some talent – he was good at certain elements of his job – but the way that he was showing up was not good for the team, and I could tell he just wasn’t happy.
And I hesitated for a while; I didn’t know how to bring up the subject, I didn’t know how to talk with him about it. And then I kind of worked it out of myself and I just said, “Hey, you just seem a little out of it.” And we had one-on-ones that we were doing, and I said, “I don’t know if you know this about yourself, but when you come to the office you seem kind of depressed, and your energy is really heavy. And I just wondered, do you know that about yourself?” And he said to me, “Oh, thank you so much for saying something. I’m just really going through a rough stretch and I just didn’t know how to talk about it. And I thought I was masking it and keeping it out of work, but I guess I’m not.”
And I didn’t ask him what was going on, I didn’t try to be his therapist, but I just let him know that I cared and that I was listening, and that it mattered to me. And that how he showed up mattered to our business and to our organization, and that he had me as a support to be able to move through whatever that challenge was, but that they weren’t two things. It wasn’t, “Go fix your depression in your personal life and then come to work, and that would make everything fine.” It’s “Well, what can we do? How is that maybe showing up here? Maybe there are elements that are showing up in your professional life that are part of the problem. What can we do about that?”
There are these patterns and these ruts that we all get stuck in, and we get stuck in them at work. And so to be able to have open conversations and to have your office be a place where people can trust that they can share a little bit about what’s going on with themselves, they don’t have to present the perfect personality – that’s at least the start of that conversation.
And then a lot of it comes from the manager being willing to say to somebody, “We’ve talked about this a couple of times, and this just isn’t how we do it here. And I want to talk with you about this so that you can grow, but you’ve got to be up for that journey.” That’s not a professional or personal; it’s both. If a manager or a leader is willing to confront somebody in a compassionate and open way and say, “Look, this is our standard. These are the values that we say on the wall, and there’s a gap. Are you up for changing it?” 99 times out of 100 people will say “Yes”. One time out of 100 someone will dig in their heels over a long period of time and not move, and then that person has to go.

Pete Mockaitis
Okay, thank you. That really kind of makes it real; very helpful. So I really was digging your book; the subtitle was perhaps the most inspirational I could think of in recent memory: Become the Leader Your Team is Waiting For. It’s like, “I want to do that.” And then the main title there being Good Authority. So can you tell us, what do you mean by each of those phrases – “good authority” and “become the leader your team is waiting for”?

Jonathan Raymond
We’ll start with maybe the second part of it. And this is from my own personal experiences – I thought that I was giving feedback, I thought that I was setting clear expectations, I thought that I was doing the things. And this was both at the C-level and also as a junior manager in over 15 years. I thought that I was listening, but I wasn’t. I thought that I was empowering people, but I wasn’t.
And what my teams – and one team in particular, that I think about a lot – what they were wanting from me was not just to listen; there’s a lot that I needed to grow to to listen better. But they need me to act on what I was listening to. They needed me to hear their frustration with what was happening with other directors or managers and leadership, and they needed me to advocate for them and say, “Look, here’s what I think is going on on the team, and here’s why I think this is happening. And we need to make a change as leaders.”
Because I was in a position of power to do that. And that’s what they were waiting for, and they were waiting for me not to cuddle them, not to tell them everything was going to be okay, not to give them a gold star. They were waiting for me to challenge them, they were waiting for me to say, “Hey, here is what excellence looks like to me in this role. And you’re doing some of those things, but here are some areas where there’s some room to grow. Are you up for changing that?” And then when I would frame that conversation the right way, then I was becoming the leader that they were waiting for. Up until that point it was all talk. So that’s where I got the second part of it.
And the first part of it is… I think if we look back, we know about top-down, command and control, authority, and those models. Those models have been around for a long time; you still see them out in the world, they still exist. That authoritarian style still exists. Doesn’t work for most people; it certainly doesn’t work for millennials and most modern employees – they doesn’t respond well to authoritarian leadership styles.
But here’s the thing – what we’ve done in the last 10 or 15 years, in particular in the US is, a lot of companies, with the best of intentions have tried the “No Authority” model: “We are all on the same team, isn’t it all great here? Blah blah blah.” And that doesn’t work either.
And so Good Authority is my attempt to find that middle ground. It’s not all-powerful, top-down authority, but it’s not no authority either. It’s mentoring, coaching, it’s that spirit of being willing to say, “Hey look, I’ve been there a little bit and I know some things and I have some experience. I’m not perfect, but I’ve been around this topic or this skill a little bit longer than you have and I’ve got some things to share with you to help you grow.” That’s good authority.

Pete Mockaitis
That is helpful. And that was well said about “No Authority” ’cause I came from a management consulting background and we used a tool called “Rapid” to determine sort of decision making roles. And so it’s sort of like, “Who has the D? Who has the power to decide?” And in a fair number of organizations it’s either like, “We don’t know” or “Kind of nobody” or “Take a collaborative approach”, which is a bit of a cop-out to, “We’re scared to say that this guy is in charge and you’re not, or vice versa.”

Jonathan Raymond
Yeah. And the thing is that authority is not the problem, and that’s really what the book is about. Authority is not the problem; it’s when we show up as a jerk within a position of authority, and we micromanage. But it’s not authority; authority is just a structure, it just says, “Hey, I’m responsible for the team, for the results of this team. I also have data that you don’t have. But I also have job responsibilities that you don’t have, and you have job responsibilities that I don’t have. We have different roles on this team, and that’s fine. There’s not a problem with that.”
There’s only a problem when people don’t feel seen, when people don’t feel valued, when they’re on the employee side. And when employees a lot of times… And this is a huge gap right now – employees don’t know how to challenge their boss in a respectful way. So they either don’t do it, which is bad for the culture, or they lash out. And this happens both ways.
At this point in human history we’re developing our expertise in being able to be real-time with one another, to be able to say, “Hey, that thing that you just did – that really upset me.” And to understand how to communicate with another human being in a way that’s candid, direct, but isn’t accusatory – we’re learning, as human beings. And that’s on both sides of the management and the person in employment role, in that context. And so that’s really what needs to happen, is to open up those conversations, and that’s so much of what the book is about.
Pete Mockaitis
It sounds like you’ve teed up the very next question I was curious to hear, and that is, you’ve got a chapter in your book entitled “The Perfect Conversation”, which I found very intriguing. What makes a conversation perfect and how could we have more of those?

Jonathan Raymond
The perfect conversation is the third step in a tool that’s in the book, called “accountability dial”. And the perfect conversation to me is one where everything is out on the table. The perfect conversation is not, “We have figured it all out and we have all the solutions.” The perfect conversation is… Let’s say I work for you, Pete, and you want to help me improve the way that I keep agreements. Like I tend to be a little sloppy around the edges and sometimes I keep my agreements and sometimes I don’t. And you want to help me grow.
So the perfect conversation is a conversation where I’m willing to look at that pattern, you’re helping me see that pattern and how that’s not just about work. You’re saying things like, “Hey Jonathan, I really appreciate that you’re open to having this conversation around keeping agreements and how important that is. And I’m just wondering, is that something that shows up for you in the rest of your life also?” “Oh man, yeah, that’s something my wife is always telling me about.”
Whatever the thing is where there’s a bridge. And it’s not your job as a manager to create the bridge; it’s your job to guide somebody to see, “Wow, that’s not just about work. The way that I manage my calendar, the way that I take risk or don’t take risks – that’s a statement about who I am in some way. And thanks so much, Mr. Awesome Manager, because you’re showing me how to use my job not only to get the team result accomplished, but also in a way that I’m going to become a better version of myself. I’m in, let’s do this.” That’s the perfect conversation.

Pete Mockaitis
That does sound exciting. And so what are some, I guess, best practices or tips for getting there more often?

Jonathan Raymond
The most important thing that managers need to do, and the online course that we do is really based on this, is creating structure. You can go from 0 to 60 when it comes to personal growth. You have to give people data; you have to point out, “Hey, I noticed this thing – you seem a little this way.” And then you come back and you’re in a conversation with them, where you get them thinking about their patterns.
We have a tool called the “Growth Meeting Guide”. We’ll try to put that in the show notes. If people sign up at Refound, that’s one of the first things you get in your email, is a meeting planner, where you actually get the things that are in your head about your employee. You’re thinking all kinds of things, you’re feeling all kinds of things – get those things out of your head so that you can start to say, “Hey, I noticed that you seem to be really quiet in meetings when some of the other directors are around, and I wondered if you noticed that.”
Pointing out those behaviors where you see people holding themselves back from being their best, and doing it over time. So the best practice is to do it gradually. You don’t pull somebody aside in the middle of the day and try to reboot their entire personality – that doesn’t work. You have to warm people up to the concept, you have to show them a pattern, you have to get them thinking about why this should matter and how it’s going to help them. And then you keep your ears open and listen.

Pete Mockaitis
Powerful, thank you. So, you said that’s one tool within the accountability dial, and it’s really a great one. What are some of the others there?

Jonathan Raymond
There are 4 questions that I often ask managers to ask their employees. So if you pick a behavior, here are the 4 questions. So let’s say that behavior is playing it safe, when it comes to taking creative risks. Let’s say that’s the pattern that you’re observing – someone doesn’t stretch beyond their comfort zone. So ask them this: When they don’t stretch beyond their comfort zone, how does it make their teammates’ job harder or more frustrating? That’s the first question.
Second question: When they don’t stretch beyond their comfort zone, how does it make you do your job as their manager… “How does it make my job harder or more frustrating?”
Third: When you don’t stretch beyond your comfort zone, how does it make the lives of our vendors, our customers, our partners… How does it make their life harder or more frustrating?
And then fourthly: When you don’t stretch beyond your comfort zone, how does it hold you back from becoming the kind of person that you want to become? And those 4 questions – and again, those are in the tool – when you ask those questions, it immediately takes it out of the realm of accusation and shaming and causing people to get defensive, and just inviting them to look at…
‘Cause most of the time you will find – you already know this personally – is that as long as somebody does it kindly, when somebody points out something to you about how you’re behaving in a way that’s impacting others, what’s your first response? It’s, “Oh my God, I had no idea I was doing that. I don’t want to do that, I’ve got to change that.”
Any conscientious person – we might get a little defensive, we might go, “Oh, that’s BS”, we might kick and scream a little bit, but somewhere in there our better angels are going to go, “Wow, that’s not good”, and we’re going to make a change. And so your job, and this tool, these 4 questions, are very effective in flipping the conversation. This is not about me trying to change you; this is about me trying to help you connect how you’re showing up with impacts in a way where you go, “Wow, I can do better than that.”

Pete Mockaitis
Well, those questions sure seem to pack a punch. And I guess I’m curious… You said the good angels; I’ll be the devil’s advocate here then. So I’m wondering if some folks on the receiving end of that could in fact do some lashing out, like, “Why are you guilt tripping me about this?” or, “Geez Jonathan, I’m a grown man, you don’t have to patronize me like this.” So if you get some resistance or backlash, what’s the next step to handle that well?

Jonathan Raymond
One of the skills to develop is to be able to pivot conversations. So sometimes you get people and they say, “Wow, I don’t understand why you’re accusing me of that.” So you can be able to stay in contact in terms of, “Wow, that’s interesting that you’re having such a strong reaction. Do you think that that’s not a fair question? That’s a question that I would ask myself. I mean if you think that’s not a fair question, let’s talk about that.”
So you’ve got to be able to hold your seat. Part of being an authority is not to collapse when somebody gets defensive, because people get defensive to test you and see if you’re going to hold your ground. So if you give some constructive feedback and you’re the boss, whether you’re the manager or the CEO, and somebody comes back with a strong reaction, then you might note that and be like, “Wow, that’s interesting. I don’t think that I said that in an accusatory way. I’m open to hearing if you think that I did.”

Pete Mockaitis
Yeah, that’s good. This kind of reminds me of… I guess the word “grown up” just comes to mind, in terms of, these are powerful questions that can be challenging, and it seems like some folks will love it and embrace it and some will go maybe kicking and screaming. But you said the ratio was pretty darn good, in terms of about 99% of the time, if you’re warming it up gradually, folks roll with it.

Jonathan Raymond
And here’s the thing. Let’s come back to what we talked about at the beginning – the difference between stated values and embodied values. If you have a value of professionalism and responsibility and integrity, and you give somebody… As long as you’ve done it kindly and you build it up and you created some context where they know that this is not attacking, this is you caring about them; and they get defensive and they kick and scream and they go toxic with their teammates – they’re not supposed to be working there.
That’s you embodying your values and saying, “You know what? This is really important, and it’s not just about getting the tasks done in your inbox; that’s not how we evaluate people here. That’s part of it, but part of it is how you show up. And right now with resisting and not being able to hear feedback, that’s not a good team and I’m not going to support you in continuing that behavior.”
So absolutely, it’s about creating a culture of fully functioning adults. And there’s an amazing video that Simon Sinek did, an interview that’s out, and this is our responsibility, and I fully agree with him on this. And it’s not to trash millennials, ’cause there’s a lot of people who are 50 or 60 that do this too, but most organizations, especially organizations that talk about culture do a lot of coddling, they do a lot of looking the other way on non-adult behaviors.
And in my mind if you want to create a great culture and a high-performing team, you should have very little space for non-adult behavior. Maybe once, and then, “Hey, not showing up on time – that’s not okay.” Not every job requires you to be there at a certain time, but if your job requires you to be there at 10:00 am or 6:00 am or whatever it is for your shift, then you’ve got to be there. And we don’t make 5 exceptions to that rule. And there’s a way to be caring and set boundaries at the same time, and there’s not nearly enough of that happening in most progressive cultures.

Pete Mockaitis
Thank you. I’d also like to hear, you used a phrase in your writings about “unpacking unconscious bias”. Can you tell us, what does that mean, why is it important and how do we do it?

Jonathan Raymond
So this unconscious bias, which is of course all over the place these days, and the most common form of unconscious bias is confirmation bias, which neurobiologists will tell us, neuroscience will tell us, and mindful meditators will tell you the same thing – is that we look for information that confirms what we already believe and we filter out information that goes against it or counters it.
We do this out of necessity, it’s human. Doesn’t make you a bad person, doesn’t make you small minded, it doesn’t it make you evil. It’s just what we do, it’s a functional necessity of being a human being. We have to filter out a lot of data.
But when we apply that in the work context and all of a sudden, we don’t know we’re doing it, but we’re treating women differently than we’re treating men, because maybe we have some history that is informing that. But we’re not conscious about that; we just give men a second chance on things that we don’t give women a second chance on. That’s unconscious bias.
Or we look on an employment application and because the name sounds African-American or from an Asian origin, we don’t know we’re doing it, but we might not put that name to the top of the pile. So it happens in the hiring process, but it happens in real time. And there’s ways to look at, but you have to listen, you have to ask questions and to observe the organization and see what’s happening and look for the patterns.
If you work on a team and let’s say you are a white male, and everybody in your team is white male, you’ve got some unconscious bias going on. Are you going to look at that or are you going to pretend it’s not there? If you look at leadership teams, it’s changing, but it’s not changing fast enough. Most leadership teams, especially in tech, it’s a lot of white men. That’s a problem for women trying to make their way in the organization, because they don’t have a lot of role models for how do you inhabit authority as a woman.
And so it’s so complex, and you don’t have to solve it but you have to ask the questions, if you want to create the kind of culture that feels inclusive and not just diverse on the surface, but intellectually diverse. Those are the kind of places people want to work.

Pete Mockaitis
Thank you. So we talked a number of times here about the honest, hard or challenging questions and feedback offering. I guess I’m wondering – we talk about being an adult – what are some best practices or behaviors when it comes to being on the receiving end of that feedback and getting it, first of all, if it’s hard to come by, and then using it well?

Jonathan Raymond
The most difficult thing, I think, to do as an employee is to separate the message from the messenger. It’s very hard when you have a boss that you don’t like or you don’t respect or you think that they’re hypocritical one way or another. It’s very difficult to do, but the most important thing to do is to separate the message from the messenger.
Let’s assume you’re right – they are hypocritical, you don’t like them, they’re not a great person to work for, they don’t walk their talk. And what is true about the piece of feedback that you just got, or the review? What can you take for yourself and say, “You know what? I don’t like the way they said it, I don’t like the way they delivered it, and I think that they should’ve done it differently. But for my own self development, I’m going to take a 100% ownership of the truth that’s inside of that feedback.”
It’s the most difficult thing to do. It’s so easy to just throw the thing aside because of the way it was delivered. That’s the highest bar of self-responsibility that I know is to do that, is to say, “Look, I don’t like the way it got to me, but it’s here and I’m going to do something with it.”

Pete Mockaitis
Okay, thank you. And any final perspective on what should be happening or done in order to have great one-on-one meetings?

Jonathan Raymond
Let’s start with the employee side. This was always my dream, and I was able to achieve this after a while, as I started working this way, is I want employees to start thinking about, “How can I own the one-on-one?” So if let’s say you have a weekly one-on-one, don’t wait for your manager to initiate the conversation. Come prepared. What do you want to work on?

There’s something you want to get better at. Be proactive. Go into that meeting and say, “Hey, before we talk about anything else, there’s something that I want to work on and I would like your help with. Can we talk about that?” That’s a manger’s dream, that’s a CEO’s dream, is when you want to distinguish yourself and set yourself apart from the crowd.
Be proactive about your own growth and make your one-on-ones about you. And, “Here’s what I want to work on, here’s my goal for this year and here’s how I see it relating to my job.” And if you want help developing that, send me an e-mail – hello@refound.com, and I’ll help you develop that conversation.

Pete Mockaitis
That sounds ideal, thank you. Well, Jonathan, tell me – is there anything else you want to make sure we highlight before we shift gears and hear about some of your favorite things?

Jonathan Raymond
I would just say just because we ended up talking a lot about difficult feedback and awkward conversations, I can’t emphasize enough – the purpose of a recurring one-on-one meeting is that you have a positive frame, you have a positive conversation that’s happening on a regular basis, where you’re recognizing all the good things that this person is doing, so that when you have to have an awkward conversation or a tough conversation, there’s a context; it’s not coming out of the blue. So we spent a lot of time talking about the tactics of how to pivot that conversation, but if you try to do that without having that weekly one-on-one conversation where that person already feels like you’re on their side, it’s not going to go well. So remember to keep it in balance.

Pete Mockaitis
Thank you. Okay, well then could you start us off by sharing a favorite quote, something you find inspiring?

Jonathan Raymond
The quote that I put at the front of the book is one that I live by, which is: “We teach best what we most need to learn.” And I think that that’s true in so many different ways. It was from Jonathan Livingston Seagull, I think is where that actually comes from, an old book. But we teach best what we most need to learn, and so whatever that is that you’re teaching, a good thing to look at is, “How do I need to get better at that? What am I trying to teach myself in that process?”

Pete Mockaitis
And how about a favorite book, or something that you’ve turned to again and again?

Jonathan Raymond
Let’s see, what’s my favorite. I like to read comedy and different things, and so I would say these days we read a book with our family called Three Bags Full, which is a sheep detective story. And I think it’s great to get out of the work mode and into a more playful state of mind, and especially if you have kids and you like reading books out loud. Three Bags Full is a great one.

Pete Mockaitis
Thank you. And how about a favorite tool, whether that’s a product or service or app or thought framework you find yourself turning to again and again?

Jonathan Raymond
There’s a couple of tools that I use that I really like. I’m a big fan of Drip, that I use for my email service. It’s a really simple tool to use. And I really like, the HubSpot has a free CRM. Their marketing tools can be very expensive, but they have a great sales tool that you can use if you’re in the sales world, that’s a really nice kind of visual flow interface, and I really like that tool.

Pete Mockaitis
Thank you. And how about a favorite habit, a personal practice of yours that helps you be more awesome at your job?

Jonathan Raymond
Walking. Get up from your desk, wherever your desk is. I have a raisable desk and I feel fortunate to be able to stand when I work sometimes. But the best thing that I do is to get up from my desk and go outside and don’t bring my phone and just go for a walk. Even if it’s 10 minutes, 15 minutes, whatever it is – go for a walk, give yourself some space to be with your own thoughts, without distraction a couple times throughout the day. You’ll be far more productive when you do get back to your desk.

Pete Mockaitis
Okay. And how about a favorite sort of nugget or quote or Jonathan original that tends to get folks nodding their heads, taking notes, re-tweeting, Kindle book highlighting, kind of really connecting with an articulation of your message?

Jonathan Raymond
The thing that people are often resonating with is this idea that personal and professional growth are one thing, not two.

Pete Mockaitis
Okay. And how about the best way to contact you or get in touch if folks want to learn more and see what you’re up to?

Jonathan Raymond
So we’ve got a host of free stuff at Refound.com. And people can reach out to me, hello@refound.com. And if you mention that you heard this podcast I will send you a 10% coupon for any of the programs, if you want to enroll in one of our training programs.

Pete Mockaitis
Excellent, thank you. And do you have a final challenge or a call to action you’d issue forth to those seeking to be more awesome at their jobs?

Jonathan Raymond
Yes. Here’s the challenge: There’s one conversation – there’s probably more than one – but there’s one conversation that you’re thinking of having right now, that if you don’t take an action you’re going to wait until tomorrow and then you’re probably going to let it go. So my challenge to you today is, don’t do that. Have that conversation, find that 5 minutes, pull that somebody aside. Do it kindly, do it compassionately, but tell them, find a way to share what’s been on your mind and open up a new conversation, instead of waiting till tomorrow.

Pete Mockaitis
Alright, thank you. Jonathan, this is so good and juicy. I want to be chewing on this, and thinking about some of those conversations in my own world. And thanks for everything!

Jonathan Raymond
Yeah, you bet. Thanks so much for having me on, and great questions!