091: The Path to Truly Productive Leadership with Michael Dolan

Pete Mockaitis
Michael thanks so much for joining us here on the How to Be Awesome at Your Job Podcast.

Michael P. Dolan
Good to be here, I’m excited to have this conversation.

Pete Mockaitis
I am too and it’s so fun. So I see that you were working at the David Allen Company and David Allen was so awesome as to have a chat with us back in episode fifteen and more than once I’ve had friends just bump into job postings from the David Allen Company and send to me like ‘hey this sounds like you would love this kind of thing’. So I would love to hear about your experience. What are some things you’ve learned from working in that industry and from David himself and that whole experience?

Michael P. Dolan
Well, I started working there about eleven years ago. It was my first role as a coach and before that I’ve been working in a combination of things like brand management and advertising and a little bit at a design firm. I ended up coming across David Allen and his work because way back when I was a brand manager at the Clorox company working on Glad plastic wrap, believe it or not. I had a review one year that didn’t go so well, it was okay but the worst little check box was an area called planning and organizing on my review. So I needed help and my boss said ‘hey why don’t you go find somebody to help you get better at that and it turned out that David Allen was doing seminars and trainings at Clorox. I met him there and then I ended up getting coached by Kathryn Allen – his wife and Co-CEO and several years later after a little bit of career wandering and soul searching I realized that coaching was the right thing to do for me and more of why I was here in the world.
And I loved working for David at the company, I was there for about five or six years. For me it was the first time in my working life that I felt like I was just completely being me and doing what was natural as opposed to playing a role or making things up or posing as somebody I wasn’t. So that was a huge relief for me and David himself I have an immense amount of respect for. I think he’s a pretty amazing man. Some key things I’ve learned from him there, the first as you might guess from knowing about Getting Things Done his approach is just his sense of integrity. This is definitely a man who walks his talk and follows through on his commitments and is honest when he can’t and I learned a lot about that from him.
Another thing a little bit deeper that still I think has a big impact on me that I learned from working there and working for him is David is someone with a very deep sense of spiritual purpose, a very deep spiritual practice and you wouldn’t necessarily hear that because he doesn’t necessarily talk about that directly.
But to learn and see someone like David who has that deep spiritual commitment inside of his life and to see that there’s a way to express that commitment through seemingly non-spiritual work in the world. As a coach now I do some work around work for coaching a lot of what I learnt from David but a lot of my work, it sounds similar to you, is around general leadership development and one on one coaching and as a coach I personally also have a pretty deep spiritual practice and community. I have a deep sense of why I’m here on the planet and what’s important and it’s not that I necessarily bring that conversation up every time I’m talking to an HR Director who’s considering hiring me for coaching but to know that the working I’m doing that might be very kind of block and tackle skills based. It’s still about helping other human beings, being more fully expressed on the planet and also helping myself get out of my own way to do the same. So David was definitely an inspiration regarding that.

Pete Mockaitis
That’s fun. I was so glad to hear and that’s just a great description like a job in which you feel totally natural and you as opposed to contorting yourself and fitting into some sort of set of expectations which is not so natural. That is cool, thank you.

Michael P. Dolan
And I have to say only in hindsight could I really see how much, I wouldn’t necessarily say authentic, how not really me I had been in those previous roles. It’s kind of like once you go to the optometrist and you put on that new pair of glasses and you can actually see and only then can you really see how blind you were.

Pete Mockaitis
So the name of your practice currently is Truly Productive Leadership, what does that phrase mean to you?

Michael. P. Dolan
Well I was going about the task of heading towards hanging my own shingle and saying this is who I am and what I offer I chose that name for my practice intentionally.
Specifically the word truly, truly productive because I see my work whether I’m working with leaders around work for coaching all GTD type stuff or around deeper leadership development.
I see my work as not about necessarily having somebody be faster or better at completing and accomplishing more things in a materialistic sense. If I’m working with a client and they’re, if I’m doing my job well and they’re engaging in the coaching at a deeper level what it ends up looking like is they end up making their choices about what they engage in, in a way that is completely aligned with who they really are at a deeper level and what really matters to them.
So sometimes being truly productive may mean realizing and confronting yourself that you are not in the right role, you’re not at the right company or you’re not aligned with your vision or your sense of purpose about who you really are and it’s time for some difficult conversations and some change. Sometimes being truly productive looks like not doing anything at all because you realize you need stillness, you need space, you need a break.
My intention with what I do and with the name that I chose is really about talking about how does it look to be a full human being who happens to work with other human beings to get stuff done in a world and what does it mean to be truly productive.

Pete Mockaitis
Well I’m intrigued and it sounds like it can take a number of expressions and forms so do you have these are the principles or tenets of a truly productive leader or are they kind of more open ended than that?

Michael P. Dolan
Well I do tend to look at three core areas, I guess this is what tends to show up when I’m working with most of my clients and those areas are what I call Self Management, Self Awareness and Purpose. Self Management not in the psychological sense which typically is used to mean being able to manage our reactivity and emotional responses. That’s also very important but when I say Self Management it’s really about do I have a way to manage all the agreements I have with myself and others in a way that I feel that I’m integrity and I’m doing what I say I’ll do and getting done what I intend to get done.
You know I’m not spinning and reacting to the latest and loudest all the time so that’s Self Management. With many of my clients I do that kind of work, not all sometimes they already have a really clear, clean way of doing that and that’s not the issue we focus on.
Self Awareness the second bucket of type of work. A huge part of any coach’s role hopefully is about helping clients. I always use the image of like I was standing with them with a flashlight pointing in some dark corners and saying why don’t you look over there in terms of your own experience when this kind of pattern happens and you learn for yourself what’s driving this pattern. What’s really going under the surface? What do you not yet know about yourself that if you were open to discovering it could have you feel and be more free about how you respond to the world, how you express yourself, how you show up as a leader or how you show up as a dad etc.
So I do various different things with clients to help them with Self Awareness, it partly is what happens in the alchemy of the coaching conversations but also I’m a fan of a personality tool called the Enneagram which I haven’t found anything more impactful and powerful in terms of being a mirror of Self Awareness and an ongoing invitation to self observation and catching the machine of our personality in the act and therefore becoming more free from it over time. So Self Awareness is a big part of my work and lastly Purpose. Often when the other two buckets are getting some movement and getting some freedom there naturally is some question and some conversation about what really matters and why am I here? Why am I in this role? Why am I on this planet? What really matters to me in whatever level that makes sense? So when my conversations end up there to some extent so when all three of those things are being chewed on there tends to be growth and development.

Pete Mockaitis
Thank you, so that’s a helpful kind of categorization to work with, with those three different areas. So I’m curious maybe within those or even if they don’t fit cleanly underneath the categories. What are some of the practices that you find yourself challenging folks toward repeatedly when you’re helping them out and I saw a great quote from your website that you’re helping folks “achieve a sustainable sense of balance and productivity and improved effectiveness as a leader.” That sounds fantastic so what are some of the key hows or assignments that tend to show up a lot as you’re doing this.

Michael P. Dolan
Well it’s always different for every client. I don’t tend to have a cookie cutter approach so every human being is going to be coming forth with a different development opportunity in themselves and part of the work is about helping to understand and explore what is that opportunity. In terms of practices often apart of that is helping somebody get feedback about themselves to look in the mirror so to speak through the eyes of everyone around them. That tends to be an important part of that initial Self Awareness because a lot of us want to know what they have feedback about ourselves but it can be pretty difficult to actually really take it in and not have our defenses come up and our fear get in the way of seeing something new about ourselves.
Often feedback is a big part of you can say practices. If I’m working with somebody on what I call Self Management really GTD practices the way David articulated them in Getting Things Done are a big part of how I do that with folks. So helping step by step, get somebody up and running with that approach. Re-emptying their head, going through all of their emails, going through all the stuff they have attention on and learning to keep it out of their head and decide about it sooner rather than later, keep it organized in a clean updated system and use all of that, all of those practices to help them make better choices about how they’re engaging, so GTD practices are often a baseline. Sometimes what I found and what seemed to have emerged is my unique positioning as a coach is that often leaders at a higher level are being called forth to really develop deeply as human beings, as leaders.
And sometimes one of the key gating factors that’s getting in the way of their development is that they are having a hard time just keeping up with the volume of stuff and the volume of changes and delegations and email and meetings in a way that still allows them to have space for reflecting and thinking and doing the self observation, Self Awareness work that a leader needs to do. So sometimes what I find myself doing is getting a client up and running with the basic GTD practices, kind of clearing the decks so that they can have more space. More sense of peace of mind and control so that we can have the deeper conversations, so they can do the reflection and the journaling sometimes about what’s showing up in their experience, what feedback they’re getting etc. So some other key practices I tend to, not always it depends on the client but I see some form of a meditation practice or mindfulness practice as I always call it the fertilizer of Self Awareness. It’s a pathway to giving in my experience giving some breathing room for us to have curiosity and humility about our own behaviors and thought patterns etc. and when we get more onto that stuff and more real about what’s really happening in ourselves it gives space for virtue to arise. Different virtues like humility or compassion or sobriety or things like that.

Pete Mockaitis
I think that’s very well said and I could see this in myself as well as others. That connection between whether you’re just sprinting to keep up with the volume and if you are you’re often less generous I guess with your time I guess. It’s like I don’t have any time, it’s scarce I need every minute I can to not die – that kind of feeling and as well as just having that space for as you said self reflection and such. So I know that it varies on a client by client basis but can you share in terms of when it comes to getting that space ahead of the emails and meetings and the non-stop latest and loudest there are the Getting Things Done practices associated with getting things out of your mind and into the system is key but are there additional things that need to happen in terms of the actual re-negotiation of commitments. Like how does that happen in practice?
It’s like I’m thinking some folks have to be told no and some meeting need to disappear and some emails need to be handled by others, in terms of the tasks that they carry with them. So what are some of your best practice perspectives when you’ve got things out of your head and into a system and now it’s time to reduce the commitment load?

Michael P. Dolan
Well, differently for everyone. No cookie cutter as we both agreed. What you’re asking about really gets down to what happens in me as a human being when I need to make a request, when I need to say no, when I need to declare something that’s true for me despite however you might react, what I need to re-negotiate something. We all have different ways that we get in our own way when we’re interacting with other human beings about all of that kind of stuff. You know the book that comes to mind that I’ve enjoyed, a really simple book that I’ve passed onto clients who are maybe working on saying no is a book by William Ury called The Power of The Positive No.
He was part of the Harvard Negotiation Project, he wrote some books on negotiating. It’s I think his latest book or if not it’s one of the later books from him and in your question inherently there is in any kind of re-negotiation of commitment there is a no that has to happen either to our self or to another person. What he talks about in that book is we all have our different patterns and different shenanigans that go on inside of us when we have to say no and what he offers as a practice and a solution is to become more and more conscious in those moments of what am I saying yes to in this moment instead of this thing that I’m saying no to. For instance my son really wants to go play on that piece of equipment at the park that I see as a little bit sketchy and he really, really wants to and then part of me, the old nice parent who wants to be the buddy wants to say yes but I say you know Maxwell I care so much about your safety that I don’t think that’s a good idea. No can’t do that.
And the same thing happens when we have leaders who have A Type personalities who want to get it all done and who are used to accomplishing and feeling valuable through accomplishing and who have lots and lots and lots on their own lists and the first step often is being able to say no to themselves. To look at those things on their project list and have the awareness to feel wow, I am over my capacity, I have up until midnight for five nights in a row or a month in a row, I need something so I can have more balance and space. So in those cases it’s a I’m saying yes to my own health and balance and for me to be able to do the other stuff that is really important excellently and in order to do that I’ve got to say no to these things and it might be difficult conversations but it’s a no to myself first and then let me go have that conversation with Bob down the hall.
So that’s one simple little framework from that book that I think is a helpful kind of inquiry for all of us because we all I think and I experience it myself and I see it in lots of clients is we all different things that come up around saying no. Some people say no way too easily and then they’re left with not a lot of friends and they’re seen as jerks, seen as not cooperative and they’ve got to look at the other side of that coin.

Pete Mockaitis
I would love to get your take, if you’re thinking about people’s lives who sit up to midnight on many, many days in a row. I’ve been noodling on this and exploring a bit about an optimal amount of time to work and just how much good thinking the knowledge worker can actually do in the course of a day and a week. I feel like you’re going to tell me it varies but I would love to get your take in terms of what do you think is our capacity for thinking and knowledge work before we’re suffering. Maybe we don’t even know it but the quality of what we’re producing and delivering is suffering because we’re working too darn much. Would you hazard a number or a range of numbers of hours in a week?

Michael P. Dolan
You know it reminds me of an article I saw recently of a guy in San Diego that has a company that is growing like gang busters and their company it sells water sports equipment like paddle boards, upright paddle boards and he… I think it’s a medium sized company I think it’s at least over a hundred people and they have experimented and he as a leader has made the declaration and created this culture where they only have five hour work days.
Because they have this culture of…

Pete Mockaitis
Well the surf’s up bro

Michael P. Dolan
Exactly, you got to get out there on the water so they work from 8 o’clock to 1 o’clock or whatever the math is there and they have the freedom to go out and have their life. The point that he was making which I agree with is that if you look at the average workday, if somebody is working ten hours in a day the total amount of time that they’re actually really fully engaged, focused, creative, there working hard, creating an output tends to be a small percentage of that. I guess half of the time, maybe less than half of the time is actually super productive. I think about the syndrome that I’ve seen with a lot of clients of mine who are working new mothers and I saw this with my own partner with the mandated change in their availability and their time.
The focus during the working hours on getting stuff really done in a much more limited amount of time just increases and that alone has shown me the truth in the fact that I guess what I’m saying we all tend to doodle our fingers and twiddle our thumbs here and there during the workday because I think it’s there’s natural rhythms as a human being that you can only engage fully for so long before you need a break and a rest and a change of scene. So I don’t know, four hours, five hours a day of actual productive work?

Pete Mockaitis
I think I buy it especially if there’s a meeting, does it really need much input from you? You can kind of coast it’s like ‘I’m just being informed, alright that’s fine’ or sometimes when it comes to emails it’s like ‘alright we’ll delete, delete, delete’. It doesn’t really require a high level of energy and attention.

Michael P. Dolan
Right, I’m going to go over to Facebook here or I’m going to check things out. I felt like in my own personal experience if I have a day where I have more than four or five hours of actual one on one coaching time which is my version of I’m doing my work to the highest level that I can possibly do it.
If I go beyond four hours of that per day I feel like this is pushing it. Lots of the things that I have to do during the day but I just think about that kind of frame, yeah about four hours of that is about as much as I probably should schedule for the sake of my clients to get the best of me. But good question, I think one thing is for sure from my perspective is that we are all in a slippery slope of working longer and harder and later and not necessarily experiencing the impact of that and it’s leading to a lot of burnout and a lot of stress and disease and broken families and it takes courage to see it and change something about it.

Pete Mockaitis
Beautiful, thank you. So now this has been a fun flavor of conversation in terms of very thoughtful and the kind of principles and the conceptual pieces so I would love it if we could also hear do you have some favorite tips and tricks and tactics when it comes to when people do this they really see an upgrade in their workflow process or their collaboration.

Michael. P. Dolan
Yeah I go right back to what David articulated in Getting Things Done because I think he really boiled it down to the truth of human beings and human being who have more to do than time to do it in and what needs to happen to alleviate that. The basics are stop keeping anything in your head about any open loops of stuff you’ve got your attention on. Decide what it means to you sooner rather than later. Park the results of that thinking in a place outside of your head that you can trust and keep current and review easily and review and refresh that system regularly because it ain’t going to clean itself up and then trust that all that great work that you keep on doing to feed that external system.
Trust those lists and that calendar when you want to know what should I do right now. Nothing’s new about that and David did a great job of articulating the truth of that. There’s some folks out there who say ‘well you know David’s Getting Things Done approach doesn’t make sense anymore because we’re in a modern world’ and I have to call bullshit on that because the fundamental nature of what he said will never change if human beings always have more to do than time to do it in.
Who knows, maybe our brains will evolve so that we can actually use our heads to manage all that stuff or there will be some kind of artificial intelligence system around us keeping track of all of our commitments for us but until that happens, these phases of workflow really work. Today I think one of the things that I see out there like I said, I think I sound like a little bit of a curmudgeon I hope not but I do see especially like when I’m going into the San Francisco younger tech companies. What I see that I think is a dangerous trap for people to watch out for not falling into is in the effort of really being fast and nimble and moving fast with the business, people themselves are moving a bit too fast and leaving piles of open loops behind them. It may have moved something forward a little bit by pressing forward and a few words in an email but if there’s still an open loop in your head about that thing and multiply that by about a hundred things. It’s just going to hurt over time, it’s just going to slow you down, balls are going to get dropped, there’s going to be conflicts, work won’t be coordinated well. So in general the dictum of learn to slow down just a little bit while you’re making sense of something so you can speed up later I think is really important these days.

Pete Mockaitis
Okay well now if it works for you I would love to shift gears and hear about some of your favorite things.

Michael P. Dolan
I hope I can give some cool answers for your listeners.

Pete Mockaitis
Alright, I think you can indeed, we’ll see. Can you share with us a favorite quote?

Michael P. Dolan
A quote from an old boss of mine in a design firm, he said if you aim at nothing you’ll hit it.

Pete Mockaitis
Thank you, how about a favorite study or piece of research?

Michael P. Dolan
I thought you might ask this question and it’s not necessarily a piece of study but it’s a framework that comes out of two academics at Harvard Bob Kegan and Lisa Lahey. It’s a framework called the Immunity to Change model, it’s a really powerful, step by step approach to helping our self or someone else understand what’s getting in the way of a change they’re trying to make and keep on failing at.

Pete Mockaitis
Can you tell us a little bit about it?

Michael P. Dolan
Yes, well it’s great. It’s a process where you have this four column piece of paper and you start on the left side of the piece of paper with what is the behavior change that you’re trying to make but you’re having a hard time changing. You know, just name that. Next column is what behaviors am I doing or not doing that in doing or not doing them is getting in the way of that behavior that we want to happen. So what are we actually doing or not doing. Does that make sense?

Pete Mockaitis
Yes.

Michael. P. Dolan
The next column is what is our biggest fear or worry if we actually did the behavior we’re trying to change like if you imagine yourself doing the opposite of all those things that you’re doing in the way. Verbally in a five second description it might be a little confusing because there’s a lot of flip flopping of meaning that goes on through the columns but eventually in the fourth column what is revealed is the underlying, deeper, big assumption that is driving this one foot on the gas, one foot on the brake that happens in us when we all experience things where we really, really consciously want to change something but when we look at our actual behavior we’re not. Something different is happening and so it’s a process that helps you get that at least a good theory about what are the big assumptions that are making usually that have to do with fear. Fear of not wanting to be seen as x, y or z. Fear of not showing up as our idealized image of our self, that kind of stuff and then once we see that we can start testing it in the world. We can start making experiments with our behavior and seeing okay did that big assumption actually play out or was I wrong? So we can slowly loosen out big assumptions and have more freedom to make that change.

Pete Mockaitis
Interesting.

Michael P. Dolan
Immunity to Change is what it’s called, ITC.

Pete Mockaitis
And how about a favorite book?

Michael. P. Dolan
A book lately that I’ve been liking and recommending a lot is a book called The Fifteen Commitments of Conscious Leadership by Diana Chapman and Jim Dethmer. I really like their bold approach at really going for it in terms of if we’re talking about really wanting to be conscious human beings who get stuff done in businesses.
This book goes through unapologetically what does that really look like, things like I’m 100% responsible for my relationships. I fully feel all my emotions through to the end so I can get the value from them and respond in life more fully. I have integrity to my word, things like that and there’s fifteen of them. I can’t name them all but I really enjoyed that book lately.

Pete Mockaitis
And how about a favorite tool?

Michael P. Dolan
Well from the productivity side of things I’m a big omni focus fan.

Pete Mockaitis
Oh me too.

Michael P. Dolan
Mac user and omni focus is like it was the killer app that had me most excited about changing to the Mac two years ago. And lately I also like many people I think in the last year or two have gotten onto the online scheduling bandwagon but it really has changed a lot for me because if you could imagine some of my clients tend to be a little bit out of control when they need my help. So they need help being more in control so when I’m trying to schedule things with them often I had for five different potential clients I had three different slots offered to each of them and I was holding them on my calendar so my calendar was always screwy and I really love, there’s so many different options to online scheduling but that way I just send them a link and they pick one that works and bam it’s scheduled. And that’s changed a lot for me without me having to hire an assistant.

Pete Mockaitis
That’s great and I just shifted from ScheduleOnce to Calendly myself. What are you using?

Michael. P. Dolan
I’m still on ScheduleOnce, it’s still working for me. I’ve given my technology ecosystem to fit my needs but Calendly is probably the second one that I’ve heard of and have heard great things about.

Pete Mockaitis
ScheduleOnce, it is a reliable workhorse. I just wanted to customize some of my things and then I had to super upgrade in order to do that so I go ‘I don’t want to do that’ so we parted ways. How about a favorite habit or personal practice of yours?

Michael P. Dolan
This is a bit personal but I’m a transparent guy, one thing that I’ve been doing over the last month. I was on retreat a couple months ago and really became aware of some early patterns that I had in terms of my relationship with my father and I guess putting it in a nutshell saw how closed I had always been to receiving his love. So a practice that I’m doing everyday is kind of a meditative/ imagination exercise, he’s been dead for six years but I’m just remembering him and opening myself up to the experience of him loving me and it’s really had a big impact on me in terms of the old equation of am I in touch with loving myself.
And I realized how that piece of my parental upbringing and the influences on my psyche was missing and I’m feeling strong because I’m letting this side in. That’s one thing I’m doing as a habit.

Pete Mockaitis
Good news and could you share perhaps also a favorite resonant nugget? Something you share that really seems to hit people and impact them?

Michael P. Dolan
Well I think it’s a quote I actually have it on the homepage of my website at trulyproductive.com and that is leadership is about bringing your whole self to the table. When you fully show up others are naturally invited to do the same.

Pete Mockaitis
Okay and what would you say the best way is to contact you or get in touch?

Michael P. Dolan
Listeners can email me directly, Michael@trulyproductive.com. Check out that website – trulyproductive.com, Facebook page you can search Truly Productive. Those should all work.

Pete Mockaitis
Thank you and would you say there’s a final challenge or parting call to action that you would issue to those seeking to be more awesome at their jobs?

Michael P. Dolan
My take is that development as a human being should never stop and we all sometimes get caught in patterns in our life where we unconsciously have given up on some aspect of our own development.
So I think the challenge would be where might you have given up? Where have you stopped believing that there’s more to be learned? Is it a certain relationship at work? Is it a personal relationship where you’ve given up on it being a different? Is it a personality pattern in yourself that you feel that there’s nothing else to see about?  Someway that you’re seeing yourself or the world that you might be stuck in? That’s my challenge – where have you given up where you might open up to deeper question and inquiry?

Pete Mockaitis
Thank you.

Michael P. Dolan
You can tell I’d like to go deep.

Pete Mockaitis
Yeah that’s good. I’ve got to chew on every one of these for a little bit here.

Michael P. Dolan
That’s what you get with Michael Dolan.

Pete Mockaitis
Well Michael it’s been a lot of fun and really appreciate it and I wish you all the best and with your Truly Productive Leadership and all you’re up to.

Michael P. Dolan
Thank you so  much for your fun interview and your curiosity  and I really enjoy listening to your other interviews as well so had fun.