Reflecting on The Leadership Journey

7 Powerful Tips for Getting Things Done

Tom O’Brien,  Vice President of Human Resources at Trinchero Family Estates

Reflecting on The Leadership Journey: 7 Powerful Tips for Getting Things Done with Tom O'Brien, Vice President of Human Resources at Trinchero Family Estates

On this episode of the Menttium Matters Podcast, Menttium’s Megan Cummings-Krueger sat down with 15-time Menttium Mentor, Tom O’Brien, for an authentic and insightful conversation about life-changing events, how they alter our perspective, and how to open ourselves up to what is possible. He also shares how his own personal and professional experiences led him to find his passion for mentoring.


Cummings-Krueger: Welcome everyone to the Menttium Matters podcast, where we talk about leadership, life, and the transformative power of mentoring. I’m Megan Cummings-Krueger, and today our conversation is going to look at the duality of change, sudden change. And, that change also, including that is not our choice, but was thrust upon us, can be extremely challenging. I think everyone listening to this podcast can certainly relate to that to some degree. While change can be difficult to endure and can be overwhelming in the moment, it can also result in dramatically shifting our perspective and be a source of that hard won wisdom that we’re always talking about here at Menttium.


My guest today is Thomas O’Brien, who is the Vice President of Human Resources at Trinchero Family Estates. Before we begin our conversation, I want to first give you some background information on Tom. Tom began his career with Nestle prior to accepting after 10 years the role of human resources leader Latin America for Clorox.


While in this role, he was responsible for creating the strategy and direction for forty HR professionals in ten countries. Then following other roles of increasing title and scope at several companies, Tom then joined Trinchero Family Estates in 2011. From his diverse experiences with organizations, industries, and cultures, he really brings a unique combination of business acumen and broad HR knowledge and perspective to the conversation today.


Lastly, I do want to share that Tom received his bachelor’s in business management from the University of Illinois. However, he and his wife now reside in the warmer environments of California. He’s a longtime partner with Menttium. He’s served several times as what we call our voices of experience for various Menttium educational sessions and as a mentor, he is currently supporting his 15th mentee. So welcome, Tom.


O’Brien: Thank you, Megan. It’s great to be with you today for sure.


Cummings-Krueger: My first question for you Tom is over the years, as I mentioned, you’ve been on several Menttium panels, and the overarching theme is usually dealing with sudden change. Now in your case, you endured the sudden loss of your first wife early in your career, and of course it had an immediate impact on you both personally and professionally as well as your worldview moving forward. What did you learn as you navigated through this difficult challenge?


O’Brien: I’ve been reflecting on this for quite a while as I was just thinking about it, and as you’d expect it had a profound effect in terms of how you really think about things and what things are important and the priorities you choose when you’re going through the maelstrom of that kind of change. I always like to think about it now after 25 years. The key thing is life comes around again if you let it. I think that’s the key. Sometimes you must slow down to be ready for what might come. I found a quote some years ago that encapsulated it, and it’s by a gentleman by the name of Joseph Campbell. He said, “we must let go of the life that we had planned so as to accept the one that’s waiting for us”. I think that really encapsulates that whole time and the time that’s been since. If I think about that time in my life and the time since, there’s really no certainty of any sort in life. The quicker we understand that the better off we are.


When I say, how did you navigate through it? For me it wasn’t easy. The underlying message for me is don’t try to go it alone. You must seek out the help that you can find and not turn your back on anything that’s possible in terms of what you can do. It is friends, it is family, it is professional help, which both myself and my daughter went to see a psychologist at the time to help me work through some things and she did play therapy that was beneficial for her. It’s important to lean on your network.


Of course, I would be remiss if I didn’t talk about the classic fails at the time. All those things I just said, I didn’t necessarily do them all. And that’s the beauty of hindsight. My daughter and I moved to Florida because of this situation. In my head, I felt I needed to get away from this and change this situation. I wanted all the memories and all the plans we had and things like that. The company that I was working with at the time said, hey, we’ve got this job in Florida and it’s managing our international business. And I said, I’ll take it. When we got there, I’ve got no network, I’ve got no friends, I’ve got no nothing. It was like what were you thinking?


So, the idea is who are those, that board of directors, if you want to think about it, that you can talk to and bounce things off and those people who will give you that sound advice. I guess the one thing that I keep coming back to is always thinking about running to something, as opposed to running from something. I think Florida is a great example of this, even though it worked out in the end, it was an example of I was running from something not to it. It seemed like the right thing in the end when I thought of my daughter and me and things like that.


Cummings-Krueger: I love that reframe. I think that’s powerful. It reminds me of when my girls were playing soccer and they said the goalkeeper was, if you’re looking at them and worried about them, every shot’s going to go right at that. The challenge, the hurdle for you, you must look at the possibilities and running towards it versus running away. I think that’s such a powerful reframe.


O’Brien: It’s something I’ve kept with me close. It’s applicable to many circumstances. When I’m with people, anyone really, when we start talking about change in life, it’s always trying to think about what your “to” is as opposed to the “from”. It does help people think about it and I know it helped me and it still does to this day. There’s always this push pull.


I think the other thing that came out of losing my first wife was I became painfully aware of certain kinds of inequities in life. For example, as a single parent who was a man versus a single parent who was a woman, somehow through that process, I became some kind of saint as if taking care of your family and raising your children was something that men don’t do. I was treated like a deity almost. I just can’t understand this because my cohort on the other side of the gender ridge were never treated like that. It was expected that that would happen. People would say, I’m so surprised that you’re doing this, and this is great that you’re doing this. I’d always be looking at them going, what are you talking about? This makes no sense. I signed up for this. This is how it works for raising your kids and your family and I’ve got all the foibles you’ve got, probably more. But we’re going to keep slogging through and the good news is, 25 years on, she’s a very well-adjusted young woman who is now managing her own life. It’s a beautiful situation to see her navigating through her own set of issues and circumstances.


Cummings-Krueger: When we were talking earlier, I really appreciated you brought up that interesting perspective of the dad babysits and the mom parents and inequities of being a solo parent as a dad. I really appreciated that you had that perspective. It had me thinking, oftentimes when we go through sudden change tragedy, it can increase our empathy because we’re so appreciative of all, as you say, leaning on our network.


O’Brien: There’s so many things that if you’re open to it, you’re going to get something from it. I think that the earlier version of me was more, this is the direction I’m going, and this is the way it needs to work, and so on and so forth. It wasn’t always accepting of the alternative. If I think of my whole relationship with Menttium, it really is about an awakening of your mind. If you’re open to possibilities, there’s a lot there for you.


It really did help me find balance in my life. I was way out of balance. When I think of the earlier version of me, I was really focused on my career and Reggie, my wife, was also the same way. We were both very much the same and we needed to think differently. Some other things that I learned is there were so many great people that I’ve had the honor to work with, and there were so many wonderful ideas that sprang from those partnerships that helped me and hopefully them as well become better versions of themselves.


As you say, you just become more in tune as a listener and a questioner, and you see a lot of parallels between people. We’re all on the same road at the end of the day, and you need to stay in the moment if you can. When I think about the partnerships and mentees I’ve had, staying in that moment when we’re in that conversation, and that circle of trust that we’re trying to build the connection, that has had a big impact on me.


Then there’s all the things that I’ve learned tool wise. If I think about Menttium and the value that they bring, the idea of my personal brand and how I’m able to share that with others and what that looks like. I call it my 7 P’s plus one. And then there’s really getting connected with life through like the wheel of life tool. How do you find balance in that way? The ultimate gift was the negative self-talk that we all have. It’s get out of your head; this is going to be okay. The true introvert in me is like, hurry up and slow down.


Cummings-Krueger: You and all our mentors mentor wherever they are; you have the mentoring mentality. But in addition to all of that, you have mentored 15 Menttium mentees. These, of course, are all mentees outside of your own organization, and it’s a yearlong partnership. When you think you have been open, and I hear this so often from mentors, how they feel they learned as much as the mentee did. Can you call up any stories or anything that comes to mind? Maybe something that surprised you or a learning that you appreciated and took from a partnership?


O’Brien: There’s so many different folks who taught me something. If I think of my latest mentee, a wonderful young woman who through the arc of our relationship, decided to change the role that she was in. Now, we’ve switched from, we were working on this thing that had to do with her present job and her present circumstance to this whole new thing that’s having to do with her future and what does this all look like. It’s an interesting juxtaposition between how we started this relationship, to how we are now. It’s all now about the future strategy that we’re working our way through.


I get to be the sounding board for a lot of her ideas and all those ideas are stoking my fire. It has me saying, I should think about doing that. If I go back, there’s always this circumstance, pretty much every person I’ve worked with, it’s made me stop and go, I should somehow fit that in somewhere. Because the energy, the interest, the focus that each one of these professional people has had is off the charts. If I were to ever write a book, there’s a lot of good stuff that I’ve learned that it’s hard to relay in just a conversation, but it’s gold.


Cummings-Krueger: First off, spoken like a mentor, but yes, it is. I’ve been with Menttium now 16 years, and I don’t think there’s ever been a better time to have the benefit of a mentor right now. There’s just so much change going on. But it is true. Part of what I love about the cross company mentoring program is that you also get to broaden your perspective, not just them as individuals, but the context that they’re in. For example, this mentee you are helping her hands on manage through the change, which sounds like a fair amount of change going on.


When you think about our listeners, who are all going through a change, what have you found has been most helpful and seems to resonate when you’re helping coach and advise a mentee through the change they’re dealing with?


O’Brien: We had touched on it a little bit earlier, it’s staying in tune with the emotions that you’re feeling, and that reflecting, and empathy become foremost in the journey. It’s easy for our emotions to get the best of us when we’re in the swirl of it, that whole washing machine of emotions really gets you. For me, quite often it’s the role of reflecting back, this is what I’m hearing, and this is what it looks like, and so on and so forth.


We talk our way through it, and then we get to that point, the inflection point where we can start going in a specific direction that helps folks self-reflect. That’s the part that forces me to do the same thing. When you give advice or guidance, you need to be willing to take that same guidance and use it in the same way. It comes back to me in that form. The other thing is it can be very hard to let go of whatever it happens to be that you’re in the middle of. Moving from one thing to the next, we want to hang on to certain things and that doesn’t always pay dividends. We’re better off understanding that it’s time to let that thing go wherever it goes.


It’s easier said than done, and for me as a classic introvert, it’s like you can think too much about certain things too, and you must get out of your head. That’s why the network comes in, that board of directors, those people that you trust who can say, do you hear yourself right now? When you have a good set of folks who will tell you, and that’s the other thing, they must tell you, because you don’t always know. It’s one of those things that’s hard to really understand, but that’s it. Then going with the flow, I think is another big part. That may be just me. I can go with the flow like the best of them.


Cummings-Krueger: That sounds very peaceful.


O’Brien: It makes it fun though because you never know what the flow will bring you. You find yourself in places or with people or whatever it is, and it all kind of matters and it all goes together as far as that goes.


Cummings-Krueger: Mentoring is holistic; professional, and personal, it all develops together, and certainly you have been a constant learner throughout your life. I imagine there’s a lot of learning surprises, maybe changes in perspective that it’s easy to lose track of because they build upon each other. But I am curious about your perspective. Was there anything that surprised you that you didn’t realize that you heard from the other perspective?


O’Brien: Surprised in that I didn’t expect the way our lives intersected so much, and there’s so many things about our lives that are the same, but different. The perspectives that I got from my mentor at the time really challenged the norms that were in my head about how you handle things. It reinforced this idea that you must be open to all these perspectives, because if you are not, you let great opportunities get away from you. It would be easy to dismiss some of the things that we talked about. It would’ve been easy to say, this is going to be fine. But then you go, no, you need to stop right here, and you need to think about this, and then you need to take some action. It was the actions that I took in terms of changing the way I thought about things, the way I operated, the willingness to be more open. And that’s not always easy to do, that’s for sure. That’s the gift that keeps on giving.


Cummings-Krueger: Yes, it is. It’s like seeing through other eyes, isn’t it? That’s the essence of mentoring.


O’Brien: Definitely. There’s no question about it, but you must feel the person, you must really understand where they’re at. Finding out isn’t always easy. I would love to be able to reflect on all the mentor-mentee relationships I had and say they were all perfect, but they weren’t. There were a couple mentees that we were on different pages, totally and completely, and I’m thinking, this is not working. I must assume they were feeling the same way, even though it was never articulated, but I didn’t feel like I was helping at all.


Now you say to yourself, okay, what do I need to do to be different? I need to change this because this is not working. Some of it had to do with the choices that we all have to make. Sometimes when we find ourselves in this situation of, it’s hard making changes and the specific choices that must be made as a result are just not easy to do. It’s what’s the mechanism, what’s the framework for the choices that you must make? If I think about the origin of “run to, not from”, I think it comes from the idea that a lot of struggles, my own struggles, other people’s struggles, come from needing to make choices and those choices might be different than what you are used to or comfortable with or they are outside your comfort zone.


As a mentor, I knew that I needed to change my thought process. Once I did some of that self-reflection and understanding and going in a different direction, things started to click a little bit more. I think it’s getting older too. All these things go together. You and I talked about the three phases of life for the first 30 years, the second 30, and then whatever you have left the third 30. Here I am, I’m in the third 30, and I’m a very different person than the person in that first 30, but still with my foibles. You can’t change everything.


Cummings-Krueger: It’s interesting, a lot of this of course is the mentoring work you do, the internal work you’ve done, perspective, all of that. But in addition, your career has been in HR. You’ve not just led teams of HR professionals, you’ve helped leaders of all types lead within this context, and there’s such a parallel obviously, between your personal and professional and how it informs. When you think with the professional hat on and you’re working with leaders, I don’t know if what first comes to mind are the young leaders or the older ones set in their ways, but what do you find has been most useful to you when you are trying to help leaders in a professional setting?


O’Brien: First, I come to it with a long track record of experiences, especially in the coaching forum and in the mentoring forum, because it’s a particular passion for me. I think it starts with that, and then it becomes more about breaking through the barriers, helping people see things differently than they are presently.


It’s through being a more active listener, a more connected questioner. Sometimes when you just say things, it’s this, that, and the other thing, people are just turned off by that. When it comes to them as a question, now they have to say something. When they’re talking and they hear themselves, I don’t have to do anything because most people have got a lot of self-awareness. That’s the beauty of us as people. We’re aware of who we are and what we’re about, and it’s just how do you help get them and be willing to challenge. I think that’s the other thing, I find myself challenging a lot of people and I’m not afraid to challenge. But at the same time, I can be over the top sometimes. Would stop already, would you?


Gina, my wife, we’ve been married for 20 years, so we’re coming up on our 20th anniversary. She’s got this famous thing when “Tom’s being Tom”, and it means I’m over the top right now. And she’ll tell me, yes, you’re over the top right now. But you need that person who helps balance you out and that’s been Gina for me. She’s wonderful and like all the things that we’ve talked about, she’s one of the reasons life comes around again if you let it. Professionally, letting a lot of things go has helped immensely. You can’t control everything. Once you understand that, it’s not easier, it’s just different.


Cummings-Krueger: Yes, much easier said than done.


O’Brien: Yes, that’s the thing. There’s no magic wand, that’s for sure. It takes a lot of work. You must be open to change and think about it and going at it in an organized way. That’s hard to do too because you’re in it. You’re in this thing and it’s happening and it’s coming at you fast. So, slowing it down is hard.


Cummings-Krueger: What habits have you created for yourself because you have been successful, and again, none of us are perfect, but you have been successful in your life lessons. You have been self-aware, as you say, staying in the moment, slowing down. Are there any habits that you’ve developed that help you do that?


O’Brien: I always try to be planful in what I do. Anytime you’re approaching whatever it is that you’re trying to do, I try to think about what are the various strategies that I can employ to make it work better for me. There’s a lot of planning in there. I think who are the partners that I could connect with, who can assist? Who would bring a perspective to the game, looking for those people that I could really partner with and work with to make it go easier or more smoothly. I always think about what’s the simplest way to get that done? Get rid of all this complexity, all the things that get in the way. Those are the things that I really think about when it comes to taking action. At the end of the day, it’s all about getting stuff done. That’s the number one, I talked about my 7 P’s plus one, I just talked about three of them, but they’re all focused on getting stuff done.


Cummings-Krueger: Let’s just for a quick moment, I don’t know if you have them handy or just completely emblazoned on your brain, but why don’t you share the P’s?


O’Brien: As I said, performance is the first one and performance is all about getting stuff done. The next one is about being principled in this idea of being fair, honest, straightforward, yet always trying to be tactful. When you’re delivering information, you want it to be like that. If you ask me a question, I’m going to give you a straight answer from my perspective. We talked about the process step. You want things to be simple and flexible and be able to understand that people are going to be able to do this and it’s not that hard.


The next is planning. You can have the best strategies in the world, but if they’re poorly executed, they’re going to fail, and you don’t want that. Perseverance, you must stick with it. Being in human resources, I hear “no” a lot. No, we’re not going to do this. No, we can’t do that. If I’m selling an idea with facts and those facts hang together, often people will go, could we do it this way instead of that? Sure, yes. I’ll negotiate my way into anything as far as that goes.


For me, it’s about passion. In my profession, you must have passion for two things. The passion for the profession, I want to be around people who love what I do as much as I do. Human resource professionals, I love them, I can’t get enough of them. Then there’s passion for service; we must be willing to serve. We’re the ultimate influencer. We’re the one at the back of the stage. We’re not the stars, other people are stars. We must be willing to take that role. We’re the whisperer in somebody’s ear, and that’s what we do to try to help them be better. We must get our accolades in that fashion. When we see someone succeed, we know we had a little part of that, which is cool.


My funny P is fun, P-H-U-N. It’s not rocket science. We can have a lot of fun, a lot of laughs, and that’s what we must do because if we take things too seriously, no, forget it. I don’t take myself that seriously, and I expect to have fun on a regular basis while we’re getting stuff done. The last one is all about partnership. Who are our partners and how do we help them and how can they help us? Those are the things that I’m after to a large degree and have been for a long time.


Cummings-Krueger: It’s just wonderful intentionality. I love the P hook of course, but it lays out so nicely.


Last question, which is a catchall question because you’ve really been pouring out your perspective already. If I asked you the classic question of, what do you know now that you wish you knew, what we hear so much from leaders, especially starting leaders, is all the challenges that they’re facing. What would you like to say that you haven’t had a chance yet to?


O’Brien: I always think about it as my parents used to say, don’t bring embarrassment upon the family when you go out. I always interpreted that as, always bring your best self. If I think about what that means, it’s like this version of me can be better. I need to think about it like that and some of these things that we do struggle running to versus from. We do struggle with the idea of letting things go. If we could just try a little bit better as it relates to that and making the commitment to yourself and then following up on that. Because it’s easy to say, it’s harder to do, and so for me it’s make that commitment to yourself to be that better version and then follow up on it. I could just wave the wand and everyone out there would discover this.


Cummings-Krueger: You know what Tom? I would say, you’re doing a darn good job passing it on, you have that mentoring mentality. We are so grateful to have you as a partner and thank you so much for saying yes to this conversation. This has been a great conversation, but also, I think it’s going to be a great perspective for our listeners. Thank you, Tom, for such an open and insightful conversation about change, how it impacts us, our perspective, and then passing it on, which of course brings us back to the essence and the power of mentoring.


Thank you all for listening to this Menttium Matters podcast. If you enjoyed this episode, please feel free to share it with friends and colleagues, and if you are interested in additional resources, you can find our show notes on the Menttium website.


We look forward to having you back for our next episode.