E116 – I’ve Made it, Now What? featuring Tami Reiss

What happens after you've "made it" to that coveted leadership position?

This question haunts many emerging leaders who suddenly find themselves at a plateau, uncertain about their next move. Product Leader Coach Tami Reiss brings refreshing clarity to this leadership conundrum, offering a powerful framework that can transform how you approach your career journey. Having navigated from physical therapist aspirant to nonprofit consultant to tech company CEO by age 33, Tami understands firsthand the complexities of charting an authentic leadership path.

At the heart of her approach are three deceptively simple questions that can help you navigate any career crossroads: Where do you want to go? Where are you now? And what should you do next? These questions shift your focus from merely reacting to opportunities to thoughtfully considering how each move aligns with your deeper goals and values. As Tami explains, we typically waste energy on feasibility questions (Can I do this?) when we should be asking valuability questions (Does this move me toward my goals?).

Through practical exercises like mapping your "perfect day" and seeking honest feedback from those who know you best, you can gain the clarity needed to make decisions that align with your authentic self. Her refreshing perspective reminds us that with careers spanning 40-50 years, there's always time to pivot, learn, and grow in new directions.

Tami’s Episode Links:

1. LinkedIn: Connect on LinkedIn

2. Website: tamireiss.com

Tami’s Recommended Book/Movie/Podcast List:

Movies:

1. A Bug's Life

2. Good Will Hunting

3. Forest Gump

Podcasts:

1. This is Product Management

2. Rocketship.fm

3. Freakonomics Radio

Books:

1. Inspired + Empowered by Marty Cagan

2. Never Split the Difference by Chris Voss

3. The Night Circus by Erin Morgenstern

Chapters

• 0:00 Episode Introduction and Land Acknowledgment
• 0:55 Welcome to Trench Leadership
• 2:31 Meet Tammy Reiss: Product Leader Coach
• 5:42 From CEO to Unhirable: Leadership Challenges
• 11:09 Three Questions That Solve All Problems
• 20:34 Finding Joy in Your Career Path
• 27:30 Perfect Day Exercise for Leaders
• 30:39 Learning from Career Missteps
• 35:57 Finding Your Path Through Self-Honesty
• 42:36 Final Thoughts and Contact Information

Transcript

Simon Kardynal: 0:07

I would like to begin this episode by acknowledging that I am located in Ottawa, Ontario, Canada, and I am privileged and honoured to live and learn on the unceded, unsurrendered territory of the Anishinaabeg Algonquin Nation.

Glen: 0:24

Hello, you're listening to Trench Leadership: A Podcast From the Front, a show for emerging leaders from all professions to hear from other leaders who have led from the front, made the mistakes, had the triumphs and are still learning along the way. Produced by Jennifer Lee at it's a Legit Business, a podcast launch and management company. And now here's your host, Simon Kardynal.

Simon Kardynal: 0:55

Hello and welcome to Trench Leadership: A Podcast From the Front, a show for emerging leaders. For many of us, getting into a leadership position is the first step of having made it with finger quotations, often with the goal of becoming a leader as that career goal. But what happens when you've gotten to this point? Where do you go next? How can you maximize your moment? In this episode, you'll hear from Tammi Reiss, a product leader coach, who will offer advice for emerging leaders to make the most of their first leadership role. Tammi will also talk about how emerging leaders can realize their long-term goals. Ensuring the journey is the one we want to take. Well, folks, as always, I have the guest here and I'd like to go ahead and say hi to Tammi. Hey, Tammi, how's it going?

Tammi Reiss: 1:43

Good. How are you, Simon?

Simon Kardynal: 1:44

Oh, fantastic. We've been working a little bit to get this together and thank you so much for your patience to get us to this point, but here we are, we made it here.

Simon Kardynal: 1:54

This is going to be a lot of fun, but before we get into it, I would like to do a visual interpretation, and for myself. I have my microphone in front of me. I'm wearing my black golf shirt with the Red Trench Leadership logo over my heart. My background is a virtual background of a stone wall with the Trench Leadership logo hanging. It is white with a purple glow around it, the irony being that the logo is actually meant to be red, but that's what happens when you order something on Amazon. What can you do? So these things happen. Tammy, would you like to take a moment and introduce yourself and give us your visual interpretation?

Tammi Reiss: 2:30

Absolutely, and as somebody who sits on a board for a nonprofit that is all about disability inclusion, I love that this is something that we're doing. I've never been asked to do it before in any of my other podcasts and I'm going to try to encourage other people to do it. You're going to start a movement, Simon.

Simon Kardynal: 2:46

Fantastic, I'm happy to hear it.

Tammi Reiss: 2:48

Hi everybody. I'm speaking to you from Miami, Florida, and I have a virtual background as well. I'm not wearing glasses, but I am wearing a very lovely gold chain with some circles on it, and my virtual background looks like an office with a white wall, a bit of industrial space. And then I have this cute little black inset here which says product leader, coach, which is my company name, and then it says focus on your strengths, advance towards your goals, which is my tagline.

Simon Kardynal: 3:21

Great Well. Thanks so much for that, and I appreciate taking the time for that.

Tammi Reiss: 3:34

I am wondering, before we get right into our conversation, would you mind taking a couple of minutes and just telling us a little bit about yourself, your journey and really how we got to this point? Like to be called. Ever since I went to UCLA as an undergraduate, that's what I've been called, but when I moved to New York, people used to call me Tammy from LA, and I would have to explain that I was Tammi from Miami. And now that I'm back here.

Tammi Reiss: 3:56

I can't use that as often, but I have a very weird background in the nature of where I started is not where I am now. I have a degree in physiology. I was supposed to be a physical therapist. I then went to business school to learn how to run my own clinic, and while I was there I learned that I actually wanted to help people in other ways and I wanted to be a nonprofit consultant, and so I worked for some big brand name nonprofits for a while, and then I realized that in order to teach them how to work like a corporation, I needed to actually work at a corporation, and so I did a bunch of that, and I was lucky enough to be tapped for something called product management, which I summarize as the group of people in an organization that decide what to do next, and I'm very good at making decisions.

Tammi Reiss: 4:46

It turns out, and I have spent the last 18 or so years in product management at tech companies, either as a consultant teaching people how to do it, an educator teaching people how to do it, or actually doing it myself in-house at some really wonderful companies and some less than wonderful companies, and around two years ago I hung up my own shingle to be product leader coach, which means that I'm an executive coach for product leaders at tech companies and I help them realize how to do their jobs better or how to present something better, because the higher up you get in your career, the less you can turn to your boss for help or the less you want to because it might influence their confidence in you.

Tammi Reiss: 5:30

And so I get to be this awesome sounding board and coach for some really excellent, fantastic product leaders around the world. I have clients all over the world and the way I got to be talking with Simon is that my friend, mark, who I've collaborated with a few different times, wrote a fantastic book and he was a guest on Simon's podcast and he recommended me to be the same, and I enjoyed my initial conversation with Simon enough to spend more time with him and more time with all of you.

Simon Kardynal: 6:01

Well, thanks so much for that, and we did have a fantastic chat. You know, sometimes you can just kind of tell when people are going to click, and we, we ended up speaking, I think, well beyond the 30 minutes we had originally set for, and that's. That's part of the thing. I think is your. We just kind of blew past that and didn't even realize it, if memory serves.

Simon Kardynal: 6:16

So, it was great, yeah, absolutely, absolutely. And you know I I love the how your background has tied you towards going to becoming this a product leader, coach, like that and how to be able to move into those things, because quite often we and quite often we get to these roles inside large organizations especially if it's a large organization, it's it's safe to be there and go up that chain of command or that, that corporate structure, because it's easier to know you have the safety to stay there and there's nothing wrong with that. I'm not suggesting good or bad, I'm just saying that's a fact.

Simon Kardynal: 6:51

Um, I'm not really bad, by the way yeah, yeah, it is challenging, so, uh, you know. I'm wondering what happens, though, whether or not we decide to stay inside an organization or if we stretch our legs, because at some point in time, especially with those first leadership promotions, we're going to ask ourselves great, I made it here, but now what? Where do I go? What's next? You know, what do we do?

Tammi Reiss: 7:14

Well, you try being a CEO at 33, because that's what I was. And when I had that company sold and I was then looking for a new job, I was almost unhirable because I was looking for mid-level manager positions. And who believed that a CEO didn't want to be a CEO again? And I really did not want to be a CEO at that exact moment.

Simon Kardynal: 7:43

Oh yeah, I couldn't imagine.

Tammi Reiss: 7:44

Yeah, so, um, but I think my one of my favorite moments was, uh, the person who ended up hiring me, a woman named Camila. When she interviewed me, she said have you ever managed anybody before? And I just paused and she said well, that's a dumb question. You are a CEO. Obviously you've managed people before. A CEO, obviously you've managed people before, and I was like yeah, that's just once or twice a little tiny bit of experience.

Tammi Reiss: 8:14

It was a small company. Right, there were 12 or so people, so it wasn't like I was CEO of this huge conglomerate, but nonetheless I had definitely managed people and profit and losses and PNLs and had to fire people and had to hire people and had to do lots of strategic thinking to get a company out of the hole.

Simon Kardynal: 8:30

So, yeah, Well, and that's a big part of it, I know, I do wonder and I don't know. I genuinely don't know. Ceo of a small company, ceo of a large company? There's probably different responsibilities but, at the end of the day, ceo responsibilities are CEO responsibilities. There has to be many things that are going to roll across each other.

Tammi Reiss: 8:51

Yeah, I don't think most CEOs of large companies take the subway down to one of their clients because they owe them $120,000 and they weren't going to make payroll without that $120,000.

Simon Kardynal: 9:06

Gotcha, gotcha. Yeah, definitely a little different.

Tammi Reiss: 9:10

Sure, as I led, you want to talk about trench leadership, that is, leadership in the trenches getting on the subway to knock on the accounting accounts receivable door of a multi-million dollar corporation to say yeah, yeah, owe us some money, we'll take the check, please okay, okay, yeah, so definitely tactical in in its nature, which is ironic because a lot of times, people think, oh, CEO, wow, you must be able to make there and do that.

Simon Kardynal: 9:38

That person has made it, you know, they're there, they've got it, they're done having to go and go get checks and those different types of things.

Tammi Reiss: 9:45

Uh, for, a good friend of mine owns a custom bike, uh, refinishing business, and the assumption is, though, you own a business, you must be rich no or or not the case, or you're trying to make ends meet, you know, and part of running a business is the weight of all of your employees on you. You have to make these decisions that hopefully grow the business, that hopefully keep bringing customers in, that hopefully keep bringing money in, that not too much money goes out so that you can still pay payroll and otherwise. And people rely on that for their rent money, to buy food, to take care of their family, to go on vacation, to have health care, and that's all on you. And a lot of people don't understand the responsibility leaders walk around with on their shoulders at all times.

Simon Kardynal: 10:42

It's not an easy job, oh yeah yeah, no, it really isn't, and I think that's something in the spirit of what we're talking about here, something that for leaders to think about when they want to strive to get to these positions and they find themselves there. The first question that seems to me would be the a good one to ask ourselves introspectively is you know, what do I want to do next? And then, when we've asked ourselves that question, be honest, like does that make sense at all? Do you have any thoughts on that?

Tammi Reiss: 11:09

Yeah, so I actually say there are three questions that solve all problems.

Tammi Reiss: 11:14

I call them, the only three questions you ever need. And what should I do next is often where people start the question, but that's actually in my mind. The third question and the first question should be where do I want to go? What is my goal? Long-term thinking, three to five years out, five to ten years out. What are my values? What kind of balance am I looking for in my life? What kind of adventures do I want in my career? What kind of experiences do I want to be able to be available to me?

Tammi Reiss: 11:48

And when you start there, it helps really frame any of the rest of the decisions you have to make, because you can say is this going to help me get closer to my goal? And so the next question is where am I right now? Right, because in order to know how far you are from your goal, you got to know where you are. And so we start out with where do I want to go. We then add on where am I right now? And then ask where should I go next? And you evaluate what is the best next step that helps you get closer to the goal from where you currently are. And I call them where to? Where now, where next?

Simon Kardynal: 12:32

Thank you so much for that. I'm curious did you come up with these three questions based off of the experience that you had throughout your career, or things you observed? A little bit of blend of everything. How did they come about?

Tammi Reiss: 12:42

So, as a product manager I mentioned earlier my job is to figure out what to do next, and as a product leader, your job is to figure out what to do next. And as a product leader, your job is to figure out what to do next for a lot of things, and nowadays in product management we talk a lot about outcomes over output, that you want to be aligned with goals, etc. At which point we have, I ask a lot of people what are your goals? And so those two became really crucial. And then I had the pleasure of working with Melissa Perry, who wrote a book called Escaping the Build Trap, and she talks a lot about something called the current state and how it's important for you to quantify and qualify your current state before making a decision.

Tammi Reiss: 13:26

And one of the things I did with Melissa was I was leading a training for her product called Product Institute, and I was doing corporate training for brand new product managers that were part of an associate product management company at a brand I promise all of you know and one of the largest companies in the world, and I was explaining to them this goals thing and current state thing, and I used the analogy of Google Maps and I said it's pretty much like Google Maps. You have to set your destination. That's the first question it asks you, and then it says where are you, where do you want us to map you from? And it defaults to your current location, and then it gives you options on how to get there, because, in reality, there are lots of options on how to achieve your goals, and, more often than not in life, people are offered an option and they then ask feasibility questions about how can I make this happen.

Tammi Reiss: 14:29

Does this work with this? Can I juggle this with everything else? As opposed to valuability questions, is this something that helps me get to my goals? Is this something that I will value? Is this something that adds value to my life? As opposed to can it be done?

Simon Kardynal: 14:48

And so that was where I came up with the three questions that's interesting, and what I hear in all of that and correct me if I'm wrong is it's these questions are designed to have the person have an honest look at themselves, and honesty is not a new concept. We're not going to be like, oh be honest, I wish I'd heard of that before. It's a it's a thing, but in reality of it is quite often it's difficult. Be honest, I wish I'd heard of that before. It's a thing, but in reality of it is quite often it's difficult to be honest, especially depending on whatever the culture is.

Simon Kardynal: 15:14

I know for myself when I was in the military, one of the metrics of perceived success was to go up the rank structure, and if someone didn't want to go up the rank structure, then they were perceived as not being successful as an example. But if someone was okay with that, who are we to judge that? It's that honesty and it's an interesting spot to be at when we're able to actually be that more honest, that much more honest with ourselves. Do you have any thoughts on that at all?

Tammi Reiss: 15:41

Yeah, my first job at a nonprofit. As I mentioned earlier, I was a program manager, which pretty much means I was a event planner, fundraiser, and the leadership of this large national nonprofit was very impressed with certain things I was doing and they started grooming me towards becoming an executive director of one of the regional offices. And I said to them at some point I look at what my boss does, this regional director position. I don't want to do that job. That job isn't of interest to me. It's just a lot of reporting and spreadsheets of things that were done. You're not reaching the community anymore. You're not doing the fundraising actively anymore. It's a lot of pure management and that's not what I wanted. And they were very surprised because that was rising up the ranks. And I said that isn't the fundraising actively anymore, it's a lot of pure management and that's not what I wanted. And they were very surprised because that was rising up the ranks and I said that isn't the path I want.

Tammi Reiss: 16:36

And I've forged my own path and there were many, many years where my parents, among others, were not sure I would make anything of my life Because I had gone through so many jobs and so many lateral moves that it was like people quantify or qualify success as moving up, when in reality, success should be finding a place where your strengths can be leveraged for good and you feel good about what you're doing at the end of the day. So, as an executive coach, do I make as much money as I did when I was a vice president of product? Absolutely not. But do I feel great about the impact I can have on my clients' lives 100%? Do I feel great about the fact that I can actually hang out with my kids 100%? Do I feel awesome about the fact that I get to travel to conferences and speak and inspire people with speeches like the only three questions, 100%? This is what brings me joy and that's so much more important than other people externally saying you've made it or you've been successful.

Simon Kardynal: 17:50

And that's a great point you brought up talking about joy. The fact of the matter is we spend a big part of our waking day on our careers, on whatever it is to do, whatever we need to do. So if we're able to find some joy in that, that's great, that's even better. Sometimes that's just not the case. Sometimes that joy, that job we have, that has, all that joy that's going to go away and it's all about adjusting it. I know for myself.

Simon Kardynal: 18:14

I always knew I wanted to be in the military, and longtime listeners of the podcast will have heard the story numerous times about how, after 26 years of doing fairly well in the Canadian forces, it was time for me to do something else, because that joy that I was getting of being in the forces just simply wasn't there anymore. It was time to do something else. So I completely stepped away from the military for a little over two years, and now I've actually, with that time I was actually able to. I am able to work in the military as a reservist, so I still get to do the parts that I enjoy doing and I still have other things that I'm able to follow and have passion in multiple different areas, and it's about finding the way to find those balances and having the patience to have a real look at it. I think patience a lot of times comes with being honest. I think they're intertwined. Do you have any thoughts on that at all?

Tammi Reiss: 19:02

100 percent. But the thing that's coming to mind is that, on the basis that this podcast is about leadership, so much of a role of leadership is to help inspire the people on your team and the people you're leading to feel joy in their work, to find meaning in their work, to find balance in their lives and to help them find a role that's going to help them feel impactful and joyful and masterful and all the things that help people feel good about their day. Because, you mentioned, we dedicate a large portion of our day to our work life. My dad often says your life, your time on earth, is pretty much divided into three things your time with your family and friends, your time at work and sleeping. And if you're not enjoying your family and friends and you're not enjoying your job, chances are you're not sleeping very well.

Simon Kardynal: 20:03

Yeah, it's very true.

Tammi Reiss: 20:06

And so if you're going to put one third of your life into something, make sure it's something that you can either feel joyful about the result of because it's helping finance your other passions, or that you actually really feel great about the work that you're doing. You know.

Glen: 20:26

Oh, hello there. It's Glen, the voiceover artist, and if you're hearing me, that means we're at the midpoint of this episode. Are you considering starting your own podcast? Are you confused or overwhelmed and don't know where to start? Well,J ennifer at "It's a Legit Business is a podcast wizard who can help you get started, provide advice, consultation and help you get started. Provide advice, consultation and help you along the way. Trench Leadership has been using it's a Legit Business for over a year and Jennifer offers personalized service catering to the podcast's unique needs and desires, truly hearing Simon's requests and being instrumental in realizing Trench Leadership's vision for each episode. If you want to get started, contact Jennifer at Jennifer at itsalegitbusinesscom and she'll help you realize your dreams. Trench Leadership is always striving to improve our content and provide valuable insights for leaders across all professions, and to do this, your feedback is crucial. So drop us a note at simonk at trenchleadershipca and let us know what's working and what can be improved. And now back to the show.

Simon Kardynal: 21:42

Yeah, so that's really interesting. And when we're talking about how people and leaders can they get to that point, they plateau because they realized whatever their their goal was, whatever that might be, what's next. How do you have any type of advice to help that leader decide where to go next and maybe find their new direction?

Tammi Reiss: 22:03

So one of the things I encourage people to do which I did many, many years ago as part of a group coaching program that I was a participant in is to invest around a half hour writing down your perfect day. Write down from the moment you wake up to you going to bed. What does your perfect day look like and it could be a Sunday or a Wednesday or anything in between but really consciously think about what would a day look like that at the end of it, you'd be smiling ear to ear. Who are you talking to? Who are you meeting with? What are you doing? Where are you? And start there, because that is, to a certain degree, of visioning exercise. You're envisioning a life that you want and so then evaluating again between the goal and your current state, like where are there gaps? Are there people you want to be spending more time with? Are there people you want to be spending less time with? Right, are there things you want to be doing more of or less of?

Tammi Reiss: 23:06

In that perfect day, were you more active than you currently are? Are you more sedentary? I don't know, but whatever that is, figure that out. And I think another thing that can be really helpful is talking to the people who know you. Talk to your partner, talk to your children, talk to your parents, talk to your really good friends about what they think will help find you joy. I have a client whose husband said to her, like I don't think you're ever going to be happy at a company. And I know my husband said to me I don't think you're ever going to be happy with a boss because I really don't like actually having a boss.

Tammi Reiss: 23:45

But he's right, I don't really enjoy having a boss. It's not that I don't learn from bosses.

Tammi Reiss: 23:52

I just very often move on and I'm like, okay, like let's, let's do something next. And so I think that very often, the people closest to us see things that we're not being truthful to ourselves about, like you were saying right, and they, to a certain degree, speak truth to power, right, and they tell you the things that you need to hear and they say to you I saw you smiling ear to ear when you were doing X. Do you remember when you had this job and you used to come home so excited and tell me stories about this? Maybe you should do something related to that, and relying on the people around us as sounding boards and as feedback loops really can be very helpful in figuring out what to do next. It's still your choice, right?

Tammi Reiss: 24:44

I often say, as a coach, I'm going to give you advice, but it has to feel authentic to you. So if you don't like it, tell me why and I'll give you new advice. So whatever advice you're receiving, it still always has to feel authentic to you. So don't just follow blindly something someone else has said, but use it as an input that helps you understand what is the long-term that's going to make you happy and then what should be your next step.

Simon Kardynal: 25:15

And it's for myself it's okay if we don't know exactly what that is right away. My experiences have been like often in the busyness of life and and in especially in any type of corporate environment, there's an almost an expectation, an unsaid expectation, to know exactly what you want to do and know all the steps and stick to that plan, even though often they talk about flexibility, but in my opinion, very rarely do people actually mean that. Do you have any thoughts?

Tammi Reiss: 25:42

Yeah, absolutely so.

Tammi Reiss: 25:43

In product, we talk a lot about the lean cycle, which is build measure learn a lot about the lean cycle, which is build measure learn. And when Melissa and I talk about how to get from your current state to your goal state, there's a lot of uncertainty there and it's not going to be a linear path. Very often, the next step is simply learning something right. Your current state is not enough knowledge about something and therefore the next step is get more knowledge, get more data, interview some people, talk to some people in the field, talk to a few companies, do some research, because the current state isn't only what you have, it's also what you don't have, and very often, what you don't have is knowledge, and so you often have to start the build measure learn cycle at learn, because you don't necessarily know what to build and so, similarly, you may not even know the options out there to you as to what a next step could be, unless you do some research and talking to people and learning, because your current state is a lack of knowledge yeah, absolutely.

Simon Kardynal: 26:53

Uh, and on more than one occasion throughout my career there were certain jobs, certain positions. I thought, wow, this is going to be amazing. I, I can't wait, that's my career goal. And then I'd get in the job and realize that it's nothing like I. I thought it was going to be. It's kind of like meeting your hero and it's it's. They're not that same person, you know. Yeah, exactly, and I'm like, well, well, shit, now, what right? Like what do you do now? And do you have any type of advice for someone that they, when they experience that type of moment where they're like, oh crap.

Tammi Reiss: 27:26

I think, first of all, embrace it as a learning right. Right, don't beat yourself up. You made a mistake or you were wrong, or you went in the wrong direction. You learned that wasn't the direction for you. That's a positive outcome. There's a positive outcome to I took a step and I learned that wasn't for me. And actually take a moment to analyze why that is. What is it about it that you were hopeful for? That is meeting these expectations, and where were there things that you had to miss? You know alignment of what it was actually going to be, and then say, okay, those are things I don't want again. I don't want to have, I don't want to work for a company that does you know work with the CIA or whatever.

Tammi Reiss: 28:16

It is right or I don't want to work for a boss, that's remote.

Tammi Reiss: 28:18

Sometimes it's something that you don't even realize is going to be a challenge. Or I don't want to work for a company that's in time zones ahead of me versus behind me or vice versa, right, and there are all of these things that you can figure out and really treat it as a learning experience, because, as I say to my three-year-old daughter, we make mistakes and then we learn. Mistakes aren't a bad thing, mistakes are how we learn. It's the easiest way to learn is to make a misstep, and so, if you can embrace that you made a misstep because what do you know? You're human and we all make mistakes Now you have the opportunity to learn from it, and that provides you the opportunity to grow and to get even closer towards where you want to go. But you might take 17 wrong turns along the way, and that's okay.

Simon Kardynal: 29:18

A big theme for me in life in general is dot, dot, dot and that's okay. I say that many, many, many times and because it is, mistakes are okay. I'm going to switch gears just a little tiny bit because as we were talking about that, a question popped into my mind and I'm wondering in your experience as a coach and I would imagine that you have had it seems to me that you would have had clients who maybe, when you're asking them questions, you're trying to get to help them get to their point where they're being honest with themselves. Maybe they're lying not to you but definitely to themselves, and you're probably, from the outside, able to see that. So I'm curious when you're in those types of roles, have you seen any types of similarities in people in a broad sense? To tell when they're lying to themselves and lying might sound kind of strong, but maybe not being as honest with themselves about what they want to do. Are there any type of physical cues or that type of thing?

Tammi Reiss: 30:19

I am not as good about picking up on body language, but what I have found is that very often, when someone knows that they aren't fully being honest, they tend to over explain, they try to justify and they they're like, because this and this and this and they they'll go into all of these details that justify something that they know isn't authentic and isn't a truth. And then I'll say, OK, well, like, let's piece these pictures to put these pieces together again. I don't think A correlates with these things that I'm seeing. Right, you told me these other things happened and if this were to be true, those other things wouldn't have happened. This actually happened yesterday with one of my clients. So I work with leaders, which means they're often smart, accomplished people who occasionally and I would never fall into this category like to be right.

Simon Kardynal: 31:23

Don't hear any sarcasm in that one at all.

Tammi Reiss: 31:25

Nope, I hate being right with a passion in that one at all. Nope, I hate being right with a passion. And this particular client was talking about how they love being right so much. Sometimes they push it a little too far with other people and they were beating themselves up for doing it a few times and I said don't beat yourself up for that.

Tammi Reiss: 31:48

I said first of all, like you were cognizant in these other situations, right, like when you knew that behavior wasn't good cause, you brought me in, you brought in peers and that's growth, right. But you still got a problem and we still have room to work on ourselves and we're all in motion and we're all works in progress, and so that's okay. But he was being a little like too self-fledgable jury and I was like no, like you don't have to beat yourself up. Sometimes it's a negative, right that? Like he was beating himself up as to this untruth, that he was a horrible person who was doing this all the time, and I was like that isn't the case either, right? So sometimes it's, you think you're really wonderful at something and sometimes it's not.

Tammi Reiss: 32:49

I had a client who I changed her whole perspective on the way she worked and thus she has been much successful but super smart, super capable person. And she told me that very often when she was in a room, someone would bring up a problem. She would suggest a solution. That would be the suggested solution and then the question would be okay, who wants to implement that solution? Someone else would raise their hand and then they would get the credit for actually implementing the solution.

Tammi Reiss: 33:05

And I said well, why don't you raise your hand? And she said I don't want to step on people's toes. And I said that's not really a reason, right, like, and that's that's not a truth in the world that you're not actually stepping on someone's toes. And I I said what can we do to help you raise your hand? And I thought about it for a while and I coached her for a while, long enough to know certain things that she found valuable, and I said to her I said if you are on that project, will it be more successful? And she said yes. And I said do you bring value to not just the idea of the solution but actually implementing it and dealing with the bumps in the road along the way? And she said absolutely yes.

Tammi Reiss: 33:48

And I said great. So you're not raising your hand in order to step on someone's toes because that isn't your personality, right? She said no, it's not my personality. I'm not political and aggressive that way. I said you're going to raise your hand because when you participate in a project, it has a higher chance of success, and higher chance of success helps the company, it helps everybody involved and therefore you're not raising your hand to step on someone's toes. You're raising your hand so the project or the initiative could have more success. And then all of a sudden, she said oh, and I said yeah, because you're smart enough and you're capable enough and you're organized and you're good at this, so it's a good thing for you to be on a team. And that was really transformative for her.

Simon Kardynal: 34:38

And sometimes people just they just need to hear it. And when someone is completely outside their sphere, completely impartial, because it's like anything. If your mom or your dad says you know, you're beautiful, I, you know, I expect my mother to tell me that I'm a good looking man. You know, it's my mom right, I'm expecting that, you know. But if you know someone else completely outside the world says that it's going to carry a bit of different weight or different perspective, for sure, does that make sense at all yeah, absolutely, I have a, I have a.

Tammi Reiss: 35:08

So the job market right now is very hard for people in tech. There have been countless layoffs of hundreds of thousands of people. So it is a hard job market. And I have a client who I'm helping her with promoting herself towards getting a job and she had two interviews with two brand name companies this week and she said I always don't make it past the final interview, like there's something that goes wrong. And I said don't beat yourself up, there's nothing that goes wrong, right, like, whatever they're looking for, at that point you're one in three people, right, you've got a one in three trance that every all the stars are gonna align.

Tammi Reiss: 35:45

And I said to her I said take it as a compliment that you're even getting to that stage. You've told me that online on LinkedIn, you can see that this role had 750 applicants. So, out of 758 applicants, you were one of the hundred people that they actually had a phone call with her 30 people they had a phone call with. And then you were out of the hundred people that they actually had a phone call with her 30 people they had a phone call with and then you were out of the 10 people they had a second phone call with and now you're part of the select three out of the initial 750 people who are getting to go to this final round. That is a compliment and that is an accomplishment, even if you don't get the job. And that was like. I had to say it a few times. And she still hasn't fully internalized it because she's still afraid she's going to get rejected. But it's important to have these outside voices that remind you you're awesome.

Simon Kardynal: 36:38

Exactly, and I mean, I think it's human nature to want to safeguard ourselves a little bit, that fight or flight instinct that we have just built into us. It's a lot of times people will push towards that negative outlook. So if they don't get it, then that's okay. I guess I didn't, I couldn't get it for whatever reason. I move on and be disappointed, and that made sense. I wasn't the right person. But then when you get it, you can be pleasantly surprised at where you got to that point. And it's interesting because often when we get to those points then we're looking around and we're like, well, great, now what? If only I feel like someone should do an episode about that and talk about what do we do when we hit to that point? What?

Tammi Reiss: 37:18

Would someone should totally do that. How do we decide what to do next?

Simon Kardynal: 37:21

Where do we go with that?

Tammi Reiss: 37:22

Questions that could help us yeah, exactly so I use very generic uh examples when I give a speech about the three questions, and one of them is like how do you choose where to go on vacation? Because very often someone says, hey, do you want to go to aruba? Or hey, do you want to go skiing? And then it becomes a feasibility question oh, when can I go skiing? Do I have the right gear, the right budget? But instead it should be like what kind of vacation am I looking for? What are my goals of this vacation? Am I trying to visit family? Am I trying to be cultured? Am I trying to do something with my children? Am I trying to get sun, escape the cold or go to the cold?

Simon Kardynal: 37:58

Do like understand your goals before you start choosing where you're going to go no, absolutely, and understanding that is important where you want to go and figure it out from there. It just kind of makes sense. I'm wondering. So how do you have any type of advice for people to other than the three questions where they might decide what their next goal could be?

Tammi Reiss: 38:20

I would look at people who inspire you, Right? I think that's a good place to start and like do you want to be them or do you want to work with them or things like that, or do things that are similar to them, but again dissecting it in the same way we dissected earlier why a really exciting job turned out not to be so great and what we can learn from that. Dissect what it is you like about someone that you find inspiring, right. Is it because they're entrepreneurial? Is it because they're caring? Is it because they're empathetic?

Simon Kardynal: 38:50

Is it because they don't care?

Tammi Reiss: 38:51

hey're just free-willing and they just say whatever they want. Is it because they're incredibly rich or that they have a really big family? Like what is it that you're aspiring to right, breaking that out of what you're looking at and being true to yourself about what is it that you're aspiring to right, breaking that out of what you're looking at and being true to yourself about what is it that you're admiring in that other person and their life and hopefully finding a trend amongst the number of people you admire? And they don't have to be famous, they could just be people in your neighborhood that you admire.

Simon Kardynal: 39:20

So, yeah, yeah, I love that and I think that's an important thing is to look at the others and see what you like about them and see what you, what, what speaks to you. I find for myself, you know, when I, when I want, the reason I wanted to join the military so often was because my father was in the military and and I remember him coming home from wearing his uniform now and and I think, wow, he's doing something important. He gets to, you know, for all the military's challenges I'm not going to it's not a shame on you. I know what was I thinking and and you know, and I admired the fact that you know he, I believed he was doing something very important and that was why I wanted to join the military, so I could do something like that. And then, you know, when I got in, I you know this is as a teenager and then when I finally got into the military and I was doing my different things, I was telling him, said, you know, the reason I joined the military was because of this, these reasons, and I'll never forget he's like, well, okay, great, but I joined the military because it was a steady job and and and it gave me a trade.

Simon Kardynal: 40:17

He's like I wasn't thinking about those things and that that stuck with me for a long time Like damn it, damn it, damn it, damn it. And then after a while I realized no, regardless of what I thought, I still that reasoning for me resonated with me. So it was okay. There was nothing wrong with him having a different way of looking at it. It didn't minimize anything that I was doing or what I wanted to do and why that message still resonated with me and he was still a part of that. Do you have any thoughts?

Tammi Reiss: 40:48

You had different goals, but you ended up in the same place yep fantastic win success either way, you accomplished your goals right. It turns out there are lots of ways to accomplish goals and lots of goals that can be accomplished by doing the same thing exactly and, like I said earlier, I think it comes back to being flexible and how you get there.

Simon Kardynal: 41:13

Really, that it's. It's a journey, and then it's not going to be a straight road, uh and it's, but we'll get there you'll get there you'll make your time and it's sort of like watching a movie everyone's gonna have take something else out of it.

Tammi Reiss: 41:27

You were all sitting in the theater together and every one of you had a unique experience and every one of you was something slightly different and therefore, like when you look at what other people are doing, don't judge yourself based on that. Find, as I said, the tidbits of why you look towards that as aspiration. Right and whatever. It was about your dad that you admired, that he came home and that he was giving back right, that was the next level of it. Like that's what you admired, and I'm sure that you could have become a cop or a firefighter instead and still emulated that nature of giving back to your community. Military was one way to do it and that was the way you chose, but your goal was to give back to your community, to serve your community, and there were many paths to get there.

Simon Kardynal: 42:15

Yeah, absolutely, Absolutely Well, thank you so much for that. This feels like a nice time to ask you. Hey, do you have any final thoughts before we move into the lightning round?

Tammi Reiss: 42:27

I think I say this a lot it's our careers are long. Our lives are much longer than they have historically ever been. You're going to be working for something like 40, 50 years. Do not feel stuck. If you are not happy, if you are in a place that isn't bringing you joy, that doesn't make you feel impactful, figure out where you want to go and then figure out the steps to get there. If it involves night school, go to night school. If it involves moving, figure out if you might need to move right, but it might not be immediate and not all changes have to be tomorrow. This is going to happen. But if you can think longer term out, you can think of incremental steps that are going to help you get there and you will be happier for it. But don't beat yourself up and say, well, this is just the way things are and do it for the next 30, 40 years. It's too long, it's too much time wasted and you have more than enough time to change directions.

Simon Kardynal: 43:35

Perfect. Thank you so much for that. Well listen, tammy. We have had a fantastic conversation and I'm curious. People have had an opportunity to hear from you to hear from you and your your look at an outtake on things but if they want to know more about you, they want to engage you for some potential coaching or just have a conversation. How might they do that?

Tammi Reiss: 43:53

So Tammi Reiss is spelled T-A-M-M-I-R-E-I-S-S, and you can either go to TammyReesecom or ProductLeaderCoachcom. You can connect with me on LinkedIn. I often, anytime I say something to three clients, I'll put it out on the blog. I have a newsletter on LinkedIn called Product Leadership Ponderings, and a lot of it is more just generic leadership ponderings, but I feel like that's the generic version of personalized coaching with me, because I want to help as many people as possible, and so that is my way of contributing and putting things into the ether and hoping that they get links.

Simon Kardynal: 44:33

Well, that is perfect. Thanks so much, and, of course, all of the links will be available inside the show notes that people can connect with you at any time that they need to. Thank you so much for your time today. This has been a fantastic conversation. Of course, as no surprise to me, the 40 minutes blew by, so thanks so much.

Tammi Reiss: 44:50

Thank you so much, simon, for having me, and I'm looking forward to people from the Trans Leadership Podcast connecting with me on LinkedIn and me learning more about this whole large community we're creating.

Simon Kardynal: 45:01

Thank you, Tammi. Well, take care. All right, I'm going to hit pause, yeah, hey. Well, that's a wrap from the front. In this episode, we talked about when you hit that point, that sweet spot that you've been trying to get to, and you ask yourself the question what do you do next? We talked about what you can do next. We talked about how you can do that. Next, we talked about all the different options so that you can have that honest, authentic look amongst yourself to figure out, when you end, why you want to move. Thanks for tuning in and remember leadership without passion limits the depth of your vision.

Glen: 45:39

Be sure to join us next week with your host, Simon Kardynal, for another episode of Trench Leadership: A Podcast From the Front, produced by Jennifer at, "It's a Legit Business Music provided by Ashimal of Music.

Glen: 45:54

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