Leading with Confidence: ‘How I Work’ EP33 with Ramona Shaw

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Ramona Shaw has leadership and executive coaching expertise and is a former VP of a global private equity firm; she leverages her experience to help new managers become leaders. In addition, she is a best-selling author and podcast host and has developed a 12-week curriculum on the foundations of leadership.

How I Work, Episode 33 with Ramona Shaw (Ramona Shaw LLC)

Ramona and Josh dive into the foundations of leadership and confidence. She shares how believing in each other and delegation are key attributes of an environment that fosters confidence and how leadership responsibilities shift as your company evolves and grows. Plus:

  • The risk of overconfidence: Looking at confidence as a spectrum
  • Practicing stoic leadership
  • The cost of not having company values – confusion, lack of trust, and misalignment

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Transcription: How I Work, Episode 33 (Ramona Shaw LLC)

Josh: Hi everybody. Welcome to this episode of How I Work. I am so excited to introduce my guest today, Ramona Shaw. Ramona helps new managers become leaders. People love to work for through leadership and executive coaching. She’s developed 12 week curriculum focused on the foundations of leadership. Is the host of The Manager Track podcast and author of The Confident & Competent New Manager: How to Rapidly Rise to Success in Your New Leadership Role. Thanks so much for joining me today, Ramona.

Romana Shaw: Thanks for having me, Josh. Great to be on radio.

Josh: It’s awesome. I love the title of your book, have confidence is [unintelligible 00:00:42] tagline. I want to just dive right in and talk about confidence with you.

Romana: Let’s do it.

Josh: You’ve obviously done a lot of work in this area. You’ve got this great book about The Confident & Competent New Manager. What are some of the personal attributes or attributes of professional environment that might foster confidence?

Romana: Actually maybe also to just set the stage a little bit in terms of the confidence, especially for new managers or for leaders. There’s something to be said about having a great deal of confidence, but also there’s something to be said about having doubts and being doubtful. Because I think we sometimes and even like the book title says, how do you become more confident. There’s also the risk of being overconfident.

For new managers this is the way it plays out, and actually totally guilty myself, where I thought in my first leadership role or before entering it, well, I am successful as an IC. I can deliver, I can perform, I’m doing this well and I will be fine. This is just now leading other people and teaching them or working with them and–

Josh: Can’t be that hard?

Romana: Yes, can’t be that hard, right?

Josh: Right.

Romana: This is when we start to not pay attention to the fact that this is a huge transition. Actually anytime that we’re taking on a big new responsibility, a big new role, a big new project, things that we’ve never done before, it’s good to have some doubts play in the back of your mind.

Because it will make you more aware, it will make you be keen to double check or look up things or learn things or listen to other people and listen for guidance or engage a mentor or a coach versus if you think, no I got this. Because that will make us a little bit blind. For me personally, I definitely had this sense of overconfidence and this is something I see with new managers all the time.

Where they start the role, they think it’s going to be okay, it can’t be that hard. Then sooner or later they run into these situations where they think wait a second. That’s why we’re there. Why is this not working? Why aren’t they doing what I tell them to do and why aren’t they not hearing what I’m saying? Why is this hard?

These are the moments when it then comes head-to-head and oftentimes we wished or they then wished like maybe I should have gotten a coach or should have done some leadership training earlier on I could have maybe prevented some of this from happening. I want to say that upfront as like confidence, looking at it as a spectrum. We’re not aiming for overconfidence, we’re not aiming for constantly running into self-doubt. We’re really looking for this healthy level of confidence.

Josh: Also [unintelligible 00:03:37] doubt, right?

Romana: Yes, right. I think the doubts will also elevate our self-awareness. Because it makes us look inward. Then when we want to cultivate to go back to long-winded here, but go back to your question about how do we cultivate an environment of confidence? So much of this is believing in other people. Not just believing them and keeping it to ourselves, but believing in them and letting them know.

Trusting them, telling them, hey, even if things goes south, I got your back. I believe you can figure this out and if not you’ll definitely learn something from this and it will be to your benefit. Figuring out where is that limit for the person that you’re leading and how do I push that limit up by believing in them more than they may believe in themselves.

Josh: I know that when I talk to managers, I tell them that I think managing people is the second hardest thing in the world to do. The first hardest thing is being a parent, because you can’t fire your kids, but it’s just about the same thing. It’s like you have to be able to give them a little bit of latitude to make mistakes. You got to have some faith in them that they are going to be able to take what you’ve taught them or what they know and apply it effectively. You can’t just be on top of them at all times. I would say that going from and being an IC to managing people that’s a big shift and I don’t think people are necessarily ready for it or understand how big of a shift it is, for sure.

Romana: It’s just like you highlight, I think it’s for many people the biggest or one of the biggest transitions that they make in their careers. Because it’s not just a different responsibility, it is a complete flip in their mindset. The things that make them successful as an individual contributors, an IC, are often the things that keep them stuck as a leader. Like in my personal case, being the person who gets stuff done is great as an IC and then you start leading people and all of a sudden that becomes the big thing that gets in the way of me being effective.

Josh: Now, all of a sudden, delegation is more important than you actually getting stuff done and being able to understand the skills and abilities on your team and be able to delegate the right things to the right people that will feel challenging to them, but not too far out of reach for them.

I think that there is something to being able to understand. There may be a few things that as a leader or manager I’m going to have to do myself, but more importantly, it is about figuring out what is it that my people can do and then pairing that with the opportunities that exist that will help them grow in their career and challenge them in their work.

Romana: 100%. I’m going to tie this back into confidence too, because when someone who likes to get stuff done or has this sense of being seen as the go-to person and then all of a sudden I find, even if I did delegate work to someone else, I find myself in a situation where I realize they’re taking too long, it’s not good enough. I might have the urge to jump in, it’s what we call being the superhero. Jumping in, solving the situation and then jumping back out. Whenever a superhero is applied, there’s also a victim standing right there. The victim in that case then is my direct report. Because the indirect message I just sent is, “You weren’t fast enough, it wasn’t good enough, I didn’t believe that you were able to solve it and that you were able to rescue the situation.”

I needed a superhero to come in and that was me. They will not feel confident after this experience. In fact, they probably will feel less confident going forward. Because they realized, oops boss had to have been to get that over the finish line. Versus if instead I took more of I called it the Yoda standpoint, the Yoda approach where I help them think through the problem. I guide them from the sidelines so that they get out of the experience feeling like I did that. I learned how to do this, I figured this out. I had a critical part in overcoming the challenge and so now I feel more confident that going forward I can handle things like this.

Josh: I’ve been talking about this confidence framework for digital marketers and one of the foundational pieces to that is creating a learning environment like a learning organization. Getting everybody to have this shared mindset that we might try things and we might fail, but that’s okay because there’s failure in data, so it’s only bad to fail if you don’t take the next step, which is to say, what did we learn and then how can we apply those learnings to the next thing that we’re going to go out and try to do as a marketer? I love that you talk about doubt as being something that’s super important when it comes to confidence.

Like I equate that to in my thinking too, like becoming a learning organization we need to be learning organizations. Anything else about how you think leaders leverage doubt to their benefit?

Romana: I think with doubt it goes a little bit hand in hand with curiosity. I don’t know if it one enables the other, but it definitely often comes together where confidence may go more or this sense of overconfidence may be more tied to ignorance. The curiosity at the end of it’s a meta skill that’s immensely helpful in any professional setting, like marketing as well, but specifically leadership where we start to be curious of “Interesting. How did that go? How could I have done this better? What is required of me going forward? What might have caused this one person to say what they said or do what they did that was unexpected to me,” or they seem disengaged, especially in the hybrid remote world where sometimes we start to pick up on little things, can’t really put it all together in the big picture yet, but just little small odd stuff seems to happen.

When we are curious and we can talk about it and say, “This is not a judgment. I’m just curious of what happened here, or what made you think about it that way. I want to understand.” Sometimes the doubts start us to or get us into that mode of curiosity which is tremendously helpful.

Josh: I love that. You mentioned like how our workplaces have changed and our hybrid and things like that and I know that you’ve had a lot of experience with different size companies. One of the things that we’ve talked about a little bit is how you lead people when it’s an early-stage company and there’s only maybe a handful of people in the company versus what that looks like as the company grows or changes, and the organizational structure grows. How does the way that we need to lead change when we go from startup to real grownup company?

Ramona: I was born and raised in Europe, Switzerland specifically. As we’re speaking now, it’s the World Cup. It made me think of soccer right now. When we’re thinking about a soccer player, we see them on the field and they’re kicking a ball forth and back. We don’t see them lifting dumbbells or squatting or being on or doing some cardio on a machine, but that’s what they do in order to prepare for the performance. When we’re thinking about a small team– Now I live in the Bay Area in San Francisco and work with a lot of startups who are in that phase of founding team, a few people, they get along, they’re friends, or they all work together somewhat in a flat hierarchy and all of a sudden they get funding and they scale really fast.

Now at that time, or leading up to, actually, you want to ideally do this a little bit ahead of time before you scale, is to think about what are the muscles I need to train at the gym in order to then be prepared to perform while I’m on the field? The muscles that we need to train as leaders in order to prepare for scaling that will then really come to show as the company grows, those are the things such as having a really solid understanding of what are our values and our principles. It’s easy to forget about those because they’re talking about are built-in or natural in a small team, but the moment you start to hire and hire at scale, you quickly notice that you don’t know what you’re hiring for if you’re not clear on your values.

You don’t know how to tell people or evaluate if a leader that you hire in from the outside matches your leadership philosophy if you don’t have a leadership philosophy. What do you stand for? What do you not stand for? What do you expect of the leaders in the company? That has to be defined and it needs to be communicated. Then flow into the hiring processes, the onboarding processes, the performance review process, and all of that so that everyone’s on the same page. That’s one aspect. Then the second part is what are the systems, and I refer to this as, I talk about this in the book, developing your leadership system. This is your method of how do you lead, what are the routines, and the behaviors and practices you put in place?

In a marketing world, you may say, “Hey, every Monday or every Friday we look at this dashboard. This is how we evaluate what’s going wrong, what’s not working, and what do we need to tweak next week where we define our game plan based on that.” The practice of looking at the end of the day, looking at your dashboard, or Friday as you look at your dashboard, that’s part of your system and how you manage a campaign, for example. In leadership you would look at how do I hire onboard and then manage people on my team from the beginning to the end in a way that’s thought out and somewhat methodical in terms of here is the performance review cycles that we have.

Here we all have one-on-one meetings, or I as a leader choose to have one-on-one meetings. here are the career conversations we want to put in place. Here’s how we do goal setting. Here is how I think about stakeholder management. Here is how I communicate and create transparency from the top to top down in terms of having team meetings are all hands. The cadence of these meetings, the tools that you use, the frameworks that flow into a system. In the beginning, it’s a little scrappy and everyone does it their way and you learn on the job and then you start to get to the moment where it’s like, “Let’s build the backbone. Let’s go back to the gym. It’s off-season. Let’s prepare and build up so that we have that, those resources in place, and then are ready to run.”

Josh: I love that. I do think that a lot of it does have to do with values and understanding very clearly what those are, articulating what those are, and then living, living by them. That they shouldn’t just be these big broad statements. We should be able to define them in such a way that we can teach them, that we can review people based on them, that we can hold people accountable to them. Anyway, I love that you start with it’s all about a company, figuring out what its values are and then the transmission of those things through a system is what grownup companies do that maybe a startup company doesn’t have to do because, hey, we’re all buddies. We know each other’s values because we like each other and we’re the same. Right?

Ramona: Totally. It’s funny even when I hear myself talk about it, there’s definitely the inner tension in me is like, if I was a leader in a startup, I feel like, “Oh, my gosh, we don’t have time for this.” My mind is performance-based. I think about, “No, that’s going to slow us down.” It’s all nice work, but, really, worst of revenue, that’s what matters, but then in my work, I see this day in and day out how the cost down the road of not having done that tremendous. It’s confusing for employees, lack of trust in leadership, wrong hires because there was misalignment and miscommunication. It’s higher retention rates than needed because we hire people that aren’t a good fit in general, a lack of consistency in terms of how teams are evaluated. That then creates demotivation and disengagement. It has this spiral effect down the road. As much as it seems like an unnecessary task to do this is like we said, like, “No, there’s a reason why all grownup companies do this.”

Josh: I’m like in all vulnerability. [unintelligible 00:17:50] is on this journey. We’re still quite a pretty young company. It started with a group of people who know each other really, really well. Now, as a 30-person company, we’ve I think done a pretty good job at defining what our values are and trying to transmit those values and articulate them in good ways, but it’s a journey.

I think you’re right if you don’t do it right, you start to see those things around like employee churn and you start seeing those things around like trust. It is not an easy thing. It is not an easy thing to do, but I wholeheartedly believe it’s worth it. I think a lot of the listeners here are like, “Software is a service business.” That’s all about what’s our monthly reoccurring revenue. What’s our annual reoccurring revenue? That’s all that they’re focused on and care about. Let’s just drive that number up. I do think that this work, this leadership work is just as important especially if you start seeing success and you start scaling.

Ramona: Exactly. I think it’s then who does the execution of the very tactical things. Then who in the organization is thinking about the cultural aspect or thinking about the leadership competencies and the values? I love that you’re saying we’re on this journey too. I think sometimes we say you’ve got to have it right, but actually no. Even if you do it scrappy, do it. We don’t need to make it a big deal. You don’t need to hire consultants for $100,000 to get a culture plan in place. No. Just grab a document. Write down, set up culture surveys. This can be super simple, five minutes. Consolidate it, write a one-pager and then use that and iterate with that in mind. Just as you do everything else, and it’s scrappy, not you, but as companies scale or build or grow more so things can be scrappy. This one can also start with a scrappy draft and then go from there.

Josh: I think the word you said, iterate, is probably the most important word. It goes back to what we were talking about before we started recording, which is just to try your best, do the best that you can right now, and then iterate-

Ramona: Then iterate.

Josh: I think that’s super important just philosophically. Again, it goes back to being a learning organization, of course.

Ramona: Totally.

Josh: I want to shift gears because I know that you have a big interest in stoicism and we’re getting on the edges of some of that. I think you’re starting to write a book or writing a book about leaders who practice stoicism. I’m just interested and curious about that. Can you first define what that is for the audience, and then second, tell us how you’re connecting the dots between stoicism and leadership?

Ramona: Yes, so stoicism had its origins in the Roman Empire and I think, Marcus Aurelius is probably the most common or well-known stoic leader. Then it had a bit of a modern revival. Tim Ferriss is often stated as the person who introduced people to stoicism. There’s also Ryan Holiday who wrote many books on the topic. I first started being interested in the philosophy of stoicism as a philosophy of life that’s very tactical or practical better.

It’s not about philosophing and thinking about life and contemplating what’s a good life. It’s really about how do I live by these virtues or values, as we would call them today, by these stoic values? What does that mean to me, and how does that specifically show up in my day-to-day interactions with people, what I base my decision on, how I set up my life, and who I really want to be?

For me, personally, stoicism just really resonated as a philosophy that talks about being a good human, but also, and what’s often overlooked is really being caring and looking at community and being of support to the community and influencing people in a good way and doing the right thing, not doing the easy thing, investing in gathering knowledge and increasing our level of wisdom over our lifetime and so forth.

I was really interested in it. As I was personally building that interest in the knowledge on stoicism, I also built and continue to develop my knowledge in the leadership development space. It occurred to me over and over how the things that we teach when it comes to leadership development can directly be traced back to stoic philosophy and to things that these wise men at the time or women have said, and that we can read in books that were written or captured or based on words spoken thousands of years ago.

We now package them into being like, “This is the new thing, it’s vulnerability, or it’s the five this and five that.” I thought, we don’t actually talk about stoicism as a philosophy for leadership at all. In fact, when I first started socializing this idea of writing about stoic leadership people would always say, don’t do that. Stoic leadership is not an attribute people want to be associated with, it’s not going to sell, no one wants to read it. That made me want to write it even more. It’s like, “Oh, for sure I got to write it, and for sure I’m going to call it stoic leadership.” [chuckles]

Josh: Yes.

Ramona: I interviewed about 20 leaders who are in corporate roles or in leadership roles who are practicing stoicism and see the intersection and the benefits of stoicism and how that’s helping them, especially during a time where resilience is a big topic where a lot of things seem out of our control and working with that. I’m in the writing process. I’m excited to bring that to light in 2023.

Josh: Wow. That’s cool. I imagine those interviews were amazing.

Ramona: Yes, surreal.

Josh: Hopefully, you’ll get some excerpts from those in the book and I look forward to seeing it. You mentioned Tim Ferriss and a few others. One of the things that I ask as a final question here, and I’ve really appreciated this conversation, it’s been great, is ask all my guests who are you listening to or reading, who’s challenging some of your assumptions or inspiring you today? Can you give us names of a few authors or thought leaders or podcasters that you’re like, “Oh, everybody should be listening to this person right now”?

Ramona: Oh, gosh, there’re a lot. I think the most consistent person that I look to in terms of my own development is Marcus Aurelio. Maybe not a surprise on that front. The people that I listen to now, I like John Maxwell. I think the books that he wrote, the work that he puts out in his consistency in his messaging over the years, it’s really impressive, and the impact he’s had in the different fields that he’s working in.

I also, like– if I think about leadership specifically or scaling, I have to think about a few other people. Oh, so, okay. Adam Grant would be another one that I definitely follow and listen to. I like his research-backed approach. The only time I don’t listen to Adam Graham is when he talks about imposter syndrome, but everything else. [laughs]

Josh: Right. You got to know when the tune in and when the tune out.

Ramona: Yes, exactly. There we are on a very opposing views on that. These will probably be the people that I follow the most or most consistently.

Josh: Okay. Awesome. Well, like I said, this was a super fun conversation. Really excited to read that book about stoic leadership. Keep working on that and let us know when it comes out. I really thank you for being my guest today on How I Work. Thanks, Ramona.

Ramona: Thank you so much for having me.

[00:26:06] [END OF AUDIO]


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