Rayna Lesser Hannaway:
Uncertainty doesn't weaken trust. Pretending that there's no uncertainty does. Pretending that the way that you see your idea is the best way and the only way, that's really narrow-minded
Kristiana Corona:
Ever feel like everyone else has leadership figured out and you're just making it up as you go? I've been there. I spent two decades leading design and technology teams at Fortune 500 companies.
And for years, I looked like I had everything pulled together on the outside, but on the inside, I felt burned out, overwhelmed, and unworthy of the title leader. Then, a surprise encounter with executive coaching changed my life and dramatically improved my leadership style and my results. Now, I help others make that same shift in their leadership.
This podcast is where we do the work, building the mindset, the coaching skills, and the confidence to lead with clarity and authenticity, and to finally feel worthy to lead from the inside out
Hello, and welcome back to the Worthy to Lead podcast. I'm your host, Kristiana Corona. My guest today is someone special, a friend of mine who I met about a year ago through a LinkedIn thought leadership program called Archimedes. And I have had the distinct pleasure of reading her work and seeing her thinking throughout the past year, and I have to tell you, I'm so thrilled that she said yes to coming onto this podcast.
So one of the things that we're going to do today is pull back the curtain and hear more about what actually makes a conversation go well when you're meeting with a seasoned investor or when you're meeting with your board or the C-suite. She'll be sharing what it actually looks like from the investor side to choose a winning team to invest in and what are some of those common pitfalls that teams run into when they come in to pitch.
So one of the things that I think is really exciting about this is sort of pulling back the curtain and giving you an insider view about what investors actually look for. You're gonna learn all kinds of golden nuggets from this conversation that you can take back right away and start applying to your storytelling and your preparation and even how you operate your business.
So here's a little bit more about Rayna. Rayna spent nearly 30 years investing in small and medium-sized companies, and her career included senior investment and leadership roles at Poland Capital, Fidelity Investments, Jennison Associates, and Lord Abbott. And she has built investment teams and strategies.
She has served as a portfolio manager, and over that time, she has evaluated thousands of companies and management teams. And that experience really gave her a front-row seat into what creates confidence in a leader and what causes that confidence to disappear sometimes in the same conversation. She learned to look beyond just the presentation itself to the quality of thinking and strategy, to how well that team commanded the details, how well they were able to acknowledge uncertainty, and what happened when they had to go off script.
What did the leader do? What did the team do? Understanding those dynamics of how they interact with each other and what that says about the culture of the company and how well they align to the things that they're selling. So Rayna has an incredible perspective when it comes to all of these things that I'm excited for you to hear.
Today, she is the founder of Pure Path Ventures, and she works with investors, executives, and founders to improve the quality of their decisions and their leadership and their investment processes and even their team performance. So what she does is really a blend of coaching, strategic advisory, and also hands-on investing So with that, I won't make you wait any longer.
Let's dive into my conversation with Raina. Hi, Raina. I'm so glad you could be here today on the podcast. Thanks for making time.
Rayna Lesser Hannaway:
Thank you so much for having me. I'm excited for our conversation.
Kristiana Corona:
You and I met, uh, through Archimedes, which is such a fun program for thought leadership on LinkedIn, and I just, um, super fan of your posts.
Like, you have such interesting, incredible posts that are always so thoughtful. Um, and one of the things that you talk about a lot, which is why I really wanted to have you on this show, is you are an investor, and you've been an investor, investor for a very long time, and a buy-side analyst, and you see thousands of management teams, right?
Like you, you've seen people over decades come in, and a lot of them have prepared pitches, and you talk a lot about the importance of not only knowing what you're doing during the pitch, but what do you do in between? What do you do after? How do those conversations unfold, right? Because it's sort of the what's in between that is one of those things that, um, really makes or breaks it.
And so I, I've read so many of your posts over time, and I was like, "Okay, people need to hear this." Like, my audience really needs to hear from someone who is actually on the other side of the table and why it's important. So we're gonna dive into that today, and I can't wait to kind of have you talk through that, uh, with this audience, so welcome.
Rayna Lesser Hannaway:
Thank you.
Kristiana Corona:
You've heard a lot of pitches, and a lot of good ones, probably a lot of bad ones. But I'm curious, at a high level, when you hear these, what are you really evaluating when someone comes in?
Rayna Lesser Hannaway:
The thing that matters most to me when I'm in one of these conversations, and it's not just in an investor pitch, this could be in a boardroom, it could be in any consequential conversation where there's a great deal of uncertainty and where there might be a wide range of outcomes, I'm always just trying to figure out, can I trust this person?
And I learned this through thousands of meetings with management teams across nearly three decades as an institutional investor. But this has really followed me in every consequential conversation. What it's all about is the people behind the idea, and oftentimes when management teams are pitching or when anyone's pitching you an idea, they think it's all about the idea.
But what the people on the other side of the table are actually doing is evaluating the person or the team behind it. And so here are some of the things that, that I'm looking at. It's like, can they be honest about the weakness in their pitch, or do they have the humility to share what they don't know yet?
Can they be vulnerable enough to admit a mistake or to change their mind about something? And were they being authentic or just giving me the version they thought I wanted to hear? All of those things tell you a lot about character, and that's what I look for in any conversation. And I'm no longer an institutional investor, but I still look for those things today, whether I'm in a boardroom or evaluating an investment for the family office I work with.
Ultimately, it's can I trust this person's judgment and character, especially when things do not go to plan? Because when you think about the reality, in most wide range of outcome situations, things don't go to plan, and so you wanna make sure you feel comfortable with this person for that stage of the game.
Kristiana Corona:
Yeah. Um, I would imagine you probably see a lot of people pitching, "Here's the rosy forecast of what we think is gonna happen," but not the, "What if there's catastrophic failure?"
Rayna Lesser Hannaway:
Yeah.
Kristiana Corona:
Um, and you, you've talked a little bit about like some of the common mistakes that you see people make, and I'm curious if you could just talk about like what are some of those mistakes that, you know, leaders make when they come in and have these conversations with you, and they're trying to build this confidence in their idea or their strategy?
Rayna Lesser Hannaway:
So the most common mistake I see is just trying too hard to sell the idea. I've had a lot of teams, you know, tell me about how enormous their market is or how enthusiastic every single customer is, and you know, and every risk that you ask about, they say, "Oh, well, that's manageable." And the truth is, that doesn't make the case stronger.
You know, a lot of times I think they thought that would make the case stronger, but if someone is genuinely trying to underwrite an idea like an investor is doing, a lot of that can actually get in the way What an investor really needs to understand, or a leadership team needs to understand when their people are pitching them a great new innovative idea, is they need to understand what can go right, but they also need to understand what can go wrong and which assumptions matter the most.
And if everything is presented as a positive, it really becomes harder to separate conviction from salesmanship, and it makes it a lot harder for the people who are receiving the pitch to make a sound decision.
Kristiana Corona:
So when you think about a team that maybe did a good job of distinguishing between the good and the bad, the positive outcome and the negative outcome, like, what does it sound like when they do a good job of balancing that effectively?
Rayna Lesser Hannaway:
When they do a good job of balancing that, they show up as someone that's, you know, well prepared with the pitch, but also someone that when you take them off script, they don't lose credibility. And I think it's really important because I've seen a lot of really polished teams lose credibility as soon as we move beyond the deck.
And I've also seen less polished people build confidence because they could pause, and they could work through a difficult question honestly. And you know, what I'm watching when I'm talking to someone is I'm watching how they think. I'm seeing how they listen to questions. I'm hearing how they talk about trade-offs.
I'm looking for, you know, if they can say, "I don't know, but here's how I would find out." I'm looking to test the rigor behind the idea And so, you know, someone who really shows up credibly, like shows that they understand the assumptions, they understand the evidence, they can tell you what would cause the plan to fail.
And then with a team, there's other signals that I'm paying attention to. I'm looking for like who's allowed to answer and whether people can disagree openly. And honestly, when you think about, you know, the best laid plans, like almost nothing goes out, uh, exactly according to plan. And so when I'm able to see a team operate this way inside of a meeting, it gives me a much better sense of not just the strength of the idea, but how the team will operate when something unexpected happens, you know, how they work together.
Kristiana Corona:
I love that because I think that is the exact thing that will make or break a team over time, is can they disagree with each other? Can they debate good ideas? Can they debate challenges? Or is it you always defer to the boss? You always defer to the person who is the spokesperson, everyone fall in line, right?
Like we've both seen how that can really influence a culture in a really negative way, and especially for experts, where you got a team of experts. The whole reason why you're going to be successful is 'cause you brought in the right talent, and when you don't let them speak up and have their role and contribute ideas or solve problems, then you're just kind of dampening down the entire team, and eventually those people will, will wanna leave.
They won't wanna be part of that team. So I love that you're examining to that level of detail, even in these conversations, the dynamics of the leadership and the dynamics of the team.
Rayna Lesser Hannaway:
Yeah. I, I love hearing the way that you describe that. You know, I'm a big fan of teams, and I really believe that one plus one can equal three if you're working the right way together.
But what I've noticed mostly about teams is that oftentimes they're just a bunch of pictures on a page And there isn't the right foundation in place for people to work in that way where they can deliver Team Alpha, I would like to call it. In investing, we're always trying to deliver alpha, you know, to outperform our benchmarks.
And that can come from choosing the right ideas, but that can also come from choosing the right team. And I think that teams are a source of alpha, and it all comes down to how they work together. But people need to learn how to do that well, and then we also need to really select the right people who wanna work that way, 'cause not everybody does.
Kristiana Corona:
So when you talk about strong teams, your, your alpha teams that you're looking for, what are some of the signals that this is an alpha team? Like, what are, what are the things you look for?
Rayna Lesser Hannaway:
For me, some of the things that stand out the most is, like, whether there's a real process in place. Everyone wants to deliver great outcomes, but it's hard to do that repeatedly if there's not real process there, and if there aren't real agreements there for how the team is going to work through that process together, how they're gonna have conversations, how they're gonna challenge each other, you know, how much psychological safety i- is at the table.
Team Alpha doesn't just come from choosing a lot of great people. Because, you know, when you think about it, choosing a lot of great people often means, like, choosing a lot of high-ego people, too, and oftentimes those people don't wanna work together in that way. And so it really... You know, I go back to what I said before.
It's like you got to get the right people on the bus, and then there needs to be a real process in place and a real understanding of that process and the behaviors that drive the best outcome and, and that includes how the team behaves together.
Kristiana Corona:
I can imagine a lot of scenarios where you've got a team of very high-confidence people, because you kind of have to be high confidence to be operating in a high-risk environment like that and driving something forward purely on, you know, belief and, like, we can do this.
Uh, but what kind of dynamics make for a really great alpha team when you think about, okay, some of those people are maybe that way, but what about some of the other people? Like, are there other characteristics or other specific skills, like the analytical mind or the creative mind or the different people where you're like, "Oh, okay, I think that, that's going to make this team successful," or, "That's going to make this team special"?
Rayna Lesser Hannaway:
Yeah. I mean, there are so many things that make a team special, but the thing that stands out to me the most Is that people need to really feel comfortable speaking up and sharing what they disagree with or providing, you know, alternative perspectives. And that's often, like, where I've seen teams go wrong.
There can be, you know, a real imbalance of power on teams where people feel really uncomfortable, you know, sharing when they have a different perspective. Uh, you know, and they, they wanna just kind of follow the lead of their manager or the people that are ahead of them. And frankly, great ideas and challenges to, to ideas, they can come from anywhere.
And so it's really important for everyone on a team to feel comfortable speaking up. And with that, it's even more important that everyone else around the table gets really curious when that happens, and they lean in, and they're very open to hearing these alternative points of view. Because if that behavior doesn't exist on the team, people won't speak up.
They don't have that comfort. And so this isn't really just about being a person who's comfortable speaking up and sharing your voice and saying something that might be uncomfortable to the rest of the team. It's really about, you know, being someone who can receive that, and who instead of getting really defensive and just trying to defend your idea, actually just starts to get really curious and, like, wants to use that feedback or those questions to make their idea better or to, you know, figure out where the holes are.
'Cause we all bring a lot of bias to everything that we do, and we need to be all ears. You know, when we have smart people around us, you know, we need to listen to what they have to say.
Kristiana Corona:
I'm so glad you brought this topic up, because I think it's something that you and I both feel really strongly about, which is the idea of coaching and asking questions and being curious.
And I think you did a such a nice job of connecting the dots between, you know, how that, that psychological safety, how that curiosity, how that environment of being able to allow other voices to come into the conversation influence is directly tied to high performance and investment. And I think a lot of people think, "Oh, those are soft skills.
That's a nice to have," you know? "I'm not that kind of a leader," or, "I'll learn that later. Right now we just got yo, like, get this done." And I think it's how you work now is how you're gonna work in the future too, right? Like, you have to start embodying those characteristics of leadership and human-centered leadership from the beginning if you're gonna create the kind of culture that's going to endure in a company and be successful and not create burnout and not just send, you know, everyone packing and going somewhere else because you're terrible to work with.
But I think, like, I just, I love that direct correlation to it matters so much that it will actually directly impact whether or not you might get invested in. Like, that, that you're looking for that. I think that's beautiful.
Rayna Lesser Hannaway:
I think that's right. And look, you- A lot of folks, I think they have discomfort with uncertainty, or they feel like they need to sound really confident in everything.
But uncertainty doesn't weaken trust. Pretending that there's no uncertainty does. And pretending that, like, the way that you see your idea is the best way and the only way, that's really narrow-minded. And when we have all these smart people around us, like, we should assume that there's gaps in our thinking, and we should ask people to poke holes in our ideas.
That's really what makes an idea better, and that's the best version of a team.
Kristiana Corona:
I just want to sit with that one. I think, um, that's another topic that comes up a lot, right? The idea of intentionally challenging your ideas, intentionally challenging your thinking, and, um, how easy is it for us to get in our comfort zone or to hear enough times in a row, "You're really good at that," or, "That's your strength," or, "That idea is awesome."
And then eventually you start to believe the PR, and then you don't challenge yourself. You don't question it. You know, you don't look at, well, maybe something has changed, or maybe I don't see the full picture, or maybe this dynamic is different. It's a different team. It's a different market. It's a different economy right now, right?
Like all of those assumptions and being able to say, "We're going to sit down and create a process," to your point about the process. We're going to create a process where we are intentionally challenging our thinking consistently. And who are you inviting to the table to do that?
Rayna Lesser Hannaway:
I think that people often get the who are you inviting so wrong.
Do people like to invite people to their table who think like them and who maybe have the same backgrounds as them? And similar experiences to them. But the people that you should actually invite to the table, or who you should also invite to the table, are people who have completely different backgrounds, completely different set of experiences.
That's where you're really going to get some different answers that might help make your idea better. I'm a huge believer in diversity of thought. I think that we really need that to drive the best outcomes, and that I've seen personally just, like, how much value that I get from having people around me that truly are different.
And one of the things I, I often think about is, like, I'm 51 years old. Y- sometimes it's really great to have a bunch of 20-year-olds around the table- ... who have just a completely different set of life experiences and a different worldview, and they've grown up differently. They tend to have a lot of good feedback that I wouldn't get if I was just talking to a bunch of, you know, 50-year-olds who have had similar experiences to me.
And so I would encourage people to, like, make sure that your table includes people that are different than you
Kristiana Corona:
Yeah. Or even your kids.
Rayna Lesser Hannaway:
Yeah.
Kristiana Corona:
To your point. Um, I love that. And if you don't have those voices where, you know, go find them. Intentionally build community with people who come from different perspectives, and I think we can all find that if we look for it, but we have to realize we're in an echo chamber.
We have to realize that our environment has been curated around the things we prefer, the ideas that we believe, and, you know, what's, what's our comfort zone. And so it does kind of take stepping outside your comfort zone intentionally and realizing where the boundary of that is and inviting those other voices in.
So I love that. One of the other things that I think is very important, obviously, from an investor standpoint, is how well these teams understand the customer. So I'm curious, what gives you confidence that someone genuinely understands their customer and the problems that they're solving and the market that they're operating in, um, and, and why is that important?
Rayna Lesser Hannaway:
One of the things that I always love asking management teams, or today, you know, in conversations with companies that are telling me about what they do, is like trying to like understand better like why the customer doesn't buy their product. I think that you can learn a lot more from asking questions around that than why the customer does buy their product because it, it can tell you about what creates friction.
It can tell you, you know, who's a poor fit It can tell you what would need to change for a, a wider audience of customers to buy their products. And capturing that, you, can actually tell you a lot more than why the customers love it. I also like to ask, in that same discussion, I wanna understand, like, what the customers do today.
Like, are they using a competitor? Like, do they rely on some sort of workaround? Are they simply just, like, living with the problem? And then I'm looking for evidence. Like, are they using the product? Are they staying with it? Are they buying more? Are they, like, paying enough for the product to make the economics work?
What I've found is, you know, what customers say they want and what they'll actually change in how they do what they do or what they'll pay for are often very different. And so this whole kinda range of questions can help you figure that out.
Kristiana Corona:
And I'm sure it helps you quickly dissect between teams that have actual proof and evidence and people who are hypothesizing about, "We think this will work."
Because I'm thinking back to decades in design and product design and design thinking, and how often people say one thing and do something completely different. Like, we, we notice all the time in the research and the, the AB testing and the behavioral stuff that they may say something very favorable, very positive in a research setting.
They might be wanting to please you or they might just think, like, "Oh, yeah, that makes sense." But really, the current path that they're on is a pretty hardwired neural pathway in their brain, and you have to overcome that resistance to get them to adopt a new behavior, and there's any number of reasons why they may not adopt that new behavior.
And so until you know for sure that, yes, indeed, they will make that change, that whatever the friction is of letting go of the previous product they use or the hack that they've been using today to work around it, that the thing you have is good enough that they will actually make that shift consistently and then stick with it, not just like a quick adoption, and then I download the app, and then I never use it.
Um, yeah, I would imagine that that's really where you start to sort through the people who have real maturity in their process of acquiring customers and don't.
Rayna Lesser Hannaway:
Yeah. I think that's right, and I think that it's also really important, you know, when- You following up with maybe a company that you already have inside of your portfolio or a company that you already have as a strong partner of your business to really understand kinda where they go from here.
Because the kinds of questions that I was describing and how you articulated it from a design thinking standpoint, those things change over time. You know? And we're operating in this very dynamic environment, like, where the ground underneath us is changing quite a bit. And so these aren't the kinds of questions that are, like, a one and done.
They're the ones that you should always be asking, and where you should expect over time that the answers are going to change a little bit.
Kristiana Corona:
And so teams should really be prepared to continue answering those questions is what you're saying. So the, the ongoing conversations with your investors or your executives that maybe you answered at the beginning, that isn't the last time you're gonna be answering that question.
You're gonna continuously answer it, yeah. Um, as speaking of kinda that continuation, if you imagine someone, uh, did get invested in or, you know, was on the pathway, what is it that gives you confidence in their ability to actually deliver that work? Because I'm sure that's another aspect here. Like, one is, is it a good idea?
Is it the right team? And how do I know they're gonna deliver?
Rayna Lesser Hannaway:
Honestly, you never know whether they're going to deliver. There's a wide range of outcomes when it comes to investing, but what I try to really look for when I was underwriting an idea, underwriting a team, is that they show real command of the business.
And this goes back to what I was describing earlier. Like, I don't want a team that's trying to make every fact sound good and that is overselling me. I really wanna understand how all of the pieces fit together and where there may be some weaker links, and I wanna understand a management team's relationship with uncertainty and that they've thought through all of the things that, that could go wrong, and that they've got a good system in place for what factors they need to watch and which risks they need to really monitor for, and that they've already thought about what they would do If things start moving in a different direction.
It's about preparation because things aren't going to behave according to plan. You know, like I talked earlier about managements and what it might be like if I take them off script and I ask them questions. Like, the actual business goes off script all the time You know, even if investors can't see it, like when you actually like see how the sausage is being made, there's always things going wrong, right?
And so you wanna make sure that they've got a good handle on how to react to all of those things, and that if they don't know how to react to all of those things, that they've got the right people in place and the right process in place to make good decisions when something unexpected comes up.
Kristiana Corona:
So really, it's your, your job to role play the various scenarios of what could be, whether they're good scenarios or difficult scenarios, and have they thought it through from every angle?
Have they come up with their mental models for how they think about handling situations like this, or is this the first time they're thinking about it? Yeah. So, so if teams are trying to prepare in advance and really be ready for a conversation like this, it sounds like them sitting down and imagining all the potential scenarios, what could happen, and figuring out how they would respond to those would be a very useful, uh, exercise.
Rayna Lesser Hannaway:
Yeah. But if they aren't doing that, there's not enough rigor behind the idea. You know? And so, like you shouldn't even be having conversations with investors until you've looked at it from every angle and really held yourself accountable to kinda surrounding that idea and looking at everything that could go right and everything that could go wrong. Otherwise, it's gonna be pretty hard to sell the idea.
Kristiana Corona:
You have kind of a strategy, I think, for your criteria, your evaluation criteria, and you've talked about that being across three different categories: the story, the substance, and the signals. So I'm wondering if you can just quickly take us through those three criteria and, you know, how they all work together to build trust.
Rayna Lesser Hannaway:
So I'm gonna keep it really simple. The story is what helps me understand the idea, and that like goes back to this pretty pitch deck, you know, that everyone's, you know, practicing a whole lot to deliver. But the substance really tells me about whether it holds up, and this is like when I take people off script and I'm asking a lot of questions and I'm seeing how they think out loud.
I'm seeing like how much rigor there is behind the idea. I'm really starting to see like wwhether, you know, that humility is there, that vulnerability is there. And then, the signals is really like, that's what tells me, you know, whether I can trust the people And so it's not just about, like, the problem behind the idea and why it matters and why now.
It's really the evidence underneath it. And as an investor, the evidence is really, like, the economics, the assumptions, the, the trade-offs, the plans for execution, and I've seen so many great visions without great execution. We should slow down on that point. But you- the signals is... That's what happens in the room.
Like, can they answer directly? Can they admit that there's a gap in their thinking? When there's a team, like, uh, is everyone contributing to the conversation? I saw mismatches with these things all the time, and it's very telling inside of a meeting if a company kinda doesn't stand out on all of these levels.
Kristiana Corona:
Do you have an example of a, a story like that where you, you saw someone give a fantastic pitch, but then when it came to, you know, how they'd roll it out, it just wasn't quite there?
Rayna Lesser Hannaway:
I've seen that more times than I can count. Yeah, you know, frankly, like, you know, when you're investing in companies, and I invested in public companies that were, were small cap, things go wrong all the time.
And so it's less about that first meeting and, and, like, what they, like, could or, or kinda couldn't hold up to, and more about what happens over time. But what I would say about those pitches, like, inside of those meetings, I, I did see a lot of mismatches that I think your audience would really benefit from.
So I had companies all the time talk about having a collaborative culture. But then, you know, with, like, the CEO and the CFO and the investor relations person there, like, the CEO wouldn't let anyone else answer the questions. So there, like, it, it kind of brings the lack of collaboration to life- ... right in front of you.
Kristiana Corona:
Wow.
Rayna Lesser Hannaway:
I would have a team tell me, like, how focused they are on the customer and really emphasize that that's their competitive advantage. But then when I would, like, ask them all these questions about the customers and why they were leaving, nobody had any good answers. So they weren't actually close enough to the customer to know And so, we've gotta be really careful that, like, how we pitch, how we describe ourselves, and our actual kind of behaviors in the room, that those things really match up.
You know? And it all comes back to trust again, where we started. Trust really grows, like, when the story, the substance, the behavior, they all support one another. And when they don't, people notice. That's when your pitch falls flat.
Kristiana Corona:
Yeah, like really having a sense of alignment between what you say and what you do.
I mean, which sounds so simple and basic to the rest of us. It's like this, uh... Like, what is it? A common, uh, human rule we all try and live by, but how often do we get it wrong? You know, how often do we say something 'cause we think it sounds good, and then we don't do the exact thing that we talk about?
It's surface level. It's not really as deep as it needs to be, or it's not really ingrained in our DNA. When we say we're customer-obsessed, like we said customer-obsessed all the time when I worked at Amazon. That's a leadership principle. And so there were very specific behaviors that were defined behind what that meant to say. You couldn't just say, "Yeah, I'm really obsessed with customers."
Like, you had to show up in a certain way and deliver a certain set of behaviors in order to say, a- authentically, "I can say that I am customer-obsessed." And I, I love that, because kind of setting that rigor to say, "Well, you say that you are, but what does that actually mean? And how do you make sure that everyone is?"
So that that is a consistent ethos throughout the company. One other thing that I'm very curious about is, you know, so we've talked a little bit about, uh, what's important, what they might forget, or, you know, what do they need to make sure they include. Um, how else can they understand what you need as the investor, um, and your thinking and...
Now that we have you here what else should they be thinking about?
Rayna Lesser Hannaway:
So in an investment context, and even outside of an investment context, I think what's really important is to think about the people that you're pitching to and the decision that they need to make. Because a lot of times when a management team is preparing to give a presentation, they think more about the presentation that they want to give, but they're not thinking that much about what the person on the other side of the table needs.
They're not thinking about what success would look like to them They're not thinking about how their company might be competing for the exact same money, time, or attention They're not thinking about the kinds of, of risks that the investor needs to underwrite and what could go wrong for the investor if the decision goes badly. And, you know, the same idea can look really different depending on where you sit.
And so you really need to think about every position at that table and what matters to them. And so if you're talking to an investor, they're really gonna care about Not just the company, but they're trying to figure out, you know, what the return profile looks like. They're thinking about valuation.
They're thinking about the expectations that a management team is setting. You know, they're thinking a lot about the risks and what could go wrong and, and what their downside is. You- then, like, if you were talking to a board, for example, trying to, to pitch an, an idea, they're thinking more about the strategy, and the risk, and whether management or the, the team that is pitching them can execute.
You know, an operating leader might be focused on, like, "Oh, this is, like, a really interesting idea, but what other thing that we're doing here, what other project is this going to displace?" And so pitching someone isn't about telling them what they want to hear. It's about making your case relevant to the decisions that they actually face.
Kristiana Corona:
I think a lot of us could benefit from remembering that there's a human on the other side of this equation, and that human has certain job expectations, job pressures, competing priorities, stretched too thin. Um, you know, all of those types of things are happening on the other side of the table. It's not just you on one side of the table and a bank on the other side, right?
And so when you put the human element in there and you think about putting on the hat of an investor or putting a hat on the hat of your board, I think it does bring to life so many more interesting opportunities for how you could frame up the things that you're saying in a way that really connects with the person on the other side of the table, and respects your expertise and your constraints and why this might be a risk for you, and how it is their job to make sure they de-risk it, um, as much as possible and bring you something that feels like a yes, that feels like this is a safe bet or this is a something I'd feel proud to invest in versus someone who's trying to manipulate or trying to get a certain outcome for themselves.
And I mean, I think that comes back to authenticity as well. Like, you need to be coming from an authentic place where you feel like you really can deliver the thing that you're selling and do it well. But again, I just think all the time that we imagine spending time selling at someone or presenting at someone versus imagining being on the other side of that table and receiving our pitch or our conversation, how would that feel?
How would that feel for them? And having that empathy makes a real difference, right?
Rayna Lesser Hannaway:
It does make a real difference. And the best advice I have, you know, in any kind of situation like this is to be really clear about what must be true, how will we know, what will we do if it's not? There's so many assumptions behind every idea.
And so being able to really state those assumptions clearly is important to, like, having your idea land with the folks on the other side of the table, and being able to show which ones matter the most, what evidence would tell you that they're right or they're wrong. Those are important things to articulate before the results arrive.
Kristiana Corona:
I'm so thankful for you coming in and, and having this conversation, and I just wanna offer up, like, if people want to follow your work or connect with you, where can they go to find you?
Rayna Lesser Hannaway:
The best place to find me is on LinkedIn, Rayna Lesser Hannaway, or you can go to my company's website, purepathventures.com.
I would be thrilled to, to have some conversations with your audience. And just so everyone understands what I'm focused on today is I really spend my time at the intersection of investing and advising. While I don't serve as an institutional investor anymore today, uh, I'm working very closely with a lot of investors, and that can be from, you know, helping people get clearer about something, you know, helping investors level up.
It can be about just being a trusted advisor and a, a sharp thinking partner in the room to senior leaders or investors that are making high-stakes decisions. It can be in the boardroom. And I also take on a small number of fractional engagements, so working with family offices or working with wealth management firms that maybe don't wanna make a full-time investment hire but need a senior investor.
Kristiana Corona:
So as you probably could tell from this conversation, Rayna has an immense amount of expertise in this area, so anyone who can get a minute of your time, it will be well worth it. Yeah. Thank you so much. This was such a lovely conversation. I feel like I have probably 100 more questions, but maybe we'll, we'll have to get you back on the show another time, uh, after, after I hear all the questions that we didn't get to answer today. This was so great.
Rayna Lesser Hannaway:
Thank you so much, Kristiana. And, you know, if I could leave everything with just, like, one thing that they can remember coming out of this is that when you're pitching your idea, bring your thinking into the room You know, people aren't... They're not only judging your pitch, they're judging you. How you reached it, and what you understand, and how you'll respond if the facts change.
Kristiana Corona:
I love it. Thank you.
Rayna Lesser Hannaway:
Thank you.
Kristiana Corona:
I hope you enjoyed this episode with Rayna and are taking some good golden nuggets away for your next big pitch. Some of the things that I really enjoyed about this conversation were the focus on acknowledging uncertainty and not trying to paint too rosy a picture, but really acknowledging that the strength of a team comes from how you handle challenges, how you handle the unexpected, how you prepare in advance for things that don't go well.
And the way that you show up with your team and acknowledge their expertise and share the stage. That can also be a really important factor in, you know, psychological safety, and trust, and really saying, you know, "Is this team going to last? Does the leader respect the people on the team, or are they taking the mic the entire time?"
So all of these little clues, right? That can make or break an investment decision. I also loved the conversation about how well do you know your customer, and can you defend both how you get customers and why they stay, and also why they leave. It's really important to think about both sides of the coin.
So I'm really curious from your perspective, what was the biggest takeaway that you had? Go ahead and leave that in the comments. I'd love to hear. If you enjoyed this podcast, go ahead and subscribe so you never miss another episode. You can subscribe at worthytolead.co/subscribe. And as always, keep showing up, keep doing the work that matters, and keep leading like you're worthy to lead. Because you are. Bye for now.
