TLDR;
What if the key to being a great leader isn’t about working harder, but about being more you?
Hi, I am Michael Hunter, founder of Uncommon Teams, and I’m so glad you found this episode of the Uncommon Leadership Podcast. Because today, I sit down with Jason Dea, who is a CPO, a startup advisor, and a leadership coach, and explore a new way to lead.
Discover why trying to be a different person in different contexts is exhausting and how being your authentic self can be your greatest strength.
Join us as we also talk about the art of turning big, overwhelming problems into manageable baby steps, and why focusing on the process—not just the outcome—is the most reliable path to success.
Grab a set and let’s together explore a new way to lead with ease, purpose, and confidence.
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3 Reasons Why This Podcast Is Your Next Must-Listen:
- If you’re willing to re-examine your role as a leader/ founder/ CEO—
Discover how an obsession with process and a mastery of team dynamics can be the true drivers of sustainable business growth. - If you want to tackle your biggest business challenges head-on—
Learn how to turn overwhelming challenges into a series of tiny, manageable experiments that build momentum and confidence. - If you want to truly build an incredible workplace culture—
Get ready to build a resilient, adaptable organizational culture where authenticity and psychological safety are not just buzzwords, but the foundations for a powerful and lasting legacy.
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While others are bogged down by miscommunication and a constant sense of overwhelm, the most resilient leaders are operating with an uncommon advantage.
The question is: Are you ready to stop guessing and start leading with purpose?
If yes, let’s talk: https://www.linkedin.com/in/humbugreality/
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Meet the Speakers
Jason Dea
CPO @Koru | VP of Product | Startup Advisor & Coach| Helping Seed to C SaaS startups find PMF and scale to predictable growth
Hi, this is Jason Dea. Here’s something you should know about me:
For over 20 years, I’ve navigated the startup world—from an idea on a napkin to successful exits. I’ve lived the grind: balancing vision with execution and scaling without breaking. My passion is helping founders cut through the noise and turn their ambitious product visions into scalable realities.
I specialize in AI-driven product strategy, helping teams align their roadmap and drive growth. I’ve been in your shoes, scaling SaaS products to millions in ARR and through multiple successful exits.
Michael Hunter
Founder @Uncommon Change | Interlocutor / Curious Host @UncommonLeadership Interview Series | Author | Change & Innovation Partner
I’m Michael Hunter, the founder of Uncommon Teams. All my work is driven by a single mission: to help leaders, CXOs, and founders build uncommon teams.
These are the teams where every person feels valued, psychologically safe, and confident to bring their authentic selves to work.
Drawing from my experience with leaders across six continents, I’ve developed a battle-tested framework that is always precisely customized for you, helping you greet change like an old friend.
My deepest satisfaction comes from helping leaders not just envision their legacy, but truly inhabit it. By integrating your whole self into everything you do, you can discover ease, freedom, and a resilient leadership journey that creates a safe organizational culture for everyone.
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Presented By: UncommonChange
Transcript:
Michael Hunter
Whether you want more innovation, more easily, you’re feeling burnt out or overwhelmed, or you simply know that something isn’t quite the way you know it can be. You are not alone. I hear the same from leaders every day. On Uncommon Leadership, we explore aligning personal fulfillment with business success, creating authentic teams, and cultivating the resilience, adaptability, and ease necessary to move beyond simply surviving today’s challenges into thriving.
I’m Michael Hunter with Uncommon Teams, and today we’ll uncover fresh insights into what it means to lead today. And joining me is Jason Dea. Jason has spent the last 20 years in software startups at various stages, from an idea on a napkin between friends to series A and B scale.
He has been a part of a few exits and a failure along the way. Now he’s found his niche in product leadership, traveling through sales and marketing to get there. Welcome, Jason.
Jason Dea
Thanks, Michael. It’s a pleasure to be here.
Michael
When did you first recognize that integrating your whole selves, bringing that into everything that you do, might be a valuable approach?
Jason
It may be kind of cliche, but I think the older that I’ve gotten, the less, time and energy and sort of mental resources I set aside to try to separate myself into different people when it, depends on the context, whether that’s a, professional version of Jason, a family man version of Jason, a social version of Jason.
At the end of the day, I’m the same person, I have the same kind of characteristics, qualities, some of the same traits, obviously some of the same weaknesses. So, perhaps out of efficiency, the older I’ve got, and I’ve learned that, it’s probably best to apply the same person, regardless of circumstance, and just tackle the challenges or the opportunities, within the context of when they happen.
Michael
How have you sussed out as you’re combining all those different Jasons into the one Jason? Which of those different aspects of you that had shown up perhaps differently in different contexts were all actually you, and which may have been not quite Jason or things other people said, Jason should be, and Jason really isn’t?
Jason
Well, I guess, maybe I’ll answer that question with a sort of an example, something that I’ve learned is a trait that has benefited me well, regardless of circumstance. Let’s specifically talk about professional versus personal, is I tend to be fairly patient or appropriately patient.
And I think I’ve gotten to that place in my life. Really, because of a combination of learnings of professional successes and professional failures, but more importantly, personal circumstances. And, having gone through personal joy and, sadly, a lot of personal, kind of, bad experiences, getting to an age where I’ve seen friends pass away, family pass away, had various types of urgencies and emergencies, with my own family. And it gives me, you, gives me and gives, you, when you go through that, a different view of how you, kind of tier stress and how you, the context at which you look through, stress and difficulty and things like that.
And when you look at things more evenly across the same, through the same lens, I’ve just found that gives me a better perspective on how I approach everything, whether that’s something as mundane as what to eat for dinner or, perhaps, a big project that I’m working on at work by having kind of that universal lens with, sort of colored by my life experience across the board. It’s given me just a more even-keeled view of things and how that’s manifested professionally. And, as a parent, for example, it’s just a fair degree of patience, which is not a specifically professional trait or not a specifically kind of family personal trait.
It’s just one of those universal things that I think can benefit across the board. And that’s probably a relatable example, at least, something specific. But I try to. I’ve come to a place where I take the same view from multiple elements of my life.
Michael
So, would it be fair to say then that you’ve been observing how you act in all these different contexts and how those different actions feel, and you’ve been using that to navigate through and pick apart?
This is Jason. This isn’t quite Jason, needs to adjust this way. This isn’t Jason at all. Kick it out of here.
Jason
I think that’s a good way to put it. Probably a more elegant way to put it is, regardless of the context, be it professional or personal, I have the same motivations, I have the same priorities, and for the most part, I have a similar pattern of how I think through, or the logic that I apply to a situation or a challenge.
So it’s kind of unnecessary overhead to have two different models of operating, is what I’ve come to learn. And it, at least to date, seems to have benefited me well.
Michael
As we’re bringing our whole self, same self, into all these different contexts, they’re also different contexts and sometimes require a slightly different approach. For example, maybe I talk to my dog a little differently than I talk to my 2-year-old, versus a 20-year-old, versus my parents. How do you know that you’re staying true to yourself while also adjusting the way you show up to best help the context you’re entering into shift in the way that you hope it will shift?
Jason
That’s a great question, and it helps me maybe center my thought a little bit more or elaborate is I’ll extend your scenario one step further.
So you mentioned, a dog, a couple family members, so on and so forth. Let’s extend that to maybe a coworker or somebody that I’m speaking to at work. And I think, again, behind the scenes, I’ve developed a way to think prioritization, and kind of approach the things and so on and so forth.
But, kind of before I say anything, to your point, it is important to take a step back and listen. And then again, a universal muscle, if you will, that I’ve tried to build is understanding my audience. So, regardless of my logic behind the scenes, regardless of what I feel is important and the way that I prioritize things behind the scenes, one of the things that I do recognize is important is, in most contexts, I won’t go so far as to say in all contexts, but I, believe in most contexts, one of the things that is important is to be able to have a clarity and ease of understanding of the points that you’re trying to get across. Whether that’s getting my son to clean his room, convincing my wife that we should go to a certain restaurant for dinner, or relaying something important to a coworker.
It’s important to understand the audience specifically. And, with regards to an audience, maybe there’s a search, style, or format, or cadence in which they like to be communicated in. When it comes to the specifics of the point that you’re trying to grid across the message that you’re trying to get across, obviously, it forces me, right now is a great example to think through what are the primary points that I want to get across. That I want to relay through the appropriate channel or the appropriate format. So I think, again, more of a kind of a broad skill that, you know, I don’t profess to be an expert in, but a skill that I try to honed in, whenever I can is, taking that moment to take a breath and understand the kind of the context of listening or the context of understanding, or experience that your audience would appreciate that would work best to relay your message.
Michael
How do you choose how much to customize your message in the way you are to each individual person you’re talking to, versus doing this the way that works best for you and hoping that they can get enough of what’s you’re trying to say, that they get the point?
Jason
Well, I think there’s two things on my side. There is an implication that I myself have a sense of a concise version of the point. Once I develop that or have a reasonable understanding of that, then there’s a few different dimensions of how, as I know or I get to know the different audiences that I speak to, how they best can digest that, so that can manifest in a few different ways. Some people like the long-winded story. Some people like the bullet points, that’s an example of kind of format. Another example is kind of the dimension of the point that I’m trying to get across that maybe I wanna emphasize. Some people are more analytical, kind of the classic personality trait breakdown, and they wanna see the numbers, they wanna understand the math, or they want to understand the logic of how you got to your conclusion.
Other people just want the conclusion. Other people may want to the outcome picture painted for them. So, I guess another element to that is, as I’m getting to know people, particularly people that I will be interacting with more frequently or will have more important interactions with, those are the type of types of things that I make an effort in many cases to try to suss out too.
Michael
The more it reflects into, how someone else works best, the more energy it takes us. The more we make them flex new how we work best, the more energy it takes them. How do you reason about where to put that balance along that spectrum in any particular point in time?
Jason
Well, that’s a great question. Again, if I think back to kind of a comment that I just made of, the assumption here is, the scenario is a relationship that I want to invest in.
Again, whether that’s personal, professional, or something in between. And I think most of the time you don’t invest financially in relationships. So I think kind of the point that you made is a great way to almost, kind of, mentally quantify your willingness to invest in that relationship.
People shouldn’t work hard or it shouldn’t be hard or feel like an effort to get to know me. And I think if I just look at things from that lens, that it’s kind of incumbent on me to be the one investing a little bit more, just because why not?
Michael
So you tend to flex into their space and bear the cost yourself?
Jason
Yeah, I think that’s fair to say. It should be easier to get to know me. It makes things less, less challenging for the other party.
Michael
So now that you’re expending all this energy flexing into the space of everyone else that you’re working with, how do you ensure that you have enough energy reserves ahead of time to sustain this? And how do you recharge throughout the day? So if you can’t bank up enough ahead of time.
Jason
That’s a great question.
Again, I think there’s, I would say there’s two elements of that. The first is, there is some thoughtfulness that I try to put into who and where I do invest my time. Obviously, as you said, I don’t have infinite energy stores, so I do have a sense of who and where I want to make those investments.
And the other thing is, I am a believer that the more I invest in others, the more they’ll invest in me, so to speak. The old, whatever, you put out into the universe, I think you’ll get it back if not immediately, eventually at some point.
And I’m kind of conscious of that. So, I guess the opposite sign of that same coin is if you put out negativity into the world, then I do believe you’ll just get the same thing back sooner or later.
Michael
So is it then that you’re beginning the day or period periodically throughout the day, looking at what your next meetings are, how far out of your preferences you need to flex to be within their preferences, and then taking steps there and then to ensure that you have enough energy ready to go?
Jason
Absolutely. And again, kind of the step even before that is being somewhat thoughtful in the meetings that I take to begin with. And there is a difference between a short email interaction and a full conversation, and how do I stack rank and filter out the more meaningful conversations I do want to spend the time to have.
Michael
Have you had times where you either have consciously decided not to flex in to the other people’s preferences, or after the fact, you’re reviewing how things went, you said, Oh, actually, if I’d made them work a little harder, if this might’ve had a better outcome?
Jason
I think so, and I think that’s more, rather, there’s no sort of particular examples that come to mind, but, professionally especially, I started my career in sales and I think in a professional context, that sort of philosophy that I’ve built, very much came from mistakes that I made in sales as a salesperson, and I think the classic trap that a lot of people, or the classic sort of misunderstanding of sales that people get to get caught up in, is your efficacy and your quality as a salesperson correlates with your ability to pitch i.e, your ability to just speak, and lecture, versus your ability to really listen and kind of, fine tune your responses that, that is definitely a professional lesson that I learned over time. It was one thing to be a good speaker. It was one thing to be really good at a presentation. But one of the things that you do learn in sales is, at least in my experience, that doesn’t actually correlate with your commission checks.
Your ability to listen is actually something that correlates more directly with your financial reward in sales. And that’s an explicit lesson that I learned that sort of helped to inform my approach to things moving forward.
Michael
How do you build cultures where people feel safe and empowered to bring their unique talents into everything that they do?
Jason
Also, a great question. So when it comes to team building and team culture, team philosophy, I guess jokingly, how I describe, how I like to operate, is my expectation is that I’m treated like an adult.
And my expectation for people that I work with is for me to treat them like an adult. There is a catch, though. And I bring my ‘dad’ approach to that catch, which is I have a teenager at home. I have two kids. One of them happens to be a teenager now, and he kind of has to earn the right to be treated like an adult.
And luckily, for him, and I’m very proud of the fact that he’s earned the right to have a fair bit of autonomy when it comes to the things that he does on the weekend and what he does with his money and so on and so forth. But, he had to earn that right.
Obviously, in a professional sense, I wouldn’t be giving an allowance per say, to my team members, but when it comes to their decision making, their autonomy, kind of the fidelity of information that I expect, or you frankly don’t expect them to provide for me, my expectation is, as kind of quickly and organically as possible, we get to a place where I’m able to treat them as an adult.
More practically, you know what that means I think for people that I work with and people that work for me is, providing that autonomy, and appropriate level of context and transparency with objectives in the business, priorities in the business, should allow them to feel agency and with that agency, in accordance and act without, back to the energy question you asked, without me, frankly, having to expend too much energy monitoring or overseeing what they do.
Michael
What tells you the amount of trust or agency that someone has earned?
Jason
Great question. So for me, I look for kind of soft, somewhat intangible. The first is pride in their work. When people have a certain degree of pride in their work and conviction in what they do, that tends to be a great sight.
And then what’s more important is, if they’re proud of their work and have a desire for agency, the things that they prioritize align with you, what the greater organization is trying to do. And I think if you can get to, if you can get those two things right, and I think it’s on my part it’s more incumbent on me to ensure that there’s the level of, kind of context or contextual understanding and transparency and the business and decision making implications, and side effects of things that they do, so that they don’t make the right decisions per say, but make decisions that align with kind of the guardrails.
Then, if I’m hiring the right people that have that sort of inherent pride in their work and inherent drive to do interesting things, then I think those are the sort of two responsibilities on either side: me providing the appropriate context and support, and then providing just the desire to do good work.
Michael
So you’re focusing somewhat on the outcomes and more on the approach they’re taking and the way they achieve those outcomes?
Jason
Correct. Yeah. Yeah. I would say the approach, to me, the approach is the important thing. The approach is the transferable skill, if you will. If you get to the right answer, but you do it, maybe you step on a few people along the way? I don’t think that’s generally speaking, I wouldn’t say that’s the best approach if you take the right approach and you don’t get to, if you don’t get to the outcome or the number, the answer that I’m expecting, but it’s within the context of, say the guardrails of prioritization and sort of general direction that we wanna go in, if nothing else, that’s actually quite exciting for me ’cause it’s probably something that I didn’t think of. And if I trust the approach that you’ve taken, then you’re probably right, ’cause I’m not always right. You’re almost certainly gonna, start a fairly interesting conversation at that point.
Michael
How did those conversations go when you’re consistently, the approach is right, everyone agrees we’re doing this in the right way, consistently, and the outcome that we’re heading for just isn’t being reached? How do you handle those situations?
Jason
So I think, there’s, I think there’s two elements of that.
The first is, if it’s happening repeatedly, then what is the teachable moment? Not just for that individual, but more so for me and the greater team. Is there something that within our approach, within our recipe, we’re consistently missing? That would be the first question.
The other question to ask, and the other sort of responsibility that I would give to myself is, presumably, the first time is a mistake or something that you overlook. The second time is maybe an unfortunate pattern. If it gets to the third time, then there’s something that I’m not doing correctly in terms of coaching and facilitating that retrospective investigation or facilitating whatever fine-tuning should or could happen in that next iteration.
Michael
So just because we all agree that the approach is right doesn’t mean that the approach is exactly.
Jason
Correct. And I don’t think anything’s ever exactly right. And I think that’s again, I guess, a leadership philosophy that I’ve adopted is, I don’t think I have a hundred percent success rate. I don’t think I’ll ever get to a point where I have a hundred percent success rate, but I’ve probably gotten to a point in my career when.
Yeah, where I can hit a good 70-80% and if folks on my team, at an earlier stage in their career, they’re giving answers or they’re suggesting things that are 60% accurate, just to use our arbitrary numbers, my job is not to pivot over to my 75% answer. My job is to figure out what they can do to get to even 68% because those are just arbitrary numbers, and that’s probably close enough to get within striking distance of where we wanna go. The bigger challenge is if neither one of us is getting to those majority-level numbers. And having the wherewithal, the sort of pause and do some investigation rather than forcing your way through again.
Michael
So you’re always then focused way more on refining the process and trusting that to take you to the outcomes. The desire versus aligning to outcomes and adjusting or even forcing that process to hit those.
Jason
Correct. And again, to reflect back on kind of the earlier part of our conversation, perhaps a fun factor trivia about me is, I actually graduated from engineering school into the original or the tail end of the original dot com burst in the early two thousands.
So I had a hard time getting a job or getting a real job, quote unquote. So I actually went back to school, but I went to cooking school. And one of the things that I learned in cooking school was, I spent a semester in cooking school. And what I learned was how to chop really well, and I learned how to make master sauces.
Those were like the two things that I take with me. So I learned how to make a bechamel and a beurre blanc, and a Velouté, and so on and so forth. And what I learned about cooking is that those are baseline recipes. So those are baseline skills, and you don’t make dinner with bechamel, but you can make a million things with bechamel, and that’s a foundational skill that you can then layer on, the specifics of what the dish is or the meal’s going to be.
But if you get that right, you get pretty far along. And that’s kind of how I approach my approach to business, and my professional sort of pattern matching is in a professional context when it comes to the approach to solving certain types of problems. A, there’s only a finite amount of categories of problems. And then B, can I develop the four master sauces in my own repertoire for myself and to teach to others to get that baseline, idea of a solution, if you will. So then you can just focus on the fine-tuning part, which is kind of, I guess, the secret to success.
Michael
I like that analogy a lot. When you’re making a meal, there’s an infinite number of meals you could make. There’s a much smaller amount of those for you, and whoever else is joining you for that meal is likely to enjoy. Within that search set, there are many different options for how do you achieve that outcome of certain dinner with certain dishes and flavors and such, and how you get there is really the most important thing because if you are exploring and playing as you go, then the end result is always gonna be delicious, even if it turns out to be differently than what you started out.
Jason
Yeah, absolutely. Yeah, that’s exactly it. It’s how you get there is the fun part.
It’s very cliche, but it’s true. The only sort of caveat is there are a few things that you learn along the way to get there a little bit faster, so that you can have a few more bats, so to speak.
Michael
Right. Most people aren’t gonna enjoy mayonnaise and grape jellies.
Jason
That’s right. I would hope so. I would hope not, anyway.
Michael
How do you talk to the business leaders about the business value of approaching work this way, where the outcomes are almost mere side effects of the way that the work is done?
Jason
I think, actually, you put it well. I think that is the lesson. Sometimes it’s a hard conversation to have, sometimes it’s an easy conversation to have. The outcomes really are a side effect to how you work. It’s just like that, master sauce, how you cook, and now you put together a dinner analogy. Especially in the world of startup, I think people often get caught up in that outcome.
I want to get to an exit. I want x number of valuation. And, those are very much just an outcome of how well and how well you can execute against solving problems. The more meaningful the problem is, you’re positioning yourself better for that positive outcome, but just as important, if not more important.
Based on my own experiences, how you can execute against solving that problem will impact your likelihood of success and getting to that outcome. And, solving that problem means how you operate some of the team dynamics, the culture building that you and I have talked about, through to just understanding the different departmental operations and capabilities that you’ll need, it’s all a puzzle.
And the outcome of the puzzle is you get a beautiful picture, but if you don’t get the right pieces, then it’ll just be, I guess, not a puzzle. It’ll just be a big mess on the table.
Michael
Yes. For people who this approach first approach is foreign, something they haven’t experienced, and is maybe even opposite of everything that they’ve learned and perhaps their experience has been, how do you help them open up to experimenting with this different philosophy?
Jason
That’s a great question. I think generally speaking, having more of a process-driven focus on, approach to professional challenges, specifically, it inherently allows you to have a little bit more comfort with ambiguity. If I completely pivot the metaphor that I use, my experience is that building a business, of building a tech business in particular, where, a lot of the things that you’re trying to do are novel. It’s like sculpting.
You start with a block of clay, and you have to chip away until eventually you get the sculpture that you wanna work on. And when you’re sculpting, you probably have a nominal idea of what you want to build. You wanna build an animal, or you wanna sculpt an animal, you wanna sculpt a person, you wanna sculpt a bridge.
And then, as you’re sculpting and as you’re carving with that clay, then the fidelity of that object, sort of, manifests. But there’s some built-in ambiguity, both in terms of, as you go, maybe the dynamics of the nature of the clay and so on and so forth.
Inspiration may strike you halfway through and force you to pivot. That’s very different than a linear paint-by-numbers expectation of creating art. And I think, especially, in my experience in larger organizations and more established cultures like that, I think people are almost lulled into the expectation of a linear approach to whether it’s their career or their approach to tackling a business problem.
And that’s fine if you have that kind of rigor and support around you that, perhaps, a large organization provides. But in the world that I find more fun, that doesn’t exist. So you do need to have a fair bit of comfort. So when it comes to people and getting them to understand that and build that comfort and build that muscle of comfort with ambiguity, I start to just talk through scenarios like this, and if you don’t have that comfort or it doesn’t appeal to you, that’s okay too. Back to who I invest my time in, when it comes to team building, those people that I invest in, I do recognize that not everybody would think this way, or not everybody has comfort or has desire to think in this way, or operate this way, or approach challenges that are fraught with ambiguity. So it is incumbent on me as a leader to find those people. And if people don’t feel excitement in that kind of environment, that’s okay. And, partly it’s incumbent on me to identify that and maybe help them find something more exciting for them.
Michael
And for people for whom change is a challenge, this sounds like it’s just full of constant change, if we’re always refining the process and we never know exactly where we’re headed.
It’s not really that it’s constant change, it’s that we’re heading towards a more refined process, and maybe that comes in iterations for periodically locked down, okay, this is our process now, and we continue refining from here. And then that gives people who don’t enjoy the constant change as set points where they can settle in and say, Okay, I understand this process now. I see how it’s better than what we had last month, or last quarter, or last year.
And I know that there’s gonna be more refines here. I’m not so comfortable with that. And this process here, this feels good. I can settle on here and use this as a foundation from which to explore into this other change that’s coming, perhaps a little more securely.
Jason
Yeah, correct. What I’m proposing is not a completely ambiguous, chaotic approach to things.
Really, it’s more about if we can get most of it structured, then I want you to have the agency to refine the rest of it or layer in your opinions and your thoughts, to get us to the next milestone as you described for the next horizon of what we’re trying to do.
And again, I find that, that stage of organization, if you will, or that size of organization, frankly, it’ll be a little bit more fun because it gives you the opportunity to put your fingerprints on the work that you do in a more meaningful way, and it also gives you there’s the unsaid opportunity of making mistakes.
And I’m gonna give you a bunch of erasers, but you try not to run out of these erasers too quickly.
Michael
Yes, that’s a good point that the time scale at which we’re doing this work doesn’t have to be seconds or minutes or even days. It can be, this is the process for the sprint, or this quarter, or this year.
At the end of that sprint quarter/ year, we will do a retrospective on how this is working, and we’ll make some changes, or we’ll make one change even. The refinement doesn’t have to be everything everywhere, all at once. It can be stretched across longer timescales and done in smaller increments or batches.
Jason
Absolutely. And that’s, tactically, that’s a great way to make this whole kind of thing a lot less overwhelming because they’re baby steps, if you will, or small steps. And baby steps are small changes. And ideally, we get to the point where, you know, next quarter nothing’s changing just because we have maybe become close to perfection in what we’re trying to do for a period of time anyway.
Michael
How do you know when you’ve gotten things to that close enough to perfection for now?
Jason
I would say explicitly, part of planning, even in a more casual way, is to have some upfront understanding and alignment on expected outcomes and markers of success.
In my ideal world, we’re getting pretty close to those. But even with pretty close, there’s probably room for improvement, but in some cases, you do actually exceed some of those success metrics or success expectations. And at that point, I guess, that’s the point when I ask for more investor money because that’s when you know you’re really onto something.
Michael
How much do you notice, and have you maybe set out the success metrics ahead of time, and how much are you discovering them along the way?
Jason
I think back to generalized patterns. At least in my domain when it comes to specifically product and more specifically kind of enterprise software and applications, I think there are high level, broad, call it user engagement and also business metrics obviously that you can start with as kind of fairly universal, both North stars, or at least if not North Stars, sort of a spot in the sky.
And I think as you’re iterating and executing and kinda learning as you go, the challenge is to get at greater levels of fidelity. So, perhaps there are general stickiness, user engagement metrics that I’ll start off with as that kind of area in the sky that I’ll want. The ratio of daily active users to monthly active users is some permutation in the ad for frequency of not just usage, but return usage.
And then, depending on the application, the user, the organization that I’m working on, so on and so forth, there will be nuance that I try to uncover with regard to fidelity and specifics of how I would look at measure and even benchmark those types of metrics. So from a measurement standpoint, that’s kind of the approach that I take.
So, V1, like anything, like software, V1 of the plan is, directionally should be, sound. And then as you get to the further and further iterations, A, you’ll determine how close you are. And then B, more importantly, you’ll be able to get to a little bit more, higher fidelity versions of those same measures and tactics frankly to, kind of get to the next step.
Generally that would be my approach to things.
Michael
How do you help people find their way through all the change, uncertainty, and overwhelm? It seems to feel light these days.
Jason
I think, kind of reflecting back on just other parts of our conversation, I think everything in life especially, will feel really overwhelming if it feels really big. So, you know how you’re able to, or if you are able to, break those big things, scenarios, situations, challenges, problems, down into more digestible pieces, I think naturally they become less overwhelming, and they become easier to understand and more accurate, if you will. If I take a very clinical example is, again, in a professional sense, I’m a product professional. A widget is designed to solve a job for a user at the end of the day.
But, most of the time, the vast majority of the time, those jobs that people are trying to do in business in particular can be broken down into sort of very small slices, kinda links in a chain. So, as a product person, it’s important to understand all the links in the chain.
And then when it comes to executing against the strategy, breaking down the priority links in the chain so you’re able to take a big thing and try to chew away at it, bit by bit. In a personal context, whether that’s a financial challenge you may be hitting or a relationship challenge that you may have.
I think you can probably take a fairly similar approach of, yes, it is a big problem. I won’t belittle you, quote unquote, in trying to convince you that it’s not a big problem, but every big problem could be broken down into a series of smaller problems, and once you do that, then you know, it doesn’t change the scope of the macro issue you’re dealing with, but it can change, kind of your mental approach to how you wanna solve it and hopefully make it a little bit less daunting.
Michael
I agree. There’s always a smaller step. There’s just as in the metric system, there’s always a smaller measure, there’s always a smaller step that we can take. If a meter’s too big, we can take centimeter steps. If those are too big, we can go down a millimeters and eventually, if we’re down to, I don’t know, something, there’s probably a Google Plex meter or something down at the super, super itty bitty scale, there’s always a way to make it smaller.
Jason
Absolutely, and the extension of that is it doesn’t matter how small it is. If you’re solving for a small part, you’re making positive progress. You’re making forward progress. And eventually enough of those small parts will become a centimeter, will become a decimeter, or whatever the incremental measure is.
And even beyond that, eventually you’ll get, kind of, the inertia or momentum on your side to then hopefully solve more and more, faster, or sooner than you thought.
Michael
Absolutely. What is the best way for people to connect with you, Jason, if they’d like to learn more about building their approach as they go and letting go of the outcomes?
Jason
You know what, the best way to get a hold of me or to connect with me would probably be through LinkedIn. Probably the easiest. I have a fairly unique name, so I’m a fairly simple query away. I don’t know how many Michael Hunters there are, but I imagine there’s more Michael Hunters than Jason Deas, so I could be wrong.
Michael
There are a huge number of Michael Hunters, so it’s one reason that my LinkedIn is not Michael Hunter. It’s something more unique.
Jason
Oh, there you go.
Michael
I’ll have those links in the show notes. And for people listening who don’t want to look at the show notes, Jason’s last name, Dea, is DEA.
What would you like to leave our audience with today, Jason?
Jason
You know what, I’d leave the audience with, hopefully they picked something up, is, I very much enjoyed our conversation, and I do believe that, I guess a totally, maybe unrelated, but I have another underlying philosophy that I take with me is one of the things that I’ve learned in life and professionally, especially, is extraordinary things are just accomplished by ordinary people. And I think that’s a misconception that many people have, is extraordinary things can only be achieved by extraordinary people, but extraordinary people are just ordinary people that have done extraordinary things. And maybe part of it is just breaking down a big problem into smaller chunks.
Or maybe part of it is just supporting or surrounding yourself with people that believe that you have the ability to do that.
Michael
I agree. Every extraordinary person, extraordinary result that I’ve experienced or met or seen has always been made up of a bunch of tiny steps. It has never been, I step out of my house today, and suddenly I’ve built a rocket and I’m at the moon. It’s been a whole bunch of little steps to get myself to the moon.
Jason
Yeah, absolutely.
Michael
Thank you for your time today, Jason.
Jason
Yeah, thank you for inviting me. It was great.
Michael
This has been great, and thank you, audience, for joining us today as well. Jason and I would love to know how are you shifting your approach today? Thanks, and have a great day.