What Clarity Coaching Can Do For You




Transcript below, for those of you who prefer reading over listening!

Welcome, everybody. It’s my great pleasure to be here today speaking with Joshua Walsky. Joshua is Co-founder and Chief Technology Officer of Broadway Technology. We got to know each other when a mutual friend introduced us, and said, Hey, maybe Broadway and Joshua could use some coaching. And that was the start of a great working relationship and friendship. And Joshua has been somebody who has been wonderful and astounding to work with over all those years. He just let me know that he’s now onto the next stage of his career, but I thought we’d start at the beginning.

Joshua, thank you so much for joining today. Tell us a little bit about Broadway. Why did you and Tyler start the company?

Well first, thanks for having me. I’m looking forward to having this conversation. Broadway was founded in 2003. Tyler, Co-founder and CEO of Broadway, and I had known each other for about five years at that point. We’d worked together at a prior job, and as Tyler got involved with an automated trading group, he called me up to implement some software. In 2003, we had an opportunity to take that software, commercialize it, and build a company. 

Tyler and I both had always been engineers, entrepreneurs, and wanted to start a company– and this was an opportunity to do it. We had a chance to take some software we were proud of, turn it into a commercial product, and then build a company around it. At the time, we had no idea what we were about to get into. We knew we had software, we knew we wanted to start a company, and we had a potential customer. I remember sitting around in the hallway, and the decision came down to, Did we think we could get one more customer? Because if we thought we could get one more customer, then we should go for it. Otherwise, we should kind of stick to our day jobs and continue with the original sermon. 

So we looked at each other and said, Yes, we think we can get one more customer, let’s go for it. That was the impetus and the origination of the company. We had always thought about building software in a better way and building a company in a better way. We had a very idealistic start, and wanted to try and do things differently, to take some of the learnings that we had in our first employment experience and apply them in a better way to build an organization. So that’s what we set out to do.

I can just see you and Tyler sitting in that hall making that bet. That’s such a great founder origin story. At the point that you and I meet, you’ve been working on that for 15 years or so, and someone says, Hey, you should think about a coach. Had you had a coach before?

None of that. And this is a confession that, Jeff, I don’t think I ever told you: when Tyler mentioned the idea, the first thought that went through my head was, How expensive is it? We don’t need this. I don’t need any of this. We don’t need any of this. We’ve gotten this far. As you said, it’d been 15 years, we’d grown to upwards of 200 people, we have major banks as customers, we were running large deployments… I had no experience with coaching, so I had a number of preconceptions. And one of those preconceptions was, I don’t know why we should spend money on this. I don’t know how this is going to help. Yes, we have our struggles, but how does this fit in? 

And obviously, looking back, I was very much on the wrong side of that. I’ve turned 180 degrees and I see so many things that I was completely unaware of.

So you get over that hesitancy, or Tyler talks you into it, or whatever happens and we end up talking to each other. What did you expect from coaching?

I did not expect a coach to give me concrete steps, and things to think of, and show me areas that I was not succeeding in but thought I was. I expected a coach to be someone who was just reaffirming what I already believed. One of the things that ended up being very impactful was being approached with new perspectives, and ideas that you as the executive shouldn’t be doing everything: you’re doing a lot of things you’re not very good at, and you don’t like them, but you’re doing them anyway. Why are you doing that? It doesn’t have to be that way. Here are tools to both figure out how things should be, and then how to actually make it happen.

Awesome. You are a person who is very smart and has very strong opinions, and I was surprised at how flexible you were on those opinions once we had a grounded logical conversation. And one of those topics was how much you were managing at a tactical level, even though your organization had grown so large, and you had put yourself as a critical path on a lot of different processes.

Remember that experiment we like to run with clients, which we ran, and we talked about: what happens if you don’t show up tomorrow? What gets worse? What stays the same? And what gets better? As we went through that, I think you were surprised by the number of things where you discovered, this may actually get better if I didn’t show up tomorrow. 

Do you recall anything that was an a-ha for you, during coaching, where you think, yeah, I have to design this thing differently. 

Yes, I had multiple a-ha moments. That line of thinking was exactly what brought me to some of those moments, you know – what would get better, what would get worse, as well as understanding that there are certain things where I’m going to excel, and I’m going to be a differentiating factor.

One of the interesting things about founding a company and being an executive is that the people who get themselves in those positions have tremendous self confidence. Some might call it overconfidence. But you have to have self confidence and believe that you can achieve the impossible. As the company grows, and you start picking up new responsibilities, you approach them with that same overconfidence. Until someone forces you to actually think and say, Well, wait a second, you’re doing all of these things. What would get better? What would get worse? Are you providing differential talent capability insight to that thing? Or are you just doing it to the best of your ability, which may be good, but not great? Why don’t you think about getting great there? That perspective was insightful and enlightening and freeing in a lot of ways. 

Scaling an organization required building consistent, repeatable processes. But if you remember, one of our founding tenets was, we believe there’s always a better way. Well, the thing about someone who is constantly looking for a better way is that they really don’t like repeatable processes. They’re making version 1.1, and 1.2, and 1.3, because they’re constantly tweaking. That’s how I would approach problems as an individual. But when you’re trying to scale a client services organization where you have a lot of personnel who need to follow repeatable processes, you can’t change the process every six months with a new iteration. Looking at areas like that one, I said, Well, while this works in software architecture, it’s not working in this domain, so how do I get myself out of this domain and actually find someone who’s better at that than I am.

You taught me that managers succeed through the work of others. And in order to succeed through the work of others, you need to stop jumping in and doing things, and you also need to feel good about that, and feel fulfilled through that. And that was not an area that was well-aligned with where I got the greatest fulfillment from work and had the greatest impact. So finding ways where I could get myself out of that responsibility, so that I could focus my time and effort to where I was making a differential impact… that covers a couple of a-ha moments. 

Ultimately, the big a-ha was, stop trying to do everything, and figure out how to find areas for other people. Building a company and achieving successes by taking on more and more responsibility is like its own dopamine-driven feedback cycle: you take on more, it succeeds; you try and do more, it succeeds; you try and do more until a point at which you pass the point it’s breaking – you just don’t realize it because you’re now addicted.

I love that analogy. You’re a great coachee because you have three attributes that are crucial to being coachable. 

One is you really care about excellence. We talked about that a lot. You cared more about the standard of excellence than you being the person who achieved it, which is a really critical distinction. Achieving that pinnacle is way more important than I’m the guy who achieves that pinnacle.

Two is you really were hungry to learn. I saw you continually go through these processes. You’re a software engineer, so you’re a hyper-rational, hyper-logical person, and we would go through these bad outcomes, and you would say, Yeah, okay, got it, I can see how I am in the middle of that bad outcome. And I can see, it’s because I’ve been thinking about things this way. And the way I’ve been thinking about things is preventing me from getting to excellence, the path to excellence really is me getting out of some of these things, as opposed to me driving harder, working harder, trying to change who I am. 

Third is you are very goal oriented. We could use specific goals or specific events to actually anchor against, and learn against, as opposed to just a random series of events that we’re hoping come together in a pattern of learning.

You were excellent at all three of those things, and you progressed very fast as a result, while Broadway was growing a lot, and going through a sale and a lot of change. And it was really great to work with you. 

Now let’s take it to the next step. Broadway was a successful M&A transaction and, and you’ve gone on to greener pastures, and I reached out to you a while ago and said, Joshua, I think you would be an amazing clarity coach, would you be interested? And you said yes, and are now in our coaching training. 

Tell me a little bit about why. Tell me what led you to say, Yeah, I think I’d like to try this coaching thing now that I went from the “we don’t have money, and we don’t have time for this, we’ve got it” to “it’s different than I thought it actually has been very helpful” to “now I may be good at this and help others.”

Thank you for that. I care about being open-minded and thinking scientifically and trying to get out of myself. 

Why am I interested in coaching? Some part of it was because I was so wrong at the beginning, which led me to realize there is a world out there that actually is very valuable and can help a lot of people, including myself. Coaching had a very big impact on how I approach things. It made me better. If you go back to that tenet of finding a better way, coaching definitely made me better. So the idea that there’s this thing out there that I could possibly learn how to do, or help others achieve… I’ve been reflecting on that question a little bit, too. I almost feel like it’s a trait of humanity. Or maybe it’s a trait that I particularly closely identify with, which is, if something beneficial happens to me, I want to figure out how to pass it on. I get joy out of that.

Coaching provided a new perspective, a new way to think about me as an actor in a world, not just doing the actions, because that’s kind of your day-to-day, but stepping back a level, and thinking about me as the actor, and how I could potentially change that and do it better. So that I could get greater fulfillment, happiness, and have a bigger impact on what I cared about. That perspective, and being able to then teach that perspective to people, became an area of interest. We’re all operators in large systems, be it the company that we’re in or the society we’re in. And sometimes you feel like the system we’re in dictates all of our actions and our behaviors. Coaching is a way where you kind of learn how to realize that situation, and then actually make changes both to your own position, the way you approach things and what you do as well as the system around you.  

That ties back to systems thinking and system interaction, which is part of what got me into computer science to begin with. So it’s an area of interest to me. I see coaching as an opportunity to learn how to apply that in a human domain instead of a silicon and wires domain.

I hadn’t thought of it that way. That is amazingly cool. One of the things about clarity coaching is that we’re trying to design and deploy a system that maximizes the probability that we’re going to find and unleash human potential. We’re very oriented towards that system. And one of the key elements of that system – and I never connected these dots before – is very similar to how you think about architecture. Because in addition to being a Founder and Chief Technology Officer, you actually were a systems architect. You thought at the global level about all the different complex transactions that were going to flow through the Broadway systems, and what were the optimal ways to make that happen. And really, to take that talent of yours for systems design and the systems sort of orientation, and apply it to human beings through the lens of coaching is a completely natural and understandable extension of what we do and why we’re trying to do it, including the pay it forward aspect. 

If you have the gift of being able to work at systems level, see design as an element of system, architect designs in order to influence people’s beliefs about themselves, show them their blind spots, their strengths, and help them create something that will take them to greater heights. It’s so cool to be able to pattern match that off your bits and bytes background, your silicon background into the human realm. And I’ve just never seen that before. So thank you for sharing that, because that is very, very cool.

And that’s exactly how I see it. Company building is similar to programming in so many ways. Tyler used to say, you can’t think about people that way – but it’s just systems, people are incredibly complex systems. And getting the parts designed to interact together and efficiently… It’s a systems problem. So that was definitely something that attracted me to coaching: One is the kind of basic computer systems building, two is the company building, and then three is coaching and how individuals interact in those systems.

The reason I’m so inspired by what you’re saying is, I was talking to a CEO earlier today and we are having the sort of the classic –  this a new relationship – conversation between hard skills and soft skills. And he is coming from a point of view of, Listen, I want to have a coach, coaching will be great, whatever, but let’s be clear, the hard thing about business is the hard skills stuff, you got to have the right strategy, you got to have the right amount of capital, you got to have the right go to market, and all that stuff. 

And I say, I’m pretty sure if we have this relationship and it goes well, you’re going to understand all of those things are difficult because people are difficult. All of those things are not difficult in and of themselves, they are difficult because you have to predict what people will do in a complex, highly variable, unpredictable system. And how people are going to respond to different incentives when it’s not a rational thing. It’s not a clear input output. 

And so, in some ways, what you’re talking about is taking your systems talent to a higher level of abstraction. Because it’s a more complex thing than even a computer system, which is extremely complex. Because at least at a binary level, you can structure things to see a system in a certain way. But in an analog slash quantum level – which is where humans play – it’s incredibly difficult to see the complexity of the thing of why human beings are doing what they’re doing, why do smart people do dumb things, as an example. It’s very tough, and so you’re taking that talent of yours to a next level of difficulty, which to me is so cool and inspiring.

That story reminds me, one of my preconceptions prior to actually getting into coaching and meeting you, was that it was going to be all soft skills, and really just teaching me how to be nicer, because I had been criticized for being a little too harsh. So I was like, I don’t need to be nicer. That was my preconception.

Through the coaching evolution and growth, one of the things I realized is that it’s not about being nicer, it’s about understanding the systems and the humans working in it as a big picture. And that’s one of the insights that I got – which you gave me from coaching – that ‘soft skills’ or ‘being nicer’ is really about understanding that you want to be able to create something that actually works well with the players that are involved. And in order to do that, you need to understand how they all fit together. 

Well, this has been fantastic. Thank you so much for your time, Joshua. It’s always great to speak with somebody who I admire, but also just to learn something in the moment. So thank you so much for sharing, and for your time.

Always great to talk with you, Jeff. I had great fun.

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