Episode: 389 |
Braden Weinstock:
The Human Operating System:


Braden Weinstock

The Human Operating System

Show Notes


Braden is a startup entrepreneur, an action-oriented and strategic operator, and consultant with operational expertise in a broad range of experiences across crypto, hedge funds, software technology (SaaS), commercial real estate, management consulting, luxury retail, and more. In this episode, he discusses his purpose, working with Bridgewater and Knotel, and time management. 

Key points include:

  • 03:06: Braden’s operating value
  • 08:29: The list of operating practices
  • 10:18: Installing and eliminating habits
  • 18:57: Time blocking and deep work
  • 27:47: Texting vs. talking
  • 29:54: Bridgewater and Knotel

Braden can be reached through his website, www.bradenww.com, or through LinkedIn


One weekly email with bonus materials and summaries of each new episode:

Will Bachman 00:01
Hello, and welcome to Unleashed the show that explores how to thrive as an independent professional. I’m your host Will Bachman and I’m excited to be here today with Braden Weinstock. Braden, welcome to the show.

Braden Weinstock 00:14
Thanks. Well, appreciate you having me.

Will Bachman 00:16
So Braden, I’d like to talk about your human operating system Manifesto, which I find on your website. And I think it’s a bit distinctive. I don’t know, other people who have written an operating system, you’ve got your Manifesto, operating values and operating practices. And we’ll talk through this. Tell me a little bit about kind of overall, what gave you the idea for this? And how did this come about?

Braden Weinstock 00:43
Yeah, well, thanks so much for pointing this out. This is something that I’ve put a lot of work into over the years. And it really came about, because over time, I noticed when I started my career as a consultant, but also, the last couple years was working on building a fast growing startup that turned into a unicorn. And what I noticed is, we didn’t really always have a way to figure out how to work together, you know, we would meet people to jump onto a project, or we were onboarding people very quickly. And I started to think about what’s important to me what’s important to who I am as a person, and how I operate. And so started writing things down that were important to me, and trying to describe them and share them with people who are either working with or for me, and you might have heard of the user manual, that started to be a popular version of it. But I didn’t think it fully captured the depth of importance that I was trying to get at, which is like, what’s behind my decision-making? And how, from a tactical perspective do I operate. And so after putting this together and working on it, and people telling me, Hey, this is actually really helpful for getting to know you, and being able to develop a working relationship as a manager, or as a colleague, as an executive. When I started building out my website, I thought, well, if I really want to live my values, I should own my values. And so I own my values, let me be transparent with them and put them out there. And at the least, they’ll attract people who find them interesting and align with them, though, obviously, maybe repel some people who don’t align with them. And that’s okay. And ultimately, I can live, higher integrity and better alignment with who I am. And the people I work with.

Will Bachman 02:33
Let’s talk through your operating value. So I’ll just read off this list. That’s okay. So there’s compassion and thoughtfulness. And then there’s a plus button to expand on that. There’s curiosity and humility, grit and discipline, logic and reflection, integrity and transparency, and then responsibility and accountability. How did you what was the process that you came that you went through to come down to this set of 1212? values?

Braden Weinstock 03:06
Yeah, it’s a, it’s definitely a process of constant iteration over the years. You know, it started as like a long list, I did this values exercise, where I started writing down, what are a bunch of values, and then I started ranking them. I had to do definitions, and then I would, over time, find research, or psychology articles, management articles, etc., on these topics and see how they fit together in something that kind of in the middle of my career I was struggling with was, you know, nothing was black and white. Everything in life had some kind of yin and yang balance where things were in relationship to each other. And one day, I had a, I had a manager, a very senior executive, say to me, he’s like, both can be true. And at that point, it just kind of clicked on like, for my operating values to work, it’s about combining the components. And so I started to pair the 12 into these six groupings, and ultimately use those to guide how I think and operate. So if you think about, for example, grit and discipline, you know, we hear about grit and people say, Go have grit in in stuff, but to have grit, you need to live with discipline, Jocko willing says, you know, discipline sets you free. But the grit is the value part of what I’m trying to live. And discipline is putting it into practice. And so I was really looking for pairings of how I could live my values in whole. And this is how the list came about.

Will Bachman 04:54
I’m curious about what values because all these things sound great, right? I mean, all these things sound perfectly. You know, reasonable? What are the values that did not make the cut that you had to say? Well, I have to exclude some are deprioritize. And I’m they’re all important. You know, there’s other values I have, but these are the top 12 are sort of top six pairs, what are some ones that were kind of on the borderline? And didn’t make the final? The final 12?

Braden Weinstock 05:20
Hmm. Great question. I think at the beginning, to be honest, I, I struggled with what, what our values, you know, a lot of times my list didn’t include values, they included tactics. And so there were a lot of pieces that I didn’t include. So you’ll notice, for example, empathy is not on here. Which is kind of a strange thing, because compassion is and so, for example, empathy was like, really difficult for me wrestling with and I heard Jeff Weiner talk about the difference between empathy and compassion. And I really came to understand, oh, compassion is what I’m after. Compassion is really about being able to care about what’s happening to somebody else, and be willing to put my time and effort forward, to help them help themselves be better or provide support in some way. Whereas empathy is just that feeling of it. So for example, I took empathy off my list. A lot of times people talk about truth, you know, I just want you to just give me the data, right? Two different things, but I’ll use both. Well, for me truth, who really evolved into integrity, so scrapped truth, integrity was about what I say is what I do is what I mean, and that alignment, about who I am and how I’ve lived, my life is consistent. And you know, anybody who’s taken like the authentic leadership courses will hear about that. But knowing how to live that value, means I’ll deploy truth. And I’ll be truthful. A lot of people talked about, you know, I want to be data driven, I would see that well being data driven is is good. And I agree. And I’m a pretty data driven person, myself, but I had to scrap that. And I got into logic, which was, really what I’m looking for, is sound logic and common sense in decision making processes. Data is an element of that. And so I ended up evolving data driven into logic. And furthermore, when I started to think about it that way, I saw that the behavior practice I needed was to be open minded and have debate and being able to be willing to shed ideas that are wrong, in order for me to learn and grow. And so the focus wasn’t just in the data, it was on good logic.

Will Bachman 07:58
Let’s talk about some of the operating practices of this, read all seven, and then we can kind of go back and go through some of them. So habits and routines. Number two is prioritization. Number three is time blocking, and deep work. Number four is email processing. Number five is don’t reinvent the wheel. Number six, get leverage and number six, texting versus talking. Talk to me about how you came up with this list.

Braden Weinstock 08:29
So, for me, it’s interesting, these are things that I would say, over time in my career, I had to learn how to do. I don’t know if you remember kind of joining as a BA, but early days of being a junior consultant, I felt very overwhelmed. And I needed to learn to adapt how I worked from school into a new way of working. as a consultant, it was faster, obviously more stressful, and I needed to be more productive. And so over, you know, the next 10 or 15 years, I started researching and practicing how to be a more productive person. And so a lot of these came from that. So for example, the very first and most important thing that I ended up learning is habits and routines. Like, I remember thinking to myself, I’m not the same person I was a year ago. And so if that means I can change as a person, can I take active participation in planning that change? And that’s where I started to think about habit formation. And if I can actually strengthen my habit formation muscle by building little routines, so that my behaviors change, and I can become a better, you know, prioritize, or I can get things done faster, I can be happier. Let me strengthen and develop that and so that became is a really important foundation to being able to get stuff done.

Will Bachman 10:04
So let’s talk about that. So what are some habits that you’ve intentionally worked on developing recently, either installing new habits or limiting eliminating bad habits? Talk to me about some of those?

Braden Weinstock 10:18
Sure. So I’ll go back about five years. And I’ll tell you like I had, I hated journaling. I had no morning routine. I was inconsistent at the gym. And I didn’t meditate. But I was super stressed out. So I sat down, and I literally started drawing up micro habits. And I said, Okay, if I write down these micro habits, how can I start to take little actions to develop the capability of just doing something every day, and I got an app where I could actually track my habits, I put them in a list. And every single day, I just tracked it, I do it. So the very first one I ever did was brush my teeth every day. And the idea was, can I prove to myself how to build a habit and strengthen my habit muscle. And the first thing I noticed was, guess what, I don’t brush my teeth. 100% of the time, I was pretty ashamed to tell my wife that. And so I made improvements to that. The next thing was I started doing meditation every day, got headspace. And just every day, five minutes, make sure I do it. And this list of habits started to grow in the difficulty that it required for the discipline of building them. But it became easier to do. So I started doing a morning routine. And I read blog, my morning routine, I would pull people’s like activities in the morning and I put something together for myself. And I can tell you today like I have meditated for a few 100 days in a row right now. I have a morning routine, scripted step by step, I wake up, I do 10 pushups. Then I sit down and I do my meditation in my headspace app. Then I sit down, I read the daily stoic. Then I open up my morning journal, and I go through a series of activities, I write down three things that I’m grateful for three things I’m excited about, I have a daily affirmation that pops up on my phone, I use it, I ponder it for a second, I list out my top five priorities. And then I literally visualize out the boxes, how I spend each hour of my day. And then at the end of the day, I know this this year, a new practice I’m doing is I now do shutdown routine. So Cal Newport, big on deep work and productivity talks about having a shutdown routine. And I’ll actually go back to my journal, I take a red pen. I redraw how I spent my time based off of how I visualized, I do like some big win, and big improvement that I need to make for the next day, I check off what things I got done. And then I write the time just in the corner like this is the time I wrapped up, and I closed my laptop. I added that last routine, just in 2021, because I noticed working from home, I was like spilling over until my wife would come to me and be like it’s time for dinner, close your laptop. And so I needed to develop a new habit or routine to improve my ability to control how I was spending my time and not being overwhelmed and make sure I was spending time with my wife when I’m working from home during COVID. But I wouldn’t have been able to do such a routine if I hadn’t started with very small things. And I still track them in a habit app. And I ended up developing the muscle of building a habit.

Will Bachman 13:39
That sounds like a like sort of a textbook morning routine that you’ve got there. That is incredible. Keeping that up. And you mentioned some other stuff like what about you mentioned the pushups in the morning? Do you also have a kind of a workout routine? And he kind of diet routines? Any other habits? I’d be curious to hear that you’ve developed?

Braden Weinstock 14:00
Yeah, absolutely. And just to think the two concepts My belief is, if we can change who we are, we should create a vision for who we want to be. And then go back and think about what habits and routines we can build. In order to be able to put some of these behavioral change improvements on autopilot to get to who we want to be. That’s the ultimate goal. And because i’ve you know, studied psychology a little bit, I realized you can’t just always will it. So you’ve got to build big these things into habits. The gym is a big one. So what I ended up doing is I ended up blocking off a period of time right in the morning 8am to nine that I do my routine, and then nine to 10 I go straight to the gym. And for me, I used to be rock climbing, I would rock climb four days a week I had a very specific time I’d show up at the gym right in the morning, get everything done, and then go to get to work in COVID times. I’ve been able to to just do a walk in the park or go for a run, and recently the gyms opening up, I’ve changed my routine. And I go directly to the gym three days a week, and I do rowing. And I have 30 minutes, I have one hour in the gym, that’s it, I get in, I immediately do my stretches, I do 30 minutes of rowing, I want to hit a certain number of meters, and then immediately go do crunches. And I’m out and I actually tie myself to make sure I’m in and out of the gym in an hour. And I have those very specific markers of what I’m doing in the activities. In order to make sure I do it by making it a habit, it becomes a lot easier when I’m rowing. Because sometimes it gets very rote. I started doing audiobooks. And so like, it’s my way of engaging in getting an activity and getting to read a book. So like right now I’m listening to Bill Gates his book on on how to solve climate change. And it acts as an incentive for me to get to the gym every day. And that’s been really, really helpful. As far as routines to break, I would say, one of the most important things that I’ve had to work on is changing my eating habits. My wife jokes with me about how like when she met me, my idea of a healthy dinner was a steak that was half of the size of the plate, mashed potatoes and corn on the cob was my veggies, which is a starch. So a couple of years ago, I met a guy who said he did intermittent fasting, and I was like, That’s nuts. And as soon as I hear myself say that’s nuts, I might Tim Ferriss, you know, brain goes off in the back, and it’s like, okay, so go try and do it. And I did. And I was in my mid 30s, I was feeling like I was my metabolism was slowing down, and I was really sluggish. And so I just said, Okay, I’m not going to eat between midnight and noon every day. It’s I’ll make it to noon, Holly. And this was also part of like, I don’t know about you, but I’ll get to the middle of the day. And it’ll be like two or three o’clock, and I’ll be like, Oh my god, I forgot to eat because I was so heads down and work or I was running from meeting to meeting. And so trying to solve for those two things. I put in this intermittent fasting, the only thing I’ll have between midnight noon is water and like coffee. And that ended up sticking, it’s helped my energy level, it’s helped me lose weight. It’s obviously helped ensure that I eat in the middle of the day of when I need it. So I block off time for that, because it’s important to me. And I’ve been doing that for I’d say at least three years now.

Will Bachman 17:45
And do you find that changed what you ate as well?

Braden Weinstock 17:50
Absolutely, absolutely. I mean, at the end of the day, you know, just stopping the the eating in that time period doesn’t solve the problem. But as soon as I am ready to eat, it’s usually a salad with a protein. Or it’s some kind of nourishment that I’m like, you know, really excited to have. So I started caring about my lunch a lot more. I used to be the kind of guy who’d like go into the lunchroom and get leftovers from whatever, you know, catered event was going on or just go downstairs and like, get tacos or something. But because I knew like at noon, I am going to be hungry, I have 30 minutes blocked, I’m going to eat I started bringing lunches or pre planning and so I put more thought into it. It’s kind of like I would say a secondary effect.

Will Bachman 18:41
Let’s talk about some of these other operating practices. So maybe let’s jump to time blocking and deep work. which you’ve already touched on a little bit but elaborate a bit on the time blocking and, and on the deep work practices that you’ve put in place.

Braden Weinstock 18:57
Yeah, well, I mean, my hat’s off to Cal Newport for really helping me think through this and better way. But I’ll say it started when I was working at Bridgewater associates, which, which for people who don’t know, it’s the world’s biggest hedge fund founded by Ray Dalio, who’s got a set of principles that are quite unique for operating a culture. And I was chief staff to the head of the portfolio management department that oversaw the execution of Bridgewater investments. And I was in the beginning underperforming and my solution was just to work more like I would not go home I would work till 3am, etc. And most of it was because as Chief of Staff, I’m in a meeting from like 8am to almost 8pm like non stop. And then I also have to do my own work to like follow up on all the threads and then I’m running special projects on the side and I just simply did not have enough time and I was getting burned out. And my, my executive just said to me, he was like, you need to learn to work smarter, not harder. You can run through any wall. But sometimes you need to know when to go over or around the wall. And I was like, Oh my god, I’m sitting there at three in the morning in the dark computer screen in my face. And I’m like, how do I do this different. And so I luckily stumbled upon the deep work and some other classics of manager versus maker. And I started shifting my time, I just said, Okay, I’m going to start doing some time blocks. And that way, I knew exactly what I had to get done in a specific time. Previously, what I had done is I let my calendar control me, people would throw time on my calendar. So I started saying no, because I have this time block to get that work done. And I wouldn’t just like put a block on that would say, block, which is something I feel like a lot of people do, and I used to do, I started to be very specific, I have an hour to write this deck, I have a half hour to process emails, and so on. And by forcing myself to visualize how I spent my time through time blocking, I was getting better at making sure I was getting stuff done. And then I noticed, well, there was maker versus manager. And I was looking at myself going okay, most of my works manager, but I had to have all this maker work, like I have to sit down and build decks, I have to sit down and build plans, I have to sit down and review content. So I started creating bigger chunks of time. And what I noticed is if I do it in the morning, I can crush through like really deep work. And something that used to be a deck that I would kind of dabble in all week when I had 30 minutes would get done in just like one sitting and my cycle time for producing work sped up. Because normally what I would do is say okay, that thing is due Friday, I’m going to start on Monday, I’m going to dabble in it all week. And by the time it gets a Friday, I have like a draft version reviewing. Instead, I would just put something on for Tuesday, sit down for an hour. And I’d be like how do I move the ball 50% forward, I’d crushed through that. And then I’d let it sit or I’d share it with someone get feedback on it. And the cycle of getting to what the end product would be would be faster, and the workload quality would be better. And so I started to utilize these tactics, visualizing visualizing out my time blocks, and making sure I distinguished when I needed blocks to get deep work done. Rather than thinking I can jump from meeting to meeting and have half an hour in between to like spin up a deck on something

Will Bachman 22:43
amazing what this sounds like, again, textbook, deep work near al talks about it and in his book in distractible. I’m talking about email processing. That’s another one of your operating practices.

Braden Weinstock 22:58
Yeah, so you probably notice a theme here. And and I think it’s really important. I don’t think the things that I do are special. I think the things I do are known things that are proven to work. But people don’t often go out, learn and put the time, effort and discipline into executing. I really think learning from others is a valuable ability to do and so you know, I picked this up from from Cal, but there’s the classic like email processing system from for getting things done. And same thing, I felt like you know how social media stuff is popping up on your phone all the time. And it can, like inundate you and it’s overwhelming and it constantly feels like everything is almost in chaos mode, and it never stops. There felt that that?

Will Bachman 24:01
Well, I certainly felt like chaos mode, I pretty much turn off all notifications and i and i don’t do Facebook or Twitter anymore. But I know what you mean.

Braden Weinstock 24:10
Exactly. So you’re a step ahead of the game. That was pretty much how I felt about email is it would never stop it was just a flood of noise. And so I couldn’t develop good routines and focus on my priorities, or effectively time block in order to produce deep work if I’m constantly being inundated with email, and so I set up basically a time block in the morning to process email. So what I do is, you know, I talked to you about like I get up in the morning I do my morning routine. If I’m going to the gym that day, I go to the gym. I do not look at email until after the gym. I do not wake up in the morning and go through my emails. I put a half hour block on and the first thing I do when I sit down and get to work is I crusher my email, I’ll usually check something in the middle of the day, like at lunchtime and see if there’s any high priority things. And then towards the end of the day, I actually do a wrap up, or I’ll do processing on things that I need to get set and moving for the next day. And so two things are important out of this. First thing is, I’m able to not be inundated focus on, you know, when I’m in a meeting, doing a one on one, I’m paying attention to my employees, if I’m in a meeting, solving a problem, I’m giving people my attention, and learning and listening and collaborating with them. So I become better as a manager, as a leader and as a person. The second thing is, you’d be surprised how many things saw themselves when you just let an email sit. And that takes the stress off myself, it empowers others to solve problems, and more gets done. It’s kind of a small tactic for getting leverage.

Will Bachman 26:02
That’s another one of your operating practices. In what ways have you gone out to get leverage?

Braden Weinstock 26:10
I think when I was early in my career, my only solution for solving problems was to look internally to myself, and see what I could do that solve things. And that was a mindset. And the first thing that changed was changing my mindset to get leverage, which is, wait a second, do I have to do this thing? Or am I just responsible for this thing getting done? And then the second thing became, do I have to build this? Or can we buy this, if I can buy it, well also means I can outsource it. So that’s another form of getting leverage, then I started managing things. And as I started to manage parts of organizations, I started to think about, okay, do I have to just give this to a person or a team? Or could I decompose parts of this process or machine across different parties in a way that gives leverage to actually getting the job done? And so one of the first things I always try to think about is, do I have to solve this myself? Is there somebody else who can solve it? Or am I responsible for it just being solved? Can I buy or build it? And if there isn’t one single person to do it, can I decompose this and spread it out across others to get it done, because ultimately, at the goal level, the objective is the thing is accomplished.

Will Bachman 27:40
And then I’d love to hear about texting versus talking.

Braden Weinstock 27:47
So just to date, myself, I mean, like, I had a pager in school, and then I got a cell phone had old Nokia. So I am exactly on the cost of two generations. And I do tax. But one of the things I noticed, texting doesn’t, texting is okay, for quick information. What it doesn’t do is communicate to another party, much of what we get when we talk to somebody. So 70% of your communication is verbal, and gestures. So all I’m getting is like quick snippets. And a lot of that would mean that the effectiveness of engaging with somebody building a relationship learning the speed at which you can ask questions and exchange ideas, that kind of conversational engagement is suboptimal in texting. Whereas talking, I can quickly ask you a question that I can go, Oh, I’m, I’m off on something here, like, what am I missing? Or I can quickly engage with a question. And so ultimately, at work, I started to notice, I get better results for conversations by talking, not having text conversations. Texting is really good for quick snippets of informations, it doesn’t convey emotions well. So I really wanted to make sure I knew when to use toxic talking and when to use texting in order to solve for different things.

Will Bachman 29:26
Let’s talk a little bit about some of your some of your consulting work and some of your executive work. So after Bridgewater, I think that you were you know, you helped knotel grow. Tell us a bit about that experience at Notel. And maybe just for listeners who aren’t familiar with it, give it give listeners a quick overview of what Notel is. And that’s k n o t l like knowledge hotel. Right? Right.

Braden Weinstock 29:54
So, actually, after I left, Bridgewater ended up doing freelance consulting and I was doing With a variety of different startups, ad tech, and some others, and I actually started at knotel, which provide flexible office space, full floor solutions for companies It does. It manages the lease, the build out does the fit out, and it has a subscription model for for rent, essentially, it also does your it. So, at the time, it was like a 25. Person startup just got it series A, and it was, it was like a hacky version of, we had a full floor with two companies that shared it. Instead of we work where it’s like a small couple people in a box. And the idea was you graduate from co working into your own office, but you don’t have to take on all the responsibilities in the long term lease risk. And my very first thing was run the sales team. Okay, what’s wrong with your sales team? I don’t know. They’re not hitting numbers. So I started going in and looking at some of the basic components. And what I saw was, people just didn’t have like, the frameworks for understanding what a sales lifecycle was, the tools weren’t set up, nobody had the metrics. And so if you just kind of sat down, and put the process in place, and kind of walk people through it and hold them accountable to working on it, we made improvements. And obviously, when you’re building a startup, you know, there isn’t a lot of structure. So being able to add structure to things, but not too much, can be really helpful. So I ended up joining full time as director strategy and building and running a variety of things. So I started building and standing up customer success and revenue operations, and then it’s like implementing CRM, and then it’s implementing construction project management tool. And then it’s like, well, wait a second, does our entire process work? I don’t know. But we need that thing to work. Because that’s core to how much we invest in actually acquiring space that’s core to our unit economics, which is what we’re fundraising on. And the faster we can do that the better. So like, how do we figure out how to improve those things. And I got to bring a lot of my consulting skills to the people processes and technology, of how we actually executed our business, and be able to build at the same time that we were blitzscaling. And over the three years, we raised over half a billion dollars, we scaled from being just in New York, to 12 cities around the world, when I started, we had about a quarter million square feet. At the end of 2019, early 2020, we were about 4 million square feet and had closed our series C at a $1.5 billion valuation and 500% headcount. So in three years to grow from 25 to 500, and quarter million to 4 million square feet around the world, you’ve got to build a lot, and you got to build a lot fast.

Will Bachman 32:53
What were some of your key learnings from that experience?

Braden Weinstock 32:59
Well, there are a couple of different levels, we could talk about that the first I would say is the importance of culture. You know, obviously how a business is led, and its ability to solve problems and move very quickly, is critical. And the pace at which you’re bringing people in, you know, 20 people a week almost, it starts to dilute your culture, and you got to figure out how to keep that culture healthy. So I learned a lot about that, and the failures of what a lot organizations don’t do. And as a result, their culture gets diluted or becomes a lot of internal politics and fragmentation and stifles not only problem solving and innovation, but also just your ability to execute well. The second thing is, I learned a ton about like, you can let a lot of fires burn. as a consultant, everything I felt like had to be perfect. But when you’re moving at that speed, you can make this trade off between speed and efficiency. And you can actually let the quality of some things slip lower than what I was used to as a consultant for Fortune 500 companies. And it’s just fine. Another thing I learned is due process, automate. You have a problem. My very first step was like, okay, person, you own that problem. Go work on that problem, figure out how to make that thing work. Here’s what good looks like. And then once they start to put that together, and come back and say, Oh, you build some spreadsheets and you have a few steps. Okay, let’s document them. And let’s see if we can with the idea of leverage. Let’s see if we can spread that across a couple of different teams so that it doesn’t have to be a full time job for one person and we can be allocate resources. Now that we got a process and that process is replicable, and we can start to scale that across multiple people. Let’s start to automate that thing. So that we can get it off everybody’s plate. That was incredibly important tactic for being able to build at speed. And ultimately, I also found that like, when you’re in a startup, and you start very early, the pie is growing so big, and things are moving so fast, it is natural, and it is okay for people to get talked. And this is something I think a lot of people don’t talk about in startup land. But I’ll see people who like, I’ve never been a manager, you know, first few years of their career, all of a sudden, they’re managing a team, and they want to be like VP, or head of x, and somebody gets hired in above them, and they get like, upset. And ultimately, what you did in that early stage is super valuable. But it doesn’t mean you’re necessarily the right person to run the next version of the thing. And one of the things I think about being able to grow as a person is have the knowledge and humility of like, Where are you in that phase? And what are you going to learn from somebody else more experienced coming in, and you working to help make that person successful, makes the organization successful, more opportunity, you have to go do other things in the organization. So I built the first version of the customer success team. But then I ended up also working to like, hire somebody to run that entire team and build it and grow it. What I did though, was I put the foundations in, I hired a few people, I set up a plan for where I think we needed to go. And then when we brought that person in, I helped onboard that person. And then I went on to build two, three other teams. And I really enjoyed that, you know, running multiple teams. But I didn’t feel bad about the fact that I didn’t stay the leader of that team. And I think that’s a really important lesson for people to have in startups.

Will Bachman 36:59
Tell us a bit about your practice. Now, I understand that you do some work as Interim Executive, you do some consulting. Talk to me about what you’re engaged in these days.

Braden Weinstock 37:09
Yeah, so I really love helping people. Like at the end of the day, my purpose in life is to improve how things work, so that it makes other people’s lives better. That’s the simple goal. And so I noticed that I had these experiences in building and scaling organizations and or transforming organizations. And so oftentimes, I’ll be joining an organization as our Interim Executive, and like a CIO, and coming in and putting in performance review process sees career matrices, organizing the executive team around okrs, setting up regular budgets and planning cycles, and ultimately helping to build out their hiring processes to focus on how they actually operate. Sometimes they don’t have culture, documented, and nobody’s really thought through how they actually behave in order to onboard people successfully. So I might put these kinds of structures in place in order to really help either the founders or leaders of organizations evolve from what I would say, is typically like a nascent adolescent stage, into a more mature stage. And one of the reasons I think it’s good to do this in an interim capacity is my, my stake in the game is to make other people successful. It’s to improve the teams lives, because how the business operates is better. So oftentimes take CEO roles in that capacity. Another thing I often do will come in, and I’ll actually just work with an organization on particular function and partner with an executive by doing a diagnosis of operations doing diagnosis of the people, sometimes I’ll even step in and help lead like in a large transformation effort, maybe they’re, you know, revamping their CRM MRP procurement function and need to help with guiding vendor selection and teaching people how to write requirements and making sure that they have good gating mechanisms. But the organization needs to learn. And I have a particular ability to to go from the like, conceptual to the practical. And so that helps people be able to do that, and alleviate time, stresses from from the executive meeting it and so oftentimes, I’ll do that. Sometimes. It’s just as simple as like coming in and doing some executive coaching or doing a talk to an organization and doing some training with them on. Here’s some mental maps for how you can operate better together. So for example, maybe we want to talk about how to give people instructions as a manager by telling them this In my opinion, as a person, this is my strong suggestion as a leader, or this is a mandate as the boss can be a small tactical thing that changes how people’s relationships with their managers are getting done. I also do some work on teaching people how to have great one on ones, I have five very simple questions that I do. And by coming in and teaching people how to run a one on one, they get better at actually managing the organization and producing better results. So these kinds of things.

Will Bachman 40:34
Oh, I got to ask, what are the five simple questions?

Braden Weinstock 40:38
So every week, I have people say, number one, how are you feeling? one to five, one being terrible, three, being neutral five, being awesome. Usually, the first thing people are like, well at work, or life or whatever whole point is just like how are you? Because you are a whole person. And that usually leads to me like digging into limit. Number two, what did you accomplish last week? You’ll notice this is not tell me the tasks? This is what is the goal? And what did what is the outcome you produced? Number three, what are your goals or objectives for this week? So where where are we? Where are we going? And this usually creates an opportunity for them to say, Well, I’m thinking through it like this, or I need some help from you. And so my fourth question is always, what do you need from me, ultimately, as a manager, as an executive, my goal, my objective, and my responsibility is to help others be successful. And the fifth thing is, is there anything else to discuss? Because I always want to create an opportunity at the end to ask people what’s on their minds, it might be something that’s going on in their personal lives, it might be Hey, I want to plan a vacation. It might be I heard such and such politics, what’s really going on? And if you don’t actually take the active step of creating the safe space, how are you ever going to build psychological safety, to be capable of leading that person to being great, and actually growing as a person? And so that’s the last question.

Will Bachman 42:16
Wow, that sounds like a good set of questions for one on one. So I’m going to include a link in the show notes for your website, Braden ww.com. That’s BRADN WWE comm where listeners you can go and go to the about page, you can check out Brandon’s operating system, the full detailed description of it, Brian any other place, you’d want to point listeners who want to find out more about your work?

Braden Weinstock 42:45
I think the website’s great. Obviously, I’m on LinkedIn, but people can read in, get a hold of me through the website. And so I look forward to hearing from people.

Will Bachman 42:53
Fantastic. Well, Braden, thanks so much for joining today. Really enjoyed the discussion. I’m inspired and motivated now to work on my own operating system and to get some of my own habits and routines. Enhanced. Thank you so much for joining today.

Braden Weinstock 43:10
Thank you for having me.

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