20. James Kaikis on Letting Go of Control

James is an entrepreneur and technology professional who is currently the Chief Solutions Officer at Testbox , a technology company that facilitates business-to-business sales of software and operating systems . In his role with Testbox , james spearheads company efforts to enhance the customer experience and align products to their needs and interests .

James is also the head of GoToMarket and founder of GTM Shift , a platform designed to enhance GoToMarket strategies of businesses so they are aligned with the evolving journeys of modern customers .

Previously , james founded the Pre-Sales Collective , psc , a network dedicated to making tech jobs more accessible to people from all backgrounds , for training , education and mutually beneficial relationships . He successfully grew PSC to 35,000 professionals globally before selling the company to pursue new opportunities .

He serves as a strategic advisor and limited partner for a variety of companies and funds , including Poverity Quilt , gtm Fund and Stage 2 Capital . He worked in solutions leadership at Salesforce and as a contributing early , pivotal member of the solutions team at Revenate and Showpad .

James received his bachelor's degree from the University of Nevada , las Vegas , in education , before going on to earn his master's in sports sciences at Ohio University . James , thanks for joining us today .

It's all about execution and when you focus in on those details , they compound and lead to separation and execution , and I think that philosophy has done well for me . However , if I think back to early in my career , I think probably the word micromanagement will be something that people would have known me by with good intention .

And I look back at myself and I look back at one experience where I had been at a company for a couple of years . Back at one experience where I had been at a company for a couple of years . I was one of the first US employees early stage and grew my career there pretty quickly .

I was hired as an individual contributor , promoted to a leader within three months and then grew out a team over the next couple of years . I had actually just come off winning one of the Employee of the Year awards . My team was incredible . They were known within the organization for being extremely stellar .

And one of the executives pulled me aside and said James , I think you're doing an okay job . And I was pretty taken back . I remember this leader saying well , you need to act more like this person and this person . And I was flabbergasted at that time . I was like what do you mean ? I need to act like that person and this person .

And I was like flabbergasted at that time . I was like what do you mean ? I need to act like you know I'm . I'm way better than these people . I act way better . And this leader told me James , I think you're a great principal individual contributor . I think you're really at the at the top of the game there .

But when it comes to manager , I think you're lower on the schedule uh , on that lower on that schedule . When you call yourself a director , I think you're even lower than that . And I'll be honest , I was so taken aback by that . I was actually very upset for years really .

But when I look back at my career now , I had so many really talented , smart people in my organization and I spent too much time meddling in the details of what they did every day and how , and you know what I thought was trying to help them was actually probably stunting their growth and for themselves as leaders .

And while you know a lot of those people loved working for me , I probably didn't help them elevate as well as I should have . And so like that is like the one experience I look back on and I think , wow , at the time I absolutely didn't agree with it , but now I'm like , ah , I know exactly where they were coming from .

I used to be one of those people that would you know , hey , I'm on vacation , but never take a vacation type deal Right , always available , always online . Um , until my daughter was like dad every time I were on vacation .

You're always working Right , and it took her bringing this up to me , and so I'll never forget that I went on vacation and delegated a week's worth responsibilities to one of my employees and guess what ? The business still ran . The business was just fine .

Sure , there was a couple of fire drills , but the team handled it and , truthfully , they needed to be in a position where they could handle it to the expectation that I would have wanted us to handle in that moment . And so I think those were like places that it started .

And I will say , because there's plenty of things I can reflect back on that experience I was such an early person in that company that I knew everything right . I knew everything about the product , the buyers . I was very influential in our growth .

The company was like $1 million in revenue in the US when I started and when I left we were closer to 76 , 77 . So we went through tremendous , tremendous growth . But it took me having to leave that company and go somewhere else to be like all right , I'm starting new and how do I want to define my leadership abilities ?

And actually the company that I went to a very , very successful company . They wanted their managers in the weeds like that , and I was like no , I'm going to do things differently . And I did things differently very successfully , and I think that was an impetus to like taking this next step in my career .

So when you did push back , did you get flack for it and how did you message or communicate that ?

So like , for example , at the time the company was still growing really well , there wasn't a lot of employee attrition either , and so there was like a way of doing things and everyone at that company got like a certain certification in the product , like even the managers , and so one , they didn't really hire this division , especially didn't hire managers from the

outside . It was a lot of promotion from within , and so like , hey , you need to get this training . And I was like , why do I need to know this training ? I don't need to do this Right . And I pushed

back . And then there was a lots of other things . Like there was sales leaders who were like James , I'm used to so-and-so , like doing these demos and doing these calls and being super involved , and I was like , well , that's not my style .

Like I'm going to let the people who are way better at me than this , than me , do this job and I'm going to support them . And I got a lot of pushback at first . However , I'm a big like put my money where my mouth is person , and I want to lead by action and not words .

And I actually had some of the best employee satisfaction scores in the entire business because I ran a model and a philosophy that was bucking the trend and different than anybody else , and even though I was only at that company for 15 months before I ended up leaving to start my own business , I had a number of executives that gave me really good compliments

that I really hold very valuable still to this day , where they were like 15 months of James in our business was so impactful that we would do it again , and I think my hope was that some of my other leaders around me , even my , my superiors learned from my approach and realized , oh , there is a little bit different of a way of doing things and not to

belabor the point right , but like , one of the things that is just so important to me is this concept of like raising the floor and raising the ceiling right .

I actually took on some employees that I was told were underperformers or potentially not fits for the business , people that were making career changes , and I've focused on setting these people up for success and some of these people went on to win quarterly awards , do super well in their career , are still in the profession after making a pivot , and I could talk

more about that in detail , but that is what I learned in that moment is my job as a leader , and I look back at my conversation that I mentioned earlier and was like , oh , that's what they were talking about Now . I also believe that as a leader , you also have to have your pulse on things .

So it's a very fine balance and fine line of understanding how you empower your teams , but you also have a point of view to gain their respect , to offer them guidance and to help make them be able to reach that potential . It's not easy at all .

And when I was at a previous company that had a lot of domain expertise , I realized that a lot of these people didn't know the technologies , but they were subject matter experts and they could carry a conversation and they could build credibility and trust , and so that's something that I've always tried to be able to do .

I've even had conversations with people that say , hey , I just hired a bunch of smart people and I got out of their way Right , and sometimes that's really successful .

But sometimes that results in what I like to call hero ball right , where you just like have some really top performers that are just executing and doing things so well that it ultimately like makes you look good and you don't necessarily have to put in so much work .

It's harder to go and focus on the middle performers and the lower performers and make them better , right . So , um , a lot of things that that I have done is it can be very circumstantial . Right Is having a point of view , asking the right questions , and a lot of times , people say you know you got one mouth and two ears for a reason .

I agree with that in some circumstances , but I also agree at other times that , like you sometimes need to use your words to push people in the right direction .

I will , you know , have a project that I want to lead and , like I think it's what I'm really good at now like even better than I was a couple of years ago was like this is the vision that we need to get to , and these are the reasons that I think that this is important and these are some ways that we could get there .

I'm curious on how you're going to paint the picture right . My job is to like draw the outline and have my team paint the picture , and sometimes they might like overdraw my outline and make something even better , and that's what you're shooting for , right ? You don't ? I think . As a leader , my goal is to not always start at zero .

I'm trying to give people something and some place to start at and also focus on the outcome , more so than I did previously and earlier in my career .

I want to go back to what you said about underperformers , because I think a common trend is , if someone's underperforming , you have to tighten the leash , not give them more room , but what I think I heard you say is that you took the opposite approach . Did I hear that right ? And if so , can you talk a little bit more about that ?

Do they have personal things going on ? Are they struggling to grasp concepts at work ? And the best way to learn on that is to not necessarily , like you know , overburden this person and put more stress on the situation . It's actually to get in the weeds with them , but alongside them and just understand how they're doing things .

Because you'd be so surprised what you as a leader especially if you're fairly senior and you're pretty hands-off you have the outcome and you're like , oh , this person's getting there . But when you go and learn how they're getting there , you're like , oh my gosh , there's so much opportunity to improve and dial these things in .

So that's why , again , I go back to the point of view and dial these things in . And so that's why , again , I go back to

the point of view . But there was one employee that I managed that I was told was an underperformer and that they probably weren't a fit for the business and I was like , all right , I'm gonna figure this out . Before I take their word for it , let me go figure it out .

And when I went and got side by side with this person , I realized how inefficient they were , how poorly they were doing things on their own end and that was ultimately resulting in the poor outcomes with salespeople and our customers .

And so what we actually did was figure out how to like , build more process , build a little more organization , streamline their efforts , and then that gave them a little bit more bandwidth to go focus on other things and they were able to turn their performance around . And you know I am proud of a number of turnaround stories in my career .

You know I actually used to teach when I had my own business , a leadership training for people in the solutions engineering profession , and I built out a program called Leader Elevate .

And it was this concept of like first-time leaders like how do we make you better at your job and would spend a lot of time talking about , like how I've used performance plans or PIPs actually to my benefit . A lot of times you're like , oh , I'm getting a PIP , I'm gonna I'm out of the business .

No , if you use that effectively , it can be such a great tool and a motivational tool . Oh , I'm getting a pip , I'm out of the business .

No , if you use that effectively , it can be such a great tool and a motivational tool If you are again alongside that person , helping them be successful , improving out that you're gonna make them successful , and let them see like , hey , this isn't a way to get me out of the business , it's a way to improve my performance .

I've used those pretty effectively in my career and I still have people to this day who thank me for putting them on a pip .

I think most people have good intention , they want to do a good job , but they're not always self-aware of how good of a job that they're actually doing . And so your job as a leader , as I talk about the raising raising the floor and raising the ceiling is to set the standard of expectation . This is what we expect .

This is the standard of the floor , right , I would never call it the floor to my team , but , like , this is the standard and this is the standard you're going to be held to and I expect you to do .

And if you want to over-perform , these are the things I want to be able to see and give people that roadmap , because you , as a leader , if you're going to let people lower your floor , it's a tough thing to allow to happen , right , and it's harder and harder as your orgs get bigger and bigger and bigger .

And so setting that standard across , I think , is important , and something you asked about earlier is when I was at one of these companies and the standard was be in the weeds , like some businesses and some divisions were not like that at all .

And so like an operating framework of like what do you expect changes of are of a team lead and a first line and a second line and a third line actually can really help people be successful in their job .

And one more thing I'll throw out here is I've always had the philosophy on the frameworks that , like I want frameworks and structure to help people do 60 to 70% of their job , so that , like they can take the creative freedom to do the 30 to 40% . And that's where the magic happens .

And I think , as a leader , like the repeatability helps you find efficiencies and helps you be able to do more when you know that there's a certain standard or a certain expectation in that 60% .

He really talked about the importance of micromanaging the process , of of learning what they do , how they do it , and I and I take that , as you know , figuring out the tools and resources they need so that they can be more efficient , and finding ways that you can not be critical or attack them but to support them , and knowing , as the leader , what tools do

you have at your disposal , not just your experience , but a performance plan , and figuring out how to motivate them . Those are kind of some of the takeaways of the underperformer management comment you talked about .

You know , there's things you could do like a buddy system , right , you like pair one of your underperformers up with your top performer so they can understand and see how these people do these things , and it's like , oh , there's a little bit of like peer-to-peer pressure there .

Um , I think I have done well in like finding mentors and coaches and like people that they can talk to within the organization to just have another outlet .

And , um , you know , also like using learning and development , like for , for example , like , the reason why I created my Leader Elevate program is like , you know , I reflect back on the story that I said is like I wish somebody gave me a blueprint on what I was supposed to do as a leader . I thought I was . You know , I always am trying to lead .

You know , lead from the front , right . I'm always trying to like be boots on the ground , right , but at the same time , I've got to be in the helicopter above the team and you've got to know when to be on the ground and when to be in the air , and no one ever taught me that , right , I was just kind of playing hero ball , as I mentioned earlier .

So , again , I think that there's a lot of tools , but the peer-to-peer thing has always been one of my favorites . But I will tell you , I'm a manager that I like to have , like again lead from the front but like have empathy . If I find someone who's not a fit for my business , let's have a transparent , open conversation about that .

And maybe you're a really good employee but you're just in the wrong role , you know . Maybe you can move to another role within the organization . I have helped people on my team go and get jobs at different companies , right , that is very important to me because I will have relationships with these people far beyond the companies .

Right , I think about even my own company , that I don't even work for my own company anymore and it still exists , right , there are still relationships that I have there and have made from there .

So I think being a person first is important and just trying to do what's best for the individual and having good intention there is great and there's a lot of tools , but those are probably the main ones that I like to lean on .

But taking a moment to figure out what's going on with them , are they dealing with something ? Is it a motivation thing ? Because , like you said , nobody , nobody wants to come to work and and not be good at their job said nobody , nobody wants to come to work and and not be good at their job , totally , totally .

Right , you know , we're more like birth of a new child and really adjusting to that , right , um , and I think , like understanding that we're all humans at the end of the day , and like there are some people that are more open about what's happening in their personal life and there are some people who aren't .

And I think you might ask , well , because I've always I want to love to talk about , like , culture , feedback , right , like I'm anyone who works for me , I am very transparent , maybe sometimes to to to a fault , but I just had a new employee start my business a couple weeks ago and they're like James , I have never met a leader who is this open about things

, because it's important .

And you , as a leader , if you have an employee and I've had employees that work for me that never want to tell me anything that's going on in their personal life , and I respect that but if I know and observe that something's going on , I need to open the door to be like hey , I'm observing this , something's going on with your performance .

You have an opportunity to tell me , if you need to , if something's going on at home that I need to be aware of . And I've had employees that didn't tell me and unfortunately we moved on from them because they didn't open up and like say they needed the help and I would have been probably more empathetic to help them .

But if they're like , hey , nothing's wrong , I'm just doing a poor job at work right now , you know you can only help somebody so much and obviously that's not an easy conversation to have . But yeah , as a leader , you need to be able to create that culture of feedback and a place . And look , it's easier said than done , it's still easier .

So then you got to be able to create a place where people can feel safe to talk about these things . And you read about these things all the time but like , how does it manifest in a day to day , right ?

How does it manifest when you're in that conversation where someone just like really messed up a call , really messed up a deal actually lost a deal for your business , and you're like what is going on , right ?

So that , I think , is just important to me and you know , like my goal forever and has always been like to make an impact and I want people who ever worked for me to be like , damn , james was one of the best managers I ever had , right , or if I wasn't , they learned something from me and like I know what .

I don't want to work for Right , cause I'm not an easy person to work for , but some people love working for me Right , like that's . That's just the reality of the situation .

and I , you know . I want to go back to , because , with empathy , what I heard you talk about is there's a point where you can be empathetic , but that doesn't excuse poor performance , especially if people aren't willing to be open .

And I , you know , I'm glad you said that , because some people say , well , you have to be empathetic and and just support your people through whatever , but as a professional , as a , as a organizational leader , you have to get results .

You're paid for results , and so I'm glad you talked about you know , we can't just support everybody forever if they're not willing to 100% . You know performance isn't there . Is there something you can get from me ? And they say no , Well then they better turn performance around on their own .

It's you know , it's interesting to hear you talk about this balance of culture , of feedback . Of you know setting the floor and a phrase I like of you know what you excuse , you condone .

It's a lot easier to just let it go right . It's a lot harder to have a hard conversation with somebody to put them all on a pip , to actually exit them from a business .

So one of the things that we used to do at my leadership training is like we had this thing called the hot seat and we put people in like role play scenarios and I've actually made people essentially fire me . And then I have a family , I have bills and I've actually had people like tear up because they're like , wow , this is emotional .

I'm like this is real life , you know what I mean . And like , yes , you want to be empathetic , you want to help people , but a job is not . You're not entitled to have a job , right ?

You're paid for performance , you're paid for a reason and obviously you want to have balance there , but you can't just show up and expect to get paid and expect to get your bonus by not putting in the work , because there are other people out there who deserve the opportunity to put in the work .

If you're not and I think as a leader , you're only as good as your , as your quote unquote worst performer , right , you're only as good as that that person .

So you know , especially in a bigger organization , my goal and what I used to teach people on is like you need to make sure that your entire team is quote unquote better than everybody else's entire team and you could still be collaborative in that environment .

But like you should always shoot to make sure that your bottom performers are middle performers or top performers compared to other teams . That makes a big difference in terms of output and action . And we used to teach about power rankings of employees . Especially with a lot of rifts and layoffs that are happening , you ideally want a team .

You got 10 people on the team . These 10 people are better than 75% of the 80 other people within the same organization . So I don't know Again a lot of things there , but you got to lead from the front . You got to put in the work .

It's not easy , but you're here for a reason and you're working for a company for a reason , and you can't lose sight of that .

So it's is , you know , it's it's letting go of control but but really it's just controlling different things and making sure you're controlling the right things . Um , is that a fair ? Is that a fair observation ?

Yeah , I like that observation a lot because you know again , I think if you let go of control entirely , you get to you're , you're become that ivory tower leader that I think people don't love working for , right , you know , and I think you nailed it Right there's , there's , there's control of some things and there's no control or low control on some others for

sure .

Actually , most of them have worked for me before , so that's always good , and a number of them are net new to the organization and I think early on it's setting the standard so that they understand what it looks like and these are the things that we demand and letting those people do their best work .

I mean , I've got a couple of employees I have just been blown away by because I'm like this is the standard . These are the things that we do around here . This is why we do them . Again , there's some places that like , if they need help , I can jump in , I can get into the details and I pride myself on being able to help them navigate through that .

But especially in this job , because I've actually decided to build a flat org structure , so I have a lot of people that are directly reporting to me at all kinds of levels of seniority . It has forced me to like , really , really empower people , and that's what I wanted to do and that's what I'm doing intentionally .

Even my , my founder is like wow , like you know , like , are you sure you don't want to build leaders here ?

I'm like no , right now , while we're figuring this out and retooling this organization after pivot , I want a flat work structure and so , like , that has forced me to set more expectations , focus on the outcomes and focus on empowering people and a little bit of like , almost like a project manager , I feel like I'm almost project managing people a little bit more

to make sure that they're delivering . But let me bring something up right . So I'm sure we'll talk about my own business , but , like when I left my own business , I wrote a letter to the community and one of the things that I focused on was I learned that people have , ideally , either a high quality work or speed of output .

It's very rare that people have both . I believe , personally , that I have learned how to have both and , as a leader , I need to make sure that my team can do the same thing , because I've worked for people and had employees on my team that do amazing work , but , wow , they take too long to do it .

They become almost perfectionists and it actually is detrimental to business . I have some people who work it . It actually is detrimental to business . I have some people who work really , really fast and then have subpar quality of work . So , like , how do you balance those two things out ?

I think that's like a critical skill of leaders in terms of like when you , where you get in , when you get in , how you get in and then how you empower is in a day , like you gotta be focused on the outcome and that's the biggest thing that , as a senior leader , you can hone in on and make part of your DNA .

Like that's the thing I talked about I haven't really brought up yet , but like everything's about cultural DNA . Right , you can't just say things , you have to act on them , you have to make them part of everyone's operating and I think that , like early stage expectation setting and details will help people get there .

We we do some things , especially around like our customers , and so I have a new employee who's got amazing experience from big enterprise consulting company and I need him to get into the weeds and learn these things .

But what we talked about yesterday is like , if I have him out there leading some of these things and things don't go according to plan , it brings risk to our customers and risk to our business and , more importantly , risk to their peers . This is something that I think people really underestimate , that I have been very good at navigating my career .

If you put someone in a situation to fail and you put them in a situation where the failure is detrimental , you're gonna spend the next three to six months rebuilding trust of that employee with their peers .

I like to work behind the scenes as much as possible , so like prepping people one-on-one and be like hey , this is what we're going to talk about in this team call here , earlier internal team call , this is what I need you to do .

This is the outcome I want you to have , and then having that person start to raise their voice , give their opinion , talk about these things , get more comfortable , and then we put them in situations where they can succeed right . And then we put them in situations where they can succeed right , you're managing that risk .

Or they could fail , right , or they could fail . If they succeed , it's a checkbox that accelerates them forward . If they fail , they learn and you let them know like , hey , it's okay , you learned it wasn't detrimental to the business , and so it's always about risk and a risk assessment .

Now , that being said , there are situations you're going to put people in where , like , the chances are they're going to fail , and sometimes you're okay with that and sometimes you want that to happen .

But there are sometimes high stakes , situations where the likelihood of failure is really high and so , like you , as a manager , can do everything you can to like set this person up for success . You know , micromanage the process .

But if they fail , you need to understand the repercussions of those actions and how you risk mitigate from there and then build that person up so that they make sure that they learn they know what they're going to do better next time . And then we move on .

How do you assess risk , which implies an element of not having control .

And so , you know , when you look at like my peers , like I'm probably more risk on and letting people fail in environments and other people are who are like , hey , like we're , we're less , we're more risk adverse and we're not going to let people do these types of things

. I think you know I'm a a big proponent of like Gallup , strengths and strength training and these types of things , and one of the things in my top 10 is is is individualism Right ?

And so I've learned that , like you know , you can still set the standard and then you handle a lot of people in situations individually , and so I think , again , this goes into like it takes extra work to do these types of things .

And you know , I wish I had a better answer , a more clear answer , but I think , again , I'm more risk on and I'm just assessing the situation at all time Like what's the worst case scenario ? What's the worst case scenario ? What's the outcome ?

Right Like I think I didn't entirely know how to use these things right , how to use these tools , but as , as you know , as we continue to talk , like a focal point for me in my career is like how do I take my strengths and make them superpowers , right , like , how do I make them ?

You know , places where I can lean in , and I think this has become one of those places is like I can , I can again , I can be , uh , 30,000 feet up in the air , but I could be right on the ground , right , and I could be dangerous in both of those situations , and that's like a prideful point of me as I continue to grow throughout my career .

I want to continue to make an impact . I have always been a person who wants to do a lot right . I want to continue to make an impact and I actually was . Well , the genesis of my business Pre-Sales Collective was that I was in San Francisco . I met all kinds of people in the solutions profession world . There was like events , there's meetups .

I'd show up , and when I moved to Chicago they didn't exist . So I started a group here in Chicago and then I was talking to a fellow who ended up being my co-founder , who was in Seattle , and we were like , hey , if you aren't in Chicago , san Francisco , new York , seattle , how do you connect to people ? And the answer was he didn't .

So we were like , hey , we're going to start this company and guess what the pandemic're like ? I bring this up because that's like talk about risk my business . Actually , we moved it up because of the pandemic and we filled a void . I'm not afraid to admit what we had . We had amazing execution .

We were the only player in the market and we had a little bit of lightning in a bottle . It was what it was . But as that business went on , I was running my own business and I was also working at a larger enterprise company . What's really interesting , alex , is that I had a bit of both of these things In my own business .

I was , I would say , almost psychotic on a level of control and it is what I felt like we had to do .

Being this first company to market , first platform , trying to make noise that the pandemic just starting , I remember being like , oh , we're going to be inside for a couple of weeks , you know , like who knew what we were in for , right , but also like empowering my team at this larger enterprise company and getting a bet of both worlds .

And as we talk about risk , right , I left that company after 15 months to start my own business and to go full time on my own business . I should say , excuse me , and I'm very fortunate and a little bit of a beneficiary of the market where it was , where I went full time and sold in the same year Amazing experience .

But when I decided to leave my nice steady job and I just got promoted , I got a nice raise . It's also the pandemic I looked at and assessed the risk of the situation where I said , hey , I've already been kind of doing this for eight or nine months and this company is my own company is continuing to take off . What's the worst case scenario ?

And the worst case scenario is that I potentially got a better job than the one that I just had because I opened my network , people knew me , I built relationships and I went to another company and got a raise uh , raise more , more responsibility . And the best case scenario is I changed the trajectory of my career , I changed my life and I build this thing .

That has never been done before and I got very fortunate that it became best case scenario . Right , but when you assess , risk is like one . A bet on yourself is the best bet you can make . You control your own destiny . Every detail matters , everything matters . But I think that again , I'm very risk-conscious . What is the worst thing that can happen ?

What is the worst case scenario ? Look , I have a family , I've got a daughter who lives long distance . I need to be a part of her life , I need to support her . I got married that same year . All of that pressure makes you like I had to succeed . I had like , and what was success ? And the success was evolving .

Right , there was like a you know , let's call it the floor of success and the ceiling of success . Right , I got fortunate to get closer to the ceiling , but that was something that was part of my assessment and I still look back today where a friend of mine was like I can't believe you left this stable job to start a Slack channel .

Right , like it started there , right , but there was a vision to what we were able to accomplish over a short couple of years . And so , yeah , I think that's like the control and control and the and the risk . It was a very wild time . I mean pandemic was wild time for everybody , you know , stuck , stuck indoors , and everything that was happening was scary .

But I poured all of my energy into my work .

You're defining floor to ceiling right and having a very clear picture of what both of those look like , and then defining . To me , a part of the success was a very specific frame of time that you were going to give this and blocking scheduling productivity . You can control your time totally , how you spend it .

You can control your time totally how you spend it . And so those are a few things to me as you talk about . How do you merge this desire for control with risk and risk tolerance ? It goes to controlling what it is you're expecting out of , however much time you're willing to give .

Uh , managing expectations , Um , I don't believe entirely in like having expectations , but managing expectations and being realistic , um , with everything that you do .

How do I determine ? When do I determine ? And so I think that was full of insights . I want to pivot here for a second , because you've kind of touched on a few to me almost competing themes or stylistic behaviors . You mentioned earlier you're a competitive person , and you've also talked in a lot of ways about the importance of collaboration .

Are those two things compatible ? Can you be competitive and collaborative ? If so , how ?

There's competition between other companies right , so you can , collaboration exists within all of those as well . But I think that is like probably the purest form of like how you look at competition , how you look at collaboration .

Like competition with yourself , like always pushing yourself to be better every single day , to do a good job , to grow , and look at yourself year over year and be like am I a better professional , a better person than I was a year before ? Sure , there is competition , especially like in sales environments of like you know , my performance versus your performance .

But I am a firm believer that competition brings out the best in people . I'm also a believer that competition brings out the worst in people too , but also a believer that competition brings out the worst of people too . But if harnessed effectively , it can bring out the best of people .

And I would actually tell you from my own business I used to tell people all the time I want competition . I want competition because one it's going to force us to be even better . And two , if we're out executing , it's only going to make us look even better , even better . And two , if we're out executing , it's only going to make us look even better .

But I do think there's collaboration because , you know , going to appear to you know , hey , this is how I'm . I'm a situation I'm encountering . How should I solve this ?

Right , if you look at like competition , let's call it salespeople you're still part of the same sales team and you're still part of the same company , and so there can always be a common enemy , right , and it can be that other company . So I believe that they are intertwined .

It's easy to do them poorly and hard to do them well , but I think it depends on the culture of the organization . But you can always be competitive with yourself and collaborative with your peers . That can exist anywhere and everywhere .

What it requires to me something you've talked on throughout is that culture of feedback , of open communication , especially as it relates to competition with yourself . You mentioned the importance of giving feedback , especially candid or developmental feedback .

But as you compete with yourself year after year , how do you bring in the input of others , get their feedback , not just what you think you're doing ?

Engineering you know you're on customer calls and everyone who has ever worked for me know that I asked the same three questions after every single call what went well , what went poorly ? If you could do the meeting again , what would you do differently ? Right , and a version of those with different words .

I also believe in , like I said , leaning in , like Gallup strengths , these types of assessments that can help give you some awareness . Also get awareness from your peers and I in my career have always done lots of 360 feedbacks and really just making the default be what could I have done better ? What could I have done better ?

And I even ask my own employees , right , what could I be doing better to support you ? And people are like , especially when they first start looking at me , like what ? Like what do you need from me to do your job even better ? Right , and like just having that conversation and letting people realize like , oh , wow , this is , this is interesting .

And , um , I'm even at my , my current business , like even with the CEO . We get on a call with the whole team and like air our grievances with each other hey , you were rude this week , you didn't support me on this , and we're just open about it .

And people come into the business like what is going on here , but like you have to lead from the front and so again , it's just , it's being open , being vulnerable as well , right , and operating with transparency . And just again , feedback as a framework I think can go really really well .

And when you're willing to be vulnerable and ask people how I can be better , that goes a long way .

What people expect from from their leaders you know you're talking , leading from the front , Kuz is imposter , the leadership challenge , modeling the way . You know a different way of saying that and , and especially around , vulnerability .

So for for senior leaders out there , executives who maybe didn't grow up in a in a workplace culture where vulnerability was allowed , prioritized you know , you know what what guidance would you give to them how to approach vulnerability in a way that they're modeling the way they're leading from the front on it , but it's not natural or maybe even comfortable for

them yeah , the world is revolving around you so you need to evolve with it , right ?

Right , I think that you have if you look at like like you said , you nailed it on like the demands of the workforce today , it's understanding how to connect with a younger generation or who are folks with different expectations , and it doesn't mean that you go and tell some stupid story that you think is going to build relationships with people and just makes you

look like an idiot . Right ? It's not that ? I've been part of organizations where an executive like trying to do that and did it so poorly that it actually like put them even in a bigger ivory tower . So you want to balance that . But you just also want to let people know that , like you are a human .

The further you go up the food chain in an organization , the more people hang on every word that you say . Think about CEO , cfo , these big fortune , fortune 25 , 50 companies . If you go listen to an investor call , they're hanging and analyzing every single word that that person says Talking to their organization . Every single word matters .

That might not if you're in an organization of 70,000 people . It's very different at the top to the bottom . But figuring out how you can be relatable are simple things like I'm sick , my family's sick . I'm going through a hard time personally . We've got some things going on in my family that is causing me to be distracted .

We've got some things going on in my family that is causing me to be distracted . I encountered this . You know . It's like very simple , human , day-to-day things actually go a really long way in vulnerability and letting people be like oh , that person is a human right , especially when you're these organizations with tens of thousands of people .

You put these executives on a pedestal , right ? The reality is is like they're doing the same things that you do on a daily basis , right , and so just kind of like humanizing yourself is the start .

And then I think there's times where , like especially during COVID , I saw , you know , a lot of people do this well where they were like , look , this is hard , I don't , I'm stuck in my house , I don't , I'm afraid to go outside , my family members in the hospital , like this is tough .

And then you start to be like , oh , that person is going through it too and also like makes an impact on you're like , oh well , if that person's going through it , maybe it's okay that I'm going through it too . Again , you can't overdo it and you need to make sure it's relatable .

It's never good when it's not relatable at all , but I think that's how I look at it and it evolves over time . I tell you the vulnerability that my CEO has with the team . It's unbelievable , right , and it's built like so much trust between all of us where he's like I really messed up this week .

And it's like I really messed up this week and it's like , wow , thanks for admitting that , because now I know .

The other side of that , too , is frustratingly post pandemic , a lot of people have reverted back to the old way and now people know what that vulnerable leader looks like and they really miss it when it's not there .

Um , but , james , we've we've covered a lot of ground today uh , letting go of control , micromanaging , delegating , empowering , uh , feedback and clear expectations , risk , um , empathy .

But I want to turn it to you for , for a closing thought if , if , uh , what are the most important things you think , um , you want the listeners to take away from our conversation ?

And for senior leaders , like the story I started today with , if that leader would have given me more of a blueprint and told me how and given me specific examples instead of just like look at this person , I think I would have been able to action on them much better than I actually did and learned a lot faster .

And so you know , all that to say is everyone's going to have their own leadership style . Everyone's going to do things very differently . There's no wrong or right reason , but you know , not to give a sports example right , but I will , because there's one that always resonates with me .

We talk about raising the floor , and setting the floor and raising the ceiling is . If I look at some athletes in professional sports , there's always been a few people who really set the tone for performance in their organization and they overachieve .

And there , you know , I think of like basketball team examples where a leader like Jimmy Butler on the Miami Heat some of their teams have been so undermatched when it comes to talent , but they have a level of grit and leadership

that it just shines through on performance . And so it just shows that , as a leader , if you make tweaks and dials to the dials and make some changes on how you do things and the expectations that you set , you're able to typically achieve more than you would if you just took a little bit too much of a backseat .

So that's my biggest takeaway , or those are my takeaways to share today , and thanks again for having me , alex . This has been wonderful of a conversation . It's been a learning conversation for me as well , as I think about control and risk , and I hope that some people can listen to this and learn something and action on it . That would be great .