[00:00:00] Michael Pacheco: hello, everyone. Welcome again to another episode of the Remarkable Coach podcast. As ever, I’m your host, Michael Pacheco. And today, joining me, I have Chris Iskander. Chris is a seasoned technology professional with over 13 years of experience at a rapid growth tech startup, which grew into a world leading organization and provided a successful exit for himself and the other shareholders.
Chris is also a skilled executive and team coach whose clients have included leaders and high potentials at fortune 500 companies founders and C suite execs in the startup space as well. Chris, welcome to the Remarkable Coach.
[00:00:39] Chris Iskander: Thanks for having me.
[00:00:40] Michael Pacheco: Yeah. Thanks for joining me, man. I appreciate you making the time.
As always to kick off this podcast, I’d like to invite my guest to just tell us a little bit more about yourself in your own words and why it
[00:00:51] Chris Iskander: is you do what you do. Sure. Let’s see. I am 47 years old live in Toronto, Canada, born and raised in the area, studied mechanical engineering and undergrad did a master’s degree in.
Robotics and control systems and then spent most of my career at a tech startup founded by some friends of mine from university. When we started out, we were. Maybe a dozen of us or so. We were in our late 20s. Didn’t really know what we were doing, but we were too stubborn to fail. And so it was more or less complete chaos, but through brute force and some ingenuity and some luck, we made a go of it.
Company grew organically over the first few years, up to about 65 employees. And then we acquired a couple of competitors and tripled in size overnight and had to figure out how to. Make sense out of all that. And then when we sold the company in mid 2018, we were just north of 300 employees.
So that was a nice exit for myself and the other shareholders and give me a chance to. Figure out what I wanted to be when I grew up and how I came into the whole world of coaching. That kind of goes back to I’d say my early 20s and prior to that point in life I’ve been very much a cerebral, analytical, conceptual kind of engineer type thinker and looking back on myself then I can see that I was living more or less entirely in my head.
But if you had told me that at the time, I would have looked at you funny. I wouldn’t have known what you were talking about. I would have been like, of course I’m in my head. Where else would I be? What are you even talking about? So I was very kind of one dimensional in terms of my access to the human experience was all thoughts and concepts.
And I didn’t really have. I didn’t know what I was missing either. I didn’t have the experience of just ever really being present in the moment or really connecting with people deeply, or even understanding or noticing the nuances of interpersonal dynamics, or even what was going on within myself.
I would say my self awareness at that time was quite low. And on top of that, I would have been very, would have been, I was quite arrogant and condescending towards anything that would have, uh, that I would have at the time written off as like soft skills or fluffy, fuzzy stuff. That’s artsy fartsy nonsense.
I’m an engineer. Give me the hard science. So that was my world back then. And on the advice of a friend of mine, I took this weekend long, professional, no, personal development, workshop. And it really opened my eyes and shined a bright light on my blind spots and handed my ass to me in a certain way.
And I really got to see what I’d been missing and how arrogant I had been and how A lot of the things that kind of capital T truth were really just beliefs, assumptions, judgments, all just stuff I’d accumulated along the way and never really questioned. And I got, I had the felt experience of noticing that and becoming aware of it and seeing how the power of actually reframing and choosing consciously how I choose to see myself, others in the world.
And it was it was a powerful experience. It changed me and it changed. hoW I like my relationships, my sense of myself, what was possible for me, and it because of how much I was impacted by that experience, I really, from that moment, I dreamed of one day being able to make a career out of helping others have the same sorts of insights and realizations.
And so I, that, that planted the seed 20 something years ago, 25 years ago, probably now there was never a straight line between tech startup and anything like that. And we were working insane hours and there just wasn’t much time to really. Do anything about it. So I, that hit the back burner for a long time, but then when the company sold, suddenly I had some time on my hands, I had some financial flexibility and it was a perfect opportunity.
So I, I went all in on, on this, did a bunch of formal coach training. And it’s been my primary obsession ever since.
[00:04:49] Michael Pacheco: I love it, man. That’s a great, what an origin story. I think, in, in my experience, I’ve talked to probably hundreds of coaches over the years. And. One of the qualities that I think makes a great coach is having.
A diverse breadth of experience, and it sounds like you’ve been because you’ve been on, on one side and then you’re, you went through this eye opening experience and yeah, tell me about
What was it specifically that you went through that kind of made you see that there was more to life than, left brain, engineering, mathematics logic, right? What, what opened your mind and your heart to to this, the idea of soft skills, let’s put it that way. I’m trying to think of ways to, to phrase, to frame and phrase this. And it’s a bit difficult, but I think you know what I’m getting at.
[00:05:46] Chris Iskander: I do. And it’s going back a long way. So I’m trying to remember if there was a specific experience or moment that really. Did it for me, but if
[00:05:56] Michael Pacheco: I frame it this way, do you work with people who remind you of yourself back then? And if you do,
[00:06:01] Chris Iskander: how do you help them? Yeah. All the time, I think because of my background as an engineer and, in the tech world, a lot of my clients are also in the tech space and I focus on that realm because there’s a lot of shared experience and shared.
Ways of thinking engineers are trained to think a particular way and as a field of study It tends to attract people who are already predisposed to think in that way. So there’s the type of thinker Aspect of things and then there’s also just the lived experience like we can speak the same language you know if someone is a product manager or a product owner or a Engineering manager like I’ve been in several of those roles and worked with all of the other ones and so we don’t have to waste any time Laying groundwork.
They can talk about how, uh, they’re struggling with their scrum master and they’re on a two week sprint and they’re implementing agile. And I know what all these things mean. And so we speak the same language, which helps fast forward. The, we just drop in and can get right to work.
It’s one of the benefits there. In terms of working with people to broaden their own awareness there’s really no, no one size fits all to that. For me, the access was, it started off philosophical and abstract, um, and then went from there through a chain of reasoning to get to, oh, here’s why you, here’s why you’ve been wrong about the things you’re so certain of, uh, and it was I was led there philosophically, so what was so powerful about that was, And this particular course I took met me where I was at.
It started off in my head and then led me from there to someplace else, um, by deconstructing a lot of the rigid notions and beliefs that I had and getting to, Oh, if I let that go, then what’s left and what’s left is not a thought. It’s an experience of something much more spacious Oh wow, I can actually shut this down for a minute and fully experience what’s going on with me or between me and the person I’m interacting with.
[00:07:57] Michael Pacheco: Nice. In terms of your clients, are you working primarily only in the tech space? I know in your bio mentioned you’ve worked with leaders and high potentials at fortune 500 companies, founders, and C suite execs in the startup space, is this all primarily within tech or are you, do you do more?
[00:08:16] Chris Iskander: It’s not exclusively tech I’ve worked with clients in. I was going to say the banking sector, but banking is mostly tech anyway, yeah, exactly there. A lot of them are in some flavor of tech, whether it’s, sales in the technology space or whether they’re engineering managers or product managers or VPs or more senior.
So there’s just a, I think a natural fit. I’m not opposed to working with people beyond like in, in other. Domains, but where I seem to have found my niche is primarily in the tech space. And yeah, it runs the gamut from the larger companies. Like we work with people more in the middle management range, anything from manager up to director or VP, let’s say, and then if it’s a smaller company, small to mid sized startup, then I like to work with the leadership team, founders, and There’s something that’s uniquely special about that particular niche, because if I can work directly with the senior leadership team, it really magnifies the impact, like as impactful as it is to coach one leader in an organization, if I can get a whole team together and give them a common language, a common vocabulary.
Set of frameworks exercises to do together, then you can really create a super high performance team, which is deeply rewarding and can make a huge difference to the health and success of an organization. I love it, man.
[00:09:39] Michael Pacheco: At Boxer we, we say our kind of internal slogan is that we help the helpers and it sounds like you’ve got a similar kind of mindset.
So one of the. Phrases that we like to joke about on this podcast specifically is that every executive coach’s dirty little secret is that they’re a life coach because you’re, cause you’re dealing with people, right? Yeah. Do you find that true? Are what kind of things coach is such a.
A broad term, it can mean, two dozen, three dozen different things. Are you working, when you’re working with leaders, are you working more on personal stuff? Are you looking at like ops? What kind of, tactically speaking, what kind of coaching are you
[00:10:17] Chris Iskander: doing? Yeah, that’s a great question.
So the content that comes up there’s some variability, like sometimes it’s pretty tactical. There’s a particular situation that someone wants to think through and they’re not sure how to handle it. But invariably the tactical stuff is linked to something that I would call developmental, where there’s like a new capacity or a new skill set or a new way of being that the person ultimately wants to cultivate, or they’ve reached a point where they’re realizing that what got me here won’t get me there, like all of their habits, all of their, the things that have driven them to a certain point are no longer sufficient to get them to the next level of leadership.
One really common way that shows up is, people that are super highly accomplished, successful, and they rock it all the way up the hierarchy to say director or VP. And a lot of high achievers are get there by being driven by this really harsh inner critic, right? If they fail, they just beat themselves up mercilessly.
And that’s the by cracking the whip on themselves. It has always kept them moving forward and has helped them achieve success. But internally, they’re brutal to themselves. And then when they reach that senior level where they’re. About to enter the C suite or the executive level, they’re told, Oh, you’ve got to work on your confidence and your executive presence, which is exactly the opposite of this inner critic, right?
It’s like quieting that down. And so the struggle is, how do I put down this sidekick I’ve had? That’s been my has helped me get here. And now I have to end that internal relationship and somehow transcend that and get into this mindful role. State of inner calm where I’m grounded in knowing that I’m okay.
And that, that can be a, it’s a super common thing that happens all the time. Imposter syndrome, people sometimes call it. So that’s a pretty common one. And then perhaps more broadly than that, I think if there’s a through line that kind of unites most of the work I do, I’d say it comes down to two things.
One is clarity of thought, which is untangling. Assumptions, beliefs, conflicting motives that are not really explicitly clarified yet. So getting all that out in the open and untangling it. Yeah. And then the other piece, which is just as big, maybe bigger. Is clear, effective communication.
So much of what we do comes down to communicating especially in leadership, it’s more or less all you do there’s some decision making, but even that’s collaborative for the most part. And and there’s generally speaking quite a large chasm between what people think they’re conveying and what they’re actually conveying, what, like in the intention of the sender.
And what the receiver actually takes away are often very different. And there’s a lot of really good work that can be done helping people tighten that up and just get better at communicating. So that’s my, one of my favorite places to play. And it shows up quite a bit.
[00:13:06] Michael Pacheco: I like it. Yeah. Yeah. I couldn’t agree more.
I think in, whenever you’re working with teams, um, and leadership, anything in that realm or in that zone, the interpersonal Is it drives everything like it’s the lead domino, that, whether it’s, communications or and I think self awareness is a big part of that as well, understanding yourself and understanding how you communicate will help you better understand or have empathy to how you are then perceived by others.
[00:13:40] Chris Iskander: For sure. Yeah, absolutely. And within communication, there’s, are you speaking clearly? Are you setting clear expectations? Are you holding people accountable?
Are You know, or are you beating around the bush and watering down the message and trying to hint at something indirectly without saying it, which a lot of people do under the guise of being nice, but it’s not nice to make someone guess what you really want. It’s actually frustrating.
Helping people communicate directly, but in a way that’s effective. And so that, that sort of requires separating the content of the message from the vibe or the energy or the charge around it. Okay. And so that’s where inner world meets outer world. Managing your own stuff and your own emotions, having mastery over your own emotional state so that when you communicate, when, if you can master your inner state, you can say anything to anybody and they’ll be able to hear it.
That’s my conviction. And where we struggle is when what we’re trying to say gets contaminated with how we’re saying it, which is really a reflection of some unresolved emotional stuff that we’ve got going on and it shows up as a judgment or as snark or cynicism or, something like that.
Sarcasm. Yeah, I, I know.
[00:14:51] Michael Pacheco: When I get into those situations I’ll take a beat and I’ll make sure that I’m not breathing shallow. I’ll check my pulse and see if my heart is racing and then maybe, yeah just take a beat, pump the brakes a little bit and, find a way to come back to it.
Or to just approach it in general
[00:15:10] Chris Iskander: from a more grounded
[00:15:13] Michael Pacheco: place.
[00:15:14] Chris Iskander: Totally. Yeah. Yeah. Yeah. And there’s the stuff you do in the moment when you notice you’re starting to ratchet up. Huh. Like you said, take a few deep breaths, step back. There’s some physiological, like you’re engaging your parasympathetic nervous system and cooling your engines a bit.
Then there’s some bigger picture. Stuff like just keeping in mind like recognizing that for what it is. It’s a threat response when we get amped up It’s part of our brain responsible for keeping us alive doesn’t know the difference between a bear coming at us from the woods and somebody Criticizing our PowerPoint presentation Obviously, these are not the same things
[00:15:53] Michael Pacheco: vastly different things
[00:15:54] Chris Iskander: exactly, and so having that awareness top of mind, which is like Fundamentally, in almost every situation, you’re probably perfectly safe, your physical needs are met, your survival is not threatened, and whatever the worst case scenario possibly is of this thing that’s freaking you out in the moment.
The end of it, you’re going to go home to your perfectly climate controlled home that has food in the fridge and, you’ve got Netflix and Disney plus and crave, and you can go on Amazon and click on something and have anything you can imagine wanting tomorrow. Like it’s, things are fine.
[00:16:33] Michael Pacheco: Things are fine. And you’ll get there. Vis a vis your perfectly climate controlled automobile.
[00:16:40] Chris Iskander: Yeah, exactly. Exactly. With the seat warmers if it’s winter, and it’s just our actual lifestyles have improved so much and evolution is painfully slow. But we can hack that by being aware of it and just really keeping that top of mind, realizing you’re not threatened.
And it’s, and whatever, even if someone’s coming at you with harsh criticism, More often than not, it’s not about you. If they’re losing their emotional control that’s them losing their stuff, right? That’s about them more than it is you. And just letting other people’s stuff be theirs and taking full ownership of yours can be tremendously liberating.
And then there’s other practices too. Like I’m a huge fan of meditation on the regular, which is a great way to establish a stable, calm baseline. Regular exercise, yeah, lots of great stuff people can do to really get to a place of mastery over their inner state, which I think is really the keys to the kingdom.
Yeah,
[00:17:39] Michael Pacheco: even like man, it’s just simple stuff like being able to mentally delineate between who you are and what you do. So if someone is, like you said, if you’re giving a presentation and someone’s criticizing your PowerPoint presentation, that is not an attack on you or your person. It’s a criticism.
It’s an attack right on your presentation on something that you did. And it’s, it doesn’t, it’s not, don’t let that affect, it’s not they’re not attacking you and who you are.
[00:18:10] Chris Iskander: Totally. Yeah, there’s like we tend to Conflate our identity with yeah There you go what we do or what or a thing we did or the way someone reacts to a piece of work We put out or whatever and then the two are not the same Yeah, absolutely.
[00:18:24] Michael Pacheco: What Chris what is a typical engagement with you look like?
[00:18:28] Chris Iskander: Typical engagement would be Six month engagement is fairly common. It really depends on the scope and the goals. We start with that. What does the client want to achieve? And people usually have a vague, some of a sense of what they want to work on.
But, we start by, by really getting that crystal clear and defining what would a successful end state look like? If we fast forward six months, how will we know that we’ve succeeded and that our time together was valuable? And I look at that from at least a couple of different angles, like what are the measurable things?
Maybe somebody wants a promotion or a raise, or they want to take their business to, x level of revenue or profit. So those things are measurable. And some of them are quantifiable. Others might just be behavioral, like I will have a new habit that’s fully ingrained, or people will be giving me feedback that they’ve noticed a change in this way or that way.
And then there’s the interstate, like how will you feel differently? And how will you think differently? And, so we look at it from the objective and subjective points of view. And so they’ve got a really clear picture of the destination that we’re aiming for. And then I do a couple of other things at the outset.
We get a clear picture of where we’re headed. And then we also need a picture of where we’re starting so that we can carve out a map between points A and B. So the destination point B, the next question is, okay, what’s point A, what’s the current reality? And a person will have their own sense of what that is, they can lay it out, here’s where I think I am, here’s where I think my challenges and struggles are based on their own self awareness and self concept.
But I like to supplement that with sources of data from two other places. One is a standard personality profile. That gives some objective data that we can map onto a person’s sense of themself. Which one do you use? I’m a bit of a contrarian when it comes to assessments. There’s a million popular ones out there.
DISC and Myers Briggs and all of those. And the truth about many of those is that they’re pseudoscience. And being an engineer, I just can’t, I can’t stomach it. So I default to what’s actually scientifically validated. And by far and away the most scientifically validated model of personality is called the Big Five model of personality traits.
So it, it, rather than putting people into types like, ENFP or INTJ it rates you on a percentile basis on five different axes, openness to new experience, conscientiousness, extroversion. Agreeableness and eroticism. I use a test called the IPIP 300, which is a 300 question survey based on that.
And it gives you, a percentile rating on each of those five dimensions. And then within each of those five, there are sub dimensions, which get more granular and nuanced. So that’s my approach with assessments. And then my favorite tool by far is a 360 feedback. So I’ll have the client identify usually between say six and 10 people in their orbit who are in a good position to provide feedback about them.
And then I will conduct those verbally. So we’ll do 20 minute zoom calls typically where I ask them, what would you say this person’s top strengths are top weaknesses or blind spots and what other advice might you have? And. That’s where I get really great, feedback from a variety of other perspectives and then.
With all of that in hand, we’ve got the person’s sense of themselves. We’ve got this personality assessment and we’ve got feedback from others. Now we’ve got a clear picture of point A. We’ve got a clear picture of point B. And then we dive in and go to work. And so typically we’ll meet either weekly or biweekly for about an hour through the span of the engagement.
And then we check in periodically every four to six weeks or so we check in and say, okay, are we on track? How are we doing against your goals? Are those still the goals? Has anything changed? What corrections do we need to make along the way? And Kind of rinse, repeat until, uh, until they reach their goals.
And, it happens somewhat frequently that we’ll start off on a six month engagement and, by the end of month three or four, they’ve gotten everything they wanted and we ended up having an early completion conversation and kind of virtual high five and off we go. Awesome.
[00:22:35] Michael Pacheco: Awesome. That sounds so that’s the, it sounds like one on one coaching.
Is it a similar process for team coaching when you work with
[00:22:42] Chris Iskander: teams? Team coaching is quite different, actually. So yeah, you’re right to point out the distinction. One on one coaching is highly personalized and is, very much a, this active inquiry exploration where it’s the thought partnership kind of thing.
We explore together and see what unfolds in the conversation and insights emerge. Team coaching is a combination of some of that, but there’s also More of a training and educational component to it. So you get a team together and talk to them about creating a team charter, for example, where you ask some very concrete questions like what’s this team’s mandate?
What is the shared objective or objectives that this team needs to produce? None of the individuals could do on their own. What is it you need each other for? Gotcha. And. Who are the stakeholders? What would they say your objective is? It’s, you kind of work backwards from the stakeholder perspective, get clear on what the mandate is.
What are the roles? Who’s in what role? What are the boundaries between your different roles? Is everybody aligned about that? What are your team values? What do you really stand for and not in a schmaltzy kind of motivational poster kind of way but what do you actually value and how I measure that is like your values as Indicated by your behavior, right?
Like what are you actually doing? Because that’ll tell you what you value. That’s
[00:24:03] Michael Pacheco: yeah I mean that’s that was gonna be a follow up question is how do you I mean, how, sometimes when you ask someone a direct question, you’re going to get fed a line of BS, or maybe it’s not intentional BS, right? Maybe they just don’t, maybe they don’t have the self awareness to really know.
[00:24:20] Chris Iskander: How do you give you something aspirational, right? This is what I think sounds good or what I think we should value. Yeah. And then, so that always, I always come at that with some skepticism and kind of cross check it against, how do you, what do you reward? What do you incentivize? What do you disincentivize?
That’ll tell you what you’re actually valuing. Somebody might say we value work life balance. Okay, you’re ordering pizza for the team at 9 p. m. On a Friday, you can’t tell me you value work life balance and you don’t have to value that. You can value competitiveness and hard work and grinding it out.
That’s perfectly, in my startup experience, we categorically did not value work life balance. It was anything, but so I’m not here to judge what your values are, but I’m here to hold up a mirror and help you get clear on what they are so that you can tell the truth about it and just. Either get honest about it and own it.
Yeah, or if you discover something in that process that really doesn’t work for you Then what do you need to change in terms of your behavior? What example you set as a leader? What you reward what you? Disincentivize, what do you tolerate that? You shouldn’t be tolerating all of those sorts of things and When the leadership team can get crystal clear on those things your mandate, your mission, your stakeholders, your values.
anD then one other thing, which is a set of what I call working agreements. And by working agreements, this is all the stuff that we assume and take for granted about how things should be done or how we should interact with each other, but we don’t often talk about. And this is where a lot of friction comes up.
A lot of if my assumptions about what’s super obvious and yours are different, then we’ll be butting heads about things that we each take for granted, but we never talked about. So the thing to do is to identify those and to talk about them. a Classic one would be accountability. How should we hold each other accountable?
We’re going to be over the course of our work together, we’re going to be making. Requests and agreements, promises, and sometimes we’re not going to keep those promises. So then what? How should I call you out if you’re late on something you promised to deliver to me? And how can I expect you to respond when I do that, right?
And if you get clear on that stuff up front, then it takes away any awkwardness, any friction, and it preemptively disarming a lot of the sources of conflict. And so that can be super valuable. So where did we? How did we get here? You’re asking about the differences between team coaching and one on one coaching with team coaching is much more of a structure to it and much more of an educational component and then a co creating the answers to all of these questions that I’ve just been pointing to and then documenting it and saying, okay, here’s who we are as a team.
Here’s how we want to work together. Here’s whose job is what and all of those things. And when you get a team that’s aligned on all of those elements. Variables, it’s something else firing on all cylinders and and look out, they can, there’s a markable difference between the team like that and your average team, which is chugs along at some state of mediocrity or low level dysfunction.
[00:27:30] Michael Pacheco: That’s great, man. I think
Circling back to you, you said, I’m not here to. Judge your values, like what you guys value, right? Pizza at nine o’clock at night on a Friday. Yeah. I think that in, in any business there are, we, we get fed the same, like business owners, leaders, right? We get fed kind of the same stuff over and over again.
So work life balance is supposed to be valued. Like you said, like maybe it’s maybe grinding it out, right? Maybe it’s maybe pizza and beers at 9 PM on Friday is team camaraderie. Maybe that’s the values, nothing wrong with that. And I think that it’s, this is one of the reasons.
So I was having this conversation with one of my coaches earlier this morning, and I think it’s very difficult for. Leaders, business owners, founders, whatever it is to see that sometimes because they’re so in the weeds. And that is why it is so important to have a coach because you need one. You need someone who is detached from the situation, right?
You need to have someone around that you can go and say, what’s, what am I missing? What am I missing? Because I’m in the eye of the hurricane. You’re outside. You can see what’s going on. Help me. What am I missing here? And I was having that conversation with my coach this morning about some stuff that’s happening at Boxer.
And I’m just, and I’m like, I feel like I’m missing something here, but I’m just not sure what it is like you, you see the bigger picture, help me out. And it was a really great conversation. I think that’s one of the just one of the huge values of having a coach is being able to come in and do things like that.
And again, like you said, like to not judge, but to be able to
[00:29:17] Chris Iskander: yeah, absolutely. It’s I’ve heard it called the clarity of distance. Huh. There you go. And I like to say it’s really hard to read the label from inside the bottle. And so that one too. Yeah, absolutely. And that’s just how we’re wired.
It’s always easier for us to see other people’s blind spots than it is our own and vice versa. And I think that’s a huge part of it. And then the other thing you mentioned, which I think is critical. Is just reflecting the truth, but without judgment, and I think that’s, those two are, uh, very closely linked.
That’s what a coach is, as distinct from, say a romantic partner, or a business partner, or whatever. They’re, they also have your number, and they can reflect back to you what you’re not seeing, but they’re probably going to do it with a certain edge or voltage to it, because they’ve got skin in the game.
Their own needs are tied up in it. And it just comes with a different energy. And there’s also more at stake in that relationship. If someone close to you is coming at you with that certain negativity, like it’s going to trigger your own defenses because it might threaten certain aspects of your, if it’s a business partnership, it can threaten your work, your career, your finances, with a romantic partner, it can threaten the stability of your home life, like where your mind goes is Oh no, something that I really value is at risk right now.
Yeah, whereas with a coach I don’t have like my only commitment is to my client And I don’t have any personal charge or anger about whatever they’re dealing with Or doing or not doing or seeing or not seeing and my only role is to hold up a mirror For their benefit and it’s done Purely for them and they get that and they know it and so they can hear it from me in ways that they can’t hear it from others.
[00:31:02] Michael Pacheco: Yeah. Yeah, you’re able to, you’re able to deliver the bad news with love, right? Without A hundred percent. Yeah.
[00:31:10] Chris Iskander: Yeah. And they know that I’m only doing it because I care, because that’s what this relationship is. It’s my job to in part, to help you see uncomfortable truths that you might not want to see, but I’m not doing it out of any malice.
I’m doing it because you’re paying me to do it and you want it on some level or you wouldn’t be, we wouldn’t be talking.
[00:31:28] Michael Pacheco: Yeah. I love it, man. Tell us about a big win that you’ve had with a client of
[00:31:33] Chris Iskander: yours as a coach, a recent one that I’m really quite proud of I may have alluded to it a little bit earlier in more general terms, but the client who’s a VP, just super successful like one of these people that just, I was enormously impressed with her list of accomplishments and her success and her confidence.
And she came to me cause she was. Frustrated at her inability to get the attention and the resources and frankly, the respect that she needed from her CEO and C suite in order to really be able to do her job. She was in charge of a small, but, promising area of a much larger business, basically like needed certain things in order to really run with it and grow and felt like she was hamstrung a bit.
And needed some changes to be made, including like she wanted full P and L accountability and wanted her own sales team and her own marketing people and some of her own developers and involved reorganizing some things in the company and it just wasn’t getting done. Long story short, we worked together.
This was one where we signed on for six months and within three, three and a half she got everything she wanted. The big insight for her was, uh, as, as confident as she is in her abilities. When it came to negotiating and really getting what she needed and commanding that respect at the senior levels She also had this desire to please and to be liked and that was getting directly in the way And so she was letting people Rush her off or not.
Take her seriously non confrontational You know very smoothing things over and was just not assertive enough frankly and I find Not to generalize too much, but I think a lot of, there’s a gender dynamic at play here, like women are generally socialized, still, to be much more accommodating than men, and they’re not rewarded for the same traits and behaviors that men are, so this is like a double standard there, and it can be challenging for a lot of professional women to overcome and, she would, I think she would agree with that part of it anyway, so we worked together for a few months long story short, but By the end of it, she got everything on her wishlist from her CEO, reorganized her part of the company, gave her a full PNL, gave her a budget, gave her own marketing sales dev, just was a, it was a grand slam.
She got everything she wanted and it was just super satisfying.
[00:33:56] Michael Pacheco: That’s awesome. That’s awesome. Yeah. And in terms of your. with her, did she hire you personally as her personal coach? Or was she, were you brought in by the company? What is, what did that look like?
[00:34:10] Chris Iskander: Yeah. Good question.
In this case, she brought me on personally, so I worked with her directly. Cool. So some of my clients. We structure it that way. In other cases, they’ve got corporate budget for it. So the company pays, but I work with the client. This may be obvious to your listeners, but I’ll say it anyway.
Regardless of who’s paying, my allegiance is to the client that I’m working with. It makes no difference whether the company’s paying or they are, I’m there for them. But yeah, I do it both ways. I’ve seen both. I think they’re probably equally common. More and more companies, I think are really appreciating the value of coaching and are allocating some resources to it, either as part of a training budget or specifically for coaching.
And I think that’s great.
[00:34:48] Michael Pacheco: Nice. And you work, it sounds like you work on zoom. Are you working globally? Are you working in North America, specifically in Canada?
[00:34:55] Chris Iskander: Mostly in North America. I’d say a majority of my clients are in the U. S. Some are in Canada. Occasionally, occasionally someone in Europe. I worked with one person in India, which was fun.
It’s such a globalized world. It’s one of the, one of the great things about Zoom is you can connect with people from anywhere. But majority are in North America. And I would say. Most of them are in the States. Right
[00:35:17] Michael Pacheco: on. Right on, man. What three books do you recommend all of your clients read?
[00:35:25] Chris Iskander: Great question. I actually have a, like a recommended reading list on my website. And so if I were to pick three, it probably varies somewhat from client to client. But a few of my favorites are Thinking Fast and Slow, which I believe is by Kahneman. Yep. Great book on cognitive biases and all the predictable ways that our brains take shortcuts and get things wrong.
Another one of my favorites is Stumbling on Happiness. Which I read several years ago and it’s related, but it’s In particular about how the primary thesis of the book is that we make decisions in the present based on what we think will make our future selves happy. And then the book goes into great detail, exploring all the wild and wonderful ways we get that catastrophically wrong and how we might go about doing better and making better choices.
So that was a really insightful book and a fun read as well. And then Another one that comes up fairly frequently, especially for anyone who’s involved in any kind of change initiative, is a book called Switch by Chip and Dan Heath. And it’s all about change management, but it’s presented in a very accessible, digestible way, and they break it down into a nice, very clear, clean model where the takeaways are easy to remember, and the insights are actionable.
[00:36:41] Michael Pacheco: Yeah that’s great. I think they also, those guys they’re brothers, I believe. And I think they also did made to
[00:36:46] Chris Iskander: stick. Yeah. They’ve written a number of books and I like their style. Yeah. They’re it’s simple, clear, useful, um, actionable. Exactly. I remember
[00:36:57] Michael Pacheco: stick being actionable. Like you got, you didn’t walk away from that with a whole bunch of theory, right?
You walked away from it with here’s some things that I can actually do.
[00:37:05] Chris Iskander: Yeah. To improve. Yeah. Yeah. And they boil things down into just a handful of little kind of clever one line soundbites that are easy to remember and easy to keep in mind. And with a lot of their books, at least with Switch, there’s like a one page PDF cheat sheet, which once you’ve read the book, you can look at this one page and go, Oh yeah, here’s where I need to do more of this or less of that in order to get things moving.
It’s practical, helpful, easy
[00:37:31] Michael Pacheco: to read. Useful reference sheets. I think Crucial Conversations comes with one of those as well. That’s really
[00:37:37] Chris Iskander: helpful. I haven’t read that one yet, but it’s on my list. You, yeah.
[00:37:40] Michael Pacheco: If you’re doing, if you’re doing stuff with like teams and leadership, that’d be a great one for you.
Yeah, absolutely. Solid. Yeah. Chris, you’ve got a complimentary leadership consultation call for our viewers and listeners. Do you want to talk about that a little
[00:37:53] Chris Iskander: bit? Absolutely. Yeah. So the way I usually. Start working with someone or start exploring whether or not it’s a mutual fit is just you can book a complimentary call.
45 minutes. We’ll get to know each other. We’ll talk a bit about, your goals, your challenges. Make sure any questions you have get answered. And if there’s a strong fit, then we can talk about next steps. And if not my commitment with each of those calls is that you’re left with. It’s something valuable that you can actually put into action in your life regardless.
So it’s a valuable, interesting call and if it’s a strong fit in both directions, we can talk further. Awesome.
[00:38:32] Michael Pacheco: And where can people go to book that call?
[00:38:36] Chris Iskander: A couple of places. You can find me on LinkedIn, and there’s a link right on my LinkedIn profile page to book a call, or on my website, which is executivesoundboard.
com. There’s a link there, I think, under contact to book a consultation, and you can book it right on my website. Perfect.
[00:38:56] Michael Pacheco: Awesome, man. Is there anything else that we didn’t have a chance to touch upon that you’d like to talk about?
[00:39:03] Chris Iskander: We could talk for hours, I’m sure, but, It’s crowded. Yeah, no, nothing comes to mind.
This has been a lot of fun, and I appreciate you having me on. Awesome,
[00:39:10] Michael Pacheco: man. I do. Before we go, I have to I have to ask. There’s a picture of what appears to be Tony Montana behind your right shoulder. What is the significance of that?
[00:39:21] Chris Iskander: What’s the significance? Good question. That picture was actually my brother and sister bought it for me on a trip they took to New York 25 years ago probably.
If you look at my movie collection like my actual DVD collection that tells you how old the collection is I’ve got all the gangster movies you know, all the Godfather Goodfellas, Casino Heat, Scarface, I just Yeah. Something about that genre really spoke to me when I was younger. Yeah. I don’t know what that says about me and prefer not to dig too deeply into it, but It says that you’re a man you came from there.
Because Pacino is the part you have to watch. I right? He’s just the best. He’s
[00:39:58] Michael Pacheco: brilliant. Absolutely brilliant. Heat is an underrated one, man. I’m glad that you brought that up. Heat is great.
[00:40:04] Chris Iskander: Oh yeah the Seen with DeNiro and Pacino in the coffee shop, having that just amazing, frank conversation.
It was just perfection.
[00:40:13] Michael Pacheco: Yeah. So good. Awesome, Chris, man. Thank you so much for making time to chat with me about coaching and everything else. I appreciate it, man. Thank you so much. Thank you for having me. You bet. And thank you as always to our viewers and listeners. You guys are awesome. If you found this valuable, if you know someone who found this valuable, please give it a share let people know and always, do the things like subscribe and all that.
Thank you so much. We’ll see you guys next time. Cheers.
