Latest / Chief in Tech Deep Dive Shortcast / Chief in Tech S1E41 - Rose Cartolari : The Everchanging Journey of Leadership – Staying Ahead of the Game

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Chief in Tech S1E41 - Rose Cartolari : The Everchanging Journey of Leadership – Staying Ahead of the Game · Chief in Tech Deep Dive Shortcast

• 0:00
  Imagine drawing a meticulously detailed map for
• 0:03
  a cross -country road trip. You map out every
• 0:06
  gas station, every scenic overlook, every overnight
• 0:10
  stop. Right. You've got the whole thing perfectly
• 0:12
  planned out. Exactly. Then you step outside,
• 0:14
  you get in your car, and you realize the continents
• 0:16
  have literally physically drifted. Wow. Yeah.
• 0:19
  The rows you parent to take are just, well, they're
• 0:22
  at the bottom of an ocean now. And the mountains
• 0:24
  have completely moved. Just a totally different
• 0:26
  landscape. Yeah. And that is exactly what corporate
• 0:29
  planning and personal strategy feel like today.
• 0:31
  I mean, you make a plan for the year, you allocate
• 0:34
  your resources, and then the terrain simply shifts
• 0:37
  right underneath your feet. It is honestly the
• 0:40
  absolute baseline. of our current reality. I
• 0:43
  mean, the rule book hasn't just been rewritten,
• 0:45
  it's been discarded entirely. Right. We are operating
• 0:48
  in this this VUCA environment. You know, volatility,
• 0:53
  uncertainty, complexity and ambiguity. Right.
• 0:56
  And the crucial thing for you to understand is
• 0:59
  that this disruption isn't just a passing storm
• 1:01
  we can wait out. It's just the weather now. Exactly.
• 1:04
  The disruption is the climate now. OK, let's
• 1:06
  unpack this because How do we even begin to function
• 1:12
  let alone thrive when the ground is constantly
• 1:14
  shaking? Yeah, it's overwhelming. It is, because
• 1:17
  the instinct for most people, and I definitely
• 1:19
  include myself in this, is to just hunker down,
• 1:21
  try to minimize the damage, and hope things eventually
• 1:24
  stabilize. Which they won't. Right. So today,
• 1:27
  we're doing a deep dive into some incredible
• 1:29
  insights from a session by executive coach Rose
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  Cartellari. It's called Navigating the Turbulence,
• 1:36
  Strategic Leadership in a VUCA World. And she
• 1:39
  is definitely the right person to guide us through
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  this. Oh, for sure. She brings, what, over 30
• 1:44
  years of C -suite and advisory experience to
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  the table? Yeah, 30 years. And what makes her
• 1:48
  approach so compelling is that she grounds her
• 1:51
  strategies in actual behavioral science. Not
• 1:54
  just corporate buzzwords. Exactly, no buzzwords.
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  We are looking at concrete mechanisms for staying
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  on offense when the whole world is essentially
• 2:01
  forcing you into a defensive posture. But before
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  we even get into the tactics, she says we need
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  a complete perspective shift regarding the turbulence
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  itself, right? Oh, 100%. As long as you view
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  market volatility or technological disruption,
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  or just organizational chaos solely as a threat,
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  you will remain completely stuck. You have to
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  fundamentally change your relationship with the
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  friction. Yes. There's this striking quote in
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  the source material from Machon Adelayo. Oh,
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  I love this part. Yeah, it says, turbulence breaks
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  a tree's branches, but only tickles an eagle's
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  wings. It's such a great visual metaphor, but,
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  you know, we need to ground that in reality.
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  Because when things get chaotic, most of us,
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  we default to acting like the tree. We really
• 2:44
  do. We root ourselves down. We become incredibly
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  rigid. We fiercely defend the status quo. And
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  as a result, we just get battered. I mean, we
• 2:52
  lose branches. And if you look at the actual
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  physics of an eagle in a storm, the metaphor
• 2:58
  becomes even more instructive. Wait, really?
• 3:01
  How so? Well, an eagle doesn't survive a storm
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  by flapping its wings harder to fight the wind.
• 3:06
  That would just exhaust it, and it would crash.
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  Yeah, right. That makes sense. Instead, it locks
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  its wings and uses the aerodynamic friction,
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  the actual updrafts and thermals created by the
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  storm, to push itself higher above the cloud
• 3:18
  line. Wow. Yeah, the turbulence is the exact
• 3:21
  mechanism of its elevation. OK, so bringing that
• 3:23
  back to a business or personal context, how does
• 3:26
  a leader or a team actually do that? Like, how
• 3:29
  do you use market turbulence? to pivot a failing
• 3:33
  product into a new opportunity rather than just,
• 3:36
  you know, taking the hit. What's fascinating
• 3:38
  here is that Cardelari uses behavioral science
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  to explain the human element of this. Okay. When
• 3:44
  we are forced into highly volatile situations,
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  the psychological friction pushes us completely
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  out of our comfort zones. Which feels awful in
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  the moment. It feels terrible. But her approach
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  highlights that these roughest instances are
• 3:57
  the precise tools that force us to make sense
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  of things in new, innovative ways. Because the
• 4:01
  old ways literally don't work anymore. Exactly.
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  When the old processes break, you are forced
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  to build new mental models. You are forced to
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  reconcile competing priorities. And interestingly,
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  she points out that you are forced to forgive.
• 4:14
  Yes. That concept of forgiveness really stood
• 4:17
  out to me, too. Because... Honestly, it's not
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  a word you typically encounter in a corporate
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  leadership seminar. Not at all. It's usually
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  all about accountability. Right. But in a highly
• 4:26
  volatile environment, mistakes are mathematically
• 4:28
  inevitable. If your team is terrified of miscalculating
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  in an unpredictable market, they'll just freeze.
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  They become that rigid tree. Exactly. They hunker
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  down and do nothing. And the psychological weight
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  of constant disruption is immense. I mean, if
• 4:43
  a leader cannot forgive themselves, and their
• 4:46
  team. For the necessary friction that occurs
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  during rapid adaptation, the organizational culture
• 4:51
  turns toxic immediately. It's a recipe for burnout.
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  Completely. Embracing these opposite competing
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  facets of ourselves during rough times like demanding
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  excellence while forgiving inevitable missteps
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  is what actually allows an organization to adapt.
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  It builds resilience. Yeah, it builds the kind
• 5:08
  of deep resilient human connection that you absolutely
• 5:10
  need when the external world is chaotic. You
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  end up sharing the cognitive load of the turbulence.
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  Which shifts the dynamic entirely. If the internal
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  culture is reconciled and connected, the external
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  chaos becomes like a problem to solve collectively
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  rather than a threat that splinters the team
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  apart. Precisely. But, okay, here's the catch.
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  Being an eagle and riding those thermal updrafts
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  is completely useless if you have absolutely
• 5:36
  no idea where you are flying. Right, you're just
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  drifting. Exactly. Which brings us to the first
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  major pillar of navigating this turbulence. Finding
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  your direction. Yeah. The wind might be lifting
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  you, but to what end? The source material is
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  explicit about this first step. You must set
• 5:54
  your North Star. I have to play devil's advocate
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  here, though. Go for it. We just established
• 5:59
  that we live in a world defined by constant change.
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  Business models that worked three years ago are
• 6:03
  totally obsolete today. So doesn't committing
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  to a fixed, unyielding North Star make you dangerously
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  inflexible? I can see why you'd think that. I
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  mean, practically speaking, if my North Star
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  as a department head is providing elite, high
• 6:18
  -touch customer service, how does holding onto
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  that help me when my budget is suddenly slashed
• 6:25
  by 40 %? I need to survive the quarter, not,
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  you know, stare at the sky. See, your pushback
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  highlights the exact reason why most people misunderstand
• 6:34
  the concept of a North Star. Oh, really? Yeah,
• 6:36
  you're conflating the destination with the route.
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  OK, explain that. A North Star is not a step
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  -by -step project plan. It's not a quarterly
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  milestone, and it's certainly not a fixed budget
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  allocation. It is your guiding principle. It's
• 6:49
  the core value proposition that defines why you're
• 6:51
  doing the work in the first place. So it's the
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  why, not the how. Precisely. In a VUCA world,
• 6:57
  the how is going to change constantly. Returning
• 6:59
  to your example, if your budget is slashed by
• 7:01
  40%, your tactics for delivering elite customer
• 7:04
  service must change. Right. I can't afford the
• 7:06
  same things. Exactly. You can no longer afford
• 7:09
  a massive call center offering 24 -7 phone support.
• 7:12
  The old map is gone. But because your North Star
• 7:15
  remains elite service, you pivot your methods.
• 7:18
  So I have to get creative? Yes. Maybe you invest
• 7:21
  heavily in proactive, highly personalized, automated
• 7:24
  check -ins. Or maybe you create an exclusive,
• 7:28
  high -value community forum for your top -tier
• 7:30
  clients. The mecha devolved, but the underlying
• 7:34
  purpose remained steady. Okay, I see. In a landscape
• 7:37
  full of ambiguity, the North Star is literally
• 7:40
  the only thing that isn't ambiguous. Exactly.
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  It prevents you from just reacting to the budget
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  cut by indiscriminately slashing the quality
• 7:47
  of your product across the board. Which would
• 7:49
  ultimately destroy the brand anyway. That is
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  the crucial distinction. Without that fixed point,
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  every single market disruption or unexpected
• 7:56
  crisis just sends an organization spinning. You
• 7:59
  end up putting out fires, engaging in forced
• 8:02
  mutation rather than intentional evolution. So
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  the North Star allows you to be radically flexible
• 8:07
  in your methods while remaining utterly fixed
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  in your ultimate destination. I want you, the
• 8:12
  listener, to really think about your own career
• 8:14
  trajectory or the team you manage right now.
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  When things get incredibly chaotic, like when
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  a major client pulls out or a new competitor
• 8:23
  disrupts your space, do you have a clear North
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  Star guiding your immediate decisions? Or are
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  you just trying to survive until Friday? Because
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  having that anchor is the literal difference
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  between navigating a storm and merely being a
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  victim of it. And once that North Star is established,
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  the very next challenge is managing how you actually
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  move toward it. Yes, the momentum. Because the
• 8:44
  natural human instinct, especially when the world
• 8:46
  feels like it's just spinning out of control,
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  is to rush. The pressure to keep up creates this
• 8:51
  frantic energy. But the source material warns
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  us that our default definition of fast is often
• 8:58
  completely counterproductive in a complex system.
• 9:00
  It absolutely is. Here's where it gets really
• 9:02
  interesting. This brings us to a fascinating
• 9:04
  distinction the source draws between two types
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  of momentum, operational speed and strategic
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  speed. A huge difference between those two. Yeah.
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  When I was reading this section, the best analogy
• 9:15
  I could think of was a treadmill. Operational
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  speed feels exactly like sprinting on a treadmill.
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  You know, you are moving your legs incredibly
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  quickly, your heart rate is maxed out, you are
• 9:26
  sweating, and you feel incredibly busy. But you're
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  going absolutely nowhere. Exactly. You haven't
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  moved an inch. Strategic speed is the realization
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  that you are on a treadmill, having the presence
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  of mind to hit the stop button, getting off and
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  walking at a normal, deliberate pace toward your
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  actual destination. The treadmill captures the
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  trap perfectly because it highlights the illusion
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  of progress. Yes, the illusion. The text explicitly
• 9:52
  defines these terms to strip away that illusion.
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  Operational speed is simply moving quickly. It's
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  measured by the sheer volume of tasks completed,
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  the number of emails you rapidly answered, the
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  back -to -back meetings attended. It is motion
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  for the sake of motion. I mean, we've all been
• 10:07
  caught in that busy trap. I remember a day last
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  month where I spent Eight straight hours, aggressively
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  clearing out my inbox, organizing folders, responding
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  to minor queries. At 5 p .m., I felt incredibly
• 10:18
  productive. But when I actually looked back at
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  the day, I realized I hadn't moved the needle
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  on a single major project. Zero actual value
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  was created. Zero. That is the danger of operational
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  speed. Strategic speed, conversely, is defined
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  by cartillary as reducing the time it takes to
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  deliver value. Delivering value, not just finishing
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  tasks. Notice the profound difference in metric.
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  It's not about doing more things faster. It is
• 10:44
  about getting to the tangible value faster. And
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  in a highly complex environment, the C in VECA,
• 10:51
  prioritizing operational speed over strategic
• 10:53
  speed, is actively dangerous. Because if you
• 10:56
  are sprinting in the wrong direction, you are
• 10:58
  just compounding your errors at a faster rate.
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  You're efficiently executing the wrong strategy.
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  If we connect this to the bigger picture, when
• 11:04
  a system is deeply interconnected and unpredictable,
• 11:07
  blind operational speed just generates more systemic
• 11:10
  chaos. So how do we stop it? Achieving strategic
• 11:13
  speed requires something that feels deeply counterintuitive,
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  almost uncomfortable in a fast -paced corporate
• 11:19
  culture. It requires pausing. Pausing to look
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  up from the treadmill and locate the North Star
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  again. Yes. pausing to analyze the shifting terrain
• 11:29
  and figure out the most direct route to actual
• 11:32
  value. Which might mean doing less. Frequently.
• 11:36
  Sometimes the fastest way to deliver value is
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  to stop doing 80 % of the tasks you're currently
• 11:42
  stressing over and execute flawlessly on the
• 11:45
  20 % that actually matter. Strategic speed is
• 11:48
  about the efficiency of your impact. It requires
• 11:51
  the discipline to say no to busy work. Okay,
• 11:53
  so let's say you step off the treadmill. You
• 11:55
  pause, you cut the busy work, and you are entirely
• 11:58
  focused on finding the shortest path to value.
• 12:00
  Right. The massive hurdle here is knowing what
• 12:03
  value even looks like when the market can change
• 12:05
  overnight. How do you anticipate the shift before
• 12:07
  it renders your current strategy obsolete? Because,
• 12:10
  I mean, you only have one set of eyes, and your
• 12:12
  perspective is inherently limited. This is where
• 12:15
  we move from internal mindset to external architecture.
• 12:18
  To achieve strategic speed, you need to upgrade
• 12:20
  your radar system. You need to see the disruption
• 12:23
  forming on the horizon before it hits your industry.
• 12:25
  The source material argues that you do this by
• 12:28
  diversifying your network of trusted advisors
• 12:30
  to develop the ability to pick up what it calls
• 12:32
  weak signals in the marketplace. Let's break
• 12:35
  that concept down. What exactly constitutes a
• 12:38
  weak signal? A weak signal is an early, quiet,
• 12:42
  often ambiguous indicator of an impending disruption.
• 12:45
  It's the whisper in the market before the shouting
• 12:47
  starts. Give me an example. It could be... a
• 12:50
  strange anomaly in a competitor's hiring patterns,
• 12:54
  or a seemingly obscure piece of tech regulation
• 12:57
  passed in a totally different country, or even
• 12:59
  just a subtle shift in how teenagers are using
• 13:01
  a new app. So it's the pebble falling down the
• 13:03
  mountain before the avalanche hits? Exactly.
• 13:05
  By the time a signal becomes strong, by the time
• 13:08
  it's the cover story of a business magazine,
• 13:10
  or your board of directors is actively panicking
• 13:12
  about it, it is entirely too late to be strategic.
• 13:15
  You're back to playing defense. Right. The entire
• 13:18
  goal of strategic leadership is to catch those
• 13:20
  weak signals early enough to use them to your
• 13:23
  advantage. And this really highlights why the
• 13:25
  composition of your network is so critical. Because
• 13:28
  if you're sitting in a boardroom with five other
• 13:30
  people who share your exact educational background,
• 13:34
  work in your specific industry, live in your
• 13:36
  city, and read the exact same financial news,
• 13:39
  well, you're all going to miss the exact same
• 13:41
  weak signal. You share the exact same blind spot.
• 13:43
  You haven't built a radar system. You've built
• 13:45
  an echo chamber. and an echo chamber only amplifies
• 13:49
  the strong signals you already know about. To
• 13:52
  build a radar system that genuinely works, you
• 13:55
  need profound cognitive diversity. You have to
• 13:58
  surround yourself with people who process the
• 14:00
  world through completely different lenses. And
• 14:02
  the source material provides an incredible real
• 14:05
  -world case study of this concept through the
• 14:07
  biography of the author herself, Rose Kartellari.
• 14:10
  Oh, her background is fascinating. It really
• 14:12
  reads like a masterclass in accumulating diverse
• 14:14
  perspectives. Just looking at her geographical
• 14:17
  footprint alone, she grew up living across India,
• 14:20
  Indonesia, Somalia, the USA, and Italy. That
• 14:23
  is a staggering amount of exposure to wildly
• 14:26
  different geopolitical realities, economic systems,
• 14:30
  and cultural norms. Yeah, but the value isn't
• 14:33
  just in the travel, right? It's in how that exposure
• 14:35
  builds a unique cognitive architecture. Exactly.
• 14:39
  And professionally, her career spans just as
• 14:41
  wide a spectrum. This raises an important question
• 14:44
  about how we build our resumes. She's held management
• 14:47
  roles at American Express, a massive, highly
• 14:50
  structured corporate financial giant, but also
• 14:53
  at UNICEF, a global humanitarian organization
• 14:55
  operating in crisis zones. Talk about two different
• 14:58
  worlds. Right. Plus, she co -founded and served
• 15:01
  as COO of Sharper Pharmaceuticals, and she serves
• 15:04
  on the advisory board of Diversity Magazine,
• 15:06
  focusing on inclusion and equity. When you lay
• 15:09
  out a resume like that, you realize her success
• 15:12
  as an executive coach isn't an accident of networking.
• 15:15
  It's the direct result of cross -pollination.
• 15:17
  That is the exact mechanism of her expertise.
• 15:21
  Think about how cognitive diversity practically
• 15:23
  applies to problem solving. If you spend years
• 15:26
  dealing with humanitarian logistics at UNICEF
• 15:29
  in Somalia, you develop a mental model for resource
• 15:33
  allocation under extreme distress where failure
• 15:36
  literally costs lives. The stakes couldn't be
• 15:39
  higher. Right. And when you then transition to
• 15:41
  a pharmaceutical company in Italy and a sudden
• 15:43
  a supply chain bottleneck occurs, you are not
• 15:46
  looking at it like a standard corporate logistics
• 15:48
  manager. You're looking at it through a crisis
• 15:50
  management lens built in the developing world.
• 15:53
  You see solutions and workarounds that a person
• 15:56
  with an MBA from a traditional business school
• 15:58
  simply cannot perceive because their mental model
• 16:02
  relies on stable infrastructure. Exactly. Because
• 16:05
  she has navigated how entirely different systems
• 16:07
  operate. Finance, global nonprofits, pharmaceuticals,
• 16:10
  publishing. She can synthesize information across
• 16:13
  boundaries. She understands that the solution
• 16:15
  to a bottleneck in European manufacturing might
• 16:18
  actually be found in how a nonprofit in Indonesia
• 16:21
  handle the distribution. Her fluidity across
• 16:24
  these sectors is exactly why she's an expert
• 16:27
  in spotting weak signals. She is scanning multiple
• 16:29
  frequencies simultaneously. So what does this
• 16:32
  all mean for you listening to this right now?
• 16:35
  It means it is time to perform a ruthless audit
• 16:38
  of your own inner circle. 100%. Look at your
• 16:41
  trusted advisors, your mentors, your core team.
• 16:44
  Are they all from the same industry? Do they
• 16:46
  all approach problem solving the exact same way?
• 16:49
  Because if your network is homogenous, you are
• 16:52
  incredibly vulnerable to the next wave of disruption.
• 16:55
  You're missing the weak signals because your
• 16:56
  radar only points in one direction. To navigate
• 16:59
  a complex world, you need a complex network.
• 17:02
  You must intentionally curate people who will
• 17:04
  challenge your baseline assumptions and point
• 17:06
  out the anomalies you are totally blind to. Resilience
• 17:09
  in your outputs requires diversity in your inputs.
• 17:12
  You cannot synthesize new solutions from recycled
• 17:15
  perspectives. We have covered a tremendous amount
• 17:17
  of ground today, moving from high -level mindset
• 17:20
  shifts down to the daily architecture of your
• 17:22
  professional network. There is a very clear,
• 17:26
  proactive roadmap here for dealing with a world
• 17:28
  that often makes us feel entirely helpless. It
• 17:31
  fundamentally shifts the locus of control. You
• 17:34
  cannot dictate the volatility of the market,
• 17:36
  but you have complete agency over how you equip
• 17:38
  yourself to move through it. Let's trace that
• 17:40
  roadmap one more time. It begins with abandoning
• 17:44
  the defense. Stop fighting the wind like a rigid
• 17:46
  tree and adopt the mechanics of the eagle. Ride
• 17:49
  the thermal updraft. Yes. Use the friction of
• 17:52
  the VUCA world as the updraft that forces your
• 17:55
  growth and deepens your team's connection through
• 17:57
  shared adversity and forgiveness. Second, establish
• 18:00
  your North Star. Define the unyielding purpose
• 18:03
  behind your work so you can pivot your tactics
• 18:05
  wildly without ever losing your direction. Third,
• 18:08
  step off the operational treadmill. Have the
• 18:11
  courage to pause, cut the busy work, and prioritize
• 18:13
  strategic speed, finding the absolute shortest
• 18:16
  path to actual value. And finally, tear down
• 18:19
  the echo chamber. Actively recruit trusted advisors
• 18:22
  with wildly different backgrounds, industries,
• 18:25
  and mental models so you can catch the weak signals
• 18:28
  before they become avalanches. It's a brilliant
• 18:30
  framework. It really is. But as we wrap up this
• 18:33
  deep dive, there is one final implication of
• 18:36
  this source material that we really need to sit
• 18:38
  with. something that builds on everything we've
• 18:40
  just discussed, but turns our standard definition
• 18:43
  of success completely upside down. Yeah, if we
• 18:46
  accept the core premise we established at the
• 18:48
  beginning, that the eagle absolutely requires
• 18:51
  the turbulence to rise, and that psychological
• 18:54
  and market friction are the exact mechanisms
• 18:56
  that force us to innovate and evolve, then we
• 19:00
  have to ask a very uncomfortable question. What
• 19:02
  is it? What if the periods of comfort and calm
• 19:05
  are actually the greatest threats to our personal
• 19:08
  and professional development. Wow, that completely
• 19:11
  flips the script on what we're all striving for.
• 19:13
  I mean, we spend our entire careers trying to
• 19:15
  build a moat, trying to establish stability,
• 19:18
  wishing for the market to just be easy for a
• 19:20
  few quarters. But if the wind stops blowing,
• 19:22
  the eagle has to expend twice as much energy
• 19:25
  just to keep from falling out of the sky. Without
• 19:27
  the updraft, there is no elevation. If chaos
• 19:31
  is the engine of growth, then a perfectly predictable
• 19:34
  frictionless environment leads inevitably to
• 19:37
  stagnation. We shouldn't be hoping for the storm
• 19:39
  to pass. We should be studying the aerodynamics
• 19:42
  of the storm. Because the turbulence isn't the
• 19:45
  obstacle keeping you from delivering value. The
• 19:48
  turbulence is the exact fuel you need to create
• 19:50
  it. The storm isn't in your way. The storm is
• 19:54
  the way. That is a paradigm shift that will change
• 19:57
  how you walk into your next crisis meeting. Thank
• 20:00
  you for joining us on this deep dive. We hope
• 20:02
  this conversation equips you to look at the shifting
• 20:04
  terrain in your own life, not as a disaster,
• 20:07
  but as an opportunity to chart an entirely new
• 20:09
  path. Keep questioning your assumptions, keep
• 20:12
  seeking out those weak signals in the noise,
• 20:14
  and the next time the wind starts howling, remember,
• 20:17
  it might just be time to lock your wings. We'll
• 20:19
  catch you next time.