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Culture Still Eats Strategy. But Now It's Also on the Menu. · Uphoff on Media Podcast

• 0:01
  SPEAKER_00: Welcome to Uphoff on Media, the audio edition.
• 0:05
  SPEAKER_00: I'm Tony Uphoff.
• 0:06
  SPEAKER_00: Each week,
• 0:06
  SPEAKER_00: I write about the collision of agentic AI,
• 0:09
  SPEAKER_00: B2B media,
• 0:09
  SPEAKER_00: marketing,
• 0:10
  and technology from the perspective of someone who's actually
• 0:13
  run these businesses.
• 0:15
  SPEAKER_00: This is the podcast version of my
• 0:16
  Substack publication where I take each post and bring it to you
• 0:20
  in audio form so you
• 0:21
  SPEAKER_00: can listen wherever you are whenever it works for you.
• 0:24
  SPEAKER_00: If you want to read along,
• 0:25
  SPEAKER_00: go deeper,
• 0:25
  SPEAKER_00: or subscribe to the written version,
• 0:27
  SPEAKER_00: you'll find everything at upoffonmedia.substack.com.
• 0:32
  SPEAKER_00: Let's get to work.
• 0:34
  This episode is titled Culture,
• 0:35
  Each Strategy,
• 0:36
  but now it's also on the menu.
• 0:39
  Peter Drucker's most quoted line has never been more relevant
• 0:42
  or,
• 0:43
  frankly,
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  more complicated.
• 0:44
  SPEAKER_00: This episode is a part of my framework series on Substack.
• 0:48
  If you want to download the three visual frameworks included,
• 0:51
  visit upoffonmedia.substack.com.
• 0:56
  SPEAKER_00: Culture eats strategy for breakfast.
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  Leaders have invoked it for decades as a reminder that the
• 1:02
  human architecture of an
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  SPEAKER_00: organization ultimately determines what's possible,
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  SPEAKER_00: regardless of how elegant the strategy is.
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  SPEAKER_00: Get culture wrong and the strategy dies on the whiteboards.
• 1:13
  SPEAKER_00: But here's what Drucker didn't anticipate,
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  the rise of agentic AI and what happens when the cultural self
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  is the most
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  SPEAKER_00: disrupted group,
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  SPEAKER_00: when the people who built your culture,
• 1:24
  SPEAKER_00: who carry it,
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  who embody it every day are the same people most at risk from
• 1:29
  the change you're
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  SPEAKER_00: asking them to embrace.
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  That's the leadership challenge of the agentic AI moment and
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  it's unlike anything
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  SPEAKER_00: executives have navigated before.
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  The challenge of leading organizational culture through AI
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  transformation is now
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  the defining test of B2B executive leadership and the most
• 1:47
  change management
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  SPEAKER_00: frameworks weren't built for it.
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  SPEAKER_00: Why traditional change management fails with AI disruption.
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  SPEAKER_00: Every major disruption of the past three decades,
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  SPEAKER_00: the internet,
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  SPEAKER_00: mobile,
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  SPEAKER_00: cloud,
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  SPEAKER_00: the 2008 financial crisis,
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  SPEAKER_00: tested organizational cultures.
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  SPEAKER_00: Leaders learned hard lessons about change management,
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  SPEAKER_00: communication,
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  SPEAKER_00: and the importance of bringing people along.
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  SPEAKER_00: Entire frameworks are built around it.
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  SPEAKER_00: Cotter's 8-Step, ADCAR, Proceed.
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  SPEAKER_00: The consulting industry made billions helping companies implement them.
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  SPEAKER_00: These frameworks share a common assumption.
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  SPEAKER_00: The workforce is the response team.
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  SPEAKER_00: The disruption arrives from outside.
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  SPEAKER_00: A new competitor, a market collapse, a technological shift.
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  SPEAKER_00: And the leader's job is to rally the organization to meet it.
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  SPEAKER_00: Culture is the obstacle to navigate or the asset to leverage.
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  SPEAKER_00: Either way, the people are on your side of the equation.
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  Cotter's eight-step model and ADCART were built for a world
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  where the workforce was
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  SPEAKER_00: the response team,
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  SPEAKER_00: not the most disrupted constituency.
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  SPEAKER_00: Agentic AI breaks this assumption entirely.
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  SPEAKER_00: In many organizations,
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  SPEAKER_00: the largest portion of the workforce,
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  SPEAKER_00: people in operational,
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  SPEAKER_00: administrative,
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  SPEAKER_00: analytical,
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  and content roles are the ones most directly in the path of
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  AI-driven automation.
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  SPEAKER_00: They're not the response team.
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  They're the most affected constituency,
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  and you're asking them to help lead the transformation.
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  SPEAKER_00: The usual playbook was never designed for this,
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  which is why so many leaders are finding that their
• 3:17
  best-intentioned efforts,
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  SPEAKER_00: the town halls,
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  SPEAKER_00: the AI task forces,
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  SPEAKER_00: the we're investing in people messaging,
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  SPEAKER_00: aren't moving the needle on culture the way they expected.
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  SPEAKER_00: They're not failing because they're doing it wrong.
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  SPEAKER_00: They're failing because they're solving the wrong problem.
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  SPEAKER_00: The trust paradox, why employees don't believe AI reassurances.
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  Here's what actually happens to trust during major disruptions
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  and why most leaders misread it.
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  SPEAKER_00: When organizations face extraordinary change,
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  SPEAKER_00: employees demand more from their leaders,
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  SPEAKER_00: more transparency,
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  SPEAKER_00: more honesty, more reassurance.
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  SPEAKER_00: Trust becomes the dominant cultural conversation.
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  SPEAKER_00: Leaders respond the way they've been trained to.
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  SPEAKER_00: They work to rebuild the employer-employee relationship,
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  SPEAKER_00: more communication,
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  SPEAKER_00: more visibility,
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  SPEAKER_00: more town halls,
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  SPEAKER_00: and more open door moments.
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  SPEAKER_00: And it doesn't work.
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  SPEAKER_00: The trust metrics don't improve.
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  SPEAKER_00: The anxiety doesn't subside.
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  SPEAKER_00: The cultural resistance hardens.
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  SPEAKER_00: The reason is this.
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  SPEAKER_00: The trust that's actually eroding isn't trust in the company.
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  SPEAKER_00: It's trust in the future.
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  SPEAKER_00: Specifically,
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  it's employees trust that their skills will remain relevant and
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  that their career
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  SPEAKER_00: trajectories will survive,
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  that the professional identities they built over years or
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  decades will still mean
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  SPEAKER_00: something on the other side of this transition.
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  SPEAKER_00: That's not a relationship problem.
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  No amount of authentic communication or leadership visibility
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  repairs it because
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  the honest answer to will I be okay is one no leader can give
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  with certainty and
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  SPEAKER_00: employees know it.
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  SPEAKER_00: This is the trust paradox.
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  Employees are losing trust in the future and expressing it as
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  distrust of their employer.
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  Leaders diagnose a relationship problem and try to fix it with
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  relationship tools.
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  SPEAKER_00: The gap between the intervention and the actual need widens,
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  and employees who know exactly what they're afraid of lose even
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  more confidence
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  SPEAKER_00: when they see leadership dancing around the real question.
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  I watched this play out with unusual clarity when I was running
• 5:17
  UBM TechWeb during
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  SPEAKER_00: the 2008 financial crisis.
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  SPEAKER_00: We weren't managing one disruption.
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  SPEAKER_00: We were managing four simultaneously.
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  SPEAKER_00: The structural decline of print,
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  SPEAKER_00: a digital business still proving its economics,
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  SPEAKER_00: an advanced portfolio we were actively acquiring and globalizing,
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  SPEAKER_00: and a workforce spread across the US,
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  SPEAKER_00: UK,
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  SPEAKER_00: India,
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  SPEAKER_00: and China.
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  The anxiety inside the organization wasn't primarily about the
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  financial crisis as
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  SPEAKER_00: severe as that was.
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  SPEAKER_00: It was about the medium.
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  Print journalists and advertising sales professionals who had
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  built 20-year careers
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  were watching their professional world contract in ways that
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  felt permanent.
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  SPEAKER_00: And they were right.
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  SPEAKER_00: We were bringing in new digital leaders,
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  SPEAKER_00: launching new digital products,
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  SPEAKER_00: making a sharp strategic pivot towards events.
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  SPEAKER_00: No market recovery was going to reverse any of it.
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  SPEAKER_00: They didn't need reassurance.
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  SPEAKER_00: They needed something more honest and more useful.
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  SPEAKER_00: What I learned leading through that period,
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  the leaders who navigate disruption successfully aren't the
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  ones who rebuild trust
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  SPEAKER_00: most effectively.
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  SPEAKER_00: They're the ones who stop trying to fix the wrong problem.
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  SPEAKER_00: First move, radical transparency about AI's impact.
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  The most counterintuitive thing a leader can do right now is
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  also the most important.
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  SPEAKER_00: Say out loud what everybody already knows.
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  SPEAKER_00: Your employees are reading the same headlines you are.
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  SPEAKER_00: They're using AI tools at home.
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  SPEAKER_00: They're having conversations with colleagues,
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  SPEAKER_00: partners,
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  SPEAKER_00: and recruiters that you're not in the room for.
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  SPEAKER_00: The disruption is not a secret.
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  SPEAKER_00: The anxiety is not hidden.
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  SPEAKER_00: And any attempt to soften,
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  SPEAKER_00: sequence,
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  SPEAKER_00: or carefully manage the narrative reads accurately as avoidance.
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  SPEAKER_00: Transparency in this context isn't a communication strategy.
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  SPEAKER_00: It's a leadership stance.
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  SPEAKER_00: It means walking into the room and saying,
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  here is what we know about what Agenda AI will change in this
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  organization.
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  SPEAKER_00: Here's what we generally don't know yet.
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  SPEAKER_00: and here's how we intend to navigate it together.
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  SPEAKER_00: That last word carries weight,
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  SPEAKER_00: not here's what we're doing to you,
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  SPEAKER_00: not here's what we're doing for you,
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  SPEAKER_00: here's what we're navigating together.
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  SPEAKER_00: Change at this scale cannot be snuck up on.
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  SPEAKER_00: The disruption is too visible.
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  SPEAKER_00: The anxieties are rising too fast.
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  Leaders who wait for the right moment to have the honest
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  conversation are ceding
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  SPEAKER_00: the narrative to rumor,
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  SPEAKER_00: speculation,
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  SPEAKER_00: and fear,
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  SPEAKER_00: all of which fill the vacuum faster than any town hall can address.
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  SPEAKER_00: The counterintuitive truth,
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  SPEAKER_00: naming the disruption explicitly,
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  SPEAKER_00: including the uncertainty,
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  builds more durable credibility than projecting confidence you
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  don't fully have.
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  Because when you subsequently make the case for where you were
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  going and why,
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  people believe it.
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  SPEAKER_00: You haven't asked them to disbelieve what they can already see.
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  SPEAKER_00: Name it, don't manage it.
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  SPEAKER_00: Second move, build navigational confidence, not just trust.
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  SPEAKER_00: Once you've named the disruption honestly,
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  SPEAKER_00: the next move is equally important and equally counterintuitive.
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  SPEAKER_00: Stop trying to rebuild trust.
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  SPEAKER_00: Start building confidence in the organization's ability to navigate.
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  SPEAKER_00: These sound similar, but they're not.
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  Rebuilding trust is about the relationship between leaders and
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  employees.
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  Building navigational confidence is about the organization's
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  collective capability
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  SPEAKER_00: to move through uncertainty toward something worth reaching.
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  SPEAKER_00: The first is interpersonal, the second is directional.
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  The question employees are actually asking beneath the surface
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  demands for
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  SPEAKER_00: transparency and reassurance isn't,
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  SPEAKER_00: do I trust you?
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  SPEAKER_00: It's, do you know where we're going and can we get there?
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  SPEAKER_00: That question requires a different answer, not reassurance, navigation.
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  This is where AI strategy and culture have to connect
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  specifically and concretely,
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  SPEAKER_00: not abstractly.
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  SPEAKER_00: We're investing in AI doesn't move culture.
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  SPEAKER_00: Here is what we're building.
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  SPEAKER_00: Here is why it creates durable competitive advantage.
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  SPEAKER_00: And here is what that means for the roles and capabilities we'll need.
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  That starts to move culture because it gives people a
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  destination to orient toward
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  SPEAKER_00: rather than a threat to brace against.
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  SPEAKER_00: The narrative has to shift from loss to direction.
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  SPEAKER_00: Not everyone will make the transition.
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  SPEAKER_00: That's the honest reality of disruption at this scale.
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  SPEAKER_00: The people who stay need something real to move toward.
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  SPEAKER_00: Abstract strategy doesn't provide that.
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  SPEAKER_00: Specific navigation does.
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  SPEAKER_00: Third move, make employees architects of AI transformation.
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  The deepest cultural shift available to leadership navigating
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  AI disruption is also
• 9:50
  SPEAKER_00: the most underutilized.
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  SPEAKER_00: Bring the most affected employees into the response itself,
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  SPEAKER_00: not as subjects of the transformation,
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  SPEAKER_00: as architects of it.
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  SPEAKER_00: The instinct runs counter to how most organizations approach change.
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  SPEAKER_00: The AI strategy gets built in the C-suite or by a dedicated task force,
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  SPEAKER_00: usually populated with the most tech-forward employees.
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  It gets rolled out to the broader organization as a
• 10:14
  communication exercise.
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  And the people whose role are most directly affected are the
• 10:20
  last to have meaningful input.
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  SPEAKER_00: This is exactly backwards, both strategically and culturally.
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  SPEAKER_00: Strategically,
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  the employees closest to the operational work know where AI can
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  genuinely augment
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  SPEAKER_00: what they do and where the friction will be.
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  That intelligence is invaluable and largely untapped in most AI
• 10:40
  transformation efforts.
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  SPEAKER_00: Culturally,
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  the active participation changed the psychological relationship
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  to the change
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  SPEAKER_00: itself.
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  People who helped shape their response don't experience it the
• 10:49
  same way as people
• 10:50
  SPEAKER_00: who received it.
• 10:51
  SPEAKER_00: The anxiety doesn't disappear, but agency does something to it.
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  SPEAKER_00: It transforms passive fear into active problem solving.
• 11:00
  SPEAKER_00: Practical mechanisms matter here.
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  SPEAKER_00: AI working groups deliberately drawn from the most effective roles,
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  SPEAKER_00: not just the most enthusiastic early adopters.
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  Internal use case development led by frontline employees with
• 11:14
  real operational
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  SPEAKER_00: context,
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  SPEAKER_00: reskilling investments that are specific and credible,
• 11:19
  tied to actual roles in the organization that's building toward
• 11:23
  rather than generic
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  SPEAKER_00: commitments,
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  SPEAKER_00: and visible wins attributed to the workforce,
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  SPEAKER_00: not to leadership or the technology itself.
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  The signal this sends consistently over time is the one that
• 11:34
  actually shifts culture.
• 11:36
  SPEAKER_00: We are navigating this together.
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  SPEAKER_00: You are not subject to this change.
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  SPEAKER_00: You are a part of how we respond to it.
• 11:43
  SPEAKER_00: Leading AI culture change across global organizations.
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  One aspect of AI culture transformation that most discussions
• 11:51
  skip deserves a clear flag.
• 11:53
  SPEAKER_00: Cultural transformation is not culturally neutral.
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  The three moves above have to be applied differently across
• 12:01
  different national and
• 12:02
  SPEAKER_00: organizational cultures.
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  SPEAKER_00: Trust,
• 12:04
  SPEAKER_00: transparency,
• 12:05
  SPEAKER_00: institutional authority,
• 12:06
  SPEAKER_00: and job security carry different weight in the US,
• 12:10
  SPEAKER_00: UK,
• 12:10
  SPEAKER_00: India,
• 12:10
  SPEAKER_00: and China.
• 12:11
  What reads as honest and direct leadership in one context reads
• 12:15
  as alarming or
• 12:16
  SPEAKER_00: disrespectful in another.
• 12:18
  The communication format that works in one office doesn't land
• 12:21
  the same way in another country.
• 12:23
  For executives leading global organizations through AI
• 12:25
  disruption,
• 12:26
  this isn't a footnote.
• 12:28
  SPEAKER_00: The frameworks have to be adapted, not just translated.
• 12:31
  And that adaptation requires local leaders with real authority
• 12:34
  and real context,
• 12:36
  SPEAKER_00: not regional messengers for a centrally designed transformation.
• 12:43
  SPEAKER_00: The leadership moment this requires.
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  SPEAKER_00: Most executives were trained to lead from a position of confidence,
• 12:49
  SPEAKER_00: project clarity,
• 12:50
  SPEAKER_00: manage the narrative,
• 12:51
  protect the organization from uncertainty until you have
• 12:54
  answers worth giving.
• 12:55
  SPEAKER_00: That's not bad leadership.
• 12:56
  SPEAKER_00: It's what most disruptions have required.
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  SPEAKER_00: This one requires something different.
• 13:01
  The agentic AI disruption is happening in plain sight at a pace
• 13:05
  that outstrips any
• 13:06
  organization's ability to get ahead of it to a workforce that
• 13:09
  is simultaneously
• 13:11
  SPEAKER_00: your greatest cultural asset and the most directly affected constituency.
• 13:16
  SPEAKER_00: The old tools,
• 13:17
  SPEAKER_00: the managed rollouts,
• 13:18
  SPEAKER_00: the optimistic town hall,
• 13:20
  the trust rebuilding initiative aren't failing because leaders
• 13:24
  are applying them
• 13:24
  SPEAKER_00: poorly.
• 13:25
  SPEAKER_00: They're failing because the situation has changed in a fundamental way.
• 13:29
  What this moment requires is leaders willing to step into the
• 13:32
  uncertainty visibly
• 13:34
  to trade the appearance of control for the credibility of
• 13:37
  honesty and to build
• 13:38
  cultures that can navigate what isn't fully known yet rather
• 13:42
  than cultures waiting
• 13:43
  SPEAKER_00: for permission to engage with it.
• 13:46
  That is harder than anything the standard change management
• 13:48
  curriculum prepared anyone for.
• 13:50
  It demands a tolerance for ambiguity that doesn't come
• 13:53
  naturally to most people who
• 13:54
  SPEAKER_00: reach the C-suite.
• 13:55
  SPEAKER_00: And it requires a genuine belief that your people,
• 13:59
  SPEAKER_00: including the ones most at risk,
• 14:01
  are capable of being part of the answer rather than just
• 14:05
  recipients of it.
• 14:06
  SPEAKER_00: Name it, reframe it, own it.
• 14:09
  SPEAKER_00: That sequence won't eliminate the anxiety,
• 14:11
  SPEAKER_00: nothing will,
• 14:12
  but it will give your people and your culture something the
• 14:15
  optimistic town hall
• 14:16
  SPEAKER_00: never could,
• 14:17
  SPEAKER_00: a reason to believe the navigation is real.
• 14:21
  The leaders who get this right won't be remembered for having
• 14:23
  the best AI strategy.
• 14:25
  They'll be remembered for building organizations that could
• 14:28
  actually execute one
• 14:30
  because the culture was ready and the people trusted the
• 14:32
  navigation even when the
• 14:34
  SPEAKER_00: destination wasn't fully in view.
• 14:36
  SPEAKER_00: That's what leading through disruption has always meant at its best.
• 14:40
  This moment just makes the demand more visible and the stakes
• 14:43
  harder to ignore.
• 14:45
  SPEAKER_00: Hey, thanks for listening, and one more thing.
• 14:48
  SPEAKER_00: The views expressed in UpHuff and Media are entirely my own.
• 14:51
  SPEAKER_00: They don't represent the opinions of any company I've led,
• 14:54
  SPEAKER_00: any board I've sat on,
• 14:55
  or any investor who's had the pleasure of debating strategy
• 14:58
  with me over the years.
• 15:00
  SPEAKER_00: If something I write here sounds brilliant, I'll take full credit.
• 15:03
  SPEAKER_00: If it turns out to be wrong, I was clearly misquoted by myself.
• 15:07
  SPEAKER_00: Thanks very much.