Latest / Uphoff on Media Podcast / Be Careful What You Wish For

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Be Careful What You Wish For · Uphoff on Media Podcast

• 0:02
  SPEAKER_00: Over a 35-year career in five CEO roles,
• 0:05
  SPEAKER_00: there is one question I've been asked more than any other.
• 0:09
  SPEAKER_00: Do I have what it takes to get into management?
• 0:13
  SPEAKER_00: Sales reps thinking about becoming sales managers,
• 0:16
  SPEAKER_00: marketing specialists looking to become marketing directors,
• 0:19
  SPEAKER_00: and many more times than I can count,
• 0:22
  SPEAKER_00: senior leaders wondering if they had the potential to take on C-level roles.
• 0:27
  SPEAKER_00: In most every case, my response was the same.
• 0:30
  SPEAKER_00: Be careful what you wish for.
• 0:32
  SPEAKER_00: Leadership roles may not be what you think they are.
• 0:35
  SPEAKER_00: They come at a cost and not everyone is suited for them.
• 0:39
  SPEAKER_00: After a recent career advice discussion with mid-level manager trying
• 0:44
  SPEAKER_00: to figure out their next step,
• 0:45
  SPEAKER_00: I decided to share my business leadership journey,
• 0:48
  SPEAKER_00: the lessons learned,
• 0:49
  SPEAKER_00: and a framework that may help you determine which seat you're most suited for.
• 0:54
  SPEAKER_00: Interestingly enough,
• 0:55
  SPEAKER_00: it all started with a book about a presidential race that I read
• 0:58
  SPEAKER_00: while holding our one-year-old daughter on my chest.
• 1:02
  SPEAKER_00: Okay, let's get to work.
• 1:05
  SPEAKER_00: This episode is titled, Be Careful What You Wish For.
• 1:09
  SPEAKER_00: Early in my career, I read a 1,047 page book about six men who wanted to be president.
• 1:16
  SPEAKER_00: It told me I was built for leadership, but what it warned me about took longer to learn.
• 1:22
  SPEAKER_00: I was a newly minted VP at Ziff Davis in a job that felt way over my head and likely was.
• 1:29
  SPEAKER_00: With my one-year-old daughter asleep on my chest, I started reading What It Takes.
• 1:33
  SPEAKER_00: I thought I was reading a book about a presidential primary.
• 1:37
  SPEAKER_00: I didn't realize I was reading a book that would help me identify
• 1:39
  SPEAKER_00: a massive challenge I was facing.
• 1:42
  SPEAKER_00: It told me I was built for business leadership.
• 1:45
  SPEAKER_00: It also warned me something would break if I didn't get smarter about managing it.
• 1:52
  SPEAKER_00: Richard Ben Kramer's What It Takes,
• 1:54
  SPEAKER_00: The Way to the White House is about six men who wanted to be president.
• 1:57
  SPEAKER_00: My daughter Olivia was one year old and somewhere in the middle of that brick of
• 2:02
  SPEAKER_00: a book,
• 2:02
  SPEAKER_00: I stopped reading it as political history and started reading it as a mirror.
• 2:07
  SPEAKER_00: Kramer didn't write about policy, he wrote about appetite.
• 2:10
  SPEAKER_00: What makes six people volunteer for the worst job interview in the world?
• 2:15
  SPEAKER_00: 18 months of having their entire life picked apart in public on the chance they get
• 2:19
  SPEAKER_00: to do something enormous.
• 2:22
  SPEAKER_00: 34 years later, that's still the only question in the book worth remembering.
• 2:28
  SPEAKER_00: Crazy enough was the easy takeaway.
• 2:30
  SPEAKER_00: The harder one took longer to learn.
• 2:33
  SPEAKER_00: Some part of me already suspected I had the temperament for what I was stepping into.
• 2:38
  SPEAKER_00: I didn't shrink from decisions made without enough information,
• 2:41
  SPEAKER_00: and I wasn't especially afraid of being wrong in front of people
• 2:44
  SPEAKER_00: who could make my life difficult about it.
• 2:46
  SPEAKER_00: Kramer's book confirmed that part quickly.
• 2:50
  SPEAKER_00: Six people,
• 2:50
  SPEAKER_00: three Republicans,
• 2:51
  SPEAKER_00: effectively down to two,
• 2:53
  SPEAKER_00: four Democrats,
• 2:54
  SPEAKER_00: all of them certifiably a little crazy in the same specific way,
• 2:57
  SPEAKER_00: willing to trade a normal life for a shot and an impossible one.
• 3:02
  SPEAKER_00: The second lesson took longer and it was the one that actually mattered.
• 3:06
  SPEAKER_00: Wanting a job badly enough to survive it and knowing how to carry it
• 3:09
  SPEAKER_00: without dropping everything else are not the same skill.
• 3:12
  SPEAKER_00: I had the first one,
• 3:14
  SPEAKER_00: I was still working on the second and the evidence was standing right in front
• 3:18
  SPEAKER_00: of me every night.
• 3:19
  SPEAKER_00: A business demanding more of me than I knew how to give it efficiently,
• 3:23
  SPEAKER_00: a marriage that needed attention I wasn't always paying,
• 3:26
  SPEAKER_00: a daughter who wouldn't be a one-year-old twice.
• 3:29
  SPEAKER_00: Something was going to break if I kept running leadership on instinct instead of a system.
• 3:35
  SPEAKER_00: I still get some version of the same question every few months,
• 3:38
  SPEAKER_00: usually from someone weighing a move into management who wants me to tell them
• 3:42
  SPEAKER_00: whether they should take it.
• 3:43
  SPEAKER_00: My answer hasn't changed since I first heard myself say it out loud.
• 3:47
  SPEAKER_00: Be careful what you wish for.
• 3:52
  SPEAKER_00: That question deserves a real answer, not just a warning.
• 3:55
  SPEAKER_00: That line was never meant to talk anyone out of leadership.
• 3:59
  SPEAKER_00: It was meant to make them actually answer the question instead of just wanting the title.
• 4:03
  SPEAKER_00: Most people who ask are conflating two different things,
• 4:07
  SPEAKER_00: wanting the exposure and status that comes with the title and being built for
• 4:11
  SPEAKER_00: the actual mechanics of doing the job,
• 4:13
  SPEAKER_00: deciding without complete information and getting judged in public for
• 4:17
  SPEAKER_00: the decision either way.
• 4:18
  SPEAKER_00: Those are separable and running one against the other tells you more than either one alone.
• 4:26
  SPEAKER_00: Plot tolerance for ambiguity,
• 4:28
  SPEAKER_00: how you decide before the picture is complete,
• 4:30
  SPEAKER_00: against appetite for exposure,
• 4:32
  SPEAKER_00: how you hold up being watched,
• 4:34
  SPEAKER_00: wrong, and reassessed in public, and four seats show up, not one.
• 4:40
  SPEAKER_00: High on both is the candidate quadrant.
• 4:43
  SPEAKER_00: Kramer's six all live there,
• 4:45
  SPEAKER_00: not because they were the smartest people in the race,
• 4:48
  SPEAKER_00: but because they could stay on the roof.
• 4:50
  SPEAKER_00: Low ambiguity tolerance paired with high appetite for exposure is the performer,
• 4:55
  SPEAKER_00: commanding once the plan is set, exposed the moment it isn't.
• 4:59
  SPEAKER_00: High ambiguity tolerance paired with low appetite for exposure is the strategist,
• 5:04
  SPEAKER_00: seeing three moves ahead and genuinely fine not knowing how it resolves as long
• 5:08
  SPEAKER_00: as their name isn't the one attached to the outcome in public.
• 5:12
  SPEAKER_00: Low on both is the specialist doing the org's best work against a clear brief,
• 5:17
  SPEAKER_00: someone for whom both ambiguity and scrutiny drain rather than sharpen.
• 5:25
  SPEAKER_00: I landed in the candidate quadrant early in my career,
• 5:28
  SPEAKER_00: and that told me almost nothing useful by itself.
• 5:31
  SPEAKER_00: It told me I could survive the job.
• 5:33
  SPEAKER_00: It didn't tell me I knew how to run it without a system underneath me,
• 5:36
  SPEAKER_00: and that gap nearly caught up with me.
• 5:40
  SPEAKER_00: The scrutiny used to have an off switch, now it doesn't.
• 5:44
  SPEAKER_00: Every one of Kramer's candidates got a concession speech.
• 5:47
  SPEAKER_00: Win or lose,
• 5:48
  SPEAKER_00: a day arrived when the campaign ended,
• 5:50
  SPEAKER_00: the coverage moved on, and the verdict closed.
• 5:53
  SPEAKER_00: Business leadership used to run on its own quieter version of that system.
• 5:58
  SPEAKER_00: A bad quarter got explained away by the next earnings call.
• 6:01
  SPEAKER_00: A rough town hall got buried under Monday's news cycle.
• 6:05
  SPEAKER_00: A 360 review happened once a year on a schedule a leader could see coming and prepare for.
• 6:10
  SPEAKER_00: The evaluation had a rhythm, and the rhythm had recovery time built into it.
• 6:15
  SPEAKER_00: That rhythm is gone, and it didn't fade out gradually.
• 6:19
  SPEAKER_00: I've argued that this same cycle used to exist on the sales side of B2B,
• 6:23
  SPEAKER_00: a human somewhere in the loop who could feel when something was off
• 6:27
  SPEAKER_00: and course correct before it became a lost deal nobody could explain.
• 6:32
  SPEAKER_00: Agentic AI is doing the identical thing to how leaders themselves get evaluated.
• 6:38
  SPEAKER_00: An agent summarizing a week of all hands transcripts doesn't wait for
• 6:42
  SPEAKER_00: the quarterly engagement survey to catch the gap between what a leader said and what
• 6:46
  SPEAKER_00: the room actually heard.
• 6:48
  SPEAKER_00: A sentiment tool reading internal slack doesn't need a listening tour scheduled
• 6:52
  SPEAKER_00: before it clocks that morale moved.
• 6:54
  SPEAKER_00: A board member watching a live dashboard doesn't need the deck to ask why
• 6:58
  SPEAKER_00: a number shifted in the last 48 hours.
• 7:01
  SPEAKER_00: Ground Truth doesn't wait for the annual review anymore.
• 7:04
  SPEAKER_00: It updates continuously and it doesn't ask permission first.
• 7:10
  SPEAKER_00: The key takeaway here isn't more monitoring.
• 7:13
  SPEAKER_00: It's the disappearance of the recovery window.
• 7:16
  SPEAKER_00: Episodic scrutiny gave a leader a window to have a bad week and fix it before
• 7:20
  SPEAKER_00: the bad week became the story.
• 7:22
  SPEAKER_00: Continuous scrutiny shrinks that window to almost nothing.
• 7:26
  SPEAKER_00: Every live signal is a small ongoing referendum and
• 7:29
  SPEAKER_00: the referendum never adjourns long enough for anyone to catch their breath.
• 7:33
  SPEAKER_00: That changes what crazy enough has to mean now.
• 7:38
  SPEAKER_00: Kramer's candidates needed the temperament to survive one campaign with
• 7:41
  SPEAKER_00: a clear end date and a known finish line.
• 7:44
  SPEAKER_00: The same temperament today has to run several overlapping evaluations at once on
• 7:49
  SPEAKER_00: a clock that never calls a recess.
• 7:53
  SPEAKER_00: The same six traits, every one of them wearing a different shape.
• 7:57
  SPEAKER_00: Everyone who's asked me some version of should I take this job over
• 8:01
  SPEAKER_00: the last three decades was really asking about six things.
• 8:05
  SPEAKER_00: Resilience,
• 8:07
  SPEAKER_00: tolerance for ambiguity,
• 8:08
  SPEAKER_00: the discipline to let some fires burn so you can fight the ones that matter,
• 8:12
  SPEAKER_00: the ability to take and carry real risk,
• 8:15
  SPEAKER_00: optimism,
• 8:16
  SPEAKER_00: and whether they had anyone around them
• 8:18
  SPEAKER_00: who could catch what they couldn't see themselves.
• 8:22
  SPEAKER_00: None of the six are new.
• 8:23
  SPEAKER_00: Here's what continuous scrutiny did to each.
• 8:28
  SPEAKER_00: Number one, resilience.
• 8:30
  SPEAKER_00: Used to be measured in quarters, a bad stretch absorbed by a good one three months later.
• 8:34
  SPEAKER_00: Continuous sentiment and performance signal collapses that runway to almost nothing.
• 8:39
  SPEAKER_00: A leader's response to one difficult week is now legible and near real time instead
• 8:44
  SPEAKER_00: of filed away until the next board deck.
• 8:46
  SPEAKER_00: And the recovery has to happen on the same compressed clock the scrutiny runs on.
• 8:52
  SPEAKER_00: Number two,
• 8:53
  SPEAKER_00: tolerance for ambiguity used to mean that data wasn't in yet,
• 8:56
  SPEAKER_00: and the skill was patience, knowing how long to wait before you moved.
• 9:00
  SPEAKER_00: More often now,
• 9:01
  SPEAKER_00: the data is in constantly,
• 9:03
  SPEAKER_00: streaming from a dozen live sources at once,
• 9:06
  SPEAKER_00: and the harder skill is deciding while
• 9:08
  SPEAKER_00: the picture keeps moving underneath you instead of holding still long enough
• 9:11
  SPEAKER_00: to read it.
• 9:13
  SPEAKER_00: Number three, letting fires burn.
• 9:15
  SPEAKER_00: It's harder before it gets easier.
• 9:17
  SPEAKER_00: Agents surface more signal,
• 9:18
  SPEAKER_00: not less,
• 9:19
  SPEAKER_00: more anomalies flag, more decisions that technically require a human sign off.
• 9:24
  SPEAKER_00: The skill shifts from knowing which fires to walk past to building
• 9:27
  SPEAKER_00: a real triage system for the fires a machine hands you before you've noticed
• 9:32
  SPEAKER_00: the smoke yourself.
• 9:34
  SPEAKER_00: Number four, managing risk now includes a category framers candidates never had to deal with.
• 9:40
  SPEAKER_00: The exposure created by handing judgment to a system nobody in
• 9:44
  SPEAKER_00: the room can fully audit in real time and answering for its calls as
• 9:48
  SPEAKER_00: if they were your own because to the board and the market, they are.
• 9:52
  SPEAKER_00: Number five,
• 9:53
  SPEAKER_00: optimism has to stay grounded instead of promotional because
• 9:56
  SPEAKER_00: the promotional version doesn't survive contact with a dashboard
• 9:59
  SPEAKER_00: that updates hourly.
• 10:01
  SPEAKER_00: The clearest recent example wasn't a founder's keynote.
• 10:05
  SPEAKER_00: It was three departing CEOs telling their board As I wrote when Doug McMillan
• 10:12
  SPEAKER_00: of Walmart,
• 10:12
  SPEAKER_00: James Quincy of Coca-Cola,
• 10:15
  SPEAKER_00: and Shantanu Narayan of Adobe all made a version of the same call within months
• 10:20
  SPEAKER_00: of each other.
• 10:21
  SPEAKER_00: The real optimism in that moment wasn't, I can do this.
• 10:24
  SPEAKER_00: It was, this is worth doing whether or not I'm the one who finishes it.
• 10:30
  SPEAKER_00: And number six,
• 10:30
  SPEAKER_00: support systems is the trait I have the least patience for people skipping,
• 10:35
  SPEAKER_00: mostly because it's the one I skip longest myself.
• 10:38
  SPEAKER_00: And it's the trait continuous scrutiny punishes fastest.
• 10:42
  SPEAKER_00: It covers more than having someone to call when things get hard.
• 10:46
  SPEAKER_00: It means a leadership team strong enough to catch what you can't see about yourself,
• 10:51
  SPEAKER_00: a management structure that keeps running when you're not the one holding it up,
• 10:55
  SPEAKER_00: and enough deliberate structure at home to keep a marriage and a family
• 10:58
  SPEAKER_00: from surviving on whatever attention is left over at the end of the day.
• 11:04
  SPEAKER_00: A leader with nowhere to process a hard week at the office or at the kitchen table
• 11:08
  SPEAKER_00: before the next signal lands starts making decisions from fatigue instead
• 11:13
  SPEAKER_00: of judgment.
• 11:15
  SPEAKER_00: The trade I nearly failed.
• 11:17
  SPEAKER_00: Here's what actually would have broken early in my career
• 11:20
  SPEAKER_00: if I hadn't taken Kramer's second verdict seriously.
• 11:23
  SPEAKER_00: Not the business.
• 11:24
  SPEAKER_00: I was resilient enough,
• 11:25
  SPEAKER_00: ambitious enough, comfortable enough with ambiguity to keep the job moving.
• 11:29
  SPEAKER_00: What was at risk was the husband and the father fully showing up in addition to
• 11:34
  SPEAKER_00: the business leader.
• 11:35
  SPEAKER_00: And I didn't fix that by trying harder.
• 11:37
  SPEAKER_00: I fixed it by building actual structure around how I ran my time
• 11:42
  SPEAKER_00: and my attention instead of assuming strength of will alone would cover the gap.
• 11:46
  SPEAKER_00: The data on this hasn't gotten friendlier.
• 11:50
  SPEAKER_00: Somewhere between 55 and 60 percent of CEOs report feeling isolated at
• 11:54
  SPEAKER_00: the job they fought so hard to get.
• 11:56
  SPEAKER_00: Nearly all of them say they'd welcome coaching or outside counsel.
• 12:00
  SPEAKER_00: Roughly two-thirds get none.
• 12:03
  SPEAKER_00: New leaders have it even worse.
• 12:05
  SPEAKER_00: More than seven in ten say they felt lonelier in the early stretch of a new role
• 12:09
  SPEAKER_00: than they did before they stepped into it.
• 12:11
  SPEAKER_00: The instinct that gets rewarded on the way up,
• 12:14
  SPEAKER_00: carry it yourself,
• 12:16
  SPEAKER_00: is precisely the instinct that has to be unlearned once you're actually in the seat.
• 12:21
  SPEAKER_00: I didn't build a peer group or hire a coach early in my career.
• 12:24
  SPEAKER_00: I didn't have the language for what I needed yet.
• 12:27
  SPEAKER_00: What I did have was a book that scared me into taking the second lesson as seriously
• 12:31
  SPEAKER_00: as the first and enough sense to start building something more deliberate
• 12:35
  SPEAKER_00: than instinct before home life was significantly impacted.
• 12:41
  SPEAKER_00: Three of the four quadrants are leadership too.
• 12:44
  SPEAKER_00: Not everyone belongs in the candidate quadrant and
• 12:46
  SPEAKER_00: the other three quadrants were never the lesser answer.
• 12:50
  SPEAKER_00: The performer runs the room once the plan is set and deserves
• 12:53
  SPEAKER_00: a real system around them instead of a lecture about toughening up.
• 12:57
  SPEAKER_00: The strategist is often the best chief of staff or strategy chief
• 13:01
  SPEAKER_00: a candidate will ever have, not a leader who fell short.
• 13:05
  SPEAKER_00: The specialist does work most organizations can't survive without,
• 13:08
  SPEAKER_00: and the next move from there should be toward mastery,
• 13:11
  SPEAKER_00: not toward a title that was never the right fit to begin with.
• 13:16
  SPEAKER_00: Be careful what you wish for was never a warning to stay small.
• 13:20
  SPEAKER_00: It was an instruction to find out which
• 13:22
  SPEAKER_00: of these four quadrants you're actually built for before you take the promotion,
• 13:26
  SPEAKER_00: not after you're already in the job and something at home is starting to give.
• 13:31
  SPEAKER_00: Olivia's all grown up now with children of her own and the book is still on my shelf.
• 13:36
  SPEAKER_00: Prioritizing my family didn't cost the business anything.
• 13:39
  SPEAKER_00: It made me a better leader and it made those years worth living, not just surviving.
• 13:44
  SPEAKER_00: What I remember about the book Isn't the six candidates.
• 13:47
  SPEAKER_00: It's the young business leader holding his daughter,
• 13:50
  SPEAKER_00: finding out the hard way that wanting the job and knowing how
• 13:53
  SPEAKER_00: to carry it are two different tests and that you better pass both.
• 13:59
  SPEAKER_00: Well, that's it for this episode.
• 14:01
  SPEAKER_00: If you found this useful, please do one thing.
• 14:04
  SPEAKER_00: Follow the Uphoff on Media podcast on Apple or Spotify and leave a rating.
• 14:08
  SPEAKER_00: It's the single best way to help another operator find this.
• 14:12
  SPEAKER_00: I'm Tony Uphoff, back at it next week.