Depthfinding: Sky - Threats and Opportunities - At Work with The Ready

Episode Overview

Episode Title: Depthfinding: Sky – Threats and Opportunities
Hosts: Rodney Evans and Sam Spurlin
Date: January 27, 2025
Podcast: At Work with The Ready

In this episode, Rodney and Sam dive into the "sky" layer of their Depthfinding framework—a metaphor for the external forces impacting organizations, such as technology shifts, marketplace dynamics, climate, and politics. They explore why organizations struggle to pay attention to external change, the consequences of that inattention, and practical approaches to scanning for both threats and opportunities. With a mix of organizational examples and personal reflection, they pull apart why most teams are reactive (or oblivious) and outline ways to make “sky work” a healthy and habitual part of both personal and organizational practices.

Key Discussion Points and Insights

1. The "Sky" in Depthfinding: A Metaphor for the External Why

The "sky" encompasses all external forces—technological, social, economic, political, and environmental—that organizations exist within and must respond to if they’re to survive and thrive ([03:00]–[05:00]).
Most organizations are "internally myopic," rarely looking up to consider what’s changing around them until a crisis emerges.
Rodney: "The hard reality of being in especially a leadership role in any business is like every business decays. It just does. And the way that you know how it's going to decay is by paying attention to what's going on out there." ([06:26])

2. Sky as Both Threats and Opportunities

While most leaders instinctively notice threats (the dinosaur or meteor coming for your business), the sky is equally full of underexploited opportunities ([08:30]–[10:30]).
Human psychology and organizational habits tend to focus on pain avoidance vs. gain pursuit, often leaving innovation on the table.
Sam: "There’s this whole other side, the whole opportunity cost of things not done that are also in the sky. And you don’t know to pursue those if you’re not regularly engaging with it..." ([08:33])

3. Sky is Multilayered and Personal

Every function and role has its own unique "sky": the external forces shaping HR aren't the same as those shaping finance or product teams ([11:00]–[12:50]).
Healthy organizations encourage teams to track trends relevant to their unique context.

4. Sensemaking is Social, Not Solitary

Effective sky-scanning isn’t a solo act. Group sensemaking—coming together to share, debate, and synthesize external signals—is vital ([13:36]–[14:45]).
"Depth finding is a team sport," says Rodney. The interplay of individual curiosity and collective reflection distinguishes robust sky work.

5. Texture Over Checklists

It’s not just about tracking headlines or making trend lists. Successful leaders and teams develop "texture"—an intuition built from ongoing engagement and deep, diverse information ([14:37]–[15:28]).
Quick fixes or borrowed strategy frameworks often miss this richness.

6. Why Sky Work Often Fails

The "anti-example": Leadership teams express a desire to do strategic, sky-focused work, but lack rituals, rhythms, or space to actually engage in it ([20:43]–[24:00]).
Strategy development becomes performative: “By May, nobody can find the deck. And by, you know, September we're talking about next year's and with like no memory of what it was before." – Sam ([23:27])
Disconnect between declared aims and true external drivers leads to generic, unimpactful solutions.

7. Making Sky Work Part of the Rhythm

Carve out explicit time for sky work, e.g., Friday sessions to discuss external articles or trends ([27:44]–[28:13]).
Importantly, talk to people outside your organization to avoid echo chambers.

8. Individual and Collective Practices

There’s much individuals can do: reading, journaling, having prediction and review cycles, using AI tools to surface personalized trend analysis ([29:07]–[33:48]).
But collective synthesis—building a shared sense of threats and opportunities—is critical for real impact.

9. The “Ready” Example: Practicing What They Preach

The Ready has redesigned much of its own operating rhythm to integrate sky work, dedicating ~50% of its time on external sensing ([34:00]–[38:42]).
Rodney describes using scenario planning, red teaming, and engaging all members to collectively sense where their sector is going.
Adapting to dwindling client appetite for “ways of working” required them to shift toward helping on clearly sky-connected problems.

10. Creative, Imaginative Sky Work

Reading fiction (especially science fiction) can broaden leaders’ ability to imagine futures—a helpful practice for sky work ([18:03]–[19:23]).
Sam: "A leader who has a robust fiction reading habit…is likely to have a more sensitive and nuanced take on the sky..." ([18:03])

11. Don’t Rush into Execution

Resist the urge to immediately “action” every trend. Stew, experiment, and let clarity emerge ([41:19]–[44:41]).
Stew vs. omelette metaphor: "We want stew in this. We want to develop those flavors." – Sam ([43:42])

12. Impact at the Individual Level

Individuals who invest in sky work feel more confident and deliberate, even (especially) when making bold bets ([47:01]).

Notable Quotes & Memorable Moments

On decay and sky vigilance:
"Every business decays. It just does. And the way that you know how it's going to decay is by paying attention to what's going on out there..." – Rodney ([06:26])
On collective sensemaking:
"It is through the way that I talk about my interpretation of the sky and the way you talk about your interpretation of the sky that we actually create a new and better different take on what is actually happening..." – Sam ([12:50])
On performative strategy:
"February, we're all stoked about the new strategy. By May, nobody can find the deck. And by September, we're talking about next year's with no memory of what it was before." – Sam ([23:27])
On the necessity but rarity of 'sky work':
"...I just don't think that most leadership teams, in particular, make a lot of time for it." – Rodney ([14:37])
On individual sky practices:
"There's so much to be done as an individual where you don't need the buy-in of literally anybody else to really level up your ability to interact with the sky." – Sam ([29:07])
On stew versus omelette as a change metaphor:
"We're making a stew here, not making an omelette... Both are delicious, but only one is fast." – Sam & Rodney ([43:42])
On imaginative practices:
"Sky practices are imaginative in nature... you have to then imagine a future that may or may not exist." – Rodney ([19:23])
On the “magic” of shared sky work:
"When one of us posits a guess at what the play is, the rest of us go like, 'Yeah, that seems right.'...And that feels like magic. That feels like a magic trick." – Rodney ([46:57])

Timestamps for Important Segments

03:00–05:15: Introduction to the “sky” metaphor and why most orgs ignore it
06:26: Rodney on the inevitability of decay and the "paranoia" needed to avoid it
08:33: Sam on opportunity costs and the human tendency to notice threats
11:04–12:50: Multiple skies – Every function/team faces its own unique set of threats/opportunities
13:36–14:45: Why group sensemaking is superior to top-down sky analysis
18:03–19:23: The value of fiction and imagination in future-facing leadership
20:43–24:00: The “anti-example” where leadership wishes for strategy but refuses to build the practices
27:44–29:07: Practical tips for building sky work into the operating rhythm
34:00–38:42: How The Ready has institutionalized sky work internally
41:19–44:41: Letting sensemaking stew—don’t rush into execution
46:57: The magic of synchronized collective understanding
47:01: Confidence that comes from deliberate sky work

Practical Recommendations & Takeaways

Don’t rely on structure alone (e.g., OKRs, matrix reporting) for sky work—build explicit, recurring practices.
Balance the focus on opportunity and threat; don’t default to fear alone.
Encourage individual curiosity AND collective sensemaking; both are necessary for resilient strategy.
Read widely—including fiction—to build imagination muscles.
Make “external sensing” a rhythm, not a one-off; talk to outsiders, use liberating structures, and let new direction emerge organically.
Mix individual and organizational data sources—client feedback, team member insights, competitor moves, external advisors, publicly available information.
Give sky scenarios time to percolate rather than forcing instant plans and actions.

The episode is a rich, candid exploration of how teams can radically improve by building regular, creative "sky work" into their DNA—while calling out why so many fail to do so. Whether you’re a leader, team member, or consultant, the episode offers actionable wisdom on making external awareness an engine for adaptive, intentional, and meaningful change.

Episode Overview

Episode Title: Depthfinding: Sky – Threats and Opportunities
Hosts: Rodney Evans and Sam Spurlin
Date: January 27, 2025
Podcast: At Work with The Ready

Key Discussion Points and Insights

1. The "Sky" in Depthfinding: A Metaphor for the External Why

The "sky" encompasses all external forces—technological, social, economic, political, and environmental—that organizations exist within and must respond to if they’re to survive and thrive ([03:00]–[05:00]).
Most organizations are "internally myopic," rarely looking up to consider what’s changing around them until a crisis emerges.
Rodney: "The hard reality of being in especially a leadership role in any business is like every business decays. It just does. And the way that you know how it's going to decay is by paying attention to what's going on out there." ([06:26])

2. Sky as Both Threats and Opportunities

While most leaders instinctively notice threats (the dinosaur or meteor coming for your business), the sky is equally full of underexploited opportunities ([08:30]–[10:30]).
Human psychology and organizational habits tend to focus on pain avoidance vs. gain pursuit, often leaving innovation on the table.
Sam: "There’s this whole other side, the whole opportunity cost of things not done that are also in the sky. And you don’t know to pursue those if you’re not regularly engaging with it..." ([08:33])

3. Sky is Multilayered and Personal

Every function and role has its own unique "sky": the external forces shaping HR aren't the same as those shaping finance or product teams ([11:00]–[12:50]).
Healthy organizations encourage teams to track trends relevant to their unique context.

4. Sensemaking is Social, Not Solitary

Effective sky-scanning isn’t a solo act. Group sensemaking—coming together to share, debate, and synthesize external signals—is vital ([13:36]–[14:45]).
"Depth finding is a team sport," says Rodney. The interplay of individual curiosity and collective reflection distinguishes robust sky work.

5. Texture Over Checklists

It’s not just about tracking headlines or making trend lists. Successful leaders and teams develop "texture"—an intuition built from ongoing engagement and deep, diverse information ([14:37]–[15:28]).
Quick fixes or borrowed strategy frameworks often miss this richness.

6. Why Sky Work Often Fails

The "anti-example": Leadership teams express a desire to do strategic, sky-focused work, but lack rituals, rhythms, or space to actually engage in it ([20:43]–[24:00]).
Strategy development becomes performative: “By May, nobody can find the deck. And by, you know, September we're talking about next year's and with like no memory of what it was before." – Sam ([23:27])
Disconnect between declared aims and true external drivers leads to generic, unimpactful solutions.

7. Making Sky Work Part of the Rhythm

Carve out explicit time for sky work, e.g., Friday sessions to discuss external articles or trends ([27:44]–[28:13]).
Importantly, talk to people outside your organization to avoid echo chambers.

8. Individual and Collective Practices

There’s much individuals can do: reading, journaling, having prediction and review cycles, using AI tools to surface personalized trend analysis ([29:07]–[33:48]).
But collective synthesis—building a shared sense of threats and opportunities—is critical for real impact.

9. The “Ready” Example: Practicing What They Preach

The Ready has redesigned much of its own operating rhythm to integrate sky work, dedicating ~50% of its time on external sensing ([34:00]–[38:42]).
Rodney describes using scenario planning, red teaming, and engaging all members to collectively sense where their sector is going.
Adapting to dwindling client appetite for “ways of working” required them to shift toward helping on clearly sky-connected problems.

10. Creative, Imaginative Sky Work

Reading fiction (especially science fiction) can broaden leaders’ ability to imagine futures—a helpful practice for sky work ([18:03]–[19:23]).
Sam: "A leader who has a robust fiction reading habit…is likely to have a more sensitive and nuanced take on the sky..." ([18:03])

11. Don’t Rush into Execution

Resist the urge to immediately “action” every trend. Stew, experiment, and let clarity emerge ([41:19]–[44:41]).
Stew vs. omelette metaphor: "We want stew in this. We want to develop those flavors." – Sam ([43:42])

12. Impact at the Individual Level

Individuals who invest in sky work feel more confident and deliberate, even (especially) when making bold bets ([47:01]).

Notable Quotes & Memorable Moments

On decay and sky vigilance:
"Every business decays. It just does. And the way that you know how it's going to decay is by paying attention to what's going on out there..." – Rodney ([06:26])
On collective sensemaking:
"It is through the way that I talk about my interpretation of the sky and the way you talk about your interpretation of the sky that we actually create a new and better different take on what is actually happening..." – Sam ([12:50])
On performative strategy:
"February, we're all stoked about the new strategy. By May, nobody can find the deck. And by September, we're talking about next year's with no memory of what it was before." – Sam ([23:27])
On the necessity but rarity of 'sky work':
"...I just don't think that most leadership teams, in particular, make a lot of time for it." – Rodney ([14:37])
On individual sky practices:
"There's so much to be done as an individual where you don't need the buy-in of literally anybody else to really level up your ability to interact with the sky." – Sam ([29:07])
On stew versus omelette as a change metaphor:
"We're making a stew here, not making an omelette... Both are delicious, but only one is fast." – Sam & Rodney ([43:42])
On imaginative practices:
"Sky practices are imaginative in nature... you have to then imagine a future that may or may not exist." – Rodney ([19:23])
On the “magic” of shared sky work:
"When one of us posits a guess at what the play is, the rest of us go like, 'Yeah, that seems right.'...And that feels like magic. That feels like a magic trick." – Rodney ([46:57])

Timestamps for Important Segments

03:00–05:15: Introduction to the “sky” metaphor and why most orgs ignore it
06:26: Rodney on the inevitability of decay and the "paranoia" needed to avoid it
08:33: Sam on opportunity costs and the human tendency to notice threats
11:04–12:50: Multiple skies – Every function/team faces its own unique set of threats/opportunities
13:36–14:45: Why group sensemaking is superior to top-down sky analysis
18:03–19:23: The value of fiction and imagination in future-facing leadership
20:43–24:00: The “anti-example” where leadership wishes for strategy but refuses to build the practices
27:44–29:07: Practical tips for building sky work into the operating rhythm
34:00–38:42: How The Ready has institutionalized sky work internally
41:19–44:41: Letting sensemaking stew—don’t rush into execution
46:57: The magic of synchronized collective understanding
47:01: Confidence that comes from deliberate sky work

Practical Recommendations & Takeaways

Don’t rely on structure alone (e.g., OKRs, matrix reporting) for sky work—build explicit, recurring practices.
Balance the focus on opportunity and threat; don’t default to fear alone.
Encourage individual curiosity AND collective sensemaking; both are necessary for resilient strategy.
Read widely—including fiction—to build imagination muscles.
Make “external sensing” a rhythm, not a one-off; talk to outsiders, use liberating structures, and let new direction emerge organically.
Mix individual and organizational data sources—client feedback, team member insights, competitor moves, external advisors, publicly available information.
Give sky scenarios time to percolate rather than forcing instant plans and actions.

wavePod

Depthfinding: Sky - Threats and Opportunities

Summary

Episode Overview

Key Discussion Points and Insights

1. The "Sky" in Depthfinding: A Metaphor for the External Why

2. Sky as Both Threats and Opportunities

3. Sky is Multilayered and Personal

4. Sensemaking is Social, Not Solitary

5. Texture Over Checklists

6. Why Sky Work Often Fails

7. Making Sky Work Part of the Rhythm

8. Individual and Collective Practices

9. The “Ready” Example: Practicing What They Preach

10. Creative, Imaginative Sky Work

11. Don’t Rush into Execution

12. Impact at the Individual Level

Notable Quotes & Memorable Moments

Timestamps for Important Segments

Practical Recommendations & Takeaways

Transcript

Summary

Episode Overview

Key Discussion Points and Insights

1. The "Sky" in Depthfinding: A Metaphor for the External Why

2. Sky as Both Threats and Opportunities

3. Sky is Multilayered and Personal

4. Sensemaking is Social, Not Solitary

5. Texture Over Checklists

6. Why Sky Work Often Fails

7. Making Sky Work Part of the Rhythm

8. Individual and Collective Practices

9. The “Ready” Example: Practicing What They Preach

10. Creative, Imaginative Sky Work

11. Don’t Rush into Execution

12. Impact at the Individual Level

Notable Quotes & Memorable Moments

Timestamps for Important Segments

Practical Recommendations & Takeaways