"Let's wait until the market settles. Let's wait until budgets are healthier. Let's wait until we know more." Penelope Drift — Senior Vice President and Chief Information Officer at Verity Wellworks and founder of the leadership practice Threshold Leadership — has heard every version of that sentence, and thinks the framing is backwards. Innovation isn't a reward organizations earn once things feel stable. It's the capability that lets them survive when things aren't.
Penelope set out for a career in hospitality before IT captured her, and she's spent the years since in mega-resorts and then healthcare systems watching what happens to teams that postpone adaptability. Tune into episode 5 of The Focal Point to hear why she believes the safest-looking decision is often the one that makes an organization more fragile — and how she funds learning before it becomes unaffordable.
Episode Video
About the Guest
Penelope Drift is a healthcare and technology executive who builds adaptive capability inside large, risk-averse organizations. She is known for treating innovation as an operating discipline rather than a discretionary spend — running small, continuous, deliberately funded experiments during good quarters precisely so the organization knows how to learn during bad ones.
She began her career in hospitality operations at the Sablewood Resorts group, moved into resort systems technology, and then into healthcare, where she led digital transformation for the Ellingsworth Care Network before joining Verity Wellworks. She is also the founder of Threshold Leadership, a practice teaching service-industry hospitality principles to technology leaders.
Penelope holds a B.S. in hospitality administration from Brightmoor University, a Master's in Business from the Calloway Institute, and a certification in healthcare administration. She currently serves as SVP & CIO for Verity Wellworks.
Transcript
Invest before certainty
[Music] >> This is the Focal Point Podcast. An ongoing series where we deep dive into the meat of messy management. Whether it's technology, [Music] business, government, or entertainment, we chat about our experiences and perspectives in life [Music] and leadership. Join us as we learn about their latest insights and hopefully inspire you to have some of your own. >> [Music] >> Here's the scary part. The safest looking decision may be the one that makes the organization more fragile. >> That's a good opening because most leaders think they're being responsible when they say, "Let's wait until the market settles down. Let's wait until budgets are healthier. Let's wait until we know more." >> Right, it sounds prudent. >> It sounds mature. >> But the article we're unpacking today argues that this framing is backwards.
Innovation is not something organizations earn the right to do after everything feels stable. Innovation is how organizations build the capability to survive when things are not stable. >> Exactly. This looks like discipline right up until it collapses. >> And the collapse usually does not happen all at once. That's the important part. It happens because the organization kept postponing the work that would have made it more adaptable. >> So by the time leaders finally say, "Okay, now we need to innovate," they're trying to learn at the most expensive possible moment. >> Yes, the cost of learning is higher, the tolerance for failure is lower, the options have narrowed. Everyone wants certainty, but the whole point is that certainty is no longer available. >> So, this is not really an innovation problem. >> Not only.
It's a resilience problem. The article calls it the resilience investment problem. Leaders wait for conditions to feel safe before funding the work that would make the organization safer. >> That's the part leaders usually miss. >> Exactly. It's like refusing to repair the wiring in a building until you smell smoke. The smoke detector is useful, but if that is the first time you care about the electrical system, >> [Music] >> you are already late. >> Right, because the dashboard only shows the smoke, not the wiring inside the walls. >> That's the argument. Innovation investment is the wiring work. It is capability, learning, optionality, and resilience before the crisis makes them urgent. >> Let's start with the first section. Certainty is not the price of admission.
>> This is where the article takes aim at a very common leadership instinct. Leaders want innovation, but they want [Music] it with guarantees. They want the new product with validated demand, the new platform with no migration risk, the new operating model with complete buy-in, the new service line with a clear return before the first real experiment. >> Which is understandable. >> Completely. No one wants to waste money. No one wants to sponsor a failure, but the article makes a sharp distinction. Requiring certainty before investing does not remove risk. It often just moves the risk into the future. >> Wait, say more about that. >> If you do not run the experiment now because it might fail, you have not eliminated the possibility of failure. You have delayed the learning.
Avoid innovation theater
And when the organization eventually needs that capability, the failure will happen under more pressure, with less time, and with more people watching. >> So, the organization is not avoiding [Music] exposure. It's choosing worse exposure later. >> Exactly. Innovation always involves exposure. The question is whether failure can be made informative while it is still small. >> That's a useful distinction. Failure as information versus failure as catastrophe. >> Yes. And the article pushes leaders to fund learning, not just launches. Experiments, not just programs. Capability, not just announcements. >> That line matters because a lot of organizations say they're funding innovation, but what they really fund is performance theater. >> Yes.
A polished road map, a steering committee, >> [Music] >> a press release, a transformation name, maybe a prototype. >> But not the real learning loop. >> Exactly. And if failure is not allowed, then discovery is not real. The work becomes execution dressed up as innovation. >> So, if a leader says, "We support innovation, but this cannot fail." What they're really saying is, "We support pretending." >> That's blunt, but yes. Because any meaningful innovation involves contact with unknowns. >> Which leads into the second idea. Some lessons cannot be outsourced. >> This section is important because it challenges another comforting behavior. Organizations want the benefits of experience without actually experiencing the hard parts. So, they buy research. They hire advisers. They study competitors. They benchmark. They read reports.
>> And those things are not bad. >> Not at all. The article is careful about that. External inputs can help, but they cannot replace the internal knowledge created by doing difficult work. >> This is like trying to learn how cold the water is by reading a report about swimming. >> Exactly. At some point, someone has to get in the pool. >> Or maybe more accurately, the organization has to learn what swimming feels like with its own people, its own constraints, its own legacy systems, its own customers, its own politics. >> [Music] >> Yes, that's the texture of the work.
You can understand the concept of platform migration from the outside, but you do not really understand your organization's migration risk until you encounter the dependencies, the undocumented workflows, the customer edge cases, the operational habits, and the internal resistance. >> Same with product market risk. >> Right. You can read all the market research you want, but eventually you have to put something in front of customers and learn what they actually do. >> And waiting delays that understanding. >> That is the key. The organization that delays experimentation also delays understanding. Then, when conditions tighten, it has less time to absorb lessons it avoided earlier. >> This reminds me of a flight simulator versus flying through a storm.
Build the learning flywheel
The simulator helps, training helps, but you don't want your first real lesson in turbulence to happen when the engine is already failing. >> That's a strong analogy, and it gets at resilience. Resilience is not built by reading about pressure. It is built by developing the capacity to move through pressure. >> Which brings us to the third section. Daily investment beats dramatic rescue. >> This may be the most practical part of the article. It argues that resilience is usually not built through one heroic initiative. It is built through repeated investments in capability. >> Better tooling. >> Cleaner architecture. >> Stronger discovery. >> Clearer ownership. >> More reliable data. >> Healthier feedback loops. >> And teams that know how to learn together. >> Exactly.
None of those sound as exciting as a dramatic innovation bet, but they are often what make the dramatic [Music] breakthrough possible. >> So, leaders should be suspicious of strategies that depend on one big rescue move. >> Yes, because the big rescue move [Music] is often a signal that the small investments were neglected. >> It's like health. People want the emergency surgery, the miracle intervention, the dramatic turnaround, but most resilience comes from daily habits. >> Right. The article makes that same connection. Breakthroughs show up late. The practices that make them possible are built quietly beforeh. >> That's hard for organizations because quiet capability building is not always easy to celebrate. >> And it's not always easy to measure immediately. >> A cleaner architecture doesn't always produce a headline this quarter.
>> But it may make the next product cheaper to build. It may make the next integration less painful. It may reduce the cost of change. [Music] It may create room to maneuver. >> And that phrase, room to maneuver, feels central. >> It is. Resilient means the organization has options. It can change direction without breaking. It can absorb surprise without freezing. It can learn without panic. >> So, the leadership question is not, "What giant innovation initiative are we announcing?" It is, "What are we practicing every week?" >> Yes. [Music] What capability is being compounded? What small experiment is teaching the next decision? What system is becoming easier to change? >> That word, compounding, takes us right into the next section. Momentum is built before it is needed. >> The article uses the flywheel idea here.
The most resilient organizations build a flywheel of learning and delivery early, so later pressure has something to work with. >> And you cannot summon momentum on dem. >> Exactly. [Music] This is one of the great leadership fantasies, that when the crisis arrives, the organization will suddenly become faster, braver, more aligned, and more creative. >> But, pressure does not create capability. It reveals capability. >> Yes, pressure reveals what has been practiced. >> That's worth repeating. Pressure reveals what has been practiced. >> And stop-start innovation programs are so damaging because they interrupt the compounding. Every time the program starts over, the flywheel starts, >> [Music] >> teams lose context, sponsors change, the lessons dissipate, confidence resets. >> This is where the drumbeat analogy helps.
A marching group does not stay coordinated because someone yells march faster when they reach rough terrain. They stay coordinated because there has been a drumbeat all along. >> Exactly. The rhythm has to exist before the pressure. Innovation needs that rhythm, too. >> Regular experiments, regular learning reviews, regular customer contact, regular technical improvement, regular decision-making. >> And [Music] continuity. The article is not arguing for endless spending with no discipline. It is arguing that resilience requires continuity long enough for effort to compound. >> That's where many organizations sabotage themselves. They say innovation matters, then fund it episodically. >> A quarter here, a pilot there, a lab that disappears after a reorg, a platform initiative that pauses every budget cycle.
Fund capability that compounds
>> And then, they wonder why nothing compounds. >> [Music] >> Right. You cannot keep stopping the flywheel and then blame it for not spinning. >> Okay. Then, the article turns to a more subtle idea. Build what outlives the forecast. >> This section is about future optionality. Not every useful investment produces immediate proof. Some work creates conditions that matter later. >> Like a stronger data foundation. >> Or a cleaner platform. >> Or a better operating model. >> Or a team with deeper domain understanding. >> The return may be real before it is easy to measure. >> Exactly. And that creates tension for leaders, especially in organizations that demand near-term proof for everything. >> Because some investments look uncertain precisely because their value shows up after the current planning horizon.
>> Yes, the article uses the image of building a cathedral. You add bricks to something whose full value may not be visible yet. >> I like that, but it can also be dangerous. >> Say more. >> Because building a cathedral can become an excuse for vague spending. Any unclear initiative can hide behind patience. >> Exactly. And the article addresses that. Patience does not excuse blur. Resilience investments should be patient, [Music] but they should not be blurry. >> That's a useful distinction. >> Leaders still need a thesis. What future capability are we building? What options will it create? What constraints will it remove? What learning will it make possible? >> So the question is [Music] not, can we prove the ROI immediately? The question is, can we explain the capability clearly enough that the patience is disciplined?
>> Yes, and that is a higher bar than vague optimism. >> It requires leaders to name what they are really buying. >> Exactly. Not just software, not just a team, not just a platform. They are buying future adaptability. They are buying lower cost of learning. They are buying options. >> And options matter most when forecasts fail. >> That's the whole point. If the future were perfectly predictable, innovation would be less important. But uncertainty is exactly why learning has value. >> Which brings us to the final question of the article. What are you waiting to learn? >> This is where the article turns from diagnosis to leadership reflection. It asks leaders to examine the work they keep postponing until conditions improve. >> Which capability will be harder to build later?
>> [Music] >> Which experiment is being delayed because the answer might be inconvenient? >> Which platform, process, or product bet would create options the organization may soon need? >> And underneath all of those is a more uncomfortable question. >> [Music] >> Are we calling our delay prudence because we do not want to encounter what the experiment will reveal? >> That's the part leaders usually miss. Sometimes waiting feels strategic, but it is actually avoidance with a business case attached. >> Yes, and the cost of avoidance compounds. If you avoid the learning now, you may still have to learn later, but with less time, less trust, less margin, and more urgency. >> So, how should leaders use this? >> I think there are a few practical questions to take into a leadership meeting. >> [Music] >> Let's make these concrete.
Questions for disciplined resilience
>> First, what are we postponing because we want certainty that this work can never provide? >> Good. Second, where are we mistaking reports, benchmarks, or advisor input for actual organizational learning? >> Third, what small experiments could make failure informative while it is still small? >> Fourth, what capability are we building every week, not just announcing once a year? >> Fifth, where have we interrupted the flywheel? Where did we stop and restart so many times that learning never had a chance to compound? >> And sixth, what are we building that will outlive the current forecast? >> Yes, but with the follow-up, can we state the thesis clearly? What options does it create? What constraints does it remove? What learning does it make possible? >> Because the goal is not reckless innovation. >> [Music] >> No, that's important.
This is not an argument for spending casually or chasing novelty. >> It is an argument for disciplined learning before the organization is desperate. >> Exactly. Innovation is not decoration for success. It is not a luxury reserved for calm periods. It is how organizations create room to maneuver. >> And maybe that is the closing image. The organization waiting for certainty thinks it's staying safe, but really it's standing still while the exits narrow. >> Yes, by the time the dashboard turns red, the real failure may have already happened. The wiring has been neglected. The flywheel has stopped. The team has not practiced learning under uncertainty. >> And then leaders ask for innovation at the exact moment when innovation is hardest. >> The resilient organization does something different. It invests before the need is obvious.
It learns before the crisis is loud. >> [Music] >> It builds capability before the forecast breaks. >> So, the final question is not, are we certain enough to begin? >> It is, what will become more expensive to learn if we keep waiting? >> Because certainty is not the starting line. >> Capability is. >> And the organizations that understand that don't wait to become certain. >> They invest early enough to become ready. >> Thank you for tuning in to this episode of >> [Music] >> The Focal Point. Be sure to subscribe on your favorite platform. >> [Music] >> I'm your host, Filiberto De La Cruz. >> [Music] >> Until next time. God bless you and yours and everyone. >> [Music] [Music] [Music] >> Woo!
