I want to start by saying that the story you’re about to read, while featuring fictitious names, is based on a true experience. I was part of Alice’s team, living through all the trials, frustrations and hopes. I’ve since moved on and gained experience that gives me a new perspective on those times.

So, why share this story? Two reasons. First, reliving it through the lens of my current experience is a powerful form of reflection for me. Second, and perhaps more importantly, I hope that sharing these experiences can offer you the same opportunity for reflection and learning.

I invite you to walk in the shoes of Alice, a portfolio manager in the healthcare software industry, as she grapples with some of the most challenging decisions of her career.

Alice, the portfolio juggler 🤹

As the portfolio manager at MedSoft Innovation Solutions, Alice felt less like a strategic leader and more like a circus juggler — trying to keep all the balls in the air without letting any drop.

On one monitor of her computer, Alice had the plan to revolutionize HealthFlow (the flagship product) by integrating AI-driven diagnostic tools. On the other were looming deadlines for customer customization projects, which promised quicker and more certain revenue, and the ongoing maintenance work vital for existing client satisfaction.

Caught in this juggling act, Alice was facing the dilemma: innovate for the future growth or capitalize on the present?

If only I’d have enough data 🤔

Alone in her office, Alice felt the weight of her portfolio manager title. Her urgent needs - the innovative plans for HealthFlow, customization projects, and maintenance demanded resources she wasn’t sure she had.

Postponing customer projects would mean losing out on immediate, guaranteed revenue. Reducing maintenance could increase risks, potentially souring long-standing customer relationships. Delaying innovation was the easiest choice for short-term comfort, but it was a potential disaster in the long run, risking market share to quicker competitors.

“What’s the least damaging path?” Alice wondered. Her comfort zone urged her to play it safe — allocate fewer resources to innovation and focus on immediate needs. But a nagging voice warned her that taking this route might create a point of no return. Once lost, the momentum for innovation would be difficult, if not impossible, to regain.

Yet, she hesitated to make any hard decisions, afraid of what that might mean when facing her higher-ups. The fear of making a wrong choice paralyzed her. She knew she had to prioritize, but the thought of conveying the dilemma to the management filled her with dread. What if they questioned her competence or, worse, decided that if she couldn’t manage with what she had, maybe she wasn’t right for the job?

“If only I had more data,” she thought, clinging to the hope that some magical insight would emerge, allowing her to dodge the bullet of tough choices and managerial scrutiny.

Searching for a miracle 🦄

In search of an easy solution, Alice doubled down on data collection. “If we can get precise figures on how long each feature of the AI upgrade will take,” she reasoned, “perhaps a solution will reveal itself.” She directed her team to analyze granular aspects of time, cost, and scope for both the AI project and customer customization tasks.

Here you probably think: “It’s not very Agile of Alice. Everybody knows estimations bad!” But this is not about the estimations - Alice is facing a broader problem called analysis paralysis. The data she is collecting could be anything - work estimations, solution options analysis, interviewing customers - any data that she hopes to use to make the game of poker turn into the game of chess.

But Alice’s team delved into the details, the atmosphere grew tense. Conversations behind closed doors began to emerge. “Alice is hoping to find a miracle solution in the data,” muttered Mark, the senior developer. “She’s paralyzed by indecision and now wants to use data as a crutch. Or an excuse if things go south with management.”

Emily, the lead analyst, agreed. “The more we drill down, the more brittle this whole plan feels. We’re being set up to fail.”

The team’s collective morale dipped as they slogged through increasingly complicated data points. Each additional layer of information seemed to raise more questions than it answered. Frustration mounted, and whispers of Alice’s perceived indecisiveness became a regular topic of water cooler conversations.

Spiraling down 😭

Stuck in her indecision, Alice decided to play it safe. Instead of making any bold moves, she resorted to micromanaging her team, focusing on smaller, seemingly less risky decisions. Her avoidance of facing higher-ups with a concrete, bold plan turned her leadership increasingly inward.

As a result, the environment at MedSoft Innovation Solutions grew stifling. The most talented team members — those who had options — started to leave, seeking greener pastures. Among those who remained, a sense of resignation set in. MedSoft wasn’t the energetic, forward-thinking workplace it once was.

Meanwhile, a more agile competitor (let’s call them QuickHealth) started to erode MedSoft’s market share. The takeover wasn’t immediate or dramatic, which created a false sense of security within Alice and her higher-ups. Acquiring new customers started to become an uphill battle.

The new reality for MedSoft was one of stagnation and low morale. And the tragedy was that nobody could point to a single, disastrous decision that led them there. It was rather the absence of decision, the paralysis of indecision, that landed them in this quagmire.

Where did the story go wrong? 💡

The tragedy of Alice’s story isn’t rooted in a lack of intelligence or capability. It’s a human story, one filled with the fears and pressures that any portfolio manager in a complex industry could understand. Making big, risky decisions feels like putting your reputation on the line, especially when you’re dealing with incomplete or imprecise data.

However, Alice’s story teaches us that avoidance of risk and reliance on ever-more-precise data isn’t the solution. What could she have done differently?

• Rather than trying to make the impossible happen, Alice could have taken the hard data she already had and presented a case to her higher-ups about the resources needed for innovation, customer projects, and maintenance.

• The truth is, in complex environments like healthcare software, complete and precise data is often an illusion. Alice needed to accept the natural uncertainty of the business landscape and make informed yet decisive moves.

• Micromanagement was the nail in the coffin for team morale. Alice should have leveraged the skills and insights of her team, entrusting them with responsibilities that would make the entire project move more efficiently.

• Once a course was chosen, it would be essential to continually reassess and adjust. This way, if Alice found that innovation was not yielding the expected results, there would still be room to pivot.

Facing management with hard truths isn’t easy. Neither is taking the leap of faith required to make big decisions with imperfect data. But the alternative, as Alice learned too late, is far worse. It leads to a culture of stagnation, lost opportunities, and disengagement.