The Waiting Game: Finding the Right Moment to Decide

decade back, I met this girl named Sana. We hit it off right away. Things were going great. But a few months in, Sana's like, "So, what's the deal? Are we going somewhere with this? I'm at a point in my life where I'm ready to settle down, get married." But me? I hadn't really thought about it.

Getting married is one of those life changing irreversible decisions? It's not like choosing which apartment to rent. This is more like deciding to move to a new country or putting down payment on a property. It's one of those irreversible decisions, and the stakes are high. This a decision that lies in the fourth quadrant of our decision matrix. I mean, if it goes wrong, it's not just your bank account that gets steam rolled. The psychological and emotional cost is bound to knock you down.

Besides, with a family history of rocky relationships, I was hesitant to jump in. I wanted to make a smart call, avoid past mistakes, and ensure this was the right fit for the long haul. But I didn't have a crystal ball. I couldn't just peek into the future and see how it would all turn out.

As I'm stuck wondering, how long can I wait? What else do I need to know before I take the plunge? I really cared about Sana, but was I ready for forever? And what if, while I'm busy soul-searching and gathering intel, she decides she's done waiting around for me to make up my mind? Do I risk losing her altogether?

It's a tough spot to be in. You've got to weigh your feelings and your future. You want to get it right, but you're not 100% sure what "right" is. And you can't take forever to choose.

The pressure to make the right call isn't limited to our personal life. At work, I wrote about a similar challenge in implementation of an enterprise reporting system . We had poured months of effort into customizing and deploying this solution, only to discover later that it wasn't the optimal fit for the organization's needs. Deciding whether to pull the plug and start over or persevere based on the time and resources already invested, was a constant struggle. It felt wasteful to abandon something we'd worked so hard on, but clinging to a sinking ship wouldn't be any better. This experience highlights the difficulty of navigating high-stakes, career altering decisions where information is constantly evolving and the outcome hinges on our ability to distinguish between valuable insights and sunk costs.

This is the nature of these big, life-changing choices. The more irreversible and consequential a decision is, the more we want to wait and gather information until the last possible moment before making a decision. Bad decisions often result from information we wish we knew at the time of the decision, so it makes sense that we'd want to wait and gather as much information as possible.

However, if we act too soon on the information we gather, we risk missing out on vital information that could change our decision. On the other hand, if we act too late, we miss out on opportunities.

ASAP vs ALAP

On a continuum, we have decisions that are to be made as soon as possible (ASAP) and those which are to be made as late as possible (ALAP). As we delay the decision, we gather information that could improve the quality of our decision. We can plot the utility or usefulness of the information being gathered on the Y-axis.

Most decisions in our life, be it work or family, are reversible and the cost of the decision going wrong isn't high, these are low-stakes decisions. Hence, these should be made as soon as possible.

When decisions are easily reversible or inconsequential, moving slowly and letting them linger and occupy mental space is the biggest risk. If we can take something back or it doesn't really matter, gathering too much information becomes a drain on resources. We should save our time, energy, and mental space for the choices that really matter. After all, we wouldn't want to miss out on a once-in-a-lifetime opportunity because we were too busy deciding what to have for lunch.

Delegating low-stakes, reversible decisions to others, whether it's our kids at home or our team members at work, is like giving them a chance to exercise their decision-making muscles. As they practice, they grow more confident and motivated, feeling a sense of ownership over their choices.

On the other hand, micromanaging these small decisions is like telling them we don't trust their judgment. It's demotivating and can lead to a culture of frustration and apathy.

When faced with an irreversible and consequential decision, like whether to commit to a relationship or accept a new position at work, gather as much information as possible before deciding. The biggest risk is moving too fast and missing crucial details. When the stakes are high, decide as late as possible while keeping your options open and continuing to learn. But how do you know when it's time to act and make that leap of faith?

Diminishing marginal utility on information gathering

Anyone who has held onto a job, relationship, or investment for too long knows that there comes a point when the returns on information gathering start to diminish.

We find ourselves rehashing the same arguments, reviewing the same data points, or trying to fix the same problems over and over. It's like being stuck in a hamster wheel, expending energy but getting nowhere. In these moments, we're not gaining new insights; we're just spinning our wheels.

So, how do we break free from this cycle of diminishing returns? How do we know when it's time to stop analyzing and start acting? The next lesson in Decision by Design framework offers the Stop, Flop, and Know framework:

• STOP gathering useful information.
• When you First Lose and Opportunity (FLOP)
• Or when you KNOW you have gathered a critical piece of information.

We can visualize this framework as a set of traffic lights, guiding us towards the moment of decision. It helps us recognize when we've reached the point of information saturation when further analysis is more likely to lead to paralysis than progress.

By attuning ourselves to these signals, we can break free from the endless cycle of deliberation and move forward with confidence, knowing that we've done our due diligence and are ready to make the call.

Consider a scenario where an extremely risk-averse leader in a company consistently waits too long to make even the smallest decisions. They constantly request their team to prepare endless analysis and memos, even for trivial matters. They struggle to recognize when to stop, to the point that when the reports are eventually released, they've lost their relevance.

This approach not only frustrates the team but also diminishes the department's image within the organization. Management begins to view the department as a back-office function, merely crunching numbers, because the information provided is often outdated and irrelevant.

If this situation sounds familiar, the three signals of Stop, Flop, or Know can be incredibly helpful in determining when it's time to stop deliberating and start acting.

STOP

First, recognize when you've stopped gathering useful information. More isn't always better. Beyond a certain point, additional information only confirms our biases, while costing time and resources.

As we invest effort, we tend to dismiss conflicting information and embrace confirming data, reinforcing our original conclusions.

Watch for these signs that you've reached the limit:

• Frantically googling for more data
• Seeking advice from less relevant sources
• Rehashing the same information or arguments

When you hit these points, you've likely gathered all the useful information available. It's time to decide. That's "Stop" – you've stopped gathering valuable insights.

FLOP

Now, let's discuss "FLOP" – your "First Lost Opportunity." When facing an irreversible, consequential decision, and your aim is to hold out as long as possible, the signal to decide is when you start losing opportunities.

The goal of waiting is to preserve options. When options start to diminish, it's time to act. Like selling a house – you can list it, price it, and field offers, but if buyers start walking away or you're about to breach a contract, you're losing options. Act now.

When at FLOP, distinguish between perceived and actual lost opportunities. As Robert Cialdini notes in "Influence," people often try to influence us by employing scarcity tactics to pressure decisions and commitments. These tactics artificially create a sense of diminishing options, urging us to act prematurely.

KNOW

Finally, when you “know”. Sometimes it’s a critical piece of information you’ve gathered that confirms your decision. Sometimes in more ambiguous situations like relationships, it’s a gut feeling that doesn’t go away or change. When you know what you’re going to do — it’s time to put the gears in motion.

Again, you don’t have to announce it. You don’t even have to do the main act yet (firing someone, quitting your job, buying the house). But if you know, it’s time to act on the information you have and move from deliberating to putting it in action.

As I reflect on the choices I have made, particularly those with long lasting, life changing implications, I realize that the key to effective choices lies in finding the sweet spot between information gathering and decisive action. It's about having the courage to commit fully once you've reached the point of "Stop, Flop, or Know," trusting in the knowledge you've acquired and the instincts you've honed.

Looking back, I can see how my own approach to decisions has evolved. I've learned to recognize when I'm repeating myself or chasing down irrelevant information, to act swiftly when opportunities are slipping away, and to trust my gut when a piece of information fundamentally changes the equation.

In the end, effective decision-making is not about perfection; it's about having the courage to move forward, even in the face of uncertainty. It's about learning from our choices, both good and bad, and using that knowledge to grow and evolve.