Five Strategy Questions to Ask Today


Love And Leadership: How To Make A Great Marriage Decision

By February 15, 2017 No Comments

It seems like everyone I know is currently considering some major life change.

A new job, role, graduate program, relationship, city…

The fact that so many people are contemplating change doesn’t surprise me. What does surprise me however, is how poorly, slowly and inefficiently we execute.

What surprises me is how bad we are at making big decisions with confidence and speed.

Of course, most of us don’t see this as inefficient, we see it as diligent: making big decisions takes time, right?

Not exactly.

How to make a good decision with speed and confidence

Whether you are contemplating a major business change, or major life change, if you want to improve both the quality and speed of your decision, you need the following three things:

  1. Objective data
  2. A plan, with deadlines
  3. The courage to act

Sure, sometimes the “plan” takes time, but more often than not, “more time” is an excuse for those who lack one or more of the four parts above.

Let’s apply this to something truly important: the decision to get married.

Of all of the major life decisions that we make, few are as important as whom we marry.

And yet, despite it’s importance, I’ve observed that even the most-talented leaders approach the marriage decision in a way that is far less rigorous and disciplined than what they would ever use when making a business/strategy decision.

Take, for example, my friend who would often describe his long-time girlfriend as being: “95% perfect.”

According to him she was smart, kind, comes from a “nice family,” and loved the outdoors, among other positives.

But, when I asked why he hadn’t yet proposed, it wasn’t the 95% that he focused on – it was what I call the “final 5%” — the handful of characteristics that didn’t quite fit his vision of the woman he was supposed to marry.

When I asked him how he planned to ultimately make his decision, he shrugged his shoulders.

This continued for over a year until his girlfriend, frustrated by his inability to commit, broke the relationship off (making the decision for him).

For better or worse, there’s always a “5%”.

The “5%” could best be described as two questions playing, on repeat, in our minds:

  • How will, or won’t, this person change over time?
  • What will be the implications of that change on my personal happiness and well-being?

These are the right question to be asking. That said, without the right data and plan, it will be hard for you to act with confidence.

So, in the spirit of learning how to better lead, when it comes to love, here are a few ideas to get you started:


1. Gather Data (Personal Core Values + Personality)

Without question, the most important piece of data that you and your future partner must have is an understanding of your personal core values.

Your core values are the principles that you personally prioritize. There is not “right” or “wrong” when it comes to values — there’s just “true.”

Your values have been shaped and influence by the life you have lived, to-date; by your parents, your friends, your experiences.

While there may be no right or wrong, the level of alignment between your values, and those of your future partner, will dramatically influence the quality of your relationship and the ease with which you jointly make decisions going forward.

Discover your core values together and determine if and how these values make you stronger as a couple and where they will make a long-term commitment more challenging.

The “Big Five” Personality Traits

A simple proxy for personal core values are the “Big Five” Personality Traits:

  • Openness
  • Conscientiousness
  • Extraversion
  • Agreeableness
  • Neuroticism

In her book The Defining Decade Dr. Meg Jay suggests using the “Big 5” as a litmus test to determine the likelihood that your relationship can endure over time.


According to Jay, The Big 5 “is not about what you like — it’s about who you are and how you live…it’s how you experience the world and, as a result, how others experience you.”

Jay recommends that you and your partner score yourself; determine where each of you fall on the spectrum (high, medium, low) for each of the Big Five traits.

These scores, says Jay, “will bring into relief how similar — or dissimilar — your personalities are. There is no right or wrong…but it is often the case that we like or dislike people because of the way their [scores] compare to our own.”

2. Create A Plan

I often joke that the real first step in the decision-making process is to “decide to decide.” In other words, commit to making a decision — “yes” or “no” — in a defined time frame.

With data in hand, it’s time to make a decision.

Here’s a simple plan:

Step 1: Set A Deadline

More than a week, but less than a month. If it takes you longer than that, you’re procrastinating…hold yourself accountable to a real deadline. This is fair to the other party involved – but it’s also better for you too; it only gets harder the longer you wait.

Step 2: Get Aligned

This is where you business leadership skills help. Sit down with your partner and start asking the kind of questions that matter when it comes to the long-term success of this partnership.

Among the questions that might be discussed:

  • What does “success” look like?
  • What “matters most” when it comes to this relationship?
  • What will we do if/when work gets in the way of “us”?
  • Do we want kids? If so, what kind of life do we want to create for them?
  • What are your expectations around money? Quality of life?
  • Among others…

Note: The answers to all of these questions should further validate/illuminate the data discovered in your core values / Big Five assessment.

Step 3: Pressure-Test Your Thinking

Too often we keep this stuff internal – and our minds tend to wander and loop as we evaluate the pros and cons.

Use a friend, a coach or other trusted advisor to serve as a sounding board – pressure testing your assumptions and decision-making process.

Sarah and I used a variety of resources from our priest, to a marriage counselor/therapist to help us work through some critical misalignments.

3. Take Action

Make the decision. Yes or no. Regardless of your answer, it will be the first day of the rest of your life. Congratulations.

Even better than having made this huge decision, is that it gets easier…

(Marriage? No, not necessarily… 🙂 )

But, making big decision does!

The decision whom to marry is likely the biggest you’ll make in your life.

The good news: with every big choice you make, the subsequent decision-making process gets easier.

You won’t always get them right, but as long as you are thoughtful throughout the process, you can look back on the decision made without regret.

Ben Sands

Author Ben Sands

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