Who should win: Jill or Jack

If you are not working alone, then you are in a relationship.

And they are everywhere. Projects. Joint ventures. Companies. Partnerships. Teams. Relationships come in all shapes and sizes.

Take Jill and Jack.

Their business partnership began at the bottom of a hill.

Jill: It looks like a steep climb.

Jack: But, at the top of that hill is a deep well, containing the promise of water.

With the right tools (rope, bucket, shareholder agreements) in place, they begin their quest.

At first, the going is good. But, midway up, the going gets hard. So they support one another and re-commit to the task. They take risks. Delegate. Pay too much for a tech stack. Ultimately, they share responsibilities based upon their unique skills and abilities.

But calamity strikes!

Close to the summit, there’s a slip, then a fall. Crowns are broken (ooff, @#!$#*, ouch).

Later, armed with new policies, professional development, risk management oversight, and beefed up insurance coverage, they try again.

Victory. Finally, they make it to the well (stakeholders cheer!) They lower the bucket. Slowly they pull it to the surface. Only to find it’s barely half full. Given their effort, perseverance, and investment, they don’t feel it’s near enough water in return.

For a while, they are dejected. Then, during a process review to uncover lessons learned, resentments emerge.

Jill: if it weren’t for me, we never would have found the hill in the first place.

Jack: But, without my bucket…

Suddenly, out of the corner of her eye, Jill spies a new, more beautiful, hill (small mountain, really). And at its top: a deep, untouched, azure lake.

Jill: (gasps) Could we? Should we?

Jack: I have many more buckets! But…Jill, if I’m honest, I’m so tired. And, you know I’d still like to go climb a beanstalk—that’s always been my passion, my purpose.

Jill: Then how much do you want for your buckets? I’ll go it alone!

Jack: But (single tear) we’re a…we’re a team.

Jill: Are we, Jack? Maybe that’s in the past? Maybe we should just walk away from this whole hill and water business?

Jack: Wait. Before we set off again, or walk away completely, are we sure we really tried hard enough right here? We know this old hill. Let’s lower the bucket down again a few more times. We totally own this well! Are we really going to walk away from all this?

So, what should they do?

Call it quits and just both walk away?

Ought Jack sell Jill his buckets and go climb beanstalks? Should they double down on their existing hill and well?

Or, is this simply a setback-along-the-way that they need to overcome, by using everything they’ve learned together to venture forth on a new, more ambitious, quest to the lake-on-the-mountain?

Ages and Stages

All relationships evolve. We start with good intentions, and obstacles are overcome, trust, hope, and ambition builds. Our needs overlap; our interests become enmeshed.

But the going, inevitably, gets hard.

And when it does, knowing what to do is complicated.

In my coaching practice, the biggest pitfall I see is when relationships get stuck.

Needs change, but old habits and rigid obligations prevent renewal and growth. Letting go and moving on can seem like a kind of failure or loss. Generosity and space can seem like weakness.

So, positions become entrenched, and teams, partnerships, joint ventures, and businesses become stuck.

Once this happens, out of sheer self-interest, pain, and hurt, we wound one another—the very people we once held in such high regard and bestowed with all our faith and trust.

So my coaching questions for you this month:

Where can you be more generous in your most important relationships?

Where are you over-committed to being “right” at all costs?

Remember, sometimes we are Jill. Sometimes we are Jack.

(Still other times, we work for them while they tumble down the hill despite themselves.)

So, be you Jill or be you Jack, be sure to check in with one another often. Locate where you are at, and communicate how and where your own needs may be changing. As important, stay curious and honest about how well you are meeting your partner’s and teammates’ evolving needs too.