Are We Aligned with Everyone Around Us?

Are we really aligned with everyone around us — our employees, Co-Founders, or even our spouses?

After 30+ years of working my ass off to find "synergy" with these three groups, I learned a painful lesson — try as I have, I'm not fully aligned with the people in my life.

I want to be. They are all awesome people. But I've come to realize that there are some important nuances that prevent Founders from ever being 100% on the same side of the table as the people around us.

This has been a source of endless frustration for me, and certainly for those around me. Over time, I've come to acknowledge and support the differences. But first, I had to figure out what the hell was so broken!

Employees

The subtlety of alignment with employees isn't just the fact that "We are the boss and they are employees" — that part is easy. It's the fact that we go down with the ship — and they don't. Our level of consequence is geometrically higher than theirs, which prevents us from being aligned.

Not sure about that? Try running out of money and see who still shows up for work. Try getting sued and see if they are named on the suit. Try telling your investors you got a better job and see how well that goes over. It ain't the same.

We can't fake this. Even though we want to be as aligned with our team as possible, we simply have a level of conviction they don't. Instead, we've got to reframe every interaction with the caveat "I'm committed to this in a way you aren't, so my expectations should be based on your commitment, not mine."

Damn, that would have been useful information to tell 30-yearso-ago-me.

Co-Founders

If we can't perfectly align with our employees, you'd at least think we can readily align with our Co-Founders. At the very least, we have a similar job with similar consequences. Our success or failure directly mirrors theirs. So what's the problem?

The problem is that our expectations don't always align. Whether it's the fact that we don't think our Co-Founders are pulling their weight or we're pissed about how the equity is split, the alignment is always a challenge.

Even with a 50/50 split and equal time invested, we still have the issue of where the company should go. Should we grind it out in bootstrap mode by racking up more debt, or pull the trigger and get on the VC fundraising train? Everyone has a different set of goals and personal situations, so that alignment becomes harder and harder over time.

Spouses

One of the areas of consternation that few people talk about is how our startup goals align with those of our spouses. They usually don't in my experience. This isn't about the relationship per se; it's about how our goals rarely support that relationship.

What we bring to the table is a tremendous amount of uncertainty and fear. None of that translates really well to "If you want to make your marriage work better, start a startup!" (Seriously, if you want to fast-track a divorce, maybe start a startup!)

Our big vision and identity may be tied to this thing — but our spouses are not. In some cases our goals may be entirely at odds. My wife treasures security and safety above all else. How she sought that out in a husband who has only done startups for 30+ years is beyond me!

But if I try to lean on my goals without recognizing how much they don't align with hers, I'm begging for conflict. So I always start with "I know these are my goals, and not necessarily yours, so this is why this is important to me." 60% of the time, it works every time.

Can't We All Just Get Along?

We sort of can. In my experience, as I've become more self-aware of how my goals and needs differ from those around me, I've stopped "forcing alignment." It's not always easy, but at least now I realize when I try to force-feed alignment, it's going to break.

I used to think alignment was a prerequisite for building something great together. Now I realize it's more like a luxury. It's rare, fleeting, and almost never perfect. But what is required is empathy. The ability to understand where someone else is coming from, even if we’re headed in slightly different directions.

That’s what I’m trying to practice now. Not forcing everyone to share my goals, but respecting theirs enough to keep showing up together.

In Case You Missed It

Should Startups be a Family? Running a startup isn't a group hug. Keep the vibes real but the roles clear. Authority fades fast when everyone's
"family."

Why I'm Either Working or Feeling Guilty How can we achieve a harmonious equilibrium that allows us to pursue our entrepreneurial dreams while also nurturing our mental and physical health and maintaining meaningful relationships?

Will the Payout be Worth the Sacrifice? An honest look at the allure of success and the even deeper question: is the payoff truly what you want?