Your Only Real Job

My job is pretty simple.

Find the obstacle. Remove the obstacle.

That’s it. My job description and operating philosophy. All packed into six words.

When I’m called in to help a portfolio company, I don’t start with the financials or their sales and marketing performance. Sure, that’s part of the process. But it’s not where I start.

I start by looking for the biggest thing standing between us and the company we want to become. I start by looking for the obstacle.

Sometimes the obstacle is obvious. It’s a broken process, an outdated product, or a change we’ve been talking about for months but still haven’t executed.

But most of the time, it’s not that easy. Most of the time, the obstacle is more subtle than that. It’s a mindset, a relationship, or a blind spot the team can’t—or won’t let themselves—see. These hard-to-spot obstacles come in all shapes and sizes.

• Our product works fine, but we’re confusing people with our pitch.
• Our team won’t get real with each other (even though our numbers are down).
• We’re looking at too many metrics and need to simplify our scorecard.
• We’re stuck in a fire drill fix-it loop and aren’t looking at our data at all.
• We’re guessing what our customers want when we should ask them instead.
• We’re chasing a “transformation” when we should be stacking up small wins.

And those are the easy ones.

Sometimes, the obstacles are more uncomfortable.

• Maybe we’re not selling more because our sales leader is the wrong fit.
• Our marketing strategy is fine, but our writing is boring and unclear.
• Our problem is staring us in the face—pipeline, win-rates, or retention—but we’re trying to fix all three of them at once.
• Or maybe we’re just making our product too hard to buy.

Take a good look at those ten bullets. That’s a good list. And there’s a very good chance that no matter what your business does or what you’re dealing with, your #1 obstacle is in there somewhere.

That’s the first step: Identifying the obstacle. But just identifying it isn’t enough. Identifying it doesn’t mean you’ve acknowledged it. And acknowledging it doesn’t mean you’ve accepted it.

Acceptance means owning it. It means looking your obstacle dead in the eye and admitting, “Yes, this is the thing that’s holding us back. The thing I have helped to create. The thing I’ve been avoiding. The necessary thing that I’ve been putting off.”

Until you get that intimate with your obstacle, you can’t deal with it.

Because you can’t fix what you’re not willing to focus on.

So when you find it, don’t hide from your obstacle.

See it for what it is.

Face it. Name it. Own it.

And then remove it.

That is the job.

The only real job.

Mine. And yours.

I'm Paul. I'm an Operating Partner for a private equity fund in Chicago. And this is the kind of stuff I write about over at my blog, Hello Operator.

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