Opportunistic vs. Deliberate

Earlier in my career, I lived in the constant push-pull between Product and Sales. Sales always wants things faster—they want new toys and fully customized versions of the product before the current one is even out of the box. By the time you build it, they’ve moved on to the next shiny object. Meanwhile, the Product team wants to do things right. They want to avoid reinventing the wheel and maybe, just maybe, get credit for delivering the thing Sales has already forgotten about.

I’ve been on both sides. This tension is essential, but in smaller companies, it plays out in a way that can become paralyzing.

I’ve worked in environments where strategic planning—beyond basic revenue and expense forecasting—was seen as fundamentally antithetical to the "entrepreneurial culture." There’s a fear that long-term thinking will kill the hustle. The logic usually goes like this:

• Survival instinct: Reacting to near-term opportunities is what keeps the lights on.

• Fear of focus: Long-term planning might distract us from the "urgency of the now."

• Option paralysis: If we commit to a future direction, we might have to say "no" to a quick win today.

• Stagnation: A general discomfort with actively facilitating—rather than just reacting to—change.

I could go on forever about how hyper-focusing on short-term opportunism kills creativity and problem-solving, especially when those "easy" opportunities stop falling from the sky. But here’s the reality: even the most opportunistic companies can be reflective. You can be a "hustle culture" firm and still make deliberate, incremental progress on your workforce.

Mastering the Short and Long Game

I used to use a golf analogy for this: you need a short game and a long game to win. While that’s a helpful frame, I’ve found that living in this tension requires asking more pointed questions to bridge the gap between today’s fire and tomorrow’s growth.

1. What does "10% better" look like for our roles next year?

If your Project Managers performed 5% or 10% better, what would that actually look like in practice? You likely have aggressive revenue goals, but the target here is driving incremental workforce improvement. This allows you to chase ambitious market goals without burning out your human capital.

2. Where do our people actually create value?

It sounds basic, but you have to step back. Whether you’re a boutique services firm, a product shop, or a non-profit, where do your human assets contribute the most to the value you build? Identifying these "value centers" helps you decide exactly where to target your limited training and development energy.

3. The "Post-Mortem" in Reverse.

Take a "pre-mortem" approach to identify risk. Look into the crystal ball: it’s one year from now and you’ve just lost your three most important clients. Why did it happen? Working backward from failure often reveals the strategic gaps that your "opportunistic" side is currently ignoring.