Finding The Right Fit As An Entrepreneur

Small businesses often hire out of necessity rather than design, whoever's available gets whatever needs doing, regardless of whether the role actually matches their natural strengths. In a recent conversation on my podcast, this theme kept resurfacing in different forms, and it's worth examining directly, because the mismatch is more common, and more costly, than most founders realise.

Some people are naturally strong starters, full of energy at the beginning of a project. Others thrive in the middle, sustaining momentum through the unglamorous grind. Others are finishers, the ones who actually close things out. Forcing someone into a role that fights their natural tendency, asking a starter to grind through completion, or a finisher to generate the initial spark, produces resentment long before it produces results. People will tolerate a mismatched role for a while, but they rarely stay in it.

It's tempting to manage every team member the same way regardless of where they're based, but that assumption doesn't hold up in practice. Jeremy Yang, who runs a digital advertising agency and hires across several countries, described a clear distinction when we spoke: handing someone a course and expecting them to independently absorb it and report back works reasonably well with a locally based hire, but rarely works the same way with team members in different cultural and work contexts, where more structured, hands-on guidance is often needed to get the same result. Assuming one management style transfers universally across a distributed team is a quiet but common source of frustration on both sides.

A single disappointing lead, a wasted call, an expensive click that went nowhere, can derail an entire day if it's allowed to. Treating every setback as data rather than a personal frustration keeps decision-making clear-headed, especially in businesses where a single lead can cost real money to acquire. The founders who let one bad outcome colour their whole day tend to make worse decisions for the rest of it, compounding the original cost.

Sending traffic, whether from ads, referrals, or organic reach, toward a business whose messaging or branding isn't ready is a reliable way to waste money regardless of how good the acquisition strategy is. Confused visitors don't convert, no matter how well-targeted they were on the way in. Fixing the foundation, clear messaging, visible trust signals, an offer that makes sense at a glance, has to happen before scaling anything, or the scaling simply amplifies the confusion.

Whether it's a team member in the wrong seat or traffic arriving at a business that isn't ready to receive it, most "fit" problems trace back to the same root cause: skipping the work of matching effort to what actually works, rather than what's simply available. Get the fit right first, and everything downstream gets easier.