Most every startup begins with one or two people and an ember of an idea they are trying to spark to life. The dream of an established company, one churning with employees and team lunches and office perks, might be out there. But in those first days, hiring people--taking on salaries and benefits and the overhead of an actual real-life staff--seems rather insane.

Soon enough, though, if your idea takes hold, you'll need help. That means hiring. Two options here. The first is to make a wish-list org chart and start filling in the blanks with specific roles and precise duties to be assigned to exceptional and experienced candidates. The second is to go broad: Bring on people with various skills, lots of enthusiasm, and endless energy to learn.

Let's be honest--most startups take the second route. The path to success is to start scrappy. Hire people with a range of skills who can pitch in pretty much anywhere. Look for inspired fast learners and go-getters. If they don't have all the skills, then substitute adaptability and willingness to learn.

Being scrappy, in my experience, is one of the best things about entrepreneurship. Making a bet, green-lighting a project, and rallying all hands to execute a quick-and-dirty launch is one of the most exhilarating professional experiences I've ever had. My team loved it too: People who'd been hired for, say, marketing gladly jumped into product design, while designers spent their evenings learning to code, just so things could happen faster.

Scrappy is individual employees owning a wide swath of responsibilities and pitching in to get something done whenever necessary. Early on at my startup, one person hired for marketing was soon also managing product, business development, and human resources. Being scrappy is learning new things and having fun.

At some point, though--call it 20 or 25 people--you have to shift from scrappy to structured. Welcome to your company's first culture shock. Structure means that org chart actually gets drawn, and duties are delegated or diverted. Early employees have to hand off responsibilities to new folks, people who may well have more polished pedigrees and different opinions on how to do things.

This makes perfect sense on paper. But in person, it's incredibly delicate. Basically, you are taking responsibility away from people who've given their all; you're suggesting that someone else could do part of their job better. Understandably, that can make reasonable people rather upset.

I confess that I have--more than once!--misjudged and misplayed this. I've carved off duties into a new role, blithely assuming that the team members who'd been shouldering this extra burden would happily give up some of their load. The angry emails I got from them made it clear that giving up turf is difficult for people.

In retrospect, the best course of action would have been more transparency, all along the way. I should have shared my future org chart with early employees and asked them to help plot their own course on that map. What path did they want to take, and how could new hires help them get there? What areas demanded immediate attention, and what roles did I need to hire for first?

This isn't just an issue of getting early buy-in to avoid unpleasant conversations. As founders, we see our needs from a 10,000-foot-high gaze of our own assumptions and impressions. But often, it's those early believers who have the best sense for where the gaps are and how the mistakes happen. Hiring is always hard. But especially as that scrappy original team grows into something more structured, remember: The ultimate prize is success.