After eight years of building teams, I’ve learned a few things about what a startup actually needs from its people. Just be easy to work with.
Skilled? Yes, of course. A good communicator? Even better. Experienced? Sometimes, though not always essential. But what happens when someone checks every one of those boxes and is still difficult to work with? That’s the gap between someone difficult to work with and someone who’s actually easy to work with; and it’s taught me more than any podcast or business book ever has.
It changed how I promote people now. Most founders ask who’s the smartest person on the team. I ask who makes this company easier to run; not a co-founder, not someone challenging your strategy every meeting, just someone who does the work well, gets better without being asked, and never becomes something you manage around.
What Being Easy to Work With Actually Means
None of this is about being agreeable. It’s about how much of your attention a person requires to function well, and how much they hand back instead.
They finish what they start.
No reminders, no chasing. A deadline is something they track themselves, not something you track for them. If a piece is running late, you hear about it before it becomes a problem, not after a client asks where it is. The work simply arrives, on schedule, without you having to think about it twice.
They improve without being told to.
Nobody assigns “get better at this.” They notice a gap in their own skillset and close it quietly, a course, a habit, a tool… without turning it into a conversation about how hard they’re working. Six months later, you notice the difference before they ever mention it.
Their work doesn’t come back to you.
You don’t redo it, proofread it twice, or clean it up before it goes out. What lands on your desk is close to finished. Fewer versions, fewer corrections, less of your time spent fixing someone else’s draft. You stop double-checking after the first few times it happens.
They raise real problems, not manufactured ones.
A genuine blocker gets flagged early, with enough detail that you can actually act on it. A minor annoyance doesn’t become a meeting, an email thread, or a reason to interrupt your day. You learn to trust that when they do bring something up, it’s worth your attention.
They take small things off your plate.
A form that needed filling. A client email that needed a reply. A broken step in a process, quietly fixed. None of it escalated. None of it waiting on your decision when it didn’t need one. Half the time, you only find out because someone mentions it in passing.
They stay accountable on their own
If something’s behind schedule, you hear it from them first, not from a client, not from a teammate, not because you asked. Accountability isn’t a performance reserved for the days you happen to be watching. It’s the same whether you’re standing over their shoulder or three time zones away.
They own outcomes, not decisions.
They’ll chase something to completion, fix what’s broken along the way, take responsibility for how it turns out, but they don’t quietly start deciding things that were never handed to them. They guide the process, do not dictate people.
How to Keep People Who Are Easy to Work With
These people are easy to miss. The person who needs constant follow-up gets talked about in every meeting. The person who quietly solves problems rarely comes up at all. It’s easy to end up rewarding visibility over actual value — and lose the second person before you’ve noticed how much they were doing.
Pay them properly.
Purpose doesn’t pay rent, and neither does a good LinkedIn recommendation. They have families, ambitions, and other offers sitting in their inbox. Money is one of the clearest signals of what someone is actually worth to you. Underpaying your best people rarely saves money — it just delays the cost until they leave and you’re paying to replace them.
Let them know they’ve been heard.
You won’t say yes to every suggestion. Acknowledge it anyway — being heard and being agreed with aren’t the same thing, and silence reads as dismissal even when that’s not what you meant. A short reply explaining why an idea won’t work goes further than no reply at all.
Train them.
Don’t hand someone more responsibility and act surprised when they weren’t ready for it. Match consistent effort with the knowledge and exposure that lets them actually use it. The training almost always costs less than the mistakes you make by skipping it.
Tell them where they stand.
In an age of quiet layoffs, people are anxious enough without your silence adding to it. You can’t promise forever. You can be honest about where they fit as the company grows, and update them as that changes instead of letting them guess.
Let mistakes be mistakes.
The one time they get something wrong, throwing them under the bus teaches your best people to stop taking responsibility at all. Protecting them in that moment earns the kind of loyalty a raise can’t buy, and it tells the rest of the team exactly what kind of founder they’re working for.
Skill gets someone hired. Communication gets them noticed. Experience gets them trusted. But being easy to work with is what actually keeps a small company running — it reduces the amount of work required to manage the work. No résumé measures it. Promote for that.