Here’s a thing I believe and have been saying out loud for so long that I’m a little bored of saying it: when you have a clean sheet of paper and a fixed amount of capital, you should spend it on the team before you spend it on anything else.
Not the technology. Not the user research. Not the brand work. Not the agency. Not even the office. The team.
This is one of those statements that everybody nods along to and then quietly violates the next week. I’ve watched it happen at every company I’ve worked at, including ones I was leading. So I want to take a swing at why it’s hard, and what I’ve learned makes the team-first instinct stick.
What I mean
When I say “pick the team first,” I mean two specific things.
First, do the hiring work before you let the project hit its sprint cadence. Don’t start the work, realize a month in that you’re under-staffed at one position, and then try to backfill while shipping. By month two, the team is shaped around the gap, the gap is shaped around the team, and you’re never quite running at full speed again.
Second, spend more than you wanted to on the senior hires that will define the shape of everything else. The lead engineer, the lead designer, the lead PM. These are the people who will hire your next ten people, set your bar, write your operating rhythm, and decide what gets cut. If you compromise on these roles, you compromise on everything downstream of them, forever.
The compounding effect
A good senior hire doesn’t just get you one good person. It gets you the next set of people better, because senior hires recruit their networks. And it gets you the set after that, because the rhythm and the bar are set by the first round. By month six, the difference between a team that did the team-first work and a team that didn’t is enormous and almost impossible to close.
Why this is hard
Three reasons, in roughly increasing order of importance.
The budget conversation is uncomfortable. Senior hires cost more than the budget you have. You will have to ask for the budget to be moved. The person whose budget it is will not love this. You will have to win that conversation, sometimes more than once. Most leaders don’t win it because they don’t try as hard as the conversation requires.
The timeline conversation is also uncomfortable. Senior hires take longer to land. Your CFO and your board are watching the ramp. Telling them “we’re going slower for the first quarter because I’m waiting for the right CTO” is a difficult sentence to say. It is also almost always the right sentence to say.
You have to be honest about who’s “the right hire.” This is the one I see leaders get wrong most. The right hire is not the most impressive-credentialed candidate. The right hire is the one who fits the specific shape of the work. A brilliant ex-FAANG engineer who has only ever worked on a thousand-person platform team can be exactly wrong for a five-person early-stage product. A scrappy generalist with a mid-tier resume signal can be exactly right. You have to interview for the shape, not the brand on the resume.
What “the right hire” looks like
A few signals I’ve learned to weigh, in order:
- They have shipped something close to what you’re trying to ship. Not perfectly the same thing. But close enough that their pattern-matching is going to fire correctly when something goes sideways. This is worth more than every other signal combined.
- You leave the conversation having learned something. If you walked out of the interview thinking the candidate is great and yourself is also great, you weren’t listening. The right senior hire is one whose thinking on the problem is better than yours in at least one important way.
- They make decisions in front of you. A candidate who can move from “let me think about that” to a clear position inside a thirty-minute conversation is a candidate who can lead. A candidate who hedges every answer is going to hedge with their team, too.
- They turn down something you offer. If a candidate accepts everything you put in front of them, like title, comp, scope, location, the whole package, no pushback – you’re either over-paying or hiring someone who’s going to take the same posture with the rest of their job.
What I do now
These days, the engagements I’m most often pulled into are pre-launch product reviews for early-stage AI companies. The single most consistent question I’m asked is “what should we be doing right now to set this up for success?” And in seventy percent of cases, the honest answer is: figure out who’s missing from the team, hire them before you do anything else, and stop trying to make the current team do the job the missing person is supposed to do.
This usually doesn’t make me popular with the founder. The founder wants to talk about the product. I get it. But I’ve seen this play out enough times now that I’m willing to be the unpopular voice in the room for the thirty minutes it takes to make the point.
Pick the team first. Everything else is downstream.
Steve