How Do You Know It's Time to Hire?

Founders ask us this all the time. Usually, the round of funding has just closed, or a board member or somebody they respect has told them that a role should be added. The round finally closes and it is a good day, worth celebrating, and then a lot of pressure comes with it. And there is a question you have already answered before you even ask it. Who do I hire first?

But look at what that question already assumes. It assumes that it is time.

So before we talk about who, we like to ask three questions.

1. Can you write the outcomes of the role, not the responsibilities?

What needs to be true at six months, at 12, at 18, because this person was there? If you can write those things down, then it may be time to hire. If you cannot write them down, that does not mean the pain is not real, because it usually is. It means you would be hiring someone to take the pain away instead of hiring them to do the work, and a job description written while you are in pain almost never comes out right.

2. What is the actual scope of the role?

Hiring a full time person is only one of several options, and it tends to be the most popular choice. A better question is what you are trying to get done over the next six to 12 months, instead of who should sit in a seat for 40 hours a week. Sometimes the answer is a fractional executive who can do senior level work for you for two or three months. Sometimes what you need is a few hours a month of good senior judgment from an advisor who has real equity, a path into the seat later, and a reason to care how it turns out. And sometimes the answer is that the hire can wait a while longer, and getting to that answer early is worth more than filling a seat quickly.

3. Does this hire fit the company you are building, or the company you have today?

The people you hire early set the pace for everyone who comes after them. So think about what you want this company to look like three years from now and whether this person gets you there, especially right now, when the work itself keeps changing while you are still interviewing. If you design the role around only what you need today, it will already be out of date by the time the offer goes out.

What the odds actually look like

None of this is about founders being careless, because the odds are hard on everyone. Heidrick and Struggles went back through 20,000 of their own searches and found that about 40 percent of the senior executives they placed were pushed out, failed, or quit within 18 months. DDI asked 1,700 HR leaders about the same thing and came out closer to half for executives hired from the outside. These are companies with search committees and real budgets and people whose entire job is hiring, and they still get it wrong that often. A company with 15 people is making the same bet with less information and far more riding on it.

And most of the time the decision comes out of pressure rather than out of the work. The round closed, so adding headcount feels like progress. A function hurt this week, so somebody writes a job description out of the pain. Then the search starts with paper, a description borrowed from somewhere else and 10 years out of date, and everyone moves fast to find a person who matches it. You fill the position faster that way and you fill it worse, and you will not find out for two quarters. At 15 people the wrong executive costs you more than a salary. It costs you six to nine months of a function running badly, and it costs you the good people who take on a bigger workload and then start taking calls from recruiters, and it costs you a quarter of your runway.

Austin makes this harder, not easier

This town runs on who you know. There is a founder dinner, a group chat, an Instagram group, and four people who all worked at the same company back in 2019 and moved here around the same time, and the short list writes itself before anybody opens a search. Keep the referrals, because the best ones come from your high performers.

And here is the part that gets missed. Austin is one community made out of many small ones, and most founders really only live inside two or three of them. There is the running club that meets before work, and the padel club, and the pickleball, and the golf. There is Barton Creek, and Westlake, and Tarrytown, where the same families end up at the same clubs and the same schools. There is Capital Factory downtown, and the Austin Technology Council, and the Austin Young Chamber, where the people who will be running things in 10 years are already showing up. There is Rainey Street on a Thursday. There is the Hyrox and CrossFit crowd who see each other at five in the morning four days a week and know more about each other than most coworkers do. There are the membership clubs, Soho House, Townhome, Commodore Perry and the rest of them. There are professors at UT and at St. Edward's who know exactly which of their graduates from six years ago are ready for something bigger. The person you need is sitting in one of those.

There is plenty of talent in this town. The question is who is connected to it. When you move between these groups it is easy to assume that everybody knows everybody, because Austin feels small. They do not. The running club has no idea who is at the Young Chamber. The padel people and the Capital Factory people pass each other on the street and never meet. So if your short list only comes out of the rooms you already sit in, then what you are looking at is your circle and not the market.

This is why referrals matter, and why we spend most of our time on them. You are not going to get a feel for a person from a resume, and you are not going to get it from a LinkedIn profile either. Those tell you where somebody has been. They do not tell you whether this person is going to be successful at your company for the next two years, and that is the whole question. Getting to that takes conversations, with the person and with the people who have worked with them. So when somebody arrives already vetted, and from a pocket you were never going to reach on your own, you start a long way ahead of where you would have started. That is the part we do. We are in the rooms you are not in, and we can go find the person who has never been to your founder dinner and has no idea you exist.

There is an order to this and the order matters. Scope first, because you cannot recognize the right person until you know what the role has to produce. Referrals second, because that is where the person actually comes from. Then a rubric, and the same questions for every candidate, because unconscious bias is in all of us and in a network this tight it travels fast.

At the executive level the interview still has to feel like a conversation. There is presence, and there is gravitas, and those only come through when the thing is real and not a list of questions read off a page. But underneath the conversation there has to be a rubric, so that you are scoring the same things across every candidate instead of scoring how much you liked them. Keep the structure out of sight and keep the conversation human. The ones who cannot hold that conversation will show you quickly.

Last week we were on a call with a founder here in Austin who was close to closing her first real round. She had built the product mostly by herself, after two engineering teams that did not work out and a hard lesson about hiring before you know what you are hiring for. All her growth had come from word of mouth, without a dollar of paid marketing behind it, and the numbers were good enough that investors leaned in. She came into that call ready to open three searches, and one of the job descriptions was already written.

We asked her to set the titles aside for a minute and tell us what the business had promised over the next 18 months, and what was still on her own plate, and what the software should be doing, and what needed a human being who does not work there yet.

On the first role she wrote the outcomes without slowing down at all. Growth was already happening and it was compounding away from her every week, and she knew exactly what month 12 had to look like because she had been doing that work herself at night. That one passed, and it got a scorecard and it opened.

On the second one she started listing responsibilities instead. We asked her again what had to be true at six months, and she stopped and told us she did not know yet. She was not being careless about it. The work had not taken its shape, and she had written the job description anyway because somebody she respects had told her the role was missing. That was the moment the call changed.

The third one was harder for her, because she wanted to hire someone she already knew, someone good who happened to be available. We did not tell her not to. We asked her what that person would have to make true by month 12, and after a pause she told us the honest thing, which is that she wanted the help and had built a role around getting it.

Two of the three ended up as advisors with real equity and a path to the seat later. And the last thing we found was not a hire at all. It was the foundations, the mission and the values and an org chart with real dates on it and how people work together, written down now while the team is still small and it is still cheap to do.

She got on that call expecting to open three searches, and we opened one.

Why the conversation belongs earlier

She should not have been answering that question for the first time in the same week the money hit the account. That is the worst possible moment to start thinking about talent, when the pressure is at its highest and the cash is at its highest and nobody has prepared for any of it. The only reason that call went as well as it did is that we already knew her business before there was anything for us to sell her.

There is also something about the way this works that nobody bothers to explain to founders. Once a recruiter understands what you are building and what the profile looks like, they start working on it for you whether or not anything is open. They are at dinners and on calls that have nothing to do with you, and your company is sitting in the back of their head the whole time, and they are quietly building a bench for you. So when the work finally says it is time, the first names are already there and the search starts somewhere in the middle instead of at the beginning. None of that costs you a thing, because you do not pay a recruiter to think about you. The retainer starts when the search starts and not a day before.

That is why the conversation should happen earlier. A coffee, a look at the plan, an argument about whether that VP role is real or not.

That founder calls us now when she has nothing open at all. Those are the best conversations we have.

Come talk with us before you need us at peopleatx.com. Our 2026 Talent Report is at peopleatx.com/report.

People ATX. Co-founded by Jami Adkins and Andrés Traslaviña, former Fortune 5 talent leaders. Talent strategy · executive and retained search · AI change management.

Sources: Heidrick & Struggles, review of 20,000 searches (Kevin Kelly, Financial Times). DDI, Leadership Transitions, survey of 1,700 HR leaders.