If Hiring Isn’t Uncomfortable, You’re Missing Out on Great People

Startup founders and people leaders need to embrace the cringe and respect the long game to connect with great talent, nurture relationships and bring the best people into the fold.

"Hiring is your #1 job."

As a startup leader, you've probably heard this phrase countless times. But what does it really mean when you're juggling multiple priorities that all feel like they should be #1? The truth is, the people you bring into your organization don't just fill roles – they shape your company's future. Most founders and hiring managers may get that, but it’s easy to say and hard to execute on.

After being involved in thousands of hiring decisions, I've identified six uncomfortable but essential truths about hiring great people. They’re uncomfortable because they’re either things that are hard. Or often counter-intuitive.

For example, should you spend more time now so you can save time later? A time value of money extrapolation makes this seem like a bad idea. But if you do nothing else, these things will help you build a stronger pipeline, waste less time on unsuitable candidates, make better hiring decisions and create a network of people who speak positively about your organization – even if they never join it.

1. You will only win if you are #AlwaysRecruiting

I used to work for a CEO who would compare recruiting to salmon fishing. You open a role, you go stand by the river and you catch whatever fish you can get swimming through at that time. Crazy, right? What if the best salmon for you actually swam by 5 minutes before you showed up? Is that the right reason to miss the right person for your company? Of course not.

So, what can you do? An Alec Baldwin character famously said “Always. Be. Closing.” The recruiting version is “Always. Be. Recruiting.”

The best candidates are rarely actively job hunting. They're excelling in their current roles, making waves in their industries, and generally not browsing job boards. This means you need to play the long game. Maintain a list of impressive people you meet and nurture these relationships consistently. The perfect candidate might not be ready to move today. But they could be your next great hire in six, twelve, twenty-four months.

2. There’s no point in just jumping in and interviewing people, you need to meet the best first

Most hiring managers skip the crucial step of really understanding the role they're hiring for. Before you write that job description (or gasp, start talking to candidates!), make it your mission to meet with at least five exceptional people for benchmark calls. Ask people you know and trust who the best [insert role you’re hiring for] that they’ve worked with.

Don't try to recruit them – learn from them. It's key to set your bar first, interview later. This investment of time upfront will save you countless hours of interviewing the wrong candidates later. Pro tip: Ask these stellar people for their referrals and go from there.

3. The process is useless unless it has purpose

Many hiring processes are unintentionally wasteful, with multiple interviewers asking candidates the same questions. It's uncomfortable to admit, but traditional interviews often yield little valuable information. Instead, design a purposeful process where each conversation gathers different insights. This not only respects everyone's time, but also creates a more positive candidate experience. Just recognize that you may have more variability in interview outcomes.

If everyone is truly interviewing for something different, you’ll get answers of “yes” and “no” based on different dimensions of the candidate. And that’s ok, it’s how you deal with that feedback and prioritize different traits that’s most important.

4. Interviews are generally a waste of time – put candidates in the job

Here's a hard truth: Traditional interviews are mostly a waste of time. The best way to evaluate candidates is to see them in action. Design exercises that simulate actual job responsibilities for every role you're hiring.

A well-crafted exercise will tell you more about a candidate's capabilities than a dozen interviews. Plus, it gives candidates a realistic preview of the work they'd be doing. Taking this approach saves the candidate time. And you as well.

5. You can’t outsource references… unless you want to waste your time

Many leaders delegate reference checks or treat them as a mere formality. This is a mistake. Reference checks should be reference interviews. Conduct these calls yourself, and approach them as interviews, not checkboxes.

Drilling down, it’s important to focus on past managers rather than peers (we all have our work best friends who will say wonderful things about us – skip those calls) and come prepared with specific questions. You know what you need best and because you’re taking these calls yourself, you can actually have a deep, dynamic conversation with the reference.

6. Every interaction is part of your pitch

Recruiting is a two-way street from the very first interaction. Think that the fact you showed up late and unprepared for the first call with a candidate doesn’t matter? It does. You're not just evaluating candidates; they're evaluating you, your company, and how you operate. Every email, every meeting, every follow-up contributes to their impression of your organization. Remember, candidates talk to their networks about their experiences. Your next great hire might come through a referral from someone you interviewed but didn't hire. Keep that in mind. Every interaction matters.

All this to say, hiring is so much more than filling an open position. It's about playing the long game when necessary and building the foundation for your company's future success, one great hire at a time. Here’s wishing you a successful year of hiring going into 2025.