Hiring for Startups: How to Recruit the Un-Recruitable

Startup recruiting is hard. The challenge is twofold: finding incredible talent and then making them want to join your team.

I’ve been doing the impossible task of hiring way above my "talent class" for over a decade, and it's one of the reasons why we could succeed with our sales platform in the hyper-competitive CRM space, where we're up against competitors with multi-billion dollar budgets. And here’s what I’ve learned about startup recruiting.

Little steps, not giant leaps

Don't ask amazing people to make a life-changing decision like coming to work for your company right away. That's a giant leap. It's too easy to reject that.

In fact, the type of person you want to hire should reject that. You probably don't want to hire anyone you can hire that easily just by throwing out an offer.

Instead, make the first step compellingly small.

Relationships progress in increments. Deepen the commitment step by step, rather than requesting someone to go full-in before they even had a chance to fall in love with your startup.

“A journey of a thousand miles must begin with a single step.” —Lao Tzu

Make it noncommittal, seemingly small and insignificant.

Step #1: Say hello

When you deal with rockstar talent, you need to get on the phone with them as soon as possible. The goal is not to offer them a job right away, but to get to know each other and start building a relationship with candidate. Make sure you keep it casual so people can put their guard down. Here’s what you say.

"Hey Mike! We just hired your friend Bob. Every time we make a new hire, we have a conversation and ask:

Who's the most amazing person you know who would never ever change what they're doing to consider joining us?

You know who Bob thought of first? Yep, you!

I know you're happy and there is no way you would come and work here right now, and that's fine. All I want to do is get to know each other since Bob made me very curious. :)

You are one of the most impressive people that Bob knows, so now I want to get to know you as well.

And in full disclosure—obviously, if there is ever even a glimpse of hope, I'm probably gonna attempt to hire you. But for now let's just put that aside. Let's just get to know each other."

Ask them questions:

  • What are their goals in life?
  • What do they want to accomplish?
  • What are they passionate about?
  • What do they love most about their current role, company, and team?
  • What's missing, what would they change in their current role, company, and team?
  • Etc.

Once you’ve gotten to know them, and you sense a potential good match, initiate the next small step.

"I'd love you to just stop by our office at some point, meet the team, give us some feedback. You seem to be really creative and really cool."

With this process, it's all about small steps. You go from a first phone call (first tiny step) to the next step (come in and meet the team, and give us a chance to meet you).

Step #2: Dating

The first meeting is usually them stopping by the office and spending time with the team, anywhere from an hour to a whole day.

Do you sense there’s a great connection? Are both sides getting more engaged and excited?

Now is the time to come clean and tell your potential superstar hire your intentions:

"I told you I would not attempt to hire you. I know there's not much hope. But I'm a bit of a romantic. It seems like this could be really great for both parties. Maybe there is a way for us to work together and get to know each other better before making any long-term decisions."

You indicate that you are interested, but you’re not asking them to join full-time just yet! It’s too early.

Remember, little steps, not giant leaps. It would be too easy to refuse your offer at this point and both sides have to do a bit more homework in order to really know that this is a great fit.

Instead, you say this:

"Hey, why don't you come for a whole weekend? We can work on a little project together. That would be fun!"

Step #3: Small commitments

So Mike spends a whole weekend with your team, and you have great work chemistry. You sense there’s a perfect culture fit. It’s time for the next step.

This step can be bigger. You’ve build some emotional momentum. Mike has already committed some of his time to your company. The steps progressively get bigger and all ultimately lead to the giant leap of making an offer.

Two good ways to do that would be to ask them to work with you:

  • on a part-time basis OR
  • as a three-month contractor or consultant

Here is your pitch:

"In all these meetings and calls we had, it seems like this could be a really great fit for both sides. Why don't you just come in for a little while, work with us and in three months if it doesn't work out, you can stop at any point.

That way we are both getting a chance to evaluate if this might really be the right next step for you, and for us. There is no way to really know until we've worked with each other for at least a little while. What do you say?"

If they’re truly a great fit for your startup, they won't be able to avoid gradually falling in love with your company and your team.

If they do, you simply pitch them to take the final giant leap and do the unthinkable of joining your company now that they know they can't live without it anymore :)

What if it’s a position they don’t want … like a sales job?

Sales hiring is particularly challenging because as a startup, you should not hire experienced sales professionals. You should hire talented people who understand business. And many of them don’t find the idea of being a “sales rep” and cold calling prospects very tempting.

Sales doesn’t enjoy a particularly good reputation.

When you think of "sales" or "selling", what’s the first word that comes to mind?

When Dan Pink surveyed people, he got replies like: pushy, sleazy, manipulative, dishonest and annoying.

Make it clear that it’s about your team and your vision, and not about “a sales job”.

Always sell them on the idea of working with your team and being part of your company, not on the exact execution of things and their position as a sales rep.

Understand their big goals, and their motivation for wanting to be in business. Help them realize how their goals and your job offer align.

Be rigorous and keep following up

Hiring great people is difficult. The easiest thing is to lower your standards, find someone who is subpar, talk yourself into believing that they "have it" and just give them the job.

Don't do that. Don't rush it just because you need to find someone quickly. In the end, hiring the wrong person will cost you more time than taking the time it takes to hire the right one. In some cases, it took me five years to hire someone—but it was worth every minute.

Use technology to make sure you keep nurturing the relationship. We at Close actually use our CRM as a ATS (Applicant Tracking System), and follow-up reminders are a great way to ensure that we nurture relationships even as the number of potential candidates grows.

In addition, using a hiring platform can also help streamline the relationship-nurturing process, allowing you to efficiently manage and communicate with candidates throughout the hiring journey.

close-crm-follow-up-reminder sales recruitment

Especially in the early days of a startup, you want to have a team of superstars. The process I shared with you today can help you hire the kind of talent that would usually decline the invitation to interview with you in the first place. And that's a massive competitive advantage.

Want more advice on hiring amazing talent for your company? Get a free copy of The Sales Hiring Playbook!

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