Small companies can have serious trouble filling stubborn roles. In fact, finding talented employees is often cited as one of the biggest issues facing entrepreneurs and small business owners.

The good news? By being creative, detailed, and process-driven with recruiting, tiny companies can land extremely talented candidates—even on an extremely tight budget.

Springboard, a 60-person education-technology startup in San Francisco, recently hired a former Fortune 100 mover and shaker as a VP on their small, five-person leadership team. The question is, how do you compel someone with cruise-ship experience to hop on a small canoe?

Here’s exactly how Sim Thadani, Springboard’s Talent Acquisition Lead, was able to get such a moonshot candidate to join her team.  

Secret #1: Emphasize that this is a “key role”

In December, Thadani’s dream candidate applied. No, it wasn’t a glitch—it was because her job description read like a thriller. “A good job description is like an email subject line: it gets you to open,” she explains. “Start there to sell the opportunity.”

Her secret to capturing attention: “Subtly remind them of the importance of the role (and therefore, their own importance) in all your communications.” 

Thadani folds in the phrase “key role” or “critical role” every chance she gets: in the job description, emails, phone calls, interview wrap-ups, even offer letters.

– “It’s a key role, so we’re moving quickly.”

– “You’ll play a critical role in changing how we think about our strategy.”

– “This is a key role, which is why I think you’re a fit.”

The most important part of the description should outline the opportunity, not just the role. It’s not just what they’ll be doing, but why they’ll be excited about doing it.

Here’s an example from a different role that Thadani is working on:

The Opportunity

Springboard’s offering is technology-enabled but very much human-centric. Our first [TITLE] will tie together and advance the work of all our external-facing human touch points (mentors, student advisors, career coaches, relationship managers, and more).

This is a rich, multifunctional, collaborative role: you’ll work on solving hard problems; directly impact the learning experiences and career outcomes of tens of thousands of students and professionals; and shape the foundations of a multi-dimensional community. You’ll play a vital role on the exec team at a high-growth startup, influencing the direction of the company beyond your own function.

So if you’re hiring a salesperson, say you want someone to highlight the revolutionary things you’re doing. Talk about the company vision and the role’s impact—not just the day-to-day tasks.

Once the job description is tailored to attract ambitious, out-of-the-box thinking, the next step is acing the interviews.

Secret #2: Ask your candidate tough questions. And be prepared to answer theirs

Rigorous interview questions show your candidate that you take your business, and building your team, seriously. And that can make the role and company even more appealing.

Even though Thadani’s candidate was ultra-talented, she didn’t give him a free pass during the first interview. 

Here are some of the questions she relies on during initial phone screens:

– What is the single thing in your background that you’re most proud of?

Rather than the hackneyed “Tell me about yourself” or “Walk me through your resume,” this question cuts straight through the fluffy monologues to get to the heart of how the candidate sees their work and the world.

– Why do you want to be Springboard’s first [X]?

This simple question can elicit responses to many underlying questions: Why this role? Why this company? Why now? Are you daunted by the prospect of blazing a new trail? Also, a good communicator will understand the complexity of the question and address all these elements without being further prompted.

– Tell me about a time when something didn’t go according to plan, and how you managed that.

A good candidate will be humble enough to confess to failure, says Thadani. Many candidates actually start this answer with a laugh, and an admission that “This happens a lot!” The scope of the incident can often reveal the extent of the candidate’s growth mindset. And the best ones will share exactly what they learned from this stumbling block.

What are your compensation requirements?

Asking about compensation right away is respectful of everyone’s time. Many candidates don’t want to say, to which Thadani simply states the budgeted range, and asks if that suits them. Avoiding “the dance” right off the bat is something many candidates appreciate.

Heavier questions related to challenges and failures are traditionally saved for later interviews, but Thadani believes they serve a valuable purpose earlier on. “With a top-notch candidate, it’s definitely you doing the selling, but you want them to be impressed by you as well,” she explains. “Don’t shy away from the hard questions, because those are the telling ones.”

The second part is to encourage candidates to bring their questions: the deeper the better. The most compelling candidates, for Thadani, are the ones who ask about various aspects of the business, not just what immediately concerns their candidacy.

Springboard’s star candidate spent an extra hour with Thadani on the phone to ask about everything from annual revenue to user demographics to how decisions get made. Instead of flinching, Thadani saw it as an opportunity to further engage an already engaged audience.

Secret #3: Create serious FOMO

“You want to let them know the bus is leaving and they’re not on it,” explains Thadani.

This is particularly important if you’re trying to snag a candidate who is actively interviewing and may even have multiple offers on the table. If someone gets to them quicker than you, it could wreck everything you’ve been working toward.

So if you need them to respond before you move forward with another candidate, say something like,

“Just a quick check-in to see if you’re still interested; the team is interviewing several candidates this week/month, with the goal of closing this key role ASAP, and we’d love to keep the momentum and include you on the same timeline.”

Always create a sense of urgency.

Secret #4: Help your candidate succeed in the interview

Set clear expectations at every stage, especially before you bring your candidate on-site to interview with the rest of your team. This will streamline the process, establish trust, and make them more likely to blow people away during the interview.

Before every on-site interview, Thadani sets up an additional call with the candidate. The goal of the call is somewhat masked—Thadani tells the candidate that she wants to figure out the interview logistics, but really, she wants to see if they’re still motivated.

Here’s the script she runs through:

– How are you feeling about the opportunity? How have your meetings gone so far? On a scale of 1-10, how excited are you about this position?

Anything less than an 8 means uh-oh!

– This role is located in our San Francisco office; are you able to be in the office 5 days a week?

This often raises questions about relocation, commuting, or work-from-home benefits.

– Will you now or in the future need us to sponsor you for an immigration-related employment benefit?

If they say yes, ask if they can share any information to help you facilitate the sponsorship.

– Have your compensation requirements changed? Any questions about our stock options or benefits?

Secret #5: Gauge how likely they are to accept by asking this question

If that pre-on-site check-in call goes well, Thadani likes to wrap up by asking a version of this question from Lou Adler, a best-selling author who writes about recruiting.

  • “If we made you an offer, when might you be able to start?”

“The idea is to get the person beyond the mental hump of the interview process, and already imagining joining the team,” she explains. “If they aren’t ready to accept, they’ll signal that to you by dwelling on timing, or compensation, or title, or whatever is on their mind.”

This information is essential, so you can either sell the candidate hard, or save the time of going through on-sites, reference checks, and offers, only to get turned down.

Secret #6: Reference check like your job depends on it (Because it does)

Your goal: Not finding any hidden skeletons. Thadani does something called “back-channeling,” where she scours her and the team’s LinkedIn networks, so she can reach out to people the candidate worked with beyond the direct references they submitted.

She asks each reference the following questions:

– Would you say this person is exceptional (i.e., among the top 5% of people you’ve worked with) on some dimension? What is that dimension?

The best kind of answer? One that begins, “Oh yes, they’re not just top 5%, they’re top 1%!”

– How has working with this person impacted your own career trajectory?

For an exec hire, you want someone who has positively affected the life of the person you’re speaking with.

– What are some areas of improvement or development that this person had back then? What else?

“Don’t give up easily if references don’t want to talk about weaknesses; remind them that no one is perfect and that your job as a recruiter is merely to get the team as much information as possible,” shares Thadani.

– If we had to build a team around this person, what skills would those other people have to bring to round out this person’s skill set?

This is another way to get to areas of improvement, but it can also yield other insights about their teamwork and collaboration style.

– Would you hire/work with them again?

A lukewarm answer here is basically a no.

– If I could talk to one other person who can give me *a different perspective* on them, who would you send me to?

This last question helps connect you to other references. You can clarify that you’re not actually going to pick up the phone, but this gives you a sense of the candidate’s integrity in providing meaningful direct references.

If all looks good, the hiring manager makes the offer—not Thadani. Offers are often made on Fridays, with decisions due on Mondays or Tuesdays at the latest. It’s a quick turnaround, but it also reinforces that FOMO feeling. Now that they’ve made it through, why not show them you want them?

With the VP-level candidate, an offer was made on Friday at the end of the day. A few different teammates and a Board member hopped on the sell wagon over the weekend, reaching out to congratulate him and express excitement at the chance to work together.

When their candidate finally accepted his offer the following Tuesday morning, the office exploded in cheers.

Bonus secret #7: Use Thadani’s favorite recruiting tools

Here are some of the tools that help Thadani streamline the recruiting process.

The Muse

Springboard has a paid profile on The Muse, which helps them drive traffic to their job postings. The profile includes information about the team, culture, and any open roles.


MixMax is “basically like email on steroids,” says Thadani. The tool allows her to seamlessly schedule meetings and see when people read her emails, allowing her to follow up quicker. It also helps her tailor follow-up messages, in case someone reads an email but doesn’t respond.


Thadani relies on Lever, an applicant tracking system, to schedule individual and panel interviews, and track candidate progress through the recruiting funnel. She can also set up email templates for each communication stage, which makes it faster to talk to candidates. “It helps you do your future self a favor,” Thadani says.

You have a lot to offer a candidate with an impressive background. So don’t get intimidated by their success, and instead focus on the mix of strategies that can help you secure a “yes.”

“Even if a candidate doesn’t have small-company experience, they can still have a small-company attitude,” says Thadani. “And if you get them, it will change the path of everything that comes after.”

Kira Deutch Kira Deutch is a former Gusto editor. She has a background in publishing and content marketing for startups.
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