The 9 Most Common Questions About Hiring, Answered

Tips for hiring, firing and building a business with the best possible people.

Each month, we get dozens of questions for our Friday Q & A posts.

And each month, I respond to many of them with links to answers we’ve already posted before.

(I’m not complaining about that, it’s actually the biggest reason that I started publishing the series: so that I could link folks to an answer rather than re-writing it each time.)

Hiring is one of the most challenging—and important—things to do in a business, and it’s no surprise that a lot of the questions we see have to do with building a team.

Today, I wanted to share the nine most common questions we get about hiring (and firing), and how I approach each one.

To be sure, my answers aren’t fact—they’re simply based on my own experience—and there are many that are more qualified than me to answer. I hope that you’ll chime in with your own perspectives in the comments.

1) Should Startups Hire Junior Developers?

As a non-technical founder, I can’t evaluate a developer’s coding ability.

I can’t tell whether they’re making smart decisions as to the solutions they choose, and I don’t have the ability to coach them to be better developers.

So when I started Groove, I simply didn’t see hiring a junior developer as an option.

I suspect that the same will be true for any non-technical founder first starting to build their team.

However, now that we have a CTO and a team of senior developers, we also get value from having junior developers on the team. They can contribute and take some of the load off of the senior players, while getting great experience working side-by-side with those who can teach them to be better.

The context for the original question was from the perspective of a junior developer asking whether she should apply to startups.

While I can only answer from the perspective of the one doing the hiring, my answer to her would be that if you’re a junior developer and you really want to work for a startup, look for those who are either started by highly skilled technical people, or for those who have large-enough development teams (3+ full-time) to be able to keep a junior developer busy and also give them the coaching and support they need to keep getting better.

2) Where Do You Hire Remote Workers?

I love this question, because it hones in on an undeniable truth: not every good worker is a good remote worker (yet).

Successfully working from home is a skill, just like programming, designing or writing. It takes time and commitment to develop that skill, and the traditional office culture doesn’t give us any reason to do that.

We had some early hires—very talented people—not work out, only because they had never worked remotely before and we were unsuccessful at helping them develop that skill.

Now, we don’t just look for good startup employees, but we look for good startup employees with experience working remotely.

So, where do we find these people?

We’ve had three great sources of leads:

1. WeWorkRemotely.com. I have yet to find a job board online that consistently attracts high-quality candidates. It’s simple and easy to navigate, and we’ve hired two full-time employees there.
2. Networking. Building relationships (see my guide here) has a lot of benefits, and access to great talent is one of the biggest ones. Once you’ve put in the work to build a strong relationship, incredibly valuable introductions are often only an email away.
3. This blog. We get 50+ emails per week from readers of this blog who want to work with us. That’s how Matt, one of our awesome developers, joined the team.

Everyone on our team has either worked on a distributed team before, or been a freelancer or entrepreneur in the past.

3) Should a Startup Hire Full-time Employees or Contractors?

I actually did neither when I first started Groove. I hired an agency to build the first iteration of the product.

After that, I began building out our own team. First with part-time contractors, and then I hired those that fit best as full-time employees.

The answer to this question isn’t really one-size-fits-all; it’s more about what you can afford, and who you can find.

If, at the very beginning, you find an amazing developer who’s only willing to work on a project basis, you might consider hiring them to build your product.

If you can’t swing a full-time salary just yet, then obviously you only have the contractor option available to you.

If you have the luxury of being able to choose one or the other, I’ll say that I prefer the trial-to-full-time model, where a new employee does a trial project with us for a couple of weeks (or a bit longer if they’re already employed and need to do the trial project on nights and weekends), and if they’re a fit, we bring them on full-time.

Ultimately, I’m not sure there’s a right or wrong answer here in the beginning. Once your business is validated and you begin to build your team, then culture begins to play an important role in your team structure, and I think full-time is the way to go. You can’t grow a successful and sustainable long-term business with a team of mercenaries. Not that I’ve seen, anyway.

4) How to Deal With a Great Employee Leaving

This is a big deal for startups.

When an employee leaves a 20‑, 200‑ or 1000‑person company, bouncing back isn’t a huge deal, especially if the company has built a brand that talented people want to work for.

When an employee leaves a 4‑person company, that’s a quarter of the workforce gone in an instant.

But it’s simply a fact of life: it happens.

It happened to us, it may have already happened to you, and it’ll most certainly happen to most startups.

I wrote a longer post about this a while ago, but here are the main points to remember:

1) It’s Not Personal. Really.

If you want to hire the best (and I do), expect that they’ll behave like talented, ambitious people should.

Sometimes, they’ll outgrow the role you’ve given them. And if you can’t provide that next step, then someone else should.

They’ve worked hard and brought value to you and your team. Maybe they will again someday.

But for now, accept that it’s their time, wish them the best, and mean it.

2) Don’t Dwell On It, And Focus On THIS Instead

While good employees leaving is inevitable, not every single employee departure that happens is unavoidable.

So many startup founders—including me, in our early days—don’t do enough to make their teams love their jobs.

There are a lot of companies that think this means catered lunch or foozball tables in the office, but that’s superficial and doesn’t really get at the core of what makes great people love the work that they do and the business they do it for.

Ultimately, what it means will depend on your specific team, but I’ve found one great way to find out: ask, listen and actually act on what you hear.

Take the time, on a regular basis, to talk to your employees about their lives, goals and challenges. Ask them what they hope to accomplish, not just in the next week, but in the next year, five years and ten years in their careers. Listen intently to what they say, and think about how you can help them achieve that. And then act.

People have different goals.

Some will want to start a business of their own, become an executive in your company, have work/life balance so that they can focus their life on raising their family, work for a “dream” company someday, become an expert in a certain skill that they’ll be improving in their role, or any number of other dreams.

All are valid, and none are better or worse than any other.

But it’s important to know what that goal is, because if you can’t help them achieve their goal by giving them responsibilities that align with that goal, they’re going to ultimately be unhappy and ineffective in their position.

For more, check out Your Best Employees Will Quit. Here’s What To Do About It.

5) Should Early-Stage Startups Raise Money to Hire Developers?

Obviously there’s no blanket answer here that applies to all startups. But here’s my take.

There are things I would’ve done differently (and I’ve blogged about many of them), but raising more money isn’t one of them.

There are so many dangers to raising cash early on that I’ve seen materialize among friends.

One of the biggest is that there’s a really good chance that, like many startups, you may have to pivot to reach product/market fit. The investors who buy into your vision today might not love the thought of your new direction. A lot of people who think they want to invest in startups don’t truly have the stomach for what being involved in a startup really means, and they end up getting scared and becoming a distraction for the founder).

Dilution, too, is a very real de-motivator of founders and teams. You’re going to be paying a premium for capital when you’re still in the idea (or even prototype) phase, versus when you already have traction/‌customers and can get far more favorable terms.

It depends on your goals, too. For Groove, we wanted to build a sustainable long‑term business rather than a rapid ramp to acquisition. Going slow in the beginning and spending a ton of time talking to customers and refining the vision and product ended up being invaluable in the long run.

6) What’s the Best Interview Question to Ask a Remote Job Candidate?

This question, of course, is hypothetical; you need to evaluate a lot more than the answer to a single question in order to know whether you should hire a particular candidate.

But as the CEO of a remote team, there’s one question I keep coming back to, time and time again, that I find to be very revealing.

I love to ask: “what does your work setup look like?”

As a remote team, we need to hire not just great performers, but great remote performers; people who can excel at self‑starting and self‑managing. A big part of that is being thoughtful about your workspace. If someone hasn’t put much thought into their setup and works from their couch 100% of the time, or worse, “doesn’t know yet,” this signals that they might not be ready for a remote position yet.

There are a lot of right answers and very few wrong ones—we have folks working in everything from coffee shops to home offices to coworking spaces—but it’s important to me that some thought was put into this, either from previous remote experience or in preparation for future distributed work.

7) How Do You Find and Hire a Great Marketer for Your Business?

One thing that I’ve found, through a lot of frustration, is that it’s really helpful to be “hiring”—that is, connecting with as many hyper-talented people as you can—far in advance of when you’ll actually need to fill those roles.

I’m not saying that you should put up job postings and interview people that you know you’re not going to hire; don’t do that.

But the same way that you put value on connecting with mentors, advisors and peers in your field, put value on networking with people who might one day be great hires, and try to help them in any way that you can.

This makes hiring (when you absolutely need to hire someone) a lot easier, as you’ll already have a strong network of people who know and like you.

But if I were starting a search for a marketer today and knew I wanted to hire right away, I wouldn’t rely on a single channel or approach.

Instead, I’d take three paths at the same time:

1. Post a job listing on a site that’s relevant to your industry. I haven’t had great success with the signal-to-noise ratio on the broader job listing sites, but the ones more targeted to us—in our case, WeWorkRemotely is a great fit—have resulted in some really strong hires.
2. Tell the world what you’re looking for. Send personal emails to everyone that you know who might have a relationship with the kind of person you’re looking for, post to social media, pick up the phone… finding great people often requires a lot of hustle, because everyone else is looking for them, too. So put in the work.
3. Reach out to marketers that you respect. If you already read some marketing blogs, reach out to the people writing them. If you don’t already read any, then find the ones that people respect (here are some of my favorites). At the highest tier, the blogger might not be for hire, but they’ll typically have very strong networks that they can refer you to. And there are a lot of great lesser-known blogs with highly valuable content written by marketers that you can hire.

For more on hiring and how we approach it, check out these posts:

• How Our Startup Hires Top Talent Without Bidding Against Google
• Lessons Learned Building a Startup Team

8) How Do You Know Who to Hire Next?

I included this question because it’s something I struggle with myself.

We’re a small team, so each new employee sends relatively big waves through the entire company. We think very carefully about who to hire, and when.

From our own experience, there’s no “right” blanket answer for who each startup should hire first.

It depends on a lot of things.

But thinking about the issue in the right way, and asking the right questions, has helped me get a lot better about this:

• What’s our most pressing goal as a company right now? Do you need to ship product faster? Bring in more users? Get better at tracking? Be faster in support?
• Is the hole we’re filling going to continue to be a hole in the long-term, or can we fill it with something more temporary? Sometimes bringing in a contractor can be an economical solution that leaves you more financially nimble in the long run.
• What are you or your team spending time on that would be better done by someone else? This might mean that you have developers working on something that’s not in their domain expertise, and thus doing it 3-4x slower than a specialist would. It might mean that you, as CEO, are spending too much time doing marketing, and the effort would be best given to someone else. I’ve said before that a great goal for a startup team is to have everyone making the highest-value use of their time, always. You have to enable that to happen by hiring the right people so that everyone can do the things that they’re best at.

Like all startups, our goals and needs have been fluid from the start. Our first hires were developers, because we needed to build. Our next hire was a support person, because we needed to get our customers engaged. After that, we brought in marketing, then more devs, and so on…

So while I can’t give you the answer you probably hoped for, I hope that these questions give you some direction and help you arrive at a more concrete conclusion.

9) Am I a Weak CEO if the Idea of Firing Someone Weighs Heavy on My Conscience?

I chose this question because it’s the exact same question I asked a mentor of mine many years ago.

And the answer, of course, is no.

Feeling bad about firing somebody is not a sign of being weak. It’s a sign of being human. Of having empathy.

But actually following through with firing someone, if you’re doing it for the right reasons, is a sign of being a strong CEO. Of being able to make tough decisions that weigh on your conscience but are in the best interests of your customers, your team and your business.

Everyone you fire has rent or a mortgage to pay. They may have a spouse or kids to support.

It’s good to have empathy for that. It makes you a caring and cautious leader.

But it’s also important to see the big picture. That while your job is to serve your customers and your team, it’s to serve the greater good of those groups; and if keeping someone on board isn’t a good idea for the greater good, then it’s your job to fire them.

That feeling, though, doesn’t really go away the more you fire people.

And frankly, I’m not sure that it should.

For more on my thoughts on firing, read this post.

What Hiring Questions Do You Still Have?

I’d love to continue to build out the scope of the hiring questions we answer in our Friday Q&A.

What did I miss? What are you still wondering?

Let me know in the comments below!