4 Hiring Struggles You Should Know About


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The featured image for this blog post.

A peek into our hiring

No bones about it, hiring is hard. The first time you do it—and the 5th time you do it, too.

In the past, we’ve talked about writing a strong job post and a bit of our hiring process. We’ve also looked at the flip side of hiring from a candidate’s perspective (no really, a candidate wrote the post in that last link! 👀).

Today, I want to take a step back and share a Mount McKinley view of our overall process, plus point out four things that are tricky about that process.


Partly because how we hire has changed since we last wrote about it *checks calendar* over a year forever ago. Plus, we’ve learned so much from companies who’ve transparently shared their hiring process, it only makes sense to share ours as well.

Our current hiring process: an overview 🏔

First some context. In the past few years, we’ve needed/wanted to hire for a few different reasons:

  1. To increase our bandwidth (hiring the very talented Iris to widen our design bandwidth)
  2. To fill an important skills gap on our team (bringing in our incredible project manager, Bina, to help us streamline projects)
  3. To fill a gap an exiting team member leaves (finding Ronnie, our newest awesome front end developer)
  4. To provide mentorship to junior members in the community (okay, we haven’t done this yet—but we really hope to in the near future!)

Once we decide we need to hire—and determine we can afford to—we follow this process:

*Strategic in terms of what role we’re hiring for, as well as who we’re looking to recruit. We work with several platforms that specialize in reaching underrepresented groups in tech, such as Diversify Tech and RemoteWoman.

**For easy skimming, I’ve left out steps like “lose sleep over making the right decision” and “agonize over sending rejection emails because we want to hire so many incredible applicants.” But know those steps are totally in there. 🙃

4 trickier parts of that process (stuff you might not have heard before) 😬

Now, each piece of that process could be its own newsletter. And maybe we’ll dive that deep someday. But today, I want to stay high-level and do some expectation setting; I want to share four principles you’ll need to know if you’re thinking about creating your own hiring flow.

1. Processes take a LOT of time and effort 😅

This is true both when you start building a process and again when you start refining it.

When we started building one, Andrew said, “if I had to sum up the whole process, I’d say this: Hiring is really, really hard. It’s difficult to find candidates, and it’s hard to know whether anyone you find is good. And it’s not like you can take a break from running your business while you do all this either. No matter what way you slice it...hiring is a difficult process.”

Lately, we’ve been refining and documenting that hard process in our internal playbook. This is so we can:

This is hard, too.

Right now, it means me interviewing team members, drafting up the process in Notion, then circulating it back to the team for review (note that’s a minimum of 4 team hours per item!). So far, we’ve documented how to promote a job post and how to email candidates and created templates for both.

And we still have many more parts of the process to get down.

⭐️ If you’re planning on hiring, remember this… creating, documenting, and refining any kind of process will darn near drain you. But the earlier you can document what you do, the easier it will be to audit and improve it over time.

2. Being HUMAN while hiring also takes even more time and effort 👐

If you’ve applied for jobs before, you know it’s about as fun as an ice bath. 😑 You pour your heart, soul, and remaining self-confidence into an application, send it out….and then have absolutely no idea whether it reached someone’s desk or time-warped into Strong Bad’s spam folder.

One way we try to make our experience better is through update emails. We email applicants at every stage of the hiring process so they’re not in the dark. Some of the emails are bulk because we get many applicants. But even our bulk emails provide feedback around:

Plus, applicants who make it to the later stages receive individualized feedback.

If you’re planning on hiring, remember this…most candidates have had at least one bad hiring experience. From the way your word your job posting to the way you close out the position, make sure you provide a good experience. Don’t discourage applicants from applying again or from referring another candidate to you. Treat every candidate with respect.

3. Most processes aren’t perfectly linear 📈

We leave some job posts open longer than others. Sometimes we do phone interviews, aren’t thrilled about the candidates we’ve interviewed, and circle back around to the qualified candidates pool. We’ve added and removed steps to our hiring process. All that is normal.

If you’re planning on hiring, remember this…progress is rarely a straight, uphill line. It’s okay if your journey doesn’t feel as smooth as a gondola ride.

4. There’s always room for improvement 🤔

Last week, we shared what we learned from a Diversity and Inclusion audit. There were several takeaways for our hiring process, including improving the questions we ask and the rubric we use to assess candidates. We’re still improving (we’ve by no means “arrived” at the perfect hiring process), and we hope we never stop looking for ways to get better.

If you’re planning on hiring, remember this…ask for feedback from your team, trusted advisors, and even candidates. You have room to improve—look for those opportunities and ask others to help you see them.