Common Mistakes, Tackling Searching, and Skill Test: Ask Me Anything About Hiring in 2022

Talent and recruiting is a top-of-mind subject for everyone in today’s job market. It’s also a leading contributor to many headaches. With the hiring landscape on fire all of 2021, the state of the SaaS talent market has been a key focus for both OpenView and our portfolio companies going into 2022. As the talent partner at OV, I’ve been focused on helping our portfolio and prospect companies crack the code of recruiting by figuring out how they can best position themselves for a successful search process in this market. 

On February 10th, OpenView talent manager, Maggie Crean and I hosted an ‘Ask Me Anything’ on all things hiring, recruiting, and the state of our current talent market. Our audience of CEOs, founders, and executive hiring managers had no shortage of questions surrounding these topics. Here’s a recap of some of the questions and answers from the event:

What are your key tips for founders and CEOs trying to tackle a search themselves?

For founders, CEOs, and hiring managers who are going to tackle a search themselves, my biggest tip is to factor it into your day-to-day and block off time. It’s easy to get into it for 15 minutes before switching gears to something else, but you really need to block off maybe an hour a day to focus on recruiting and narrow in on what you’re looking for. 

Those who are new to recruiting have a tendency to think too broadly of where their target hire might be. Whether they’ve just come up with seed, series A, or are pushing to IPO, founders should always know their target universe. If you’re a developer company and you want to recruit candidates from that domain—candidates who know your audience, product, and end-user—that’s great. Ask yourself who those developer companies are that align with your product base, where you can have a strong degree of certainty that candidates are going to have the relevant expertise for your business. You don’t need to scrape the whole universe. Start with 10 to 15 companies.

You really don’t have to be a recruiting wizard to find talent. If you’re looking for a product manager and you really admire Datadog, you can literally type “product manager at Datadog” into Google and it’ll populate LinkedIn results. Once you find these people, you can start looking for similar profiles and start creating a list. Build a target mapping list by the function of people you want to get to know. Then reach out to them. 

What’s the most common mistake you see companies make in terms of their search process?

A big one that we see is misalignment across the interview team. Before you even kick off a search, it’s important that you sit down with the team of people who are going to be interviewing your candidates and make sure everyone is aligned on the target profile, the experience you’re looking for, and what values each interviewer is assessing within the interviews. 

Misalignment is something that candidates can spot from a mile away. If they’re in an interview process and they’re being told by a different person every time that the goals are different, they’re going to be running for the hills. And you’re not just scaring them off—you’re missing an opportunity to compel your candidates to your business. 

The second biggest mistake would be relying too heavily on inbound leads. In this market, going on offense as an approach to hiring is a way to get ahead of that network and get your company on talented people’s radars. The hardest thing in today’s market is just getting on the phone with candidates. Close to half of people aren’t looking for new roles. You need to have a bit more of a personal touch to make these connections happen. You can’t just wait around for your unicorn candidate to apply to your job posting, because chances are they won’t.  

How long should the interview process take and what should it look like?

Everyone knows how competitive it is to win candidates right now. I talked to a candidate to introduce them to one of our portfolio companies, and when we caught up just a few days later, he had already spoken with seven other companies. This just goes to show how quickly candidates can move from company to company and meet CEOs and founders. We recommend having a process that you could, if it came down to it, fit in a two-week time period. I see that as having around seven steps:

• Step 1: This would be a call with the CEO, founder, or hiring manager. Typically on this 30-minute call, you are exploratory, introductory, and focusing on selling the opportunity. I see this as the most important step in the process. 
• Step 2: The next step would be scheduling a follow-up call with the candidate—45-minutes to an hour where you can start interviewing. This is where you get a feel for their background and skill set, and at this point, they’ve had time to do their due diligence on the company and they can get some of their questions answered. 
• Steps 3-5: These are interviews across different team members. This is when the candidate meets with related functions and senior leadership across the board. 

• Step 6: This next step might be a take-home working session, like a case study, where a candidate can demonstrate their capabilities in action. 
• Step 7: This proposed final step would be meeting with a board member or following up with the CEO. 

Regardless of the exact process, the key is having more direct contact with the candidate in between each step. As the hiring manager, you shouldn’t meet with them for that first call just to disappear until it’s time for offer negotiation. Instead, try to have two or three one-off conversations on the side, whether that be via email or a quick phone call. Consider helping them prep for an interview, debrief with them after, or offer a product demo. 

We’re learning that candidates aren’t afraid to make a decision on opportunities within a two-week timeframe. Don’t feel that by condensing your timeline, you are rushing them to make a decision. And from your business’s perspective, if you have a crystal clear process and assessment criteria, you can get all the information you need on a candidate in those two weeks. 

How do you create a good test of skill that is not too overwhelming?

You need to find a balance between giving a task that is a good assessment of the skills that you’re looking for and being considerate of your candidate’s time. A lot of these assessments will instruct candidates not to spend more than a few hours on it, but every time I speak with someone who’s completing one of these tasks, regardless of their level, they share that they’re usually spending eight to 10 hours because they know that’s the amount of time it takes to complete the work that’s being asked of them. 

Some great alternatives to a traditional test of skill are holding a live brainstorming session or asking them to talk through some examples of past work they’ve already done. What’s important here is to not give a task that is going to be a turn-off to a candidate, where they know they’ll have to spend so much time on it that they withdraw from the process entirely. Be mindful that these people are also interviewing for other roles, and often still working a full-time job. 

Timing matters here too. If you layer this in too early before the candidate is fully sold on the opportunity, their appetite for it—and their effort—is going to be pretty low. 

What are the best converting close tactics you’ve seen once you’ve identified your ideal hire?

If it’s your dream candidate, you should have already been asking them how they’re feeling throughout the process and getting to know what’s interesting to them. Answer their questions and keep coming up with ways to get them excited. Maybe that’s setting up more meetings with the CEO or a specific person on the team that they’re really jiving with. 

We often see that talking to an investor or board member is really exciting for candidates, too. It’s a chance for them to get a different perspective and another opinion on the company. Utilizing the board and investor perspectives earlier in the process for strong candidates has shown a great deal of success. Leverage them to sell, focusing on the size of the opportunity and what it’s like to work with the CEO. These discussions will give your candidate a better idea of the competitive landscape, the size of the market, the product’s differentiator, and why now is the right time to join.