“If only we hired a person to do this, things would be so much easier.” I think this is a thought that’s crossed my mind many times over the years. And naively, I went ahead and usually hired someone.

Even recently, I heard myself talk this way when thinking about our business development efforts. Sei-Wook and I have been hoping to find someone to offload some of the sales activities that we do, including qualifying inbound leads and doing more outbound prospecting. The thought of nabbing a smart and driven individual to take on this work was very appealing, especially as the two of us have been mired in never-ending business development tasks. Why not post up a job listing and get the process moving?

One lesson I’ve learned from hiring (and firing) at Barrel is that it’s extremely important to understand that hiring someone doesn’t necessarily make all problems go away. In fact, the hiring may even be a distraction, especially if you expect that the new hire will magically make the problems disappear.

I’ve been toying with a checklist/questionnaire to help me vet my need for a new hire and, if absolutely necessary, then to plan for their hire. While I currently ask parts of these on an on-going basis, I think codifying them into some kind of framework will prove useful. I’ve written these down with a couple of things in mind: a) that the organization is one that is growing and doesn’t have all its departments and structures rigidly fixed and b) that the new hire could be for a position that does not formally exist in the organization.

New Hire Questionnaire

• What is the role that we’re hiring for?
• What is the problem that the new hire will help to solve?
• If we could not hire someone at all, how would we go about solving this problem? What would it cost us in terms of time, existing resources, and money?
• How will we ensure that the new hire is a great cultural fit, especially if this person is hired for a position/department that doesn’t yet exist?
• What is our expectation for the new hire’s impact in the first 3 months? The first 6 months? The first year?
• How will this new hire be trained? Who will lead the training and how will the training be structured?
• If this is a brand new position, how will we empower the new hire to develop and institutionalize the position?
• Who will the new hire report to? To what degree and how often will this person communicate with other members of the team?
• How will this person fit into our existing workflow? What will stay the same and what will have to change?
• How will we evaluate the performance of the new hire, especially if this person’s position/department has no precedent? Who will review this person and against what metrics?
• If the new hire is successful, what does that look like? What will be different?

When I think about all of these questions together, what I basically see is my company’s need to build capacity in order to hire someone. I need to be sure that I have this person’s role mapped out thoroughly, at least to the degree that on day one, the training and assignments are clearly laid out. I have to examine my organizational structure and think about how the new hire will impact the way we work and communicate as a team. I need to think through not just about the short-term fixes this person may alleviate but also what the long-term benefits of having the new hire will mean for the company.

For the most part, we’ve been extremely lucky at Barrel to have hired some really talented and smart people. When I think about the misses we’ve had, they’ve usually come as a swift reaction to something unpleasant: an unexpected departure, a reoccurring problem that I didn’t want to deal with, or the hope that a particular individual could help us overcome an inadequacy and raise us to a new level. For new hires, these instances have resulted in a toxic environment characterized by unrealistic expectations, little guidance, hardly any training, and confusion about their place in the organization. In effect, they’ve been set up to fail. I can only attribute that to my own inexperience, naiveté, and laziness. But hopefully, by taking my time and being thorough, this is an area that I can really strengthen with a solid system that puts the brakes on hasty quick-fix decisions.