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Issue #37: People


James Costa

December 5 · Issue #37 · View online

A batch of thoughts, resources, and motivation from a friendly digital agency owner delivered every Monday at 6am ET.

People are the hardest thing to get right in running a business. Even 7 years in, I’m still learning about how under appreciated human resources (“HR”) is. Most owners don’t hire HR personnel early-on because they either can’t afford to, can’t connect them to a return on investment, or because it’s not something they think about. Instead, hiring is done by the owner.
Owners tend to be the folks doing the front-line work in the early days, so hiring ends up happening within their network. When that network runs dry (or the owner realizes the risk), they turn to job boards.
This sounds simple, but it gets complicated at three points:
  1. The owner is hiring for a role they haven’t done in a long time.
  2. The owner is hiring for a role they’ve never done.
  3. The owner is hiring for a role that they’ve done naturally / learned on the job, and don’t know how to transfer the knowledge.
To complicate things even more, it’s hard for the business owner to know when to hire so they can’t even be proactive. At a certain point, the owner realizes this and delegates this role to someone to manage (for us, it’s our Operations Manager (👋 Naomi!)). While this reduces the workload for the owner, ultimately it doesn’t make the hiring easier.
The latest example of how we haven’t gotten this right is our sales hire: I’ve been responsible for sales for the lifetime of the business, but know I need to step out of the role to grow the business (this is also the last role I need to transition out of, so it’s particularly stressful). We’ve been trying to hire someone for about a year now; we’ve iterated on our process, adjusted what we were looking for, increased how much we were willing to pay… and we still haven’t managed to crack it.
It might seem as though I’m approaching this as if I have some sort of solution, but I don’t. 
Here’s what I do know about People:
  • People are the biggest investment you’ll ever make in your business. It’s hard in a small team to quantify the return on investment from People, but it’s something you can feel when it’s done improperly. Similarly, you notice it when it’s done well. The investment you make in your people isn’t just monetary (i.e. salaries, education, training, etc), it’s non-tangible. It’s how you treat them, find them, and integrate them.
  • People needs to be a part of the culture, Valve has a handy employee handbook whereas they talk about hiring being the most important thing they do and that it’s everyone’s job. To take it a step further, including people as a part of the process (i.e. including them on interviews, having them mentor new hires, etc) and encouraging them to give feedback on peers is crucial (especially for catching red flags early).
  • People won’t be with you forever. This is something owners try to ignore. In an ideal world, everyone on our team would stay with us forever and we’d ride off on unicorns into the sunset, but we’ll leave those fantasies to the sci-fi writers. Realizing your people won’t be with you forever doesn’t give you the right to treat them as disposable, but it helps to mentally separate business and personal. I talk to my team about this candidly in the context of their current job being a springboard, and the importance of employers making their people better. We encourage hires who leave to wave our flag with us wherever they go, and we have an “alumni” channel in Slack for them to keep in touch (and for us to try and convince them to come back).
  • People have strengths and weaknesses. Understand them. Doing so will help you set everyone up for success.
  • When hiring for new roles, start part-time.
  • The problem with process is process.
  • Terminating people sucks. Not terminating people sucks more. I’ve been told I’m a good guy. As as good guy who also tries to see the best in people, it’s hard to not give people the opportunity to improve. As a good guy who wants to maintain his image as a good guy, it’s hard to fire people. Because of these traits, terminating people can be tough. But delaying the inevitable makes it exponentially worse. Pro tip: when you terminate people, pull up their job description and edit it with your fresh perspective on their role.
  • “Hire slow, fire fast” is bullshit. This might seem opposite of the previous point, but I wanted to address this often-discussed notion. I’m all for it, but don’t let this encourage a culture of giving up on people: not only are the optics bad from the team, but it also doesn’t leave room for learning.
  • Laying off people is soul-destroying. Last year we had to lay off two amazing people from our team. We were going through an extremely rough patch and it was the only way we could think of to get back to sustainable growth. Laying people off is unlike terminating people because when you do, you still have the stress of things not going well. There are two things I learned about laying people off (which I hope to never have to think about again): don’t make it about you / focus on them, and don’t let it happen in vein.
One of the most important things HR and People have taught me is that life goes on (or, as Dory from Finding Nemo says, “just keep swimming”). You just have to keep fighting for it, and understand it’s importance in keeping your business moving.
And, hey, if you’ve figured out the solution to HR please don’t keep the secret to yourself: let me know!
PS: If you enjoyed this week’s issue, I’d really appreciate your support sharing it. Whether it’s a forward, a Twitter post, or your writing me some theme song music for when I walk into places, it would mean the world.

What’s the Second Job of a Startup CEO?
Product Hunt’s Rise
“Do not hire a man who does your work for money, but him who does it for the love of it.”
– Henry David Thoreau
Bureau of Digital's Owner Summit
On Wednesday, I went to watch Toronto FC (Toronto’s MLS soccer team) play the Montreal Impact in the Eastern Conference Finals. It was a wild night and incredible game, but the highlight overall was when I found myself in the middle of a massive crowd marching towards the stadium that were letting off fireworks, flares, and chanting on the top of their lungs (my voice still hasn’t recovered). It felt like I was in the middle of a protest, and I caught some sweet video for you all.
As always, if you have any questions or I can help you in any way, all you have to do is respond to this email!
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