Manager: Hire Carefully, Fire Quickly

Three weeks only….I had to fire her I screwed up a sales hire once. I had been trying to fill an Account Executive role for a while. The hiring process went great—multiple interviews, one with the team, and even a board member got involved. The candidate crushed every round. Confident, articulate, and seemingly a great fit. But then she started. And it went downhill fast. She struggled to communicate with the team. She was a slow learner. Worst of all, she didn’t understand basic tools—she didn’t even know what Google Drive was!!!! Where did I go wrong? I didn’t test for the things she ultimately failed at. We focused on sales acumen, presentation skills, and cultural fit. But we didn’t test for adaptability, tech fluency, or how quickly she could ramp up. She interviewed like a pro but couldn’t deliver where it mattered. It was a painful but clear lesson: your hiring process needs to test for the actual skills and traits the job requires. But the hardest part? Letting her go. It became obvious within three weeks that it wasn’t going to work. She wasn’t improving, and the team was frustrated. That led to my second big lesson: fire fast. The moment you realize it’s not a fit, act. Waiting only delays the inevitable and steals time you could be using to find the right person. That experience forced me to tighten up my hiring process—adding more practical assessments and testing for the real, day-to-day skills that make someone successful in the role. Key takeaways: 1. Test for what actually matters. Don’t assume a great interview = great hire. 2. Fire fast. The longer you wait, the more damage it does. Have you ever made a bad hire? What did you learn from it?

I have hired people out of desperation more than once, and it has never worked out. The old leadership rule is hire slow, fire fast - take your time finding the right people, and move quickly when someone is not working out. But when you are short-staffed or convinced you can make a mediocre fit work, it is easy to rationalize hiring someone you know is not quite right. I have made that mistake, and what happens is predictable - one person who does not fit the culture changes the energy in an entire room. The rest of the team starts working around that person - avoiding them in the hallway, keeping conversations surface-level, and stopping themselves from speaking up in meetings because they do not want to deal with the negativity or friction. All that energy spent avoiding one person adds up fast, and it costs more than leaving a role unfilled ever would. We can teach title insurance, coding, development, processes, and systems - after all, technical skills are learnable. But we cannot teach someone to be innovative, honest, collaborative, or respectful, and we cannot teach someone to care about the work or show up with a positive attitude. Culture fit either exists or it does not, and that is exactly why we prioritize culture over technical skills during hiring. A technically brilliant person who drags down the team costs more than they contribute, while a less experienced person who fits the culture and wants to learn will deliver more value over time. The hard part of following the hire slow, fire fast rule is recognizing when you made a hiring mistake and acting on it quickly. I have kept bad hires for months, hoping the situation would improve, and every time, the team paid the price for my hesitation while I avoided making a hard decision. Now, when I see the signs that someone is not working out, I move decisively. Firing someone is never easy, but I owe it to everyone else who is doing great work and does not deserve to have their energy drained.

When I started Arcade, overnight I went from someone who had never hired anyone to constantly thinking about building high-performing teams. These are a few things that I've learned along the way. I believe that great people solve 80% of problems (and build great product and great revenue), and can significantly alter the trajectory of your company. The inverse is true: hiring the wrong people can cause damage that can take years to unwind. 𝟭. 𝗛𝗶𝗿𝗲 𝘀𝗹𝗼𝘄, 𝗳𝗶𝗿𝗲 𝗳𝗮𝘀𝘁: Being very thoughtful about WHO to hire is critical. Usually, a pain slowly emerges within the daily workflow. Solving the problem yourself is really important as a hiring manager. If you're also not doing the job frequently enough, it's a signal that it's not really a full-time role. For example, I did not hire our first sales rep until we were at $800k in ARR. Being fast to part ways is important to unwind any potential damage. While firing fast is never ideal - and should be avoided by putting in the upfront work during the interview process (see below) - there's only so much that you can learn until they're in the role. Usually, if you have questions after the first 90 days, and not improving after at least two rounds of feedback, then the person is likely not the right fit. 𝟮. 𝗕𝘂𝗶𝗹𝗱 𝗮 𝗿𝗶𝗴𝗼𝗿𝗼𝘂𝘀 𝘀𝗰𝗼𝗿𝗲𝗰𝗮𝗿𝗱: Write down the attributes and qualities of who you want to hire, and a rating system across each attribute for each interview. This needs to be super specific to the role, and interviewing the best of the best in this role can give great inputs into designing the scorecard. This also helps keep the bar high across the team and avoid changing your mind after meeting someone. 𝟯. 𝗣𝗮𝘆 𝗮𝘁𝘁𝗲𝗻𝘁𝗶𝗼𝗻 𝘁𝗼 𝗶𝗻𝘁𝘂𝗶𝘁𝗶𝗼𝗻: Some people are better at reading people than others. While interviewing, pay attention to every signal at the potential cost of over indexing - I've picked up on issues. Typos in emails? Not going to work. Late to interviews? If they're late to interviews, why would they be on time in the role? Rude to the waiter during lunch? Matter of time before they will treat your team the same. Blaming everyone else but themselves for past mistakes? They'll likely say the same about you when the next challenge comes. If there's a doubt about a person, don't hire. 𝟰. 𝗜𝗻𝘃𝗲𝘀𝘁 𝗶𝗻 𝗼𝗻𝗯𝗼𝗮𝗿𝗱𝗶𝗻𝗴 𝗮𝗻𝗱 𝗰𝗹𝗲𝗮𝗿 𝗴𝗼𝗮𝗹𝘀: This step is glossed over too often, but if you bring in top 1% talent and don't give them context or upfront education, they are not set up to succeed. Studies have shown that rigorous and thoughtful onboarding can extend retention by 2x. I've learned a lot over the years and believe that learning to hire well is one of the most, if not the most, critical part of team building.

Hiring is guessing. Promoting and firing is knowing. We spend weeks agonizing over hiring decisions—interview rounds, reference checks, culture fits, gut feelings. And we should. Because hiring? That's educated guessing at best. You're betting on potential. On resumes and rehearsed answers. On chemistry in a 60-minute conversation that's supposed to predict years of performance. But promoting? That's different. You've seen them in the arena. You know how they handle pressure at 4pm on a Friday. You've watched them navigate conflict, miss deadlines, exceed expectations, lift others up (or not). Promoting isn't guessing—it's recognizing what's already there. And firing? Firing is the clearest data you'll ever have. When someone isn't working out, you know. Your team knows. They probably know. The only question is how long you'll pretend the data isn't screaming at you. This is why "hire slow, fire fast" isn't just catchy advice—it's survival. Take your time hiring. Interview more people. Ask harder questions. Sleep on it. Because once they're in, you're committed to giving them a real shot. But when it's not working? Move fast. Not cruelly—never that. But decisively. Prolonging a bad fit helps no one. Not them, not the team, not you. The best leaders I know treat hiring like dating and firing like a diagnosis. One requires caution and optimism. The other requires clarity and speed. Your team's performance isn't just about who you bring in. It's about how quickly you're willing to admit when you got it wrong.

Everyone wants to talk about hiring. Almost nobody wants to talk about firing. Both are your job. Hire the right people. Coach them. Push them harder than they would push themselves, until they see their potential is far bigger than they thought. Then watch closely. Because as the org grows, some people grow with it and some don’t. Some live the culture and some quietly drift from it. The mistake most founders make is waiting. You see it early, you feel it in your gut, and you give it another quarter because the person is good and you like them. That quarter costs you more than the exit ever would. So give the feedback fast. Direct, specific, uncomfortable. Most people rise to it and surprise you. Some can’t, and the kindest thing you can do is be honest about that early, not late. And as the org grows, reporting lines change. Not everyone can report to you. Hierarchy exists so younger folks get the guidance they need. But the feedback stays direct. Across every level. No layers softening it on the way down. The hiring builds the team. The firing protects it.

Great CEOs aren't great because they hire well. They're great because they fire fast. Most founders get this backwards. They spend months perfecting their hiring process. Then they spend years tolerating someone who's destroying their culture. I've watched it happen dozens of times. A founder knows in their gut someone needs to go. They wait. They coach. They give "one more quarter." Meanwhile, the damage compounds. 𝗧𝗵𝗲 𝗯𝗿𝘂𝘁𝗮𝗹 𝘁𝗿𝘂𝘁𝗵: By the time you're sure someone is a bad actor, your team has known for months. 𝗛𝗲𝗿𝗲'𝘀 𝘁𝗵𝗲 𝗳𝗿𝗮𝗺𝗲𝘄𝗼𝗿𝗸 𝗜 𝘂𝘀𝗲: 𝟭. 𝗧𝗵𝗲 𝗧𝗲𝗮𝗺 𝗧𝗲𝘀𝘁 Are your best people avoiding this person? Are they asking to switch teams? Are they leaving? Your A-players will tell you who the problem is. Not with words. With their feet. 𝟮. 𝗧𝗵𝗲 𝗘𝗻𝗲𝗿𝗴𝘆 𝗧𝗲𝘀𝘁 Does the room change when they walk in? Do meetings feel heavier? Does the team seem relieved when they're out sick? Culture is contagious. Bad actors infect everything they touch. 𝟯. 𝗧𝗵𝗲 𝗦𝗲𝗰𝗼𝗻𝗱 𝗖𝗵𝗮𝗻𝗰𝗲 𝗧𝗲𝘀𝘁 You gave feedback. Clear, direct feedback. Did anything actually change? Or did they just get better at hiding it? Bad actors don't reform. They adapt. 𝗧𝗵𝗲 𝘂𝗻𝗰𝗼𝗺𝗳𝗼𝗿𝘁𝗮𝗯𝗹𝗲 𝗺𝗮𝘁𝗵: Every week you delay costs you: • Your best people's trust • Your culture's integrity   • Your own credibility as a leader The founders who build lasting companies understand this: Hiring is about potential. Firing is about protecting what you've already built. One bad actor doesn't just hurt performance. They give your entire team permission to lower their standards. Fire fast. Your team is watching. #Founders #Leadership #Startups #Hiring #venturecapital