I wish that advice was staring me in the face, every day, particularly when we were just starting Sentry.

Recently I dumped some thoughts on Twitter (presently known as X) around hiring, thoughts that are generally triggered by whatever is happening in my day-to-day. This is an attempt to make that a little more coherent and useful to other founders and leaders. It’s the weekend, so this ones going to be brief, but hopefully you’ll take away something of value from it.

Whether you’re starting a company, or you’re in a leadership position at another company, you likely need more focus around your approach to hiring. We don’t talk enough about what compromise creates in terms of consequence when it comes to your team. You see, just like many things you do in life, you need conviction around a methodology of hiring if you’re going to succeed. My approach has always been to focus on hiring people who can do the job at hand, have the industry experience I think will be value-add, and less on the side of trying to train or mentor folks who don’t. The tradeoff I make with that is I have to be willing to be more competitive in the compensation market, and more compelling in the job specs. I have a clear objective when it comes to hiring, as do many others, but then why do we fuck it up so much?

I want to take a moment to address what I mean by failing at hiring. The issue generally comes down to hiring someone into a position that they cannot succeed at. That might be because the hiring manager themselves didn’t understand the job qualifications, the qualifications were too fuzzy (or too dynamic) for the hire, or in the rare case it might even be the candidate pulled a fast one on you to get the job. Ultimately it simply means you hired the wrong person for the job.

The universal truth you hear from any leader who will be honest with you is that “Fire Fast” isn’t true enough. Early on at Sentry I attended an event with a number of seasoned CEOs and leaders, including one of whom worked under two sitting US presidents. They will tell you the same thing I’m telling you today: everyone makes the mistake of hiring the wrong people, and then failing to terminate the relationship in earnest. We do this because we want to give people a chance - to coach them. We do this because we want to avoid conflict. We do this because we lack confidence in our decisions. Then, when we do this, we create a mess of problems for organizations, sometimes even dooming them.

This is where the Fire Fast mentality comes into play, and anyone will happily nod along and say “yeah stop hiring shitty people”. The problem with leaving the conversation there, is often people fail to address the problems that got us into those situations. What would you have done differently to avoid hiring the wrong person? It’s a pretty straight forward question, but it’s not one that’s always easy to answer. There are however some really common scenarios that I’ve lived through, so I want to give some direct-from-the-source tips today.

1. Trust Your Gut. In every single scenario where I wasn’t quite convinced the hire was right, where I had that gut feeling, they weren’t. It may not be scientific, but it’s effective. I now never hire someone if I have that sinking feeling they might be the wrong hire. I might lose some great candidates, but I’m not playing a dice game here.

2. Don’t Compromise. This is probably the most common mistake I see. Someone comes up with a weak excuse that they are time boxed on finding the right candidate, they haven’t found them, so they hire someone from the existing pool that is the best they can find. Spend the extra time to find the right person, as it saves you time in the long run.

3. Culture Trumps Experience. I’ve gone down the road of hiring folks who “have the experience” before, and sometimes it works, but often what happens is you find a candidate you really like and pass on them. Someone who fits the personality of your company, think’s similar to you, a great fit. Oh, except they’ve never done the job you are asking them to do before. That’s fine! You’re hiring someone capable, and if you think them capable of doing many parts of the job, you should think them capable of doing parts that are new to them.

4. Stop Listening to Bankers. Lots of people want to whisper in your ear about what you need. Sometimes their advice is valuable, but often it is not. Do not trust folks who haven’t done the job with their advice. Treat them as anyone else you’d meet on the street advising you, and frankly, use your brain about what is and isnt best for your organization. The same advice goes for someone like me - just because I have experience doesn’t mean you should take my advice at face value. An almost objective freebie though: don’t hire a C-level executive when you’re a 20 person company. That’s fucking stupid in 99% of scenarios.

You’re still going to make mistakes, particularly if you’re outside of your comfort zone. When you’re starting a company you are often hiring for roles that you’ve not done yourself. Your job is not to hire someone and trust that they’re an expert, but to hire someone who you believe is going to be capable, and verify along the way (and quickly!). That inevitably means you’re also going to be left back where we started as you’re still going to make mistakes. You’re back to dreading the go-to advice: Fire Fast. That may seem cruel, but its worse for you, them, and most importantly, everyone else on your team if you don’t do it.

I want to leave you with a final parting story about the kind of thing that can happen if you don’t correct mistakes quickly.

Early in Sentry’s life we didn’t quite know how the business was going to work. When we started trying to build out that function, we had to make a gamble on the type of person we wanted to help run it. We made two mistakes in this gamble: first, a person is an organization. You are betting on a methodology, and people rarely change theirs. Second, we wrongly made a bet on someone with more seniority, over someone who was scrappy and could help us figure out where we were going. Worse here, when you’re hiring a traditional executive, its easy to forget they’re often not the builder themselves. You’re hiring them because you want them to run (and build!) an organization. That means you’re hiring them with the express intent to hire and build other leaders in their organization. In our case that was the beginnings of sales, marking, and more traditional customer services. Not a single one of those functions ended up being successful for us.

They didn’t succeed for a variety of reasons, mostly because they were not the right approaches to where the business was going. The issue though isn’t that our approach was unsuccessful, the issue is we had built out an entire organization of people who were potentially not the right people for the job. What I mean in our case is that we had built out a traditional sales organization when Sentry was anything but a traditional enterprise company. Instead of investing in brand marketing (what we do these days), we invested in a small pool of traditional sales and marketing hires with your status quo approach of what people think “Enterprise” looks like. We were (and still are not) a company that operates that way. I knew it then, but I lacked the confidence to trust myself. Worse, I listened to people who didn’t know what they’re talking about.

It took us a couple years to truly hold ourselves accountable and admit that it wasn’t working, and by that point those functions were staffed up with people who were performing jobs we didn’t need, with leaders who were ineffective. The resulting outcome was us replacing every single leader in the go-to-market organization and adjusting those departments towards a strategy that made sense for us. It wasn’t something we enjoyed doing, but it was a valuable learning lesson for myself and the rest of the team. It also cemented many of the values we hold today about how our business works, and is one reason why I am so bullish on Sentry’s atypical business model.

So we’re back to Fire Faster, but Hire Better. Both are critical, but need more focus on the latter in our industry, avoiding the obvious mistakes. Pair that with peers and mentors you trust, who will push you to make the hard decisions when things aren’t working. This is increasingly important with the most senior people on your team, as they have outsized influence, and one bad hire left to their own vices can translate to an entire organization that is misaligned, or worse, not needed. The situations are never easy, but you only harm yourself, your organization, and potentially your entire business by not making them.