Hiring for problem-solving over skillset builds stronger engineering teams

When Adam Wachtel took over Click Boarding, he didn't lead with a skills checklist.

4 min readInfoQ
Hiring for problem-solving over skillset builds stronger engineering teams

Adam Wachtel's argument in the podcast cuts to a tension every engineering leader recognizes: the instinct to hire for a known stack versus the long-term cost of a rigid team. He's not saying skills don't matter. He's saying that in a crisis, or in any environment where the problem set is shifting, a person's ability to reason through ambiguity will outperform a specific framework every time. That's a hard sell in a market that still writes job descriptions like shopping lists, but it's also the only approach that scales when the tooling changes underneath you. If you're building a team that's meant to last past the next feature cycle, you're not looking for someone who already knows your exact API. You're looking for someone who can look at a broken system and figure out where to start.

Here's where the conversation gets more interesting, and more uncomfortable. Wachtel describes turning around a platform and team in crisis, and that context matters. When you're in firefighting mode, you don't have the luxury of a long onboarding curve. You need people who can think on their feet, communicate under pressure, and adapt to new information quickly. That's not a personality quirk; it's a survival mechanism. But the deeper point is that this principle doesn't just apply to rescue missions. It applies to the normal, unglamorous work of maintaining a SaaS product. The teams that get stuck are rarely the ones with the weakest technical skills. They're the ones where people are too afraid to ask questions or too rigid to consider a different approach. If you're hiring, that's what you're screening for. You're not looking for the person with the most impressive GitHub history. You're looking for the person who can sit in a room with a vague problem and not panic.

The conversation around AI and team size is where Wachtel's view becomes genuinely forward-looking. He's not predicting the end of SaaS or the death of the engineer. Instead, he's observing that AI is changing the composition of teams, and that has immediate practical consequences for how you hire and structure your organization. If AI handles more of the boilerplate, the premium shifts to judgment, product sense, and the ability to delegate to a tool effectively. That doesn't mean smaller teams are always better. It means the ones that thrive will be the ones that can absorb new capabilities without losing their human center. For our readers, the takeaway is concrete: stop hiring for the role you think you need today and start hiring for the person who can grow into the problems you haven't solved yet. Ask yourself what you'd do if your core stack became obsolete next quarter. If your team can't answer that question, the issue isn't their skillset.

The specific detail to watch is how Wachtel measures success in that kind of environment. He's not talking about hiring for personality as a feel-good exercise. He's talking about it as a risk mitigation strategy. Personality, in his context, is really a proxy for resilience and intellectual honesty. The open question for leaders is whether they can institutionalize that standard without falling into the trap of hiring for culture fit, which often just means hiring people like yourself. That's the line to walk. The team that wins will be the one that can honestly say, "We don't know, but we'll figure it out," and mean it. That's the quote to take with you.

From InfoQ

In this podcast, Shane Hastie, Lead Editor for Culture & Methods, spoke to Adam Wachtel, CTO at Click Boarding, about hiring for personality and problem-solving over pure skillset, turning around a platform and team in crisis, and how AI is reshaping team size and composition without ending SAAS.

Read the original at InfoQ