You hired them to speak up on day one

The newest person often sees the red flags first and says the least.

I joined a team that called itself empowered. Very quickly, I saw that almost every meaningful step still needed stakeholder approval, and each approval could turn into a veto later. I noticed the pattern early, but because I was new, I assumed I was missing context. That everyone else understood something I did not.

So I stayed quiet. Week after week went into aligning with stakeholders, reworking plans, keeping everyone happy. Nothing shipped to customers. When I hinted something felt off, the concern was easy to dismiss as newcomer impatience.

Soon after, the delays, vetoes, and confusion caught up with us. The team more or less fell apart.

The cost of staying quiet

I have since spoken to several people in similar situations. Almost all of them stayed quiet. Almost all of them regret it. Some shame themselves for it. They saw the signs, they wanted to speak, and in the moment some of them chickened out. Their words, not mine.

That silence is expensive.

It is easy to understand why it happens. You assume the others know something you do not. Your expertise feels like it does not quite apply yet. You tell yourself: observe first, get the full picture, then speak. There are real technical problems that need your attention right now. And sometimes you convince yourself it is about your relative seniority, or that you have not yet earned the standing to challenge how things work here. Sometimes that is even true.

We are good at rationalising away discomfort. That is not weakness; it is very human. I do not want to shame anyone for it.

But if you are reading this and recognising a moment where you stayed quiet and still think about it: do not beat yourself up too much. Use it. The fact that it still bothers you is a signal that your instincts were working. Next time you feel that pull, remember this. Practice is how you get there.

What you are actually hiring for

The team welcoming a senior hire often expects something specific: more output capacity. Someone who brings deep expertise, ships things, and makes the existing work go faster. That expectation is reasonable. It is often part of what happens.

But the most experienced people, the ones who have seen many teams and contexts, often deliver something different and more valuable. They see things the team has stopped seeing. Through genuine fresh perspective and creativity, they can expand outcomes rather than just output. What was previously not even imagined becomes possible. And this applies to any role, not just engineering.

When someone arrives from outside and names something as very wrong, it can feel like the worst version of imposter syndrome coming true. Perhaps we were not as good as we thought. Perhaps the processes, the agreements, the way things actually get decided, were never quite right. That is a genuinely hard thing to sit with honestly.

What helps is to remind yourself: you hired them for this. Radical improvements sometimes need someone willing to say the thing that everyone else has rationalised away. That is not a sign of your failure. It is what good hiring looks like.

Do not expect the signal to come in the form you imagined. It probably will not be a technical observation. More often it will be about processes, about how decisions are made, about the social fabric of how you work together. The sociotechnical layer. The newcomer might feel strange raising it: ‘Why am I even talking about this? They hired me for technology.’ But processes and technology are parts of the same system.

Embrace that feedback. Evaluate it honestly. That is hard work, and it needs to stay anchored to what the team actually needs.

What makes these people valuable is not only their technical ability. It is their capacity to expand what the team believes is possible. That can feel uncomfortable. That is also exactly why they are worth hiring.

If you are the new one

Say it. Strong opinions, stated plainly, team success first. You can be wrong. You are probably right about some of it. And even when you are wrong, the team that handles that honestly is the team worth being part of.

If you are welcoming someone

Make it genuinely safe to raise uncomfortable things. When a newcomer names something that feels off, your first job is to listen. Be prepared to radically reëvaluate. They are not making waves. They are doing exactly what you needed when you hired them.

Title photo by charlesdeluvio.