Choosing a software development partner is one of those decisions where the cost of getting it wrong shows up months later, long after the contract is signed and the budget is spent. By then you have a codebase you cannot maintain, a team that quietly swapped out the senior engineer you were sold, and a launch date that keeps sliding. The pitch was great. The delivery was not. Most of the damage traces back to questions nobody asked in the first three meetings.
In 2026 the choice comes with a new wrinkle: nearly every agency now says it is "AI-powered," and that phrase means everything from a disciplined team using AI to ship faster to a shop letting a model write code nobody reviews. The good news is that the questions that expose a real partner have not changed much, they have just gained a few. Here is what to actually ask, and what the answers tell you.
Judge how they respond to your problem, not their portfolio
The first tell is what happens when you describe your project. A partner worth hiring slows down. They ask about your business goal, your users, and what happens if the thing does not ship on time. They push back on parts of your plan and suggest alternatives, even ones that shrink the project. A team that agrees with everything and quotes a price on the first call is optimizing to close the deal, not to build the right thing. That instinct, sometimes the right call is to not build at all, is the same one behind every honest build vs buy conversation, and you want a partner who will have it with you.
Ask who actually does the work
The oldest trick in agency sales is the senior team in the pitch and the junior team on the code. Get specific:
Who works on this day to day, by name? Ask to meet them, not the account manager.
Will that team change partway through, and how do you handle the handoff?
Is any of this subcontracted further, and to whom?
You are not being difficult. You are checking that the people who impressed you are the people who will build your software. If a partner will not name the team, that is your answer. For smaller companies without an in-house technical lead, this is also where a fractional CTO earns their fee, sitting on your side of the table to read these answers for you.
Pin down how they use AI
This is the 2026 question, and vague answers are a red flag in both directions. A team that uses no AI is leaving speed on the table; a team that uses it carelessly ships code no human understands. Ask directly:
Which AI coding tools does your team use daily, and for what?
What is your human-in-the-loop review process for AI-generated code?
Who is accountable when AI-written code has a bug in production?
The answer you want describes AI as a tool their engineers drive and review, not a replacement for judgment. We wrote about running AI coding agents on a real team and the discipline that keeps AI-written code safe in production; a good partner will recognise the problem before you finish the question.
Ask to talk to a past client, not just see a logo
A wall of client logos proves nothing. Ask to speak to a real reference on a project close to yours in size and complexity, not their best-ever showcase. Ask that client one question: what went wrong, and how did the team handle it? Every real project has a rough patch. How a partner behaves in it is the whole thing.
Nail down ownership, process, and what "done" means
Two contract details cause more grief than any technical decision. First, ownership: you should own the code, the repositories, the accounts, and the infrastructure, in writing, from day one. If leaving a partner means losing access to your own software, you do not have a partner, you have a hostage situation. Second, process: how long are sprints, how do you see progress, and how are changes and incidents handled? You want short cycles and something working to look at every couple of weeks, not a six-month silence ending in a big reveal.
Match the model to your project
There is no single best partner, only the right fit for your stage. A local agency, a nearshore team, and a global outsourcer each trade cost, timezone, and communication differently. For European companies, nearshoring has become the default middle path, and we broke down why in the Portugal guide. Whatever the model, price the whole thing honestly, including maintenance after launch, which most first-time buyers forget until the first invoice lands. Our custom software cost guide walks through where the money actually goes.
The partner you want is the one who asks harder questions than you do, names their team, uses AI like a professional tool, and puts your ownership in writing. If that is the kind of team you are looking for, tell us what you are building and we will tell you honestly whether we are the right fit, or point you to who is.
