Choosing a Software Delivery Partner: 12 Questions to Ask

Answer these internally first so the conversation stays productive:

• What outcome matters most (speed, stability, cost control, modernization)?

• Who is the decision owner?

• What’s fixed vs flexible (deadline, scope, budget)?

• What systems/teams are dependencies?

The 12 Questions to Ask When Screening Your Software Developers

A) Delivery & communication (how work actually moves)

1) What’s your weekly delivery cadence? Walk me through a typical week.

Listen for: sprint rhythm, demos, stakeholder updates, how priorities get locked.

2) How do you keep stakeholders aligned when priorities conflict?

Listen for: one accountable product owner, escalation path, documented decisions.

3) How do you estimate work and communicate uncertainty?

Listen for: ranges + assumptions, how estimates tighten after discovery.

B) Scope & risk control (how you prevent chaos)

4) What’s your change-control process when scope shifts midstream?

Listen for: a lightweight “tradeoffs” mechanism (add X, remove Y), decision log.

5) What risks do you look for in the first 2–3 weeks, and how do you track them?

Listen for: integration, security, data migration, performance, stakeholder risk.

6) What does “done” mean in your process?

Listen for: acceptance criteria, QA, documentation, release readiness, sign-off.

C) Team quality & accountability (who is on the hook)

7) Who will actually be on the team, and how stable is that team?

Listen for: named roles, seniority, continuity plan, limited handoffs.

8) Who is accountable day-to-day, and how do I reach them when things get urgent?

Listen for: clear owner (PM/Delivery Lead), response expectations, escalation path.

D) Engineering fundamentals (security, integrations, reliability)

9) How do you handle environments, access, and security basics?

Listen for: least privilege, auditability, scanning, secrets management, discipline.

10) How do you manage integrations and dependencies on other systems/teams?

Listen for: dependency mapping, early spikes, interface contracts, shared timelines.

E) Proof & post-launch (evidence you can trust)

11) After launch, what does support look like?

Listen for: triage flow, incident handling, warranty period, ongoing improvements.

12) Show me a similar project and tell me the tradeoffs you made. What changed midstream?

Listen for: real stories, what went wrong, what they learned, how they adapted.

Fast screen (use these early if you want to qualify quickly)

If you only have 10 minutes, ask these first:

• #1 cadence

• #4 change control

• #7 real team + stability

• #10 integrations/dependencies

• #12 proof + tradeoffs

Simple scorecard

Rate each answer 1–5:

• Specificity (real process vs buzzwords)

• Ownership (clear roles and accountability)

• Realism (tradeoffs acknowledged)

• Communication (clear, structured, easy to follow)

Rule of thumb: If they can’t explain their process clearly, they won’t run it clearly.