Hiring a creative project manager is a judgement call. CVs all look similar. Here are seven questions that separate the people who run projects from the people who attend them.
Ask these in the first conversation. The answers tell you everything.
1. Tell me about a project that went wrong
Everyone has one. What matters is what they did. Did they spot it early? Did they tell the client honestly? Did they fix the process so it didn't happen again?
Red flag: 'I've never really had one go wrong.' They've either never run anything difficult or they're not being honest. Neither is good.
2. How do you handle feedback going in circles?
This is where creative projects die. Good answer: structured rounds, named decision makers, written feedback, and the willingness to say 'we need a decision by Thursday.'
Bad answer: 'I just keep chasing.' Chasing isn't a process.
3. What do you do when the client wants something that will hurt the outcome?
This tests whether they think or just execute. A good creative PM pushes back — respectfully, with reasons. 'That change will weaken the concept because...' They protect the work, not just the timeline.
A PM who says 'the client's always right' will deliver exactly what was asked and none of what was needed.
4. How do you keep brand intent alive through a long build?
Most PMs manage tasks. The good ones guard the strategy. Listen for: revisiting the brief at milestones, challenging decisions against the original intent, keeping the 'why' visible when everyone's focused on the 'what.'
If they look confused by the question, they manage timelines, not outcomes.
5. What's your process for the first two weeks?
You want specifics, not vibes. Stakeholder mapping, brief validation, plan with milestones, risk list, communication rhythm. A PM who can't describe their onboarding doesn't have one.
6. How do you say no?
Scope creep, extra rounds, 'just one more thing' — it all needs a no, or at least a 'yes, and here's what it costs.' Listen for directness. Evasive answers here mean evasive delivery later.
7. Why creative projects, specifically?
Creative delivery is different from IT delivery or construction. It needs comfort with ambiguity, respect for the craft, and judgement about quality. If they fell into it by accident and stayed by inertia, keep looking.
You want someone who chose this — who understands that shipping creative work on time without killing it takes a specific skill.
What I'm listening for
Honesty about failure. A real process, not just personality. The courage to push back. Brand thinking alongside delivery thinking.
That's how I work. Certified ScrumMaster, 17+ years, 330+ projects. I think in brand and deliver like a PM.
Working with Avy
Need someone to get your project over the line? Avy embeds with teams as a contractor — project management, delivery leadership, or an extension to your marketing function for creative work. Book a call or send an enquiry to start the conversation.
Want your team aligned fast? He runs paid brand workshops. Working sessions, not slide decks — the room leaves with decisions.
Need someone to get your project over the line?
Project delivery support for brand, digital, and creative teams that need clearer direction and smoother progress.