Decoding the disconnects that keep great teams from working well together
If you’ve ever sat in a room where a startup founder, a brand manager, and an agency account lead try to solve a problem together — you know it can get messy.
Same goals, different vocab.
Same intent, different timelines.
Same sprint, different expectations.
I know this, because I’ve been all three.
- I’ve built and scaled digital teams inside brands
- I’ve worked agency-side, across big retainers and razor-thin timelines
- I’ve helped founders who needed traction yesterday and had budget for tomorrow
And what I’ve learned is this:
Most friction comes not from bad people — but from misaligned perspectives.
Here’s what each camp needs to understand about the other.
1. What brands don’t understand about agencies
- Agencies don’t sit around waiting to “wow” you.
They’re often stretched across multiple accounts, firefighting for others while planning for you. - Strategy takes time — but turnaround doesn’t wait.
If you don’t give them a tight brief and quick feedback, expect diluted output. - Good agencies don’t just “execute.” They think.
But they need to be trusted to challenge you — not just tick boxes.
👉 Tip for brands: Treat your agency like an extension of your team, not a vendor. Share context, involve them early, and respect their process.
2. What agencies don’t understand about brands
- Most brand-side marketers are drowning in internal alignment work.
They’re not slow — they’re stuck between product, sales, leadership, and finance. - Every campaign has internal politics you don’t see.
A rejected idea might have nothing to do with creativity and everything to do with timing. - “Just one more revision” might cost you 2 days, but save them a leadership headache.
👉 Tip for agencies: Empathise with internal constraints. Ask better questions to uncover real blockers — and help your clients look good internally.
3. What startups don’t understand about agencies and brand teams
- Agencies are built for process. Startups are built for speed. The two must meet halfway.
Chaos is not a vibe agencies can sustain. - Brand teams can’t reinvent the wheel every week. They need rhythm, not reactive mode.
Your “fast experiments” can break entire systems if not scoped right. - You may not need a brand film — you may need working onboarding, clarity on positioning, or better CRM.
Hype without foundation kills trust.
👉 Tip for founders: Don’t expect world-class execution from half-baked briefs. Slow down to scale smart.
4. What everyone misunderstands about startups
- They’re not disorganised. They’re evolving.
Most startup teams are writing the playbook while running the play. - Their constraints are not excuses — they’re their reality.
Asking for 50 creatives a month from a 2-person team isn’t strategy. It’s fantasy.
👉 Tip for everyone else: Be partners, not passengers. Help startup teams prioritise. Bring clarity, not just deliverables.
So where does Ask Maddy come in?
After two decades of watching this dance, I realised what’s missing isn’t talent or tools — it’s translation.
- Brands need better briefers and thinkers.
- Agencies need better context and access.
- Startups need systems and sanity.
Ask Maddy was built to bridge these gaps — by bringing the right mix of strategic structure, delivery design, and people alignment into the room.
If you’ve ever said “this should’ve worked, but didn’t,” maybe what you needed wasn’t another team — but a translator.
TL;DR
Agencies, brands, and startups are all trying to win — but they often speak different languages.
Want better work, faster outcomes, and fewer escalations?
Understand each other.
Work like partners.
And when in doubt — just Ask Maddy.