Project management in hybrid and remote work: why most projects fail

Executive overview

Three in five projects fail — and that was before remote work made coordination harder. Phil Simon argues that the shift to hybrid work hasn't created new problems so much as it has amplified existing ones: unclear roles, mismatched tools, and poor written communication.

His book offers nine prescriptions to improve odds of success — not guarantees, but statistically sound plays. The core tools are simple: agree on tech early, run pre-mortems, set role clarity via RACI, and invest in writing quality.

Most project failures trace back to people problems, not technical ones.

Why projects break bad

• Three out of five projects fail even in synchronous, in-office environments
• Root cause analysis consistently leads back to human factors: unclear expectations, poor communication, ignored documentation
• Remote and hybrid work amplify cognitive biases — you can't read the room when half the room isn't visible
• Silent stakeholders are especially dangerous: they disengage, then surface grievances late
• Asynchronous communication turns five-minute clarifications into five-day delays

Agile vs. waterfall: choosing the right method

• Agile (e.g. Scrum) works for iterative products where imperfection is recoverable — a broken app update won't kill anyone
• Waterfall (phase-gate) suits high-stakes projects where the thing must work from launch — drugs, aircraft, regulated systems
• Both methodologies suffer from the same underlying people problems regardless of approach

Settle early on the tech

• Tool fragmentation kills projects: if teammates use different platforms, messages fall through the gaps
• Agreeing on tools upfront is necessary but not sufficient — you must also enforce that agreement
• Sunk cost fallacy keeps teams locked into software everyone hates; switching mid-project is painful but often correct
• Vet partners by the tools they use — a firm that runs on email alone signals higher project risk
• Automatic (Automattic) tests hires with a small paid project before committing; the same logic applies to vendors

RACI: clarifying who does what

• RACI (Responsible, Accountable, Consulted, Informed) prevents the common failure where someone expected to be consulted finds out they were only informed
• Especially critical in async work where misunderstandings compound silently across days or weeks
• Defining RACI at project start is a low-effort intervention with outsized impact

Pre-mortems over post-mortems

• A pre-mortem assumes the project has already failed, then asks why — before it happens
• Hertz spent $32 million on a website and app in 2016 that failed catastrophically; a pre-mortem might have surfaced the risks early
• A pilot phase (e.g. $200K scoped prototype) stress-tests the team and tools before full commitment
• Post-mortems capture lessons after the damage; pre-mortems prevent it

Writing as a project management tool

• In hybrid work, written communication carries more load than ever — you can't tap someone on the shoulder
• Poor writing multiplies message volume: unclear messages generate 13 follow-ups instead of one or two
• Amazon and Automattic have brought in writing coaches to raise baseline quality across teams
• Using tools like Slack or Teams only helps if people can write clearly within them; the tool doesn't fix the message

The case for hybrid (not fully remote)

• ~92% of employees report being as productive remotely; ~96% of managers agree
• Flexibility on where and when to work is now a baseline expectation for most knowledge workers — not a perk
• Fully remote removes the serendipitous relationship-building that makes teams trust each other
• In-person time doesn't need to be constant — twice-yearly gatherings can serve the bonding function
• Proximity bias (rewarding visible presence over actual output) is the failure mode of mandated office return

What unofficial project managers can do now

• Most people are de facto project managers whether or not they hold the title — freelancers, side hustlers, and team leads all qualify
• Start any project by aligning on tools, channels, and role expectations before any work begins
• Use a RACI matrix even for small projects; it takes minutes and prevents expensive misunderstandings
• Run a pre-mortem in the kickoff phase — assume failure and ask why
• Treat writing quality as a project infrastructure issue, not a soft skill