Ever noticed how planning an IT project feels a bit like organising a family or group holiday? Flights, transfers, accommodation, excursions… there’s always that one wildcard cousin who forgets their passport or someone convinced that “it’ll all work out” without an itinerary.
And just like trips can go sideways if expectations aren’t aligned, IT projects can veer off course when stakeholders expect sunny beaches and end up in a rainy layover.
I’m writing this in May, holiday season is incoming so …
Here’s how to keep everyone informed, excited—and realistic—about the journey.
- MAP THE ROUTE BEFORE PICKING AN ARRIVAL TIME
The first question from stakeholders is often: “When will it be delivered?” That’s like announcing an arrival time before you’ve even booked flights or checked the train schedule.
Imagine you’re heading from London to Barbados. Would you just throw out an ETA? Or would you check flights, layovers, transfers? Too many projects lock in deadlines without understanding the route.
Take the time to plan the journey together, mapping each leg of the trip: major milestones, dependencies, risks. Not only does this give you a credible timeline, but it helps avoid that moment halfway there when you realise someone booked Wroxham instead of Wrexham!
So, funny story, back in the day some friends of the family who are Arsenal football fans set off for an FA Cup tie in Wrexham. It was the days before SatNavs and the task of planning the route was left to an uncle. It was a good hour and a half into the journey before they realised that the route he had planned was taking them to Wroxham in Norfolk rather than Wrexham in North Wales – literally the other side of Britain. The moral is that proper journey planning may take a little time up front but it will pay back later with accurate timescales and clearly defined and agreed expectations.
- DON’T PACK MORE THAN YOU NEED: KEEP IT SIMPLE
Ever been that person who packs 15 outfits for a 4-day break “just in case”? Project documentation can be the same: overstuffed, overcomplicated, overwhelming.
Stakeholders don’t want to see every pair of socks you packed—they just want to know where you’re going and when you’ll get there.
Keep your plans light, clear, and relevant. Focus on the essentials: what’s being delivered, when, and what success looks like. Overloading them with technical jargon risks miscommunication and frustration—especially when their expectations don’t match the reality inside your suitcase.
- START WITH THE DESTINATION IN MIND
Before booking flights or hotels, you pick where you’re going, right? The same applies to IT projects. Ensure everyone’s aligned on the end goal—whether it’s a new system, an upgraded process, or a total digital transformation.
When stakeholders each imagine different destinations (one thinking beach, another picturing a ski resort), your project will be pulled in conflicting directions. Clarify the “where” before the “how”—or risk arriving somewhere no one wanted to be.
- ALWAYS ALLOW FOR DELAYS: EXPECT THE UNEXPECTED
Flight cancellations. Lost luggage. Strikes. Anyone who’s travelled will know things rarely go 100% to plan—and IT projects are no different.
Build buffer time into your project schedule. If the journey should take five months, aim for six. This way, when a vendor delay or unexpected issue crops up, you’re not immediately off track.
And if you arrive ahead of schedule? Bonus! Stakeholders will see you as delivering early—while your team feels like heroes sipping piña coladas at the finish line.
- CONSTANT UPDATES PLEASE!!! POSTCARDS (OR INSTAGRAM POST UPDATES) FROM EVERY STOP!
Milestones aren’t just internal checkpoints; they’re like Instagram-worthy landmarks on your journey. And just like friends want updates from your holiday, stakeholders need to hear from you at each stop.
Share regular, visible progress updates—whether that’s reports, dashboards, demos, or even a quick call. Celebrate milestones publicly (yes, even on Teams or Slack), so everyone feels included.
And if a detour occurs? Be upfront. A missed connection is far easier to explain at the time than after everyone’s been waiting at the arrivals gate.
- CHOOSE YOUR TRAVEL COMPANIONS WISELY
You wouldn’t hike Kilimanjaro with flip-flop wearers. Likewise, pick your project team based on skills, strengths, and fit for the journey ahead.
A solid crew boosts stakeholder confidence and raises expectations for success. Spot a gap? Don’t be afraid to bring in specialists or external resources to plug it—think of it like hiring a guide for the tricky parts.
The better your travel companions, the smoother the adventure (and fewer awkward “we should’ve brought someone else” moments).
If you identify a capability gap, Stoneseed’s Project Management as a Service has an abundance of resources ready to plug straight in!!
- CUSTOMS & CULTURE MATTER: SPEAK THEIR LANGUAGE
Every destination has its own customs—and so do your stakeholders. Some love detailed plans, others want bottom-line results.
Tailor your communication to their style. Trying to explain agile sprints to someone expecting waterfall milestones is like ordering a cheeseburger in a vegan café. Speak their language to avoid culture clash—and ensure they feel respected and heard.
- DON’T LET A MISSED CONNECTION RUIN THE WHOLE TRIP
Even the best-laid plans can hit snags. The key? Contingency planning.
If one leg of the journey falls through—a supplier delays, a requirement shifts—don’t panic or scrap the whole itinerary. Be ready with plan B (or C) and reassure stakeholders that the destination is still in sight.
Remember: it’s the journey and the destination. How you handle hiccups says as much as what you ultimately deliver.
- KNOW WHAT’S IN YOUR SUITCASE: WATCH FOR SCOPE CREEP
Ever packed for a weekend break only to end up paying for extra baggage? Project scope creep works the same way.
Even worse, watch who has access to your bags, you don’t want to wind up in a Far East jail because of what someone slipped into your suitcase while you were distracted!!!
Protect your project suitcase: check what’s really essential, what’s “nice to have,” and what snuck in last minute. Every extra pair of shoes (feature request) adds weight, cost, and time.
Regularly review your packing list (aka scope statement) with stakeholders to avoid surprises at check-in—and ensure you’re still headed to the same destination; with baggage you can carry.
CONCLUSION: KEEP EVERYONE ON THE SAME JOURNEY
Managing stakeholder expectations is like planning a group holiday: it takes alignment, patience, transparency—and a healthy sense of humour when things go off track.
By mapping the route together, keeping plans simple, allowing for delays, and sending regular updates (whether postcards or Instagram Stories), you’re far more likely to arrive at your destination with smiles all round.
Let’s face it: nobody likes arriving at the airport, realising their friends are waiting in a different country – unless it’s the one in the flip flops!
More about Project Management as a Service from Stoneseed