Straight Talk on Project Management

Planning for your vacation

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Planning for your vacation or your IT project. Pack the right essentials

As I write this the school holidays are looming, and the year is zooming by. I don’t know about you, but my thoughts have already started to turn to the holidays, and specifically the annual family holiday – our chance to relax, unwind and create some fabulous memories together.

As I’m planning the “Cotgreaves On Tour 2022” itinerary it strikes me how similar to Project Management this endeavour is. From managing different stakeholder expectations (the must have elements of my teenage children’s vacation being very different to those of my wife and I) to the simple but crucial need for a realistic budget. Every Project Management muscle I have will get a final flex on this job before I can relax and enjoy a cocktail watching the sunset.

Like all projects, ultimately, it’s about outcomes and as usual, each stakeholder has a different view on what they should be. In the same way that the Financial Director and the Transport Manager may want different things from a software roll-out that links both their functions, my wife, my son, my daughter and I have recently had conversations about our expectations of our upcoming holiday.

They are as eclectic as any IT Project stakeholder wish list; Water and land sports, relaxing sun soaked beaches, fun in the pool, drinks by the pool, discos, peace and quiet, vibrant family activities, an oasis of calm from our busy working lives, all you can eat buffets, romantic candlelit dinners for two. As always it is down to me to deliver what is possible and manage expectations around what isn’t.


Surely, if you have set a clear scope from the very beginning and the measures of success are clearly defined, achieving those measures will mean you have a satisfactory outcome, won’t it?

Well … no actually.

Despite knowing in advance that the pool isn’t heated, that the hotel reviews say the rooms get cleaned just once a week or that you’ll be visiting during hurricane season – somehow it still comes as a surprise when you land and a storm with a name whips off your sombrero.

In IT Projects, it can be equally as frustrating to spell out clearly what the post project world will look like, only to have a key end user contingent say they were expecting something different entirely.

The thing is about measures, governance, scope … these are all tools of the head. They’re all vital for success but for real stakeholder buy in you have to tap into the heart. For stakeholders to really ‘get it’ you have to paint a picture and you have to put them in that picture.

The unheated pool is a blessing if it’s a place to escape the blistering heat, the weekly cleaning of the room means that a stranger won’t be coming into ‘our space’ each day and we’ll also be doing our bit for the environment.

In IT Project management the same applies.

Sure, the new software rollout might mean getting used to working differently but it will also mean that you won’t have to duplicate work. If your thinned out workload means that you’ll have more space to breathe during and between tasks or that you might even get the occasional early finish on a Friday … well, who wouldn’t buy into that? At least everyone will know what to expect, how it will ‘feel’, at the end of the journey.

With this in mind let’s list a suitcase of other essentials that will improve the outcomes of both IT Project journeys and, much more importantly, your summer holiday.


I guess in the introduction we touched on engagement. Compromise is also a powerful tool with this.

My friend and his family holiday in Ibiza each year. The first week in a villa just outside of San Antonio. His teenagers get to experience the youth culture and excitement of the party side of the island for a week and then the family heads to the quieter Santa Eulalia for a week of rest, relaxation and retail therapy. It’s a compromise that works, the kids love the atmosphere, bright lights and loud music and their parents know that they’re safe from the more hedonistic goings on in that first week and the second week everyone is ready to chill out.

The result is that everyone comes home happy.

Compromise is often the most useful thing to pack for your IT Project delivery journey so (to stretch the holiday metaphor a little further) you want it in your ‘carry on’ luggage and not stored in the hold. Keep the power of compromise readily available whenever you need it, make sure it’s in your overhead locker!


So IT Projects and family holidays can benefit from a generous dose of compromise and to help with that … pack your prioritisation skills too. My friend’s teenagers need to feel that they’ve let their hair down in Ibiza and they need to return to school and college with some ‘cool’ stories but relaxation is the main priority for my friend and his wife. That’s why the headline act of the holiday is the restful part – they need to come home with batteries that have been fully recharged.

When you find the best solution that suits a range of stakeholders’ priorities, you score the greatest project wins. To achieve this you need to identify a hierarchy of needs based on things like the importance of the stakeholder, how aligned stakeholder needs are with the strategic objective of the project and how important each ‘must have’ actually is to the individual stakeholder (it’s amazing how many IT Projects miss critical deliverables for the sake of a folly or vanity ‘must have’).


I mentioned holidaying in the hurricane season earlier. There was a chap on the television last week who actually schedules his holidays around severe weather. He is an amateur meteorologist with a particular interest in hurricanes, tornados, that kind of thing. He has a family but holidays alone for this, I can’t begin to imagine why his wife and kids don’t join him!

Point is timescales matter.

For us, we want almost guaranteed sunshine and to come home with a suntan. A neighbour visits the same place we are considering but, finding it too hot when we are there, she goes later in the year. Either that, or she’s trying to avoid us. Either way – the timescale is key to a satisfying outcome!

It’s not just ‘when’ either – it’s ‘how long’ that matters. I know people who don’t properly unwind until they have already been away for a fortnight. What good is a 14 night holiday to them? To achieve the intended outcome they have to book at least three weeks away.

It’s the same with IT Projects where accurate time estimation is a vital skill. When you understand the project outcome and have broken down the necessary tasks into chunks, you can begin to estimate how long each will take. Make sure you factor in potential risks like higher priority projects taking resources away, staff falling ill, suppliers letting you down, etc, etc.

You can lose both credibility and money when you get Project timescales wrong, heaven forbid, you could even find yourself sharing a breakfast table with a neighbour you’re trying to avoid.


Budgets are boring, who gets excited by spreadsheets? But, where would we be without them?

You will have budgeted to pay for your holiday, perhaps eating out less at home so you can eat out more while away. It’s more than that, though.

Do you also take away a little contingency money? You know, just in case you see something at a market that would look great in your home or in a ladies fashion boutique that will make the suitcase even harder to zip up at the end of the holiday?

This is a key Project Management skill that really helps planning for our holiday – plan financially for the little surprises so they don’t suck budget from elsewhere! You don’t want to be eating beans on toast for the last three days of the holiday because you ate lobster the whole first week.

Budget for scope creep, budget for having to put in some overtime, budget for how deliciously moreish and addictive the lobster you tried on the first night was.

It’s always better to finish any journey with some currency left over.

Get A Good Tour Guide

If you’re planning on going somewhere new – how do you know it will be alright? You seek advice and assurances, you talk with friends and family, hit up Trip Advisor. For every excellent review, you will find a negative one, they can’t both be right, can they? Here we come full circle back to context … Which should you believe?

Of course, they can both be right. They are subjective, personal opinions, supported by tangible facts – how often did the sunshine, was the room clean, was the pool warm enough?

In IT Project delivery, success is also often down to personal opinion – did the IT Project meet my personal needs, did the IT Project cost more than I expected?

It can help to elevate the journey above the clouds of subjective perspectives and there are end-to-end Project Management services available that will allow your project to progress without the internal baggage that often causes delays.

Almost every IT Project is a journey to somewhere new, otherwise what’s the point? Therefore, an external, independent pair of eyes that’s already seen the route you’ll be travelling can keep you safe on your travels.

Don’t climb Everest without a Sherpa.

So, in conclusion, whether it’s an IT Project journey or a family holiday you’re planning – remembering to pack the essentials is the key to success. Scope, budget, prioritisation, all the things mentioned here (and others we could chat about over email or a coffee) are your passport to success.

Have a great time wherever YOU holiday this year and finally … don’t forget your toothbrush.

Safe travels.

If you fancy a good holiday read, why not download my latest ebook

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