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IT Project decision making: How the best choice between two options can often be the third!

“May your choices reflect your hopes, not your fears.”– Nelson Mandela

I heard something on a podcast this week that was both an epiphany and blindingly obvious in equal measure, in fact, its genius was its simplicity.

“If you find yourself deciding between only two choices, maybe you need to widen the aperture,” Roelof Botha, managing partner of Sequoia Capital, said on their “Crucible Moments” podcast.

The words leapt out of the speakers and grabbed my attention.

This is the man who helped tech companies like Instagram and YouTube make decisions that would facilitate their growth from early-stage start-ups into industry giants. When someone like Roelof Botha talks about strategic decision making – I crank the volume to 11!!!

The “Crucible Moments” podcast is a fascinating listen, especially as Roelof Botha (whose thoughts are the inspiration for this blog) isn’t the main subject. He plays the role of presenter; the main guest is Jack Dorsey (former Twitter CEO who now runs the financial services company Block). The central narrative of the podcast is the evolution of Block from its origins as Square, and how they created Cash App, a ‘third’ option, which is now responsible for half of Block’s revenue. The strategy of expanding the number of options for consideration was instrumental in helping Block identify and eliminate what wasn’t working and focus on more profitable projects.

“Is there a third or fourth option that you haven’t even considered that you need to throw into the mix to really test whether that is the right path?” Roelof Botha added.

Simple, right?

Botha’s wisdom was earned observing CEO’s struggle choosing between two options.

How often do you find yourself, as a CIO or IT project leader, in a similar mental wrestling match?

How often have you had two alternatives to choose from, come to a decision that you and your team followed with all your heart, only to be disappointed by the outcome? How many times, in post project reflection is the option you chose still, on paper, the best – even with the benefit of hindsight?

Maybe there was a third, fourth or fifth option that you overlooked.


Stoneseed’s Project Management as a Service was a response to a two-horse race where, often, there wasn’t a winner.

In many of the early project teams I worked in, when it came to talent resourcing options, it was either permanent staff or contractors. You either added to your headcount or you risked adding to your budget with contractors (when a six-month project overruns, those pesky contractors still expect their daily rate!!!!) One friend tells the story of the time he was a contractor on a public service IT project that was cancelled midway, but he was paid to the end of the contract, meaning for three months – his job was to top up his tan!

An innovative resourcing solution, like Stoneseed’s Project Management as a Service (PMaaS) was a third option that many had not considered. To be fair, it didn’t exist until we had our epiphany moment and created it but, even today, many IT project resourcing conversations boil down, effectively, to a debate about perms vs contractors!

PMaaS may be the third option you haven’t considered!


Botha’s advice about widening the aperture is sound and, at Stoneseed, we practice what I’m preaching here. We’re not an off-the-shelf-project-management-solution-warehouse, if I’m suggesting that you think beyond a limited set of possible solutions, it would be hypocritical to take a ‘this worked for another client, we’ll sell you this too’ approach. We never do. We’ll tailor our recommendations to match your exact needs, observing, learning, and evolving our project management resource universe along the way.

As Botha said, “… as you evaluate your own decisions, key crucible decisions, strategic options you’re weighing … have as wide a set of choices as possible that you’re evaluating.”

Even if you’re not already applying this to strategic decision making in your IT Projects, the chances are you’re subconsciously doing it elsewhere in your life. Have you ever been looking at a product on Amazon or eBay, scrolled down to notice the app had laid out similar products for you to compare, and ended up buying something that wasn’t on your original radar. You widened your aperture!

Or have you ever ordered takeaway pizza? Have you opened the Domino’s app, your taste buds tingling for their Mighty Meaty®, only to be tempted by the Vegi Supreme and a Vegi Volcano (with sides of garlic bread, wedges, and cookies for pudding)? The way the pizza menu is laid out by Domino’s is textbook aperture widening, designed to help you choose by laying all the options out, even the ones you hadn’t considered.

Inadvertently, the Stoneseed website is similarly laid out and effective. Clients often come to us looking for a Project Manager and also hire in wider Project Management Office functions or hit up the website to check out our advisory services and add Business Analysis as a Service (BAaaS) to their basket!


Of course, we don’t need to order in pizza (but let’s, eh? –  Editor) or fire up an online shopping app to find an area where widening the aperture pays dividends.

Project management methodologies evolved from the rigid, reliable, linear Waterfall to the nimble and adaptive Agile approach and, eventually, the emergence of Hybrid methodologies – the “best of both worlds” third horse in the race.

Those words from Botha echo through this evolution. The Waterfall methodology was dominant in project management for decades, with its sequential approach, projects divided into distinct phases, each phase dependent on the completion of the previous one. If you’re old enough to remember or imaginative to envisage, there was a time when no-one imagined anything other than the structured framework of Waterfall, despite struggles to adapting to changing needs, and often delayed deliveries and costly revisions. It was just the way.

Shortly after the turn of the century, Agile emerged as a response to the limitations of Waterfall, prioritising collaboration, flexibility, and continuous customer feedback and involvement. Agile projects, divided into smaller, more manageable sprints, allowed for frequent adjustments and faster value delivery.

Two perfectly successful and different approaches, a methodology for every need! Who could ever need a third option? Right?

The visionaries weren’t done though, those who recognised the strengths of both Waterfall and Agile pioneered and adopted Hybrid methodologies. Blending elements of both methodologies, allowing for structured planning and adaptable execution, projects could benefit from a clear, well-defined plan, and have the flexibility to pivot as circumstances changed.

In this area of our profession, the aperture keeps widening, the evolution of project management methodologies continues, striking the right balance between structure and adaptability. Successful project outcomes in an ever-changing landscape depends upon evolution in thought just like this.


It’s not just that a third or fourth option can be better than the two you have on the table, sometimes they’re immensely better!! Often, we can create the illusion that we are choosing the best for our project when, actually, what we’re weighing up is two safe options, at the expense of more ambitious considerations.

I was having one of those conversations about work with a friend, you know the type, when you agree not to “talk shop” but inevitably gravitate towards it! He is grappling with some IT Project challenges and decisions right now. It occurred to me that all his perceived choices were defensive, unambitious, “prevent the project from failing” choices. None of the options considered were about to set passions alight, disrupt the market, or make his project team leap excitedly out of bed every workday morning. If you’re familiar with the football term – they were “parking the bus”.

This reluctance to innovate seemed cultural, even down to choosing talent.

“Who would you give this project to?” he asked me after describing two very adept sounding PMs.

They were both a very safe pair of hands, but this project needed a bit more oomph and gusto to deliver a real return on his organisation’s investment. They were asking ‘which of these waterfall masters will best deliver this project that is screaming out for an Agile approach?’

“Neither!” I said, and I reminded him about Project Management as a Service!

As Nelson Mandela reminds us “May your choices reflect your hopes, not your fears.”


Listening to Roelof Botha and Jack Dorsey, I scribbled down “observe, learn, improve”. I can’t remember which of them said it, but these three words serve as a powerful reminder.

It’s not enough to just observe and learn, if you don’t make the adjustments that make you the best of the best. Many Stoneseed clients contact us after observing that what used to work was no longer effective. They needed greater flexibility and control of resourcing costs, or better Project Management Office disciplines, or the value of Business Analysis without adding a BA to the payroll, or the fresh pair of eyes of independent advisory, or … that thing that you are grappling with right now.

That thing that you’ve narrowed down to two options… two perfectly good, sane, reasonable options … Perhaps its aperture widening time for you too. We’d love to help!

Check Stoneseed’s third, fourth, fifth (actually ever-evolving) solutions and options (like PMaaS and BAaaS), call 01623 723910 or email

 Find out more about Project Management as a Service from Stoneseed


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