The Power of Asking ‘Why’ - Project Kick Offs

One of the biggest mistakes teams make at the start of a project is taking the initial brief at face value - accepting the stated problem and jump straight into solutions. But without a deep understanding of why there is a problem, or why the project has been initiated in the first place, the risk of veering off in the wrong direction and missing your target is huge.

Why Asking ‘Why’ Matters

The real foundation of any successful project isn’t just a well-documented plan or a skilled team—it’s clarity of purpose. If you don’t get to the heart of why the project exists, you’re building on shaky foundations.

Take this example: "We're implementing a new CRM"

💬 “Why do you need a new CRM?” 👉 “Because the current one isn't fit for purpose.”

That sounds reasonable, but if we stop there, we’re missing the bigger picture. Let’s dig deeper:

💬 “Why isn't it fit for purpose?” 👉 “It’s clunky, and no one uses it.”

💬 “Why does that matter?” 👉 “Because we’re missing opportunities to engage better with our customers.”

💬 “Why do you want to engage with your customers better?” 👉 “Because we're losing customers and revenue.”

Now we’re getting somewhere. The real goal isn’t just a new CRM—it’s better customer engagement, increasing customer retention and revenue growth. That understanding will shape every decision, from system selection to implementation and user adoption strategies. 

Without digging deeper, the requirements for your CRM won't align to the benefits you need to achieve. 

It also helps to clarify the metrics. How you measure your project's success is vital and asking why ensures you measure the right thing. In the example above we may have picked 'CRM implementation status' as our metric which (whilst useful to track) is not the outcome we're looking for. By asking why we get better metrics, customer engagement from a CRM and ultimately revenue and customer retention. Much better indicators of success. 

The ‘Why’ Isn’t Set in Stone

One of the biggest mistakes teams make is not revisiting their ‘why’ as the project moves forward. External factors can shift priorities, and when that happens, the project direction should adapt too.

Let’s say a company starts a project to implement an enterprise collaboration platform to improve in-office communication. The goal is to consolidate tools, reduce email reliance, and create a more connected office culture.

💬 Why do we need a new collaboration platform? 👉 “Because teams struggle with communication across departments, and we want to improve knowledge sharing.”

💬 Why does that matter? 👉 “Because better collaboration will speed up project delivery and decision-making.”

Everything seems on track—until COVID-19 hits, and the entire workforce suddenly shifts to remote work.

💡 Suddenly, the original ‘why’—improving in-office communication—doesn’t fit the new reality. The team realise they need to pivot: instead of focusing on a platform optimised for office-based work, they now need to prioritise remote-friendly features like virtual whiteboards, asynchronous collaboration tools, and better integrations with video conferencing.

This shift ensures the project stays relevant to the company's new way of working, rather than delivering a solution built for an office environment that no longer exists.

External changes - like COVID-19, market shifts, or new regulations - can change everything, and internal shifts like a company’s strategic pivot can also redefine priorities; if the ‘why’ evolves, the project should evolve too."

Building Trust to Get Honest Answers

The challenge? Not every stakeholder will feel comfortable revealing the deeper motivations behind a project. That’s why trust is essential. When clients or teams feel safe being honest, you uncover the real drivers behind their decisions.

This is where skilled consultants, leaders and project managers make all the difference. They don’t just take answers at face value. They build relationships where asking ‘why’ isn’t intrusive—it’s expected.

What Do You Think?

Do you make a habit of asking ‘why’ in your projects? Have you ever seen a project go off track because the initial ‘why’ wasn’t fully understood?

Let’s discuss in the comments. What are the pros and cons of going deep with ‘why’?