In a recent Client Story, I wrote about how we helped a major retailer spot a gap in its Cash Management processes. It led me to thinking more broadly about the importance of asking questions and how people don’t always speak up.

In this article I reflect on the importance of asking the straightforward questions and how that can make a difference when it comes to project delivery. 

The Sprint Scenario

I’d like you to imagine you're sitting in a sprint review meeting. The development team supported by the QA team are presenting their latest work, and the discussion is quickly becoming complex. People around the virtual table are either nodding along like they understand it or are not paying attention and quietly working on something else. The teams have been working hard against tight deadlines juggling competing priorities. Yet your instinct is telling you something doesn’t feel right. There’s a disconnect somewhere, a gap in understanding nobody is addressing. 

The development team continue confidently presenting their work. They have a great deal of technical skills and knowledge, but they are talking in jargon showing some very complex looking code and outputs. It seems on the surface that this is the solution to the problem that you brought them, but following along is becoming more difficult as the meeting progresses. You want to speak up and ask for clarifications, but everyone else seems to understand it, so what are you missing? 

Misunderstandings or Misconceptions 

The answer to that final question is almost certainly you aren’t missing anything. In complex projects involving many moving parts it can be easy for misunderstandings or misconceptions to creep in. It’s also often the case that technical people will steam roller meetings as they are sure they have met the brief and are eager to move onto the next sprint with its waiting list of demands. So, while people are nodding along and trying to keep up, or worse, not paying attention, the chance that someone intervenes keeps reducing as people don’t want to be seen to not know what is going on. 

Now you may be an experienced leader or battle-hardened Delivery Manager who wouldn’t be afraid to jump and start asking questions, but are you always there to do that? Or can you say for sure that other people on your team will be prepared to always do the same as you when faced with this situation. Many leaders will delegate such meetings and decisions to less experienced members of their team, after all you can’t be everywhere at once to attend all the sessions that are happening on large scale programmes. And that is where problems can start, an overlooked requirement or unintended consequence of a code change leads to a major issue down the line. 

Asking The Questions 

I've been there and seen this scenario play out during my career. Early on, I was someone who stayed silent, reluctant to ask questions for fear of appearing uninformed. It’s easier and safer to sit back and stay silent, hoping someone else will speak up. But for me everything changed thanks to an inspirational mentor and leader.  

He showed me the immense value of asking straightforward, sometimes uncomfortable questions. Challenging team-mates, vendors and even the client, his willingness to speak up kept major transformation projects on track and significantly improved outcomes. He was able to do this in a genuine and non-confrontational way that really delivered results. 

Inspired by his example, I learned to ask those simple, yet powerful questions myself. It wasn’t always easy or comfortable, but when you have seen the difference it can make, it gives you the confidence to speak up. It doesn’t mean that everyone you work with will always appreciate it, but when you show you are doing it for the right reasons it can make it easier for them to see your point of view. 

Real Life Impact 

This was a key aspect of the Client Story about Cash Management that I referred to at the beginning of this article. In that example asking the straightforward question "Can someone explain, in simple terms, exactly what the stores need to do with cash on the system at the end of each day?" made all the difference.  

This gentle prompt encouraged the team to step back and reconsider their assumptions. As we began exploring that, the fundamental misunderstanding became evident. The proposed solution didn't align with the actual requirements and could have caused serious problems in the long run. 

This underscores for me how essential clarity truly is. Simple questions can uncover hidden gaps before they escalate into costly problems. I've seen how today's unaddressed confusion turns into tomorrow’s technical debt. Minor misunderstandings snowball into major delays, increasing costs and damaging reputations both internally and externally. 

The Lean Tree Way 

Our team at Lean Tree brings deep experience in digital transformations across industries. We understand first-hand the pressures teams face and the reluctance many feel about voicing basic yet essential queries. We're seasoned professionals comfortable asking the awkward questions others shy away from. 

Does this scenario feel familiar? Have you or your team hesitated to speak up in critical moments? Reflect on this: Are you and your team always confident enough to question the obvious, or would having someone alongside who can confidently ask these questions make all the difference? 

We're here to provide that confidence. Get in touch, and let’s discuss how our experience can help your next project succeed.