This article is the first in a series that discusses the key attributes to successfully navigating change and transformation from practical experience. The aim of the articles is to discuss my five pillars to successful change and/or transformation initiatives, which are not concerned with the different methodologies available within the market sector. Instead they talk through the common pitfalls of change and transformation that can, if used correctly, become key components to its success.

The pain of challenging

We’ve all sat in a meeting listening to someone present and felt their pain when being challenged by other attendees. Maybe it’s human nature to want people to succeed, and being mindful that the path of least resistance is the best one to take, so why challenge someone who’s already under pressure to deliver?

Why it’s good to challenge

If approached in the right manner, i.e. one that comes from a place of wanting to do the best by people and what they’re trying to deliver, challenge is a powerful tool. It provides the opportunity to determine if what we’re doing is the right thing, done in the right way and at the right time.

If someone didn’t challenge us, and we’re either unaware of the issue, or too stubborn to pay attention to it, then there’s a decent chance that we’re going to carrying on doing what we’re doing even though it’s not set up for success.


“Challenge can be stepping-stones or stumbling blocks. It’s just a matter of how you view them”.

How we receive and deliver challenge is equally important to what’s being challenged. If I’m aggressive in delivering a challenge, regardless of its accuracy, it can be received badly and instead of focusing on the message within the challenge, it’s seen as an attack. On the flip side of the coin, you need to be willing to accept challenge, regardless of how it’s delivered and actively not respond in a defensive manner (easier said than done).

The final part of the mindset, and probably the most important, is to start challenging yourself and the work you’re doing. Think on “why are we delivering this” and “how can we improve what we’re doing”? Don’t get so caught up in what you’re doing that you can’t see the cracks in the woodwork.

I once took on a transformation programme and was so excited for the opportunity that I didn’t ask the fundamental question, “why are we doing this”, “are we doing this at the right time” and “is this the best use of the organisations time, resources and funds”? 

Throughout the work I faced multiple challenges concerning the fundamental reason why we were trying to transform the business and was it the best thing to do. I was so caught up in the mindset of “I know what I’m doing and I know what’s best for the organisation, they just don’t know what good looks like” that I didn’t take the time to consider the challenge. I didn’t want to listen to what wasn’t going to work, instead I spent more time trying to win people over and get them to see what I truly believed. 

A better approach would have been to understand their concerns and take an honest look at what I was doing to see what needed to be resolved before pushing ahead. The work didn’t turn out to be a disaster, but there could have been benefits in taking a step back, listening to the naysayers and changing direction. 

What, when and how to challenge

What (who) to Challenge:

  • Challenge yourself
  • Challenge your team
  • Challenge the work
  • Challenge your sponsor
  • Challenge the business

When to Challenge:

To ensure you start on the right path and that the end of the path delivers the desired outcome, challenge from the outset through to the end. This doesn’t mean you need to challenge every day for the sake of it, instead you can use critical stages throughout the change as opportunities for constructive challenge.

How to Challenge:

To receive and present challenge, the right environment is needed. An environment where people won’t feel threatened by challenge nor afraid of challenging. I’ve found that discussing with my team and stakeholders how challenge is best delivered helps everyone establish some basic guardrails to keep discussions productive.

Once this is in place, the next step is to consider what scenarios are best to hold the discussion.  A good starting point to consider is the project steering group, so long as you have a balance of individuals that are willing to do this. If the steering group is predominately made up of stakeholders that are pro your work and less likely to challenge, then an alternative will be more beneficial.

If this is the case, it’s worth considering establishing a separate group of people that you know will challenge you and the work. I’ve heard of this referred to as the “Red Team” in some organisations, where a group of people are brought together from the duration of the work, to challenge what’s being done and discuss solutions. This group of people can turn into your most useful forum as you can be confident that they will make sure you’re doing the right thing and stop you if you’re not.

This forum is useful to discuss the key topics of the project. But the premise of this forum shouldn’t be limited to the key topics, instead it can become part of the meetings at lower levels within the change teams. So long as there’s a good balance of challenge and wins.

Final Thoughts

Sometimes working in complex change can be challenging enough, but without challenge who will be consistently ensuring what we’re doing is the right thing, for the right reasons and at the right time?

If we can remove our defensive response to challenge and encourage it, then it can become a fundamental tool to ensure change is successful. And remember, you can’t spell challenge without change!

    1 Response to "Why for Success – Pillar 1"

    • Gillian Beadle-Phelps

      Really useful advice and relevant to several projects I’m involved in in the public sector. Challenge is often the thing I dread in a meeting but this is a reminder that it should be the most exciting element of a project because it helps to iron out the issues and increase the likelihood of success!

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