James Sayer Fri, Sep 3, '21 7 min read

Pragmatic mindsets required for digital transformations.

So, you’ve aligned the goals of your business and IT team around a common vision, engaged all levels of the organisation, and have the data in place to monitor the impacts of change. What are the key mindsets for making this happen?

Successful transformation projects start simple

Most teams will start their journey with what is often referred to as mechanical agile. They adopt some new roles and ways of working such as timeboxing, iterations and task boards. Whilst this helps to open people up to new ways of working, the change in individual mindsets and organisational culture comes over time as teams hone their new skills and start to experience the benefits of these new practices.

The approach that Vanessa Towers and Cecil Dearborne from Thoughtworks promotes very much aligns with our thinking on this matter, where successful transformations begin with targeted change – which are essentially summed up by enabling experimentation, proving the value of modernisation, and delivering value quickly.

Embrace transparency and embed it throughout

Most agile transformations identify improved transparency as an early goal. Whether it’s better visibility of the work through a well-structured backlog, visibility of progress through regular reviews, or visibility of impediments and opportunities through retrospectives. Leadership teams will soon gain a much better grasp on what is happening and benefit from being able to steer the direction.

However, leaders should also remember that transparency is a two-way street. Trust with teams is established through ensuring that decision-making processes, the rationale and outcomes are visible. Leaders also need to be personally visible and engaged, attending sprint reviews, providing direct feedback to teams and helping to remove the impediments that hold them back. This is no longer done at arm’s length, by passing feedback though the hierarchy.

Be flexible from the beginning

Just as agile development practices aim to incorporate the frequent inspection and adaptation of our software solutions and the working practices that create them transformation initiatives need to adopt the same mindset.

Whilst it’s important to remain focused on why the organisation is transforming and the long-term outcomes that you’re driving towards, be prepared to adapt your approach by incorporating real-world learning to fit your organisational context.

Transformations can quickly suffer from a loss of buy-in when teams are asked to continue doing things that they can see are not working. Our advice is to avoid planning too much detail up front, listen to the feedback from regular team retrospectives and look at what the data shows.

Leaders who successfully adapt their transformation plans in this way also have the benefit that they can be seen as leading by example. It also has another benefit of increasing employee morale, as they feel respected because their feedback is incorporated.

Resilience when it counts

Whilst it may seem to contradict the previous point about adaptability, it is also important to acknowledge that transformation takes time. Achieving lasting change requires teams to adopt not only new practices, but a new mindset and culture. Transforming these will normally be measured in months or even years, rather than days or weeks.

Inevitably, teams will experience failures along the way, but leaders should help them to resist the temptation to abandon new ways of working and revert to the old ways. It’s better to try another new approach.

Embrace mistakes as an essential part of the learning process and avoid the fear of failure that will stop people from trying new ways of working.

Morale matters so celebrate your wins (even small ones)

As the first small achievements of a transformation project can be seen, it is important to promote the success both within the immediate team and broader organisation. This sets the tone for the type of project you want deliver. And it also helps give confidence to those who actively and passively resist the changes being undertaken. 

Whilst having the data to validate your success is obviously important, storytelling from leaders helps to provide examples of the behaviors and outcomes you’re working towards that can be far more tangible to people than your initial plans and presentations. Stories often feature narratives where brave protagonists (your people) overcome adversity and can act to inspire others.

We’ve seen many times that promoting even modest achievements in this way can start to build momentum quickly.

Hopefully this provides some useful insights into approaches that can be applied in your own transformation. Good luck and be sure to get in touch if you would like to find out more about what Jade can do to help.

James Sayer is the Delivery Transformation Lead at Jade. James has spent the last eight years designing and implementing operating models of scale, as well as helping optimise agile operating models. He has also worked with leadership teams through to the development teams to make the implementation programmes successful – in both the short and long term.

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