6 practical steps to deal with challenges on projects

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Strive for progress, not perfection along the way

As a Strategy Lead, and like other colleagues at dxw, I often support clients to identify problems and solutions – whether it’s resetting a project to get it back on track, or helping to design, build, and operate digital public services that meet user needs.

I’m going to share some practical tips about how to address challenges in projects, based on my experience. 

Where to begin when facing challenges?  

Tackling challenges on projects can feel daunting. Throughout my career, I’ve worked with many clients to define and solve problems, and I’ve outlined 6 steps that I usually take. This isn’t a rigid process. It can be applied in many different forms – a day-long team workshop, 1-2 week long sprint, or a longer project, depending on what best suits the context.

6 steps to address challenges 

The 6 steps I tend to follow guide me through:

  • gaining enough context
  • identifying challenges and solutions
  • planning and implementing practical ways to tackle them, while continuously learning and iterating 

Let’s take a look at each step in more detail.  

1. Understanding the context 

I tend to start by gathering as much project context and background as possible. This can be by talking to stakeholders in group or 1-2-1 sessions, and catching up with team members individually (depending on the size of the team, time available and sensitivity of the issues). Where feasible, I’d also suggest running a team retrospective for an existing team/project or a brainstorming session for a new team to jointly discover challenges. The appropriate format, scope and focus of activities during the session should be based on the particular context. This helps reveal what has and hasn’t been working to enable the next step – framing the challenges.  

2. Framing the challenges

When there’s enough background to get started, the next step is to collate the insights, to analyse, and consolidate them around the main emerging themes into a digestible format. A good way to do this is by using an online visual tool such as miro. This helps to play the identified challenges back to the team and stakeholders and check if we’ve captured facts accurately. It’s also crucial to get aligned on the scope of issues that will be addressed, as some might not be a priority or have little impact. A team session can be useful to briefly present the findings and discuss the challenges, as well as to agree what will and won’t be within the scope. Be realistic with timelines and what is feasible. Less is definitely more here. 

3. Collaboratively exploring solutions

Now that the scope is clearly defined with clarity on the challenges, it’s time to collaborate on agreeing what to tackle and how. As it’s likely there are multiple challenges to address, the team should focus on agreeing the priority order for dealing with them based on their importance and impact on end users, and not just stakeholders’ frustrations. There are lots of different activities that a team could undertake to creatively brainstorm possible solutions, such as crazy 8s. Involving the team in finding solutions that affect them can help increase their buy-in and empower them to effectively implement the next steps.  

4. Agreeing a plan

The previous steps enabled the main challenges to be collaboratively framed and potential ways of addressing them to be identified. Now it’s time to focus on getting from knowing what to do, to actually doing it. A useful starting point is agreeing how the team will work together. This can be done during a reset/ways of working together session for an existing team or project inception/kick off meeting for a new team. I’d recommend the main points to cover as a team include at minimum:

  • project plan/roadmap (reflecting the scoped out issues and solutions)
  • workflow and acceptance criteria
  • roles and responsibilities
  • project ceremonies/meetings 
  • working together principles (like working transparently, regular communication and feedback, and continuous learning)
  • tools and anything else that the team needs to successfully deliver the solutions. 

5. Implementing the solutions 

By this point, there is more clarity about what needs to be done and how the team can work together on achieving the goals to overcome the challenges. It’s now time to translate the higher level solutions into actionable next steps. This work can be led and facilitated by the Delivery or Project Lead/Product Owner or, yes you got that right … collaboratively as a team! If there is no permanent lead, the team might consider having a rotating lead role that team members swap in and out of. This is also a good capability building exercise. 

Using a virtual Kanban board, like Trello, enables you to break the high level goals down into smaller tasks and populate the project backlog. This can be organised to reflect priorities, with the highest one at the top of the column. From here, it’s all about the team taking on the tasks, regularly checking in on progress during daily stand-ups and planning sessions (or other regular team meetings), and continuously monitoring progress and assessing the feasibility of the plan. 

6. Continuously learning and iterating

The last step is more of an ongoing and active reminder to regularly learn and iterate plans based on the new things that come up along the way. For me, this starts with embracing that ‘failures’ are actually opportunities to learn, and trying new approaches if something isn’t going well. Frequent team retrospectives allow the team to identify what is and isn’t working early on. And let’s not forget to share appreciation for each other and celebrate successes, no matter how big or small they are! 

Let’s sum this up 

I’ve shared 6 steps to guide teams through dealing with challenges:

  1. Understanding the context
  2. Framing the challenges
  3. Collaboratively exploring solutions
  4. Agreeing a plan
  5. Implementing the solutions  
  6. Continuously learning and iterating

To wrap up, I’d like to acknowledge that tackling challenges is, as the name implies, challenging. It requires a lot of individual and team time, effort and energy. This makes it easy to avoid or postpone, but issues are unlikely to go away without being addressed. So it’s usually better to deal with them promptly and remember to strive for progress, not perfection along the way. 

I’d also encourage those looking to address challenges to reach out and ask for help if needed. There are many people and organisations, like dxw, that can help save a lot of time, resources and frustration by using their experience and offering guidance on framing challenges, identifying solutions and implementing them in effective and agile ways. I hope my experience and the tips I’ve shared are helpful – please get in touch with us if you’re interested in finding out more.