Project Workflows should just…flow, right? Even Google Images represents ‘workflow’ as a series of harmonious shapes neatly connected with arrows… But in the real world things RARELY go according to plan. Remember that client who defaulted on payment, the tensions that arose within project teams and of course that one time the budget got blown out…?


Roadblocks come in many shapes and sizes and part of smooth project management entails anticipating disasters and doing your best to navigate or eliminate them. But don’t panic – we can help! Start by asking yourself these eight critical questions and learn how to overcome roadblocks in your project workflow:

1 – ‘Are there any roadblocks that you’re facing or that you’re worried about?’

I’d run out of fingers if I tried to count how many times this question was directed at me since I’ve joined Xero. I mean, were the managers expectingthere to be roadblocks?

Well… actually they were.

The sooner we accept that roadblocks are not a sign of mis-step or failure, but are actually a natural part of any process, the sooner we can move into managing them effectively. Fast Company even suggests “building them into your schedule” to avoid charting off-course. So ask yourself the same question and see if there are any roadblocks you can reasonably anticipate in the near future. We’re not asking you to be omnipotent…but a degree of foresight can be helpful.

For example, are you working with a particularly difficult client who you have to keep chasing for payment? Or is your team dispersed around the world? Recognising either of the two as a potential problem area, quickly jot down some potential ideas to avoid them escalating.

  • Anticipated Roadblock 1: Client always pays late.
    Potential Solution: Offer incentives or rewards for early payment
  • Anticipated Roadblock 2: Miscommunication due to physical distance
    Potential Solution: Implement tools for communication

At this stage you don’t need to have all the answers, but having an awareness of potential problems that might crop up will hugely benefit your management process down the line.

2 – Are you imagining obstacles that aren’t really there?

While caution is good, Melissa Jun Rowley, creator of docu-series Magic Makers makes an interesting point when she states “most obstacles aren’t real.”

Sounds wise, but what does that even mean?

Well, as it turns out, a lot of the roadblocks we face are self-inflicted, stemming from self-doubt and fear. I mean ‘roadblock’ is a big scary word. Let’s not blow an issue or delay out of proportion and term it a ‘roadblock’ too quickly!

3 – Are you starting every project the best possible way?

One of the easiest ways to mitigate potential roadblocks is to ensure you set yourself up for success. And while “a bad beginning does not (necessarily) keep you from a good ending” (Matshona Dhliwayo), why not commence the project with the best foot forward?

  • Design a great brief. Never underestimate the power of an awesome brief! There’s nothing worse than starting a project with less than zero direction, vague objectives and unspecific goals! Read on for more advice on creating an effective brief.
  • Conduct a rigorous onboarding process. This as important for your team as for the client and will help everyone get on the same page. A good onboarding process will typically cover ways of working, protocols, feedback procedures and methods of communication. Get more great tips on onboarding here!
  • Assign responsibility and leadership. Having a sense of ownership over aspects of the project, and assigning certain roles to staff, will ensure they’re much more invested in the project’s outcome and are more likely to speak up when they notice a potential roadblock. Also, if an effective and obvious “chain of command” is present, there won’t be any confusion on who to alert in moments of duress.
  • Provide support and additional training. Empower your team with the tools for their own training. Again, this will aid with a sense of responsibility and purpose. Better understanding of the software, programmes or work processes will ensure unnecessary problems are minimised. The WorkflowMax support centre has a host of resources available to help with training and education, as will most other software applications. Our self-paced education courses are also a great place for staff to start. For more general project management and smarter working tips, tricks and tools – stay up to date with the WorkflowMax blog.

4 – Is communication open and clear?

I’m a big fan of open communication – and the good news is it’s SUPER easy to implement in your business. All it takes to create an open and transparent culture is the DESIRE to do so. Start with the easy wins first – and watch how the culture snowballs. Once great communication protocols and tools are established, you’ll be sure to always have heads up when there’s a problem on the horizon.

  • Have an open door policy. This more personal approach transcends all forms of online communication. In most offices today the old “cubicle” is extinct anyway – but just by being more ‘approachable’ you’ll make a huge difference to team morale.
  • Encourage regular updates and reviews. Ask your team regularly whether there are any problems areas to be aware of and make sure they know you have their trust.
  • Provide updates on progress. For example, if there is a current issue, make sure the response and management of it is visible to everyone. This could be on your intranet, or company-wide chat network like Yammer.

5 – Are you keeping up with new technology?

It’s time to talk about the dinosaur in the room. Don’t let outdated methods of communication stall your progress! Using a robust project management software like WorkflowMax will give you visibility over your project from end to end and help minimise potential issues. Tools like the WorkflowMax Collaboration Manager aim to make collaboration within a project easier as well. If most of your problems are arising due to remote working (and you’re using WorkflowMax for your integrated project management needs) make sure your team has access to the WorkflowMax iOS app which can help you work better on the go.

A few weeks ago we profiled The Ultimate List Of Apps For Working Remotely – it features a host of great communication tools you can implement if you’re finding your current processes lacking!

6 – Can you pinpoint and prioritise the problem?

When faced with multiple challenges, you’ll need to rank in order of priority the most pressing issues. With limited resources and time you can’t manage all problems all at once. Think about what the opportunity cost is and which issue(s) will have a greater impact if unresolved. There are plenty of prioritising methods you could use – including the 3-strike system or the traffic light (red, orange, green) method for prioritising tasks.

7 – Do you trust your gut?

In Gavin de Becker’s “The Gift of Fear” (a great read by the way) he encourages us to trust our intuition. Best selling author Malcolm Gladwell brings up a similar concept in “Blink”. The point? Recognise the warning signs and have faith in your own assessment. After all, you’re a highly trained professional with skills honed by years of experience. Your instinct counts for something.

Even if a roadblock delivers a blow to project, buffeting the team sideways and inhibiting progress from what was forecasted – at the end of the day, you need to trust in your vision of the project. Action is what moves any project forward. Assess your options, come up with more options. Roadblocks can often lead to unexpected and creative solutions. It might be a great opportunity to take a step back and try a new approach.

8 – What learnings can you apply for the future?

So you’ve just finished that project riddled with roadblocks and problems, and probably never want to hear of it again. Completely understandable. But before you write it off, take a moment to reflect on it – both the good and the bad – to figure out what could be done better for next time.

  • Analyse and ask the hard questions; Was the roadblock a one-off or have similar problems been cropping up across the board? Was it an internal issue (and therefore controllable) or extraneous (and likely to be uncontrollable)? Knowing where the trouble is coming from means you’re one step closer to knowing what can be done better for next time.
  • Get critical feedback from your team. Were you able to control/manage the roadblock effectively? Discuss the outcome with your team and make sure everyone provides insight into how they felt it was managed/if they have any suggestions on what could have been done better. The goal is always looking back to look forward, i.e. no dwelling on negative outcomes, but improving for next time. Tools like Survey Monkey and Google Forms are handy if you want the feedback to be anonymous or more structured.
  • People > projects; Sometimes it’s way too easy to get so consumed by a project that it takes precedence over everything else. But ultimately managing your people is just as important if not more important than managing issues. Here at Xero for example, one of our values is #human reflecting the passion, energy and purpose every staff member feels in their day to day. And we try and make sure this value comes through in everything we do as a company!

So there you have it – eight critical questions you need to ask yourself to help overcome roadblocks in your project workflow.