Project management secrets that drive project success

By - 27 May 2015

Two men and a woman in workplace casual attire in an office conference room

Starting a new project can be both an exciting and daunting prospect. It might feel like you’re drowning in a sea of documentation one minute, then the next you’re encountering project drought in a wasteland of unclear deliverables and erratic input from the client.

Here are some tools and activities I use across my projects that have helped me not only ensure that the whole team understands the project, but that I have all I need to run it and support the team throughout.

Be gutsy—Ask questions until you’re satisfied with the answers

I’ve learned to make the most of the small window of time at the start of projects when it’s acceptable to ask silly questions. This is the time when there will be gaps in knowledge about the client, the product, the timescales—and that’s OK.  Just be careful that you don’t repeat questions that the client has been asked before so they don’t have to repeat themselves.

You should also check to ensure that the answer isn’t hiding in any documentation that has already been shared. You may find that others on the team are thinking about the same thing but are too afraid to ask—so be gutsy on their behalf.

Feel empowered to clarify assumptions. I’ve found that most clients appreciate being asked thoughtful questions; it’s a sign that they’re working with an engaged team that has a genuine interest in how the client’s organization works.

Know what success for this project looks like

As part of the discovery phase on your project, make sure you know your client’s goals and objectives. Here are a couple of quick, simple activities you could run to start the conversation.

Make sure your client and your team are reading off the same page.

Bring your whole team and the client together to brainstorm the goals of the project, and then ask the client to prioritize the most important. This will uncover any misleading assumptions that could possibly derail the project’s success.

  • Draw a dartboard on a whiteboard or piece of wall chart paper.
  • Distribute post-it notes and a sharpie to everyone in the team, then set a timer for 2 minutes.
  • Get everyone to silently brainstorm what they think the goals and objectives of the project are.
  • Next, get each person to read their ideas aloud and pass them to the client/product owner to place on the dartboard. The more important the goal or objective, the closer to the bullseye. Limit the number of goals that can be in the first couple of rings to force prioritization of the most important objectives.
  • Transfer the goals / objectives that made it into the inner rings of the dartboard onto paper, and then put them on the walls for the team to refer to while working on the project.

Get clients to think about what failure and success would look like for this project.

  • Distribute post-it notes and a sharpie to everyone in the team, then set a timer for 6-8 minutes and get everyone to brainstorm the following:
    • What success for this meeting looks like
    • Success for the project
    • Success for the year ahead, e.g. impact of the project on the wider organization / business
    • “This project will be unsuccessful if…”
  • Have everyone elaborate on the reasoning behind their points
  • Remove duplicate post-its in each category
  • Group similar post-its and label those groupings
  • Discuss how you would tackle the raised issues that might jeopardize project success
  • Revisit early and often.

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Gamestorming: Great things don’t happen in a vacuum

Don’t hesitate to think outside the box and create innovative challenges. Stirring conversations that lead to new thinking and greater clarity not only enhance work on the task at hand, they also have long-ranging benefits.

Books like Gamestorming: A Playbook for Innovators, Rulebreakers, and Changemakers by Dave Gray, Sunni Brown, and James Macanufo introduce excellent techniques for uncovering insights, breaking down walls, and having more productive meetings.

Make use of existing materials

Are you rebuilding a website or application that already exists? Ask the client for a demo or a login, then set one of the team off on a challenge to record a screencast. This will give you a good idea of the current site structure and user flow, and will make it easier for you to visualise how the new application you’re going to build might hang together.

This will ensure the team has a shared understanding of what you’re building and what “good” looks like to the client. Be careful, though! It’s easy to get caught in the trap of designing or building what already exists, so question the worth to the user each step of the way. Just because it already exists doesn’t mean it’s being used!

Create a project glossary

If you’re working with a client from a specialist industry and they’re using terminology you’re not familiar with, I’d recommend starting a collaborative glossary. As you come across a tricky term, ask your client to define it, then keep the definition in a place everyone can easily refer to. Shared language improves the chances of success with any collaboration. This can also be a great way to quickly get someone new to the team up to speed. It’s very simple but incredibly handy.

Stick to your process

Run honest retrospectives regularly to expose holes in your process early. Actions can easily be forgotten between retrospectives and may be particularly hard to recall at the end of a project.

If possible, have your team create a working agreement and refer to it at the end of each retrospective. The principles could include the team’s objectives, such as happiness, pride in their work, professional growth, and so on. Ask everyone to plot how they feel the last sprint measured up against the agreement’s principles e.g. “how adaptable have they been?”. You can then easily see, at each point of the project, how people were feeling. The big picture will help you see how your process is holding together, and if changes should be considered.

Team retrospectives pentagonal rating system graphic

Credit: Sam Barnes

You’re all set

Next time you’re starting a project, dig out this post and try out some of the activities, tools and tips and let me know how you get on. My hope is that they’ll help empower you to navigate your way through your new project from day 1 to delivery.

What tools and activities do you use to make sure you and your team stay focused on the vision / goal of the project throughout delivery?

Holly is Delivery Lead at Deeson, Europe’s leading open-source software agency. She’s the founder of the UK’s largest digital PM Slack community and curator of Make Good, a bi-weekly newsletter for people who care about exceptional software delivery.