Against boring planning

What comes to mind when you hear the word “planning”?

If you’ve been in the tech world for a while, you might imagine long meetings spent on weekly tasks or quarterly roadmaps. You might think of agile, OKRs, and Gantt charts. You might recall time spent in ticket trackers and project management software.

In short, planning is often really boring.

This is made worse by remote work. In an office, it was those sessions in front of a whiteboard where the spark of an idea could happen. The thrill of building on each others’ knowledge, and putting together a collective view of what we want to accomplish. In the remote-first world, we’re stuck with Zoom fatigue and half-hearted attempts at async communication.

We’re here to argue that planning can and should be one of the most exciting moments in your week or your quarter. It should be a time when your team comes together, builds shared context, and gets clarity on priorities. It’s when you feel a sense of true teamwork, all being in the same boat together and rowing toward an inspired shared goal.

With the right kind of planning, you come out of the meeting knowing exactly how your work fits into the larger whole and feel excited for what lies ahead.

What is good planning?

In Meetings are the work, Elizabeth Ayer writes:

In addition to being social, knowledge work is also uncertain and messy. […]

Resist the urge to fill in the hunger for meaning with lists and tasks. […]

Shift personal development away from project management mechanics like backlog management or forecasting and towards knowledge and communication topics like facilitation, collaborative decision-making, effective writing.

As creative workers, we often find meaning in our work, and that’s how we create something great. We may come into a planning session with our colleagues with this “hunger for meaning” that Ayer describes, and this is precisely why it’s so harmful to fill that void with lists and tasks.

Methodologies like Agile, much good as they can do, also can get the attendees hung up on mechanics and jargon (backlogs, story points, etc) and lose the forest for the trees.

The Muse way ✨

On the Muse team, we’re passionate about all of the “thinking work” that goes into making a great plan. We’re building a tool that we hope, combined with the right mindset, can unlock this more creative and inspiring way for individuals and teams to plan their work.

We see the best approach to planning for remote teams as encompassing some of these principles:

1. Keep it high-level and open-ended

A planning session should be about hashing out tough questions and tradeoffs for the project. It should include everyone who works on the project and key stakeholders. The idea is to get on the same page about the most important questions.

Project timelines and sequencing is important, but this can be in a rough, back-of-the-envelope form rather than trying to estimate work precisely.

2. Planning is not a meeting

We believe in the hybrid model of group ideation. If participants come into a meeting with no prior context, you're already in trouble.

So “planning” is not a single meeting, but rather some offline idea generation and strategizing individually. The synchronous meeting is a convergence point, a chance for everyone to come together, to combine and synthesize the ideas. And a place to look each other in the eye and commit to the shared plan.

As a bonus to this hybrid model, you make the most of the synchronous time. That means shorter meetings and less Zoom fatigue.

3. Plans explain the "why"

The logistics are important: tasks, assignments, deadlines, sequencing. But these are all second-tier questions to the heart of plan, which is: why are we doing this?

This includes the context for the company’s current strategy, risks and opportunities in the marketplace, or unique capabilities on your team. It includes measures of success. For example, on a product launch: are we doing this to reach a new demographic of customer? Or to increase the number of customers in our existing demographic? Or to attract investment and hiring opportunities? The “why” beyond the “what” will affect which tradeoffs we make during the project.

4. Plans change

A common mistake is never revisiting your plan.

Once you dive into the implementation of a project, it’s easy to get lost in the day-to-day details of the work. The reality on the ground can and almost certainly is different than it looked from the bird’s-eye view of planning. If you or your team finds yourself getting confused, going around in circles, or just having doubts, it’s time to look back at your plan.

Sometimes, revisiting the plan will restore your clarity and help you get back on track. Other times, you realize that new information gained through the hands-on work of execution means the plan needs to change.

Either way, your team needs to work through this together before doing further work.

5. Be creative, expressive, and human

A good planning session is a chance to feel connected to your colleagues over this shared work you are all devoting yourself to. The artifact in front of you should be a place that’s creative, expressive, and inspiring.

Conclusion

Teams like yours continue to search for the best practices and tools to adapt planning to a remote world. But while we do that, on the Muse team we want to argue for rehabilitating the word “planning” from its connotations of drudgery to something inspiring that we all look forward to.

How does what we’ve described here match up with how your team plans its work? We’d love to hear from you in our community.