How to Run an Effective Project Planning Exercise

By: John Prichard

We’ve all been in planning meetings that have gone off the rails. Sometimes it’s a case of too many cooks in the kitchen. Sometimes team members walk away confused and unsure of their next steps. Regardless of what project you are making the plan for, the planning process is in some sense its own ritual that can suffer common pitfalls and benefit from proven strategies. 

With the right setup and preparation for your planning workshops, you can ensure nothing is left to chance and everyone knows why they’re there.

Before we look at the three stages of a planning process, let me start by saying that you, as the meeting planner, must know your purpose…and everyone else’s too. You need to have a goal for every meeting and only have the right team members in the room.

One of the most common issues I have seen in planning meetings is that team leads try to jump ahead. They’re ready to find solutions, but you won’t be ready for that until you’ve gone through the three stages: (1) gathering information, (2) negotiating and mediating conflicting priorities, and (3) making key decisions.

Information Gathering

Without having all the necessary data points critical to your project, you can’t skip ahead to making big decisions. This can sound like a truism, but too often there is a tendency to get the conclusion people want to have without doing due diligence. And since any such conclusion will be chock-full of unvalidated assumptions, you know where this leaves you and me. So avoid the temptation to skip ahead and go through the proper process. 

The very first thing you have to do is gather all the available information, without making judgments or worrying about influencing the outcome.

In the collection phase, your sole objective in any meeting is to intake information. Your role is to dig, to prompt people in each workstream for information about their role on the project. This helps create a scaffolding around the project and provides context as people provide information in real-time. It is often the case this forum is the first time different teams fully appreciate what their counterparts are doing, which is key to ensure any plan you create is internally consistent and integrated across teams. After all, planning requires a shared context, which this scaffolding can provide.

In these planning calls where you are solely gathering information, be as unconstrained as possible in your approach. Encourage team members to directly and clearly state their preferred tasks, deadlines, and outcomes. The more you stay out of their way, the better positioned you’ll be to lead future meetings where you’ll need to start facilitating compromises.

Fact-Finding in Action

Here’s an example. Let’s say you’re working with Business teams on a go-live plan. You need to gather all of their tasks, dates, and expectations regardless of other competing priorities you might be hearing about elsewhere.

You can look at the business processes in the last months before go-live and collect data on what needs to be done for the first time after go-live. This involves multiple workstreams and is a huge collection project, but doing so helps team members define and compartmentalize different parts of their processes, and they’ll feel like you speak their language if you understand what they do.

Let’s consider the other side of the fence, an IT plan. On a given project, you will have other systems besides the one you’re working on, such as manufacturing, product lifecycle, master data management, ERP, CRM, et cetera. 

Taking an unconstrained view of gathering any and all relevant information about how those systems work, who does what, pain points, watch-outs, external events, etc. can help you understand how those system requirements fit into go-live and the overall architecture. Different satellite system and technology teams have their own service levels, resource constraints, and release schedules. Get the facts first and avoid the temptation to jump to solutioning or updating your plan. There will be plenty of time to line up schedules and see what conflicts need to be addressed.

Negotiating & Mediating Conflicting Priorities

Once you have all the necessary data points, your goal is now to refine what you have and review with other teams. If the collecting phase was taking a snapshot with an uncritical wide aperture lens, this phase involves sharpening your focus and making some decisions about what information takes priority. That means combining several plans or making modifications. Above all, your objective is to make sure all views are being represented accurately, and each team’s needs are considered when arriving at a consensus.

There will be disagreements in this phase. Your role is to act as the mediator and/or cheerleader, depending on how intense the disagreements get. When two workstreams’ schedules are at odds, you’ll need to work with them to find a schedule that works for everyone. When an opportunity arises to “do a deal” between teams, be a cheerleader for finalizing what you can. If you’re trying to keep the peace, that will inspire others to do so too.

Practical Approach for Conflict Mediation

Do what you can in advance to avoid arguments with a little “shuttle diplomacy”: have 1:1 sessions before the meeting to preview the content you need to make a decision on or that you expect to have a disagreement on. You want zero surprises. Anticipate where the conversation will take you and do your best to find common ground.

The more you have everything out in the open, the better the command you will have of it. And the more you talk to each team member, the less likely you will be to have surprises in the next planning meeting because you’ll already be aware of issues.

If there are issues, clearly articulate the area of disagreement. You should be the one to call out uncertainty so you can better facilitate the conversation.

A lot of the time, these disagreements are over small things. By bringing them up with the information you’ve collected, you can set the tone and model good behavior. This can set people at ease.

A lot of projects stay in negotiating purgatory forever because they can’t move on due to squabbles among team members. To avoid that purgatory, be just as direct and transparent about the decisions you’ve made as you were about identifying conflicts. Leave no doubt when conflicts have been resolved by clearly communicating and documenting outcomes. This is what you were doing all that cheerleading for!

Locking Down the Plan

Now that you’ve negotiated what needs to stay in the plan, your goal should be to move on. Put issues to bed. If you can’t, you’re back to negotiating. 

Help Deciders Decide

You may need signoffs on the final plan, and here’s another potential pitfall. People who have to decide or approve the plan need to know that they’re in charge of approving it. If they don’t, your job’s not done. Get affirmative confirmation that it is approved, and that means more than just a verbal “yep” on the way to the break room.

Get those deciders to agree in front of stakeholders who are waiting for approval to spend money on a project, go with one option over another, et cetera. You want them there to hear deciders say yes so they can move forward with their own plans. 

After consensus has been reached on a conflict area in a meeting, and all the stakeholders are aware that a plan has been reached, you should just be the happy helper with the clipboard checking things off as they happen. When there are no longer big decisions to be made, your role is to just make sure things get done. And yes, you may be seen as a pain in the neck! That’s okay if you can bias the conversation toward closure. Be a closer. Get it done.

But Wait, There’s More! Checklist for Better Planning Meetings

Simply breaking planning meetings down into collecting, negotiating, and deciding is a huge first step for many enterprises. Here are a few other tips to help make the process run smoothly.

Clearly Communicate Meeting Purpose

You will likely need multiple different meetings to get the whole plan put together. And every meeting is trying to get to a different outcome. It is imperative that you clearly communicate the purpose of each meeting in the invite you send. The same goes for your introduction when facilitating the meeting.

People are busy. If the purpose and agenda of a meeting are not communicated well, they’ll show up for the wrong meeting or skip one they need to attend. Being clear helps set expectations and boundaries, and ensure the right people show up for the right meetings.

Have the Right Audience

Every meeting you have should include people with expertise and people with authority (these may not be the same people). People who have the information you’re talking about need to be there to confirm any information you may not be as well-versed on, and people who have the authority to approve the information need to be there to do so.

People want to invite their whole teams but I have to tell you: some of the best planning sessions I’ve been in include just the lead of a workstream and one or two key resources. The worst thing to do is to move forward with a planning session missing the right people, and including the wrong people.

Get Key People Involved

Be sure to call out key people where needed. If you have your main decider and you need her in a meeting, call her out in the meeting. You can say something like, “let me know if this strays away from what you want” or “let us know if any of our statements are wrong or need to be addressed.”

You invited them there for a reason. Be explicit about what you need from them and make sure they’re actively participating in the meeting.

Be Ready to Rapidly Sketch Up Ideas

Having a physical illustration of what you discuss in a meeting helps people be more engaged with the content and remember it.

Whether you’re having an in-person meeting or a virtual one, use an appropriate tool to sketch ideas and take notes. That might be Mural, OneNote, Excel, or pens and a whiteboard.

Whichever tool you use, it needs to physically separate different parts of the discussion. Don’t just create one giant list of everything discussed. Create a parking lot for open questions for those who couldn’t attend. If you use a whiteboard, create a column of follow-ups to the right of the main list. Make it physically distinct from the notes you’re taking on the left.

Don’t fear “white space;” it can be helpful when people have ideas they can’t articulate. Open the white space for them to work on their ideas. If you don’t have space to react to conversations in the meeting, you’re not doing a good job.

A note on getting value from digital collaboration tools. Digital tools like Mural are wonderful for enabling collaboration in a virtual environment, or in some cases, to act as a digital whiteboard. But any tool is only as useful as the knowledge and ability to use it effectively. If you are planning on using a particular digital tool, invest the time to have your tool operator truly learn its features, shortcuts, and limitations so that it can be used smoothly without disrupting the flow. There is nothing worse in breaking the flow of good ideas than stumbling through an application or watching someone trying to format or struggle to capture people’s ideas on the tool. 

Be the One Who Sends the Recap

Don’t just assume everyone walks away from a meeting knowing what their next steps are. In most cases it is best to assume the opposite, just to be on the safe side. That’s the purpose of the recap; it should cover exactly what was decided and who’s in charge of which next steps. You also need to recap what wasn’t discussed or what needs to be followed up on. 

It’s your role to record history in the form of meeting notes. If you surrender that power, you surrender your value as the arbitrator of truth of what has happened and what needs to happen next.

The Moral Of The Story: It Is Best To Plan For How to Have Effective Planning

While project planning is about planning for the project, planning for those planning meetings can make the entire process go more smoothly. Just remember: each meeting needs to have its own focus, working through those collecting, negotiating, and deciding phases, rather than jumping into decision-making in the first meeting.