Without a clear consensus on the destination, a project will be hard pressed to get you from A to B

Project Planning: Where Managers Go Wrong

How to get a project started without losing your mind

Sean Conner
Unexpected Leadership
9 min readFeb 27, 2017

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For many managers, work is a series of projects. Some of these are concrete, such as Hire X person by the end of June, but others are not so easily understood. Suppose we had to Create a training manual for marketing team members. We know to expect a manual, but what will that look like? Will it be bound and printed? Will it be a word document on some server? Or a wiki site? And what will be in it? Just the processes? Or will it explain how to master all that the marketing team does?

With a project such as this, chances are everyone involved will likely have their own picture of success, and this upfront ambiguity is one of the most pressing hurdles for a manager to overcome when starting to dive into a project. There’s a lot of thinking that can go into how to actually approach the task at hand, such that sometimes you’re left without much time to do the work itself. The aim of this post is to help shorten this window while retaining clarity for all involved. To do that, we’ll explore a framework from author David Allen, then put it into practice with a simple worksheet.

David Allen’s Natural Planning Model

Allen is the author Getting Things Done and founder of the GTD movement, a productivity methodology. One of the many things he presents in the book is the Natural Planning Model, a means to capture what humans naturally do when they hope to accomplish anything. Whether we’re trying to plan a night out or implementing a new CRM, Allen asserts we move through the following five steps when approaching a project:

1. Defining Purpose and Principles

2. Outcome Visioning

3. Brainstorming

4. Organizing

5. Identifying Next Actions

Let’s illustrate this with our example of planning a night out. It’s Friday and you’re heading to work, thinking about what you want the evening to have in store. You decide you want catch a movie and dinner with friends. In doing this, you’ve defined your purpose. Next you’ll unconsciously determine principles, what Allen calls “boundaries to your plan.” This could be the people you want to invite, the quality of the restaurant, the time of the movie, or how much money you’re willing to spend. Then you’ll probably start picturing the evening itself — drinks over spicy Thai food and something funny on the silver screen. You might even imagine all of you laughing at some joke as popcorn spills from the tub in front of you. This is outcome visioning. “Whereas your purpose was the why of your going out to dinner, your vision was an image of the what,” Allen says.

With this vision of your evening, you’ll then begin brainstorming. Should you send a text or call people? Should you make a reservation? Should you see that new Amy Poehler movie? Should you buy tickets in advance? Such questions are “part of the naturally creative process that happens once you commit to some outcome that hasn’t happened yet,” Allen says. “Your brain noticed the gap between what you were looking toward and where you actually were at the time, and it began to resolve that cognitive dissonance by trying to fill in the blanks.”

This commences the how phase of our night out, and once you have posed the unanswered questions, you start to organize them. You might think, “I should send out an email to coworkers seeing who is interested,” or “I better find out movie times to be able to make a reservation.” You are breaking down the project into what Allen calls “components (subprojects), priorities, and/or sequences.” Components would be things like inviting people, picking a movie and time, and choosing the restaurant. Priorities would be things like, “I have to know who can come ASAP.” And sequences would be, “I’ll invite people, then pick a movie time, then book a dinner reservation.” Finally, with this all organized, you’re ready to identify your next action, the first thing you must to do take a step toward the outcome you envisioned at the beginning — Send out an invitation to friends.

This is a relatively basic illustration of the Natural Planning Model — you probably wouldn’t have to write anything down to successfully execute your night out with friends. But what’s helpful here is to understand the natural flow of project planning, because for whatever reason, when you jump into the workplace, what’s natural and what’s normal rarely align. Allen proposes, and I agree, that in fact, the opposite is often true. Let’s imagine your team is in the midst of an initiative that’s way off track. You realize this, and the first thing you’re liable to do is try to step in and organize all activity. When you realize that the approach to the work is off, you start brainstorming. Then when that 30-minute brainstorming session fails to generate progress, you might pause and consider what outcome this initiative is trying to accomplish. And if that answer doesn’t come easily, you might step back and wonder the purpose of the project in the first place.

See what happened there? Our planning model flipped.

This isn’t to say that many of the projects we undertake begin in this way. Many follow Allen’s Natural Planning Model at the start. But due to their complexity, or the passage of time, or the lack of an agreed upon expectation of the finish line, we drift, and as we drift, we lose focus. Three months later, we’re left wondering why a project didn’t turn out quite the way we expected.

Understanding the Natural Planning Model is a good first step toward avoiding this, but I find the framework needs something to give it wheels, which is why I want to share a simple worksheet that can help put the framework onto paper so it can be seen, understood, and agreed upon by all. Meet the Measurable Accountability Plan, or MAP (here’s a copy for you to download).

At Guerrero Howe, we work on a quarterly cadence, and we use the MAP to capture our major goals for the next 90 days. The tool was introduced to us by Rom LaPointe, founder and CEO of Capricorn Leadership, who in turn got it from the Entrepreneur’s Organization. MAPs help us succinctly capture our understanding of a project in one place. As we go through it, you’ll notice elements of Allen’s Natural Planning Model flowing into place. And though you can fill out a MAP by yourself, I find it’s helpful to tackle it with two or three others that will be part of the project, as it will let you generate ideas you wouldn’t have thought of on your own. So grab some of your peers, a conference room with a whiteboard, and let’s get started…

Write the Goal

To begin, write the goal of your project. Keep this to a sentence at most, but try to make it as concrete as possible. Here are some examples of weak vs strong goals:

Hire 5 people vs. Hire 5 sales associates by June 15

Establish new brand identity vs. Establish brand identity and integrated marketing plan for new service line

Create 5 Case Studies vs. Create 5 Case Studies and implement on website and in sales process

Draft a description of the project

A good description should succinctly answer the why (purpose) and what (outcome visioning) of the project. Think of it like the project’s elevator pitch: two to three sentences you’d say to a colleague if they ask what you’re working on. Don’t worry about nailing it on the first pass. You’ll refine it when you complete your MAP.

Articulate how the project aligns with company objectives

Next you need to clearly state how this aligns with your organizational goals. This is a good smoke test to ensure you’re in lockstep with your company. If you can’t easily nail this, the project might not be worth doing. On the other hand, avoid aligning with too many priorities at once, as it will likely result in mission creep. Specificity is key here.

Define key strategies

Skip the metrics section and jump down to key strategies. Here’s where you’ll outline some core principles and start brainstorming how you will accomplish the project. Key strategies are your guardrails, defining what you will and won’t do. For your MAP, these are either things you need to get done or things that define your approach.

Things you need to get done are subprojects. If you’re hiring a new team member, these could be things like write, approve, and post the job description or Determine interview team and responsibilities.

Things that define your approach are Allen’s principles. For a marketing project, this might be Get team members talking to customers to understand their perspective or Survey staff for feedback.

Create Action Steps

Now it’s time to organize and plan next steps. Action steps document how you’ll carry out your key strategies. Action steps aren’t meant to record every small detail, but should provide high-level milestones to direct your efforts. I like to challenge project owners to keep the total number of action steps to less than 15, even for hairy projects.

Each action has three components: a description of the action, an owner, and a due date:

Action: This describes what exactly happens at each step. It should be clear, such that you can easily say it is done or not done.

Owner: This is the individual who will be accountable for this step being completed. Only one name can go in this box.

Due Date: Action steps need deadlines, so put the specific date you need it completed under the respective 30-, 60-, or 90-day column.

A few other tips to consider when drafting action steps:

  • Post-its and a whiteboard are a nice way to map out adjacent project sequences. Give each key strategy a Post-it color, then map out the steps needed to accomplish it. Then you can mash the Post-its together and refine due dates and steps.
  • Good action steps capture outcomes, not activity. They should give the step’s owner the autonomy to tackle the step how they see fit, which is a great way to develop team members. You can then have conversations with them about how they approached the task, what worked, what didn’t, etc.
  • Avoid assigning deadlines and owners until you’re done mapping out all the steps. Then you can have individuals claim steps that they’re interested in.
  • Less is more. There have been many times when I tried to lump in pet initiatives into a project scope, only to ultimately bite off more than we could chew. So try to capture only those actions that you must complete in order to count the project as successful. Chances are you’ll generate a lot of other improvements as you progress, and lumping in extra stuff at the start can lead to stress and scope creep.

Define Metrics

You’re now ready to set metrics, which are a means to measure components of a project so that you can say you accomplished what you wanted to. Metrics are an easy way of knowing, when the project is due, whether you followed through or not, so you can avoid confusion around what you agreed to all those months ago.

Don’t stress out about these needing to be “critical business KPIs.” Metrics can also be divined through your action steps. Maybe it’s the number of meetings held with leadership, drafts of a plan, or customers interviewed.

Do a final pass and distribute

With metrics defined, do another pass with your team to make sure your description makes sense, action steps are aligned and assigned, and metrics are in order. If everything looks good, get the MAP in the hands of any action step owners for their sign off. Once they’re good to go, it’s time to start rolling.

That’s how a MAP can help you put Allen’s Natural Planning Process to paper. The tool takes practice, but an honest attempt will give you line of sight into a project’s details, including the most important element: why you’re doing it in the first place. Keep it close and may your next project shape out the way you intended.

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