Planning Tips: 34 to Get Things Started on the Right Foot

January 6, 2017 Marcus Varner

by Marcus Varner

Planning: you either love it or hate it.

On one hand, you have the people who obsess over planning, right down to the sub-sub-sub-task. They cling to it as a means of gaining some semblance of control over things that are, too often, out of control.

On the other hand, you have people who regard planning as a nuisance, either as a impediment to the "real work" or as a something toxic to creativity and free thinking.

Somewhere in the middle, you have the large majority of people who do it out of necessity, regarding as the responsible, reasonable thing to do, without having any special affinity for it.

The funny thing is, no matter what your stance on planning, our plans have a tendency to fall through. 'Twas President (and once-General) Dwight Eisenhower who echoed this sentiment:

"In preparing for battle I have always found that plans are useless, but planning is indispensable.” 

In other words, while most agree that planning needs to happen—and we do it dutifully—we almost universally find ourselves throwing our hands up when another plan goes awry. Just in case you think failed plans are a personal problem of yours, consider these stats:

Yes, we all know that planning is important, but it also looks like we're doing something wrong when it comes to planning. And it's costing our organizations dearly. Enterprises without effective planning processes are susceptible to several serious business risks such as lost productivity, delayed time to market, and slow decision making. They tend to be reactive rather than optimized.

Fortunately, you can change the way you plan, making it easier while vastly improving your plan's chances of success. Here are 34 tips to plan better:

1. Make the time to plan 

I know. We shouldn’t have to say this. While it’s the most important part of project management, sometimes the planning phase draws the short straw. Often less time is given to planning than any other part of our work.  “It takes a significant amount of time and energy to work through all the details and requirements in order to reduce the risk of rework and possible trouble later after a project has commenced. For this reason, it is said as much as 70 percent of a project manager’s time should be spent on the planning phase,” writes Moira Alexander at CIO.com.

Hala Saleh, senior global project manager at Expedia, echoes this sentiment:

"Most of us, regardless of whether we are in marketing or not, end up just kind of picking up work and doing it. Once we receive a work request, we tend to skip the planning phase and just go right to execution, which is a shame. After all, it’s the planning phase that gets you thinking, asking critical questions, and having discussions and conversations."

2. Separate planning from strategy

Creating and implementing a business strategy isn’t the same thing as planning and executing a project that supports that strategy. You need one before the other. Robert Sher at Forbes writes:

“Strategic planning must have its own place on the calendar, separate from operational planning. Leaders should collect, research, discuss, clarify in print then select the big initiatives before the annual operational planning process begins. Quality strategic decision must be made, then and only then, followed by quality operational planning to implement them.”

3. Make an outline

When a project feels overwhelming to plan, you can start with a basic one-page outline first. Jay Bacrania, CEO and Co-founder of Signet Education and Entrepreneur.com contributor, suggests creating a document that concisely answers the following questions:

  • What problem will the project solve?

  • What is the benefit to the organization?

  • What kind of staff and budget do I need?

  • What are the major milestones?

  • What are the potential stumbling blocks?

  • What risks does this project pose?

  • What is my work plan (list of tasks or sub-items to be completed by when)?

  • What are the specific metrics for success?

  • How will you know the project is done?

4. Identify stakeholders

To make the most complete plan, you need to know who else will be involved beyond the person requesting the work. This means any and all stakeholders, team members, and customers, etc. This will help you develop a plan that takes a variety of needs into consideration and could prevent scope creep or changing requirements down the road.

5. Create a brief

If your project falls under creative or marketing work, use a creative brief to hone the project planning details. Only 23% of in-house teams use briefs for all projects which is surprising since, without a brief, reworking design or copy multiple times is inevitable and time consuming. Use a template and make it a part of your creative project planning process and you will cut down on approval and rework time remarkably. Most professionals agree that standardized processes, such as templates, equal greater success rates.

If you need a little help getting started on creative briefs, feel free to use our free template.

6. Use a project definition document

This document contains the crucial project details. Once approved by stakeholders (internal and external), it becomes the bible for how the work is to be done. Tom Mochal at TechRepublic writes that the project definition document is the key deliverable during planning and should include the following:

  • Overview

  • Objectives

  • Scope

  • Assumptions and risks

  • Approach

  • Organization

  • Signature page

  • Initial effort, cost, and duration estimates

7. Set realistic expectations

Almost nothing is as frustrating as when someone over-promises and under-delivers. To combat this, everyone should explain, listen to, and be clear about any limitations of the project. Setting expectations together with stakeholders eliminates surprises and frustrations down the line when it’s more expensive to fix them. Simon Andras at LifeHack.org says that forgetting this step set only sets you up for project failure. “Don’t begin your project with failure nearly predestined,” he writes.

8. Talk about tradeoffs

In the same vein as setting expectations is talking realistically about what can and cannot be done. Or if it has to be done, what other requirements or work will need to wait. Are they willing to sacrifice some scope to hit a deadline? Or are there must-have scope items that allow for an adjustment of the deadline? Pushing a deadline out or delivering under scope can be okay if you understand what is most important to the stakeholders and they buy in on the tradeoffs.

9. Identify risks up front

When the planning work is occurring, the project team should identify all known risks. Mochal writes:

“Some risks are inherent in a complex project that affects every person in the company. Other risks may include not having the right level of expertise, unfamiliarity with the technology, and problems integrating smoothly with existing products or equipment.”

10. Give your projects a start and end date

This may seem like a “no doy” sort of situation. But you’d be surprised how often companies don’t plan project start and finish dates. Having firm dates allows you to prioritize them effectively. “Start and end dates will also allow you to plan around your own business cycles and prevent projects from going on for much longer than they should,” writes Bacrania.

11. Hold a kick-off meeting

kick-off meeting is a critical opportunity to make sure everyone is on the same page before you start. During the meeting you should align on the project details, schedule, expectations, tradeoffs, and decide how to communicate during the project. This is done with all key team members and stakeholders. "When people work on the same project but have different notions for what the goals are, what their roles are, and how or why to help each other when things go wrong, it creates the friction that makes projects fail," writes Scott Berkun, best-selling author on business productivity.

12. Make a communication plan

How you will communicate project details throughout a project or job is another critical part of the planning process. Moira Alexander at CIO.com writes:

“Ineffective communication may seem harmless, but when it comes to projects it can be one of those areas where a single word or gesture can set up a chain of events so disastrous it can completely derail an entire project.”

A communication plan includes how and when you will get approvals and move things forward as well as delays, issues, and roadblocks will be communicated and handled. According to a post on project management in The Harvard Business Review:

"All customers want their jobs finished on time and on budget—or preferably faster and cheaper. But if they can't have that, and sometimes they can't, what they really want is to be kept informed along the way. Share bad news as well as good so they're never outraged by enormous last-minute changes."

13. Then centralize communication

Having a communication plan is definitely crucial. Planning communication methods and means will save you a lot of time and headaches during the work. So, how will you do the communicating? Through hundreds of emails and chat conversations? Sure, these have their place. But a large project can quickly throw your inbox into chaos. Consider using one hub where all updates, feedback on projects, alerts on roadblocks, and more can be viewed and replied to.

14. Automate communication

Now that you have your communication planned and centralized, it’s time to figure out if any of it can be automated to save time. If you use a hub where communication is centralized, it should also have features to automate most of the repetitive messages like task completion, changes to due dates, and approval notifications.

15. Document the workflow

Understanding all the steps involved in getting a project from start to finish (i.e., your workflow) is also critical to planning. Now, we can’t give you a template to follow for every project because everyone’s workflow is unique to how they get work done in their environment, on their team, at their company. Fortunately, it’s not hard to start making this a part of your process, and documenting your own workflows is as close as your next project. Click here for one example that describes creating, publishing, and sending an email notification for a blog article.

16. Optimize the workflow

Now that it’s documented, you can look for ways to improve it. What works and what doesn’t? Gather your team and get their feedback, with answers to:

  • We changed our workflow in these specific ways, A, B, and C. What about those things that we implemented or put in place worked really well?

  • What isn’t working really well and why?

  • Is it a problem with the process step? Or is it a problem with not understanding how to execute it?

Once you get the answers, you can focus more time and energy on the things that work and redevelop and redefine those that aren’t.

17. Create a schedule

Using your start and finish dates as your guide, create a schedule for how each part of the scope will be completed. You did all the pre-work and planning up to this point so you have minimized the chances of failure. Creating a schedule for pieces of work to be done but remaining flexible within the scope and timeframe could take the edge off your frustration when change requests start to trickle in.

18. Break things into manageable chunks

If creating a schedule for the entire scope is making you want to scream, try breaking work into smaller pieces. This allows teams to uncover, evaluate, and correct estimates made about the larger scope of work.

19. Define project management processes

You have a lot of planning in place but may want to determine how the team and project manager specifically will interact throughout the work. What methodology will you use? How will the team will manage issues, scope change, any risk, challenges with quality? Mochal writes:

“It is important to be able to manage the project rigorously and proactively and to ensure that the project team and all stakeholders have a common understanding of how the project will be managed.”

20. Appoint a backlog manager

How will you know what to plan next? Often which project to do next is determined by which department or executive is screaming the loudest. However, if you really want know what is best to tackle next, it's important to have someone responsible for managing your backlog of requests. In marketing, this could be the content marketing or creative director, if you're on a small team. If you have more headcount to work with you could assign a senior designer or writer. For other departments you may assign it to a traffic manager, project manager, production manager, or resource manager. This person will be the gatekeeper. It is their responsibility to assign priority to requests based upon company and business goals as well as any specific standards your team agrees to. Having someone in this role protects the rest of the team’s time. It also let’s others know exactly who to talk to about their requests and project statuses.

21. Decide where to store project files

Part of planning means knowing where everything will live. It's important to store documents, images, and files in the same place such as your work management platform. Wherever it is, make sure all files available to all team members, stakeholders, managers, and executives.

22. Plan your team resources

With some research, questions, conversations, and digging, find out who is available to work on the project. One way to fail before you start a project is to not know the workloads or the status of current ongoing projects. Once you know who is overloaded and who might be available, review the scope and schedule to help prioritize team availability.

23. Select team members and assign responsibilities

Once you have an idea about the availability of human resources, make sure that each person is assigned work based on skill-sets that align with requirements and roles for the work. Andras writes:

“If you assign the wrong person to a task, you are reducing your chances of success before the project even begins … Make sure each team member is clear on what is expected from them and when.”

24. Establish measurable and reportable criteria for success

We can all appreciate knowing what a win looks like. Part of the planning phase should dedicated to defining success and how to measure it. Will it be hitting the deadline on time? Will it be finishing 99% of the scope? Something else? Once you know you can create your schedule with more confidence and include specific milestones for reaching success. “PMOs and senior executives should quantify the success rates of projects in relation to company wide objectives and determine what changes may be required for future projects to keep the business moving in the right direction,” says Alexander.

25. Look at project risks

A lot of potential risks will surface when you define the project details. Taking it a step further, you will need to have a plan in place for specific occurrences. There are no alarms or flashing red lights if the project is in danger of failing so having a contingency plan at the beginning will be your best bet. “If you can see when a risk is imminent, you can take preventive action to avoid it, or you can quickly step in with corrective measures if necessary. Be ready to halt a project if the risk becomes unacceptable,” says Andras.

26. Consider setting up a PMO

Trained project, program and portfolio managers have vast knowledge, skills and experience. If your company continues to struggle with project or other work completion, consider adding a PMO or EPMO (Enterprise Project Management Office) within the organization. Alexander writes that this is to ensure all teams only initiate projects that provide the organization with benefits and should be mapped directly to company-wide strategic objectives.

27. Get the bigger picture

The best planners have the widest and most informed view of the company as a whole. If you find yourself in the dark often about what the company’s goals are and how your team can make a difference, request to sit in on or be involved in executive planning sessions. To get buy in, Alexander writes that you can “highlight how this will help to establish a shared vision, as well as reduce the risk of missed objectives and misunderstandings, while increasing the projects [sic] chance of success.”

28. Break teams into smaller groups (if needed)

If the planning the project feels out of control, try breaking the work down into focused tasks for smaller groups. “Once we were over 10 people, the development team had trouble with communication, and we were slow and inefficient” says Aytekin Tank, founder of JotForm, a leading online form builder. Once teams were realigned and smaller, each focused on one single issue. “Our teams became much more focused and agile again. We got work done faster and better again,” Tank explains.

29. Be authentic

When you, as the planner, are guarded or difficult to work with, it makes the whole project suffer. This doesn’t mean you pretend to be nice or happy all the time. People appreciate honesty and authenticity when it’s respectful. Frustrations will show but if you, as the project leader, try to be transparent, objective, flexible, and accessible it will go a long way in completing the plan and the project.

30. Resolve issues as quickly as possible

Challenges will surface during the planning and execution of projects. If issues crop up during planning, put some effort and urgency into finding a solution fast. Hold a quick sync meeting, if needed, and refer to your project details that everyone signed off on. Use that as the source of truth to find a solution.

31. Plan to succeed

With a mindset that the project will succeed, unexpected surprises won’t derail work. A well-thought out plan that focuses on the highest value activities can go a long way toward setting expectations you are confident you can meet. Even if/when surprises arise, your plan will position you better to adapt.

32. But know when to quit

You gave your plan your all, but it’s just not coming together. What then? It’s hard to quit, especially if you’ve already put time, energy, and emotion into planning or even working on the project. Bacrania writes that if a project—and we would add planning—is dragging on, there are some questions to help determine whether or not to abandon it. They are:

  • Is the goal of this project still important to my organization?

  • What was the planned ROI for this project? What is the ROI now?

  • What is my opportunity cost in working on this?

  • Could we better achieve my goals by spending this time on other projects?

  • What is the emotional or company culture toll of continuing with this?

33. Evaluate projects when they are done

This is important because it will help when you plan your next project. Do a “post-mortem” on finished projects. Doing this, says Andras, allows you pinpoint what could or should have been done differently and helps establish best practices for use in future undertakings.

34. Use a system to plan and prioritize your work

Work management is complex. If you’ve read this blog at all, you know we are big fans of automating everything you can. But there are still an overwhelming number of people who are making work more difficult for themselves and their teams. In research findings from Business Improvements Architects, only 32 percent of respondents said they had a process for prioritizing projects. In the same study, 68 percent of organizations said they had no systematic approach in place to prioritize projects or link them to corporate and strategic goals.


So what other tips would you give to create and carry out the perfect plan? Tell us in the comments below.

About the Author

Marcus Varner

Over the last 9 years, Marcus has worked in every type of content—from writing to video production to design—and is currently a senior content marketing manager at Workfront. His focus is always on breaking through the clutter while engaging audiences with brands' most foundational messaging. He currently oversees all corporate- and awareness-level level content at Workfront.

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