Planning for Extraordinary Results: The 3 Components of a Winning Plan

By Alex Shootman | CEO at Workfront

Note: This post pulls from Done Right, a leadership book from Workfront CEO Alex Shootman.

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“Forget about asteroids coming out of the sky to end civilization as we know it. ... When you’ve done this project before, what’s most likely to go wrong?”

That’s how veteran project manager Eric Lucas kicks off his team’s planning for the next big job. “I usually start by asking the people who have done this before to tell me what are the most probable problems we’re going to experience,” says Eric, PMO Manager at Crowley Maritime Corporation, a marine logistics and transportation business based in Florida.

“By focusing on probability, I minimize the number of people who say, ‘Well, if I die in a train wreck and I’m not here, then …’.”

If there’s more than a 50% chance of something happening that will slow progress or swallow more resources, Eric and his team come up with a contingency plan.

It’s an antidote to expansive planning, which is the tendency in business to try to predict and pre-empt every possible eventuality, however unlikely. The result is that plans get bloated by ifs, buts, and improbable maybes. Time is wasted, and project plans become more complex than they need to be.

Eric’s approach is about narrowing the field of vision to what’s going to matter most. It’s about reductive planning, which is boiling plans down to actions not options.

Three essential ingredients of reductive planning

So, instead of worrying about what likely won’t happen, the focus of planning should be a simple guiding question: How are we going to get this done — and done right?

Reductive planning has a bias towards action and the practical steps your team will take to achieve organizational goals.

To make a success of reductive planning, you need three ingredients: key initiatives, milestones, and best next actions.

1. Key initiatives

Your key initiatives are the small number of most important items that will allow you to achieve the results you’re seeking. They're akin to Pat Lencioni’s defining objectives, and they might be intended to improve the operational efficiency of the business, fuel innovation, address challenges from competitors, or adapt to changing market conditions.

To help identify possible key initiatives in your business that would make the most difference to customers, coworkers, and financial stakeholders, use the wisdom in the room. Find answers from your team members by systematically asking how these constituents see your company today and how you hope they will see you tomorrow.

At the heart of this exercise is my belief that the answer to every question your business will ever face lies within the collective expertise and experience of your team. They know the answer; you just need to ask them the right questions to find it.

2. Milestones

Each key initiative breaks down into smaller actions called milestones. These are the trail markers of progress that show how far and fast you’re moving towards completion of each key initiative. To create milestones, ask, “If we did X, do we have a chance of accomplishing the key initiative? If not, what’s one more thing we need to do?”  

In my experience, key initiatives break into no more than four to six milestones. It’s important to note that milestones are tasks, not time. They are the big steps that your team needs to complete, and your team will probably work on them simultaneously rather than in a linear, one-after-the-other sequence.

3. Best next action (BNA)

There are a couple of questions that great leaders ask their teams to keep everyone focused on what really matters:

• “What are we going to do next?”
• “What’s the one thing we’re going to do within the next two weeks that will take us closer to a milestone?”

These two questions have a bias towards action rather than indecision. You’re not asking for answers with multiple options. You’re asking everyone to focus on understanding the single most important action right now.

Put those three elements together and you reduce planning to actions rather than infinite or improbable possibilities.

Save the sweat: Aim to barely accomplish

A closely related symptom of expansive planning is the tendency to try to ace every task — to give everything 110%. That’s 10% wasted time and energy.

Instead, your team’s aim should be to barely accomplish tasks. Get them done, but only by expending the time and energy that’s required to get it done right — and not a drop more sweat.

When your team is focused on barely accomplishing tasks, they will get more work done, much more quickly. Creating a culture of barely accomplishing tasks is a key way for leaders to help their teams maintain the right direction and momentum towards key initiatives.

Decision-making rules

There’s a final lesson to learn from Eric Lucas’s planning playbook: approach problems with a decision-making framework, not rigid pre-conceived answers.

When things go wrong — and no plan will ever quite be delivered to the letter — you’ll need to make good decisions quickly.

“As the project manager, I can’t make decisions for everybody on the team,” says Eric, “But if we agree upon a set of rules by which the decisions will be made, then I know when we take a first and second punch, we’ll make decisions in a coordinated or predictable way.”

Above all, remember two key lessons running through this argument in favor of reductive planning: it’s knowing and doing just enough and always focusing on actions rather than options. Hemingway once wrote, “Don’t confuse motion with action.” Right now, there are only two questions you need to ask yourself: What will you do next? How will you barely accomplish it?

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Read more about Done Right.