4 Questions to Jumpstart Your Strategic Planning

Originally published on February 11, 2011. Updated on October 6, 2021 for relevance.

Strategic planning is the first step in creating a competitive edge for your business. Understanding what's happening in your business, how it's positioned in your market, and what obstacles lie in the way of your success are critical if revenue growth is your goal.

But what does it mean to do strategic planning well? 

Is it about meeting structure or location? Hello, corporate retreat to Hawaii...Is it about gathering the right minds and decision-makers? Is it about learning from past mistakes or casting a brighter vision? 

And of course, how do you make your strategic planning productive and actionable? 

Strategic planning is one of the cornerstone services we provide here at Value Prop for B2B business owners who are looking for more revenue growth.

And today we're going to share the framework we use when facilitating strategic planning sessions.

What Makes for Effective Strategic Planning?

Many companies will approach strategic planning rather linearly. They set a lofty yet attainable goal for next year's growth and work their way back. The result is a clear-cut "First we'll do this. Then we'll do this. Then we'll do this" strategic plan that looks great on paper.

And then life happens.

Everyone goes back to the daily grind of the business. The initiatives that had been talked about fall to the wayside. And the plan never gets executed as well as it had been intended to be.  

Why? It's not because of any laziness or lack of good intentions on the part of the leadership team. It's just that the plan was made in a vacuum—and didn't account for the messiness of running a business.

Planning for "The Gaps"

Former Avaya CEO Louis D’Ambrosio frames strategic planning this way: “We’ve established three key priorities: strategy, execution, and culture. What’s most important is the interrelations between the three.”

For a strategic plan to be effective, it has to be grounded in the reality of how your business currently exists and operates—from available resources and bandwidth to the experience and personality types of your staff. It then has to take into account all the "gaps" between your current reality and the goal you have set for your business.

We do this by asking 4 questions at each major initiative of your strategic plan. These questions help you break down and bridge the gaps between each phase of your plan—making it more realistic, actionable, and manageable.

4 Questions for Effective Strategic Planning

1. What major issues must be faced?

For each phase of your strategic plan, brainstorm with your team what issues would arise in implementation. These issues may be internal or external to your business—or may in fact be unintended complications of other parts of your plan.

For example, one initiative within your strategic plan may be to launch a new product. But doing so introduces a host of issues—maybe the launch will negatively affect a long-term partner because it has competitive elements within it. Or maybe you have limited resources to market this launch, so you'll have to invest them wisely. These issues don't necessarily hamstring your go-to-market efforts but they need to be considered and addressed.

2. What key decisions must be made?

All issues will require you to make decisions – even “do nothing” is a decision. So, break down these major issues into key decisions that need to be made while going to market. Frame the decision along with its stakeholders and its impact on the key factors in the overall strategy.

For example, you've foreseen that your launch will impact your long-term partner. You'll have to decide how you want to mitigate the damage, or if you want to continue the relationship at all. Play out the consequences of each decision and how it might impact the other aspects of your strategic plan. 

3. What information are we missing?

Once you've sketched out the issues and the potential decisions you might face, take note of what information you're missing that you would need to move forward. Often times plans can stall out because of a lack of clarity around key parts of a decision. You don't need to learn that information right then and there as you're planning, but you need to have a sense of how steep the learning curve might be. 

For example, you've decided one of the best ways to market your new product could be through high-quality explanation videos—but you aren't sure how expensive a videographer could be, or the best way to use and distribute the finished product. 

4. What expertise will we need to carry out this plan?

Along those same lines, take note of where there are gaps in expertise. Your team likely won't be able to execute the entirety of your strategic plan through their own know-how. Which issues and decisions might require a third party's support? 

When you can see these gaps in advance, you're better able to budget your time and resources finding those third parties—instead of being thrown off course, scrambling to find help, or giving up on an initiative altogether.

Planning for Success

Strategic planning, when done right, can be one of the most beneficial activities you can engage in for your business and team. When everyone is clear on what needs to happen (before you're even deep in the weeds!), your plan has a much higher likelihood of success. 

And of course, if you would like any support creating or deploying a strategic plan that will grow sales, strengthen margins, shorten sales cycles, and increase lead flow, learn about our Competitive Edge Program.