“The Women’s Edge supports systematic, sustained progress for women into leadership roles throughout the business community.”


Elizabeth Hailer, CEO

“There aren’t many places that you can go where the only agenda is for you to be successful.”

CEO forum member

“The Women’s Edge supports systematic, sustained progress for women into leadership roles throughout the business community.”

Elizabeth Hailer, CEO

Registration now open for Strategies for Success Program. Leaders from corporations and nonprofit organizations alike are encouraged to participate.



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“The Women’s Edge supports systematic, sustained progress for women into leadership roles throughout the business community.”

Elizabeth Hailer, CEO


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3 Steps for Successful Strategic Planning

All companies, whether big or small, should have some sort of strategic plan in place to help the organization identify and work towards its goals. For many, especially those running a startup or small business, “strategic planning” is a daunting phrase that can seem difficult to get off the ground.

We spoke with our experts Eileen Glynn, Senior Strategic Marketing Consultant; and Kendra Phillips, Chief Technology Officer and VP of New Products at Ryder System, Inc. to help us navigate the strategic planning process and ensure that it is a success.

1. Create Bite-Sized Goals

Often the most challenging part of the process is figuring out where to start and what a strategic plan for your organization might look like.

“When you look at a strategic plan,” says Kendra Phillips, “it’s normally a three- to five-year vision for the company and sets growth targets, like doubling revenue or obtaining X number of new customers. How do you take that and break it into yearly bits and pieces that gradually get you towards your goal? Break it into thirds for a three-year vision. Have it in bite-size pieces that you can achieve so it doesn’t end up getting put away in a drawer and never looked at again.”

When developing those goals, make sure they are measureable items that can be rated using a “pass/fail” system. Without measureable goals, there is no definitive way to determine your company’s growth.

“At Ryder, we use a tool called the bowling chart. It’s a template that’s available online, and we use it in Excel. We lay out our targets by month. Each one should be measureable—did we achieve it? Yes or no. There’s no yellow or maybe. It’s meant for accountability and driving results.”

2. Plan and Implement

As mentioned above, your plan won’t do you any good sitting in a desk drawer. So how do you find ways to effectively implement your plan and turn your goals into action items?

Kendra shares another tool called the X Diagram or X Matrix, a template available online. “This has been a game-changer in not just having a strategic plan, but figuring out how to execute to that plan,” she says. “The objective is to take your three-year plan and have three things that you want to achieve in three years. That’s one side of the X. Rotate the X. Next is, ‘What do I have to achieve next year to do it?’ Rotate it again and figure out what the actions are that need to be taken to achieve those goals. The last part is breaking down who owns that action. Put a name to who is doing the actions/tasks. Then you can break that action down into another X for that person.”

While large companies often have a dedicated strategic planning group, the same isn’t always possible for small businesses and startups.

Eileen Glynn states that “one of the issues sometimes is that companies aren’t big enough to have that strategic planning group. How do they take that information and really get people to think about the current and the future times? People who do strategic planning should also be involved in the implementation of it. Whoever is chosen to do it or is on the team will have that voice within the organization. People will really listen to them to figure out how to embed what they’re doing within the organization.”

3. Get Everyone on Board

The last piece of the puzzle is to have everyone aligned with the goals and action items in your plan. So how do you get buy-in from everyone involved?

“This might be the most important question,” Kendra says. “Buy-in is everything we do as leaders of a company, and a lot of organizations overlook it. Ryder has tried many things to get buy-in. Leadership does road show across country to meet with smaller groups in geographic areas and spends a half-day talking about strategy and how each piece fits in. This is done in order to listen and get questions from the group to obtain buy-in. Other things we’ve done have included video messages from the CEO and lots of internal news. The bigger you are, the harder that buy-in is. But it is something you absolutely have to focus on.”

Buy-in is equally important and can also be a challenge for smaller organizations, as Eileen explains. “Even for smaller organizations, to have the executive director and leadership board agree on a direction, and to get people aligned around the goals is very important. Whether you’re big, small, or medium, getting buy-in is the most difficult aspect of a strategic plan. Have it be a living document. Make sure everything that’s being done is measureable so you can see how it’s affecting the organization for the future.”

Bottom Line

Strategic planning is a necessary, albeit challenging task for organizations of all sizes. But with the right tools, team and mindset in place, it doesn’t have to be a daunting task.

Please join us for our next Just Ask TCI virtual discussion, which happen on the third Friday of every month. This program is free and open to the public and begins promptly at noon, ending promptly at 1:00 p.m. ET.