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If Strategic Planning Isn’t Improving Your Executive Team Culture, You Aren’t Doing It Right

Strategic planning can and should be an integral part of improving your executive team culture. Yet few executives see it that way. You hear “strategy” and you think “boring.” But strategy and fun absolutely can go together—and when they do, it brings your executive team together. The key is understanding these five truths.

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Strategic Planning Team Culture

Executive Summary

  • Strategic planning is an opportunity to impact the culture of your team. Don't just plan on how to plan, but plan on how to be together.
  • Planning without exciting energy flowing in from your company's Vision is a missed opportunity. Intentionally incorporate your vision into the exercises to remember where & why you are going.
  • Reluctance to planning may actually be reluctance to strategy. Make sure you are aligning properly with your executive team on the strategic core of your planning first.
  • Strategic planning is only as good as the diverse inputs each executive gathers. Make sure to tap every inch of your available resources.
  • Sharpen your language with your team to better align. Planning and strategic planning are two different things.
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Ecommerce Consultant Yates Jarvis

Yates Jarvis

Principal, Charleston

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#1

Strategic planning can be boring or exciting

Most executives don’t value strategic planning. They might value the idea of strategy, but see the process itself as a bother, a necessary evil. Especially for execs fresh out of middle management, strategic planning can seem so far removed from the day-to-day that it doesn’t seem to matter.

But how you present strategic planning, how you prepare people for it, and how you facilitate it (whether that’s you or a third party) can make all the difference between a ho-hum slog and an exciting, transformative event.

It starts with the why. What outcomes do you want from strategic planning? One outcome I encourage every business to add is, “Our strategic planning improves executive team culture.”

Once you’ve got the why, think about the how. How can the way we strategically plan improve our executive team culture? What would that look like for your team? There’s no right answer here. As leaders you will set the tone, so come prepared to model the behaviors that will make strategic planning enjoyable and stimulating. If you aren’t sure what this could look like, try different things, like starting the day with a team exercise, and learn from them.  

Finally, promote your strategic planning meeting. Buildup is key to making anything exciting. Just like a concert, a sporting event, or a grand opening, it takes planning and promotion to get people excited.

Ask Yourself

What role can I play in strategic planning? How will we get people excited?

#2

Strategic planning can be tedious or groundbreaking

When strategic planning feels tedious rather than groundbreaking, it’s probably because your business doesn’t have a high-level, bold vision. (Small visions lead to small outcomes.)

If you don’t have a high-level vision, you’re unlikely to have a true strategy either. Without a strategy, you’re not doing strategic planning—you’re just planning.

Strategic planning is how you carry your strategy down into the operations of the business. It’s how you make strategy come alive. That should be groundbreaking because you’re setting a course for growth and prioritizing a significant level of investment.

When it comes to a company surviving shifts in the market, strategy involves a pivot. If your organization spent all year growing apples, and now the strategy is to grow oranges, that’s groundbreaking and exciting. But to the people on the wrong end of the pivot, it’s also frustrating and scary. They worked so hard in one direction, and now your strategy is turning the ship in the opposite direction. These people may fight to keep your strategic planning more iterative than innovative. Resistance can signal that your strategic planning is on the right track.

Ask Yourself

Are our desired outcomes groundbreaking or just tedious? How does our strategic planning connect to our north star?

#3

Strategic planning can be confusing or organizing

You may think your people are aligned around your strategic plan. They may even think so. But inside themselves, many are game for the plan only to a certain degree. An indicator of this inner diffusion is when confusion or unresolved arguments arise in meetings. You try to pull people together, thinking they’re aligned around your strategic plan, but they’re really only aligned partially or not at all.

Sometimes it’s not about whether people like the new direction or not, it’s about “Does this threaten my ability to be me, here?” It’s scary for people when the new strategic plan goes against the only way they know how to do things. They’ll feel down on themselves and scared that maybe they’re not a good fit for the company anymore. Outside, they say they’re on board with the changes; inside, they’re determined to just keep doing what they already know how to do. They may fear that asking for help is showing weakness, feeling that this is the last thing a shifting company will want to see from them when it’s “all hands on deck.”

Part of our job as executives is to anticipate this about people. Be intentional and plan ahead. Anticipate areas where new capabilities must be developed and build that into the strategic planning. Lead with new capability development so people can see upfront how they’re going to be supported through the changes. Show them how learning new things will enhance their value—not just at this company, but also in the future.

That approach changes strategic planning from confusing and scary to organizing and exciting. It’s all in how the executive presents the context.

Ask Yourself

What new processes and capabilities must be developed? What resistance can we expect? How can we set people up for success?

#4

Strategic planning can be out of touch or in touch

Most execs do very little preparation for a strategic planning meeting. They have a specific line item in the budget that they want to increase; they’re just trying to grab their “nut” and run with it. But that approach won’t advance your strategy. Organizational strategic planning can devolve into only being siloed planning, which often looks like a post office with reports being dropped off to be delivered to the higher-ups…and very little above-department synergy.

Your strategic planning can and should be influenced by the ideas and the perspectives of people all around you. It’s essential to get the input of non-executives, particularly when the strategic planning is going to affect people’s jobs day-to-day. If the executive isn’t in touch with the opinions and perspectives and ideas of others, the strategic planning will be out of touch, too.

You don’t need to implement every suggestion, but you do need to listen and keep an open mind. (Here’s the best way to do that.) This approach allows you to bring a whole bag full of ideas to your strategic planning meeting.

Ask Yourself

What work did each executive do in preparing for this meeting? Did they talk to people and get outside perspectives? Who did they tap?

#5

Strategic planning can be dysfunctional or healthful

Ideally, strategic planning promotes a healthful team culture. But if you’re just planning while thinking you’re doing strategic planning, you’re not only wasting time, you’re inviting all kinds of dysfunction.

You’re perpetuating dysfunction in the priorities, the investments, the efficiency of the organization. Beyond that, you’re enabling dysfunction in workplace relationships. If your team doesn’t share the strategic vision, if people aren’t on the same page in terms of strategy, they’ll end up staying in their safe place and continuing to do what they’ve always done.

When strategic planning flows from a real vision and strategy, it builds commonality. You gain a real understanding of where the team is going and why. The team realizes they really are a team, and they stop working against each other. That’s a healthy relationship.

Ask Yourself

Is our strategic planning based on a strategy shared by the team?

Strategic planning is one of the most useful assets in an executive’s toolbox. Done right, it not only makes strategy come alive, but it also breathes new life into your executive team. Is your strategic planning exciting, groundbreaking, and unifying, or boring, confusing, and dysfunctional? The choice is yours.

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