SME Strategy Leadership, Management and Strategy

Organizational Strategic Planning: What It Is and What It Takes To Be Successful

Written by Anthony Taylor | September 23

Organizational strategic planning is a strategic planning process that brings in leaders beyond the executive team, usually your top 20 to 30 people, so everyone understands where the organization is going and how their role contributes. The plan gets executed at the organizational level. It should be built there too.

I've run hundreds of strategic planning processes over 16 years. Most of what follows is what I tell CEOs on the first call.

What the executive team misses when it plans alone

Your executive team will talk about the strategic plan constantly. That's their job. The second-level manager is a different story. They spend roughly 80% of their time in operations mode, and unless someone builds in regular reminders and context, the plan fades into the background by spring.

Earlier today I spoke with a leader who wanted to solve a problem in three months. It had been building for three years. Different regions, functions, and countries had each developed their own understanding of what the strategy meant, down to the technical terms they used for the same work. Nobody was trying to derail the plan. They just read it differently, and nobody had closed the loop on those interpretations.

That's the gap organizational strategic planning fills.

The picture on the front of the box

Imagine your team is working on a jigsaw puzzle together. It's much harder with no picture on the front of the box. It's harder still when everyone is holding a different picture.

When everyone has the same picture, people help each other find pieces. When they each have their own, they fight over pieces. That second scenario plays out in a lot of organizations, and it looks like turf battles, duplicated work, and budget fights.

The vision is the picture on the box. I start every process with one question: if success were a place, how would we know we'd arrived? If your team isn't aligned on where you're going, they won't be aligned on what it takes to get there.

Where organizations get it wrong

The most common mistake is building the plan in a room with a handful of people and then handing it down. Communication runs one way, and the people expected to execute it never had a say.

The second mistake is making the plan too complicated. If it took three days in a room to write it, it has to make sense to someone who wasn't there. Plans fail in one of two directions. Either they include so many initiatives that nobody can prioritize, or they stay so vague that nobody knows what's actually required.

The third is reviewing the plan once a year. A lot of drift happens in twelve months.

The ten-story building

Picture your organization as a ten-story building where every floor is a separate initiative. You have 100% of your time, money, and energy, which works out to 10% per floor. You make a little progress everywhere, you pay a switching cost every time you move between floors, and you finish very little.

I recommend a different approach. Pick a couple of priorities, get everyone focused on them, finish them, then move on.

Most teams are more aligned than they think

People expect the upfront interviews to uncover hidden problems. They rarely do. Leaders generally know where the tension is. What the process does is get those issues on the table so the uncomfortable conversations actually happen.

In most of the listening sessions I run, people want the same things. They just describe them differently. Our pre-planning survey asks fundamental strategic questions, and people answer the question itself rather than reacting to whoever asked it. A third-party facilitator helps for the same reason: the room focuses on the content, not the personalities.

By the end of a three-day session, there's noticeably more trust. That trust is what lets a team work through conflict and say uncomfortable things to each other, which matters far more than a team-building exercise.

Who needs organizational strategic planning

This process fits organizations with several hundred employees, typically in the $50 million to $500 million range, though the same principles hold at a billion. It matters most when you have:

  • Long-horizon projects, such as R&D, manufacturing, or capital investments in the tens of millions, where direction has to hold for years
  • A cultural change underway, which usually takes 18 months to three years because you're rebuilding the systems, structures, and processes underneath the culture, not writing new values on a wall

A $1 million or $2 million business is usually better served by a one-year tactical plan. Small changes move those businesses too quickly for a multi-year process to pay off.

How the process works

Pre-planning (one to two months). I interview your leaders, run stakeholder listening sessions, and send out a pre-planning survey. Each senior leader spends about an hour on pre-work.

Facilitated session (two to three days). We cover vision, mission, values, strategic priorities, goals, and tactics, and finish with clear measures and KPIs. If your team uses a balanced scorecard or OKRs, we accomplish the same thing under different names.

Written recap (within 10 business days). Your team gets the full plan in writing.

Execution (about two hours a month for 12 months). Regular sessions keep the plan in front of people and help untangle problems as they come up. An optional follow-up call covers what's going wrong in early execution.

I teach through metaphors like the puzzle and the building because your executives will have to explain the plan to their own teams afterward. You don't need an MBA or previous offsite experience to use what comes out of this. It's hard work, but people consistently tell me the three days go fast and they come out a better team.

What does organizational strategic planning cost?

Most CEOs come in expecting around $50,000. At SME Strategy, organizational strategic planning starts at around $25,000, and most engagements land between $30,000 and $40,000, depending on how much stakeholder engagement and facilitation you need.

We've run this process so many times that it's straightforward to buy. After a recent RFP, the client told us we'd made everything simple.

What happens after the plan is written

The first three to nine months are usually rough, especially for organizations that haven't built a habit of execution and accountability. That's normal. Each year of execution goes deeper. In year one you get aligned. By years two and three you're making the hard calls you avoided before.

Growing from $100 million to $300 or $400 million means more than adding sales. You need to build an organization that can support those sales, which means new systems, new ways of working, and stopping things you've always done. For clients who want ongoing support, our advisory services include leading monthly strategy meetings and coaching leaders.

Much of the value comes from the time spent stepping back to work on the business instead of in it.

Frequently asked questions

What is organizational strategic planning?

It's a strategic planning process that involves leaders beyond the executive team, typically the top 20 to 30, and builds in two-way communication so the plan reflects how the organization actually runs and the people executing it understand it.

How is it different from a leadership offsite?

An offsite involves only the executive team for a few days. Organizational strategic planning adds one to two months of stakeholder interviews, listening sessions, and surveys beforehand, then twelve months of structured follow-up afterward.

How long does it take?

About one to two months of pre-planning, a two- to three-day facilitated session, a written recap within 10 business days, and about two hours a month over the following year.

How much does it cost?

With SME Strategy, it starts at around $25,000. Most engagements land between $30,000 and $40,000, depending on how much stakeholder engagement and facilitation you need.

Who should be involved?

At minimum, your senior managers, usually 20 to 30 people. You'll also need a plan to cascade it to the rest of the organization with two-way communication.

Is organizational strategic planning worth it for smaller companies?

Businesses under a few million in revenue usually get more from a one-year tactical plan. The organizational approach pays off once you have several hundred employees, long-horizon investments, or a major cultural change.

Does this replace OKRs or a balanced scorecard?

No. The plan ends with measurable goals and KPIs, so it fits whichever tracking system you already use.

What happens after the plan is written?

The real work begins. Plan on regular check-ins for at least 12 months. Most organizations find that alignment deepens each year.

If you're planning a strategy offsite, I'm happy to walk through our process with you, whether or not you end up working with us. Book a conversation. If you'd rather run it internally, start with the One Destination Alignment Scorecard.