Don’t Bite Off More than You can Chew

Strategic Planning is certainly a meaty topic and can often seem like an intimidating undertaking. Approaching the process intentionally can save you headaches in the short and long term and will result in a much more cohesive execution.

We’ve distilled our best tips for effective strategic planning into 6 easy-to-swallow pieces to get you started.


When it comes to strategic planning…

Don’t bite off more than you can chew

It’s no secret that organizations that create and execute better strategies are more likely to succeed than those that do not. If your organization is looking to improve the effectiveness of your strategic planning process here are a few ideas to consider.

Stay connected to your raison d’être 

Although there are certainly differences between “Core Purpose”, “North Star”, “Mission”, “Vision”, or the myriad of other foundational statements organizations create; for the purposes of strategic planning, it matters less about which ones your organization uses, and more that you make them central to your strategic planning process.

There are all kinds of great arguments for having foundational statements and many other great arguments as to why you should incorporate them into your strategic process. I’m only going to focus on one here, because I’ve found it effective in convincing those who dismiss this type of work as “touchy-feely nonsense” to give it a try.

The argument relates to Peter Drucker’s famous quote, “culture eats strategy for breakfast”. It’s very effective at communicating Drucker’s overall idea but would be more accurate if written as “culture can eat strategy for breakfast”.

Incorporating your foundational statements into your strategic process is a risk mitigation tactic that reduces the likelihood that you will attempt to enact a strategy your organization does not have the appetite to execute.

Staying connected to your organization’s raison d’être not only reduces the likelihood of your strategy falling flat, but ultimately helps you build a culture of strategic execution. Make sure your strategy stays off the breakfast menu!

Have an off-site retreat

It probably won’t surprise anyone to see this one on the list. The reasons for opting for an off-site strategic retreat are straightforward: getting away from the office reduces the number and frequency of outside distractions, allowing participants to be more focused and mindful of the task at hand, while also providing an opportunity for some additional team building.

Having seen, and/or participated in strategic planning carried out in pretty much every conceivable way, I’m firmly of the belief that having an off-site retreat is worth the headache it takes to make it happen – aligning and clearing schedules, dealing with the inevitable backlog of issues upon return, along with the additional logistics. It’s a lot to ask of senior leadership (and their admin support).

The potential upside is immense. Every game-changing idea I’ve come across during strategic planning sessions has occurred during an off-site retreat. That isn’t to say you cannot have a good strategic planning process without an off-site retreat because you definitely can. But why settle for good, when great is possible?

Utilize an outsider perspective

No matter how diverse the thinking amongst your senior leadership team (and if you are being honest with yourself, you’d probably admit there’s opportunity for improvement) there are inevitably some common experiences and other factors that result in potential for biases and group think to limit the value you generate from your strategic planning process.

Why not inject some more diverse thinking by having an outsider participate? Having someone with very limited knowledge of the business, but who can ask great questions, (and isn’t afraid to ask the tough ones) is invaluable.

The simplest way to benefit from an outsider perspective is to use a great external facilitator. Besides dealing with meeting logistics, making sure that everyone is heard, and capturing key discussion points, a great facilitator will ask great questions, and challenge participants to expand their perspective on what is possible, which is well worth the cost of admission.

Avoid the long-term thinking, short-term focus problem

Most strategic planning processes use either a three- or five-year planning window (with a heavy emphasis on what needs to be done in the upcoming year). There are certainly good reasons (and supporting evidence) for thinking long-term. However, one area where even the best strategic planning process stumbles is post-retreat.

You’ve just returned from your off-site retreat with a plan that is going to ensure that your organization continues to thrive. Despite your enthusiasm to get to work on implementing the plan, things just happen slowly. You’ve got to address the backlog of the work (and fires!) that resulted from going on the retreat in the first place. Plus, there’s the regular day-to-day tasks and whatever else is happening at work and at home. Sometimes there are process delays (board approval or another internal validation mechanism is postponed).

It all seems perfectly reasonable in the moment but outside of a brief burst of energy in the beginning it is slow going and before you know it two or even three quarters have gone by, and now emails are bouncing around about preparing for the next annual strategic retreat.

You whole-heartedly believe in the goals and objectives of the plan, so you and your team roll up your sleeves and get to work. And do you know what? You do a remarkable job!

Sure, you didn’t completely get everything done that you wanted to, but you mostly did mostly everything (with “mostly” occasionally doing some heavy lifting). Best of all, the results are pretty good too! If only you’d been able to get started earlier, the results would have been even better.

The good news…you are not entirely to blame! If we are given a week to accomplish a task, most people, more often than not, will do the vast majority of the associated work on the Friday. If we have a month? Then we do it in the final week.  And what happens when we have a year? You guessed it, the majority of the work will take place in the final quarter.

The same holds true for groups as well, and although I’d love to be able to wave a magic wand and solve procrastination issues for us all, that’s not realistic.

Hold yourself accountable

What is realistic is exercising some control over the window we give ourselves to get things done. Near the end of your next strategic retreat, after you’ve settled on your main objectives for the up-coming year, spend a little extra time talking through what you want to (realistically) achieve in the next three months.

If your organization does agree to set some quarterly targets be sure to set a strategic check-in for the three-month mark. Inviting your “outsider perspective” person to the meeting will add an additional level of accountability (even if they have no formal organizational power) and helps ensure people are executing the strategy.

If you feel like your organization is nimble enough, don’t shy away from having monthly targets, with associated monthly check-in meetings.

Be aware of meeting creep; if you are meeting more often, shorten the length of your meeting. Keep the focus on what you have done since the previous meeting and what you are planning to do by the next one.

With practice and intention you can drastically reduce the duration of strategy check-in meetings while maximizing their ability to drive execution.

Long-term thinking about long-term thinking

In the end, strategic planning is likely something your organization will do for as long as it is around, so you might as well take a long-term approach: Do not burn out your strategic process (and the people who do it) by trying to implement everything all at once.

The goal should be to build and refine your process over time. Look to improve at least one (and not more than three) thing(s) about your strategic planning process and the execution of your strategic plan each time you start a new cycle.

If you’d like to try out something from the above, but you are worried you’ll have forgotten everything by the time your strategic planning cycle starts over again, why not set a calendar reminder and come back to revisit?


Have a question about your strategic planning process?  Let’s talk about it!

About Shane: A member of our Stratford Management Consulting team, Shane supports our clients in their Strategic Planning, Change Management, and Organizational Review work.

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