Strategic Dinner Reservations

I was out to dinner with my wife a couple of weeks ago, and she mentioned how it was relatively easy to get reservations, via the waitlist, at good restaurants. It turns out that many people make reservations before they have solid plans and then cancel them. 

That reminded me of a conversation I had when I was a young analyst at McKinsey. My team was working on an engagement in New York City over Valentine’s Day, so I asked one of the team associates, Jim, whether he had plans. 

He said, “Kind of. I have a dinner reservation, but I don’t have a date.” I gave him a puzzled look, so he explained, “In New York City, the reservation is harder to get than the date.”

I had always considered Jim’s quip a funny anecdote, but telling Erin that story made me realize that “the reservation is harder than the date” is also a basic framework for strategic planning.  

When I talk to nonprofit leaders about whether they need a strategic plan, I usually start by saying, Maybe. 

The extended answer starts with distinguishing between having a strategy—the logic of how the organization is going to get from where it is today to an attractive strategic destination—and a plan, which is the detailed timing of the various parts of the strategy. 

Organizations and teams definitely need a strategy, but a detailed plan in addition to the strategy is vital only when there’s a can’t-miss milestone or a hard-to-secure resource. 

I was writing this post while watching the USA Track & Field Olympic qualifying trials, which are a great example of a can’t-miss milestone. It’s not good enough for an aspiring Olympian to declare an ambition like clocking a world-class time in their event. Their training plan needs to reach that goal on a specific date and time. Otherwise, all the work almost doesn’t matter. 

This dynamic exists for organizations whose timing is driven by fixed-date milestones like government budget cycles, elections, and graduation season for hiring. 

However, for most organizations and teams, developing a plan precisely articulating when every strategy step will occur is less useful. First, the future is unknown, so the plan is almost always wrong. More importantly, the time and effort to develop that plan can often leave a team in thinking mode for longer than needed rather than shifting to doing mode, where there’s far more valuable learning. 

Planning is similarly important for hard-to-find resources like a Valentine’s dinner reservation in New York City, or scarce human resources, or major donor gifts in the nonprofit sector. In those cases, developing a plan that clearly identifies that tackling those critical path items first is useful. 

Some of my clients' strategic plans sound like, “Write a compelling fundraising pitch for the amazing project we want, but wait to figure out the details until after someone writes us a large check.” That’s perfectly fine. Similarly, “First hire a talented executive to drive the effort, and then let them develop their plan and hire the rest of the team” is also reasonable. 

This approach to planning is useful because it shifts the strategy effort more quickly into action—e.g., the fundraising, the hiring—rather than keeping it in a less productive thinking mode. Of course, figuring out the details of a plan will eventually be important, but the details are rarely necessary before taking the first step.

Leadership Wisdom 

“Walter Kiechel [...]  once pointed to a study suggesting that only 10% of formulated strategies actually got implemented (a figure Tom Peters called ‘wildly inflated’!). Such concerns have led to huge efforts by senior executives to clean up implementation. ‘Manage culture’ or ‘tighten up your control systems’ they were told by a generation of management consultants. After all, the problem could not possibly reside in their own brilliant formulations.

“So when a strategy failed, the thinkers blamed the doers. ‘If only you dumbbells appreciated our beautiful strategy …’ But if the dumbbells were smart, they would have replied: ‘If you are so smart, why didn’t you formulate a strategy that we dumbbells were capable of implementing?’ In other words, every failure of implementation is also, by definition, a failure of formulation. But the real problem may lie beyond that: in the very separation between formulation and implementation, the disassociation of thinking from acting.”

— Bruce Ahlstrand, Henry Mintzberg, and Joseph Lampel, in Strategy Safari