Most strategies miss the 'overcoming obstacles' aspect

In my 8 years of penning strategy documents, I’ve consistently tripped over the same stumbling block. Projects fell short due to mismatched expectations, missed deadlines, and teams pulling in different directions. Why? Because we neglected to address obstacles and strategies for overcoming them.

I became aware of my flaw after diving into “Good Strategy, Bad Strategy” by Richard P. Rumelt. But, I never got around to integrating these valuable lessons into my strategies. Until now.

Strategy is framed as ‘the actions to take for a specific outcome.’ What’s misleading about this is the tendency for the strategist to sketch out the ‘best case’ steps. “We’ll do this, then that, and finally this.” But what if this goes sideways? That’s the question we rarely tackle.

However, obstacles and their solutions are key to any solid strategy.

For example, here are several obstacles from a recent project:

• It was not clear whether we could easily transition from the old system to the new–we were winging it.
• Having just one domain expert on the team creates a bottleneck, impacting decisions and specialized issue resolution.
• Hot-fixes for key customers mess with our release schedules and development flows.
• Our software has a range of product types and modules, complicating life for both our teams and our customers.

Chances are, while reading these obstacles, you started thinking of possible solutions. That’s good. But remember, you’ll need to align with your team on these.

Having written these down has another benefit. It allows you to iterate on the resolutions. Answering the question whether the solution to an obstacle was the right one.

Once you start applying this in your strategies, I’d wager you’d be way more aligned and far more likely to reach your objectives.

Don’t forget to update your document with obstacles you run into. For alignment sake, and for future reference (don’t make the same mistake twice).