If Strategic Planning Feels like This, You’re Doing it Wrong

Man at computer feeling frustrated because he's doing strategic planning wrong.

Generally, people have a baseline understanding that “strategic planning” and “goal setting” are valuable. But when it comes time to do these tasks, it’s not uncommon to feel some reluctance to take the time. There is so much “real work” to do!


The truth is, strategic work is the highest leverage work leaders can do – but it doesn’t always feel that way. Especially when the planning process isn’t optimized. If you experience any of the following reactions, there’s probably a problem with the way you are planning and goal setting.

“Well, that was obvious.”

Often the “strategic plan” basically amounts to “grow the company.” We already knew that was the goal. Writing it down doesn’t change anything.

“Isn’t this all arbitrary?”

To feel like we are doing strategic planning, we could try to set Key Results with numbers. “Grow Annual Recurring Revenue to 10M” sounds dandy, but isn’t it rather arbitrary? Why not 9M or 20M or 100M? It just feels like a finger-in-the-air guess at what might be possible if we’re lucky.


Sure, we can set a target. But then we’ll all just get back to work and what will happen will happen. It is impossible to predict the future, so what’s the benefit of trying?

“Have some respect!”

Often, one implicit rationale for goal setting is that it pushes people to work harder. But we’re already working crazy hard! We’re already highly motivated. We’re professionals. We don’t need an external motivator to make us work harder — and honestly, to imply that we do is a bit disrespectful.

“These goals have no teeth.”

There are hundreds of variables outside of our control. Are we really going to beat ourselves up if we don’t reach the stated goals? If not, what’s the point of setting them?

“It is just guess work.”

Our business is very dynamic. Unexpected opportunities come up. We’re constantly learning. A new insight could require a pivot at any time. We have to stay agile and responsive. We have to leave room for creativity and serendipity. Goals for 12 months in the future become obsolete the day after they are set! And then, no one looks at them again. The game plan is to respond to opportunities and customer requests as they come, so goal setting is a pointless exercise.

More meetings?”

We’ve got real work to do and can’t afford to take hours and hours to guess at the future. We just need to work hard and follow our instincts.

The way it should be

Planning and goal setting shouldn’t feel this way! If you have the right mental models, you can bypass the problems above and get a lot of value out of the process, even if you’re a small, dynamic startup. In fact, it’s precisely because busyness can overwhelm and the unexpected will happen that having defined strategic goals is so crucial. Clear goals provide a sense of stability and calm amidst the storm of startup life.


"Plans are useless, but planning is indispensable." - President Dwight Eisenhower


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