Why Challenges to Your Strategy Are Actually a Good Thing

Strategies are often decided by senior leadership and handed down the ladder. As we’ve discussed in previous articles, when higher-ups make crucial decisions in isolation, those on the receiving end feel disconnected from the process.

Without any attempt at collaboration, people are unable to truly own and execute the strategy. Another unfortunate consequence of top-down strategic planning is that it creates a sense of finality—that the plan can’t be challenged, reconsidered, or revised.

A good leader should be approachable and make sure their team knows that the strategic plan isn’t infallible. It can and should be challenged, tinkered with, tweaked. Creating space for such challenges leads your team through the constructive cycle outlined above, fostering valuable contributions and enabling true engagement with the strategy.

Here are three reasons why the process of challenging is critical:

  1. It builds comprehension of the strategy. Challenging something, questioning it, and discussing it are vital parts of the learning process. If you and/or your team think that the strategy is a done deal and not open to questions or challenges, you may actually have a harder time understanding it.

  2. Being able to challenge the strategy actually builds ownership. The real or perceived inability to question the strategy leads people to disengage. It cultivates, in effect, a sense of powerlessness. Feeling powerless is a real obstacle to being able to connect with what you’re doing well enough to either execute it properly or find fulfillment. So when you allow feedback and challenges to the strategy, people engage in new ways and take ownership more readily.

  3. Challenging can be both productive and satisfying. Once again, people not only want to be heard, they also have good ideas and knowledge of trends, perceptions of processes, and other information that can enhance the larger strategy. When you encourage the challenging and questioning of the strategy and truly listen to feedback, you expand your perspective which can only benefit your plan.

Understand these factors and including an opportunity for people to productively challenge the strategy will results in a strategic plan that is that much more robust, thorough, and exciting for everyone!


Weekly Uplevel Practice

To cultivate an environment of collaboration and connection (and break that cycle of top-down strategic planning), create opportunities for your team to engage with the strategy.

  • Allow them to review a draft of the strategic plan. Make sure they know it’s a work in progress.

  • Solicit questions and challenges to the strategy. Invite feedback and take it seriously.

  • Zoom in. Create a portion of the plan that’s specific to your team and how they personally will implement it.

Broadening your approach to strategic planning in these ways produces a professional environment with more engaged employees, more prepared leaders, and a more effective strategy to move into the coming year with confidence.



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