The Power of Regular Strategy Checkpoints

With 2025 well underway, it’s the perfect time for business leaders to pause and reflect on any strategic planning efforts for the remainder of the year ahead

Developing a solid strategy is one of the most challenging and critical responsibilities a leader has. However, the process doesn’t end once the strategy is set. Regularly reassessing, reevaluating and adjusting your plan is essential for staying on track and ensuring success.

Your yearly strategic planning provides the opportunity to identify key goals, define metrics for success and outline the actions needed to reach those objectives. While it sets the direction, it’s the ongoing checkpoints throughout the year that help leaders gauge if they’re headed in the right direction or if a course correction is necessary.

Here are some key questions leaders should consider when reassessing their strategy, to determine if they’re on track or if changes need to be made:

Have the Goalposts Moved?

At the outset of your strategy, you defined a clear end goal. However, it’s important to ask: Is this goal still relevant? The business environment can change rapidly, and priorities may shift based on market dynamics, customer needs or internal challenges. By regularly revisiting your end goal, you can ensure that your strategy remains aligned with the current landscape. If there have been significant changes in the industry or within your organisation, this pause allows you to adapt and redefine what success looks like for the rest of the year.

What Are the Losses and Wins?

One of the most insightful questions to ask is: What’s working and what’s not? This requires a deep dive into both new initiatives and ongoing strategies. What new actions or tactics have you implemented this year? Which ones have produced the desired results, and which have fallen short? Likewise, reflect on past initiatives that were successful – are they still as effective, or have they lost their impact over time? By recognising both your wins and losses, you can build on successes and pivot away from strategies that aren’t delivering. Seeking diverse perspectives, whether from team members, customers, or external advisors, can offer valuable insights to adjust your approach and better meet your goals.

Can we Simplify the Vision?

As strategies evolve, they can often become over-complicated, making them difficult for teams to follow and execute effectively. Is your plan still clear and easy to understand? What may have started as a straightforward vision can become a complex web of tasks and objectives, which may leave your team confused or overwhelmed. It’s important to simplify your strategy whenever possible, focusing on the most critical goals and ensuring that everyone is aligned with the bigger picture. A clear and concise strategy not only helps in effective execution but also motivates employees by giving them a sense of purpose and direction.

Are we Staying Ahead of the Curve?

Staying in tune with the external environment is crucial, especially as market trends, customer behaviours and competitor activities evolve. Is your strategy still aligned with your customers’ changing needs? As consumer expectations and market conditions shift rapidly, strategies that were once effective may no longer meet your audience’s demands. By regularly incorporating external insights into your review process, you can ensure your strategy remains both relevant and competitive.

Regularly reassessing and adjusting your strategy is key to staying on course, especially in an industry like workplace supplies, which is constantly evolving and full of innovation. With new products, sustainability initiatives and emerging workplace needs continuously shaping the landscape, these moments of reflection ensure that your strategy remains aligned with the changing dynamics of the industry.