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Time for a Check In: Are Your Strategic Initiatives on Track?

By John Hamilton, Courtney Necessary, Zach Warrick

August 30, 2019

Much like resolutions for the new year, kicking off critical strategic efforts can be energizing, but maintaining critical momentum throughout the business year requires substantial effort. Scope creep, indecision, and change fatigue can sap both leadership and team productivity.

We offer the following three steps to maintain or recapture momentum to ensure strategic initiatives meet their goals, ending the year successfully:

  • Reassess strategies
  • Measure progress and calibrate expectations
  • Accelerate successful execution

Reassess Strategies

First, take the opportunity to reassess your organization’s goals and the corresponding strategies under your control. Are all initiatives still aligned with overarching objectives? Have there been inflection points, headwinds, or tailwinds that may force strategic shifts in the coming months?

If strategies are still directionally correct and business-critical — great! Moving forward, it will be important to continue measuring the status of these initiatives and preparing to drive success through the end of the year.

If fresh strategic initiatives are necessary to meet organizational objectives, competitive dynamics, or shifts in customer demand, make sure these initiatives are balanced against the existing strategic portfolio. The new effort must be clearly and transparently communicated and connected to overarching business objectives. Teams will quickly lose focus and enthusiasm if both the “why” and “why now” is not communicated.

In the rare instance that a strategic initiative is no longer deemed business-critical, it is especially important to honor the work completed and acknowledge the lessons learned along the way. This can smooth the way for transitioning teams to other efforts.

Measure Progress and Calibrate Expectations

You and your team likely have a reasonably accurate grasp on the overall success and pace of the various initiatives currently underway. It is important to be cognizant of year-to-date progress, however, in order to accurately gauge where the pace of progress is on track, as well as where efforts may have slowed as the year progressed. Work with your team to catalog successes, and — maybe most importantly — failures along the way.

If things are progressing at an appropriate pace and momentum is being maintained, then it is time to celebrate results, while reinforcing the overarching business case for the initiatives. If things are not going according to the plan laid out early in the new year, acknowledge it with honesty, empathy, and transparency. Your peers and team will respond to both clear expectations and acknowledgment for both successes and mistakes.[1] If mistakes are seen as opportunities for growth, it will increase teams’ overall openness to change, while decreasing trapped capacity.

Accelerate Successful Execution

In order to obtain momentum when executing on strategic initiatives, start with something counterintuitive: slow down and make sure there is alignment. Effective execution occurs when commitment to the goals and priorities being set (or reset) is clearly communicated.

Aligning your team will likely come easier to you at this stage, because expectations and priorities have already been calibrated. Once teams are aligned, leaders can rapidly set the pace of change and maintain momentum by tracking progress, celebrating successes, and consistently communicating across initiatives to keep teams on track.

Executing strategy is never easy. It can be messy, complex, and exhausting for you and your team. In order to maintain momentum and end your organization’s year successfully, now is the perfect time to reassess your strategies, measure progress, and align to accelerate successful execution for the long term.


[1] Edith Onderick-Harvey, “5 Ways to Help Your Team be Open to Change,” Harvard Business Review, 4/3/2019.