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3 Tips to Improve Strategy Execution with AI Assistance

Chris Wollerman

May 27, 2024

3 Tips to Improve Strategy Execution with AI Assistance

As a CEO for a large and small company for the past 27 years, I’ve discovered some useful tips for assuring our annual strategic goals are well executed or even better, over-executed. Before getting into the execution tips, there are a few important things to consider when setting up a strategy. It all starts with clear measurable goals such as OKRs that are well structured and communicated throughout the organization. There are many books, courses and consultants that can help with setting up a solid strategy, but the basics that we followed consistently for success were: 

  • Get feedback from everyone in the organization on improvement opportunities. We send out an annual survey with some simple questions around Strengths, Weaknesses, Opportunities and Threats (SWOT) and there are some excellent AI tools to help sort through the results for trends. Not only does this step present the executives with some good ideas, it helps everyone in the organization feel a sense of involvement and ownership.  Be sure to thank employees for spending their time on the survey, communicate the results summary and show where the executives plan to take action.  Show them during the strategy rollout at the beginning of the year and as you introduce new key results each quarter which company goals are based on their feedback. 
  • Involve all leaders to prioritize their team’s and department’s top initiatives from the SWOT survey, filtered by their part of the organization.  This also builds ownership and accountability.  
  • Use AI strategy tools such as Inspire to help leaders brainstorm for objectives and key results based on challenges in the business. 
  • Use a balanced scorecard approach to include goals for finance, customer, process improvement and culture.  Our overall approach is to ensure there is something for every employee to align to help move the organization forward.  Only a small portion of employees can contribute to the most common goals around finance but goals such as role-based learning and process improvement are something everyone can work on. 
  • Assign ownership of goals to executives and leaders one level below the executive team to ensure accountability for execution. 
  • Setup goals with both annual and quarterly key results to allow for course correction throughout the year. We’ve also been successful with trimesters instead of quarters at our large company but find the quarterly cadence works best for smaller organizations. 

The 3 categories of tips for execution are outlined as follows: Senior management reviews, Team cadences and 1-1 meetings. I’ll describe our best practices for success in each area in the sections below. 

Senior Management Reviews  

One of the most critical factors for effective strategy execution is the alignment and commitment of the senior management team. The senior management team consists of the executives (CEO, CFO, CTO, CIO, COO, etc.), Business Unit Leaders, and Department Directors.  They should meet regularly to review the progress of the strategic goals, identify any gaps or risks, and agree on the actions to take to address gaps/risks. The frequency of these meetings may vary depending on the size and complexity of the organization, but we found that a combination of short weekly reviews (15-30 minutes max), mid-quarter reviews (for course correction) and quarterly retrospectives worked well for us. The agenda for these meetings should include: 

  • Prepare for the review using AI tools such as Inspire’s Dashboard to establish a descriptive narrative that describes the changes in progress since the last review, key updates from contributors and insights on strategic alignments.  Consider using a tool like Microsoft’s Copilot for Power Point to automatically build a presentation that saves significant time in preparation. 
  • A review of the key results for each strategic goal filtered by the business unit or department, using data and metrics to assess the performance and impact.  Each business unit leader and director briefly present their high-level progress along with insights and actions for holding their teams accountable when progress is behind. 
  • A discussion of the main challenges and opportunities for each goal, and the root causes of any deviations from the expected outcomes. 
  • A decision on the corrective or preventative actions to take, and the assignment of responsibilities and deadlines for each action. 
  • A recognition of the achievements and successes of the teams and individuals involved in the strategy execution. 

The senior management reviews should be conducted collaboratively, focusing on learning and improvement rather than blaming or criticizing. The senior management team should also model the behaviors and values that they expect from the rest of the organization, such as transparency, accountability, and customer orientation. 

Team Cadences  

The next level of strategy execution is the team cadence, which is the rhythm and frequency of the meetings and interactions among the teams and departments that are responsible for delivering the strategic goals. The team cadence should be aligned with the senior management reviews and provide the opportunity for the teams to report on their progress, share their learnings, and get feedback and support from their peers and managers. The team cadence should also foster a culture of collaboration and cross-functional coordination, as well as a sense of ownership and empowerment. The team cadence may consist of several types of meetings, such as: 

  • Weekly or biweekly status updates, where all contributors on each team individually present their accomplishments, planned tasks, key results, challenges, and actions for each goal, and get input and guidance from their managers and their peers. We keep these to 10-15 minutes and use recordings with transcription and AI to help track action items. 
  • Quarterly reviews, where the teams reflect on their achievements and learnings for the past period and set their priorities and plans for the next period. 
  • Ad hoc meetings, where the teams discuss specific issues or opportunities that require immediate attention or collaboration. 

The team cadence should be designed to suit the needs and preferences of each team and avoid unnecessary or redundant meetings. The team cadence should also be flexible and adaptable and allow for adjustments and changes as the strategy evolves or the environment changes. The team cadence should be facilitated by the team leaders or managers, who should ensure that the meetings are productive, engaging, and respectful. 

1-1 Meetings 

The final level of strategy execution is the 1-1 meeting, which is the personal and individual interaction between a manager and an employee who is involved in the strategy execution. The 1-1 meeting is a powerful tool for building trust, motivation, and performance among the employees, and for ensuring that they have the resources, skills, and feedback they need to succeed. The 1-1 meeting should be held regularly, at least biweekly, and have a clear and consistent agenda around goal execution, such as: 

  • Prepare for the 1-1 meeting using an AI tool such as Inspire that will suggest coaching advice to the leader to improve the quality of conversations based on the updates of the direct reports.  Quality conversations will help build trust and engagement with employees. 
  • A review of the employee's tasks, key results, challenges, action items and development level for each strategic goal and a discussion of their performance and impact to the strategy.  The development level represents the employee’s confidence and competence for each goal and helps the leader best identify the level of direction and support to provideCheck out Ken Blanchard’s work on Situational Leadership for more insight. 
  • A feedback session, where the manager provides specific, constructive feedback to the employee, and the employee shares their feedback with the manager. 
  • A coaching session, where the manager helps employees identify their strengths and areas for improvement, and to develop their skills and competencies. 
  • A development session, where the manager and the employee discuss the employee's career aspirations and goals and the opportunities and actions to achieve them. 
  • A recognition session, where the manager expresses appreciation and gratitude to the employee for their contributions and achievements. 

The 1-1 meeting should be conducted in a supportive and respectful manner, with a focus on the employee's growth and development rather than their evaluation or judgment. The 1-1 meeting should also be a two-way conversation where the employee can set the agenda, ask questions, share opinions and ideas, and raise any concerns or issues. The 1-1 meeting should be documented and followed up, and the manager should ensure that the employee receives the necessary support and resources to execute the strategy.  This is another great opportunity to capture meeting recordings, transcription, and AI assistance for summaries and action items, using tools such as Microsoft Copilot. 

In conclusion, strategy execution is a complex and challenging process that requires the alignment and commitment of the entire organization. By following these 3 tips for execution with AI assistance for senior management reviews, team cadences, and 1-1 meetings, you can create a culture of excellence and accountability that will enable your organization to achieve or surpass your strategic goals.