Running a strategy planning process and conducting strategy meetings can be challenging when the top executive lacks full knowledge on the subject.

This is a common situation for senior executives who assume responsibilities in unfamiliar areas or business units. It can happen when an internal candidate is given expanded responsibilities across the organization, when an external hire is new to the industry, or when a political appointee possesses more political connections than expertise. Yes, it can also result from an executive not being strong in the job; that happens.

However, it is important to find strategies to navigate this situation and ensure successful outcomes.

If you’re headed into strategy planning as a senior executive who is still acclimating and learning, what do you do? It’s smart to integrate a direct report who has deep expertise into the process to shape strategy planning.

Here’s a game plan to set the stage for success both before and during strategy meetings in these situations.

7 Steps for Prep and Performance


These important interactions and expectation setting activities are intended to create mutual understanding before the strategy process and its meetings begin.

1. Establish the Responsibility Level

Clearly outline how far your direct report can take the strategy process relative to its design, flow, invitations, and meetings. Establish review points, planned coordination, veto power, and decision-making roles. These boundaries will energize your direct report’s contributions and create clarity.

2. Do Your Homework

You’ll need a healthy degree of vulnerability with this entire approach, especially on this step. Honestly assess your critical weaknesses, even asking trusted colleagues what they think. Then, do the upfront homework to prepare. The point isn’t immersing yourself in everything. You do, though, need to develop a basic understanding and context for opportunities and issues that the strategy will address.

3. Make the Rounds

Talk to meeting participants upfront to understand their perspectives. Ask about their:

  • Organizational aspirations
  • Concerns
  • Major questions
  • Preferred participation roles
  • Hoped-for accomplishments during and after the meeting

Incorporate learnings from these discussions into your preparation.

4. Agree on Meeting Roles

Align with your direct report on your respective meeting roles. A senior leader can better make certain things happen, no matter the level of familiarity or experience. These include:

These actions help everyone understand that there’s deliberate responsibility sharing happening to achieve the best results.

5. Outline Strategic Questions to Ask

Strong questions are powerful for confidently and smartly guiding a meeting while also sharing the speaking time with others. From experience and the pre-meeting homework, list questions to stimulate strategic discussions. Our favorites include:

6. Hold a Final Check-in

Coordinate with your direct report before the meeting to review final details and discuss what needs to happen to create the most successful meeting. Discuss major concerns (and how to address them), how you’ll both pave the way for success, and approaches to support each other. This conversation prepares you both for the best personal and organizational meeting performance.

7. Carry Out Your Role


Within the meeting, it’s vital to stay attentive, leverage your strengths, and take the lead in determining commitments and celebrating achievements. Here are keys to follow through on during the meeting:

  • Stay active at the meeting’s meta level: monitor interactions and meeting dynamics, making sure that people uninvolved in the meeting engage in discussions.
  • Identify where you hold unique perspectives and add those at the appropriate times during the meeting.
  • Listen and observe intently in areas where you have less depth and expertise. These are opportunities to jumpstart your learning. There’s no need to say that you don’t know something (display less vulnerability than THAT). Ask questions instead!
  • If there’s a need to change something, get with your direct report at a break and address what you are seeing and thinking. If it’s urgent, call an extra break during the meeting.
  • As meeting segments and the overall meeting conclude, take the lead on determining personal commitments, team member accountability, and timing since you are best positioned for this.
  • Push for celebrating accomplishments at the meeting and as you implement. You are ideal to champion this.

Direct Reports Can Also Carry Out this Approach


Although this list is written with senior executives in mind, a direct report to a boss who will struggle with strategy planning can implement it, too. The key? Being subtle and effectively managing upward. This will help lead a senior exec who doesn’t see the potential pitfalls toward a stronger, more collaborative approach for successfully developing strategy. – Mike Brown