Dear Yogesh,

I serve as a regional president for a global services company. Recently, a key executive on my team retired suddenly due to health concerns. We interviewed several candidates for the role but ultimately took the advice of the outgoing executive and promoted his second-in-command.

She interviewed well, presented a compelling vision, and repeatedly described herself as “strategic.” While she has many strengths, six months into the role, I’m not seeing the strategic capability I need.

I’ll admit I’ve been spoiled by a seasoned, highly capable executive team. Providing detailed guidance at this level feels frustrating, and I struggle to articulate exactly what’s missing. I keep thinking, I’ll know it when I see it.

Part of me is ready to call this a failed hire, but I’m also reluctant to start over with someone new who would need time to get up to speed. She’s out on vacation for the next two weeks, and I want to use this time to create a plan for her return. Any advice?

Raghav

Dear Raghav,

First, let’s acknowledge the complexity of your situation. Transitioning into an executive role—especially on a well-established team—can be daunting. You’re likely right that she’s struggling to adapt from being second-in-command to being the one fully accountable for strategic decisions.

At the same time, “I’ll know it when I see it” isn’t a clear or constructive way to lead. If you want to give her a fair chance to succeed, you need to set clear expectations and support her development. Here’s a roadmap to help you move forward:

1. Integrate Her into the Team

Joining an established executive team can be intimidating, especially when everyone else shares a long history. Work with your HR partner to create a team charter that clearly defines:

• The mission of the executive team.

• The roles and responsibilities of each team member.

• Communication and behavioral norms.

This process will allow your team to align on expectations and create a welcoming, structured environment for your new executive. What may have felt organic with your former team will now need to be made explicit.

While creating a team charter might feel tedious, it will provide the clarity and cohesion you need to rebuild your team dynamic.

2. Clarify What Success Looks Like

You mentioned that you’re unsure how to articulate what’s missing. To get there, consider these questions:

• What specifically made her predecessor successful?

• What did he avoid doing that worked well?

• What are the critical gaps between your expectations and her performance?

• What specific behaviors or actions do you want her to start, stop, or continue?

Also, reflect on the foundational competencies you expect from a strategic executive. Here are some common strategic management behaviors to consider:

• Articulating and sharing a vision and objectives.

• Setting and achieving clear goals.

• Analyzing internal strengths and external threats.

• Allocating resources and designing organizational structures.

• Leading change initiatives.

• Assessing and responding to results effectively.

Use these prompts to create a detailed list of the outcomes and behaviors you expect. Once you’ve clarified what success looks like, share it with her in a constructive, transparent conversation.

3. Build Her Confidence

Stepping into a senior role often requires building a new level of confidence, especially when the stakes are higher, and mistakes carry significant consequences. As her leader, you can help her build that confidence by:

• Offering regular, constructive feedback.

• Celebrating small wins and progress.

• Encouraging her to trust her instincts and take ownership of decisions.

This doesn’t mean lowering your standards—it means creating a supportive environment where she can rise to the challenge.

4. Give It a Timetable

While you’re working to support her, set a clear timeline for assessing progress. Define milestones and indicators of improvement. If, after this period, it’s clear she can’t meet the role’s demands, you’ll have a well-documented case for exploring other options.

A Final Word

If you were to hire someone new, they would face similar challenges—learning the role, integrating into the team, and adapting to your expectations. The difference is that your current hire already understands your organization. Investing in her success now might save you time and effort in the long run.

Approach this as a leadership opportunity for both of you. With clarity, guidance, and support, she may surprise you.

Best regards,

Yogesh

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