Senior Planner: Questions to Ask in Week 1 (Checklist)

What to Ask in Week 1 as a Senior Planner

Starting a new Senior Planner role? Don’t waste time on generic onboarding. This is about setting yourself up for impact immediately. You’ll walk away with a checklist of questions to ask, a scorecard to assess the answers, and a script for framing your inquiries, so you can hit the ground running and avoid common pitfalls.

What You’ll Walk Away With

• A 15-item checklist of targeted questions to ask in your first week, categorized by stakeholder.
• A scorecard to evaluate the quality of the answers you receive, helping you identify potential risks early.
• A script for initiating conversations with key stakeholders, ensuring you get the information you need without sounding demanding.
• A framework for prioritizing your learning based on impact and urgency.
• A list of quiet red flags to watch out for, indicating potential problems with project scope, budget, or stakeholder alignment.
• A 7-day action plan to implement your findings and establish yourself as a proactive Senior Planner.

Scope: What This Is and Isn’t

• This is: A practical guide to gathering essential information in your first week as a Senior Planner.
• This is: Focused on questions that reveal project health, stakeholder alignment, and potential risks.
• This isn’t: A generic onboarding checklist.
• This isn’t: About learning company policies or HR procedures.

The Senior Planner’s Mission: Controlling Chaos

A Senior Planner exists to drive projects to successful completion for the client while controlling scope, schedule, and budget. Your first week is about understanding the landscape you’re stepping into.

Why Your First Week Matters: Avoiding the Landmines

Your first week is critical for setting expectations and identifying potential problems before they explode. It’s about understanding the project’s history, the stakeholder dynamics, and the constraints you’ll be operating under. Don’t assume everything is as it seems.

Checklist: Questions to Ask in Your First Week

Prioritize questions that uncover potential risks and opportunities early. Ask these questions within the first week to identify potential issues and demonstrate your proactive approach. Here’s a categorized checklist:

With the Project Sponsor/Executive Stakeholder:

1. What are the top 3 priorities for this project? Purpose: Ensures alignment with executive vision. Output: Prioritized list of objectives.
2. What keeps you up at night regarding this project? Purpose: Uncovers hidden risks and concerns. Output: List of potential threats.
3. What does success look like, and how will it be measured? Purpose: Defines clear success criteria and KPIs. Output: List of measurable outcomes.

With the Project Manager/Delivery Lead:

1. Can I see the current project plan and risk register? Purpose: Assesses project health and potential roadblocks. Output: Access to project documentation.
2. What are the biggest challenges the team is currently facing? Purpose: Identifies immediate obstacles and resource needs. Output: List of current issues.
3. What’s the process for change control and scope management? Purpose: Understands how changes are handled and approved. Output: Knowledge of change management procedures.
4. What’s the reporting cadence and who are the key stakeholders receiving updates? Purpose: Understand the current communications approach. Output: Insight into the status reporting process.

With the Finance/Procurement Team:

1. What’s the approved budget for this project, and what’s the current burn rate? Purpose: Assesses financial health and potential overruns. Output: Budget overview and spending report.
2. What are the payment terms with our key vendors? Purpose: Understands vendor contracts and financial obligations. Output: Summary of vendor payment agreements.
3. What’s the process for budget adjustments and change orders? Purpose: Understands how budget changes are handled. Output: Knowledge of budget adjustment procedures.

With the Key Vendors/External Partners:

1. What are the key milestones and deliverables outlined in our contract? Purpose: Ensures clarity on contractual obligations. Output: Summary of key contract terms.
2. What are the key dependencies and potential risks to meeting those milestones? Purpose: Identifies potential delays and challenges. Output: List of vendor-related risks.
3. What’s your process for escalating issues and communicating delays? Purpose: Understands vendor communication protocols. Output: Knowledge of vendor escalation procedures.

With the Legal/Compliance Team:

1. Are there any specific compliance requirements or legal considerations for this project? Purpose: Identifies potential legal and regulatory hurdles. Output: List of compliance requirements.
2. What’s the process for legal review of contracts and deliverables? Purpose: Understands legal review procedures and timelines. Output: Knowledge of legal review processes.

Scorecard: Evaluating the Answers

Don’t just ask the questions; evaluate the quality of the answers. Use this scorecard to assess the responses you receive and identify potential red flags:

The Mistake That Quietly Kills Candidates

The mistake that quietly kills candidates is accepting vague answers without probing for specifics. A weak Senior Planner nods along; a strong one digs deeper.

Use this when you need to push back on a vague answer:

“I appreciate the high-level overview. To ensure we’re aligned, could you provide a specific example of [challenge/risk/success metric]?”

Quiet Red Flags to Watch For

Pay attention to these subtle warning signs during your first week. These red flags can indicate underlying issues that may require immediate attention:

• Vague answers to budget questions: Indicates potential financial mismanagement or lack of transparency.
• Lack of a documented risk register: Suggests poor risk management practices.
• Conflicting priorities among stakeholders: Signals potential misalignment and future conflicts.
• Resistance to providing access to project documentation: Raises concerns about transparency and potential cover-ups.
• Unclear change control process: Indicates potential for scope creep and budget overruns.
• Vendors hesitant to discuss potential risks: Suggests potential vendor issues or lack of communication.

A 7-Day Action Plan: Implementing Your Findings

Turn your findings into action with this 7-day plan. This plan ensures you translate your initial insights into concrete steps to improve project outcomes.

• Day 1-2: Conduct initial stakeholder interviews and gather project documentation.
• Day 3-4: Review documentation, score responses, and identify key risks and opportunities.
• Day 5: Develop a preliminary risk mitigation plan and share it with the project team.
• Day 6: Present your findings and recommendations to the project sponsor/executive stakeholder.
• Day 7: Finalize your action plan and begin implementing it with the team.

What a Hiring Manager Scans for in 15 Seconds

Hiring managers quickly assess if you understand the stakes. They’re looking for signs that you’re proactive, risk-aware, and focused on outcomes.

• Clear understanding of project goals: Shows you’re aligned with the strategic vision.
• Ability to identify potential risks: Demonstrates your proactive risk management skills.
• Focus on measurable outcomes: Highlights your commitment to delivering results.
• Probing questions about budget and resources: Signals your financial acumen and resource management skills.
• Emphasis on stakeholder alignment: Indicates your ability to build consensus and manage expectations.

FAQ

What if stakeholders are resistant to answering my questions?

Frame your questions as a collaborative effort to improve project outcomes. Emphasize that you’re trying to understand the project better so you can contribute effectively. If resistance persists, escalate to your manager or project sponsor.

How do I prioritize which stakeholders to interview first?

Start with the project sponsor or executive stakeholder to understand the overall vision and priorities. Then, interview the project manager or delivery lead to assess the current project status and challenges. Finally, interview the finance/procurement team to understand the budget and financial constraints.

What if I uncover major red flags during my first week?

Document your findings and present them to your manager or project sponsor as soon as possible. Propose a plan to mitigate the risks and address the issues. Be prepared to escalate if necessary.

How do I handle conflicting information from different stakeholders?

Acknowledge the conflicting information and try to reconcile it by gathering additional data or facilitating a discussion between the stakeholders. If the conflict cannot be resolved, escalate to your manager or project sponsor for guidance.

What if I don’t have experience in a particular area, such as finance or legal?

Be honest about your limitations and seek guidance from experts in those areas. Focus on understanding the key concepts and processes relevant to the project. Take courses or seek mentorship opportunities to improve your knowledge and skills.

How can I build trust and rapport with stakeholders during my first week?

Be respectful, professional, and attentive during your interactions with stakeholders. Listen actively to their concerns and perspectives. Show genuine interest in understanding their roles and responsibilities. Follow up on your commitments and keep them informed of your progress.

Should I document all my findings and action plans?

Yes, documenting your findings and action plans is essential for tracking progress and ensuring accountability. Use a project management tool or a simple spreadsheet to record your questions, answers, risks, and mitigation plans. Share your documentation with the project team and key stakeholders.

How do I avoid sounding demanding or critical when asking questions?

Frame your questions as a collaborative effort to improve project outcomes. Use a neutral and objective tone. Avoid accusatory language or personal attacks. Focus on facts and data, not opinions or assumptions.

What if the project is already in crisis mode when I start?

Focus on stabilizing the situation and identifying the root causes of the crisis. Gather data, assess the damage, and develop a recovery plan. Communicate clearly and frequently with stakeholders. Be prepared to make tough decisions and take decisive action.

How do I balance my learning with my other responsibilities during my first week?

Prioritize your learning based on impact and urgency. Focus on understanding the key project goals, risks, and constraints. Delegate or postpone less critical tasks to make time for learning. Use your commute or lunch breaks to read project documentation or listen to relevant podcasts.

How do I use this checklist if I’m starting mid-project rather than at the beginning?

Adapt the questions to the current project phase and focus on understanding the project’s history, challenges, and remaining deliverables. Ask about past decisions, lessons learned, and potential risks to the remaining timeline and budget.

What if the answers I receive are overly optimistic or unrealistic?

Challenge overly optimistic answers with probing questions and data. Ask for evidence to support the claims and assess the feasibility of the plans. Be skeptical but respectful. Escalate your concerns if you believe the project is based on unrealistic assumptions.

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