Hichem in Leadership

My First 90 Days: A Playbook for a New Head of IT

Stepping into a new IT leadership role is a unique challenge. You are simultaneously expected to be a stabilizing force, a technical expert, and a strategic visionary. The first three months are the foundation upon which your entire tenure is built.

Throughout my career at companies like Jellysmack, Getaround, and Alan, I’ve refined a 90-day playbook. This isn’t a theoretical guide; it’s the operational process I use to systematically understand an organization, build deep trust with my team and stakeholders, and deliver tangible results. This is my manifesto for how I work.

Phase 1 (Days 1-30): Listen, Learn, and Map Reality

The most significant error a new leader can make is acting with incomplete information. My first month is not for deploying change; it is for disciplined information gathering. My singular goal is to understand the reality on the ground.

My First Priority: People and Processes

Before I audit a single system, I focus on the people. I schedule one-on-ones with my direct reports, my peers in the executive team, key stakeholders across the business, and even vocal end-users.

I’m not there to make promises; I’m there to listen. I seek to understand their workflows, their biggest frustrations, and what they believe IT does well (and where it falls short). This is where the real story lives, far from any documentation.

Building Trust and Our Operating Rhythm

Trust isn’t built in meetings about strategy; it’s forged in daily execution and human connection. From day one, I establish the core rituals for my team, centered on transparency, support, and growth.

  • Daily Stand-ups: This is our ritual for sharing progress, aligning on the day’s tasks, and, most importantly, identifying roadblocks. It’s a forum for us to support each other, not for me to micromanage.
  • Human-Centered 1-on-1s: My 1-on-1s are reserved for the individual. This is their time, not mine. We don’t just talk about project status, unless they want to. This is where I act as a coach. We discuss their professional growth, their career aspirations, and how I can better support them in their role. It’s the single most important tool for building an empowered team.
  • Asynchronous by Default: I foster a culture where writing is paramount. Key decisions, project updates, and process documentation are written down and shared. This forces clarity of thought, creates a persistent knowledge base, and respects everyone’s time and focus. It’s how we scale knowledge and reduce dependency on meetings.

The Quiet Audit

In parallel, I conduct a comprehensive, non-disruptive audit of the existing technology landscape. I create a factual map of the current state, looking at:

  • Infrastructure: What’s on-prem vs. cloud? What are the key dependencies?
  • Security Posture: How is access managed? Is MFA enforced universally? What password manager is in use?
  • Core Services & Licensing: A full review of Google Workspace, key SaaS tools, and associated costs.
  • Asset Management: How are laptops and other hardware deployed, tracked and managed?

My goal is to identify risks, redundancies, and costs without disrupting the team’s ongoing work. I also actively hunt for “shadow IT” - the undocumented tools and workflows people use when official systems fail them. I don’t see them as problems, but more like signals of unmet needs, and ultimately as opportunities for high-impact improvements.

Phase 2 (Days 31-60): From Diagnosis to Strategy

Armed with a month of data and conversations, I shift from listening to synthesizing. The goal is to translate my findings into a clear, prioritized strategy that aligns with the company’s business objectives.

Identify a “Quick Win”

The most critical action in this phase is to identify one high-visibility, low-complexity project that solves a common and frustrating pain point. At a previous company, this was implementing a proper enterprise password manager. It immediately reduced a security risk, simplified daily life for every employee, and demonstrated that the IT department was a partner in making work easier. This single project builds immense trust and political capital.

Separate the Urgent from the Important

Not all problems are created equal. I categorize every issue from my audit using a simple matrix based on impact and urgency. Is it a critical security or operational risk (e.g., a compliance gap for TISAX or ISO 27001)? Or is it a “nice-to-have” efficiency gain?

This framework allows me to focus our finite resources on what truly matters first.

Draft the 6-Month Roadmap

With clear priorities, I draft a high-level, six-month roadmap. This is not a deeply technical document; it is a strategic outline I present to the company leadership. It follows a simple structure:

  1. Here is what I’ve learned about our technology, processes, and people.
  2. Here are our biggest risks and opportunities.
  3. Here is the quick win I will execute now to deliver immediate value.
  4. Here is the strategic sequence of what we will tackle next.

Phase 3 (Days 61-90): Execute, Communicate and Empower

The final phase of my 90-day plan is about shifting from planning to execution. This is where I demonstrate that my team and I deliver on our commitments and begin building a high-performing IT function for the long term.

Launch the Quick Win

I oversee the execution of the high-visibility project identified in Phase 2. Flawless execution is critical, and that hinges on clear, multi-channel communication. When integrating the Drivy and Getaround IT systems, we used every channel at our disposal—Slack, email, wikis, and All-Hands meetings—to ensure everyone knew what was happening, when, and why. This over-communication demystifies IT and builds confidence.

Solidify Communication Rhythms

I establish predictable, ongoing communication channels to make our work transparent. This can be a monthly IT newsletter, a dedicated support channel in Slack with clear SLAs, or a simple public dashboard showing system status and project progress. Consistency is key.

Empower Through Ownership

I begin to formally delegate ownership of systems and processes to my team members. The foundation for this was laid in our 1-on-1s. By understanding their skills and aspirations, I can align their responsibilities with their growth path. I ensure they have the tools and training they need, whether it’s advanced knowledge of a tool like GAM for Google Workspace administration or new asset management software. An empowered team is a scalable team.

A Foundation for the Future

This 90-day process is not about solving every problem. It is my method for building a foundation of trust, understanding, and strategic alignment. By moving methodically from listening to planning to executing, I establish IT as a strategic business partner, not just a technical cost center. I prove that IT can be a powerful enabler for the entire company.

This is my playbook. I’m sharing it because I believe in transparency and process.

What’s yours? I’m genuinely curious to hear other perspectives and learn from your experiences.

Don’t hesitate to connect with me and share your own playbook.