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The First 30 Days
The first month is a critical time to assess your product, your role, and your team.
The first thirty days
Congratulations
You have just landed your dream job as a Director of Product Management. Over the past ten years, you have been a Product Manager and, three years ago, you were appointed Head of Product, managing a team of Product Managers and Product Designers.
Today is your first day as Director in the scale-up that has just hired you. Your schedule is already packed: you have a one-on-one with your new boss, a meeting with your main counterpart, the Director of Engineering, and meetings with two of your direct reports. The IT department has provided you with a brand new MacBook Pro.
You recall a time when it was difficult to get an Apple computer, as they were reserved for creative executives privileged to work with the Adobe Creative Suite. Nowadays, everything is simpler and faster. Within a couple of hours, your new email address is set up, and you are already exploring the tools you will be using: Linear, Slack, Zoom. It's not much different from what you had at your previous company.
Your new boss, the Chief Product Officer, invites you for lunch to discuss some of the challenges you will face and to ensure you are invited to all the critical meetings of the week.
It's very likely that your first day will resemble this one, but the following days will be vastly different. As a new employee, you'll spend the first two weeks learning about your company, your industry, and the products you will manage. I use the term "products" because as a director, you will either manage a single product with multiple touchpoints targeting different audiences, or you will oversee completely different products, each with their own customer base.
The company does not expect you to make sudden changes. They will wait and allow the new director time to understand the company and its unique challenges, to build a network of people, to establish relationships with team members, and to fully grasp your responsibilities. You come with fresh eyes. Use this precious time to assess the situation.
The period of assessment
During this time, you will need to assess several dimensions of your new environment.
Assess your product, and if you have many, the portfolio of products. Before getting the job, you used the product, tested it, asked questions, and read documents shared by the team. This gave you a superficial view. Now, as an insider, you have access to all the dashboards, the customer reviews, and you can interview people involved in different aspects of the product. Spend time with customer care agents, ask questions, and listen.
Assess your role. While you did your due diligence during the interview process, your perception of the role might differ significantly from its reality. There's often a gap between one's dream of a job and its actual demands. To use a quantum physics analogy: before you have the role, there's a full range of possibilities. Once you assume the position, you, as the observer, collapse the wave function, revealing the true nature of the role.
Assess the team and its members. Evaluate the strengths, weaknesses, and dynamics of your team. Take the time to talk to all your direct reports and all the skip-levels. I recommend refraining from jumping into solutions prematurely, especially if some individuals express complaints and desire immediate decisions from you. It's more crucial that you listen to everyone first and avoid making promises you are not sure you can fulfill. You need to understand each member's role, expertise, and contribution. You also need to understand them at a personal level: what are their dreams? What do they really like doing?
Assess the business. Understand how the business truly performs. If the company is publicly listed, you should already know a lot about its performance thanks to the quarterly earnings report and the annual reports found on the Investor Relations portal. However, if the company is a startup and still private, there is no clear picture of the financial situation. To gain a more accurate assessment, talk to the Sales Director and someone from the Finance team. These conversations will help you identify gaps in the product and give you a sense of business performance.
Assess the dynamics within the executive team and the senior leadership team. As a Product Director, you are likely not part of the executive team that consists of all the CxOs. However, you are probably part of an extended senior leadership team, sometimes referred to as the SLT. Within the next two weeks, you will have a meeting with them. Pay close attention to the main topics of discussion and the key concerns of the executive team. Observing the dynamics between team members is important. Whether you like it or not, there is always politics when dealing with human beings, and you need to be aware of power struggles between leaders.
Assess the relationship between the product team and the stakeholders. In some companies, the product team is embedded inside the engineering team, with a single CxO managing Product and Engineering. In others, the product team is independent and very close to the CEO. In others still, the product team is closer to the Marketing department. There are no rules, only specific cases. You need to understand which external department is closer to you and the rationale behind this. You may have been hired to create new connections and increase collaboration between departments. Pay close attention and don't hesitate to ask questions. If you are coming from outside the organization, people will give you an honest view of reality. You will also understand which team is most unhappy with the product team and why.
Assess the real reason you were hired. Officially, you were hired as the Director of Product, either to fill a new role or to replace someone. If it's the latter, it's crucial to understand why your predecessor left. Were they let go, or did they resign? Although there might be some drama involved, understanding the circumstances of their departure can provide insights that will help you perform better. Ultimately, you were hired to solve a problem. You might already know what this main problem is, but if not, now is the time to uncover it.
Assessing the product
If the product had no problems, there would be no need for a product team to manage it. You have been hired to address one or several issues with the product.
The range of problems you might encounter includes:
Problem of slow growth. Perhaps the product was successful in the past but is no longer growing. Your task is to reignite growth and execute a turnaround. More challenging is a situation where the product never experienced significant growth, indicating a product-market fit problem. Ideally, the team is aware of this and seeks your expertise to achieve PMF. The worst-case scenario is poor product-market fit combined with a failure to recognize the situation. Data don't lie, but sometimes people don't want to see it. This situation, which I have encountered in my career, is particularly challenging. We will see in a future chapter how to address it. Typically, you will need to work closely with the sales and marketing team.
Problem of poor delivery. In this case, the product has production issues and many bugs, and it's very slow to change anything. This often stems from a combination of engineering and product management challenges. While daunting, this problem typically arises from rapid growth, overwhelming customer demands, and insufficiently experienced product and engineering leadership teams that were not able to focus on the main areas. Instead, they accepted every request and created a bloated platform that is now impossible to move. There is huge technical debt. You will need to work closely with the engineering team and executive team to address this issue.
Scaling issues. In this case, the product is so successful that you have production problems, the service shuts down, and you lose revenue if you are in a D2C business, or you have unsatisfied enterprise customers who threaten to switch to another more stable partner. This is a good problem to have. Addressing it will require good project management skills and the ability to create a laser-focused taskforce.
Problem of low monetization. The product might be popular among users but suffer from poor unit economics, where increased usage leads to greater losses. Your role involves monetizing the user base promptly. You will need to work closely with the business analytics and data intelligence team.
Problem of misalignment between stakeholders. You may face conflicting demands on the product, such as the finance team requiring compliance upgrades and the sales team needing new features to close critical deals. With your boss not taking sides, you find yourself mediating a complex internal struggle. This will require excellent diplomatic skills.
It's also possible that there are no issues like those mentioned above, and instead you have been hired to tackle an opportunity. In that case, the broad areas are product expansion or new product development:
Product expansion opportunity. You will need to create the right new functionalities that address an adjacent pain point of your customers. This is usually about capturing more value from your existing customers.
Growth expansion opportunity. You are hired to expand the product to a new market. For instance, this might mean adapting your product initially targeted towards the US market to grow in Southeast Asia. You will need to localize, but also add new integrations with the players dominant in the region. It might involve different payment mechanisms and supporting specific regional regulations. A new market can also mean the same geography but moving from B2C to B2B, or targeting a different customer profile. This is exciting work, and it will require you to address potential skill gaps in your team.
New product development. You are hired to create a new product from scratch. You need to set up a new team with new employees, external resources, and talent you will need to hire. This is exciting but comes with its own set of challenges.
Assessing the role
If you have been promoted to the Director of Product role, you need to understand that what took you to this point will not work in this new position. You have to take a different approach.
Less depth, more breadth. On the product management side, you have to transition from depth to breadth. As you moved from associate product manager to product manager to senior product manager, you tackled consistently larger and more difficult product problems. If you were particularly good at solving one type of problem, you were likely given harder problems in that particular area. This is logical, as the company wanted to increase the value they were getting from you. Now that you are the Director, you need to change your approach. You need to give up some of the depth and go wide across multiple types of product work. You have to grow the arms of your T-shaped skillset.
Training and guiding others. You won't be judged on a particular product skill you have. Instead, you will be evaluated on your ability to understand what your team needs to do and on your training skills to get them where they need to be. In High Output Management, Andy Grove describes training as one of the highest leverage activities a manager can do. As you take this new role, think about what you will be able to train your team on yourself, and where you will need external help.
Managing and coaching managers. It might be the first time you are managing managers. Managers don't need the same kind of attention as individual contributors. They don't need as much guidance on their work, but they need your help managing their team. They probably have their own management challenges and want you to help them become better leaders. You have a great opportunity to create connection with them by being on their side. During the first 30 days, spend time listening to your direct reports and let them present their team and the challenges they have with some of their members.
Managing up. During your first 30 days, you need to understand how your boss functions. What are they expecting from you? What are their priorities and how do they like to be kept informed on your progress? As a Director, you will often have very little guidance from your boss. They are extremely busy and hired you to manage many problems for them. Even though communication will be infrequent from them, your communication will have to be more extensive upward. It's your job to understand their style and preferences.
Decision, decision, decision. If you have all the data available to make a decision and everybody already agrees, it is not a decision. A real decision takes courage because there is uncertainty on both the input and the output. The company requires you to make decisions on a consistent basis, and in the long run, you will be judged on the quality of those decisions. If you didn't make any decisions, it usually means you made the decision to stay with the status quo. Remember that you have been hired to enact change, so this is usually not an option. Making decisions is one of the most demanding parts of your new job and a big difference from your previous role. In the first 30 days, assess the kind of decisions the organization expects from you and the cadence as well.
Planning. As a product manager, you were already asked to do a fair amount of planning. As a director, this goes to the next level: you will be asked to do budgeting, resource planning, and product portfolio roadmapping. During your first 30 days, understand the scope of your responsibilities in this area. It is useful to ask your peers about previous presentations, the past year's budget for the product team, and what falls under your purview.
Influencing. As Director of Product, you have some level of control over your team, and even though you are not the leader of other organizations, you have influence over them, particularly the engineering team. It is critical that during the first months, people in those organizations get to know you and start trusting you. This can set the tone for the rest of your tenure.
Assessing the team
I was once asked: if you were to go to an island for a year, which team members would you pick to come with you? It was in a context of rightsizing the business, and every director was being asked to assess which team members they needed to keep and which ones we would have to let go.
This was not a happy moment, and my answer was "it depends."
There is never a right team in absolute terms. It is always relative to a context, a product, and the phase you are in. If you are an explorer like Shackleton going to Antarctica, you need to pick mavericks and trailblazers. If you are a DJ hired to perform at a luxury resort in Ibiza as the resident, you will pick a sound engineer, your assistant, a cook, and a few artists. If you are a scientist going to Jurassic Park... well, you get the idea. There is no best team for any job; there is one best team for a particular job.
Making decisions about your team does not only happen when you are rightsizing the organization. It will also come when the company is growing. As a product grows, you need to change your team, refine its organization, add new skills, and you might not need as many generalists as at the beginning.
During your first 30 days, assess your team and identify problems:
Assessing the business
In the introduction, I mentioned that it is easier to assess the business if you have been hired by a publicly listed company because there is quarterly reporting on performance. But even if the company is listed, the exact performance of your business area might not be clear.
It is critical that you talk to the Sales Director in charge of selling your product and to the Finance Director in charge of reporting on your P&L. They will provide you with a level of detail you will not find easily without them.
Business drives everything, and it certainly drives product priorities.
Assessing AI readiness
In 2026 and beyond, no assessment of a product organization is complete without understanding its relationship with AI. What matters here is how the team uses AI to build, analyze, and iterate on the product, regardless of whether AI features appear in the product itself.
Assess your team's AI fluency. How comfortable is your team with AI tools? Are your product managers using AI assistants to draft PRDs, analyze user feedback, or explore solution spaces? Are your designers using AI for rapid prototyping? Are your engineers using AI coding assistants? The gap between AI-fluent teams and traditional teams is widening rapidly. A team that has embraced these tools can move two to three times faster than one that hasn't. During your first conversations with team members, pay attention to how they talk about AI. Do they see it as a threat, a distraction, or an essential part of their workflow?
Assess the current AI tooling. What AI tools has the company adopted, and how deeply are they integrated into daily work? Some organizations have official tools with proper security reviews and enterprise agreements. Others have a patchwork of individual subscriptions and shadow IT. Some have banned AI tools entirely out of security concerns, which creates its own problems as employees find workarounds. You need to understand the current state: what's approved, what's actually being used, and what gaps exist between the two.
Assess AI in the product itself. Does your product use AI or machine learning? If so, how mature is that implementation? Many products have legacy ML models that were state-of-the-art three years ago but are now outdated. Others have recently added AI features that were rushed to market without proper evaluation. Some products have no AI at all and may be falling behind competitors. You need to understand not just what AI capabilities exist, but how they were built, how they're maintained, and whether they actually deliver value to users.
Assess the AI technical debt. AI systems accumulate technical debt faster than traditional software. Models drift as user behavior changes. Training data becomes stale. Evaluation frameworks that made sense a year ago no longer capture what matters. If your product has AI components, ask the engineering team about model freshness, monitoring, and the last time anyone evaluated whether the AI features are actually working as intended. The answers, or the inability to answer, will tell you a lot.
Assess competitor AI capabilities. Your competitors are also navigating this transition. Some are further ahead; others are behind. During your first 30 days, spend time with the competitive intelligence your team has gathered and supplement it with your own research. How are competitors using AI in their products? How are they talking about AI in their marketing? Are they shipping AI features faster than your team? Understanding the competitive landscape will help you calibrate the urgency of your own AI initiatives.
Assess organizational readiness for AI-driven change. Beyond tools and technology, gauge the organization's appetite for AI transformation. Is leadership excited about AI possibilities or anxious about risks? Is there budget allocated for AI initiatives, or is it an unfunded mandate? Are there legal or compliance concerns that constrain what you can do? Some organizations are ready to move fast; others need more groundwork before AI initiatives can succeed. Your job is to understand where your organization sits on this spectrum and what it will take to move forward.
The answers to these questions will shape your first major decisions as Director. If your team is AI-fluent and well-tooled, you can focus on strategic application. If there are significant gaps, closing them may need to become an early priority. Either way, you cannot lead a product team in 2026 without a clear picture of where you stand with AI.