Your first 90 days in your new product leadership role

Congrats! You have just been promoted, or you were hired into a new product leadership role. That’s super exciting, and also the best time to make an intentional plan for how to succeed in it. The first three months count in setting you up for success (or learning fast, that this particular role is not what you want).

Here is how I would approach it:

• Get clear on what you want to have achieved by when in the first 90 days
• Schedule a regular reflection time in your calendar to review whether you are on track with your progress. You’ll find reflection templates to download below.
  Bookmark this post, so you can come back to it in the coming weeks.
• Proactively seek the information you need and build the relationships that matter.

You have two core jobs as a product leader:
1) Defining, Aligning and Continuously updating what success means in your context
2) Facilitating Team Success: Enabling your team to deliver on that success aspiration

Your first 90 days in your new product leadership role are all about setting yourself up to succeed with those two jobs. Your success depends on having access to the right kind of information (about company strategy, about company financials, about customer insights, about how your team works and what it needs) and even more so about relationships and the systems you are a part of.

You will not be able to create your team’s success alone. It takes the diverse perspectives of your cross-functional teams as well as the successful collaboration between teams, with your stakeholders and with your clients to make this work. All of this relies on trust and relationships. Trust you may need to earn and keep and relationships you will need to build.

Ideally you would work with an amazing leader who sets up an onboarding experience that makes sense, but I would not rely on that. Especially not if you are hired to be the most senior product leader in your organization. Chances are nobody will take time to create your onboarding experience. The expectation is that you can navigate this on your own (while setting it up for your team).

Here is how I would approach it:

Week 1: Onboarding and Listening

Primary Goal: The first week is all about arriving, absorbing context, meeting people, setting up, starting to build relationships and learning. This is about planting the seeds of trust you’ll eventually need to deliver great outcomes with your team.

• Team: Get to know the humans in your team. Set up 1:1s with everyone reporting to you. Take time to listen and ask what support your team member is looking for from you. Ask them about their expectations of you as well as their career goals. Ask open-ended questions like “What is working well?”, “What is blocking us?” “What are you hoping for in our working relationship?”
• Stakeholders: Understand who your important stakeholders are (who has power in your organization and needs to be included or informed for decisions) and set up time to meet them to start building those relationships. Ask their advice for who else you should meet and what they would recommend you need to learn to succeed in your new role. Ask open questions about what is working well, or blocking your teams from collaborating.
• Company & Market: Ask about company strategy, product strategy, your market and positioning vs. your main competitors and the current team goals and roadmaps.
  As you start talking to stakeholders and team members, try to understand if your teams are well aligned on strategic direction and collaboration with other teams. Listen for alignment and improvement opportunities.
• Clients: Find out how to meet clients and set up conversations to build your own product sense in this new context. Especially if you got hired from another organization and you have not had direct contact with your organization’s clients yet.
• Reflections: Schedule a regular reflection time in your calendar. I recommend 90 minutes once a week to review your onboarding progress. Friday afternoons worked well for me.

This is a suggested list of reflection questions after the first week. It is by no means meant as a complete list, but it is a decent starting point:

Reflections Week 1:

What have I learnt this week about my Team, Stakeholders, Company and Market and Clients? Who have I not met yet that I should set up time with?

How clear am I on what success means in our context? What could I do to get more clarity on this?

What can I see as the most impactful way to help my team achieve that success?

What can I do to become a more effective leader? (You could download the action plan list from this post, do a quick self-assessment and identify a learning topic that matters for your current context).

A template for structuring your first week’s reflections can be downloaded at the bottom of this post. Before filling it in, read the week 1 section again.

Week 2-4: Sensemaking & Trust Building

Primary goal: In your first month you want to make progress in deepening your understanding of the current state. Start to enrich the information that was given to you in the first week with your own observations and reflections. You want to identify key gaps and opportunities. You also want to keep building trusting relationships with your team, stakeholders and key clients.

• Team: You’re still listening a lot and you’re building the trust and relationships to be in a position to be accepted and effective as a leader with your team.
  • Keep meeting with your team members in regular 1:1s. The main goals for those are to establish a trusting relationship that will allow for an open exchange of expectations. This builds the foundation for coaching and developing your product team members. If there are any obvious and easy wins you can create for a team member, support them with these!
  • If you are taking the team on from a previous manager and there are existing performance documents and goals: Find out where they are and ideally set up time to talk to the outgoing manager about them. Seek to understand how the current titles, relative compensation and career goals for team members are structured, and how well these are matching actual performance and capabilities.
  • Join the existing regular team meetings. Observe and ask yourself: Is the purpose of each meeting clear? Does it follow a logical agenda? How to people show up in that meeting? Are all perspectives heard? What is the tone in those meetings? Are there signs of psychological safety or is there a lot of blame and fear in the space? How do those regular meetings support strategic direction, effective collaboration and team goals?
  • Take an hour with your team to take the ValueRevels Product Org Fitness test. Discuss your results as a team. You’ll get a lot of good insight where there is aligned understanding, conflicts or misalignment on product org best practices in your team.
• Stakeholders: You’re also still in learning mode with all your important stakeholders, but this is also a space where they will want to understand how you might support them or whether you become a threat to their goals in any form. Your main goal with your stakeholders continues to be relationship building and learning about their interests and incentives.
  • Invest in the relationship with your manager (and if applicable) your skip level manager and your most important stakeholders. Find out how you might support them in succeeding in their roles.
  • Observe the culture around you. Ask and watch what kind of behaviors are wanted and rewarded. There might be a gap between the official leadership principles and values of your organization and the lived culture. You want to understand what actual behavior is being rewarded or punished in your organization.
  • Join the leadership team meetings and other alignment meetings that are currently set up. Try to understand how they operate, whether there is a continuous process around strategy updates and goal setting and who holds power, speaking time and influence in those meetings. Find out how budgeting and staffing decisions are made for the coming year and who influences these.
• Company & Market: You want to continue to learn as much as you can here as well.
  • Start putting together a first draft of a Business Model Canvas and positioning statement based on the insights and conversations you have had with your team, clients and stakeholders. Listen for how well aligned these are (and where you spot misalignments). Get curious about the parts that don’t make sense to you yet. You have the advantage of being new in your role. That usually gives you permission to ask questions from a fresh perspective.
  • Find out how decisions are made. Formally and informally.
  • Identify ideas for quick wins that show value without overstepping or disrupting.
  • Start mapping out your main competitors and what you can find about their relative positioning to you. Find out what your current moat is and how your teams might contribute to building or strengthening it.
• Clients: By the end of your first month you want to have met with at least 5-10, ideally 20 different clients. And set up a routine for regular conversations with key clients. The goal is to build and hone your direct insights from clients on what works and does not work for them with your current product. You will want to understand if your product and strategic moat matters to them or if you have to adapt and change to keep winning their trust and business.

Reflection questions for weeks 2-4:

What have I learnt this week about my Clients, Team, Stakeholders, Company and Market? Who have I not met yet that I should set up time with?

What is my working theory of what success means in our organization? Am I clear on both strategic as well as financial priorities for my organization? In what way has my understanding evolved compared to the previous week? What can I do to get more clarity on this?

What can I now see as the most impactful way to help my team achieve that success?
Is there any structural change needed to enable my team? If so, what do I see and how might I vet this? Whose support would I need for that?

What can I do to become a more effective leader?
What feedback was shared with me that I want to take action on? Who might be a good mentor or coach helping me navigate this in my organization? Is my manager able to help with this? If not, where else might I get the support I need for my own development?

What am I missing?
Do I have an intuition about something here? Who might help me find a blind spot?

A template for structuring your week 2-4 reflections can be downloaded at the bottom of this post. Before filling it out, read the week 2-4 section again.

Week 5-8: Strategic Framing & Direction Setting

Primary Goal: In your second month with the organization you want to go from listening mode to starting to put together your own strategic insights. You will still have to learn a lot, but by organizing your thinking and by leaning on your team and stakeholders to help you see what you’re missing, you’re starting to position yourself as an active leader for your part of the product organization. By week six to eight you want to have a working prototype of an aligned success definition and initial ideas for how to enable your team to go after that success.

• Team: Your goal is to keep building relationships and trust intentionally. Keep listening for the struggles and issues your team members are facing and seek to find patterns and systemic issues that you can address.
  • Set up a time to co-create a model of how each of your teams is creating strategic and financial business impact (e.g. by using a Business Model Canvas Frame, but many other approaches can work. You could use Martin Erikssons Decision Stack, Roger Martin’s Playing to Win structure, or any other Strategic frame to strengthen your team’s strategy muscle). It’s less important to find the perfect tool and more important to get into the practice of doing strategic work every week.
  • Pick up one of the topics from the Value Rebels Product Org Fitness Test (or any other structured evaluation on your product organization) and start addressing it with your team. This shows the team that you take their development serious, and they can expect you to take action for them.
  • Ask each team member about what they have been learning from customers this week. (This serves multiple purposes. It surfaces if your team members are regularly talking to customers, it surfaces customer insights, and it shows you how your team applies discovery insights into their decision-making and priorities.) Start to identify how these insights are shared with the organization (or where they should be shared).
  • In regular team meetings observe if the agenda is covering some sort of link to strategic goals, OKRs or other direction setting mechanisms. Observe if they all align into the organization’s strategic and financial goals. This is what helps you understand if your teams are focused on delivering value to your organization.
  • If needed, address any glaring team issues (e.g. capability gaps, role clarity, misalignment with peers)
  • Find out if there is a documented way to measure and evaluate performance. Review it to see if it makes sense.
• Stakeholders: You want to keep building those key relationships and gain your stakeholder’s trust. Keep listening to their input. You are still “the new person” who can ask for advice and strategic insight from them.
  • Share your own strategic thoughts and learnings from what you have heard in conversations with your team and other stakeholders. Surface if you found any contradictions and (if you don’t know this yet) ask for guidance on how these typically get resolved in your organization.
  • A good way to surface these contradictions is to frame them as tradeoffs and have senior leadership weigh in on their relative priority. This gives you insights into ideas for “product principles” that might help with decision making in the coming months. Keep listening for patterns here. If the same contradiction keeps showing up and gets decided a specific way, you found a candidate for a product or leadership principle. Something that should get formal signoff eventually.
• Company & Market: You want to set up a system that keeps you informed of the most important sources of information.
  • Identify key market players (both clients as well as competitors) and set up an agent that summarizes key postings and discussions from these sources once a week.
  • Identify what internal communication channels have information you should follow and set up a second agent that collects these for you.
• Clients: Build and Maintain a regular cadence of client conversations and discovery participation. This is the only way for you to have firsthand knowledge and build that famous product sense that matters for building the right value for your clients. After you finished your first 20 calls, find a way to spend 1-2 hours each week in direct contact with clients (if you’re working on an existing scaled product). Ensure that your team regularly spends time directly with clients. Especially as they’re exploring new solutions.

In the second month I suggest to adapt the reflection questions slightly and go beyond initial observations and setup into action steps:

Reflection questions week 4 to 8:

What have I learnt this week about my Team, Stakeholders, Company and Market and Clients? Who might help shed further light on these insights? What is the most impactful small action step I can take to act on these insights? How might I set myself up to use these insights and show an early quick win success after 90 days?

What is my working theory of what success means in our organization? Am I clear on both strategic as well as financial priorities for my organization? In what way has my understanding evolved compared to the previous week? What can I do to get more clarity on this? Are there any signs that something about these priorities is shifting in our organization?

What can I now see as the most impactful way to help my team achieve that success?
Is there any structural change needed to enable my team? If so, what do I see and how might I vet this? Whose support would I need for that? What first small step will I take next week?

What can I do to become a more effective leader?
What feedback was shared with me that I want to take action on? Have I found a good mentor or coach helping me navigate this? If not, where might I get the support I need for my own development? What first small step can I take this week?

What am I missing?
Do I have an intuition about something here? Who might help me find a blind spot?

A template for structuring your week 5-8 reflections can be downloaded at the bottom of this post. Before filling it out, read the week 5-8 section again.

Week 9-12: Leadership Alignment & Action

Primary Goal: In your third month you want to start making contributions that set you up for continuous product success. You want to make sure that you’re delivering on the core two jobs you have to perform for your organization: Define Success and Deliver it with your Teams. This is about cementing your leadership presence and setting direction for the future.

It means you set up systems that allow you to figure out what and how to build, ship and scale profitably and what to sunset in collaboration with your teams. You work to ensure your teams understand how they are building value for customers that translates into successful business for your organization. You figure out how to do this in a highly uncertain and constantly changing context.

Team: Your goal continues to be building relationships and trust intentionally. You want to keep listening for the struggles and issues your team members are facing and seek to find patterns and systemic issues that you can address. You will have also observed enough interactions to start actively coaching and developing your team members.

• Keep having your 1:1s. Introduce personal development goals. Intentionally coach people to develop their strengths and find ways to address weaknesses and skill gaps.
• Pick up a topic from the Product Org Fitness Test and start addressing it with your team. If you still need to finish addressing last month’s topic, do so if it keeps being a major blocker or enabler to the success of your team.
• Introduce a strategic conversation agenda item into an existing team meeting (if this does not exist yet) to get your team into the continuous habit of thinking and acting strategically, and to keep a focus on strategic and financial contributions. Ideally this builds a loop between discovery insights and smart strategy insights that get surfaced to the rest of the organization.
• Implement of propose changes to the product operating model or org structure (if needed). You’ll identify these by asking yourself (and your team!) what is blocking your teams from consistently delivering on your success definition.
• Ensure your team knows your leadership principles and expectations clearly. Ask them for their feedback and thoughts on these.

Stakeholders: Keep talking to your key stakeholders. Your goal is to listen for shifts in their priorities and challenges in their team’s interactions with yours. Attempt to find good collaboration options where win-win approaches can solve any lingering conflict. Also listen for potential goal misalignments and try to find ways to address them in a win-win fashion.

• Talk to your manager about the first two months. Ask them for their feedback on what they see you do well and what they wish you might change, start or stop doing.
• Talk to your stakeholders about the first two month. Ask them for their feedback on what works well in your collaboration and between your and their teams. Ask them what they wish you might change, start or stop doing.
• Present a 90-day synthesis to your leadership team: what you’ve learned, where you’re headed, and what you need from them as support. Present any quick wins you and your teams were able to secure to date.
• Communicate and align any proposed changes to your product operating model or org structure.

Company & Market: Keep listening for shifts or surprising little contradictions to your understanding of major industry trends, strategic priorities or competitor behavior. Keep asking yourself if there is anything new that deserves attention.

• Establish a regular cadence of stakeholder updates and discussion of strategic questions that need clarification
• Define the next 6-12 months of focus for your product organization. This includes strategy, capabilities and culture.
• Communicate how changes to the product operating model might impact stakeholders and ask them for their feedback, concerns and support.

Clients: Keep up a regular cadence of conversations and use opportunities to meet clients in person where they present themselves. Ideally in the context where they choose to buy and use your product. You want to keep being curious about better ways to serve your clients and what adjacent opportunities you might turn into another profitable business delighting your customers along the way.

Reflections: In the third month I suggest to further adapt the reflection questions slightly and start reflecting on things you can stop doing to free up time and focus for the main priorities of your product teams:

Reflections for Week 9 to 12 (and beyond):

What have I learnt this week about my Team, Stakeholders, Company and Market and Clients? Who might help shed further light on these insights? What is the most impactful small action step I can take to act on these insights? What is the most surprising new signal that might deserve further investigation?

Does my definition of success in our organization need updating? Has anything shifted on strategic or financial priorities for my organization? What can I do to get more clarity on this? What question (if it got answered) would unlock meaningful progress? What might I need to know to make the right decision? Who should I involve and share this with? (The idea is to collect perspectives and extract decision dimensions).

What can I now see as the most impactful way to help my team achieve that success?
Is there any structural change needed to enable my team? What is the mood and level of psychological safety in my team and organization? Do I have the right skills in the team? And does my team setup make sense? What can we stop doing to free up time and focus for our main priorities? What part of this needs attention? Whose support would I need for that? What step will I take next week?

What can I do to become a more effective leader?
What feedback was shared with me that I want to take action on? What topic do I want to bring into my next mentoring or coaching session? What do I keep being stuck with? Has there been conflict with a team member or key stakeholder? If so what steps can I take to repair that relationship and increase trust again? What action step am I committed to take this week to invest in my personal growth as a leader?

What am I missing?
Do I have an intuition about something here? Who might help me find a blind spot?

A template for structuring your week 9-12 reflections can be downloaded at the bottom of this post. Before filling it out, read the week 9-12 section again.

Beyond the first 90 days

Keep up a regular reflection time in your calendar. You can keep looking at the reflection questions from week 9-12, and you can also start phrasing your own.

Success in your product leadership role is the result of many months of disciplined approach to solving user and business problems keeping the main product risks in mind: (Value: Will people choose to use this? / Usability: Is it usable? / Feasibility: Can we build it? Viability: Does it work for the business? / Ethics: Should we build this?)

In order to do that with a team of people you need a shared, aligned and vetted version of what success looks like in your context. From a customer, strategic as well as financial perspective. And a team capable of executing on this. This does obviously require them to have the Product Discovery, Delivery, Product Growth and Product Leadership skills. Your job is to make sure they have both a success definition and the right skills, setup and tools to succeed.

Whatever your operating model is (and there are many that can work), you need the team focused on finding the right problems to solve in a way that customers love to spend enough money on so you can have a sustainably successful business. And then bring this together, inform and align this with the strategic goals of your organization. First work within your existing system to keep discussing discovery insights, strategic considerations and the financial outcomes of your team’s contributions. Then find where updating it would help unblock the success you all want as an organization. These systemic changes take time and buy in from the stakeholders around you. You earn their trust for this work by first showing meaningful success towards strategic and financial outcomes.

In summary

There is not one “correct” or “wrong” way to go about your first 90 days in a new product leadership role. Product leadership means operating in high uncertainty contexts (market, client behaviors, strategic context) and achieving success with a highly dynamic and constantly changing system (your organization and team and their systems of operating).

The best you can do is to keep focus on the core two jobs you have to deliver on: Identifying, defining and aligning what success looks like in your context, and then delivering that with your teams. You do this by regularly pausing, reflecting, choosing a next step and intentionally building a product organization that can succeed in your context.

Creating successful product outcomes is a group sport. One that benefits of taking diverse perspectives into account. It is as much an art as it is a science to navigate all the human relationships and power dynamics that enable you to uncover customer value and deliver business viable solutions that are feasible to build, usable and ethical.

If you report into a non-product leader, it is not uncommon that they struggle to help you develop as a product leader. Then it becomes extra important to find peer support, a mentor or a product leadership coach outside your organization.

But none of them will do the day to day product leadership job for you, and none of them will know your context as well as you and your team. This is why it is so important that you regularly reflect on the questions above yourself. And then lean on mentors and coaches for the difficult topics you keep getting stuck with or want support with. As a coach I can tell you that the answer most often already lies hidden in yourself.

Being a Product Leader is a hard role. You don’t need to (and you honestly can’t) create great product outcomes on your own. Help yourself by regularly reflecting and by intentionally setting up the support network you need. If you’ve established that in the first 90 days you’re setting yourself up for success.

One final thought: This article is me “Working Out Loud” on a way to make sense and set yourself up for success in the first 90 days of your new product leadership role. If you see something that is obviously missing, or you see a part of this in a completely different light, please leave a comment. I’d love to hear from you on this!

Cover Photo by ThisisEngineering on Unsplash

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If you want to download some reflection templates that might help you get started, here they are:

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If you would like to explore this more: reach out for a free coaching session with me.
I coach, speak, do workshops and blog about #leadership, #product leadership, #AIEthics #innovation, the #importance of creating a culture of belonging and how to succeed with your #hybrid or #remote teams.

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