Product School

Ask Me Anything: Getting Comfortable With Ambiguity

Adrianna Berring

Adrianna Berring

January 09, 2023 - 18 min read

Updated: January 24, 2024 - 18 min read

This past month we had the privilege of hosting 6 incredible Product Leaders answer questions on the Product School community Slack:

  1. Niyathi Chakrapani, former Product Leader at Microsoft

  2. Prerna Kaul, Senior Technical Product Manager at Amazon

  3. Florian Weingarten, Head of Product at TIER Mobility

  4. Samantha Haveson, Senior Product Lead at Twitter

  5. Sameer Sawhney, Senior Product Manager at Amazon

  6. Rakshith Halevoor, Manager, Product Management at Amazon

October’s theme was getting comfortable with ambiguity. This is one of the most important skills to master as you get into senior Product roles, where you have to make big decisions with incomplete information. Here’s how these Product Leaders deal with uncertainty.

Bonus: read on for their insights on breaking into Product, passion for Product, practicing Product Management, organizational- and industry-level advice, plus final tips for aspiring Product Managers!

Getting Comfortable With Ambiguity

a turn sign pointing in two directions on a road. there are mountains in the haze in the background
How did you get more comfortable with ambiguity as you moved up the Product career ladder?


It’s crazy how you can trick your brain—I started associating ambiguity with good things, and literally smiling during uncertain times, which actually releases “happy chemicals” in your brain. I told myself repeatedly that I love working with ambiguity and uncertainty since it triggers the creative process. And of course, the more ambiguous problems I solved, the more confidence I built. Eventually, I became more comfortable with it.


In my experience, ambiguity can come in a few forms. Ambiguity around:

  1. The problem statement

  2. Who the customer is

  3. Organizational and environmental (i.e., the org structure & the people you work with).

The best way to get comfortable with it is by applying “progressive elaboration.” We know that there are a lot of unknowns and we also know that it is possible to disambiguate the easiest ones first. So I have found myself working my way up from easier problems to harder ones to resolve ambiguity over time.


Interesting one! I think generally the more you do something, the more comfortable you get doing it. Just give it time and don‘t stress yourself with not being able to address everything at once.


Product Management is the art of turning chaos into clarity. Oftentimes, it will require PMs to be highly ambitious in taking on an area that doesn’t have a clear direction. When you are working with ambiguity you need to rely heavily on communication and partnership among your team. The PM’s role is to focus on the why and be the voice of the customer. During times of ambiguity, bring everything back to the customer and their needs.



For me, the best way to prepare myself and my team is to think through all kinds of risks that the team or product might encounter in near future and respond to the situation instead of reacting to it. As they say, “change is the only constant,” I will say “Ambiguity is the only constant, so set you expectations accordingly!!”


Ambiguity and Chaos are 2 best friends of any PM. The more you lean into them, the easier it becomes to deal with them.

  1. Don’t be scared to ask as many questions as you want. No question is a stupid question. In fact, it drives clarity to many people.

  2. Feel free to say “I don’t know, I will get back on that”—take your time to figure things out and go back with an answer. The important part is not to drop the ball.

  3. Less is more! Most of the time complex problems have simpler solutions. When you feel the solution is getting complex, take a step back and reanalyze the “WHY.” That will simplify most of the things and an answer will be there.

Breaking Into Product + Career Growth

Tips on how to transition into Product?


My general advice is to think through your current strengths and skillset, and ramp up on what you are not as strong in. Coming from CX, you might have a strong grasp on the business and a great focus on the customer, but you perhaps aren’t as strong technically. 

So, learning about data structures, system design, data visualization, database management, etc. may be useful skills to stand out. The best thing to do pre-applying/interviewing is to pursue projects using your current skills while ramping up on other skills. It’s easier to convince someone you can do something if you’ve already done it! Then at the interview stage, prepare by highlighting Product Management skills you’ve already displayed and come up with 3-10 “hero stories” of times when you displayed those skills.


I would say being a Product Manager is an exciting but also difficult role as you have to deal with lot of ambiguity and people expect a PM to have all the answers. So, I would say in order to be successful as a new PM, focus on improving your communication skills and learn to get things done through your influence. In addition, you’ll have to be really good at prioritizing tasks or your time if you want to accomplish important goals.

What are five things to mention in our resumé when transitioning into Product from another domain?


  1. A good summary (in less than 3 lines) about your success.”1. Delivered X in Y years, leading X billion portfolio”

  2. Metrics – Quantify each line you write for your work exp. Never say “Delivered xyz product,” rather say “Delivered xyz product with x number of users or generating x million/thousands $$ in revenue”

  3. Use powerful words to show your leadership, such as Led, Delivered, Created, Incubated

  4. Impact – what is the impact to customers and business? Every company wants to know how your products impact the end users. They all know you can build products, but they want to know the Quality of them.

How do I get Product Management experience when I’m not in a Product role?


While methods and frameworks and the courses that convey that knowledge are a great starting point, I would try to get your hands dirty as quickly as possible. Either shadow (and support) a PM in the company you already work in or try to land an internship or entry-level PM job with a great mentoring structure. We have extremely talented PMs that transitioned from other roles within the company. This works quite well, as they already have the context of the product and org structure. Two incredibly important factors when it comes to PMing.

Any career-related tips for early stage PM’s looking to get more opportunities/interviews at top tech companies?


Interviewing is an important skill. It requires that you deeply understand yourself, your strengths, weaknesses, and your own career goals. I’d recommend having 3-4 key stories that reflect on your experiences (e.g. career, projects, etc.) and how you learned tangible lessons and drove certain outcomes. It would also be helpful to prepare for case-based product questions. Each company has a different approach, but at the end of the day, they are looking for critical thinking, collaboration, and Product Sense.

When moving from an individual contributor PM to a manager PM, what are some skills or systems that you use now that differ from when you were an individual contributor?


Great question!!! Few skills:

  1. Empathy –  Biggest thing, often we miss this. It is about listening and empathizing with people. Often people add emotions to their conversations and that might make the problem look bigger than it is. So listen, empathize and then add logic to it.

  2. Developing Bird’s eye vision – When you move up the ladder, one needs to focus on overall strategy and broader vision. You will be responsible for driving your team/line of products to success. So having that breadth will definitely help.

Check out: [Podcast] Skills to Take You From PM to CSuite


closeup of a handshake
What approach would convince you to have a 20 minute exchange with an aspiring PM?


If the aspiring PM can do as much work for me as possible to make the 20 minutes actually just 20 minutes, that is great. There is always some email back-and-forth involved in scheduling, so can you provide me a bunch of times that work for you first? And, PMs get a lot of emails, so can you make it clear in the subject line what I need to do? Things like that!

Now, some PMs may just not be interested in or have the capacity for helping, and that can’t be helped. But an email which is clear, short and sweet, and proactive gives you the best shot. It also doesn’t hurt to message them on LinkedIn, to send a follow-up email, etc., since people can just forget things too. Just don’t go overboard (I’ve done that!)

Does networking actually help?


Networking always helps. It helps you:

  1. Learn new things

  2. Market yourself

Passion for Your Product

Why and when have you ever moved on from a job where you were learning and growing? What is a good reason to move on?


There are many good reasons — more passion for a product, problem, or customer; to take a job more accommodating of your lifestyle, ie work/life balance, remote work, etc.; more alignment with a management style; more resources for development; and more!

I can tell you about my transition from Microsoft to ConsumerDirect! I am super interested in the product I am working on now: Hogo, a gamified consumer privacy and financial wellness app. The pull of the product and my new manager was so strong that I left a level of relative security to work for something more risky. In short, I was/am excited and passionate about the product!

Also, I moved from my first team at Microsoft to another with more organizational power. It was hard to get things done in the first team because we had too many dependencies, not enough resources, and frankly not enough organizational trust and respect. But the second team had lots of resources and people pitching ideas to do work for them! So it was easier to get things done and I could work more efficiently.

How do you keep yourself motivated to give the best work possible? For you, for your team, for your Product Org, etc?


A lot of the energy comes from working with the team. Just give it your best shot, stay authentic and yes, also vulnerable, and what you get back will feel amazing and amplify the energy you can give back in return. It‘s a loop from there 🙂

It also helps if you believe in the company mission and love the product and how it can enrich the lives of its users.

There are different phases in a Product Lifecycle, from inception to development to end of life. Which phase excites you the most?


I really like Product Development on a day-to-day basis and I really look forward to the product launch as that is culmination of months of effort by different teams. I also believe that “Product launch is not the end of journey, it’s actually the beginning!”

Day-to-Day: Product Practice

empty meeting room with wall-to-wall windows, a long table, and rows of rolling chairs
How do you manage meetings? What are your thoughts on daily scrum meetings?


Meetings are all based on what the team needs. You start with a problem/goal for any communication. Then, you think of the best way to set up that communication, based on that problem/goal and the communication styles of all involved stakeholders. If people respond quickly to email/slack/teams/etc. And if it can be a message, then it’s great to save people’s time. If it needs at least a short discussion, I’ll put 30 minutes on someone’s calendar. If it needs an in-depth discussion, you can make it an hour. And I always try to make the meeting the most efficient with an agenda and other prep work, and start the meeting out by reiterating the problem/goal and constraints.

Daily scrum meetings can be great for Project Management if you really have items to check in on each day — otherwise they can be a nuisance.

What frameworks do you use at Amazon to score feature improvements and new features to begin considering them for development?


It is typical prioritization question. I use a prioritization matrix  to rank these new features. Factors the impact these rankings (in order priority) are:

  1. Customer impact

  2. Revenue Impact

  3. Business Impact

  4. Internal impact

Stakeholder and Team Management

two people smiling and looking at a laptop screen
PMs typically get lot of asks from different stakeholders. How do you say “no” to these stakeholders and still keep them happy and aligned to your Product Goals?


Ideally you don’t even have to say no because you’re ahead of them. What is your vision for the product? What are customer insights? What impact can you prove from experiments? You can then align the topics you‘re working on by abstracting the asks of the stakeholders and show how what they want to achieve (outcome) would by covered by the topics you‘re working on anyways.

If you have to still say no, give them context. Explain why you will not be able to prioritize their asks and what you will deliver instead and why this is important.

Also important to note: Listen to them! They might have a point, a great idea or useful insights.

What techniques have you used to gain trust and build relationships with engineering and design counterparts?


Product should have a strong relationship with design and engineering, these are critical partners. It is important to align on goals early and often, and to have open communication in place when the team is facing change or new information. Communication is a key ingredient to building trust.

When projects get delayed, how do you let your partners down easy around timelines?


Communication is key when it comes to earning trust for project timelines or delays. Things happen, but if you can communicate honestly you will get stakeholders on the same page. Share out materials that describe (a) what’s causing a delay and (b) steps to resolution or new timeline.

The same goes for transparency with customers if you have made a public announcement. In some cases, it’s key to figure out when you need to be proactive vs. reactive for customer messaging.

Customer Research and Centricity

What techniques have you used to gather input from customers and validate ideas?


Great question. For gathering insights, I’ve used a combination of user surveys, in-person usability tests, shadowing customers, and customer interviews. For validating ideas, I have used pilot experiments (A/B tests where feasible) to get some data on our hypotheses quickly.


It is important to know who you are building for. In the beginning, it’s key to have a specific customer in mind. If you are building for everyone, you will wind up building for no one. When you identify your core customer, get out and talk to them. Gathering feedback in the form of interviews, surveys and community forums can be most helpful. You should talk to at least 6 people from your core customer segment to understand the customer needs and if your idea could help solve.

Suppose a product required by the customer doesn’t match your company values, but not building it puts you at a competitive disadvantage. Should you prioritize business opportunity or the organization values/mission?


In order to come with up with a right decision, I would encourage you to analyze the data available with you and listen to what your customers are telling you about their pain points! Don’t worry too much about your competition when you’re just starting to build out a new product and in addition, you can’t control what your competitors do. Once you analyze the data and understand the long term business benefit, you’ll find a way to align organization mission with the Product Vision.

How does user research work at Twitter for PMs when it comes to B2C products?


I’m a Product Lead on the Consumer team at Twitter. We take a few thoughtful approaches to gaining insights which is a combination of qual and quant. This often includes (1) Qualitative Studies with User Research (2) Quantitative Surveys (3) Running A/B experiments.  We are deeply focused on solving for customer needs and one interesting outcome of working at Twitter is leveraging feedback from the community, directly on Twitter.

Organizational and Industry-Level Advice

picture of mirrored skyscrapers from the ground, and angled-up photo. there is a blue sky with white clouds above the buildings
What are industry trends and competitive forces that will impact your product in the next 6-18 months?


There‘s a lot happening in the world right now that affects how people live, move and also how they spend their money. Sustainability might not be at the top of your mind anymore. No one saw the pandemic coming, which completely changed our challenges. Same for the war in Ukraine and rising energy cost. So this is very hard to foresee. Then again, I think micro mobility still has a way to go to be taken seriously as a mode of transport. So regardless of what happens around us, this is what we need to address most in our service.

How do you instill a culture of experimentation in Product Organizations? 


Great question. First is the setup — does your organization even have A/B testing and safe velocity rollout capacity/tools? A way to track & triage/prioritize experiment ideas, experiments currently being rolled out (make sure they don’t interfere). If not, you can help set that up!

Next is the process — when people have ideas, do they convert them into hypotheses? Do they track their hypotheses? Do they have indicators of experiment success? How are you harnessing the creative/ideative power of your team during individual work and group brainstorms/problem-solves to design experiments using the scientific method?

How frequently should an organization’s vision evolve?


It depends on so many factors – macro economic conditions, business environment, pandemic etc. There is no right answer here and given the pace at which technology changes, business priorities should be evaluated on a day-to-day basis.

How do you ensure your Product Team is working on the most important priorities for your organization?


First, the organization’s priorities need to be aligned with the customers’ needs. This can be investigated with user research, looking at existing data, and forming and testing hypotheses.

Next, there should be key performance indicators for each priority. We want users to be successful — how do we define success?

Then, teams need to be aligned to those priorities and KPIs. Depending on the structure of your organization, this may mean aligning with Product Leaders and asking them to relay this information, or it could mean meeting with the whole Product Team. But, the Product Team should not just be involved at the end — they should be involved from the very first step of understanding the customer.

Are business outcomes different in a company that has achieved Product-Market Fit vs an early-stage company?


Yes, absolutely. In the early stage, the company may be hyper-focused on creating product awareness and acquiring customers. For a growth-oriented company (think rocket ship), they will likely index on revenue, referral, and retention. The business outcomes will absolutely be different.

Final tips

Any final advice for aspiring Product Managers?


My best advice is to follow your joy. See what gives you real joy and do more of that. It’s hard to work on a product or with people you don’t believe in. It’s hard to be joyful all the time, but by being more present and paying attention to our bodies and minds, we can do more and more of the small things that give us that joy and feed our passion and energy.


My main takeaway from an 11+ year career in engineering and product has been to have the right mindset when approaching challenges in the role. You will continue to face setbacks as you rise the ranks and work on new ideas. However, with perseverance, the ability to be patient, and genuine empathy and curiosity toward your customers, the role can be a cinch.


My advice to aspiring PMs will be to talk to as many existing PMs from your target organizations to learn about their day-to-day job responsibilities and ensure that you really understand what you are getting into 🙂


My final advice for aspiring Product Managers is DON’T GIVE UP!! I’m not gonna say it's an easy path to transition into Product (if I did, I would be lying). But, you this wonderful Product Manager Community standing behind you to motivate and help when needed!! So keep your head down and destination in sight and keep going. You will get there!!

Updated: January 24, 2024

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