This edition of PM Teatime is with Olaseni Adeniji who is a Product Manager at Microsoft. Olaseni previously did a PM internship at Microsoft and has written very successful articles on his experiences transitioning into Product Management.

I spoke to Olaseni about his career in Product so far, and his love for writing and content creation.

Some of the interview highlights include:

• It is so important to deeply understand the PM role as part of your interview preparation by speaking to many different PMs at lots of different companies.
• Personal branding is a great investment as it can provide many benefits throughout your career and bring many opportunities to your door.
• Be as spongy as you can in life and have the mindset that there is always something someone can teach you – this also keeps you humble!

Read our full conversation below 👇🏼

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Hassiba: So what was your route into Product and how did you find out about Product Management as a field in general?

Olaseni: So I never knew what Product was, and I never planned to do Product Management. I went to school to do electrical engineering actually, but one of my uncles had told me: “Hey, why not do Computer Science because there is a broader range of things you can do after.” So I decided to do CS and my assumption was that if I went into this field I would just naturally become a Software Engineer after that, and that was just the natural route. But I am also the type of person that wants to get different experiences and try different things, so I did a few different internships to figure out what else I could do. The first internship I did was a 3D printing internship, and I think that was just a way for me to kind of find out what I like and what I didn’t like, and so I did that- and it was fun. But, you know, I didn’t think it was something I was gonna be doing consistently going forward. So I did some other stuff on the side as well, like some software engineering stuff with Facebook. I did enjoy these experiences and felt like I could do software engineering as a career if I really applied myself, however, I didn’t love it and I didn’t think I was super amazing at it; so I applied to SWE roles as a backup.

But I was still looking for other things I could do. I did a product strategy internship which was cool, and then I did a data visualisation internship which actually was the route that I found out about PM. I had to give a 5-minute presentation which was 20 slides with no words – it was just images and I talked through it. For this, I needed to understand everything that was happening surrounding this project I was working on, like, where were we getting funding, what was the end goal and who the users were going to be. So it was kind of like my first taste of PM- talking about the value proposition and stuff like that. 

I found a couple of other people that wanted to do PM and started talking to them, I also reached out to people on LinkedIn and realised that this could really be something I wanted to do as a career.

I actually enjoyed that presentation more than the entire internship, so I wanted to find a role where I could do something similar to this. Now I didn’t actually know that what I was doing was PM because I don’t think Product was as well-known as it is now. I think it’s definitely more popular than it was around 3 years ago.

So after that, I found a couple of other people that wanted to do PM and started talking to them, I also reached out to people on LinkedIn and realised that this could really be something I wanted to do as a career. So I did the regular stuff of reading Cracking the PM Interview, Swipe To Unlock, and doing mock interviews.

Throughout the process, I met this Nigerian woman that was a PM at Google.  She mock interviewed with me and gave me a bunch of feedback. I ended up interviewing for Microsoft, Google, and some other companies for various PM roles – I got to the final round of Google but didn’t get the offer, but I got the Microsoft one! So I did the internship at Microsoft and ended up having a blast, I had an amazing manager and worked with really great people. I did explore some other PM roles at other companies after the internship, but I decided to stay with Microsoft and I have been there for almost two years now!

Hassiba: It’s very cool that you had the determination to keep trying new things until you found a career that you liked!

So what are you working on at the moment at Microsoft? And what is it like to work there in general?

Olaseni: So the team I work on primarily works on a Kubernetes platform and one of our goals is to enable other companies to run their containerised applications seamlessly. So it’s like a B2B space where we develop a platform to help customers run their applications, for different reasons like performance or any latency issues – people can of course do this in the cloud, but there are a lot of companies that have restrictions over the sovereignty of data, general latency of data and also people just not trusting the cloud with their data. So we do a lot of things on-premise for people too, but yeah that’s primarily what my team does!

I’ve also done a bunch of different things too alongside this, I’ve done some competitive analysis for my team, I’ve worked on open source stuff for my team as well too, and I talk to a lot of customers and write documentation. So as you can probably tell, PM tasks are super broad and there are a lot of different things that come up… there is a bit of everything!

Microsoft has so many different verticals and is involved in very different industries and very different spaces so being able to have access to all of that is just so great.

But being a PM at Microsoft is very interesting because there are so many different layers to it. One thing I realised in my internship is that Microsoft is like many different companies inside one company. There are around 200,000 employees so you can imagine that teams vary and cultures are different even within the company, so it is very interesting. And a great thing about being a PM at Microsoft is that you get to work with people that are really impressive; some of the PMs and people that I have met have been amazing – for example, I met Scott Guthrie, the executive VP of the Cloud and AI group at Microsoft! But as I said the pace and culture can be quite varied, fast in some teams and slower in others.

But Microsoft has so many different verticals and is involved in very different industries and very different spaces so being able to have access to all of that is just so great. Microsoft just had Ignite, which is their big conference and there were so many different announcements about all of the different things that the teams are working on. It’s just crazy and exciting to be amidst all of that!

Hassiba: I can imagine being around all of these exciting areas is amazing and so inspiring! Is there potential to move around as well within Microsoft into different areas and verticals?

Olaseni: Yeah, because there are a lot of different areas it is possible to move around. If you get bored working in one space and want to do B2B or B2C, or work in Cloud – Microsoft does all of those different things. However, it is not as easy as you may first think – you still need to network and interview and prove that you have the skills to work in that particular area, but it is definitely doable if you put your mind to it because all of the opportunities are there!

Hassiba: What are the biggest challenges you’ve faced as being a PM and how have you overcome those challenges?

Olaseni: Whoa, that’s a good question. Well, I haven’t overcome all of my challenges yet, some are still works in progress! But one thing that does come to mind as being a big challenge as a new PM is the sheer amount of meetings in your calendar, it can be very overwhelming. Like it is feasible for most of your week to be blocked up with meetings, so I think that is just something to be aware of. I think if you’re thinking about being a PM, you need to question if you want to have that much interaction within your work. Do you enjoy having lots of meetings? If you don’t then it is something to carefully consider before committing to a PM role. But I think for me, I like to manage my calendar by intentionally adding in focus time. So I block my calendar a lot… sometimes two weeks in advance. For example, I barely take meetings on Tuesdays so that I can actually do the work that is discussed within my meetings and catch up on everything. So intentionally blocking out time definitely helped me. There is also the challenge of knowing which meetings I should be present in and which I shouldn’t. Like, could this have just been an email? Because there are always different people pulling you around. 

There are so many moving pieces that you have to manage within 8 hours a day, 40 hours a week. Navigating all of these things can be hard and does take some time.

Another challenge that still relates to meetings is the constant change of context because there are so many things you have to balance at once. And you’re asking yourself: how do I even stay on top of this? Because I have customers that I have to work with, the development of features that you have to think about, you have to drive the many meetings and make sure progress is being made, there are so many things to think about! So there are so many moving pieces that you have to manage within 8 hours a day, 40 hours a week. Navigating all of these things can be hard and does take some time.

I would say the final challenge is learning to influence people from a lower level.  For example, if you want things to be moving at a quicker pace, or you’re wondering why people have made certain decisions you disagree with. It’s important to be in a culture that allows those conversations to take place and be able to express how you truly feel so you can make your individual impact. As a PM we’re taught that having as much data as possible is a good way of influencing decisions – so I think taking this on board does help. But it can be frustrating because sometimes even if you have the data, it can still be hard to influence prioritisation and decision-making.

Hassiba: Yeah, I’ve definitely heard that phrase within PM that you’ve got to be able to influence without authority, especially as an entry-level PM, and be quite good at persuasion. I think people sometimes underestimate the importance of soft skills within the PM role.

Olaseni: Yes definitely, it does depend on who you are talking to and dealing with, as there can sometimes be clear hierarchies. And being in a situation where the other person is completely closed off can be tricky, and it can be difficult to know how to handle it, like when do you escalate and what does this look like? It’s all part of the nuances of being a PM!

Hassiba: Of course! So what was the recruitment process like for you at Microsoft? And what tips can you suggest to others who are preparing for PM interviews?

Olaseni: So I think about PM interviewing in different layers. Firstly, I think one mistake people make is that they expect for the process to be super smooth, they go right into reading Cracking the PM Interview, and then boom, they get an interview! That is not a bad route, however, I don’t think it’s ever that easy. I think it’s really important to first lay some groundwork and have lots of different conversations with PMs working at various companies and on different projects. You will then start to get much more of an understanding of what the role actually entails and if it actually sounds like something you like. So starting off with getting that context is really important in my opinion.

I think when you get that context it really helps you a lot. Now, when you go to read Cracking the PM Interview, everything comes together. It’s just a lot of synergy. So I think that learning as much as possible would be my first step, watching YouTube videos, just whatever you can. And then the next step is to definitely start reading. Definitely Cracking the PM Interview, and Swipe to Unlock is my second one, and I really like that second one because if you’re very technical, it can be very hard to explain things, but that book helps you break things down like you can explain what an API is to a four-year-old, it’s just remarkable. And if you are not technical, then it helps you understand, technical concepts in a way that you can break it out to anybody as well. So I think those two books just really help, they give you perspective on how things are monetised and how things are measured, which is something you need as a PM. 

Learning as much about the company and its products is really important.

Then I think another important step is to make a shortlist of companies that you want to focus on and then started learning about them. Most of the time the company is going to ask questions related to themselves; for example, Google could ask how you would estimate how much Google makes from Gmail, and Facebook could ask you about Instagram Shops. So learning as much about the company and its products is really important. Then you need to start thinking about how you will answer the questions, exploring the many different structures you can use to form a coherent answer. Once you know this you can then start to mock with people and get feedback, both from peers and other people you meet that may be higher than you – this feedback is really valuable. Then when it comes to the actual interview you just have to hope you get a good interviewer or good questions and that the stars align!

Hassiba: Definitely solid pieces of advice. I think the PM interview is just infamous for being a notoriously hard interview to prep for!

Olaseni: It’s very, very notorious like, oh my God.

Hassiba: I see that you also like writing about career and tech topics, and you have a blog on Medium as well. So, what inspires you to do that, and how does that help you within your own PM career?

Olaseni: Ah, it really helps a bunch, to be honest. There are a few different reasons why I decided to start writing, the first one being that I heard personal branding was a positive thing and that everybody should be trying to do it in some form. I really took this piece of advice and ran with it. In 2018 I started writing and the benefits just became ridiculous – I put out content about my internship, like what my first week was like, and what I did. Then people at the company just started to know me even though I had never met them, and they were also ready to vouch for me because they had seen my work. I also liked the idea that my content would be helping people, international students for example, because I also was one, and sharing my experiences could help them. So I just kept doing it!

I felt like I was helping people and it was helping me, so it was a win-win!

I tell people that there are two ways to get into a company. There’s an active way where you actually apply yourself, then there’s also the passive way where you put out content, or you put yourself out there, and then the companies come to you. That’s how I got my Apple offer, I never applied – they just reached out. And Apple is like the pinnacle so I was just shocked that that happened. So all of these benefits just drove me to keep going. I felt like I was helping people and it was helping me, so it was a win-win! And I also just really enjoy conversations around career and growth, so I have so much interest in the space anyway.

Then the more I started to put content on LinkedIn, the more people would reach out to me and I would have lots of one-on-ones with people. I would get the same questions over and over again, so to be more efficient I just decided to write articles so that I could point people in that direction if they had some of those questions. I also really like Medium because I had more freedom to write about a variety of topics, and it didn’t just have to be career-related like LinkedIn is. So I have been writing for a while now, and I really love it, people sometimes know me for the articles I have written, even really senior people at my company, and that feels really cool!

Hassiba: That is really cool. It’s also great that once you have written an article, it lives on forever and continues to help people well into the future, which is amazing!

Olaseni: Oh yeah, and I think personally for me as well it’s a way to document my life experiences. Like I can look back and think whoa, did I really go through this? So it’s also personal as well as helping my professional life too.

Hassiba: So the final question I want to ask is if you have any mentors or people that influence you heavily in your life and what has been the most prominent bit of advice you have received?

Olaseni: So yes I do have some mentors, but I also don’t limit myself to who I learn from – I am a really spongy person. I love to see what people are doing successfully and try and be like them. I reach out to a lot of people and like to have conversations with lots of different people. I’ve had a lot of impactful chats, for example, I spoke to one of the co-founders of Wonsulting to learn more about content creation. So I do have some formal mentors that I meet with officially, but I also think a lot of my learning and growth in life has been through getting so many different perspectives. I mentioned before about the Nigerian lady who helped to mock for my PM interviews – she ingrained in me that I need to treat each mock like it is a real interview, otherwise you will have no chance of being successful. This really helped me, so just taking on board other people’s advice is so valuable.

And even the piece of advice I mentioned before about putting yourself out there and putting energy into your personal branding was such an important piece of advice that excelled my career massively. I remember that person also told me to be like a sponge to everyone and to approach life like every single person knows one more thing than you – this also helps to keep you super humble too you know?

I think the most successful people are the ones that deliver on what they said they are going to do.

Another piece of advice that was really valuable to me was the importance of being someone who follows through. I think the most successful people are the ones that deliver on what they said they are going to do, so I try to follow through as much as possible in my life and it has helped move me forward. So yeah, I’ve had a lot of really good advice that has been beneficial to my life!

Hassiba: These are great golden nuggets of advice, being a sponge in all situations is so valuable and you’re so right, there is always something new to learn. This is a great mindset to have.

It’s been so amazing to talk to you Olaseni, thank you so much for speaking to me!

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Make sure to follow Olaseni on Linkedin and Medium to keep up with both his career journey and articles!