It’s been three months and you realise that the company you are now working at isn’t what it sounded like on paper. People seemed great during the interviews, opportunities were abundant but now that you’ve had a chance to go in deeper, it’s not what you had imagined nor what you were promised.
I often wondered if there was a better way to cut through the surface and get to the truth during the interview process.
Then I turned to user research.
User research tells us to break down our questions into research questions (what do you want to learn) and interview questions (how will you learn it, while getting accurate meaningful answers). This approach helps to elicit the responses that will paint the most accurate picture about the company, its people, and the role itself. This is especially important for Product Managers since the role can vary so much from company to company.
My 3 key research questions:
- What will my role actually entail?
- What will my boss be like?
- How much agency will I have to do what I believe is right?
What will my role actually entail?
This is table stakes; if I won’t get to do the things I want in this role, then the rest doesn’t really matter.
Describe the last project or feature you worked on and the role you played.
As with user research, if you ask a question directly, the answer you get may be aspirational. For example, if you ask someone how many times they go to the gym, they may say 3–4 times a week. But if asked another way, how often did you go last week, you may discover that perhaps it was much less than 3 times. Humans naturally want to put their best foot forward. In an interview, if the interviewer likes you then they most definitely are doing this to attract you to the role.
So ask them to describe history instead. Ask this question to a current Product Manager without anyone else in the room. Ideally they will be your peer. If one isn’t available, ask the interviewer the same question and see what you get.
What is the hardest thing about being a PM here?
I want to know whether the answer to this question would leave me excited or wanting to run away as soon as possible.
If the hardest thing is building empathy with a distributed team, that would excite me. It’s a challenging problem that can actually be solved.
If the biggest challenge is convincing engineering to build something that may be a red flag. If engineers are constantly pushing back, it can be a sign of a lack of focus, leadership incapability, or that people in the company believe that they are working on the wrong things. These underlying issues are fundamental problems that should be avoided.
How are releases managed and how often do you release?
Faster releases are better.
The faster you move, the faster you’ll learn. The “move fast and break things” from Zuckerberg comes because of this. You may not necessarily want to “break things” but the more you do in a short period of time, the more you’ll learn and grow professionally and personally.
You don’t want to be stuck in a company that takes 4 months just to launch a feature or product.
What are the company priorities for the next year?
Are they working on the right things? Does the roadmap align with the vision? Is there focus, or is the company trying to do too many things?
If you are coming into a senior role, you may be asked to help with strategy. If the executive wants you to help bring focus and build a strategy that aligns with the vision, that’s a green flag. You know that they are committed to bringing focus and that’s a sign of a healthy executive mindset versus trying to do too many things.
However, if you are coming into a junior role, you may not have the influence to change the direction of the company.
Stay away from a company that lacks focus and can’t align their strategy to their vision. It will be a constant uphill battle and at the end of day you may not have anything to show for your work when you are ready to leave because the company shifted direction so many times.
And finally, does the response excite you?
What will my boss be like?
People don’t leave companies, they leave managers. It’s a cliche for a reason.
Your direct manager defines your work environment day to day, your compensation, team dynamics, etc. Will they have your back? Will you cringe or be excited to go to work?
You can’t exactly afford to leave all of that up to chance.
Understanding the person behind the title is not only critical, it can be life or death in a job.
Tell me about the last time you fired someone.
This is my favourite question.
In the past I have heard managers talk about firing a**holes. This could go two ways:
- Bosses firing people who they didn’t like. Red flag.
If someone can’t handle being challenged, then the likelihood of you being able to affect any kind of change is very slim. How will you voice your concerns? How will you advocate for what you believe is the right thing to do? And how will you find the best solution to a problem if there aren’t multiple views and opinions on the table?
2. Bosses firing people who couldn’t get along with the team. Green flag.
I have come across individuals who put themselves before the company. For example, an engineer who wants to the use the latest technology because it’s cool even though it doesn’t make any business sense. Or someone who thinks they are the smartest person in the room and doesn’t want to listen to anybody else. You want a boss who is able to identify such behaviour and take steps to change it via feedback sessions, improvement plans, or if necessary, removing them from the company.
You’ve got to remove the weeds from the garden for the other plants to thrive. If the company isn’t doing that, is this a garden you want to be part of?
What have you learned from your previous job/role that you’ve implemented in this role?
Is your future boss self aware? Do they have a learning mindset? Have they had meaningful life experiences from which you can learn from; do they have something to teach you?
But also, is your future boss humble enough to talk about their challenges and mistakes?
Someone who is self aware and can talk about how they overcame challenges is a great person to learn from. You can learn from their mistakes rather than making your own. These people also understand that making mistakes is part of learning and growing and will help you not make the same mistakes over and over again instead of pouring a bucket of blame on you.
Find these people and keep ’em close forever.
How do you onboard new PMs?
If your first week involves getting in front of customers, it’s a signal that this company really cares about the voice of the user. As a Product Manager, one of the hardest things to do is to get out of the office and go meet customers. So taking advantage of someone else coordinating this for you when you’re not trapped in meetings all day is a huge bonus.
This also shows that your boss and the company realises that to be a great PM, you’ve got to put users first and they are doing this to set you up for your success. Green flag.
Tell me about your most successful relationship.
Great product management is 60% substance and 40% style. “Style” accounts for the soft skills needed to build strong relationships.
It takes a lot of time and skill to build great lasting relationships and if your boss is able to do this, they likely understand the ingredients needed to make this happen. This is what you want to learn from them. You won’t be able to gauge how they work with others during the interview process but asking about their successful relationships may help you understand them a bit better. Especially their values and how much effort they put in to build successful relationships.
What has contributed to your success so far?
“I’m the smartest person in the room.” Red flag.
Any response that is essentially saying that they know more or are better than anyone else means they are not great Product Managers. PMs are generalists and our job is to get the experts collaborating to find the best solutions. Thinking that you know it all means you’re likely not doing your job well.
“I’m lucky I guess.” Red flag.
Any response that doesn’t talk about their strengths and attributes their success to only others or things out of their control means they aren’t self aware. One must be aware of their own strengths to be able to leverage them effectively.
How much agency will I have to do what I believe is right?
All the ‘boss’ questions will also help to answer this one too but I split it out into its own research question because I don’t want to work for a company where I can’t advocate for what I think is the best course of action.
How are decisions made? / Tell me about the last time a major decision was made.
If they mention too many people, red flag. If they mention too few people, red flag. If they don’t talk about the ‘why’, red flag.
Decision making is probably more art than science, especially at a startup where data may be scarce. When little data is available, you may have to rely more on your hunches. But hunches can be wrong and if not enough input is gathered from all teams, the hunches can be highly biased. If this happens enough times, where is the company really going?
If too many people are involved, how fast are the decisions being made? Being in decision limbo can really demoralise the team and kill any momentum.
You want to be at a company that tries to strike the difficult balance between making the right decision and making a timely decision.
Who is the highest person on the Product team and are they part of the executive?
A Product Manager who is unable to get a clear picture of the entire business isn’t effective. And if someone from Product isn’t part of the executive then the team is missing out on a lot of valuable information needed to build the right thing. How can you maximise business outcomes when you aren’t aware of the high level workings of the business itself?
Those who have never worked in Product don’t know what Product Managers do and how to effectively do their job. If the executive is made up of people like these, they won’t know how to string the pieces together to devise a kick-ass product strategy. This signals that the C-Suite doesn’t understand how Product contributes to the bottom line and often it can also mean that Product isn’t a priority.
Red flags. Red flags.
Working at a company that doesn’t understand and/or value the role you’re in means the amount of impact you’re able to have is limited. If the most senior Product Manager isn’t equal to the Head of Sales, Head of Marketing, or Head of Finance, they won’t have the same amount of influence on the business leading to a sub-par product.
How is the roadmap prioritised? Tell me about the last time you prioritised your roadmap.
A great Product Management team co-creates the roadmap with stakeholders. This includes you.
You may not own the roadmap but if you aren’t helping to shape it, you’re only doing half the job of a Product Manager. Your input is valuable and a team that doesn’t value your input isn’t worth joining.
Also see How are decisions made.
How many times has direction changed in the company? Tell me about the last time this happened.
Changing direction too often can be detrimental to a company. You’ll never stick to anything long enough to be able to validate/invalidate an idea. But this is also a sign of possibly too many cooks in the kitchen or too few. Either way, you may not have the freedom to row the boat in the direction you believe is the right path because you’re constantly changing direction and which way is North may not be clear.
Can they really stick to their decisions? Do they know what they are doing? Are they doing enough research to know what they are doing?
“The only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle.” — Steve Jobs.
Use these questions to find a place that you love. Then let the great work happen.