Community Wisdom: Dealing with impostor syndrome as a PM, interviewing UX/UI designers, roadmap frameworks, feedback for stellar reports, transactional email vendors, doing competition research, more
Community issue 79
👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Friday, highlighting the most helpful conversations in our member-only Slack community.
💥 Top threads this week
1. Dealing with impostor syndrome as a PM
Q: How do you deal with impostor syndrome as a PM? ↗️
Justin Goff: Usually by reading this classic from Reductress: QUIZ: Are You Even Good Enough to Have Imposter Syndrome?
Seriously, though, I've been doing this for a while now and I’ve worked with some amazing product folks, and we’ve all been hit by impostor syndrome at some point. Product managers are particularly susceptible. It helps me a bit to remember that, and also to remember that impostor syndrome is often a symptom of tackling big ambiguous new challenges. That's not to say it can’t metastasize into something nastier, though.
Lesley Heizman: I'm not sure if I have great advice here, but I face it all the time, especially if I'm switching to something new or diving into something new that makes me feel a bit uncomfortable. 🙂
I love this podcast episode for thinking about/managing your thoughts around that. Basically, it's about challenging yourself to do things you aren't comfortable with so you can grow. You won't be great at everything right away, but this is ok. You may fail and that's okay. Failure isn't bad as long as you learn from it!
Yaara: My experience has been that exposing my insecurities and the things I don’t know how to do neutralizes my imposter syndrome almost entirely. It takes some courage (and mindfulness) to get to a point where you’re not afraid to be vulnerable, but - trust me - it’s a huge strength once you own that vulnerability.
In my last 2 roles, I’ve been working on products in domains I have 0 experience in, facing challenges I’ve never faced before. I used to start customer calls by saying “my experience in this domain is as long as I’ve been in the company (which is not long), so please understand if my questions sound basic”, and that actually did wonders to my relationship with them 🙂
Lenny Rachitsky: Oldie but a goodie: This Week #5: Overcoming impostor syndrome
Josh Todd: Thank you so much for the advice! @Yaara your comment really resonates with me because I just joined a company in a new industry recently. I think that could be fueling this for me. In my last job, I was a subject matter expert so I always had a sense of how the market worked.
2. Interviewing UX/UI designers
Q: What are your top questions for interviewing a UX/UI designer? ↗️
– Greg Delhon
Bianca Gorini: EX-UXer turned PM here 🙂 Questions I always ask:
In case of UX: In what stages of the design cycle they are involved in (e.g. if they also to testing and UI etc. you know they are generalists, which in my scale-up case are essential)
UX/UI: if they have experience in mainly B2B or B2C, and what they prefer. Based on that you can define what kind of flows they have dealt with most and where they probably shine best
UI/UX: I ask them to explain their typical day, to understand how much they are used to working with devs. Essential in our case where we have a product squad team (Spotify model)
UI: What type of experience do they have inaccessibility and if they strive for AA (if they have some experience you will know they will take care of this in any deliverable)
UI: experience with design systems> if they have worked with or even contributed to a design system, it will much easier to onboard them in your current product dev flow. And! you know your interfaces will stay consistent (hopefully)
There are many more, but these are the ones I ask each time 🙂 Hope it helps!
Tali gueta: I used to manage 3 product designers (UX+UI). When I interviewed candidates I usually try to understand:
How they work with PMs
How they work with Developers
What is their process to validate designs before they hit production
How will they handle conflict around designs (let’s say we don’t agree on a solution they worked on, how would they respond to it)
Did they ever work directly with users, do they have experience interviewing and conducting interviews/usability testing
How are they keeping up with design trends, are they a continuous learner type of person.
As far as questions, it changes every time. I usually start with them explaining their past experience, then try to identify places where I can ask questions that will answer the categories above. If they don’t hit one of them, I would usually ask specifically (“Tell me of a disagreement you had with a developer and how you solved it”, “What do you do after you get a brief for a new feature, what is your next step?“, “How was it working with the PM in your current company?“).
Ray: Those are all great questions to ask. Also as a UX designer turned PM, I also like to ask behavioral questions:
Tell me about a project that has a lot of ambiguity. What happened, and how did you go about getting the clarity you and your team needed?
Tell me about a project that went sideways. What happened, and how did you get back on track? What did you learn from the experience?
3. Product roadmap frameworks
Q: What’s your favorite format for creating a product roadmap? We have our backlog on ClickUp and are a seed-stage startup. Do you have some examples that you could show? ↗️
– Dominik Mate Kovacs
Andrea Saez: Now, Next, Later—always. Focuses on the strategy and leaves room for experimentation and pivoting.
Ashley Rolfmore: I’ve yet to get a team or company to like the Now/Next/Later format.
I currently go for a few themes per quarter, with the idea that each theme should be scope agnostic. So there will be feature ideas tied underneath, but any, all or none of them may help the theme.
Josh: I like now/next/later an awful lot (and recommend it for most folks) but agree with @Ashley Rolfmore that many across the broader, cross-functional organization don't love it.
In addition, for very very early companies with small dev teams, I actually prefer a milestone-based roadmap. It doesn't scale and it doesn't last very long but:
Figure out the milestone you need to hit: getting a big customer live, shipping your v0, whatever. The milestone should be deeply meaningful which almost always means a big inflection in company value.
Write out, as clearly as possible, the use cases that are part of the milestone. If you have clear vision documentation like videos or interactive mocks, include that.
Make a "punch list" of literally everything you need to build to hit the milestone. Be rigorous in taking out anything that isn't actually required (no "nice to haves"!) but it'll still be a BHAG - hopefully, an inspiring one!
At the earliest stage, your roadmap is just the combo of a clearly articulated vision + a series of milestones.
Ashley Rolfmore: Ah, if you like story mapping, Josh’s technique works really well for that. As you have your big user story map, and you draw lines to determine each beta release before the big bang.
Josh: (Note that using milestone releases as your roadmap really doesn't scale: it'll burn your teams and you'll find yourself creating milestones that are disappointingly un-valuable. It really only works briefly and early.)
Scott: Now, Next, Later works great. As communication of your product’s direction and intent, here are some other examples: 7 Examples of Excellent Product Roadmaps.
John Koht: I agree with now, next later as a general tool for organizing and sharing your roadmap.
But, does a seed-stage startup need a roadmap? If you don’t have PMF, does a backlog matter? If you don’t have PMF, you should be laser-focused on that and have a much shorter timeframe for learning and iterating. Your roadmap will blow up within a month or two.
Scott: Yes. If you don’t have PMF, then your roadmap should be indicative still of what you’re doing to get to PMF. That can still be short-term in N/N/L or another format.
Uno de Waal: I found Now Next Later to be really valuable in articulating broadly speaking what’s important. I then had a different view that was broken down into priorities for months that were more actionable with milestones. So a combo of both. I think Product Board allows you to do this/have this view.
NNL also helps to not get too much in the weeds and is great for high-level articulation
Ashwin: For the year ahead: Q1, Q2, Q3, Q4
For next year: H1, H2
Anything beyond that is termed as “Year 3 and beyond”
Scott: We sure do @Uno de Waal and it all comes from the same info so no need to recreate either.
4. Feedback for stellar reports
Q: As a PM manager, what do you do if one of your direct reports has all positive 360 feedback and very little to no feedback for “opportunities”?
I think the employee is stellar as well. What should I do and/or avoid in my 1:1 feedback chat with the employee? ↗️