Let me be upfront: five years ago I was a lawyer turned product and I was overwhelmed. It seemed product managers struggle despite following much of the best practices associated with product management, myself included.

Five years later, after growing with three startups, I was privileged to guide dozens of other product managers in 1:1 mentoring sessions. As I was concluding my last session, I’ve taken the time to reflect on the main topics that were raised. It then became clear that multiple PMs had similar challenges of which I’d like to share — ordered by the frequency of them being raised:

1. Establish a healthy Product <> Engineering culture
2. Stakeholders Management & Communication
3. Decide what to build next
4. Improve your product skills
5. Transitioning and nailing your first PM role

I’ll elaborate on each one, adding my take and approach to solving them.

#1 Establish a healthy Product <> Engineering culture

Engineering is the one group you’ll work most closely with, and as such - you want to make sure you’re having a productive and fruitful relationship. Gaining engineers’ trust will allow you to run faster and ship better results as a team.

Following are several ways to get there:

Involve Engineering as early as possible

Your Eng. lead is not a stakeholder, rather your closest sparring partner. The more of the mind melt you have, the easier it’ll be to later rely on their buy-in and execution. Avoid presenting your team with a fully-baked epic and expecting them to deliver. Doing that will lead to you having a list of Assomption about complexities and possible solutions and a less committed Engineering team.

Instead, lay down the “why” and high level “what” and then pull your Eng. lead to be part of the brainstorming phase. By doing so you’ll achieve 3 things:

1. A sparring partner with a deep understanding of your product to challenge and provide valuable input.
2. Time estimations to help you in making better trade-off decisions.
3. Getting the team’s buy-in and responsibility as they were part of the process.

Schedule a kick-off meeting

When it comes to important epics, I tend to prepare a short presentation to cover what we’re building and why. I then share it with the Eng. lead to add his part with high-level planned tasks and responsibilities.
Once ready, we schedule a kick-off meeting with the team where we share how this epic serves our overall vision and OKRs while the Eng. lead explains about high-level architecture. This is also an opportunity for the team to ask and make sure they understand what they’re about to build.

Take part in Engineering retros

Participating in retros will give you an overview of what’s worked well and what’s not, based on the engineers’ point of view. It’ll also allow the team to give you direct feedback and by doing so — improving you as a team. That said, don’t force yourself in, gently ask to join and explain the reasoning behind it.

I’ve tried 2 different approaches to handling retros, from “Score, Continue, Stop, Start” to “Score, Liked, Learned, Lacked and Longed For”. I find the latter more useful as it has proven to yield better and more open discussions.

I used TeamRetro before and can recommend it as a straightforward tool for running remote retros.

Pro tip: have a rotating moderator, don’t own these sessions. You are a team and them being actively involved increases the responsibility notion.

Cultivate personal connections

Strong communication and interpersonal skills are a product manager’s strong suit. Schedule a 1:1 and go the extra mile to learn more about your colleagues — What are their aspirations? How do they feel? Is there anything personal they need help with?

Great PMs I’ve known are ones that can cultivate relationships and store different ‘states’ for different people, genuinely caring and remembering to follow up on chats they had in the past.

Celebrate your teams’ work

Empower your team to demo their work in company’s next all-hands and offer them help in preparing, e.g. by doing a mock-demo session.

#2 Stakeholders Management & Communication

Having all the relevant stakeholders involved and up-to-date ensures faster and better delivery. Moreover, as a PM you need your colleagues’ input as they are the experts of their domain, e.g. Marketing when it comes to Go-To-Market strategies.

Here are several tips which helped me in ensuring team’s alignment:

Be digitally-transparent

Providing digital transparency in a post-COVID-19 world of remote work is more important than ever before. It allows your team to asynchronously be informed on what’s happening.

There are many tools out there, yet my favorite ones are Asana and productboard. Asana is predominantly a team collaboration tool, allowing others to know what everyone is working on. Productboard helps in aggregating and tracking users’ requests prioritized by frequency and is another source of input when deciding upon future epics.

Documentation is another form of digital transparency — either via a Google Doc, a Notion page, or whatever works for you. One example would be a Product Requirements Document, aka “PRD”, aimed for everyone to understand how a new feature addresses customer problems and drive product strategy forward. I’ve recently started using Figma’s PRD template, as a concise modern model to replace the old lengthy PRDs.

Be physically-transparent

Bringing your current plan to life, e.g. with a physical board, will help those who are not religiously following your Asana board to know what you are currently working on. Another great side-effect is that people will randomly approach you with suggestions and thoughts they have.

Have a bi-weekly 1:1 with your team’s key stakeholders

Having recurring sync meeting enables the team to surface any non-burning issues that are of concern while avoiding back-and-forth Slack messages. It should include Design, Engineering, Support, Operations, Marketing, etc. By ‘team’ I’m referring to the set of people directly working together on the product or area of the product.

Pro tip: don’t be rigid about it. Feel free to skip a 1:1 if there’s nothing on the agenda. That said, these informal sessions tend to be invaluable when it comes to strengthening personal relationships.

Public internal launch

Do internal live demo during all-hands meetings followed by a Slack message on company’s main channel, e.g. #general, about the latest release and how it affects your customers.
Pro tip: don’t forget to give shout outs to everyone that took part in shipping the feature.

Side note: in case it’s a big feature, consider having an internal alpha testing session where you invite everyone to get a sneak peek while providing feedback.

#3 Decide what to build next

PMs are responsible for ensuring strong strategy, drafting and prioritizing product plans, and leading execution that results in meaningful progress. Even the best-performing team won’t cut it if your strategy is wrong.

There are 3 parts to it:

1. Develop a long-term strategy

It’s imperative that you understand your company’s overall goals and objectives and how exactly does your team fit into the broader vision. You can read more about how to effectively do product planning here.

2. Break down stratégie into OKRs

OKRs stands for Objectives and Key Results, mostly known for its broad use at Google. Personally, I find OKRs as a pragmatist framework to staying laser-focused on what you should prioritize to hit your quarterly goals.

Defining the right OKRs is as important as setting the right strategy. Here you can find an article containing multiple examples.

3. OKRs to epics

Once you have a good understanding of your OKRs, you should ask yourself “which epics can your team build to move towards this direction?”. For example, if your company’s quarterly objective is to increase engagement, and you’re the PM at Facebook’s News Feed product, you might prioritize initiatives to improve content curation, or integrating Instagram Stories for Facebook users that don’t have an Instagram account.

After listing down your epics, you would need to prioritize. I use Intercom’s RICE framework, but you can use any other method that works best for you.

Being able to prioritize will require you to accumulate feedback from users, both qualitative: user interviews, feedback from client success, etc. and quantitative: DB queries, productboard, etc. This is also where you’d pull your Eng. lead in, helping you to contemplate solutions, and estimate time-needed, i.e. Effort.

A word about the prioritized list of work, i.e. roadmaps: you need to embrace the fact that your roadmap might and would change. That’s OK. Lemonade’s Head of Product, Gil Sadis, rightfully claims that startups are growing faster now than ever before, and sticking to a predefined roadmap for long periods can mean that you’re not iterating and adapting to your customers’ feedback and usage patterns fast enough.

#4 Improve your product skills

Most of us are coming from different backgrounds to our first product role. Although product roles differ depending on company’s size, market and industry — they all have common denominators when it comes to core skills: the ability to strategize and set a vision, being a clear communicator, have a strong product intuition and having a design and engineering aptitude.

You can either decide to double-down on your strengths, or compensate for your weaknesses — either way, here is a list of ways to do so:

• Books. Among my favorites: Zero to one, The Hard Thing About Hard Things, Influence: The Psychology of Persuasion, Hooked, The Mom Test, High Output Management.
• Blogs covering topics like user research, strategy, roadmapping, etc. Here you can find a list of 10 of the best product management blogs.
• Podcasts. Here is a list of 20+ Product Management podcasts you should listen to. This list is being maintained so it’s up to date.
• Use and drive inspiration from other top-notch products such as Asana, Dropbox, Slack, and others. There is no need to always reinvent the wheel — think what is your use case and reuse others’ best-practices. I find Webframe.xyz useful as it aggregates screenshots from multiple known SaaS products.
  Pro tip: whenever you encounter a memorable UX or design — take a screenshot for future reference. Especially in your early days, it will help you in forming your design sense.
• Try one new product a week. Immersing yourself in one new product a week can tremendously broaden your product outlook. By doing so, you’ll have a better understanding of what are the products that are currently being used as well as how they’re being built, allowing you to drive inspiration AND have them as a reference once they can be of use. Examples can be No Code tools such as Airtable and Zapier.

Pro tip: Every time you read a book, go through a blog post, or hear a podcast — reflect. Reflect on your past experiences and situations and ask yourself: “how can I apply what I am reading/hearing to a past situation?”

#5 Transitioning and nailing your first PM role

Becoming a Product Manager is lucrative, as many view it as their entry ticket into the startup world. Thing is, it’s not easy.

I won’t cover this topic in detail here as this can become an article of its own, but you can refer to this comprehensive piece by Eva Drago.

Final thoughts

Successful products are built and adopted by customers when a group of committed, focused, and passionate team members contribute to the best of their abilities. The PM plays a central role by gathering valuable intelligence from relevant stakeholders, customers, and markets and as such, uniquely positioned to tie all the pieces together.

When done right, product managers have the best job on Earth.

Happy to hear your thoughts, feel free to reach out on LinkedIn or Twitter.

Big thank you to Curtis, Dave, and Mirela for reviewing drafts of this article. 🙏

If you enjoyed this article, you may also enjoy this one:

• The Secret Approach to Working with Your Tech Lead. 🤔 Questions PMs and Engineering Leads must ask to foster a stronger relationship and a better roadmap