Delivering a roadmap a few weeks into the PM job

Step by step process to create a solid starting point

Hey BPL fam,

In today’s edition, we’re going to dive into a topic that a lot of new PMs entering organizations as their first product hire are grappling with.

Companies that are uninitiated in the “ways of product” demand a roadmap as the first deliverable of a newly hired PM a few weeks into the job, affording them limited time for due diligence.

We’ll explore what PMs can do in such situations. Let’s get into it.

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Building a roadmap as a new PM on a tight clock

I get messages like the following on my LinkedIn DMs:

“I just joined a company. The founder wants me to create a product roadmap in the next 2-3 weeks. How am I supposed to do this?”

It’s a tough ask.

A lot of PM content out there focuses on building a roadmap in more favorable conditions where the org affords the freedom to the PM to research, analyze, and deploy processes.

What makes matter more complex is that there isn’t one school of thought around roadmaps:

• some pundits hate them because they force product teams to become requirement managers and focus on output rather than outcomes.

• some claim that roadmaps can only be framed AFTER a clear vision, worldview, and strategy are in place. Without alignment, it’s all futile.

• others say roadmaps are impossible to create without product discovery.

• …and so on.

They’re not wrong.

Roadmaps are NOT the first step in product development.

However, every PM doesn’t have the leverage or freedom early on to challenge the deliverable. I know PMs who have tried arguing with management on this front and sadly, it didn’t end well.

Managers and teams can get impatient as they want clarity for their engineering teams quickly. They’re also conscious of their financial runways.

So, what do you do?

Rather than beating ourselves up, let’s take a crack at it.

I faced a similar challenge at Yallamotor. The CEO/CTO asked me to develop a roadmap complete (with wireframes!) in 4 weeks. I managed to submit a deliverable that served as a guiding light all up till a successful product launch 7 months later. This post summarizes the tactics I applied there.

Also, know that the artifact doesn’t have to be perfect. It just needs to be a “good enough starting point”.

Note: If you want the more traditional way of building a solid roadmap, there are tons of resources already out there. Some examples:

3 Ways to Create 10x Better Roadmaps by Pawel Huryn

How to build a roadmap by Jory MacKay (Plan.io)

Advanced Roadmap Tips & Techniques by Aakash Gupta

Before we kick off with the steps below, a disclaimer:

• The steps below will seem like a LOT for a few weeks. I hate to break it to you but you have your work cut out, so there really is no time to waste. Executing Step 3 is the most time-taking part of this exercise.

• Some of the advice below will seem contrary to conventional wisdom and blasphemous to product purists. The absence of a fleshed-out product strategy, double-diamond ideation, extensive discovery, OKRs, heavy collaboration, design sprints, metrics frameworks, and go-to-market alignment will likely trigger you. Sadly, with little time to create executive alignment and affect product culture, we are forced to improvise.

Exercise this process only when you have to.

It has 8 steps:

1. Pre-reading

2. Set up the sandbox

3. Go on a listening tour

4. Read the market

5. Establish the 5 foundational pillars

6. Inspect your repos

7. Process the sandbox

8. Craft the first draft

To illustrate this process better, I’ll use an example of a restaurant discovery app that helps people discover interesting places to dine out and utilize personalized discount deals and offers.

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Step 1: Pre-reading

As you warm up to embark on this journey, read up on any material the organization has on the problem the product solves.

Some good places to start are:

• a pitch deck

• the marketing website of the product

• vision and mission document (if available)

• townhall slides

• emails sent to employees with strategic direction

• business case documents

• glossary of domain-related terms

Note that you don’t want to jump into reading tasks or customer tickets just yet. The idea here is to familiarize yourself with the target audience, the purpose of the product, and what it’s out to solve.

Before you go on the listening tour in Step 3, you need to be conversant on the high-level concepts, main value proposition, and jargon.

Step 2: Set up the Sandbox

You need a repository where you will consolidate all the customer problems and opportunities in one place and then process them as information comes along.

Open up a Google sheet and add these columns:

• Outcome theme: The high-level outcome the initiative is hoping to achieve.

• Roadmap Item: A brief description of the problem you’re solving or the intended solution.

• Backstory: the rationale or evidence that backs up the need. This can also be direct quotes from your research.

• Linked Metric: the key product, customer, or business metric this roadmap item will affect.

• Source: who or where this roadmap item was sourced from?

• Dependency: which other roadmap item is this dependent on?

• Priority: the priority level you’re suggesting for this item (High, Low, Medium).

• Timeframe: When this roadmap item needs to be addressed: Near-term, Mid-term, Long-run.

Here’s your starting point:

Step 3: Go on a Listening Tour

This is the meat of the process.

You need to download information from the surrounding team on the problem and also create alignment on their worldview.

Below is a short list of people I would schedule 1:1s with:

1. Manager

2. Engineering Lead

3. Design Lead

4. Marketing Lead

5. Sales Lead

6. Customers

7. Customer Success Lead
   

These roles may not exist in your organization or in some cases, one person might be wearing multiple hats. That’s OK. Identify who is available from the list and arrange 1:1 conversations with them.

But setting up the meetings is the easy part.

Knowing what to ask is where you’ll piece together clues you’ll need to populate your roadmap with opportunities and build your foundational pillars (next step).

Here are some question lists for each stakeholder:

Questions for the Manager

Ask your manager (this could be a co-founder, CEO, or another manager) about the vision and if there is a company strategy in place. Don’t worry if there isn’t.

The idea is to extract context from the manager:

Ask questions like:

1. What are the business goals that you see this product contributing towards, both in the short-term and long-term?

2. How do you view the role of this product in solving customer problems or addressing market needs?

3. Why do we think this is a problem worth solving? Will it scale?

4. How are we better than the competition? Why should anyone use us?

5. Who’s the target customer you have in mind?

6. Can you share your vision for how this product fits into the broader company strategy?

7. What are the key performance indicators (KPIs) that you think we should be focusing on?

8. Are there any upcoming business or market changes that could significantly affect our product strategy?

Questions for the Engineering Lead (or CTO)

1. How scalable is our current architecture to support future features or enhancements?

2. What product capabilities are you excited about?

3. What parts of the product are weak and need attention? Why?

4. What opportunities should we be pursuing that are relatively easy to build?

5. What technical debt do you see as the most urgent to address?

6. How aligned do you think the engineering team's efforts are with the current product goals?

Questions for the Design Lead

1. What are your thoughts on the current user experience and what could be improved?

2. What part of the product are you most focused on? Why?

3. How do you see design helping to differentiate our product in the market?

4. How well do you think the current design aligns with user needs and behaviors?

5. What are the key user journeys that you think we need to focus on optimizing?
   

Questions for Marketing Lead

1. What profile of users are you most focused on acquiring?

2. What are the top channels currently driving user acquisition, and what's your strategy for them?

3. What marketing campaigns have been most effective, and which ones didn't meet expectations?

4. Can you identify any customer segments that we're not reaching effectively?

5. What product messaging resonates the most with customers?

6. What do you see as the most compelling need in our target customer base?
   

Questions for Sales Lead

1. What are the key selling points that resonate most with prospects?

2. Are there any consistent objections or hurdles that come up during the sales process?

3. How does our product stack up against competitors in sales conversations?

4. What features or improvements do you believe could help close more deals? What’s helping us close the most today?

5. How do you see the product evolving to meet the needs of different market segments or verticals?
   

Questions for Customers

In some organizations, this part can get tricky.

Problems I’ve faced in the past:

• Some sales managers and C-level execs can be over-protective of customers and might not want you to interface with them this early on.

• There may not be many customers to talk to in the first place.

• Finding a time to talk to these customers may be painful.

• Customers who are ready to talk aren’t representative of your ideal customer profile.

Promise your customer-facing staff that you’ll be a silent listener on a demo call to a prospect (applicable to B2B) or pre-share the questions you want to ask and let them do so on your behalf.

Either way, try your best to get some airtime.

1. What initially prompted you to try our restaurant discovery app?

2. How often do you (experience product problems)? Ex: How often do you plan to dine out?

3. What were you using before? Why wasn’t it good enough?

4. Are there any capabilities you wish the app had?

5. What’s something that didn’t work as expected? Was there anything that frustrated you?

6. When was the last time you used the app? Walk me through that journey.

7. What would it take for you to recommend this to others?
   

Questions for Customer Success Lead

1. What are the most common problems that customers seek help with?

2. How do you currently measure customer satisfaction, and what are the findings?

3. What capabilities or changes could significantly improve customer retention?

4. Are there any warning signs or trends that suggest a customer might churn?

5. Do we have customer stories or use cases that could guide product enhancements?

As you go from one person to another, you’ll likely hear a lot of product opportunities that make sense. At this point, it’s important to keep dumping them into your sandbox sheet to keep track.

Step 4: Read the Market

Next, it’s time to understand the macro outlook of the industry and how competitors stack up against you.

1. Industry Reports
   
   The purpose of an industry report is to educate yourself about the macro trends in the market and buying factors.
   
   Why do people buy?
   What’s the buying process like?
   What notable trends can change the market variables?
   
   The easiest way to search for these is to Google “[product category] reports” and add “.pdf” at the end.
   

2. Competitors

   
   Your leadership and colleagues will probably give you a list of competitors. If you’re in the SaaS market, you can make a trip to G2 to figure out the more prominent choices.

   
   Pick the top 3 and compare messaging, target audience, growth motions (PLG vs. no PLG), and pricing. Also, do a quick feature-by-feature comparison. Ideally, you want to take their product for a spin but if that’s not possible, look for demo videos on their site or Youtube.
   
   If you’re in B2B leading a product with previous churn or lost prospects, ask your sales leader about whom you lose the most business to.
   

3. Dogfooding
   

   Try out your own product. Go beyond the onboarding screens and attempt to traverse the happy flow. Understand what the core strength of your product is.

Based on your findings, add other high-potential opportunities to your Sandbox, especially those that contrast well against your competition’s weaknesses.

Step 5: Establish the Foundational Pillars

The listening tour and market reading serve another vital purpose.

The data you collect educate you enough to erect 5 pillars that you’ll need for processing and prioritizing the sandbox:

1. Vision Statement

2. Fundamental Beliefs

3. Priority Goals

4. Strategic Thesis

5. Outcome Themes

Vision Statement

In many cases, the founders would have already worked on this. The vision statement is the compass that guides your team; it defines the change you aim to make in the status quo and paints a picture of the "promised land."

Example: "A world where consumers dine out not to just eat food but to create unique and memorable experiences.”

Fundamental Beliefs

These are the underlying assumptions or convictions you've gathered across your interviews with team members and customers. They might include market facts, domain expertise, unique advantages, or observable trends.

It's crucial to articulate these beliefs as they serve as your anchor for future product conversations:

Example:

1. Surveys show that post-COVID, there is a 45% surge in demand for dine-out activities.

2. Aggregators send take-out orders to restaurants but don’t contribute to loyalty or brand building. Retention is dismal.

3. Restaurants are willing to heavily subsidize first-time orders as long as customers come into the store at non-peak hours.

4. Dine-in seat consumption is lop-sided. It’s overcrowded on the weekends and less than 30% capacity during weekdays.

5. Restaurant owners don’t just want to highlight their brand but also guide consumers on lesser-known delicacies they ought to try out.

Priority Goals

These are core metrics that the team is actively pursuing as an indicator of success. Your 1:1 conversations should reveal this and if they don’t, explicitly ask your manager.

There are two facets to priority goals:

• Business goal (e.g. revenue, profits, market share, etc.)

• Product goals (e.g. installs, activation rate, MAUs, deals consumed, etc.)

If the organization has a North Star Metric, that can act as the product goal.

Identify the top business and product goal that best aligns with the vision and the single most important outcome the team is hoping to achieve in the short run.

Strategic Thesis

This statement is your short to mid-term game plan.

It identifies a logical script the product will follow to help the team achieve its priority goals.

It states where efforts will be focused, the tradeoffs that will be made (what is not a priority), and the rationale behind why the team thinks this will lead to success.

Note: a strategic thesis is NOT a substitute for a product strategy. It’s a best-effort statement to summarize focus/non-focus areas.

A template that you can customize based on your listening tour:

“We aim to be [product category] for [target customer] in [geographical or market focus] looking for [specific need or use case]. We will know we're making progress if we continue to grow the [key performance indicator] every [time period]. To achieve this, we'll focus on [core strategy or action], such as [broader initiatives]. We think we can win the market because [rationale]. We will not be focusing on [what you are choosing not to focus on or pursue].”

Example:
"We aim to be the go-to restaurant discovery app for people in Toronto looking for a place to dine in with friends and guests. We will know we’re making progress if we continue to grow the unique number of users booking a table at a restaurant through the app. To achieve this, we'll focus on partnering with local restaurants to incentivize adoption by offering onsite experiences and personalized campaigns. We will not be focusing on expanding into other verticals such as food delivery or grocery services."

After you frame your thesis, run it by your manager and some other key stakeholders.

They will probably issue feedback or have a running conversation over it. Massage it to reflect the main concerns but don’t worry if there isn’t universal buy-in.

Outcome Theme

Every priority goal can be achieved by pursuing desirable outcomes that naturally roll up into it.

For example, if you want to increase the number of restaurant tables reserved, outcomes like increasing the choice of restaurants, improving the recommendations piece, and easing the booking flow all align well with it.

If your company is already working with OKRs (Objectives and Key Results), your objectives can serve as your Outcome Themes.

Alternatively, sketch out an opportunity tree from the product goal and break down the problem.

Every roadmap item on the sandbox must be assigned an outcome theme to justify its presence. Pencil that in.

Try to limit outcome themes to 3-4.

Examples:

1. Reduce the time between signup and first deal consumption.

2. Grow base of premium restaurants with advanced levers.

3. Amplify the frequency of referrals and word-of-mouth.

These five pillars will come in handy later on. Keep them safe.

Step 6: Inspect your repos

Inspect the backlog.

If someone was already managing an existing backlog of tasks, peer through them and see if they match the ideas on your sandbox.

If not, then size them up against your strategic thesis to assess how important they are and add them in.

Sidenote: Bugs and defects aren’t roadmap material but it’s best to discuss them with engineering to understand the bandwidth they’ll consume.

Also, identify:

• work items in the existing sprint will bleed over to the next.

• (in B2B) customer customization commitments we’ve already made + their dates.

Analyze Customer tickets.

If the organization has a ticket-based helpdesk, export the list of tickets for the last 3 months.

Manually browse through the tickets to get a sense of them. If you need to fast-track the process, feed them into ChatGPT’s Advanced Data Analysis tool or use a tool like SheetGPT to get summaries for each ticket and assign each row an outcome theme or another category. You’ll need to random sample and check the values to be sure.

Again, look for evidence that corroborates items already on the sandbox sheet OR watch out for recurring themes in the tickets that ought to be listed in the sandbox.

Step 7: Process the Roadmap

The next step is to clean up the Sandbox sheet.

There are a few operators at your disposal here:

• Merge items that have similar outcomes.

• Split items that seem like an amalgam of initiatives.

• Expand item descriptions if they are unclear.

• Cull duplicates that are identical.

• Link dependencies to create sequential order.

• Discard items that seem irrelevant or misaligned.

• Highlight unavoidable customer commitments.

• Bubble up items already planned in the upcoming sprint.

Update the row descriptions and outcomes based on your foundational knowledge, strategic thesis, and lessons from the listening tour.

For example:

• "Implement sharing buttons for deals" and "Add a 'Refer a Friend' CTA on deal checkout pages" could be merged, as both aim to increase referrals and word-of-mouth. The new item could be "Implement sharing and referral features on deal pages."

• "Introduce a first-time user discount" could be dependent on "Streamline the signup process with social logins," making sure that the signup process is smooth before introducing the discount.

Step 8: Craft the First Draft

You have enough data to take a first whiff at your roadmap.

Create three buckets.

1. Near-term (60-90 days)

   This typically has most of your imminent backlog items, key tasks that will overflow to the next sprint, immediate customer commitments, and other items that seem like a priority as per the foundational pillars.
   
   These sound more like fleshed-out features e.g. support “Sign up with Google” as a registration option.

   
   For these in particular, you will have to sit with your engineering lead to discuss the feasibility and effort required to pull these off in the mentioned timeframe.
   

2. Mid-term (next 1-2 quarters)

   These are high-potential opportunities with a few potential options for solutions. (the specificity is a bit lower)
   
   e.g. “Improve the first-time booking flow”, Options: pre-populate the form with defaults, cut down the fields, support instant booking, etc.
   
   The prioritized customer wish lists, issues raised by the manager, and imminent competitive threats are candidates for this bucket.

3. Later (beyond 2 quarters)
   
   These are long-term bets you’re planning to take. These can be general outcomes and can be kept high-level.

   Items that are dependent on short and mid-term executions along with ambitious down-the-road initiatives make their way here.

   
   After you come up with your initial draft, share it with the team. Get generous feedback and iterate where required. However, don’t toss everything around mindlessly. Justify with rationale and use your foundational pillars to support your point of view.

As things start shaping up, you can port the entire table into a Miro template like the one below:

I’m a Notion fan, so I would build something like this:

Again, this is a starting point.

You have to throw in a disclaimer and evolve the document over time.

A quarter into your job, you would have a lot more context. Ensure you keep revisiting the document.

Optional Step

At vFairs, we repurpose our internal roadmap as a customer-facing artifact as well. This has historically helped us close more deals by creating confidence in our strategic direction.

Here’s what a slide in our roadmap deck looks like:

The outcome theme and timeframe are on the top, and the roadmap item title and description are below it along with a preliminary supporting visual.

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Hope this helped.