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  • Writer's pictureHarshal

Lessons In Coaching For Roadmap, OKRs, And Product Teams

Best Practices From The Trillion Dollar Coach To Lead Or Coach Product Teams

If you want to align your product roadmap with your company strategy, make your team efficient, or know about Product Coaching, read on.

I talked with a prospective client interested in product management coaching. Their product team wanted help to create a roadmap and align it to the company's strategy. I looked up articles and books, noting down best practices to help them succeed.

In this post, I’ll share my learnings about:

  • Product coaching.

  • Learnings from books, including The Trillion Dollar Coach.

  • Creating Product roadmap.

  • Aligning product roadmap with company strategy.

I spent 2 hour 46 minutes writing this post.

Cartoon executive making decisions, visualizing information, and writing things down.
Cartoon executive making decisions, visualizing information, and writing things down.

I originally published this post on on Mar 18, 2024.

Situational Context With Prospective Client

The product team at this company lacked a high-level roadmap. They hadn't defined epics or project milestones clearly. But, they were (thorough) in the weeds in prescribing changes like creating a new button or a database operation.

Confused team plan.
Confused team plan.

The product team seemed open to course correction. They wanted to align their daily tasks and project planning with the company's goals. This would help the engineering and design teams focus on the most important customer problems.

Enter, product coaching.

What is Product Coaching?

I wasn't sure if the situation needed product mentoring or coaching. Was it about career coaching or job coaching? Were we looking to improve the quality or quantity of work performance?

After researching, I learned I should call this “product coaching”.

Coaching is more structured and goal-focused than mentoring. The coach and client set goals and work step-by-step towards them. If a product management team/lead wants to develop planning, prioritization, and stakeholder alignment skills, then I can coach them through feedback and guided practice.

Product Coaching Best Practices

Best practices in coaching include

  • having regular, structured conversations and

  • setting goals, then ensuring accountability.

Uncover blind spots or the ‘known-unknowns’ - as visualized in the Johari Window. Gather peer feedback to see different perspectives on the individual. Keep this feedback anonymous or anonymize it before sharing it with the client. Visual by Simon Shek on Wikipedia, Public Domain

Johari window showing blind spot.
Johari window showing blind spot.

Feedback needs to come from all important people in a product manager's circle:

  • Their engineering and design team who work with them day-to-day,

  • Their direct PM peers,

  • Their sales, support, and marketing peers, and 

  • Engineering, product, and design leadership.

When giving feedback, do not meddle. Avoid solving their problems for them or making decisions on their behalf. Doing so can make them seem less capable in the eyes of others,

I've also learned about coaches observing their clients in meetings from Bill Campbell, Charles Duhigg, and Marshall Goldsmith. Here are 3 tenets I learned about shadowing a coaching client:

  • Take notes but don't interrupt. Discuss your notes in a separate 1-1 meeting.

  • Shadow only in a few meetings, not all. Find a mix of meeting types.

  • Set a clear timeframe for observing via shadowing.

Source: Brandon Chu

Kick Start Coaching With A Client

Start with building a relationship with your client. Understand them through open-ended questions, focusing on their goals and challenges. Then, propose a path you can take together.

Your client can use a self-assessment to agree with setting the behavior-change goals.

You could start with a one-time session. This initial meeting is like a ‘pilot’ - it requires no ongoing commitment.

Throughout this process, you will have many crucial conversations. Use empathy, listening, and respect. Ask probing questions to encourage self-discovery. Keep the conversations confidential.

Lessons From Bill Campbell

Bill Campbell at TechCrunch Disrupt.
Bill Campbell at TechCrunch Disrupt.

Bill Campbell, the subject of the book “Trillion Dollar Coach” was a very influential executive coach in Silicon Valley. Image from New Yorker. Bill had 3 Pointers on Building a Team:

  • Reliability: Team members must count on each other reliably.

  • Meaningful Roles: Ensure every team member feels valued and crucial to the team, no matter their role.

  • Clear and Meaningful Goals: Make sure each team member knows the goal, understands its importance, and feels inspired by what you aim to achieve.

Bill’s 4 pointers on decision-making:

  • Last to speak

  • All aboard required. Get commitment.

  • Not overanalyze. Opportunity cost. Never have all the data.

  • Have a Process for decision to give confidence in decision.

But, even the best coaches cannot succeed everywhere. Only Coach the Coachable. How do you identify someone coachable? Focus on prospective clients who show

  • honesty, 

  • humility, 

  • willingness to work hard, and 

  • a constant desire to learn.

Prioritize teaching skills to improve team communication and resolving disagreements. For example, start every meeting with relationship-building. Co-create agenda of 1-1 manager-report meetings by writing 5 words on a whiteboard independently and reveal it together.

Bill said:

“Work the Team, Then the Problem”

Give feedback. Be relentlessly honest and candid in giving feedback. But also combine negative feedback with care. Don’t tell people what to do. Offer stories and help guide them to the best decisions for them

Coaching Reads

Instead of writing a garbled high-level summary of multiple books, I’ll link to book summaries.

Do you have any other book or course recommendations?

Roadmap Creation Best Practices

I had the chance to apply the below learnings when I developed a roadmap tool to align a team of 5 product managers at a B2B SaaS company. I discovered how each PM wanted to update their roadmap based on their use of my tool and their feature requests. I experimented with various roadmapping or planning approaches. Visual below from Roadmunk.

Roadmap example showing deliverable timelines.
Roadmap example showing deliverable timelines.

Two Goals for a Roadmap:

  • Show leadership that we are focusing on the biggest business goals.

  • Set deadlines or time commitments.

Ideally, explain the problem you want to solve, not the feature you want to build. This approach is similar to the concept of 'commander's intent'. Use OKRs, for example, "reduce time for customers to onboard" Objective with a Key Result of "reduce time to 3 days".

Each team, like engineering, design, and product, needs to align on one common roadmap. But, each can have internal roadmaps for sub-tasks.

Or, maybe you have tried roadmapping and you find yourself spinning many cycles in planning. Then, use the now, next, later approach to roadmapping. This enables product teams to focus on discovery of customer needs, not estimations. Image from ProdPad.

Now, next, later style of roadmap.
Now, next, later style of roadmap.

There is more information out there about B2C product management, but avoid applying B2C techniques to B2B because:

  • B2B buyers need long-term reliability and confidence in your product vision.

  • The user and decision maker are different in B2B contexts.

For B2B products, take a two-pronged approach:

  1. articulate a long-term product vision, but 

  2. establish a culture of flexibility when it comes to the details.

Communicate that your roadmap is directional, guiding the team while allowing for adjustments as needed.

Aligning Roadmap With Strategy

You want to make your product successful. Why? Because you believe its success will make your business successful. Aligning the product roadmap with strategy or OKRs is crucial for the success of your business. Your approach to planning will vary depending on:

  • Whether you are finding product-market fit (pre-PMF),

  • You are post-PMF, or

  • When managing a portfolio of products.

Ramp (Geoff) approach to product planning at different company stages.
Ramp (Geoff) approach to product planning at different company stages.

For a portfolio of products:

  • the planning is bi-annual, 

  • with priorities set quarterly, and

  • execution is done monthly.

  • Dreams or long-term visions are revisited annually.

In contrast, for a product that's pre-PMF:

  • planning happens monthly, 

  • with execution and prioritization occurring bi-weekly, and 

  • dreaming is done quarterly.

OKRs Best practices

Start with the S-word: strategy. Ask this question to set the foundation:

"What are we here to achieve?"

Often, teams get overwhelmed by the process of setting OKRs. This is because they feel they are fitting a square peg into a round hole. You know your goals, but forcing them into the OKR framework can be challenging, causing undue stress over wording and metrics.

Keep OKRs to a minimum count. Most companies end up writing more than they should, which overcomplicates their decisions.

Allow for flexibility in how to achieve these goals. Metrics should be measurable, ideally daily. Have a dashboard for tracking progress on every metric.

But, don’t solve for the metrics. To avoid side-effects of overemphasis on OKRs, do this:

  • Overall KPIs: Don’t focus on metrics at the expense of the overall business health. Include KPIs that reflect the broader health of the business to maintain balance.

  • Common goals: Encourage cross-functional collaboration to avoid working in silos. This helps teams work together towards common goals rather than solving for their metrics.

  • Individuals: Don’t use OKRs to evaluate individual performance. They are meant to motivate, align, and enhance transparency across the organization. Not a carrot-and-stick approach to performance for any individual.

You will find increasing motivation and engagement if 60% of your OKRs are defined by the employees themselves.


I felt energized to discuss product coaching with the prospect after reviewing the above info. I also identified gaps in my appetite to do vs coach. I had followed the “I do, we do, you do” approach to coaching in previous consulting projects, but now I had to directly skip to the “you do” step.

Ending Thoughts

Effective coaching transcends the mere transfer of knowledge. It is about empowering individuals and teams.

Success lies in aligning our teams' efforts with broader company goals, grounded in a culture of continuous learning and feedback. 

What have you seen work well to build product roadmaps, align roadmap to OKRs, or coach product management skills?

I originally published this post on on Mar 18, 2024.



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