How do you get the exec team on board with your product strategy?

For us, product strategy stems from company strategy, so it's first important to have a firm grasp on where the company strategy is headed holistacally, and why. Additionally, we serve as a partner function for the entire ProdDev org, so rather than owning a specific segment of the product, we're responsible for helping the company zoom out a bit to identify key areas that could make sense to invest in. 

As a result, when working with our exec team it's critical to understand both the company strategy & priorities, functional strategy & priorities, as well as the audience we're communicating with. Similar to working with customers, no conversation is one size fits all. It's critical to understand how to communicate at the right altitude, align your recommendations to existing priorities, and understand how to listen / iterate on feedback to achieve the best outcomes. 

Some specific advice for influencing leadership, whether at the executive or other levels would be:

1. Clearly define how your suggestions accelerate the achievement of goals you know they care about
2. Proactively provide the appropriate framework / structure to assist their analysis of your recommendations
3. Invite / proactively think through the devil's advocate perspective to your recommendations
4. Possibly most important of all, be clear about what you're asking them to contribute to / decide on

I encourage my teams to start by understanding their objectives, plans, assumptions & approach to risk management. We listen carefully and figure out where the gaps and opportunities lie and how impact & success is defined & measured. 

Then, as we develop our strategies, we share early & often – at minimum at the key stages of defining what our product strategy might become:

• Defining the customer problem & the opportunity size
• Proposing the right solution & the necessary investment
• Defining the go-to-market plan
• Adjusting & iterating post-launch at our Mike Tyson Moment ("everyone has a plan until they get punched in the mouth")

This question is intriguing. Let's begin by examining instances where product strategy discussions didn't go as planned, both in my own experience and those of others. I've participated in numerous product strategy meetings—some ending successfully and others spiraling into chaos. Let's delve into the common themes that contributed to these outcomes before we explore a recommended approach.

Instances of Chaos: It's tempting to assume that a disastrous outcome signifies a completely misguided strategy, but surprisingly, that's not always the case, at least from what I've observed. More often, fellow Product Managers faced these stumbling blocks:

1. Misaligned Company Strategy: Trying to align a product strategy with a company strategy that is changing or hasn't been fully communicated or embraced can lead to friction. Waiting for a clear company strategy pivot and then aligning your product strategy can prevent this hurdle.

2. Executive Distrust in Data: Lack of trust in data or its rigorous exploration can stymie progress. To mitigate this, consider presenting data familiar to the executive team, making it a logical extension of their existing insights. Alternatively, when presenting novel data, adopt a researcher's approach—offer multiple data sources, sample sizes, effect sizes, consistency over time, and variation analysis to bolster credibility.

3. Ignoring Pain Points: Addressing painful but inconvenient truths is essential. Skirting these issues in your strategy may make it seem like you're disregarding glaring problems in the product today. Acknowledge these challenges, confidently explain why they aren't immediately solvable (or let the team know they are currently being worked on and provide and update), and offer insights into potential solutions.

4. Vague Strategy: Ambiguity or loftiness in your strategy's wording can lead to misunderstandings. Utilize tangible examples, both verbally and visually, to concretely illustrate how your product will evolve. A compelling visual explanation can defuse semantic disagreements.

5. Lack of Validation: Presenting an unvalidated strategy can backfire. Engage with cross-functional partners before the executive meeting to gauge reactions, address potential gaps, and gather insights for a refined message.

To sidestep these pitfalls and secure support for your product strategy, consider these strategies:

1. Craft an Engaging Story: Develop a narrative that vividly communicates your strategic vision, supported by market insights and customer needs.

2. Rely on Trusted Data: Back your strategy with dependable data or explain your methodological approach to enhance credibility.

3. Align with Business Goals: Connect your product strategy with overarching business objectives and metrics to showcase its value.

4. Involve Cross-Functional Partners: Share your strategy with key partners ahead of time to refine your message and anticipate questions.

5. Foster Open Dialogue: Encourage feedback and create a platform for open discussions during presentations.

6. Add Specifics and Visuals: Provide concrete examples and visuals to breathe life into your strategy, making it more relatable and compelling.

7. Confront Challenges Directly: Tackle problematic topics head-on, offering feasible solutions or explaining why they're currently unaddressed.

8. Infuse Passion: Your belief in the strategy can be contagious; a lack of conviction might be equally evident.

Step one (Do not skip this step!): Make sure you understand the company (or division) strategy that your leadership team is accountable for. If it's vague, push for clarity and see if they will provide it. If not, then let them know the product strategy will cascade from their vision/strategy, and there is risk because of the lack of clarity. Help them see how their vision impacts your strategy; how you are trying to help them win.

Step two: Anchor execs on the needs of the customer (JTBD) before you share the strategy. Help them understand what customers want; what will cause them to pay. Use quotes, data, interview clips etc.

So far, note that your goal is to get clarity on what the company wants (vision) and what the customer wants (JTBD) before you say how you plan to get there.

Step three: Source ideas from the executives and other stakeholders before you craft the strategy. This creates early buy-in.

Step four: In an artifact (deck or doc) list all the bets you could place to meet the customer needs in a way to accomplish the vision (or other bets you might need to make to get there that might not have to do with the customer, like paying down tech debt, etc.).

Step five: Propose which bets you think you will close the gap from where you are today to arriving at the vision. Be clear about the bets you don't think should be placed. Call out the hypothesized outcome for each bet.

Ask for feedback and debate!

The first and major step for any initiative would be to clearly understand the company's goals and priorities - and ensuring that your product vision and objectives closely align with these. If this can be achieved, the job is half done. But rarely do we come across such clear synergies and hence we work on an evolving plan - typically a clearly articulated roadmap - with milestones

Here having a short term view (<90 days) - Items that deliver immediate value: Its easier to convince the executive team if we are able to generate tangible / measurable results in the short run.

Building the trust - we move towards strategic initiatives that typically involve committed medium to longer term investments. These are critical to the success of the product overall, but dont deliver value either immediately or have several dependencies / complex tasks that require larger investments. For this:

• Running a pilot (within the short term delivers) to clearly demonstrate broader value where possible would be an easy win

• For the tougher / longer asks, engaging the key stakeholders very early in the cycle, gathering their inputs and address any concerns - By getting them invested in the idea, everyone collectively works towards making the initiatives successful.

• Clear articulation, especially showcasing benefits from the overall company's positioning in the market would greatly help the cause