How to avoid a Frankenstein monster of a strategy
With Chris Jones
Product leadership is often about making tough decisions and setting a clear direction for your teams and organisation. One of the most crucial traits a product leader must develop is strategic confidence. Chris Jones, a seasoned product leader at Silicon Valley Product Group (SVPG), shared with me the importance of being confident in your strategy, especially when the path forward isn’t always obvious.
Chris didn’t always have this level of strategic confidence. Like many product leaders, his leadership journey was accidental. He started as a computer science major and later found himself in product management through a series of pivots. One leadership aha moment is the realisation that good leadership requires strategic conviction.
The Challenge of Strategic Confidence
Product leaders, especially those transitioning from individual contributor roles, often struggle with one key issue: a lack of confidence in their own strategic direction. It’s not uncommon to see leaders trying to gather feedback from every stakeholder, attempting to please everyone by piecing together a strategy that satisfies different departments. This approach leads to what I call a Frankenstein monster of a strategy.”
Real strategy, he argues, is about making difficult choices—often saying “no” to a lot of good ideas in favour of focusing on the most critical opportunities. And this requires confidence in your own judgment.
Chris explained to me how the hardest part of setting strategy isn’t finding the right idea, instead it’s having the confidence to pick one direction and stick with it. This means trusting your instincts as a leader and committing to a course of action, even when others may question it.
While collecting input is important, it is the leader’s responsibility to ultimately make the decision, even if it involves tough trade-offs. A strategy is not just a list of suggestions or a compromise; it’s a deliberate decision about where to focus the organisational effort.
In my product leader coaching experience, I have seen leaders struggling to gain confidence. Without confidence, they often fall into the trap of trying to maintain optionality, pursuing multiple paths at once, which dilutes focus and results in underperformance across the board.
The Danger of Pleasing Everyone
One of the biggest mistakes product leaders make is trying to be people pleasers. Chris has seen this many times throughout his career. Leaders gather input from different teams, stitch together various requests, and try to create a strategy that ticks everyone's boxes. The result? A bloated and disjointed plan that lacks a coherent vision.
A common mistake Chris shared is when "Product leaders see their job as organising all of this and making as many of those people happy as possible. But this really isn't a strategy."
This happens so frequently because many product leaders don't fully trust their own sense of what’s right. Instead of having the confidence to set a firm direction, they seek validation from multiple stakeholders, hoping the collective input will somehow create a clear strategy. But Chris argues that it’s the leader’s job to make the decision, not just compile a list of “people-pleaser” suggestions.
Leadership and Strategy: More Than Just a Plan
Chris emphasises that strategy is not just about having a good plan on paper. It's about leading your team with conviction and guiding them through execution. “It is, surprising how few product leaders really have the confidence to do this or the backbone to do this, or they often really just don't trust their own sense of the situation,” he explains.
Many product leaders fall into the trap of overthinking their strategy, agonising over whether they’ve picked the perfect path. But Chris points out that once you’ve narrowed down your options to a few good ones, the real differentiator is how well you execute your choice, not necessarily which option you pick.
Chris explains, “You've got to focus. And in many cases, it's more important that you choose things to focus on than what you actually choose to focus on… obviously without being reckless.”
The takeaway here is that while the decision matters, leaders should focus more on making a clear and focused decision from a set of good options and less on making sure it’s the "right" decision. Strong execution, Chris says, often matters more than the nuances of one strategy over another.
How to Build Strategic Confidence
Building strategic confidence doesn’t happen overnight. It’s a skill product leaders need to develop over time through experience, reflection, and practice. Chris offers several pieces of advice for product leaders who want to grow their confidence in setting strategy:
Trust your instincts: You have more knowledge than you think. As a product leader, you're in the best position to understand what your product and team need. Trust your experience and insights when setting a course, but don’t ignore the data.
Don’t poll for validation: While it’s important to gather input from stakeholders, don’t confuse input with decision-making. It’s your job as the leader to make the call, even if that means going against the grain of what others want.
Focus on execution: Once you’ve made a strategic decision, shift your attention to execution. Your team's ability to bring the strategy to life and adapt along the way is what will make it successful.
Embrace discomfort: Strategic confidence often means being okay with making people uncomfortable. Not everyone will be happy with your decisions, and that’s a normal part of leadership. Learn to navigate that tension.
Strategic Confidence as a Leadership Skill
Chris’s experience highlights a key distinction between managing and leading. Managers often focus on maintaining the status quo and satisfying various stakeholders. Leaders, however, set a course for the future and guide their teams with conviction.
Strategic confidence is about more than just being able to set a vision—it’s about standing by your decisions, empowering your team to execute, and being willing to adapt when necessary. As Chris shared with me, it’s not about being the perfect strategist. It’s about being decisive and leading with clarity.
Are You Confident in Your Decision Making?
Do you have strategic confidence? Are you trusting your decisions and leading your team with clarity and conviction, or are you getting bogged down by trying to please everyone or be 100% validated?
Leadership is about making hard choices, setting a direction, and guiding your team toward success. Ask yourself: Are you leading your strategy, or is your strategy leading you?