Leadership Advantage - Issue 30

by Andrea Michalek

If your team can’t think strategically without you, that is not a compliment.

It is a warning sign.

This is the essence of what I call The Context Keeper Trap, one of the most common ways capable product leaders unintentionally limit their impact.

On the surface, it looks like leadership: you are in every pivotal meeting, connecting execution to vision, guiding trade-offs, representing the product strategy, keeping priorities aligned.

But here is the reality:

You have not scaled leadership. You have scaled dependency.

Even worse, when strategic thinking is centralized, teams lose connection to customer problems. They optimize for what you want, not what customers need.

Discovery activities risk becoming tactical research rather than strategic exploration.

This is why many teams miss breakthrough insights.

Why The Context Keeper Trap Is So Dangerous

When strategy only happens through you, the organization becomes fragile.

Strategic decisions bottleneck when you are unavailable
Teams execute effectively but don’t develop strategic judgment
Cross-functional partners bypass your team to get input directly from you
Innovation slows because strategic capacity is not distributed

And the weight of it falls squarely on you.

You cannot step away without anxiety, because the system does not function without your presence.

Leadership is not about making the big calls. It is about building people who can make them without you.

When you embrace this, your influence expands far beyond your direct involvement.

Three Breakthrough Shifts to Escape the Trap

Escaping the Context Keeper Trap is not about delegating more tasks.

It’s about transforming how leadership capacity is built across your team.Three Breakthrough Shifts to Escape the Trap

Escaping the Context Keeper Trap is not about delegating more tasks.

It’s about transforming how leadership capacity is built across your team.

1. Scaling Yourself → Multiplication

Move from “only I can do this” to “my team can think and act without me.”

Create frameworks and decision principles that build independent judgment, not just reliable execution.

Example:

Instead of being the only one who can connect features to strategy, codify a simple narrative framework your PMs must use when pitching work:

customer problem → business impact → why now

Soon you’ll hear PMs using the same language in discussions you are not part of.

2. Inspiring Peak Performance → Elevation

Elevate your team from tactical execution to strategic contribution.

Shape an environment where PMs learn to frame problems, weigh trade-offs, and influence direction, not just ship features.

Example:

Instead of being the one who smooths conflicts between Design, Engineering, and GTM, empower your PM to lead the alignment conversations.

The first few may be rough, but over time they will learn to balance perspectives, influence peers, and shape outcomes directly.

3. Talent Magnetism → Succession

Build a reputation for developing strategic leaders, not just managing performers.

Attract and nurture talent that strengthens the bench and reduces organizational dependence on you.

Example:

Instead of presenting in every executive review yourself, create space for your PMs to present their own work.

That visibility signals you are serious about developing leaders.

Within a year, you will see senior PMs trusted with bigger opportunities, some even being recruited into director-level roles, while your organization stops leaning on you as the sole strategic voice.

Career Implications

Many companies unintentionally incentive Context Keeping through performance criteria and performance reviews. As you move up, being “in every room” can look like success.

But this behavior creates a career ceiling.

Context Keepers often stall at the director level because they can’t demonstrate that they develop other leaders.

Escaping the trap takes courage.

Letting go of being needed requires confidence that others can succeed without you.

But the leaders who multiply the impact of their teams accelerate organizational learning, adaptability, and innovation.

They also accelerate their own careers.

The Question Every Leader Should Ask

How many hours last week did you spend on work only you can do?

If the number is consistently high, you are not just busy. You are trapped.

The solution is not to work harder at being strategic. It is to multiply leadership capacity across your team so the organization moves faster, stronger, and more resiliently without requiring your constant presence.

Because the highest compliment is not: “We cannot move forward without you.”

It is: “Your team made the right call, and we are already moving.”

Key Takeaways

✅ Being indispensable feels like leadership. In reality, it creates dependency.

Your presence in every decision may look like value, but it trains your organization to believe strategy only happens through you.

✅ The Context Keeper Trap makes organizations fragile.

When all context flows through one person, decisions slow, innovation stalls, and teams fail to develop strategic judgment.

✅ Leadership is not making the big calls. It is building people who can make them without you.

Your lasting influence comes from multiplying judgment across your team, not hoarding it.

✅ Escaping the trap requires three shifts: Multiplication, Elevation, and Succession.

Codify frameworks, raise expectations, and create visibility for your PMs so they become decision-makers in their own right.

✅ Context keeping creates a career ceiling.

Directors who cannot show they build other leaders rarely advance. Multiplying leadership capacity is what opens the door to the next level.

Ready to Escape the Trap?

On October 1, I’m starting the next Beyond Incremental Inner Circle, a 90-day program for 8 senior product leaders who want to stop carrying the weight of every decision and start leading teams that thrive without them.

In this program, you will: