As a leader working toward complex goals, you likely find yourself giving directions, setting expectations, checking for understanding, and repeating yourself more than you expected. You think you're doing everything right — and yet things don't go according to plan.

Deadlines slip. Quality falters. Your mind naturally goes to insufficiency: "I didn't explain myself clearly enough." Or toward the team: "They're not listening."

In both cases, you assume the fix is the same — you need to talk more.

For chronic under-communicators, that may be true. But many leaders find that the more-talking strategy produces the same conversation, over and over, with unchanged results.

What Would It Look Like to Listen Differently?

The first place to explore is listening for signals that the people you manage are actually in sync — not just telling you what you want to hear.

At Talentism, we delineate three levels of being "in sync" with your people:

  • Awareness — a person hears you and can repeat it back verbatim.
  • Understanding — everyone involved interprets the thing you said the same way.
  • Alignment — people's behavior is consistent with what was discussed.

Typical power dynamics cause people to say "Yes, I understand" even when they feel shaky. Do you have any evidence that both of you are holding the same visualization? If not, you don't have understanding sync — and you can't get to alignment from there.

"It's impossible to discern alignment through conversation alone. You only know if you had alignment through the outcomes."

Design for Reality, Not Perfection

People are not machines. You cannot give instructions and expect uniform outcomes. Under scrutiny, most plans assume everyone at their best — and don't account for what is likely to happen in the real crucible of leaders trying to achieve big things.

Premortem what might happen given what the people involved are actually like. How do they show up when things get hard and confusing? Where will they need help, and where are they well-positioned to help others?

Don't expect perfection. Design for reality.

Adjust the Design Before You Start

After identifying likely pitfalls, adjust the design from the start. Are there places where you're setting people up to fail? Once you've made those adjustments, strategize how people can help each other. And acknowledge that even with the best preparation, there will still be bumps.

Figure out in advance how you will recover quickly. The path to innovation is nonlinear — but with planning that anticipates messiness, you can minimize frustrating detours.

Commit to transparency. Remove shame around struggles. Foster psychological safety so your team can navigate inevitable obstacles rather than hide from them.