Why Decisions Feel So Hard
Right Nows

By Hannah Baker

Dear Reader,

Over the last few months, I’ve been talking with design and product leaders across very different organizations, large companies, smaller teams, fast-moving environments, and slower ones.

And I keep hearing the same thing.

Their teams are being asked to make decisions faster than ever, and yet, deciding feels heavier than it used to.

Not slower, exactly. Just harder.

At first, people often explain this in familiar ways: too many stakeholders, too much collaboration, not enough clarity.

But when I look across these conversations, it doesn’t sound like a thinking problem.

It sounds like something else.

What changes once a decision is made

In many of these interviews, teams don’t struggle to generate options. They struggle with what happens after a decision lands.

Because once a decision is made, a few things become visible all at once:

• who owns it
• whose judgment it reflects
• what values it signals
• who will be associated with the outcome if it doesn’t work

And in a lot of the organizations I spoke to, those things are unclear.

Authority is distributed.
Criteria shift.
Accountability isn’t always symmetrical.

Several leaders described decision environments with long, branching paths, where many people are involved, but no one is clearly allowed to close the loop. Others talked about decisions that technically get made, but quietly resurface weeks later because they were never fully held.

In those settings, decisions don’t disappear, they circulate.

They get discussed, refined, socialized, and revisited.
They move sideways, upward, or into another meeting.
They turn into alignment sessions, workshops, or “next steps.”

Not because they don’t know what to do.

But because deciding has become a form of exposure.

Why stopping feels so uncomfortable

One thing that came up again and again was how hard it feels to say “stop.”

Stop this discussion.
Park this topic.
Close this line of thinking.

On paper, that sounds procedural. In practice, it’s deeply social.

Several leaders talked about how risky it feels to interrupt momentum, especially in group settings. Ending a discussion means risking being wrong, missing something important, or being seen as the person who shut something down too early.

So conversations continue.
Meetings stretch.
Important tensions stay unresolved.

When the criteria keep moving

This gets even harder when the meaning of “success” isn’t stable.

In multiple interviews, leaders described working toward goals that sounded clear at a high level, “reduce complexity,” “increase resilience,” “move faster”, but were never fully defined.

Teams would start work, only to find that priorities shifted or the goal itself meant something different a few months later.

In those conditions, committing to a decision can start to feel pointless.

Why own a plan if the definition of a win might change?

Why take responsibility when the standard you’ll be judged against isn’t clear yet?

In that context, hesitation isn’t incompetence.It’s self-protection.

This isn’t about confidence

We often talk about decision-making as a personal trait: be decisive, be confident, trust your judgment.

But what I’m seeing in this research is more structural than that. People struggle to decide when they don’t know:

• whether they’re actually allowed to decide
• what will count as a “good” decision later
• whether the decision will hold once it’s made

Passing a decision along or keeping it open can feel safer than owning it.

Not because people are avoiding responsibility, but because responsibility has become heavier and less protected.

Why this is shaping my work right now

This pattern is one of the reasons I’ve been reworking parts of my upcoming Facilitating Workshops course.

Not because I have a clean answer, but because I keep running into the same tension in these conversations and in my own work, teams don’t just struggle with ideas or alignment; they struggle with how discussions actually turn into decisions.

What I’m increasingly interested in exploring is not how to push people toward answers, but how to notice:

• when a discussion is ready to move
• the criteria needed to make a decision
• what kind of decision is actually being asked for
• and how to close something without pretending certainty exists

This isn’t something you solve once. It’s something you practice, together, in real situations (check out the new curriculum now).

The irony is that many organizations say they want faster decisions,
without fully reckoning with how risky deciding has become.

Sometimes the hardest part of deciding isn’t choosing.

It’s being the person who has to live with the choice after the meeting ends.

If you know, you know 😭

Until next month!

Hannah Baker ​Facilitator & Co-Founder ​The Fountain Institute

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