Chiefs of Staff: Is Your Leadership Team Solving the Wrong Problem?

Your leadership team has been talking about the same issue for months.

🤓 Someone suggests bringing in a consultant.

📊 Someone else wants more data.

👥 Maybe the org structure needs to change.

🤝 Maybe you need a task force.

📈 Maybe the team just needs one more analysis before it can make a decision.

As Chief of Staff, this is a good moment to ask a different question:

Do we actually need more information… or are we struggling to agree about what to do with the information we already have?

I wrote recently about the difference between an information problem and an alignment problem. It’s an important distinction for any organization, but I think it’s particularly useful for Chiefs of Staff.

Why? Because you’re often sitting in exactly the right seat to see the difference.

The Chief of Staff sees the pattern

A Chief of Staff occupies an unusual vantage point.

You hear what the executive thinks the problem is. Then you sit in the leadership team meeting where it gets discussed. Plus you hear what individual leaders say afterward. And you see the decks, analyses, Slack threads, emails, and meeting notes.

So often, you notice something nobody else quite does:

We’ve talked about this six times, and we aren’t actually missing much information. We’re stuck somewhere else.

Maybe Finance and Operations have fundamentally different definitions of acceptable risk.

Maybe two leaders agree on the goal but disagree about who should own it.

Maybe everyone knows a tradeoff has to be made, but nobody wants to be the person who makes it.

Maybe the CEO believes a decision has been delegated, while the team is still waiting for the CEO to decide.

Maybe people are debating the merits of Option A and Option B when the real disagreement is about something nobody has said out loud.

That’s not necessarily an information problem. It’s an alignment problem.

And recognizing that distinction is a valuable Chief of Staff skill.

Watch for the symptoms

Here are some clues that your leadership team may be trying to solve an alignment problem with more information:

• The same issue keeps returning to the agenda.
• Each new analysis produces more discussion but not a decision.
• People ask for increasingly specific data that doesn’t seem likely to change their position.
• Leaders agree in the room but interpret the agreement differently afterward.
• Someone keeps saying, “We just need clarity,” but nobody can articulate what information is actually missing.
• People debate solutions without agreeing on the criteria they’ll use to choose among them.
• The team isn’t clear about who has the final decision.

Or perhaps the most telling sign:

Everyone can explain the problem. Nobody can explain what it will take to resolve it.

When you see those patterns, Chiefs, you’ve gotta resist the temptation to immediately produce another slide deck.

Ask: What decision are we actually trying to make?

As Chiefs of Staff, we are frequently asked to bring clarity to messy situations. One of the most useful ways to do that is to turn a broad “issue” into an explicit decision.

Instead of:

“We need to talk about our organizational structure.”

Try:

“Are we deciding whether to move this function under a different executive?”

Instead of:

“We need to align on the strategy.”

Try:

“Which three priorities are we willing to fund this year—and which initiatives are we explicitly choosing not to fund?”

Instead of:

“We need to resolve the tension between these teams.”

Try:

“Who has decision authority when these two functions disagree about X?”

That’s a very different conversation.

Once you’ve defined the decision, you can ask:

1. What do we know?
2. What do we genuinely still need to know before we can responsibly decide?
3. What do we already know but disagree about?

That third question is often where the real work begins. 🙂

Don’t confuse disagreement with dysfunction

This matters especially for Chiefs of Staff because you’re often expected to “get everyone aligned.”

But alignment doesn’t mean everyone thinks the same thing. In a healthy leadership team, reasonable people should disagree.

The CFO, CHRO, COO, CMO, General Counsel, and business leaders are responsible for seeing different risks and opportunities. That’s part of why they’re at the table.

Two executives can look at exactly the same facts and reach different conclusions because they’re optimizing for different things.

Your job isn’t necessarily to eliminate that disagreement. It’s to help the organization use it productively.

• What does each person care about?
• Which assumptions are different?
• What tradeoffs are underneath their positions?
• What would have to be true for someone to change their mind?
• Which concerns need to be resolved… and which simply need to be acknowledged before someone makes the call?

And critically:

Who actually gets to decide?

Sometimes “lack of alignment” is really lack of clarity about decision rights.

Be careful about solving around the conflict

Chiefs of Staff are excellent problem solvers. That’s an asset, but it can also create a trap.

When the leadership team is stuck, you may be able to create a new process, reorganize the work, build a decision framework, establish a committee, gather more data, hire outside expertise, or construct the world’s most impressive 47-slide deck.

And hey, sometimes you should.

But before you start sketching ideas on the whiteboard, maybe first ask yourself:

Am I helping solve the disagreement—or helping everyone avoid having it?

There’s a difference.

Because the best operational solution in the world won’t fix a disagreement about priorities.

A new governance structure won’t help if leaders don’t trust each other.

A RACI won’t resolve a fundamental disagreement about who should have authority.

And a consultant’s recommendation won’t make the tradeoff disappear.

Sometimes the highest-value thing a Chief of Staff can do is recognize when the organization needs to stop solving around the conversation and actually have it.

Know when not to facilitate it yourself

There’s another judgment call here.

Chiefs of Staff facilitate all the time. You can often structure the conversation, clarify the decision, surface perspectives, and help the team reach a conclusion.

But sometimes you shouldn’t be the facilitator. Think twice when:

• You’re pretty sure you’ll be perceived as representing the CEO’s position.
• You have your own stake in the outcome.
• The conflict has become personal.
• There’s significant history or damaged trust among the team.
• The power dynamics in the room may make it difficult for people to speak candidly.
• Or the issue is consequential enough that you need to participate fully as Chief of Staff rather than manage the process.

That’s when neutral outside facilitation can be particularly valuable.

The goal isn’t to outsource the decision. It’s to create a process in which the people who own the decision can actually make it.

Keep a decision and commitment log

Once the team begins making progress, don’t rely on everyone’s memory of what happened.

Keep a decision and commitment log.

For significant issues, capture:

1. Decisions: What did we actually decide?
2. Open Issues: What remains unresolved?
3. Information Needed: What do we genuinely need to learn before making the next decision?
4. Owners: Who is responsible for the next action?
5. Timing: By when?
6. Revisit: When, if ever, will this decision come back to the group?

This is more than good meeting hygiene. Over time, the log can reveal patterns.

Which decisions keep reopening? Where does ownership remain fuzzy? Where does the team repeatedly ask for more information?

And most of all… Which issues consistently get deferred?

Those patterns tell you something about how the leadership team operates.

The Chief of Staff as organizational diagnostician

Some of the highest-value Chief of Staff work happens before anyone decides what the solution should be.

It’s noticing when:

• We don’t need another meeting. We need a decision.
• We don’t need another deck. We need to name the tradeoff.
• We don’t need more consensus. We need clarity about who decides.
• We don’t need another reorganization. We need to address the conflict underneath the structure.
• We don’t necessarily need more information. We need to figure out what we’re going to do with the information we already have.

That’s not administrative work. That’s organizational diagnosis.

And the better a Chief of Staff gets at diagnosing the kind of problem the organization actually has, the less time, money, and energy the leadership team will spend solving the wrong problems.