Strategic Retreat Intake — AssetCool Leadership Retreat

Who's submitting this

So the facilitator can read your answers in context. Names are never quoted to the group without your explicit consent.

Your name*

Please add your name.

Your role at AssetCool*

Please add your role.

The company, in your words

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Q1In one sentence, what does this company do?*

We compare answers across the team. Divergence here is data — it's almost always where the retreat opens.

A one-sentence answer here helps anchor everything else.

Q2What are we genuinely great at right now?*

Please share at least one strength.

Q3 What are we pretending is fine that isn't?* Confidential

Only the facilitator reads this. No attributed quotes shared without consent.

This one matters most when it's specific.

Q4Where do you honestly think we'll be in 18 months?*

A short, honest forecast is fine — even one or two sentences.

This leadership team

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Q5What's working well on this team right now?*

Please name at least one thing that's working.

Q6Where does this team consistently get stuck?*

Concrete examples are more useful than abstractions.

Q7 What's the conversation this team keeps avoiding?* Confidential

If the room had two extra hours of honesty, what would surface?

Even a working guess is useful.

Q8Whose role or perspective do you wish you understood better?*

Naming the role (or person) helps us design pair exercises.

Q9 Is there a tension on this team you'd like to see addressed?* Confidential

Be specific — names are fine and stay with the facilitator. Write "none" if there genuinely isn't one.

Please share what's there, even if it's "none".

Strategy & priorities

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Q10What's the single most important decision we need to make in the next six months?*

One decision, named as clearly as you can.

Q11What are we spending time, money, or attention on that we should stop?*

If nothing comes to mind, write "nothing" — that's signal too.

Q12What are we not investing enough in?*

Could be people, tools, time, or attention.

Q13If you were CEO for a day with no consequences, what would you change?*

Have fun with this — the wilder answers often have a real one underneath.

Q14How aligned do you think this team actually is on strategy?*

Pick a number 1–10, then say why.

Score: 1 = nobody agrees · 10 = locked in

Pick a number 1–10 and add at least a brief reason.

You

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Q15What do you want to walk away from this retreat with?*

A concrete take-home (a decision, a clarity, a relationship reset) is more useful than a vibe.

Q16What would make this retreat a waste of your time?*

Saying this in advance is how we avoid it.

Q17 What's something about how you're feeling about work right now that the team doesn't know?* Confidential

Whatever shape it takes — energised, drained, hopeful, on the fence — name it.

Q18 Where do you need support that you're not getting?* Confidential

Be as concrete as you can about who, what, when.

The one thing

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Q19 What's the one thing you hope we discuss — but are worried we won't?* Confidential

This question almost always points at the same thing Q7 does. That's the conversation we engineer for you.

Please name it — even if it's just a working description.

Q20Anything else you want the facilitator to know before we design these two days?

Optional. Context, history, sensitivities, dynamics — anything you'd want me to know walking in.

0 of 19 required answers complete

Thank you — that went straight to me.

I'll read every answer before the retreat. If anything I share back in the room looks like it might identify you, I'll check with you first.

If you remembered something else after submitting, just email me at danny@sidequeststrategies.com.

— Danny · your retreat facilitator