Hey :)

Most teams don't struggle to come up with ideas. They struggle to say no to them.

There's always another project worth doing. Another initiative that sounds smart, feels urgent, and has at least one passionate advocate in the room. The problem isn't identifying good work — it's figuring out which good work is actually the right work, right now.

Over time, I've found that the best filter isn't a framework or a scoring matrix. It's a set of honest questions. The kind that cut through enthusiasm and get to what's actually true about a project before you commit to it.

Here they are.

Start with the problem

Before you even think about the project itself, get clear on what you're actually trying to solve.

What is the single biggest issue in the business right now?
Does this project directly and materially reduce that issue?
Will it reduce it in the next 6–12 weeks?

These three questions do a lot of heavy lifting. If you can't draw a straight line from the project to your biggest current problem — and do it quickly — that's worth pausing on.

Ask what happens if you don't do it

This one is underused. Most people pitch projects by explaining the upside. Fewer ask seriously about the downside of not doing it.

If we don't do this, what actually happens?
Could this wait?
If we solved the main constraint first, would this become easier or unnecessary?

Sometimes the honest answer is: nothing much happens, it could absolutely wait, and tackling something else first would make this project half as hard. That's a signal.

Check your motives

This is the uncomfortable section — and probably the most useful one.

Is this something the business needs, or something I quite fancy doing?
If it were boring, would we still do it?
Are we trying to convince ourselves (or someone else) that this is necessary?

The last question is the one that stings a little. If you find yourself building a case for a project rather than simply recognising it as obvious, that's worth noticing. Good work usually doesn't need that much selling.

Look at what you're already carrying

New projects rarely start on a blank canvas. There's almost always unfinished business in the background.

Have we finished the last meaningful project we started?
Do we have open loops that need closing before starting something new?

Starting something new when something else is still half-done is a tax on your focus and your credibility. Close the loops.

Be honest about capacity

The most common mistake in project planning isn't bad strategy — it's optimistic maths.

How long will this take? (Now double it.)
Do we genuinely have the time?
After committing to this, do we still have at least 20% slack for fires and unexpected problems?
Are we underestimating the energy cost?

That 20% slack question is one I keep coming back to. If saying yes to a project fills your calendar to 100%, you're not planning — you're hoping. And something, somewhere, will break.

Be clear about what you're trading

Every yes is a no to something else. That sounds obvious, but most people don't make it explicit.

What are we saying no to by saying yes?
What will suffer if we take this on?

Name those things out loud. If you're comfortable with the trade-off, great — proceed. If naming them out loud makes you wince, that's your answer.

Think about ownership and delegation

Finally, a few questions about who actually needs to do this — and whether it has to be you.

Is this something only I can do?
Could 80–100% of this be delegated within 45 days?
If we said no to this for now, what would that free us up to focus on instead?

That last question is a good one to sit with. Sometimes the most valuable thing a project decision reveals isn't whether to do the project — it's what you'd actually prioritise if you cleared the decks.

There's no scoring system here. No weighted rubric. Just twenty questions worth answering honestly before you commit.

If you get to the end and still feel confident, go for it. But if a handful of these made you squirm a little — that's probably the most useful thing a list of questions can do.

🗣️ 👀

Chris.

/letter