Prioritization techniques for founders: 10 Questions every founder should ask themselves

Drowning in to-dos? You're not alone.

Tell me if this sounds familiar: Your to-do list is overflowing. Ideas, admin, content, client work, marketing… it never ends.

As a founder or freelancer, you’re not short of things to do. You’re short of clarity on what’s actually worth doing (or at least, worth doing first).

That’s where these 10 prioritization questions come in. These are prioritization techniques I use regularly with my clients, to help them focus on what matters, and park what doesn’t.

They’ll help you step out of overwhelm and into CEO mode so you’re making decisions based on strategy (not just feelings).

Asking questions as a prioritization technique

Traditional to-do lists don’t discriminate. They treat updating your website footer with the same urgency as pitching a $100k project.

And yes, while I accept that you’re probably not treating updating your website footer with the same urgency as a $100k pitch, you are probably stuck between a bunch of choices that feel important.

Powerful questions force you to think differently. They help you cut through noise and complexity, and recognize the stuff on your list that will actually help you scale.

10 Questions to help you prioritize what matters

1. Which tasks directly generate revenue or growth opportunities?

This should be your first filter.

If a task helps you:

• Land new work

• Retain a high-value client

• Raise your visibility

• Create recurring income

…it deserves attention.

For example, spending an hour sending three targeted proposals is more valuable than tweaking your branding colours, for the fifth time.

Think income first, polish second.

2. If I could only accomplish three things this week, which would have the biggest impact?

This question forces simplicity. It’s a tweaked version of Warren Buffett’s “2 List” strategy. List everything, then circle the three most important things.

The rest? Avoid until the top three are done.

Let’s say your list includes:

• Writing LinkedIn posts

• Creating a new lead magnet

• Replying to 20 unread emails

• Preparing a pitch for a dream client

Which ones actually help you move towards your goals? Prioritize those.

3. Which of these tasks, if completed, would make others easier or irrelevant?

This comes from The ONE Thing by Gary Keller. Look for keystone tasks, things that unblock or eliminate other tasks.

Example: Instead of manually invoicing clients every week, you set up automated invoicing. That single change saves hours each month.

Automation, delegation, and high-leverage decisions belong at the top of your list.

4. What am I doing out of obligation rather than strategic importance?

Some tasks stay on our list because we feel guilty not doing them, like responding to every DM, or attending networking events we dread.

Ask yourself:

• Is this moving my business forward?

• Would I choose to do this if I weren’t trying to please someone else?

If you really want to get your time (and probably a bit of sanity) back, dump these tasks.

5. What’s causing the most anxiety or friction right now?

It’s often the task you’re avoiding that’s draining your mental energy. Chasing an unpaid invoice. Having a tricky conversation with a client. Fixing a broken system.

These aren't always big jobs (they’re usually pretty small), but they carry emotional weight.

If something’s living rent-free in your head, deal with it first.

6. Which tasks keep getting pushed back, and why?

Consistently delaying a task is data. It might be:

• Too big (break it into parts)

• Too vague (define the outcome)

• Not that important (drop it entirely)

Example: You keep rescheduling “update my website.” Maybe it’s not urgent. Or maybe it needs clearer next steps, like: “Rewrite my services page copy.”

Avoiding something repeatedly? Ask yourself why.

7. What’s the highest-value task I’m avoiding, and what’s behind the resistance?

Sorry, this one is probably going to sting a little…

Often, the work that matters most (like raising your rates, asking for referrals, or launching a new offer) also brings discomfort.

You tell yourself you're too busy, but deep down, you’re worried about it going wrong.

Ask:

• What am I worried might happen if I do this?

• What’s the cost of not doing it?

I know it’s a cliché, but honestly, growth comes when you start doing the uncomfortable things.

(Note: If raising your rates is on the cards, check out my pricing calculator)

8. If I stopped doing this task completely, would it even matter?

Not every task deserves space on your list. Some activities are merely nice-to-haves. Things you've convinced yourself you should do, but which rarely create meaningful outcomes.

Ask yourself honestly:

• Would anyone notice if this didn't get done?

• Will it genuinely impact my business 30 days from now?

This one feels a bit basic without an example, so here you go:

Regularly posting to a social media platform that never brings clients or meaningful engagement.

You might feel pressure to maintain a presence on every platform, but if a particular one never results in leads or meaningful conversations, dropping it entirely could free up some time without affecting your business.

9. What could someone else do just as well… or better?

Delegation doesn’t have to mean letting go of everything, or even big stuff. You can probably win back a ton of time just by outsourcing simple tasks that add up (check out this post for 5 tips to improve your outsourcing!)

You don’t need to:

• Schedule your own calls

• Format your own blog posts

• Design your own social tiles

  
  

If someone else can do it 80% as well, hand it off.

This frees you up for higher value work; strategy, sales, delivery.

Also, consider opportunity cost. If you're earning $200/hour on strategic work, paying a VA $25/hour to handle simpler tasks is an easy win.

10. If you had to ditch half your list right now, which tasks would be the first to go?

This exercise pushes you to distinguish clearly between what's essential and what's merely filling your time.

Try it now:

• Take your full list.

• Cross off the least impactful half.

• Now ask yourself honestly: "Would removing these actually hold my business back?"

Remember, most founders don’t need extra hours, they need fewer distractions.

Use these questions as a weekly habit

Don’t just save this post for a stressful day (and never read it again). Set a recurring 10-minute slot at the start of your week to review your to-do list with these filters in mind.

Over time, you’ll get faster at recognizing wasteful tasks, and more decisive. You’ll stop overcommitting. You’ll work on fewer things, but they’ll have more impact.

And yes, some of these questions might feel similar or overlap for you, if so, take what works, leave what doesn’t.

Final thoughts: Act like a CEO

Being busy isn’t the goal. Being deliberate is.

These questions are about thinking like a business owner, not just reacting like an early stage freelancer. They help you stay focused on work that creates income, space, opportunity, and momentum.

Need help prioritizing the things that matter?

If your list feels never-ending and you can’t tell what’s urgent, what’s important, or what can wait, I can help.

I work with founders and freelancers to:

• Cut through overwhelm

• Build clearer systems for decision-making

• Focus on strategic growth, not just survival

Let’s talk about how to focus your energy where it actually counts. Check out my process and pricing page for more info, or contact me to book a free discovery call.