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Decision-Making Questions for Entrepreneurs

  • Writer: Karthik Sake
    Karthik Sake
  • 5 days ago
  • 4 min read

Let’s cut the BS - running a startup is a wild ride, like trying to herd cats while the house is on fire. Decisions? They’re the pulse of this chaos, and they hit you hard and fast. Staying chill and objective when your gut’s doing somersaults? Easier said than done. That’s why I lean on questions - raw, no-filter questions - to slice through the mess and keep me grounded.


This is my take on decision-making questions for entrepreneurs - a scrappy, human toolkit forged in the startup trenches. We will look at what questions do you need to ask and answer when: launching something new, hiring your next teammate, scraping by on fumes, deciding to pivot, scaling up, or dodging a crisis. Let’s rip into it.


entrepreneur decision making

Why Decision-Making Questions Are an Entrepreneur's Lifeline


We’re wired to sprint - move fast, break shit, figure it out later. But charging ahead blind? That’s how you face-plant. Questions are your gut check. They make you pause, breathe, and see straight.


Here’s why they’re gold:

  • Bias Slayer: We’re all a little full of ourselves sometimes. Questions call you out.

  • Noise Filter: They ditch the clutter and zoom in on the stakes.

  • Gut Boost: Clear questions, clear calls - no waffling.


This isn’t about slowing down; it’s about not screwing yourself. Whether you’re a lone wolf or wrangling a squad, these questions are your North Star. Let’s hit the scenarios.


Scenario 1: Launching a New Product or Service


You’ve got this killer idea - maybe a slick app or a spicy snack line. Before you unleash it, ask these to keep your head on straight.


Questions to Ask Yourself and Your Team

  • What’s the real itch we’re scratching?If you can’t pin it down, it’s just a shiny distraction.

  • Who’s begging for this? “Everyone” is lazy - think Rohit, the overworked freelancer. Get specific.

  • Why us? What’s your edge? “Cheap” ain’t enough - find your fire.

  • How do we know we didn’t flop? Pick a win - downloads, orders, something concrete.

  • What’s the crash-and-burn risk? If it tanks, can you bounce back? Face it now.


Quick Hack: Jot these on your phone. It’s your launch reality check.


Scenario 2: Hiring Your Next Crew Member


Hiring is key in your journey - nail it, and you’re unstoppable; botch it, and you’re babysitting a mess. These questions keep it real.


Questions to Ask Yourself and Your Team

  • What’s the gap we’re filling? Skills? Bandwidth? Know what’s missing.

  • Can we keep this up? Cash for salary, snacks, all of it - run the numbers.

  • What can’t we budge on? Grit? Tech know-how? Lock in the dealbreakers.

  • How do we set them up right? No one thrives lost - map the first week.

  • What if they suck? Bad fits happen. How do you cut loose?


Real Talk: I once onboarded an intern who ghosted mid-week. Wish I’d asked, “Can they hack our pace?”


Scenario 3: Facing a Cash Flow Crunch


Bank account’s screaming SOS, and panic’s creeping in. These questions pull you back from the edge.


Questions to Ask Yourself and Your Team

  • Where’s the money leaking? Subscriptions? Rent? Hunt the bleed.

  • Can we stall anyone? Beg vendors for 30 days. Most bend.

  • What’s our fast cash grab? Discount drop? Side gig? Scramble smart.

  • Got a safety net? Even 10k can clutch up. Check it.

  • Is this a hiccup or a hellhole? One lean month? Fine. Six? Fix the root.


Example: A friend's shop was struggling. “What can we offload now?” moved stale stock - boom, breathing room.


Scenario 4: Pivot or Push Through?


You’re stuck - traction’s dead, and you’re wondering if it’s time to switch gears. These questions cut the indecision.


Questions to Ask Yourself and Your Team

  • What’s the hard truth here? Churn spiking? Revenue flat? Face the stats.

  • Can we tweak our way out? New angle? Fresh pitch? Test cheap first.

  • What’s your gut screaming? Data rules, but that hunch? It’s not nothing.

  • Can we swing a pivot? Cash, time, sanity - got enough in the tank?

  • What’s the price of standing still? Stagnation might cost more than change.


Trick: Play “it’s dead already” - ask “Why’d it die?” Brutal clarity.


Scenario 5: Scaling the Hustle


You’re buzzing, ready to blow up. Scaling’s a beast - these questions keep it from eating you alive.


Questions to Ask Yourself and Your Team

  • What’s choking us?Stock? People? Spot the bottleneck.

  • Will our bones hold?Site crashes? Orders lost? Test the load.

  • How do we not half-ass it?Bigger shouldn’t mean crappier. Nail quality.

  • What about the OGs?New blood’s dope, but loyalists bankroll you.

  • Can we loosen the reins?Control freaks don’t scale. Trust or bust.


Lesson: Saw a hustle scale sloppy - lost their soul. Grow sharp, not sloppy. Sloppy works when you are figuring it out in the initial stages. Scale comes from clarity.


Bonus Scenario: Surviving a Crisis


Startups love drama - think a viral screw-up or a supplier ghosting. These questions steady the ship.


Questions to Ask Yourself and Your Team

  • What’s the real fire? Don’t mop the floor in a flood - find the pipe.

  • Who’s getting burned? Clients? Crew? Prioritize the fallout.

  • What’s the quick patch? Speed’s king in a crisis. Move now.

  • How do we spin this? Own it or dodge? Pick your voice.

  • What’s the takeaway? Every disaster’s a teacher. Learn fast.


Real Talk: A client's logistics blew up. “What can we fix today?” saved their day.


Making These Your Own


Don’t just skim this - use it. Scribble ‘em in your notebook, grill your team over beers, whatever works. Start a decision log - situation, questions, answers, outcome. It’s like steroids for your founder brain.


Why Questions Beat Answers


Startups aren’t a script - they’re a sweaty, glorious mess. That’s why decision-making questions for entrepreneurs are your edge. They don’t hand you the win; they hand you the fight. In this rollercoaster, that’s power.


Next time you’re staring down a choice, don’t wing it - ask. You’ve got the grit, now wield the tools. Smash it!


Let me know your thoughts and any other questions you ask that give you clarity. Write to me - karthiksake@growthnursery.com

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