Startup therapy: More questions to force you to face reality

(Editor’s note: Jason Cohen is an angel investor and the founder of Smart Bear Software. This story originally appeared on his blog.)

Welcome back. Make yourself comfortable on the couch…

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Last week, you’ll recall, we looked at ways to help you discover what was true for you and your business – as well as what you need to do now to seek profits and growth. We’ll continue that line of questioning today – and we promise not to ask a single question about your relationship with your mother.

If you were forced to hire someone today, how would you define her job such that she would contribute enough revenue to cover her expense?
I know, you can’t afford anyone right now, no one can do as good a job as you, and you don’t even know that you’ll ever hire someone. That’s OK, that’s not the point of this question. This gets you to ferret out what tasks are being dropped by the wayside because you’ve got higher-value things to work on, because you’re having to fight fires – or maybe because you’ve got your priorities wrong.

If you honestly can’t imagine that there’s anything a full-time person could do that would generate enough revenue to cover their salary, that’s not a bad thing.

But often this churns up one or two very-part-time tasks which really ought to be done but aren’t. No need for a new employee of course, but maybe you should re-prioritize those tasks next month.

Sometimes you come up with a good answer, which means you should contemplate help. “Help” doesn’t necessarily mean a proper, 40 hours/week (OK, who are we kidding, 60 hours/week) employee. It could be a part-time consultant. It could be an intern.  It could be an outsourced office assistant. It could be a new partner willing to work for stock.

Which of your business operations do you hate?
Do you like creating new features but hate tech support? Enjoy product demos but hate cold-calls? Need to have your arms around company finances but hate bookkeeping? Love writing ads but hate dealing with ad sales agents? Get excited about your field of expertise but hate writing blog posts and Twittering?

Part of why you’re in business for yourself is creating something from scratch and delighting customers, but the fact is that most business operations just suck. You can’t justify avoiding important tasks because they’re not fun. I know — I’m the worst procrastinator when it comes to those things!

It’s useful to identify these undesirable-but-necessary tasks because you can do something about it:

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If you shut off email, Twitter, chat and the phone – and just buckle down – you might be able to get through some of these tasks in less than 15 minutes. Bookkeeping is like that. Get it off your plate; you’ll feel better.

Mundane tasks might be outsourceable. I’ve found that “virtual assistance” services are surprisingly affordable if you have a lot of little time-consuming tasks.

See if your existing vendors are willing to do some of your tasks for a small fee. For example, accountants often provide bookkeeping services at a lower hourly rate.

Consider an intern or consultant. Before you argue that the cost is too great, factor in the lost revenue you accrue while working on those tasks.

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Can you share the burden with your co-founder or employees? Maybe they don’t hate it as much as you do. You can trade (or switch off) hated activities.

If you’re still stuck on not wanting to spend any money to save time, remember what Dharmesh Shah says: Act as if someone is paying you $1,000/hour for any activities that improve sales (making, selling and your customer’s happiness), and for everything else they’re paying you $10/hour. It’s accurate.  (Before you argue, don’t forget about the cost of lost sales.)

What initiatives could be done half-assed without significant impact?
I know: This is a shitty question. If you’re like me, you are that aggravating combination of perfectionist and control-freak that, on the one hand, leads to stellar work  – but, on the other hand, means some things take too long. Some parts of your business are core to your success: Which features you implement, how you present yourself and interact with customers, discovering how and why people give you money.

But the fact is your to-do list is infinitely long and you have to pick your battles. Your “Contact Me” page has to exist but it doesn’t matter what it looks like. Every blog post doesn’t have to be a work of art. Your Google Ads need variety (for testing), not hours of wordsmithing. It’s better to have an eBook about anything than to have no eBook at all.

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If it can be done half-assed, and it’s not going to impact revenue, maybe it should be half-assed. Allow yourself to delegate (because it’s OK if it’s not done exactly how you would do it). Push more out the door.

If you could get one solid hour of advice from a guru you respect, what would you discuss and what would be the goal of the meeting?
This is a fun way of asking: “What knowledge/feedback/direction is critical to your business right now, and which you’re uncertain about, and which you feel other people are expert in?”

Phrasing the question this way also leads to solutions. For example, maybe you should set aside four hours to get your hands on that guru’s materials (blog, book, podcasts) and immerse yourself not just in advice but in their mindset. Or email them and see if you can get some advice! Or find other people that guru respects and who might be more accessible.