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Thinking About Your First Hire? Answer These 7 Questions First

Barnaby

Barnaby Lashbrooke

Founder and CEO of Time etc, author of The Hard Work Myth

11 minute read

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The decision to hire usually gets made at the end of a bad week. You worked late three nights running. A good client's email sat unanswered for four days and you had to open with an apology. You spent Sunday morning matching invoices to bank transactions instead of doing anything that moves the business anywhere. By Monday you've decided: you need someone. Time to write the job ad.

If you've never hired before, it's easy to assume hiring is a clean fix. Problem: too much work. Solution: another set of hands. Ad goes up, someone starts, pressure comes off. That's the version in your head, and the gap between it and what actually happens is usually wide enough to catch founders out.

For plenty of founders, hiring is exactly the right call. Some businesses genuinely need a person in a seat five days a week with your business in their head and nobody else's, and nothing below is an argument against that.

But when reality falls short of expectations, it usually traces back to the questions below, and to the fact that nobody thinks to ask them before the ad goes live. Every one of those questions has a legitimate yes attached for some founders, and going through them now saves you from finding out the hard (and expensive!) way.

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1. Do I have the capacity in my schedule for the recruitment work itself?

Chances are, you're hiring because you've got too much to do and not enough time to do it all in. In most cases, founders rarely account for how much hiring adds to their pile before it takes anything off it.

Once you’ve ticked writing the job description and posting the job ad off your list, the applications come flooding in, and it’s on you to figure out which ones are worth your time. Greenhouse, one of the largest hiring platforms, told Fortune that the average job ad on its system now draws around 254 applicants. A lot of that volume is AI-generated, so applications increasingly read the same, and telling the serious ones apart takes longer rather than less time.

Then comes the interview process: reaching out to candidates, the back-and forth to schedule dates and times, the interview itself, the second rounds, the test tasks, and the reference checks. SHRM's 2025 benchmarking found that screening and interviewing each take eight to nine days on average, so that’s another two and a half weeks down before you’ve even sent an offer.

If you've got a genuinely clear couple of weeks, or someone who can run first-round screening for you, this is all manageable. If you're reading this at 11 pm because it's the only quiet hour you got today, you already know your answer.

2. Can I afford the recruitment ramp time?

The clock really starts when you write the ad, not from their first day on the job.

SHRM's 2026 benchmarking puts the median time to fill a non-executive role at 39 days. That's the midpoint across organizations that also have their own recruiters, hiring software, and processes they've run before. A founder juggling applications between client calls and deadlines rarely beats that number (without cutting a lot of corners).

Then once a new employee starts, experts say it should take around 6-8 weeks for them to be onboarded, get to grips with their role, and start being productive without constant supervision and oversight. During those weeks, you’ll be helping rather than being helped, so expect your days to get even busier before they get better.

The question isn't whether that's worth it, because usually it is. The question is whether you can keep going the way you currently are between now and then.

If you're hiring way ahead of a busy period you can see coming, that timeline is fine and you're doing this the right way round. If you're already reaching a breaking point, three months is a long time to hold on.

See: When Is It The Right Time To Hire Admin Support As A Founder?

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3. Am I the person who is going to manage them?

Hiring someone means becoming an employer, with all the admin that comes with it.

The contract. Payroll setup and the monthly run. Onboarding. One-to-ones. Feedback when something isn't landing. PTO requests, sick days, appraisals, the pay conversations further down the line, and the harder conversation if the work isn't good enough.

Paychex found that 34% of business leaders already spend more than 10 hours a week on HR administration, and most of those companies have somebody else to share it with.

And no one really warns you what managing a new hire does to your focus. When a newbie is still working out where everything lives and what good looks like, they ask, several times a day. As they should.

Each question may only take a minute, but Gloria Mark's research at UC Irvine found that when people picked an interrupted task back up on the same day, it took them an average of just over 25 minutes, because they'd dealt with two other things in the meantime. Answer four of these questions before lunch, and you could lose the best part of two hours, all of it taken from the work only you can do.

Some founders like managing people, or have done it before and know they're decent at it. If that's you, this is the part of hiring that gets better rather than worse.

4. What happens when they're sick or on vacation?

In small teams, you're their cover. Whether it’s PTO in the summer or the flu during the holiday season, the day-to-day tasks become yours again.

Bigger companies can absorb that across a team, but chances are, you would have to absorb it after hours. That, or the work has to wait.

If you can find someone who can cover, or the work will happily sit for a fortnight, fine. Most founders have neither.

5. Am I prepared for if it doesn't work out?

Nobody hires expecting the worst, which is exactly why it's worth ten minutes now.

Legally, it all lands on you: the contract, probation, running a fair process, notice, and knowing the rules well enough to follow them. Employment law moves at its own pace, so if something isn't working, you could be stuck in a tough situation for weeks while you do things by the book.

Financially, it’s no secret that a hire that doesn't work out costs far more than the hire itself. SHRM's 2025 benchmarking puts the average cost per hire at $5,475 for non-executive roles. According to Gallup, replacing that person costs 50% to 200% of their annual salary once recruiting, interviewing, training, and lost productivity are counted. So a $50,000 role could end up costing a further $25,000 to $37,500 before you're back where you began.

Practically, everything you'd taken off your plate goes straight back on it, for however long it takes to hire and get someone up to speed.

If you have enough time and resources to absorb a false start, this is a risk you can carry. It's the founders who can't afford to go back to square one who need to think hardest about it.

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6. What if what I need changes in six months?

Nothing about running a business stays still for long. You try something and it works, so you do more of it. You realize something’s not working, and you phase it out. One client might leave, and a bigger one turns up two weeks later.

The thing is, your new team member applied for a specific job with specific hours. You both signed something confirming it, and they've shaped their life around it: childcare scheduled around those hours, personal commitments in the gaps, rent payments based on the hours on their timesheet.

So if things ramp up dramatically and you need more hours from them to keep on top of it all, it may be much easier said than done for them to agree. And even if they say yes, it might work for a while, but in the long term, no one does their best work when they’re stretched thin.

The other direction is harder still. A full-time hire needs a full-time amount of work, and finding it falls to you. If things slow down, you risk paying for hours you can't fill. Reducing their hours means a pay cut for someone who arranged their life around the old number, and it can cost you the person entirely.

If your workload is steady, or seasonal in a way you can predict, none of this bites. If you can describe next year's work with confidence, skip this question.

7. Do I just need one set of skills?

This runs on from the last point. Say you hired someone full-time to take your financial admin off your plate: expenses, invoicing, paying the bills. Six months on, the thing weighing you down the most is social media, and you'd love to hand that over too. But the person who's great with your finances isn't necessarily any good at content. Those are two separate skills, and you hired for the first one.

That's the catch with a single hire. You get one person, good at the specific things they're good at, and the rest of the list stays exactly where it was. Pay a full-time salary for someone to handle your invoicing, and you've bought their whole skill set while only using a fraction of it, with everything else still sitting on your plate.

The opposite is its own trap, too. If you're looking at the whole scope of offloadable tasks in your business and hoping one person can take the lot, be careful. It’s incredibly rare for someone to be genuinely good and experienced at things like finances, copywriting, and travel management all at once. You’ll end up with a few things done well and the rest done by someone out of their depth.

If you've got enough of one kind of work to fill a genuine working week, and it's the kind that benefits from someone building up deep knowledge of your business, a single hire makes complete sense.

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Bonus question: what’s the alternative?

If your honest answer to most of the above was a wince, this is the one that matters most.

In many cases, when founders are at the point of asking themselves, “Am I ready to hire?” what they actually mean is, “What's the fastest way to get this work off my plate and keep it off?”

Hiring is one route there. Time etc has been the other since 2007.

  • All the recruitment work done for you: Our assistants are screened, interviewed, reference-checked, and identity-verified long before you ever need one. Only the top 2% of applicants make it through to work with us, on average.

  • Matched in 1–2 days, not 39: Most founders are handing work over to their new assistant within a day or two of getting started. Which means the only thing left to work out is what you'd do with the extra space in your weeks to focus. You get to answer that within the week here, rather than after two months of screening and a notice period.

  • Someone to do the management job for you: Managing an employee can feel like a whole extra job landing on top of the one you already have. So Time etc gives you a whole extra person to do it all. Your dedicated Client Success Manager handles everything from matching you with the right assistant, performance, payroll, problem-solving, and handling those awkward conversations if they're ever needed.

  • Peace of mind, guaranteed: Every Time etc membership is backed by a satisfaction guarantee. If your assistant isn't right for you, for any reason, we will find you a replacement, completely free of charge. A bad match costs you a conversation rather than a rebuilt hiring process and three months of your life.

  • Access to more than one skill set: You pay for hours, not headcount, so working with additional assistants only costs you the hours they work rather than another full salary.

  • Cover and flexibility built in: If your assistant is on vacation or off sick, we make sure everything’s covered so the work keeps moving while they're away. Beyond that, you keep complete control over the level of support you have, whenever you need it. Busy spell coming up? Scale your support up to handle it. Things quieting down? Just say the word and dial it back. There are no long-term contracts tying you down, and you can cancel any time if things change.

See: Virtual Support vs. Traditional Hiring: Why Founders Are Switching

Ready to start getting your weeks back?

You know the work you'd do if you had the room for it. The strategy you keep postponing, the part of the business that only moves when you push it, the evening you'd rather spend doing somewhere else. That's what Time etc is for, and it starts with one conversation.

Book a free consultation and talk through what's eating into your week, and what you'd rather it looked like.

Choose the membership plan that fits, sign up, and we'll take it from there, starting with finding you the right assistant.

P.S. Want $150 off your first month of support? Answer a few quick questions to get personalized task recommendations for your business and unlock your welcome discount.

| Book your free consultation | Try our Task Wizard and get $150 off your first month |

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About the author

Barnaby
Barnaby Lashbrooke is the founder and CEO of Virtual Assistant service Time etc as well as the author of The Hard Work Myth, recently recommended by Sir Richard Branson. Barnaby is a Forbes Columnist on productivity and is also an accomplished entrepreneur, selling more than $35 million worth of services.

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