6 important questions to ask when hiring for the first time

Nov 12, 2020

Does the idea of hiring your first team member fill you with panic, confusion or overwhelm?

You’ve got no idea where to start — how to find the right person or what they’d even do! You wonder if you can even afford it and whether now is the right time to hire.

But here’s the thing.

You’re one person and there’s only so much you can do in your day.

Want to scale, create more balance or make more money in your business? Are you a corporate leader who wants to free up more to focus on strategy and leading your team? Then getting some support may be the right next step for you.

With my HR & recruitment background, I’ve advised many companies on their hiring strategy. But it’s always fun to support entrepreneurs with making the first hire in their business!

A recent client conversation inspired this week’s article. I’m sharing the exact questions I got them to consider before hiring the first employee in their company. These are the questions you must ask — even before advertising or interviewing.

Read on to discover if you’re ready to make your first hire.

You’ll walk away with clarity on your new team member’s role, duties and exactly what you’re looking for. All so you don’t make any hiring mistakes, select the right person and avoid overwhelm in the process!


This is a common question I get from business owners. The answer depends on your capacity, financial position and how long you’ve been in business. But usually, it’s well before you think you need to!

If you’re overwhelmed, drowning in ‘admin’ tasks, working late nights and weekends. Are struggling to find time to work on your business. Or are being pulled away from work that makes you money, chances are it’s time to hire.

For corporate leaders, if you’re still doing lower level work or don’t have anyone to delegate to. Know your team is constantly overwhelmed and struggling with their current workload. Or you’re the bottleneck stopping your team from getting their jobs done — you need some extra support.

Not sure where to start?

Begin with a brain-dump of all the tasks you’re spending your time on. If you need to, keep a running list of all your activities over the course of a day or week.

Then, eliminate, automate or delegate anything outside your zone of genius. This is what you’re good at and love to do. And of course, the work you’re paid for — that only you can do.

For me, this is time spent coaching clients. As a lawyer, accountant or HR consultant, it would be client advice, meetings or technical work.

Next, you’ll use this task list to create a job description, interview and advertise if needed. For solo-entrepreneurs, I recommend making your first hire a part-time virtual assistant — even for a few hours each week. This will free up more of your time as they take the time-consuming admin tasks off your hands.


Start by getting crystal clear on what you’re looking for in your ideal team member. The biggest mistake leaders make is getting excited about a potential hire. Then trying to accommodate them — without giving any thought to what it is they need in their team or business.

The problem with this is they often hire the wrong person. The individual’s skills are not a fit for the areas their business needs support with. Or, they’re the wrong personality fit for the role, the leader’s style or culture they want to build.

Ask yourself the questions to follow to get clear on who you’re looking for.


To define the job responsibilities, go back to the task list created in response to Question 1. What are the:

  • One-off tasks you want them to tackle immediately
  • Regular tasks they will work on each week
  • Big projects you need support with now or on an ongoing basis
  • Systems — any processes or procedures you want them to create or implement

Also consider:

  • Supervision — How much supervision can you provide? Can they perform this role remotely — or only in person?
  • What days/hours per week do you want them to work — or are you flexible?
  • Pay — how much will you pay them?

Once you understand the main job requirements, the next step is to clarify the skills you’re looking for.


I recommend breaking this down into personal and technical skills. First, establish the personal skills your ideal team member requires. Personal skills refer to their personality traits, qualities, strengths, attitudes and values.

Cultural fit is critical, especially for your first hire. What culture do you want to build in your team or business? And what person will work best with your style?

Personal skills also depend on the job responsibilities identified in Question 3. Remote team workers will need self-motivation, focus and the ability to work independently. Assertive communication skills, top presentation and confidence will be essential in client facing roles.


Second, determine the technical experience needed to perform this role. Think — existing experience, formal qualifications and certifications, technical or industry knowledge.

Consider what you’re willing to be flexible on. What technical skills or experience are a non-negotiable? Are there certain areas you’re willing to train someone on?

If in doubt, remember technical skills can always be learnt. But personalities and attitudes are harder to change.


Once you’re clear on the role and who you’re looking for, reach out to your network for recommendations. Ask other business owners or leaders who they’ve worked with, trust and recommend. Or post on your social media pages, say you’re hiring and ask your community for suggestions.

Advertising should always be your last resort. Post the job on your company website, business social pages or use a professional platform like LinkedIn. LinkedIn’s search function allows you to match people based on personal and technical skills. Review their recommendations, activity and common connections to assess their suitability.

Finally, be thoughtful when short-listing and rejecting potential candidates. Send a quick canned email (saved template) to tell applicants they’ve been unsuccessful. If someone isn’t a fit for this position but you’d like to consider them in future, be sure to let them know.

This way, when you’re ready to hire your next team member, you already have people in mind to contact!

Hiring your first (or next) team member can be overwhelming — but it doesn’t need to be this way! These tips have helped my clients make a successful hire with ease. I hope they support you too.

Want support to develop and retain your most valued team members?

Get in touch to arrange a complimentary, no obligation conversation to discuss your organisational needs and how I can help.

Stacey Back is a globally recognised and certified career coach, speaker and facilitator. She helps high-achievers at a career crossroads find the work that lights them up, increase their income, impact and create a career + life on their terms. Stacey works virtually with individuals and organisations based across the globe.