How to Hire the Right Employees for your Online Business

How to Hire the Right Employees for your Online Business

At some point, you’ll decide to grow your online business and need to hire employees. It’s tricky because you want someone who can think for himself and also win for the team, at the same time.

First of all, please remember that your online business is still a business - even if the medium and style of delivery is different.

If you can never seem to find the right staff or creatives to work with you, maybe it’s time to change your approach to hiring. Don’t treat it like a hobby or personal project. It is a business decision.

Second, banish the thought that it’s hard to find the right employees. When you think like that, it becomes a self-fulfilling prophecy because you’ll approach the process from a place of fear and that just never works.

There are competent creatives out there with excellent character - people who go above and beyond to make sure your business succeeds. Yes, they exist. So before you go on a rant about how millennial creatives don’t really like to work, check that the good ones want to work with you.

My business attracts high quality creatives, and it’s not just because I pray about it. It’s also because they see me as the type of person they want to work with.

How to attract the right employees to your business

Contrary to what most people think, hiring is not all about being able to spend money. While it’s important that you’re willing to pay them well for their time, here are a few more things you should know. High-quality staff and creatives will come your way when:

  • You are clear about your mission and what you’re trying to accomplish
  • You build a genuine personal brand that people want to rally around
  • You share content that amplifies your brand message
  • You tell impact stories that they’ll like to be part of (not just shouting about your 6-figures all over the place)
  • Doing business with you makes them better - they want to work with people they can learn from through constructive feedback, not complaints and bullying.
  • Being associated with you enhances their brand - the same way working with some companies look good on your CV
  • They’ll learn tangible and transferable skills from working with you (have a plan for their learning and growth)

If you look closely, you’ll see that your ability to attract and retain valuable people in your online business depends on your personal brand.

You don’t have the hiring budget and corporate governance of large organisations, so you must leverage what you have: your identity and reputation.

The best staff I’ve had so far, are the ones who were actively and specifically seeking an opportunity to work with me or someone like me.

Personal branding is an investment in your business.

What I look for, when hiring

Writing Skills

For every role I fill in my company, I ask applicants for a writing sample. I give them exercises that involve writing (this is also why I request a cover letter, not a CV). Why? Your writing tells me how your mind works. If you write clearly, it’s a sign that you think clearly.

Good writing shows discipline. It takes a lot to organise your thoughts and communicate them in writing. If you can be committed to yourself enough to do that, you’re already above average.

My team is remote and most of our communication is done through writing (not unnecessary meetings). Great writers communicate well and make things easy to understand. If you write poorly, you won’t fit in, you’ll waste time, resources, and look incompetent, even if you’re not.

Also, we’re an education company. A lot of our work is done with words. If you can’t write to explain how something should or should not work, you can't help our clients.

Finally, people who don’t write well complicate other people’s jobs. No matter the role, writing skills always pays off. There will always be work for good writers to do. But if you don’t have good writers on your team, there will always be more work for you to do.

Technical Competence

Good writing doesn’t replace competence and capabilities. That's why I write good job descriptions in the first place - so it’s clear what skills are needed for the job. Among all the competent people who apply, we’ll favor the best writers.

Of course I know people outsource their cover letters, but that doesn’t stop me from asking for it. I have a process to counter this deceit later.


After sieving out those who were intentional enough to write well, I look for the right attitude. If we don’t find someone with the right attitude, we start again - because attitude is crucial. 

You must know what attitudes and values you’re looking for. I look for values that fit our company culture. We value continuous learning, proactive communication, self-management, matching aspirations, commitment to a career, and more.

How do I check for these?

Through multiple conversations - with the candidate, their past employer, and references.

Interviews are quite tough, because people lie on interviews and there is no single question in the world that always predicts the best candidates.

People obsess over the right questions to ask, but the questions are not as important as what the answers tell you about:

  • What the candidate would be like in their role at your company. 
  • What it would be like to work with them every day.
  • Their values and work ethics.

To get these, you need to listen to how they say what they say, and what they choose not to say. 

FULL DISCLOSURE: Interviewing is just one part of my hiring process. We also do a test-drive where the person gets to work with us for one month (with pay) before we finally decide.

I have a few personal rules when interviewing:

RULE ONE: I ask “why” instead of “what.” The question “What’s your biggest weakness?” is useless to me.

RULE TWO: Ask the same questions across candidates for the same role. 

Winging questions per candidate will tamper with your clear judgment, and feed your bias. Give them the same opportunity.

RULE THREE: Current motivations & Past performance are good indicators of future behavior.

Questions I ask to help me find the right candidates

Based on my rules above, I keep a running list of interview questions that I pick from. Here are some of them:

3 Questions I ask myself 

  • What should our work day to look like once this role is filled? Some people like autonomy, some like tons of direction at every step. This is where you decide who you want. Yes, your priorities and preferences matter when you have a small team.
  • What are the most important skills to us here? A content writer needs industry knowledge more than leadership experience. Your personal assistant doesn’t need to come with Webinarjam knowledge. They can learn that. You can teach software. You can’t teach patience, personal discipline, or professionalism.
  • What is the most important thing I need to know about this person? There is no time to learn their entire history, so you need to know why you’re asking the questions you ask. Also, read their documents before the interview to save your time.

25 Interview Questions I ask Candidates (PLUS What I listen for) 

  1. Tell me about yourself (I’m looking for self-awareness)
  2. Sum up your experience since you left school
  3. What do you hope to do with your life? (.. ability to dream)
  4. What have you done so far with your life? (I may be looking for execution, confidence, or candor. It depends)
  5. What would you do if I asked you to do something you don’t know how to do (.. ability to deal with unknowns)
  6. Tell me about a time you were working on a project you really loved but didn’t turn out right (.. ownership)
  7. Tell me about the best boss that you’ve ever had. What did you like about them, and why? (.. values, humanity, and expectations)
  8. What do you like about your current job and why?
  9. What don’t you like about your current job and why?
  10. What’s a personal deal breaker that would make you quit your job?
  11. What’s your favorite thing about the role you’re applying for?
  12. How will you measure success in your new job role? (.. results-orientation)
  13. Which clients/ projects have you most enjoyed working for? Why?
  14. Are there any tasks that are NOT your favorite, even though they technically fall under your job description?
  15. How do you usually meet your goals? (.. Productivity & execution)
  16. Tell me about a time that you messed up. How did you fix it?
  17. Tell me about a time that you had a difficult interaction with a co-worker. How did you resolve it?
  18. Tell me about a time that you successfully led a project. How did you do it? What were the challenges?
  19. How do you normally give feedback to a co-worker about something they did or didn’t do?
  20. Do you have experience working on a remote/online team? 
  21. If you needed feedback from a remote team member right away but they weren’t responsive, what would your next step be?
  22. What do you think the challenges of working remotely are, and how would you handle them?
  23. What was the last thing you learned?
  24. What was the last thing you taught someone?
  25. If we were to move forward with you in the position, what are the first 3 things you would do? (I prefer this to “Why should we hire you?”)
  26. Do you have any questions for me? Good candidates have questions

Hiring is an imperfect process

Show me a company that claims they have a perfect hiring record, and I’ll show you a company that is lying, lying, lying. Sorry, they’re lying. 

But you can learn to improve your approach to hiring.

You’re going to do it wrong at some point. You’ll hire some people who won’t fit in, who will quit, or who you’ll have to fire. And that’s okay. But never let your fear of hiring “the wrong person” stop you from hiring at all.

Hiring isn’t fail-proof and we get it wrong sometimes, but I hope this is useful for you if you're hiring soon, or hoping to work for a digital entrepreneur.

Recommended Reading: REWORK

A few years ago, when I spoke at WordCamp Lagos, I met a panelist who worked for an international remote company and asked his advice on hiring - based on his experience working on a remote team. Among other things, he recommended that I read REWORK by Jason Fried and David Heinemeier Hansson. That book is gold and I’ll pass on the same recommendation to you. Read REWORK 

Your Turn!

What are your favorite interview questions to ask potential hires, OR What is the favorite question an interviewer has asked you?

I’ll be looking out for your comments below!

One Comment

  • Vicky

    Thank you TM, these are great tips. It not only helps employers but also employees to know what areas to build and how to prepare before going for an interview.

Comments are closed.

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