On Tuesday 28th July, I  had the opportunity to share some of my early experiences of taking on our first employees. Sometimes I had to cringe telling stories of the mistakes I made and other times I reflected on just how much I had to learn. I had secret worries, fears and dreams at the time that many new employers have. Here they are (and what I learned along the way…)

1. Am I a failure because I can’t keep up?


I’ve felt this so often. The inbox blowing smoke, the feeling of never quite catching up, the worry of how to deliver exceptional customer service by nervously looking for extra hours in the day. I’ve wondered what I was doing wrong and what changes I need to make in my life to become ever more productive? However, this wasn’t failure but an outcome of success. Gratefully. My business was growing with more customers, more customers and more things to do. This was good! The signs were pointing towards taking on staff to help cohesively increase our capacity to take on new business.


If you want to assess your readiness to take on your first employee, check out the Ambition to Employ Self Assessment tool.


2. What if the person I take on runs out of work… what do I do if they run out of work?


Many of this think we have lots of work for another person to do but that can be a mirage borne out of a feeling of overwhelm of our own workload. On the other hand, we can also be afraid that we won’t have enough work for another person to do and then worry that we would be using hard earned money to pay them to do nothing! In fact, you can swing from one to another on the same day! The way to deal with this is to take a step back and look at all that you do. List the things that you could delegate and question if this could free up ongoing capacity for you or build in extra capability. (The Game Changer Formula by Rory Prendergast can help with this.) That’s where to start shaping a job description.

3. How will I afford this…. It’s the equivalent of a mortgage?


One of the major barriers one can feel about taking on an employee is the feeling of a quasi liability hanging around your neck. There are two things you can do here. The first is to structure it in such a way where there is flexibility on both sides i.e. pay an hourly rate (subject to a minimum number of hours for the employee), offer a six month contract with a view to making a more formal offer afterwards or developing a small network of subcontractors. The second is to develop a cashflow projection for your business. This is one of the most anxiety reducing things that we’ve ever done! Start with your current bank balance. On a spreadsheet, write what you expect to come in and what you expect to go out in order of date. Next, put in the amount that a staff member would cost you and observe how your cashflow would. Finally, add in the incremental benefit that you would expect your employee would add to the business and then you will be in a better position to make your decision.


Also, check out the Ambition to Employ module  “What resources will you need to take on your first employee?”

4. How could I practise?


If you haven’t done it before, managing people can project you into a whole new world that requires different skills than managing customers, projects and deadlines as a solopreneur. The “Managing Talent” module of the Ambition to Employ resource set is very helpful. You can also practise with some dress rehearsals. For example, take on a virtual intern who could work with you remotely for a number of weeks. You could work with an agency to offer a student some experience with you and thus benefit from some reverse mentoring also e.g. CAPA or Career Training Internships. You could enrol in Erasmus for Young Entrepreneur which is an EU funded initiative aimed at enabling new businesses new experiences in working with people and expanding their international networks.

5. Would it just be quicker to do this myself?!


Oh how often the new manager thinks this thought! You give a task to an employee and you think you’ve done so with crystal clear directions. You get a very different outcome that requires you to put in the same (or more!!) time than it would have taken for you to do it yourself. Rather than berate yourself, the other person or anybody else in between, take a deep breath. As your employee what they heard you say and then build a bridge of understanding.


I was at a completely non-business related dinner one night. I was chatting with a lovely woman who worked as a PA for a well renowned business woman. She was telling me that she often has to translate gibberish into a discernible task and only ask one or two clarifying questions. She said “my boss thinks so fast and she expects the rest of the world to keep up with her so I’ve had to learn how…” A couple of weeks later, I was doing a 360 with my own staff and my PA practically echoed her words. It’s so important that you take the time to explain what to do, how to do it in the way that you expect and reflect on where the communication fell down on either side if that didn’t happen.


The answer to this question is yes, it is quicker to do it yourself today, but you will be back overloaded with work again tomorrow if you don’t make this investment in your staff.

6. What if they can’t do it as well as me?


If you’re asking this question, I suggest you think more optimally by asking “where do I find people who can do things better than me?”. Indeed, nobody will do things like you will and it’s quite likely that your customers always ask for you, so it’s possible to feel that if you could just find a clone, life would be great… However, life and business doesn’t work like that. Think strategically about asking for help. Mull over these three thoughts

  • What do you do super well?
  • What do you do just because you have to?
  • What don’t you like doing?

I could give you countless examples of my answers to the latter two questions because that’s exactly what my staff take care of and then I focus my time and energy on answering and following through on the first question.


7. Why didn’t I do this before? Should I take on several?

Things can work out pretty well when your early staff members take work off your plate or add value in their own way. You can be super enthusiastic then and want to take on more very soon after. I suggest that you get used to having the first person well embedded first. The reason I say this is that you soon move into a world where you need to create a culture, a sense of interdependence between employees and being politically aware of how you manage people together. If you want to look into this much more, check out “The Leadership Pipeline” as this book explains all about the different phases of leading people. Also the Ambition to Employ resource “Building a team of Two +” spells out what you need to consider and do at this stage.