You’ve probably clicked on this post because you’re facing challenges in recruitment and team management. Every growing business does, including mine – so you’re not alone! I’m going to list my top 5 challenges in growing and leading a team and how I deal with them.


Not sure how to make sure you’re hiring the right people, or how to juggle the different personalities in your team? These are my experiences on those very subjects and more. Let’s get into the latest chapter of the Diary of an Entrepreneur…


Challenge 1: Recruitment


What came first, the clients or the team?

Recruitment, for me, is very much a ‘chicken and egg’ scenario. Without clients, you can’t grow a business, and without a team (yourself included), you can’t grow a business either. So, at which point do you take on staff, and at which point do you put your foot to the floor, stretch capacity and take on more clients?

If you run a business, you’ll have been in this moment. It was just you working from home, an opportunity came and decisions had to be made about going it alone or bringing in more people. For me, this moment came when our first six-figure client approached me – I talk more about this experience of winning my first six-figure client here.

When that contract landed, I just knew it was time to start hiring people.


Fork in the road

When we get to this stage, we either have to turn work away or we have to grow as a business. To decide what to do, you also need to know where you want your business to be. It’s taken me years to get here, but I’ve got very clear goals and visions for the business. I know where our limits are and where our end goal is, and right now I’m working towards that.


Is there truly a right time to hire?

I’m not sure there is, from my experience. I think it’s more of a 80-90% chance of it being the correct time if you’re the cautious type, and there’s a 40-60% chance if you’ve got a more adventurous side.

What I mean by that is that if you’re more cautious you’re going to hold off repeatedly and wait for the almost-perfect time. On the other hand, if you’re a bit more adventurous (like myself), you’re probably going to be (or want to be) several steps ahead – and it’s a bit of a gamble.


When and how do I find new recruits?

I try to hire slightly ahead of the growth curve, and I’m always looking for talent and building relationships with potential new recruits for the business. I do a lot of this on LinkedIn, when I’m out networking and when I’m scouring YouTube for the latest cool videos. I’m always trying to find the people behind those projects, seeing if they could be a potential fit for the business in the future and reaching out and connecting with them.

As business owners, we’re very sales-heavy: we’re building those relationships with clients, but we’re also focused on doing the same with the team. Getting the right team in place to grow the business as you want to grow it is really important, and you can’t always get that through the normal recruitment routes. Sometimes you have to go through a ‘back door’ and it’s your job, as the head of the business, to do that.

Saying all of that, I’m a bit more cautious these days than I used to be – but I still tend not to dilly-dally. A decision needs to be made, we need to hire people and we need to get on with it!


The football analogy

I’ve mentioned this before, but I manage my team like a football team. I think this analogy is really fascinating – and, importantly, it does work!

So, when it comes to recruiting, I’m managing everything like a football team. That includes scouting for new players, and I think that plays a really important part in managing your football team. I’ve got my goalkeeper, defence, midfield attackers, B-team, substitutes, coaches… you name it.

For headhunting, LinkedIn is probably the most powerful tool. (As for sales, you can learn more about how I use LinkedIn to find clients here.) However, you can also view CVs online, look on portfolio websites, and even simply search on Google.

We try to recruit as local as we can, because that’s just the way we want to grow things at this moment in time. However, we have worked with people up and down the country and, indeed, around the world!


My to-do list is my biggest recruitment tool

I really believe this: it’s tougher to recruit when it’s just you in the business than when you’re at 5, 6, 7+ staff. For me, I really struggled with who to hire first – this is when my to-do list became my biggest recruitment tool.

I look at all the things I shouldn’t be doing in the business, and I work out how I can outsource it, delete it, delegate it and so on. If you’re interested in learning more about how I keep up my productivity and manage my workload, I talk more about my to-do list and wider CEO operating system here.

Today, I’ve got a very clear roadmap for my team formation in the coming months and years. It’s a little less daunting for me now and I’m a little less clueless – but when you’re at the first couple of hires, it is literally a finger-in-the-air moment.


Interviewing and the importance of personality

In the early days, I was an instinct man – and I’m afraid this resulted in more misses than wins. Sometimes I’d hire somebody without even meeting them – it’d just be a phone call and a ‘yes, you sound great, come in and let’s trial you for a week’. However, I soon discovered that recruitment is an art in and of itself. There is real strategy, focus and experience needed in interviewing.

Over the years, the interview process has definitely evolved a lot. Right now, I’m fully focused on finding the right talent but with the best possible personality fit with the business. For me, it’s 30-40% skill and talent, and 60-70% attitude and personality. Are they the right kind of fit for this business?

You can have the most talented people on the planet working for you, but if they’re a bad egg with the wrong attitude and they don’t like you or your business… it’ll end up kicking you in the backside in the long run. Because of this, I’m big on the whole personality thing.


The interview process

At the moment, we work on a four-phase interview process. This sounds excessive – and it probably is – but there’s method in the madness!

  • Phase 1 is a short video on why we should be hiring you. Straight away, this one filters out a lot of people who just don’t care about your business or working for you.
  • Phase 2 is a project-based test in the area of your expertise.
  • Phase 3 is the first in-person interview with me and the senior members of my team.
  • Phase 4 is an interview with just me. At this stage, I don’t need to go through their CV or figure out if they’ve got the skills and talent for the work because that’s already been done. Now, it’s more about if they’re going to fit in with the vision that I have for the business.

Again, the reason for these 4 phases is that it does a really good job of filtering out those lazy ones who have no interest in working for your company. Instead, you end up with candidates who are willing to put in the effort – and that is oh so important!

This method has worked out really well for us and we’re definitely going to stick with it. It might sound excessive to some people, but hiring is a massive commitment! It’s huge! It’s also a big gamble, because people can interview really well, but when they get to doing the work they just aren’t able to cut the mustard.


Challenge 2: Onboarding


What is onboarding?

Onboarding would normally be a list of things that need to be done prior to starting employment with us and tasks to complete during the first few weeks.

If you’re thinking about hiring, having an onboarding process in place is something you should be doing from day one. Show them round the office, train them on health and safety, provide them with starter packs, set up their logins, install their apps, and just generally get them aligned with who and what your business is.

Eventually, I will need someone in the business who can bring people in and help with onboarding. I want people to feel special when they arrive at work on their first day – buying them uniform and gifts, having everything set up ready to go, going for drinks and so much more. At the moment, it’s difficult for me to do all of this with every single person, but it’s something I’m very conscious of.

If you’re a business owner, you should be as well! You’ve got to remember what your new staff have gone through – not only have you gone through a process, but they’ve gone through a process too. They might have lost a job or it might be their first job – so it’s a huge, life-changing deal for them. They’re going to be nervous, so from day one, make them feel comfortable.


Challenge 3: Cashflow


Can I afford new staff?

The answer for most people will probably be no. There’s never really a good time financially to hire; there’s always an argument not to hire, because you’re saving a load of money. That’s fine, but then the workload starts to bottleneck and we have car crash situations.

Hiring new staff could free up so much time which, in return, will deliver so much more value for the business. The value is not just how much cash you could bring in, but how much you could be saving of your valuable time. If you added up just how much your time is worth to the business, you would be astounded. What’s more, if you’re doing those jobs that you could be paying someone £15-20 an hour for, compared to £100 an hour, it’s a no-brainer.

It might be a short-term hit against cashflow, but if you hire smart, it could pay dividends in the end. Plus, if you’re hiring in sales or marketing, they could generate more revenue and so it pays for itself.

My first hire freed up about 75% of my time and relieved so much pressure off my shoulders. In just a few months, I was able to do what I do best: grow the business.


A 3-month safety net

In an ideal world, we would have 3 months of operating costs in the bank at all times. However, the reality is a very different matter, and very few companies can afford to have this. We may get there occasionally, but then something crops up and we need to dip into it. When I started, I wasn’t thinking about having 3 months of operating costs – we were living month to month, which was probably a very big mistake. Now, however, we’re much more focused on this.

Make no mistake: hiring will impact cashflow. You might have to hire less experienced staff to start with, which will be less of a strain on cashflow and get you going. However, you will eventually need to hire more experienced and skilled talent if you are truly going to grow the business.

I guess a mistake I made in the early days was that, with no disrespect to them at all, I was hiring too many of those inexperienced people. It was a long time before I made a significant investment in hiring a more experienced and expensive member of the team – but when I finally did, it paid off. I hired someone to help manage the team so I could step back a little bit, and it also provided a massive boost to revenue.


Challenge 4: Coaching, training and development


Who’s responsible?

When it’s just a handful of people in the business, it’s you who will be responsible for coaching, training, development, HR, health and safety and everything in between. You will be very, very involved in all areas of your team’s work, and it won’t be until you reach 7+ staff that you can start to introduce a management tier. However, even then, you’re still heavily involved with managing a team.

You should consider this when hiring: yes, it’s great because they take the burden off some of the workload, but it still demands commitment from you for a long while until you’re up in the 20s and 30s in staff. Only then can you probably truly step back – if you want to, and if you’ve got the right management structure in place.

Going back to my football metaphor, you need to coach each member of the team, help them to improve in their area of expertise and work on their collaborative skills. You also need to be incredibly observant so you can assess your team individually and as a whole. This requires expertise, which you might not have just yet.

After this, you need to figure out where improvements need to be made and how to make those improvements.


The scorecard

I believe a business needs a scorecard, but individual members of the team also need a scorecard. Each member of my team has a number, and this number is based on three things:

  • Talent
  • Effectiveness in the business
  • Attitude

This gives me some indication of where we’re at, how they’re performing in the team and what we need to improve on. What these numbers are in your business is entirely up to you and how you want to grow and work with that team.


Challenge 5: Dealing with personalities and HR


Everyone is different

This is something I learned very quickly. I thought I was a good people person and good at working people out, until I started hiring staff – it was only then that I realised I knew nothing.

Everyone responds differently to instructions and advice, and not everyone is going to be a perfect fit for your business. So, it’s all about compromise! Especially if you want to grow a diverse workforce. You don’t want everyone being the same! You’re not looking for robots or clones, you’re looking for people.

The art is learning how to manage many personality types, and I’ll be honest – this isn’t my strong point. I believe that everyone instantly understands what I’m asking for, and sometimes I come across a little bit abrupt and vague at times. However, I’m self-aware enough to know this and I even joke about it with the team because they all know me quite well by now.


Filtered conversations

That’s why I want to build a management team that is much better than me at working with different personalities. It’s something we’re working on in the business at the moment, and as a result, I don’t have direct management on most of my team now. Instead, I have a layer of management in place who have conversations with me then deploy these to the rest of the team.

The only time I do chat with my team is in our one-to-one meetings once a month. This is a chance to have a non-management type of chat, asking them how they’re getting on and seeing what we could do as a business to make their job more enjoyable.

It’s a much better place to be in and it’s taken me years to get here, but I hope it continues.


Having a mentor

I’ve also had a business mentor for a good few years now, and he’s fantastic. He’s absolutely brilliant at managing people, and he’s helped me improve in this area.

Improvements still need to be made, but having a mentor has definitely helped me become a better people person. I highly advise that you get a mentor immediately!


Entrepreneurs don’t make good managers

Business owners can often be misunderstood and a bull in a china shop. We don’t mean to be, but we’re stressed and have a lot going on. Therefore, we should not be unleashed on our team as that team grows, because I don’t believe entrepreneurs make the best managers of people. Don’t get me wrong, some are really good at it, but most are a different breed.

Furthermore, the best thing I ever did was hire an external company to look after our HR responsibilities. This is something you must do from day one of hiring somebody.


If you want to hear more about my entrepreneurial journey, check out the Diary of an Entrepreneur podcast on all available platforms – I talk all things business in terms of my OWN journey and experience. It’s not one to miss!


Thank you for reading this chapter of the Diary of an Entrepreneur. I must stress, I’m not trying to teach you anything. I’m just sharing my journey, and if it motivates you, then great – job done!


If you’d like to chat more business, feel free to get in touch with me here or you can email me directly at