How we hire people at LeaveWizard

A step by step process with 100% success rate

When we were bootstrapping LeaveWizard, our annual leave planner online product, we needed to work as consultants to fund our growth. During that time we gained a lot of experience in hiring for a variety of organisations of different sizes and industries. While hiring for clients is often restricted by rules dictated by them, at LeaveWizard, we are very much free to design and improve our own hiring process.


For a number of years at the start of our journey, as a bootstrapped startup, we had very little funds and couldn’t even dream of hiring other people to work with us. Eventually, as our holiday planner began to grow, we reached a threshold that allowed us to bring in others to help us. We had made a number of less than perfect appointments until one day we realised that we needed to change our approach to hiring.


Thinking about the people we would like to work with, we figured out that CVs and online profiles and even feedback from past customers add little value and tell us very little about the candidate.


Here’s our brief evaluation of the different tools we knew about and had considered


  • CVs and online profiles could be good to gain an initial idea about the skills the candidates say they have. Very often the information on such documents isn’t reliable and has to be validated.


  • Feedback from their other customers or past employers could be great, however the key phrase here is “from other”. We don’t know these others, we don’t know what their values are, and we don’t know what their standards are. So feedback can only serve as an initial indication of whether the candidate would end up on the shortlist for the next stage.


  • Interviews are great and they do add a lot of value, however they require time commitment usually from a few of us. Interviews are a lot about judging communication and fit as well as capacity to handle the work. Interviews are not perfect and selecting someone on the basis of an interview is still a big risk. Even more so when you work with limited resources.


We started to think a little bit more about what we want from our future colleague. Think about how it would feel when they are working with us. Using our imagination fuelled by what we’ve learned about the person never felt like the best option, especially as we’ve had several failed attempts.


We listed what we are trying to establish during the recruitment process


  • Can this person complete the standard work we expect them to do with a good quality level? For example, if we were hiring a support analyst, could they handle an actual support request from one of our leave planner customers, from beginning to end. Or if they were a software developer, could they take a small feature, explained by us in our usual way, and progress it through to completion with the right level of quality.


  • Does this person communicate well with the rest of the team? We are a fully distributed, remote, async team. Being able to communicate well over chat rooms and online calls is rather important in our world.


  • Does this person have the right attitude towards problem solving and learning? Being a small team we often work together to solve complex problems and even more often we have to pick up and learn new skills.


  • Will this person be a good fit for our team? Even if we are satisfied with all of the above, we cannot progress with people who are unable to adopt our values - authenticity, honesty, friendliness and helpfulness.


After some consideration we decided to try an approach in which the last step involves paying (at least) the two top candidates to perform a day or two of work on our team developing and looking after our holiday tracker app. This allows us to see them in action, see the quality of their work, and understand how they work and how they behave in our team. The obvious downside being that we have to part with some of our limited funds.

We didn’t think that this step could guarantee 100% success, we were only hoping that it would increase the chances. Our experience so far however is 100% success.


Here’s our process in full

  • Start by agreeing on a description of the role. Our existing team must agree where this new person will be sitting in the team and what would the expectations from this person be.

  • Review profiles of people based on their skills, communication and feedback from past customers or employers and create a shortlist.

  • Invite the people on the shortlist to apply for the job

  • Review the list of people who have applied and evaluate them based on several criteria depending on the job. e.g. for a software developer we might be looking at - experience with the required technology, language skills, previous project relevance , feedback from other customers.

  • Schedule online interviews with the top 3 or 4 candidates.

  • During interviews, evaluate technical and communication skills and vote to decide if they can proceed to the next stage.

  • If fewer than 2 are good enough then go back to inviting more people to apply.

  • If we have at least 2 that are deemed good enough then offer them a small fixed time (or cost) piece of work that is relevant to the actual role. We explain that this will be paid by us and is the last step in the process.

  • Provide enough information for the tasks as per our usual process. There is no need to do more than the usual as this will create a less than realistic scenario for them.

  • Allow the candidates to ask questions and ensure they have a quick way to talk to us and get their questions answered.

  • At the end of the period evaluate the work the candidates have done, how they communicated, what questions they asked during the process and how early and how often did they seek feedback.

  • Finally, make a decision. If we can’t approve at least one of the candidates we go back to Inviting more people to apply for the job.


We have used this process multiple times to build up our holiday planner team, and all hires since we started using it have been successful. For clarity we define success as someone staying in the job for at least 2 years. One might question the fact that we are paying 2 or sometimes 3 people to do a piece of work which may not end up adding any value at all. And at first glance, yes, this looks rather inefficient. However, our experience shows that it massively increases our chance for success.


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