“Entrepreneurs can even do it as a hypothetical exercise without physically taking a holiday. The entrepreneur should ask questions like: Which system will potentially be the first to collapse if I am not around? Which form of work will start piling up if I am out of office for an extended period? Which staff members can be put in charge of certain processes and responsibilities in my place?"
The answers to these questions, according to Kalaile, will tell the entrepreneur which departments in the business need the most work, which tasks they should delegate and which team members can be brought into the management team.
“The short-term plans that entrepreneurs put in place to keep 'the ship afloat' while they are on holiday are often the first steps towards permanent solutions that will make the business more robust and less dependent on a single person.
“If certain tasks delegated during the entrepreneurs' holiday were carried out successfully, it can become a permanent arrangement, freeing up the business owner to focus on issues such as expansion," explains Kalaile. “The same is true for new roles and responsibilities given to staff members."
Kalaile says that many entrepreneurs find the notion of taking a holiday to be inconceivable. “This is understandable in the first year or two of an enterprise, when everything tends to revolve around the entrepreneur. However, in an older business it may indicate that the entrepreneur has become too entrenched in operations and may have failed to set up proper management or legacy systems."
Although even the process of just planning a 'holiday' has its benefits, Kalaile says that nothing beats actually taking a holiday and putting these ideas to the test.
“Risks and anxiety can be managed by taking an incremental approach to holidays. An entrepreneur with a relatively young business can start off with a long weekend, and then add another day or two onto the weekend so that it becomes a solid week at a time, and later more than one week."
Another form of incrementalism that Kalaile recommends, is the extent to which the entrepreneur checks in on the business while on holiday, and under which circumstances staff and clients are allowed to contact the resting business owner. “In the beginning, it makes sense to err on the side of too much contact rather than too little. Not only does it help to minimise the risks of inexperienced staff members making the wrong judgement calls, but it will probably also make the entrepreneur less anxious about the business."
Of course this kind of holiday is far from ideal. “It is good for the entrepreneur and the business if the strictness of the rules about contact is gradually increased from holiday to holiday. For example, mornings-only contact can later be restricted to once a day, every second day, or even once a week if confidence grows that the business is in good hands," adds Kalaile.
“Although not all entrepreneurs feel like they need to take a holiday, the result is that they often miss out on the opportunity to test the robustness, growth and independence of the business. As such, it is imperative to go through the mental exercise, and hopefully taking a holiday might just start to seem like a good idea after all," Kalaile concludes.