I got an interesting question in response to my last post from a startup CEO, let’s call him “Randy”, that I thought I would publicly answer since it seemed both interesting and important.

“I was intrigued by your [last] post…I am also the CEO of a small startup with eight people under me. I find it incredulous that you are able to take a whole month off in the middle of the year, and not have any consequences. Don’t clients and staff call you all the time?…

…I know I need a break, but there is so much work to do. The team depends so heavily on my direction, that going away for longer than a week (while the rest of my team works) is unthinkable. And it seems to be true of all the other people I know who are in a similar position… On breaks, I take my work on the road with me, or the whole office goes as a group. So its not clear to me how you do it, and in some ways makes me question the nature of your work…”

Randy, you have a great point, and let me try to answer your queries!

Before I begin, please understand that taking any time off beyond a couple of days takes immense preparation, as you will see. So impulsive trips (unless emergencies) simply don’t happen.

That said, here’s how I do it:

• Establish strong communication and teamwork in your company: For anyone to take time off, its really important that your team is strong and communicating with each other. As I said in my last post, it became very obvious that this was an issue at Month #8, so I set about fixing that. Now its critical that every person has two people to cover them at any given time, which means that people can take leave at any given time.

• Block out your dates a minimum of 3-6 months in advance, after talking to your team: Taking a month off (actually any time off longer than a couple of days) takes immense amounts of preparation. You need to mentally prepare your team for it, and you need to be mentally and emotionally committed to sticking to those dates. First, once I’ve figured out a period that I think will work, I usually talk to my immediate support team to see if there are significant conflicts or issues that I may have missed. If they don’t see any, I then speak to the investors/Board/owners, and once they approve (which they usually do because the rest of my support team is on board), I block the dates off immediately in the company calendar. Its very important to do this because it starts the process of clearly demarcating that time for yourself. Often people are much more forgiving of your departure because they have known for so long.

• Involve your team in the decision making; explain your thinking: While the owners know why, I had to explain to my team and the wider company why I needed to take time off. In the beginning, not everyone agreed, or understood, or was on-board. However, the most important people (my immediate support team), being the good people they are (and seeing how worn out and exhausted I was), got it…which mattered most. The rest of the company was much more supportive after the first time I took a break. They saw the difference in my energy levels, the freshness of my thinking, and how it trickled down to them personally and professionally, so it became easier for them to support my sojourn the second time.  More importantly, they realized that they weren’t abandoned and had no reason to panic.

• Develop a contingency plan that is internally shared, train your team, and remind them constantly: Make sure you develop a contingency plan for your duties so that your team will know when and how to back you up, and start training them well in advance. Make a clear outline of your duties and then delegate each of these to your support team members. Then pass this information out to the whole office. Remind them constantly that you will be out-of-town.

In my case, I met with my support team first to ensure they were comfortable with the new responsibilities. They were often trained months in advance and I even sent staff over to test out their respective capabilities as back-ups. It forced them to pick up new skillsets and capabilities. I also met with my team AS A TEAM, so they always knew what the other was doing. Communication is absolutely key. A month or two before my departure, I announced the information at our firm-wide meeting, and opened it up for questions, comments, or concerns from everyone.

• Plan your work out in advance so that you or your team aren’t overly overwhelmed: Your team is likely already stressed out about your departure, so don’t make it worse for them. Plan your work well ahead so that they aren’t hit with a brick wall when you depart.

For example, in my case, recruiting (particularly the interviewing and decision-making) was one aspect of work that I could NOT delegate to anyone in my team – they simply lacked the capability and confidence to do it correctly. So I took it off their plate completely and worked around it. Three months ahead, I got a clear idea of what HR needs existed in the office. I then paced myself to ensure that these were met prior to my departure. And I spoke constantly to the whole office to bring HR needs to the front as soon as they emerged so that they could be resolved before I left. Amazingly it worked, and while I was gone, people were so busy adjusting to the new people and work, that I barely heard a peep from anyone.

• Keep your team busy with clear deliverables on your return, and hold them accountable: I’ve generally found that people create more drama when they don’t have enough work on their plates, and nothing to aim for. Prior to my departure, I ensure that everyone in the company has clear deliverables and targets that I will need to be updated upon my return. This has been magic in terms of not being bothered. Even if I end up extending by a couple of days, it usually is fine because people are thrilled with the extra time. Upon my return, I immediately followed up and ensured that things were done to my satisfaction. Essentially they were held accountable.

There are about 30-50 staff members in my company on any given day (the swell depends on interns and part-timers who work only certain days of the week or month). I am generally clear about the nature of my output and  while I am the “CEO” or “Managing Director”, my work is primarily administrative in nature. I have a number of people who can back me up and hold the fort in the case of an emergency. On the design side, which is our ultimate “product”, I do very little. This was designed around my skillset, the type of talent pool we had access to, and how best I could add value to the company. I could and did hire lots of good people who do excellent design, took most things non-design off their plates, and put that on the plates of people like myself, and a few others who could handle it. For now, this works brilliantly. And this is how I do it 🙂

Hope this answers your question.