Preparing to be Unavailable for a Time

What do you do when something comes up, and you must step away for a time? How do you and your team prepare for such a thing?

I suppose this scenario could take multiple forms. Sometimes it is only a temporary stepping away. Sometimes it is permanent. Sometimes it is just time to move on to the next adventure. However, for this post, I am focusing only on temporary scenarios — perhaps a maternity/paternity leave, the need to care for a tragically ill family member, a long vacation, or an unexpected health crisis. Transitions are never easy. However, when something happens that means you (or a critical team member) must step away, it raises a whole host of challenges in a small startup that would likely be less of an issue in a larger, more established company.

Small teams rarely have great backups

The very nature of a small startup is that you often have a team with interlocking complementary skills, but rarely do you have a deep bench to draw on. Whereas, at a larger company, you might have a department of ten people handling a particular function and the temporary loss of one person represents only ~10% of the team’s capacity, an amount that the other 90% should be readily able to absorb. At a small startup, however, a particular function will often be handled by one or maybe two people, and the temporary loss of one can be 100% or 50% of that function. This demands much more creativity in developing backup plans when someone is going to be out for weeks to months.

Yet the show must go on

The challenge of a temporary stepping away is that the startup’s work continues unrelentingly on. Now the organization’s problem becomes how to adapt to the loss of a significant chunk of its expertise and resources for handling a particular function for a material length of time. Here are some strategies that I have used when needing to handle such situations, recognizing that the criticality of the person’s work, the length, and completeness of the stepping away are factors that will influence what combination of strategies can best compensate for the loss:

• Bring in a substitute:  Once, my CFO texted me during a Board meeting to announce that his trip to visit his doctor that morning had turned into an emergency cardiac procedure. He was headed to the OR now and unsure what the recovery would look like. With the looming uncertainty and the criticality of the CFO’s role, I reached out to a fractional CFO that I knew and asked him to jump into the fray immediately while we determined when I would get my regular CFO back. In the end, it was only a few weeks, but at the time, we didn’t know, and calling in a specially skilled temporary replacement was sound mitigation. A fractional, consulting, retired, or otherwise available-on-a-temporary-basis person with the right skills can be an excellent solution to a temporary gap.   
  
  
• Make a coverage plan:  Managing someone’s work always starts with making a list of what the individual is responsible for. While ideally, this list is generated with the person, a possibility when there is some warning of an impending stepping away, sometimes a manager or colleagues will have to do their best if something sudden comes up. Regardless a list enables considered planning about how to manage coverage.
  
  
• Put the brakes on the nonessentials: Review the list of things the person you are seeking to cover for is responsible for and take a hard look at what can simply be de-prioritized for a time or even skipped altogether. This tactic works particularly well if you are trying to cover for someone with bits and pieces of others’ time
  
  
• Outsource: Sometimes, it makes sense to outsource some portion of the work. For example, we retained a recruiter to take over the work of making progress on a critical hire when the hiring manager was unavailable for a period. Sometimes you can ask a supplier or service firm to take over some functions temporarily. This can work especially well if the supplier or service firm is already working with the individual who will be out, so the outsourcing task is more about changing the scope of an existing relationship rather than spinning up a whole new relationship.
  
  
• Prioritize and spread the load: Once you have reduced the list to essentials, leveraged external resources as possible, and determined what remaining work must be covered, think about who on your existing team might be able to pick up some of the pieces temporarily. Often this creates a bit of a prioritization cascade as you must also free up time on your substitutes’ responsibilities and priorities. It is unlikely that a high-performing team just has a bunch of extra capacity available. Hence, as you divide and conquer the work of one key person to enable handoff to alternates, you should consider easing the objectives of the people who will be absorbing their work. What you do not want to do is just imagine that you can shove ten pounds of potatoes into a five-pound sack. Instead, be aware and intentional in shifting responsibilities, priorities, and objectives to ensure that the most important things are still getting the required attention and you are thinking through what will get left undone.
  
  
• Be transparent and set expectations: Be sure to share with your team the plan so everyone can rally around filling in any gaps and support the people covering for your missing team member. Be proactive in letting those external people who interface with the person who will be missing in action for a time know about the absence and who to contact in the meantime. By being proactive, you build confidence that your team will take care of things for these important people.

How it feels when you are the one on hiatus

When I recently had to step away for weeks to cope with a medical issue, I wrestled with feelings of guilt for letting my team and stakeholders down, for not being able to carry my responsibilities and deliver on my commitments. I doubt I am unusual to feel this way because, like many of my founder-CEO peers, I think of my startups like beloved children and feel a tremendous sense of ownership and responsibility for them and for everyone who has joined, invested in, taken a chance on, and otherwise supported our efforts. While virtually everyone kept reminding me that it was essential to take the time to take care of myself as my top priority, it was still difficult to watch the rest of my team absorbing my work in my absence and acknowledging that, while we would all do the very best we could, there were parts that were just not going to be covered in the same way as they might have been because of missing context, skills, background, experience, capacity, and any of the overall combination of factors at play that make situations like this suboptimal. Nonetheless, everyone we engaged in helping us both internally and externally was committed to supporting me and making the best of it. The silver lining was that my temporary absence was a forcing function for upgrading our processes and documentation, accelerating some conversations with critical stakeholders, and opening up room for others on the team to step up and contribute at new levels. In the end, hindsight may prove that we gained as well as lost during this temporary season – and one never knows going in what blessings may emerge from the hardship.