My Friend my boss
In his book Small Business Do's and Don'ts, author Sam Safar writes, “One of the fastest ways to ruin a happy family or close friendship is to hire a family member or a friend to work for you”. I suppose many people who have had the experience of working for a friend or family member (or vice versa) would emphatically agree with this statement. Indeed, even people who have never had the experience themselves seem to line up instinctively in opposition to it.
Loss of equality. In most friendships, the two individuals have the same power/status. In the main, friends do not tell friends what to do. Now imagine that the situation is different: your friend now has the right to instruct you to do something and you must comply. In most situations, you and your friend presumably agree and there is no problem, but in those cases where you disagree - - possibly even disagree sharply - - the door to bitter feelings may open. Similarly, imagine your friend - - a person with whom you joke around, have fun, share stories - - calls you into her office to reprimand you for a perceived mistake on your part. Again, you have little choice but to accept it, though such a scolding may be very difficult to swallow or to forget. In this way, the easy equality of friendship is subsumed by the hierarchy of corporate life.
The “Grey Area”. The blending of one’s personal and business life inexorably leads to the development of “grey areas”. When two friends work together, the ordinary distinction “personal” and “professional” starts to erode. Separating work hours from personal hours grows more difficult. You may end up talking about work-related issues over lunch or other gatherings outside the office. Your boss/friend may feel comfortable asking you for types of support that he would never ask of a non-friend/employee. Emotions provoked in one setting may be hard to contain in the other. Personal conflicts are difficult to leave at the office door. In this way, a level of uncertainty and awkwardness may infiltrate both the work environment and the friendship too.
Over-Exposure. Given the busyness of modern life, many of us wish we had more available time to spend with our friends. Indeed, part of what makes our time with friends so special is that it is often a scarce commodity. Close colleagues, however, do not have this problem. If you work in the same office as your friend, you may see them 5 days a week, 9 hours a day - - more time than you spend even with your dearest family! Will it come to the point where you actually feel like having a break from seeing your friend outside of work hours, especially now that there is a good chance that work-related issues will creep into your private conversation? In this way, being colleagues can undermine the rarity or quality of the friendship.
Difficult Exit. And lastly, how easy it would be to tell your friend that you have found another job and that the new offer is better than the current one? No matter how logical your arguments, I suspect it would be hard for most of us to tell our boss/friend that we no longer want to work with them. He may well feel betrayed, let down, or implicitly criticized by our decision to leave. Truth is, the days we spend serving our notice period after resigning can be a little awkward even in the absence of a personal relationship with the boss. Given that the friendship dynamic may well lead your boss/friend to feel you are quitting not just his company, but the friendship itself, such situations are rife with complexity and challenge.
I realize I reveal something about myself when I admit that, despite the consistency of the arguments against it and despite the self-evident nature of the warnings I received, I decided to take the job working for my friend anyway. This was not mere stubbornness (or foolishness) on my part, but rather a desire to counter the conventional wisdom and make it work. In doing so, I looked for inspiration to stories of friends working together where the business thrived and the friendship grew. One such example would be Larry Page and Sergey Brin, founders of Google. Having met at Stanford in 1995, Larry and Sergey became friends and started to work on a project together called ‘Backrub’, later renamed Google. Despite the pressures they undoubtedly faced, despite the vast sums of money that came into play, despite the incredible growth and complexity of the business they founded, Larry and Sergey still work closely in the same company even today.
I admit that, in taking a role reporting to my friend, I was at least armed with the knowledge of what could go wrong. But after working in the office for 2 years as on a part-time basis while completing my Bachelor’s degree, I actually went on to become a full-time employee after my graduation. While it is true that working for a friend can ruin a friendship, I am pleased to say that it did not ruin mine. Indeed, I had a wonderful, formative experience working for my friend and though I have since moved on, our friendship continues to thrive.
Drawing on that personal experience, as well as the rare but powerful examples of those who have made a personal/professional relationship work, I would outline here the four elements that I think are essential to make such a combination successful.
Accepting Compartmentalization. It is important for both parties in such a relationship to be professional, striving at all times to separate personal feelings from the business. At work, for both of you, the best interests of the company must be paramount, and personal or friendship considerations must be back-burnered. When your boss/friend asks you to do something for the company, you should accept it without upset and do all in your power to deliver on the objective set for you. If you are uncomfortable or unclear with the task, discuss the matter with your boss/friend, but in a professional way rather than appealing to your friendship as a reason to be excused.
Similarly, if there is a disagreement outside of the office, keep it outside the office. Bringing one’s unhappiness into the office or performing one’s tasks in an unwillingly or reluctant manner only undermines one’s value as an employee. As a corollary, if your boss/friend asks you for a professional favor in the name of your friendship, you should be able to remind her of the line between your personal and professional relationships and ask her to honor it.By maintaining compartmentalization to the degree possible, we actually help to diminish tensions that might otherwise arise. For example, compartmentalization will allow you to resign your position without guilt or undue anxiety. When I was approached by my current employer and presented with another opportunity, for example, I felt comfortable sharing it with my boss/friend and we were able to discuss the alternatives and our respective points of view without awkwardness or too much emotion.
Clarifying Expectation. Right from the start, it is vital that we obtain an absolutely clear sense of the job, the culture, and our friend’s management style (ideally capturing his expectations of us in writing). This is good sense before accepting any job offer, but it is especially important when working with a friend because the likelihood of mistaken assumptions or misaligned expectations is doubly high when a natural trust between the parties already exists. The key is to reduce ambiguity and avoid future disputes. For example, when I started working for my friend, I assumed he would not ask me to do things that were clearly below my qualifications or position. As I quickly discovered, however, in small entrepreneurial firms like his, employees are expected to multi-task and everyone from time to time takes on the ‘menial’ tasks of the office, including the boss. I was able to take this in stride, but would have been better off had I understood it in the beginning.
Leveraging Communication. Communication, both prior to joining and after beginning employment, is vital. You and your friend will need to be able to voice any concerns at any point in time. Holding on to issues for fear of offending your friend will lead to a build-up of unhappiness until, eventually, any small event may ignite your emotions and lead to an unplanned, unprofessional outburst. Such outbursts undermine our standing as professionals, of course, but may also do lasting damage to the friendship. In the beginning of my employment, my friend took kind efforts to check on me regularly, asking me how I was doing, and ensuring that I was happy and rooting well in the business. Over time, however, responsibility for initiating our check-ins with each other became my job. But whether he or I initiated, I found that keeping the dialogue open invariably led to conflict avoidance and deeper understanding between us.
While I agree that working for a friend or family member could imperil the relationship, I also believe that such pairings can yield extraordinary results and a more profound personal happiness and professional satisfaction for both parties. The key is not whether we pursue such relationships or not, but how we handle them when we do pursue them. If both parties adhere to the principles outlined here, I strongly believe that something rewarding and positive can result from the experience.
I know that it did for me. After leaving my friend’s company, we still spend time together, share meals, and carry on our friendship. In fact, the experience was so positive for me, and I had so much confidence in my ability to navigate such complexity, that in my new job I am working for another close friend. In light of the energy and motivation this provides me, I would not have it any other way.
-Rongine Koh