Should you follow your boss to their new job?

It all starts with dinner table conversations

My 10 year old son loves playing this game at the dinner table every night. He asks us a question starting with “Would you rather……”. Often we are peppered with ridiculous choices such as “Would you rather have 30 million dollars or 30 million friends?” He won’t take “it depends” for an answer and ironically, engaging in this game is compulsory; there is no choice in the matter. We readily welcome this imposition feeling grateful, relieved and comforted that our son is still engaging in some form of conversation or dialogue with us.

I am going to take a leaf out of my son’s book today with a question in the context of Career.

Would you rather follow your boss?to their new company or stay in your existing set-up?

A reminder of the rules of the game - you cannot say “it depends”. What if you had to make this choice blindly, would you go for it? Many of my friends and colleagues tell me that they have done exactly this – followed their boss, no questions asked (Mogambo style) and that they have struck gold in the process. And yes, I believe them.

Boy, was I clumsy at this!

Before going any further let me tell you that I have sucked at making this decision for myself many times. Whenever I was presented with this choice I froze. I was overwhelmed with myriad thoughts and feelings. ‘What if’ scenarios, Plan Bs, repercussions, loyalties, and relationships danced around in my consciousness as I grappled with this situation. My articulation and communication skills were put to the test when summoned by a previous boss to state my decision. I typed and deleted numerous text messages on my phone without sending them. I was afraid, confused, excited, flattered, humbled and delighted at the same time. Finally, I wound up saying no but I definitely bagged the lifetime achievement award in the ‘most clumsy response ’ category.

As luck would have it, this decision to stay back would often hit me quite hard. The culture and the day-to-day functioning styles would get dramatically altered with the advent of the new leader/management team. Sometimes, it meant that I slipped down from the pole position I had occupied with the previous leadership team. I had to reset, readjust, readapt, rebalance (add a host of other words starting with “re”). In essence, I would be back to where I was when I first joined the organization. Sometimes it even had an adverse effect on my career growth. When the highly praised/regarded person is showcased to the new leader, the latter may tend to get suspicious, even insecure and can sometimes foster hidden resentment. This may typically happen when the new leader wants to distance themself from the previous one for a host of reasons.

Is there such a thing as a ‘boss soulmate’?

I have discovered that chemistry, respect, appreciation and understanding from a boss/leader can be a rare commodity. I found myself advising youngsters to hold on to this relationship if they can. “Trust and rapport is everything,” I would tell them. It was almost as though I did not want them to repeat my mistake (as I seemed to interpret it). When new leaders were transactional, task-oriented and not so humane in their approach, it used to further reaffirm my belief that one should have gone with the ‘tried and trusted’.

Can one design a career based on this premise?

Both choices have payoffs; there are countless articles on the web on the pros and cons of each approach. Perhaps it is a personal choice, but I wonder if one can design a career solely on this premise of following the boss. Does this come more easily to some people than others?

If I have to analyse this from an objective standpoint I might examine some key factors such as:

Am I betting on the right person? Do they have what it takes to reach dizzying heights and in the process take me with them?

Can I survive, grow and flourish in my existing set-up especially without this boss? Does the context/environment allow this?

In the same vein, what is my personal relationship with risk taking, change, ability to navigate diverse stakeholders/bosses, inner drive and a host of other relevant qualities? In other words, how important is it for me to have a ‘godfather or mentor’ like figure to succeed in a given organization?

What is my view on the organization that my boss is joining – especially if it is a smaller or a lesser known entity?

In reality, there may be many more factors and this can get complicated. Some may have an intuitive feeling regarding this whole thing and may be able to back their instincts accordingly. Others may examine the specifics, discuss with their significant others and/or carry out some research to arrive at a ‘calculated risk’ assessment of the scenario. Still others may focus mainly on the relationship dynamic with some situational specifics in the background. Personal factors no doubt play a role in choosing which path is taken to get to the decision.

Does it take a believer?

Again, some of my colleagues and friends who have done this tell me that they did not over-analyse such situations. They took a leap of faith and moved on. I find that fascinating.

The Danish philosopher Soren Kierkegaard said ‘life is not a problem to be solved but a reality to be experienced’. The ‘leap of faith’ team subscribes to this school of philosophy. They will probably say “that’s all there is to it”.