I acknowledge we all share different priorities, backgrounds, and ambitions, leading to very different career outlooks. I’m thus not going to answer the above question for anyone else but myself.
I do find it important to address this topic in the context of startup leadership. Moving on opens up an opportunity for others, while allowing ourselves to tackle new challenges. It helps everyone realize more of their potential.
What I’ve realized in asking myself this question is that there’s never just one motive. Deciding to move on from one role to another is the result of many variables. I’m thus going to share a set of questions that have helped me make such a decision:
“Am I the best player in the band?”
Learning new things every day is important to me. Therefore, if I’m the best person at doing XYZ at my organization, chances are I’m not learning about XYZ anymore.
To quote, Louis Armstrong (I believe he said this): “If you’re the best player in your band, it’s time to look for a new band.”
This can however be a tricky question to answer, since learning to teach XYZ to another individual is also appealing to me. It’s not always about learning in the context of gaining new knowledge, but also giving new knowledge to someone else (especially as a leader).
In the end, it comes down to what my motives and goals are.
“Do I agree with where we’re going?”
It doesn’t matter if the company is heading toward a guaranteed gold mine or working on the trendiest technology. If the destination or strategic goals don’t jive with my personal interest, it’s a waste of time to me. I view the opportunity cost of not pursuing something I enjoy as extremely high.
For example, many people would jump at the chance of working on a space vehicle that goes to Mars, yet personally, I couldn’t care less. I am much more interested in solving problems with an impact here on earth.
“Am I more frustrated than I am happy?”
If I experience more anger, frustration, and sadness at work than I experience excitement, joy, and hope, it’s a sign I need to ask myself some serious questions.
My take on the goal of life is to be happy. If I am not happy now, I need to identify why, and do something about it. Yet sometimes, the negative emotions experienced at work can be r of issues outside of work. I thus need to be careful in finding the root cause of my negative feelings.
For example, I once experienced a period of frustration at work, getting upset at anything that didn’t go perfectly. I knew it was not related to work, but rather caused by an issue with my family. It was unacceptable and I needed to do something about it… So I worked to resolve my personal problem, which also made my days at work much more joyful.
“Do I trust the leadership?”
I need to trust that my leaders know where we are going, know why we’re going there, and are capable of taking us there. That they have an explicit strategy.
My trust for the leadership team tends to erode every time they say one thing and do another (words mean nothing anymore), don’t follow up on an ask of mine without explanation (don’t value my thoughts), or ignore concerns I bring up (don’t listen to what I have to say). At a minimum, I need to trust that they have the team’s well-being at heart. If they don’t, then there exists irreconcilable differences between my values and their. It would indicate that it’s time to move on.
A special case with inexperienced leaders / founders is their inability to act on their intentions. They will have the best intentions, but fail to execute. They lack skills, experience and knowledge. In that case, even though I trust their intentions, I do not trust their ability to lead. That’s a sign I need to advocate for more experienced leaders to take over, or move on as well.
“Am I excited to go to work?”
In one of my previous jobs, the first thing I thought about in the morning was leaving work and how I could shorten my day. I clearly didn’t enjoy what I was doing, wasting both my time and the company’s time.
“Is the culture toxic?”
Luckily, I haven’t experienced this first hand. But a friend of mine did.
His manager was verbally and emotionally abusive, often publicly blaming, shaming and yelling at my friend in public.
My friend didn’t fully recognize that his boss was wrong until he quit. The whole time this was happening, he felt responsible for the mistakes and problems blamed on him. It’s only when he compared his new job’s culture with his old one that he realized his manager’s behavior was abusive and discriminatory. To assess whether there exists an abusive relationship with our manager, I recommend reading the signs of abusive romantic relationships and replace “partner” with “manager.”
Beyond bad bosses, a company’s overall cultures can also affect our well being. Perhaps we’re selling products that hurt people more than they help, perhaps we’re deceiving our investors, or perhaps the culture simply doesn’t allow us to be honest with ourselves. If the culture is making me unhappy, it’s time to change culture.
Deciding to move on is difficult. It destabilizes our routine. Plus, we all have to pay bills, support our families, and respond to social pressures. Sometimes, no matter how unhappy we are, we stick with our job, thinking that it’s the best worst thing for us. I get that, it’s hard.
Yes, it does take courage to say no to a steady paycheck and look for a new job (which may not be any better), pursue a passion, travel the world, or found a company. But to make the switch easier, we can start by drafting a plan. Things suddenly get easier and look plausible once we identify small steps that we can take immediately, over the next weeks, and next months, to eventually achieve our goals.
We can work on our personal goals in the same way we helped our company achieve its goals. We can apply the concepts of scenario planning, market research, idealized design, and competitive strategy to our personal objectives. Don’t believe me? Many have done it… Check out “No fear no excuses” by Larry Smith.
Let’s ask ourselves: “Am I doing exactly what I want to be doing, and making progress toward my goals?”
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