I had the opportunity to receive feedback from one of my team leads yesterday. It was insightful and helpful as it usually is when I get good, thoughtful feedback (something that is rarely offered unless explicitly requested, it seems). During this discussion he and I discussed my status as a contractor and some hypothetical scenarios under which I might consider full-time employment with the company. I won’t divulge details of the conversation, but it was a good question that made me think about what it would take to draw me back into a 9-5 role.
Since leaving my last job six months ago, I’ve been given more offers than I can remember ever receiving during times where I was actively looking for work. It’s been a flattering and humble experience to be sure. But the primary reason I’ve turned them all down is because six months ago, I decided to bet on myself. For the first time in a big way, I wanted to trust that I could carve my own path, and six months is hardly a long enough period for me to gage the results of this experiment and turn back.
But is entrepreneurship my end goal? Would I ever give up and go back to working for the man? Perhaps! There are certainly tradeoffs and aspects that I miss. Ultimately the choice will come down to a few key questions that I’ll need to answer for myself about the opportunity in front of me. I derived these questions from the core values I hold close and consider any deviation from those values to be a non-starter.
- Does the opportunity provide me with a path towards my professional goals?
- Do I initially trust the person who would be directed with overseeing this path forward, and is there an accountability structure in place to measure progress and advancement?
- Does the opportunity provide the freedom and flexibility I need to live the life I want to live outside of work?
- Does the culture promote constructive two-way feedback, and is feedback provided to leadership truly welcomed and taken seriously?
This last question has become, perhaps, the most important in my mind. In my experience, a company’s culture can be made or broken by how bottom-up feedback is facilitated. Consider this all-to-familiar directive:
Well, this is clearly not the right way to do X. But [insert CEO/CTO name here] asks for this and so that’s how we have to do it.Too many team leads at too many companies
Red flag. Approach with caution.
Sometimes this is the manager’s failure; maybe not pushing back is just easier. Sometimes it’s just not a big issue and, well, we all have to pick our battles. But more often I believe it’s because the CEO/CTO in question has indicated, either directly or indirectly, that alternative opinions and feedback are not welcome, so the manager reverts to self-preservation mode. And if the executive team does not trust the folks they hire to bring valuable perspective and insight to key decisions, this is a deep cultural problem that is much, much more difficult to overcome.
If I do decide to dip my toes back in the water of employment, I expect hiring managers to have a good answer to this question.