It All Comes Down to Three(-ish) Simple Questions

Michelle Boockoff-Bajdek
3 min readApr 18, 2022


A good friend of mine who worked for a very large software company reached out to me one day. She was trying to decide whether she wanted to stay at the company or potentially move on. She had been wrestling with this incredibly difficult decision for some time; she’d spent the bulk of her career there — essentially had grown up there — and was conflicted.

She wanted guidance. She needed advice. Instead, I asked her three simple questions … three (well, three-ish) questions that have guided all of my career decisions and would soon guide hers.

I asked myself and then answered these questions when I learned of an opportunity at The Weather Channel. And again when I left IBM to join Skillsoft. And no, not one of the questions involves money. As recent research has shown, money is not usually the prime motivator or deciding factor when people go looking for their next opportunity.

So, here they are:

  1. Do you like the company you work for? Are you aligned with the mission? Do you believe in what the company stands for?
  2. Do you enjoy the people with whom you work every day? Do they share your values?
  3. Do you like what you do? Is your job fulfilling?

Now, it’s important to note: the first two are non-negotiables (for me, at least). The minute I can’t answer those two affirmatively, I know there is an issue. The third is a little squishier … because, let’s face it … there are days when work is difficult. And sometimes, our present role isn’t exactly perfect.

But if you have the other two? The third tends to work itself out. My own career attests to it — and never more so than with my current situation.

I’m happy to say that I made the right decision when I asked myself those questions nearly three years ago and joined Skillsoft. Skillsoft and my role there continue to check all of the boxes for me.

As a company, we do more than sell solutions; we help customers and their learners grow together, contributing to their mutual success in meaningful ways. And, we have the privilege of putting our platform to work for the betterment of society through non-profits like EllevateHER, the USO (Hire Our Heroes), and iamthecode, just to name a few. (#1)

When it comes to people, I can say unequivocally that I have never worked with a better team. They are not only exceptional marketers, but incredibly good humans. I’m very lucky. (#2)

So, one and two, check. What about number three? Yes, I’m fortunate there too. As part of Skillsoft’s executive team, I contribute to corporate strategy, serve as the company’s Brand Ambassador, support our go-to-market plans, and drive our corporate social responsibility initiatives. But, my most important job is to enable my people so that they can do their best work and be their best selves. There is no better job than that.

So now, back to my friend. I asked her those three questions and she hesitated right from the start. She didn’t feel as connected to the organization as she had in the past and wanted to work for a company with a higher purpose, one that was doing more good in this world (#1). And while she really enjoyed her team (#2), she wasn’t thrilled with her role any longer (#3). And so, she left to join a company focused on sustainable business practices.

Unfortunately, not every decision will come down to three simple questions. But, these are definitely worth asking. Think them through to uncover what matters most to you. Because nothing feels better than doing great work with good people for an organization you believe in.